POPULARITY
2 episodes with qsbs
2 episodes with qsbs
2 episodes with qsbs
3 episodes with qsbs
2 episodes with qsbs
3 episodes with qsbs
2 episodes with qsbs
3 episodes with qsbs
2 episodes with qsbs
Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you'll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- Are you running your business to scale, or are you running it to sell? According to Michael Bennett, managing partner and founder of Crew Capital, you should always be doing both. In this tactical episode of The Exit, Michael sits down with Steve McGarry to break down the exact playbook for preparing your business for a massive payday long before you ever want to hand over the keys. From tracking the 10 to 20 industry KPIs that actually matter to navigating the complex world of QSBS tax benefits and succession planning, Michael shares the hard-earned wisdom he used to help guide one client from a $50M enterprise value all the way to a public, multi-billion-dollar powerhouse. Drawing from years of investment banking and advising founder-led companies, Michael shares why the best time to prepare for an exit is before you need capital and how running your company as if it is always “sale ready” can dramatically increase enterprise value. Michael also breaks down the biggest mistakes founders make when preparing for a sale, why timing matters more than most entrepreneurs realize, and how market conditions can impact valuation multiples. Steve and Michael dive into minority deals, partial exits, rollover equity, and the difference between maximizing value versus defining personal success. Whether you are years away from selling or actively considering an exit, this conversation offers tactical advice to help you prepare smarter and avoid painful surprises. -- Michael Bennett is the Managing Partner of Crewe Capital and Co Founding Partner of Crewe Advisors, where he helps founder led and closely held businesses navigate mergers and acquisitions, capital raises, and long term financial strategy. Over the past 20 years, Michael has advised on more than 100 investment banking transactions while helping grow Crewe into a multi faceted financial platform overseeing more than $3 billion in assets. After overcoming an unstable childhood and putting himself through school, Michael built the firm from the ground up, starting with no clients and a single $20,000 retainer, eventually expanding into wealth management, alternative investments, philanthropy, and community initiatives. Website - https://crewecup.com/ LinkedIn - https://www.linkedin.com/in/crewecapital/ KEY TIMESTAMPS: [00:01] Introduction to Michael Bennett and His Journey [05:49] Preparing for an Exit: Timing and Strategy [08:58] Common Mistakes in Exit Preparation [11:48] Understanding Valuations and Market Trends [14:50] Defining the Right Time to Exit [17:46] Exploring Partial Exits and Deal Structures [20:46] Favorite Deals and Lessons Learned [23:41] Advice for Future Entrepreneurs [26:56] Conclusion and Overview of Crewe Capital -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You'll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
In this episode: IRS call strategies – A tip for getting through when the IRS won't accept calls • Tax identity theft – How fraudsters file returns using stolen Social Security numbers • Qualified Small Business Stock (QSBS) – A little-known tax exclusion that could eliminate gains for eligible investors • IRS First-Time Abatement – An automated penalty relief process coming soon for late filers • Investment fee deductibility – Why individuals can no longer deduct these fees, but businesses still can • IRS interest rate increases – Higher rates on underpayments and overpayments starting Q3 2026 • 2026 W-2 changes – New codes to identify deductible tips and overtime pay • SALT cap – The $40,000 state and local tax deduction limit reaffirmed through 2029 • 2027 HSA limits – Contribution limits going up, with a reminder of the long-term savings benefits
From selling candy in school as a kid in Medellin and getting robbed by his business partner, to riding the South Florida real estate boom and losing everything in the crash before he was twenty, Alex Lopez, CPA built his understanding of deals through lived experience long before he picked up an accounting textbook. Alex runs a CPA firm specializing in CFO services and tax minimization strategy, with over 12 years of experience at global accounting and consulting firms and in corporate America. He works with entrepreneurs in professional services, tech, and real estate, focused on helping them scale from six to seven to eight figures while keeping more of their profits out of the IRS's hands. His years as a financial auditor trained him to assess a business quickly, corroborate what owners claim, and identify which direction a company is actually trending. In this episode he walks through two contrasting deals: one where understanding why a buyer was willing to stretch above market multiples revealed hidden strategic value that let his client hold firm on price, and another where a single off-ratio insurance figure that nobody fully investigated masked a multi-million dollar misrepresentation that killed the deal entirely. He also shares the story of a seller whose insistence on cash over a higher leveraged offer turned out to have nothing to do with preference and everything to do with a pending white collar conviction. On tax planning, Alex is direct: by the time a deal is under letter of intent, several of the most powerful strategies are already gone. He walks through qualified small business stock, which can allow eligible founders to exit with little to zero federal tax on the capital gain from a business sale, but only if the company was structured as a C corporation and the stock held for at least five years. He described a young tech founder who called his firm last year with the deal locked and loaded to close, and paid a seven-figure tax bill because nobody had ever told him this option existed. The conversation also covers how S corporation elections that make sense for self-employment tax purposes can create complications in deals that include rollover equity, why founders who avoided C corp status to preserve early pass-through losses often give up far more in QSBS savings than they ever gained, and how structuring payouts over time can both spread the tax bill across lower-bracket years and give sellers leverage to negotiate a higher total price. For anyone building a business with any intention of eventually selling, this episode makes one thing clear: the time to think about these questions is years before you have a buyer at the table. FOR MORE ON ALEX LOPEZ, CPA: Website: AlexLopezCPA.com FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps [00:00] - Introduction: Alex Lopez's background in CFO services and tax minimization [02:54] - First deal: selling candy in school and the partner who stole everything [13:48] - Using ratios and anecdotes to spot market exuberance before it corrects [21:31] - Finding hidden value and why a buyer's motivation is negotiating leverage [28:45] - Why tax planning needs to start before there is a deal on the table [32:13] - Structuring payouts over time to spread the tax bill and negotiate better terms [44:13] - The seller whose insistence on cash pointed to a white collar conviction[49:37] - What freedom means: being oneself and at peace with one's surroundings Guest Bio: Alex Lopez, CPA is passionate about helping business owners scale, increase profits, and minimize taxes. With over 12 years of experience working at global accounting and consulting firms and in corporate America, Alex runs a CPA firm specializing in CFO services and tax minimization strategy. He works primarily with entrepreneurs in professional services, tech, and real estate. Alex grew up in Medellin, Colombia and came to the United States in 1999, getting his real estate license straight out of high school before the 2008 financial crisis redirected him toward accounting. That combination of early deal experience and deep technical expertise informs how he advises clients on both the financial and structural dimensions of their transactions. Related Episodes:Episode 350 - Tom Dillon: Business Valuation and Exit Planning Realities: Understand how valuation works in practice and what drives the gap between what owners expect and what the market will pay.Episode 330 - Pete Mohr: Building Enterprise Value and Exit Readiness: Learn how operational decisions made years before a sale determine what a business is actually worth when it goes to market.Episode 339 - Solocast 74: Equitizing Key Employees and Succession Planning Strategies: Explore how entity structure and equity decisions made early shape your options when it is time to exit.
In this episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., tackle eight listener questions on a wide range of tax topics. They open with a deep dive into the tax advantages of purchasing property in an Opportunity Zone, covering both the original program and the newly reinvigorated Opportunity Zone 2.0 launching January 1, 2027, including deferral periods, stepped-up basis benefits, and rural vs. urban pathways. They also explain required minimum distributions and the five-year Roth seasoning rules, the nuances of married filing separately in community property states, and strategies for reducing passive capital gains tax after a multifamily syndication sale. Amanda and Eliot break down Qualified Small Business Stock under Section 1202, including new tiered exclusion rates and documentation requirements, walk through K-1 preparation and 1065 filing for limited and general partnership structures, and cover the Accumulated Earnings Tax for C corporations. The episode wraps with guidance on claiming education expenses for new businesses, amending prior-year returns, and using C corporations as the right vehicle for startup cost deductions. Tune in for expert advice on these topics and more! Submit your tax question to taxtuesday@andersonadvisors.com Highlights/Topics: [00:00] — Intro and questions [10:04] "If I'm still working for the company that sponsors my 401k when I turn 73, even if it's part time, do I need to take RMDs or required minimum distributions from that account? And once my Roth 401k is quote unquote seasoned for 5 years, if I roll it over to another Roth IRA account I have already had for 5 years, am I still able to take out the profits tax free?" - Still employed means no RMD required unless you own over 5% of the business. [13:42] "I am looking at a couple different commercial rental properties. One of them is in an opportunity zone in Florida. What are the benefits slash tax advantages of purchasing a property in an opportunity zone? Are there any downsides?" –Opportunity Zones defer capital gains tax with stepped-up basis and potential ten-year appreciation exclusion. [22:08] "My husband and I file separately. I itemize and my accountant said because I itemize, my husband must also itemize, which is worse for him as he loses out on the standard deduction. Is there any way around this? In addition, the IRS wants to know my salary on his return, which then leads to him owing tons of additional taxes. How can this be? Why would he be taxed on my income? I'm already being taxed on my income. So this year he left my salary blank on his tax return. Will this come back to bite him and incur fees? We file separately for many reasons, including me having rentals and he has child support and other things affecting his return." - Community property states require spouses to split income; no double taxation occurs. [30:32] "I was a passive investor in a multifamily unit deal. The property was sold and my CPA informed me that I have capital gains tax of 55,000 for 2025. Anything I can do to reduce this tax? If not, what could I have done differently?" - Cost segregation on existing property can create passive losses to offset the gain. [36:57] "I'm investing 250k in a software startup pre Series A. The founders say it qualifies under section 1202 as a qualified small business stock or QSBS. Let's say the stock grows 10x over the next 10 years, so my stock becomes worth 2.5 million. Ten years from now, how do I prove to the IRS that the profit should be tax free under section 1202? Do I just document it now and hope they agree when I file an 8949 when I sell? It seems like there are no assurances they'll agree and the profits, though not subject to income tax, still become part of my estate, potentially subject to estate tax. Is it just easier investing using my Roth to ensure that all future gains will be income tax free?" – Thorough documentation of C corp status and assets under $75 million proves 1202 eligibility. [48:20] "Anderson created my limited partnership and general partnership structure. My questions are which entity has to create or issue a K1 and who prepares it for me? And when preparing the 1065 tax return, who do I list as the limited partner, me or the entity?" - The limited partnership files the 1065 and issues K-1s; list yourself as the limited partner. [50:16] "I invested in education for several businesses last year. None have come to fruition yet. Is the education able to be claimed on 2025 taxes? Also I filed without any of the education being claimed. So I was wondering if I could amend my taxes at some point this year." - Amend within three years; a C corp can claim education costs as deductible startup expenses. Resources: Tax and Asset Protection Events https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=the-tax-advantages-of-purchasing-a-property-in-an-opportunity-zone%20&utm_medium=podcast Schedule Your FREE Consultation https://andersonadvisors.com/strategy-session/?utm_source=the-tax-advantages-of-purchasing-a-property-in-an-opportunity-zone%20&utm_medium=podcast Anderson Advisors https://andersonadvisors.com/ Toby Mathis YouTube https://www.youtube.com/@TobyMathis Toby Mathis TikTok https://www.tiktok.com/@tobymathisesq Clint Coons YouTube https://www.youtube.com/@ClintCoons
When Omar Morillo talks about wealth management for entrepreneurs, he focuses on one core idea: reducing lifetime tax drag across income, investments, business operations, and eventual liquidity events. The earlier owners start planning, the more options they have. In this episode of the DealQuest Podcast, Corey Kupfer sits down with Omar Morillo, founder of Imperio Wealth Advisors, to discuss what sophisticated pre-exit planning actually looks like for business owners preparing for major liquidity events. Omar breaks down the three levels of tax-aware investing, from simple ETF investing to direct indexing and long-short strategies designed to generate capital loss carryforwards for future gains. He explains why many of the best planning opportunities disappear once an LOI is on the table and why advanced preparation matters. The conversation also explores estate planning, donor advised funds, PPLI structures, and the risks of “flavor-of-the-month” tax strategies that are often oversold to entrepreneurs. Corey and Omar also discuss the emotional side of exits, including why many founders struggle with identity and anxiety after selling the business that defined their lives for years. This episode is packed with practical insights for entrepreneurs thinking about exits, recapitalizations, succession planning, or long-term wealth strategy. WHAT YOU'LL LEARN Why reducing lifetime tax drag requires planning years before an exit The differences between ETF investing, direct indexing, and long-short strategies How carry-forward capital losses may help offset future gains Why estate planning and liquidity planning matter before a sale The risks and realities of structures like PPLI and QSBS Why founders often struggle emotionally after successful exits OMAR'S JOURNEY Omar Morillo originally planned to become an airline pilot before eventually finding his way into wealth management. Today, he is the founder of Imperio Wealth Advisors, where he advises entrepreneurs and families on tax strategy, liquidity planning, investments, and long-term wealth management. He approaches advisory work through what he calls an “agnostic lens,” focusing on the right strategy for the client rather than attachment to any single product or structure. FOR MORE ON THIS EPISODE https://www.coreykupfer.com/blog/omarmorillo FOR MORE ON OMAR MORILLO LinkedIn: https://www.linkedin.com/in/omarmorillo/ Company: https://www.imperiowealthadvisors.com FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where entrepreneurs and business leaders share insights, challenges, and success stories around deal-driven growth strategies. The show covers mergers and acquisitions, capital raising, strategic alliances, joint ventures, succession planning, and more. Episode Highlights with Timestamps [00:03:00] - Omar's background and accidental entry into wealth management [00:09:15] - The four layers of lifetime tax drag [00:16:40] - Why pre-exit planning must begin years before an LOI [00:22:10] - The three levels of tax-aware investing [00:30:45] - Direct indexing versus long-short strategies [00:38:20] - PPLI structures and investor control concerns [00:45:50] - The Miami Dolphins estate planning example [00:50:15] - Donor advised funds and charitable planning [01:02:00] - Omar's definition of freedom and legacy Guest Bio Omar Morillo is the founder of Imperio Wealth Advisors, a boutique wealth management firm serving entrepreneurs, business owners, and families navigating liquidity events, tax strategy, investment management, and long-term financial planning. He is a Certified Financial Planner (CFP), Accredited Investment Fiduciary (AIF), and Chartered Financial Consultant (ChFC). Omar specializes in helping clients reduce lifetime tax drag through coordinated strategies involving portfolio management, estate planning, charitable planning, and pre-exit structuring. His clients are typically entrepreneurs and business owners with substantial wealth concentration and upcoming liquidity events. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast.Related Episodes Dave Hersh: Founder Identity and the Emotional Impact of Exits DealQuest Wealth Management Series with RIA Industry Acquirers Tom Dillon: Understanding Business Valuation and Exit Planning Realities Keywords/Tags pre-exit tax planning, wealth management for entrepreneurs, direct indexing, long-short investing, PPLI, private placement life insurance, donor advised funds, estate planning, liquidity event planning, tax-aware investing, founder psychology, business exits, capital gains planning, ILIT, QSBS, entrepreneur wealth strategy
Angel Academy Session 5 brings in Brian Dirkmaat, a startup attorney at Procopio and longtime SDAC sponsor, to walk the room through the legal mechanics of angel investing. Brian covers the full evolution of startup investment instruments - from the original bridge notes of the 1990s to today's post-money SAFEs - and breaks down the real differences between convertible notes, SAFEs, and priced equity rounds. The session goes deep on valuation caps, pro rata rights, the unresolved IRS question around QSBS treatment for SAFEs, and the practical tradeoffs between investing directly into a company versus through an SPV. If you've ever looked at a term sheet and wondered what you were actually signing, this is the session.Key Topics* The evolution from bridge notes to convertible notes to SAFEs* How YC's post-money SAFE works: valuation caps, discounts, and MFN provisions* SAFE vs. convertible note: the unresolved IRS code 1202 (QSBS) question* Priced equity rounds: Series Seed vs. Series A (NVCA docs)* SPVs vs. direct investing: platforms, carry, admin fees, and when each makes sense* The California C Corp trap: unpaid founder wages and W-2 classification* Term sheet fundamentals: liquidation preferences, anti-dilution, board seatsLinks & Resources* San Diego Angel Conference (SDAC)* Procopio* YC SAFE Documents* NVCA Model Legal Documents* Rising Tide PartnersConnect on LinkedIn* Brian Dirkmaat* Neal Bloom This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit risingtidepartners.substack.com/subscribe
"Companies are bought, not sold."That single line from Yves Frinault reframed the entire conversation on our first-ever Exited Founder Acquisition Roundtable.We sat down with four construction tech founders who collectively sold their companies for hundreds of millions:✅ Yves Frinault (Fieldwire → Hilti) ✅ Dustin DeVan (BuildingConnected → Autodesk, $275M cash + $40M stock) ✅ Mo Akbari Hochberg (HoloBuilder → FARO, ~$36M) ✅ Zach Scheel (Rhumbix → Autodesk, fresh off the deal)Tune in to find out:✅ Why Hilti told Fieldwire "we'll never acquire you" four years before acquiring them ✅ The one negotiation tactic Dustin says every founder should use against corp dev teams ✅ Why an acquisition is a "one-way door" once you walk in, and how to know you're ready ✅ The QSBS detail that decides how much of the exit you actually keepFull episode on Spotify and YouTube now.#aec #construction #constructiontech #bricksandbytes #bricksbytes #bricksbucksandbytes #ai #vct Our Sponsors:BreadCrumb- 50,000+ projects globally. All running safer, faster, with Breadcrumb. - breadcrumb.coAphex is the multiplayer planning platform where construction teams plan together, stay aligned, and deliver projects faster – check out aphex.coArchdesk - “The #1 Construction Management Software for Growing Companies - Manage your projects from Tender to Handover” check archdesk.comChapters00:00 Intro00:46 Introduction to the Acquisition Round Table03:25 Founders' Experiences and Lessons Learned 06:31 Understanding the Role Post-Acquisition 09:40 The Importance of Timing in Acquisitions 09:56 Sponsors 12:57 Fundamentals for Being an Attractive Acquisition Target 31:06 The Exit Journey: Building Value Before Acquisition 33:14 Business Fundamentals: Attracting Strategic Acquirers 36:04 Diligence and Documentation: Preparing for Acquisition 38:56 Revenue and Customer Love: Key Acquisition Drivers 41:13 Understanding ARR: Acquisition Thresholds and Market Dynamics 48:53 Negotiation Strategies: Preparing for the Table 54:46 Lessons from Exits: Growth as a Founder 01:00:45 Defining Success Beyond Numbers 01:02:42 Mindfulness in Leadership During Transitions 01:04:22 The Importance of a Strong Executive Team 01:05:20 The Shift in Perspective Post-Acquisition 01:06:11 Reflections on Founding and Structuring Companies 01:08:37 Creating Value Over Tax Strategy 01:11:21 The Reality of Startup Success Rates 01:11:54 Choosing the Right Company to Join 01:14:48 The Value of Collaboration and Shared Experiences
Washington's Proposed Millionaires Tax (SB 6346) and the "Seattle Tax Stack": Mechanics, Migration, and Real Estate Impacts Industrial Advisors Podcast hosts Bill Condon and Matt McGregor discuss Washington's proposed "Millionaires Tax," SB 6346, a 9.9% tax on household income above $1 million, noting it can effectively hit dual-income households and "lumpy" stock-based compensation. They describe a cumulative Seattle "tax stack" (9.9% state, 5% social housing, 2.4% JumpStart, 0.58% WA Cares) exceeding 18% before federal taxes, potentially reaching 55–60% total, and argue it could influence jobs, investment, sports free agents, and real estate demand, including taxation of Washington-sourced income for nonresidents. Using an AI-generated deep dive built from documents, the episode compares migration and revenue dynamics in New York and California, explains domicile-planning timelines, highlights QSBS (Section 1202) as a potential shelter, and emphasizes the risk that the $1 million threshold could be lowered, especially if tech valuations fall and projected revenues miss. 0:00 Cold open: the $1M household threshold 0:46 Introduction to Washington's proposed millionaires tax 2:08 RSUs, deferred income, and one-time tax events 3:10 Seattle's 18% local tax stack explained 5:31 Commercial real estate and Washington-sourced income 7:00 Investor demand, property values, and economic ripple effects 8:01 Why Bill and Matt used AI for this episode 10:15 AI deep dive: tax flight and wealth migration 11:19 Washington as a national tax policy test case 14:32 Revenue projections and the 21,000 filer base 15:22 The Seattle tax stack breakdown 16:50 Federal taxes and the 55%–60% combined burden 18:47 The real estate exemption in SB 6346 19:37 Lessons from Los Angeles Measure ULA 22:57 Luxury housing demand and high-net-worth buyer risk 24:11 2028 effective date and relocation planning 26:35 RSUs and "lumpy vesting" risk for tech workers 28:05 The marriage penalty in the proposed tax structure 30:06 QSBS as a potential shelter for founders 33:13 California, New York, and wealth migration data 36:38 Remote work and the new mobility of high earners 38:47 Why the $1M threshold may not stay fixed 41:04 Massachusetts and the risk of expanding the tax base 43:29 Tech market correction risk and revenue shortfalls 44:32 Final takeaway: the "leaky bucket" problem 45:06 Closing comments
In this episode of Investor Connect, Hall walks new and experienced investors through the term sheet basics that trip people up most often, starting with the type of security (SAFE, convertible note, or priced round), the total investment amount, and how pre-money valuation works in startup investing. He shares a simple ownership framework—pre-money plus investment equals post-money, and the investor's ownership is investment divided by post-money—then points out additional items to watch for, including price per share (in priced rounds), conversion triggers (especially for SAFEs and notes), and dividends. Hall then explains how term sheets tend to be founder-friendly or investor-friendly, and how to spot the difference. Founder-friendly signals include no expiration date on the offer, the option pool coming from both founders and investors, no confidentiality agreement, no liquidation preference, and the company not paying investor legal fees; flip those and you're looking at investor-friendly terms. He emphasizes that term sheets aren't formulas—they're negotiations—and that valuation, liquidation preferences, investor/founder rights, and redemption rights can be traded to balance a deal. Hall closes with a practical overview of convertible notes as a rolling-close debt instrument that converts to equity at maturity or a qualified priced round, along with the risks of stacking notes and creating more dilution than expected ahead of a Series A. He notes that many notes have few protective provisions (though the Angel Capital Association released a model note bringing more investor rights back in), and that notes typically don't confer QSBS tax benefits because QSBS requires an equity holding period. Finally, he introduces 10 Capital's "3x and 3" note, which gives investors a sole-discretion redemption right at year three for 3x the original investment and then moves to a revenue share agreement, invites interested investors to join the deal-review group, and wraps by moving the audience into breakout rooms and sharing that the recording and event details will be sent afterward. ________________________________________________________________________ For more episodes from Investor Connect, please visit the site at: http://investorconnect.org Check out our other podcasts here: https://investorconnect.org/ For Investors check out: https://tencapital.group/investor-landing/ For Startups check out: https://tencapital.group/company-landing/ For eGuides check out: https:/_/tencapital.group/education/ For upcoming Events, check out https://tencapital.group/events/ For Feedback please contact info@tencapital.group Please follow, share, and leave a review. Music courtesy of Bensound.
Choosing the right business entity isn't just about LLC vs C-Corp — it's about aligning your structure with the type of investors you want, your risk tolerance, and your long-term goals. In this episode, we break down: How different investors think (and why most deals fail) Why entity structure impacts your ability to raise capital When to use LLC vs C-Corp (and why it depends) How to structure multiple entities to reduce risk Tax strategy insights, including QSBS and exit planning Most entrepreneurs ask, "What's the best structure?" — but the real question is: What structure fits your goals and your investors? If you want to raise capital, protect your downside, and build long-term value, this is a must-watch. Timestamps: 0:00 Why most businesses attract the wrong investors 1:45 Why entity structure actually matters 4:30 Different types of investors explained 8:15 The biggest mistake founders make 12:00 LLC vs C-Corp (what actually matters) 16:30 Why multiple entities reduce risk 20:45 Structuring for flexibility and exit 25:30 Tax strategy and QSBS explained 30:00 How to think about your structure going forward Connect with Erik Van Horn:
Upstart Collective officially opened its new home on the fifth floor of Big Pink — and it's a big deal for Portland's startup community. Plus: Governor Kotek signed SB 1507 (the QSBS tax), but her signing letter hints at a fix. ConductorOne rebrands to C1. And a YC alum in Vancouver, WA wants to freeze your brain and hook it up to the internet. CHAPTERS00:00 Oregon startup news07:00 Upstart Collective grand opening at Big Pink13:00 QSBS / SB 1507 20:00 ConductorOne rebrands to C123:00 Nectome — freezing brains and hooking them to the internet30:00 Secrets LINKShttps://doing.tools/ https://pitchmap-pnw.com/ https://pigsquad.com/ https://pigcon.pigsquad.com/ https://siliconflorist.com/2026/04/08/its-official-upstart-collective-grand-opening-ceremony-welcomes-startup- coworking-to-big-pink/ https://siliconflorist.com/2026/04/09/governor-kotek-signed-sb-1507-as-expected-but-she-also-said-something-ab out-qsbs-that-you-need-to-hear/ https://www.c1.ai/ https://nectome.com/ FIND RICK TUROCZY ON THE INTERNET AT…- https://patreon.com/turoczy- https://linkedin.com/in/turoczy- Portland Oregon startup news on Apple Podcasts https://podcasts.apple.com/us/podcast/portland-oregon-startup-news-silicon-florist/id1711294699- Portland Oregon startup news Spotify https://open.spotify.com/show/2cmLDH8wrPdNMS2qtTnhcy?si=H627wrGOTvStxxKWRlRGLQ- Startup Stories on Spotify https://open.spotify.com/show/1Tk7bbzaNYowGouI9ucKC3- Startup Stories on Apple Podcasts https://podcasts.apple.com/us/podcast/startup-stories-with-silicon-florist/id1849468494- https://bsky.app/profile/turoczy.bsky.social- https://siliconflorist.substack.com/- https://pdxslack.comABOUT SILICON FLORIST ----------For nearly two decades, Rick Turoczy has published Silicon Florist, a blog, newsletter, and podcast that covers entrepreneurs, founders, startups, entrepreneurship, tech, news, and events in the Portland, Oregon, startup community. Whether you're an aspiring entrepreneur, a startup or tech enthusiast, or simply intrigued by Portland's startup culture, Silicon Florist is your go-to source for the latest news, events, jobs, and opportunities in Portland Oregon's flourishing tech and startup scene. Join us in exploring the innovative world of startups in Portland, where creativity and collaboration meet.ABOUT RICK TUROCZY ----------Rick Turoczy has been working in, on, and around the Portland, Oregon, startup community for nearly 30 years. He has been recognized as one of the “OG”s of startup ecosystem building by the Kauffman Foundation. And he has been humbled by any number of opportunities to speak on stages from SXSW to INBOUND and from Kobe, Japan, to Muscat, Oman, including an opportunity to share his views on community building on the TEDxPortland stage (https://www.youtube.com/watch?v=Cj98mr_wUA0). All because of a blog. Weird.https://siliconflorist.com#pdx #portland #oregon #startup #entrepreneur
Today's guests are Alex Rubalcava and Paul Bricault of Amplify.LA, a pre-seed venture capital firm. In today's episode, Alex and Paul break down the opportunities and challenges AI is creating for both startups and investors. They discuss the changing economics of software, what makes an AI company defensible, where investors are finding opportunity in frontier sectors, and why speed matters more than ever in early-stage investing. To close, they explore startup pivots and the tax advantages of QSBS. (0:00) Starts (1:27) Introducing Alex and Paul (2:02) Public software companies & AI (5:13) Amplify LA background and partnership formation (7:34) AI use cases in portfolio companies (15:08) AI's impact on the job market (30:31) AI's impact on investment opportunities at the pre-seed stage (41:02) Aerospace sector opportunities (44:32) Successful startup pivots (50:18) Liquidity in VC (55:28) QSBS impact ----- Sponsor: Alpha Architect - To learn more about CAOS, read the Fund's prospectus and important information, visit funds.alphaarchitect.com/caos ----- Follow Meb on X, LinkedIn and YouTube For detailed show notes, click here To learn more about our funds and follow us, subscribe to our mailing list or visit us at cambriainvestments.com ----- Follow The Idea Farm: X | LinkedIn | Instagram | TikTok ----- Interested in sponsoring the show? Email us at Feedback@TheMebFaberShow.com ----- Past guests include Ed Thorp, Richard Thaler, Jeremy Grantham, Joel Greenblatt, Campbell Harvey, Ivy Zelman, Kathryn Kaminski, Jason Calacanis, Whitney Baker, Aswath Damodaran, Howard Marks, Tom Barton, and many more. ----- Meb's invested in some awesome startups that have passed along discounts to our listeners. Check them out here! -----Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Learn more about your ad choices. Visit megaphone.fm/adchoices
The party always ends — and Meb Faber, one of the most data-driven voices in global investing, says the evidence is now undeniable that the decade-long US equity dominance is giving way to something very different.SUMMARYOn this episode of Raise Your Average, hosts Pierre Daillie and Mike Philbrick sit down with Meb Faber — co-founder and CIO of Cambria Investment Management, prolific researcher, and host of The Meb Faber Show — for a wide-ranging conversation about what investors and financial advisors must rethink as the rules of the game quietly change beneath their feet.With US equity concentration at historic extremes, inflation proving stickier than expected, and geopolitical disorder accelerating structural shifts already underway, Meb makes the case that the era of a US-heavy 60/40 portfolio solving everything is in the rearview mirror. He challenges the deeply ingrained recency bias that has left most North American investors dangerously underweight in international equities and real assets — and explains what the data actually says about where opportunity is emerging.The conversation moves from big-picture regime change into highly practical territory: how to build a portfolio that survives behaviorally, not just mathematically; how to think about concentrated, low-basis positions and the tax traps hiding inside the gains of the last 15 years; and why "tax alpha" may be the most overlooked and underutilized edge in wealth management today. Meb also shares how he's deploying AI in his own practice — including a custom-trained GPT built on his entire body of work — and what advisors should be borrowing from that playbook right now.⏱️ CHAPTERS00:00 — Welcome & banter: tacos, spicy food, and market chaos 08:00 — Meb joins; framing the moment: Venezuela to tariffs to Iran 13:00 — A regime change? Dissecting the end of the 40-year bull run 15:00 — The bull market in diversification: foreign markets doing 30%+ while the S&P stalls 17:00 — What advisors are underweight: ex-US equities and real assets 20:00 — How to explain a generational shift to clients without jargon 24:00 — Global diversification: the evidence from 15 famous portfolios 27:00 — The 20% annual spread problem and why tracking error breaks investors 30:00 — Portfolio vulnerabilities in the cap-weighted US-dominant model 31:00 — Opportunities: global value, small cap, fixed income niches, real assets 35:00 — The "fat" portfolio: three ingredients every investor needs 40:00 — Utilities, dividends, and the tortoise-vs-hare reversal 44:00 — Behavioral investing: why systematic strategies exist 48:00 — The concentrated position trap: identity, emotion, and the sell decision 51:00 — Systematic rebalancing: lessons from Cambria's early days 53:00 — "The easy money's been made" — market phrases Meb despises 55:00 — Deep value and what it takes to be a missionary, not a mercenary 58:00 — The best active managers and why they always close the door at the top 1:00:00 — When the penthouse becomes the outhouse 1:04:00 — The Groucho Marx rule: would you buy what you already own? 1:10:00 — Drawdown, pain tolerance, and the real test of a portfolio 1:17:00 — Concentrated low-basis positions: the tax trap hiding in plain sight 1:19:00 — 100 years of stock data: what the best-performing stocks actually returned 1:22:00 — Tax strategies: 351 exchanges, direct indexing, QSBS, and box spreads 1:27:00 — AI in practice: Meb's custom ChatGPT and how advisors should use AI now 1:30:00 — Behavioral AI: what happens when the bot knows you better than you do 1:32:00 — Closing thoughts: raising your average in a noisier, more complex world #MebFaber #CambriaInvestments #GlobalDiversification #PortfolioConstruction #ValueInvesting #TrendFollowing #6040Portfolio #TaxAlpha #ConcentratedPositions #DirectIndexing #RealAssets #InternationalStocks #RegimeChange #FinancialAdvisor #WealthManagement #InvestingStrategy #RaiseYourAverage #AIInvesting #BehavioralFinance #LongTermInvesting #ETFinvesting #SmartBeta #FactorInvesting #MarketOutlook2026 #AdvisorAnalyst
This week on Swimming with Allocators, Earnest and Alexa welcome Charlotte Zhang, Senior Portfolio Manager at Inatai Foundation. Charlotte shares her unconventional path from tech investment banking into LP life, her work at Inatai Foundation, and how she evaluates fund managers across asset classes. She explains Inatai's mission-driven, endowment-style strategy centered on efficiency, innovation, and impact, and how they manage capital for other aligned foundations. She also shares how generalist allocators run thematic research sprints, why they avoid rigid asset class buckets, and how they think about biotech, crossover, and platform value creation. For venture managers, she outlines what LPs look for: real differentiation rooted in an unmet need, some form of specialization, strong networks and early access, and the “four Ps” all anchored in people with integrity and learning agility. Also, don't miss Michael Podolny as he explains how Sidley's emerging companies practice is increasingly busy as AI-driven and globally ambitious startups seek sophisticated, full‑lifecycle legal and tax advice from day one, with a particular focus on planning early to maximize QSBS tax benefits and founder outcomes. Highlights from this week's conversation include: Charlotte's Path From Banking to Allocator (1:12) Inatai's Mission and Investment Focus On Racial Justice (6:12) Investment Strategy and The “Three I's” (Inefficiency, Innovation, Impact) (7:54) Managing Multiple Asset Classes Wwith Thematic Research (12:23) How Sidley Supports Sophisticated, AI-Driven Startups and QSBS Planning (18:25) What Emerging Managers Get Wrong With Foundations and OCIOs (23:39) Why Specialization and Differentiation Matter in Venture (24:09) Charlotte's Take on Venture Versus NASDAQ and Top-Decile Returns (36:38) Charlotte's Immigrant Background and Empathy or Underdogs (41:19) Inatai Foundation is a 501(c)(4) philanthropy seeking to transform the balance of power to ensure equity and racial justice across Washington state and beyond. The organization is accountable to leaders and organizations building power in racially diverse communities in Washington state and seeks to primarily fund community based organizations led by people of color. With a team based throughout Washington, it works to advance four distinct areas of work: relationship building, policy and advocacy, investment management, and grantmaking. Learn more at www.inatai.org. Inatai Investment Management Company is guided by the belief that successful investing is about more than money. The organization leverages extensive expertise, deep resources, nimble governance structure, and knowledgeable investment managers to generate long-term, sustainable returns for Inatai Foundation and other mission-aligned organizations, using a cost-sharing model. The investment options chosen are determined not just for their potential for growth but for how they support our values and the positive impact they may achieve for the world. Our goal is to become a proactive, community-driven force for change in capital markets and in the investment sector at large. Learn more at www.inatai.partners. Sidley Austin LLP is a premier global law firm with a dedicated Venture Funds practice, advising top venture capital firms, institutional investors, and private equity sponsors on fund formation, investment structuring, and regulatory compliance. With deep expertise across private markets, Sidley provides strategic legal counsel to help funds scale effectively. Learn more at sidley.com. Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies. The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices
BRADY WELLER discusses the intricacies of QSBS rollovers, including eligibility, timing, and strategic planning for founders and investors. The goal is to help the listener maximize tax benefits and navigate the legal complexities of this powerful tool. https://youtu.be/gvQ0ZskvWVI QSBS, tax exemption, startup founders, rollover, legal structuring, investment strategy, tax planning, startup exit, C corporation, Key Topics QSBS eligibility and benefits Challenges in executing rollovers Legal and tax considerations for founders Timing and risk management in rollovers Strategic structuring for maximum benefit “QSBS ROLLOVERS” Sound Bites “60 days is a very short window for founders.” “Rollover continues your holding period clock.” “Partial rollovers are common for founders.” Chapters 00:00 Understanding QSBS and Its Benefits 03:07 Challenges for Founders in QSBS Compliance 05:54 Advising Founders on QSBS Rollovers 08:57 Structuring New Ventures for QSBS Eligibility 12:00 Navigating QSBS for Tech and Non-Tech Founders 14:54 Investor Considerations in QSBS Transactions 17:46 State-Specific QSBS Regulations and Planning 20:57 Future of QSBS and Strategic Planning Resources Brady Weller on LinkedIn qsbsrollover.com qsbsreference.com Frazer Rice and Michael Arlein discuss the nuts and bolts of 1202 QSBS Features for Founders Guest links LinkedIn Transcript Frazer Rice (00:01.314)Welcome aboard, Brady. Brady Weller (QSBS Rollover) (00:03.043)Hey, Frazer, thanks for having me. Frazer Rice (00:04.738)Well, you are the nice compliment to a piece I just did with Michael Arlene on QSBS. We covered some of the nuts and bolts around 1202. You come at it from a little bit different angle. It’s usually where people, founders especially, have issues sort of complying with things like the three and five year rule. And otherwise really maximizing the capability of the rollover and the tax significance for it. Tell us a little bit about who benefits and what you do here. Brady Weller (QSBS Rollover) (00:35.107)Yeah, QSBS is. by far the biggest tax exemption available to individual taxpayers in the U.S. So it’s been something that hasn’t been up. I should say there’s not a massive advisory network around it. So it’s not something that’s been taken advantage of, I think, to its full scope. Michael, who you had on recently, is a top trust and estate planner for founders of companies around QSBS. The specific problem that QSBS rollover solve is for a shareholder of an early stage company. Most often founders or very early investors, say, maybe series A or earlier shareholders. It’s an incentive to basically hold your stock for a quote unquote long time. In this sense, that means, you know, now under some new rules, basically three to five plus years. It’s a tax exemption available to folks who hold their stock for at least five years. Then they can exclude from federal income tax now up to $15 million of gains when they sell that stock. So you have to be a shareholder in an early stage C corporation, early stage company. Frazer Rice (01:50.616).Those founders before three to five years are trying to figure out how to use this tool. What are the challenges in making sure they don’t blow up the transaction by transferring something poorly. Or having their company grow too large or have too much cash or those types of things? Maybe list out a little bit some of the challenges that are out there that that a founder needs to be aware of. Brady Weller (QSBS Rollover) (02:22.509).Yeah. So we don’t have to constantly caveat. I’ll mainly talk as though we’re speaking about the pre July 5th, 2025 rules for QSPS. Anything, any stock issued after that date, middle of last year. is under a slightly different set of rules. They are more expanded rules, but I’ll speak to this sort of from those old rules. And so the old rules state that you have to hold your stock for at least five years. And if you do, you can exclude a large portion from federal income tax, usually $10 million for founders. But if you don’t hold the stock for five years, your only option is to take the cash from that sale. For example, say you sell stock at year three or year four, and purchase new QSBS eligible stock with that cash within 60 days. So it’s sort of like the 1031 exchange. Folks maybe are more familiar with real estate property exchanges. Its sort of like a 1031 exchange for stock. So you take the cash and you purchase a like kind quote unquote asset with it. Now the challenge with that is 60 days is not a very long time. And when you’re a founder of a company who just went through liquidity. You just got your deal done and the whirlwind that that is. Now you’re dealing maybe in a post liquidity world. You’re maybe running another team at the acquirer or you’re otherwise involved. 60 days is not a long time to be able to find and diligence a new opportunity. . It’s just not feasible. Especially for founders to use that cash to say buy stock in someone else’s company. It just doesn’t make sense. Like risk adjusted, I suppose. Frazer Rice (04:05.579)No, it’s a miracle that your company did great. Now you have to go and find another miracle and make it work within 60 days. It’s crazy. Brady Weller (QSBS Rollover) (04:10.143).That that’s the biggest that’s probably the biggest barrier to executing them. For the longest time there just weren’t a lot of people. They hadn’t come alongside founders to help advise them on structured ways that they could do these rollovers. Yeah, the options are risky. It’s like take your money and invest it in Dave’s startup in San Francisco. He’s going to lose your money. So that may be what you want to do with that money. To keep your risk profile sort of moving. But that’s not tax planning in any way. Right. To make that decision just to save on federal income tax might not be the best way to use your rollover. So we’ve seen it much more for angel investors, something that they might use. People who want to maybe have a lot of deal flow. A lot of investment opportunities in front of them. But they want to keep that risk profile moving. I’d say timing and risk are the two biggest challenges when you’re trying to execute a rollover. Frazer Rice (05:13.805).As a detail on that, you’ve got your company. You’ve got $10 million coming to you. Hopefully tax free, similar to a 1031. You don’t have to go into one company, you could go into a basket of companies. Brady Weller (QSBS Rollover) (05:28.579).Yeah, you could take the cash, say you make $10 million from a sale. You could pay taxes on $3 million of it, assuming you haven’t hit your five year requirement. Then, you could roll over the other seven in various other deals. You could put it all into one new company. What the rollover actually does is it continues your holding period clock from the last stock. So if you held for three years in your original company stock, You sell. You’re able to reinvest those proceeds within 60 days. It continues your holding period. Once you’re beyond a combined five the next liquidity event in the second company. Now you have proper seasoning on your shares, for lack of a better word, and then you can sell them under the QSPS exemption. Frazer Rice (06:17.143)So, this gets to what you do on a day-to-day basis. So a founder comes to you and says, all right, I’ve got this situation I think that’s coming. And I need some advice. You’re sort of letting them know what’s happening here. How do you advise them, in a sense, whether it’s through your company or even as a general matter? Do you have a suite of other founders and companies that are out there? And then… Maybe also similar to a 1031, is there sort of an intermediary function that needs to happen in order for the asset or the cash to go into sort of a, for lack of word, like an escrow account to then be deployed correctly into the eligible next company so that you keep that period going. Brady Weller (QSBS Rollover) (06:50.713)Boom. Brady Weller (QSBS Rollover) (07:05.839)That’s a good question. It’s not as formalized as the, you know, in terms of the 1031 world where there’s sort of a designated intermediary and that’s sort of required step in the process. This is very much the wire goes into your checking account for the sale of company A stock. Frazer Rice (07:11.703)Mm-hmm. Brady Weller (QSBS Rollover) (07:22.281)You send a wire back out to purchase stock in company B. When someone comes to us and is looking for guidance on how to do a rollover, sometimes they’ve talked to tax or trust in state attorneys already, or maybe they’re CPA. And there are maybe 50 folks in the US who have, I’d say, Frazer Rice (07:37.463)Sure. Brady Weller (QSBS Rollover) (07:45.07)I call it advanced QSPS planning knowledge, which is they have the trust planning strategies, rollover knowledge, all of these things that sort of at their disposal that they can speak to, but it’s a very small network. so our firm is actually the only non-CPA non-law firm in the country that deals directly with founders on these. And so we ended up kind of playing quarterback, connecting them with the right attorneys, maybe the right CPA, if they don’t have one to make sure that the team is sort of assembled. You know, because the risk profile of taking your money and investing in someone else’s company typically doesn’t align with most founders’ interests at that time, the service that we provide is helping them to roll that money into a new startup of their own. We think these founder-led rollovers where the founder or the shareholder who sold their original stock can now direct the proceeds into a new entity that they own and control. It’s a really great way to execute this. It gives the shareholder, the founder the optimal amount of flexibility and control over the proceeds over time. So they can handle their own risk profile. Frazer Rice (08:57.921)So for the founder who built their business originally, they sell it and you’re sort of with them along the way to roll it over into another founder led situation. Are there any mechanics that you help with to sort of ensure that that takes place correctly? There’s so many, it seems like so many tiger traps along the way that you can stick your foot in and you did every, your intent was there, but maybe you did something weird or incorrect. Brady Weller (QSBS Rollover) (09:26.617)Yeah. Frazer Rice (09:26.721)Maybe a better way to ask this question is what are the things in that receiving new QSBS rollover do you want to see or a founder should make sure they have in place before they go ahead and pull the trigger? Brady Weller (QSBS Rollover) (09:41.904)We want to make sure it’s a C corporation. First of all, a lot of times when founders start their first companies, they just, you know, incorporate an LLC somewhere and start doing business. A lot of times there’s not even, maybe there’s, you know, two or $3,000 transferred to a checking account, you know, from their personal to their checking. That’s how you start most businesses. But when you’re, when you’re starting a rollover business, we have to see a couple other things. One is we want to make sure it’s a C corp from day one. Frazer Rice (09:58.989)Right. Brady Weller (QSBS Rollover) (10:09.123)You know, it’s okay if it’s a single owner C Corp where the founders, the, you know, only board member, only director. It’s, you know, it’s your entity. That’s fine. but we also want to see a purchase agreement, some kind of stock purchase agreement. So you can’t just transfer money from your chase savings account where the wire landed to the new business account and, know, go on about, about the business. we want to see a stock purchase agreement. And so some of those agreements, and the optimal way to do those for sort of the, the, the long run. Sometimes, we would obviously we have our template docs in ways that we might advise to do it. But very often we refer that out to legal counsel and coordinate there to make sure that just all the purchase agreements and governance docs and those types of things are in a good place. You know, it’s really making sure we have the purchase agreements and that the money gets moved to the corporate bank account, the new business bank account within 60 days. It’s really not a long period of time. And we run into a lot of situations where If someone’s not kind of quarterbacking the process, deadlines get away quickly and then administrative issues with a bank might push you beyond the 60 day window. We’ve seen that a few times and it can obviously cost you a lot of money. Frazer Rice (11:24.468)The, when you get to a point where the next business that this is going into, often the qualifications of being a QSBS eligible business can be a little bit murky. I’m thinking healthcare for instance, where like a hospital or that type of thing would traditionally probably not be a QSBS situation, but a healthcare service provider or a biotech company or something like that is. Brady Weller (QSBS Rollover) (11:46.937)Yeah. Frazer Rice (11:51.029)Do you help founders think about that? in many ways, there’s sort of the which came first, the idea for the company or the company itself. How do you make sure people stay on all fours on that front? Brady Weller (QSBS Rollover) (12:00.56)Yeah. Yeah, I if you build a startup before, know that the ideas in the early stage sometimes are extremely malleable. And when you start testing things in the market, the business very often changes. You know, we majority work with tech founders and that’s not because, you know, QSBS is well suited for tech. I think a lot of people think that to be QSBS, to be a technology company. That’s not true. It’s just that we most often see QSBS. We run into people who are knowledgeable about QSBS in the venture space. So venture backed start up, like traditional startup businesses, has 80 % plus of those companies are tech businesses. And then the other 20 % is manufacturing, biotech, life science, e-commerce, those types of things. But majority of people that we do these transaction with are in tech. And so by virtue of that, their rollover business ends up being, most of the time, ideas that they have are tech adjacent. So that’s a great place to be. I’d say some things to avoid. What we hear often people coming to us wanting to roll over into real estate in some way or another. And there are ways that the business that you start as part of a QSPS roll over can hold real estate assets long term, depending on the business type. But you have to be really careful there not to, in the eyes of the IRS, look like a real estate holding company or have too much of your assets tied up in sort of like passive real estate holdings. And so I’d say that’s the murkiest stuff that we run into. Brady Weller (QSBS Rollover) (13:37.822).Most of the businesses that we are helping founders start and grow as part of a QSPS rollover are B2B or B2C tech. Either web applications or mobile applications, e-commerce stores. We have a few hardware sort of based companies or like very physical product based companies as well. Frazer Rice (13:58.431)For a lot of tech founders, the idea of taking some money off the table is important. And I would think that maybe partial QSPS situations come up. This isn’t an all or nothing thing. You can take some money off the table and then allocate other parts, maybe half off and then the other half you can roll into the next company. Brady Weller (QSBS Rollover) (14:14.137)Yeah. Brady Weller (QSBS Rollover) (14:18.798)I’d say an extremely common situation that we see is maybe a founder. in New York who is raising maybe a Series B, call it a 50 or $60 million Series B. We saw a lot of these size rounds with the AI kind of boom happening and might be an opportunity to take, you know, four to $6 million off the table as secondary at that stage in the company’s growth. so you have this founder who just got $5 million wired to their bank account, maybe their first money. They’ve been renting in a condo or apartment in the city and they’re still very much like in high growth stage with company so they don’t have a lot of bandwidth to run a new business. And so they’ll really try and de-risk themselves. That is, maybe pay taxes on a million, a million and a half, give themselves a cushion right away, maybe buy a condo or you know whatever, stabilize their life just a bit and roll over the other four, three and a half million, you know, and manage a project on the side that way. That’s a really common situation we see. Frazer Rice (15:19.624)For investors who are invested in a lot of different things and maybe you know, they’ve got six or seven companies that are QSBS eligible and they are sort of rolling the dice on that and sort of picking and choosing which one should go into which that type of thing What’s different about it from an investor standpoint than from an operator standpoint? Brady Weller (QSBS Rollover) (15:43.758)Yeah, I think the biggest thing investors have to pay attention to is if you receive a distribution that isn’t QSPS eligible because of holding period, you cannot just take that money and invest it back into a venture fund. and call that a rollover. The money can go into a venture fund, but that capital also has to be called and deployed into, an investment from that fund. Meaning you can’t just invest in the, in the partnership at the partnership level in a venture fund and it’s sit there undeployed and be eligible for QSBS. It actually has to be fully deployed into target, target opportunities within 60 days. So that’s something that I think that we’ve run into a couple of times with, with investors is they think, I’ll just, know, Fund2 is open at, you know, XYZ firm. I’ll just roll the money over there. But it does have to be deployed still within that 60 day window. So that’s something that we hear a lot of. You know, if you’re an investor, I would keep, you know, you don’t always have the perfect deal ready at the right time. But keeping good relationships with the founders that… you’re partnering with, you know, you never know when someone might be able to open up a tranche on the side or sell some secondary to you. if you’re trying to still get access to that deal sort of outside of a normal round. Frazer Rice (17:07.445)So for the companies that are in your orbit, obviously you’re probably checking in saying, hey, you didn’t do anything to blow up your QSBS status. But for the companies that aren’t that way, and let’s say you’re a founder and you’ve got a nice situation where you’re able to take some money off the table and maybe put it into. one of the things that your friends put together or something like that. How do you think about a checklist or what are the questions to ask to make sure that the recipient investor or recipient of the investment is QSBS eligible and will sort of stick to it? Brady Weller (QSBS Rollover) (17:46.48)Yeah, you want to ensure first that the company is small enough. so under the old rules that I mentioned, the company would have to have less than $50 million of gross assets. A really great proxy for that is just how much has that company raised? You know, if you’re trying to invest in a company and they’ve raised $120 million, it’s very likely that they have at some point blown the asset test and they’re not issuing QSPS anymore. It’s very, it’s not always, but it’s very possible. A lot of people confuse that test for valuation. which is a mistake, you could have a billion dollar company in terms of market value, you know, with only 20 or 25 million dollars worth of assets on the balance sheet. It is possible, especially in some of these high multiple high growth tech businesses. And so, yeah, not confusing valuation with gross assets is one thing to pay attention to. the other is ensuring just that the company is a C corp, especially for early stage investors. I’m talking like first money in, maybe before, you know, pre seed or pre seed, would say, ensuring that the right structuring is in place such that, know, you’re getting stock issued directly from a C corporation at that time you’re investing. So I would say that’s something to worry about more if you’re, you know, an angel. who does a lot of sort of direct sourcing of deals and you’re not going through a fund. Most of the time, if someone’s raised capital directly from a venture fund, all the paperwork and things that you’re going to look for as far as QSPS are going to be in place, because most VCs are pretty well acquainted at this point with, hey, let’s make sure this is eligible before we get in here. Frazer Rice (19:27.913)Right. And just to distinguish, an LLC that elects to be taxed as a C Corp versus a C Corp, C Corp, is there any distinction there for our listeners? Brady Weller (QSBS Rollover) (19:39.673)Yes. Generally, we would say as long as the LLC has made that C-Corp election before issuing more at that stage, guess, membership units of stock, as long as they’ve made that C-Corp election prior to issuing the stock, then we feel generally good about it. But yeah, an LLC, it’s an entity structure whose default taxation is as a pass-through, but an LLC can also be taxed as a C-Corp and can issue quote unquote QSBS eligible shares. or units as well, so it is possible. Frazer Rice (20:12.683)I was gonna say, so for the listeners out there, C-Corp doesn’t just mean C-Corp, but the real operative language is that it’s taxed as a C-Corp component, and that should be part of your checklist as you go down the list of companies to potentially roll into. So for those people who aren’t exactly founders, but maybe are investors or otherwise part of businesses that they’ve been included in, et cetera. Those non-venture-backed businesses, what are the opportunities there for QSBS and then the ability to roll it over into other things? Brady Weller (QSBS Rollover) (20:48.708)Yeah, I would say it’s very rare that we see a non-venture-backed business in between the coasts, I’ll say, right? Like not one of these like kind of like call them coastal elite tech businesses. I’m talking about your like legacy family business in, you know, North Carolina. Frazer Rice (20:59.488)I mean… Brady Weller (QSBS Rollover) (21:11.856)Most of the time we’re going to see those as pass-throughs or partnerships, maybe like an S-Corp. You would see that type of structure and those businesses, while they could be amazing businesses, the interest in them isn’t QSPS eligible because it has to be issued from a C-Corporation. Most of the time, the planning opportunity we see with those types of businesses is around the time of maybe a generational transition or other type of transition planning where Maybe the children take over from the parents and they establish a plan. Hey, we’re going to take it over, but we want to plan to sell maybe the next five to seven years. I hear this a lot. And opportunity. If you are in an industry in a sector where stock sales are common in the industry for exiting the businesses, changing, electing to be treated as a C Corp or restructuring to a C Corporation from one of those pass through structures is an opportunity because you could sort of reorganize, reissue stock, now start your QSBS five year time clock. And, you know, hopefully the business keeps doing well and you can have that exit opportunity down the line. And at that point, take advantage of QSBS. Again, the thing you want to pay attention to is that you actually be able to do a stock sale at that time because QSBS requires a sale of stock, not an asset sale. And so that’s a really important distinction. So make sure either that you’re in an industry where that’s common or you’re working with counsel who understands what you’re trying to accomplish before you make those decisions about how you’re setting your entity up at that stage. Frazer Rice (22:41.353)Right. Frazer Rice (22:56.758)I just have a comment for me with the passage of the new law that we sort of alluded to where previously you really didn’t start thinking about this until fully five years. The new law, people can start thinking about it within three. You get 50 % of the benefit of the exclusion at three years. Brady Weller (QSBS Rollover) (23:08.282)Mm-hmm. Frazer Rice (23:15.21)And I’ve run into people where three years suddenly seems like a short amount of time, whereas five years, I think everyone was sort of like, we’ll get there eventually. you know, they’re they’re they’re fighting for their survival anyway. And if that happens to work terrific in this case, I think that the law moving the timeline up a little bit has had an interesting impact on those conversion discussions, because I think people are now starting to say, hey, you know what? I can get to three years. And, you know, with the speed at the and the rate at which things change at this point, it’s much more realistic than I think it might have been going back in time. Brady Weller (QSBS Rollover) (23:50.896)And if you have a stable business where you feel comfortable making projections, say three years out, so to what that business could look like at that time, it’s really becoming more common now to do what you’re calling like choice of entity studies, right? So working with someone who can model out with the difference in taxation, both at the company level and at the point of. Frazer Rice (24:05.482)Mm-hmm. Brady Weller (QSBS Rollover) (24:15.276)selling stock, what the optimal structure may be depending on your time horizon tax it, your expectations for growth or lack thereof. So that’s something that some valuation firms, business advisories, some law firms or CPA tax advisories may be able to do. If you’re in that situation, you’re trying to figure out, hey, what’s the math look like based on my baseline assumptions of what this business will be and can help you sort of make those decisions about how to plan. over the next three to seven years. Frazer Rice (24:47.402)As part of that reorganization too, I’ve talked to a few people who are in, let’s call it personality-based businesses, whether they’re podcasters or influencers or other types of things that are a little bit adjacent to maybe typical software companies. And I’ve brought up the notion that you may be disqualified now, but you may have a future growth opportunity within your business to make it fall more in line with a QSBS-defined business. And so, you if you’ve got the time and the ability and it makes a business sense, it may make sense to start thinking about either sectioning that off or developing that business line for something a little bit later on. Brady Weller (QSBS Rollover) (25:27.95)Yeah, being strategic about where those adjacent businesses, how they’re structured and where they’re built. And I mean, where like in terms of a legal entity level sense, I’m thinking about, for instance, several golf YouTubers, make a lot of golf content online, but now they’re announcing partnerships to, you know, design clothing, you know, have their own clothing line, or maybe they’ve entered a, a joint venture with a golf club maker or maybe an emerging brand and they’re taking equity. Frazer Rice (25:41.983)Mm-hmm. Brady Weller (QSBS Rollover) (25:57.826)Those are really interesting options and I think that you still have the opportunity to leverage your personal brand to grow that business but separating them out so that you know your reliance on your personal brand doesn’t ruin QSBS. That’s actually getting to one of the rules around qualified small business stock which is that the companies can’t be based on the skill or reputation of a single person. And so that’s when we think about Frazer Rice (26:24.938)Mm-hmm. Brady Weller (QSBS Rollover) (26:27.632)Like entertainers, athletes, social media personalities. MrBeast, for instance, couldn’t sell MrBeast, the YouTube channel necessarily, as QSBS eligible interest because of that rule more than likely. And that’s obviously a broad brush, paying attention to where you hold your business interests is important for this if you’re in that space. Frazer Rice (26:53.5)Any state thoughts? I know California QSBS is uncoupled from the federal QSBS and New York threatened it and apparently that got knocked down. New Jersey just coupled with the federal government so that people weren’t scared away from doing that. How does that figure into your analysis? Brady Weller (QSBS Rollover) (27:04.304)you Yeah. Brady Weller (QSBS Rollover) (27:12.784)It’s sort of a battle of the coast. It’s like which coast of the United States is going to be most investor and founder friendly with relation to these things. Yeah, because California hasn’t followed it for a long time. Oregon and Washington state are close behind there. And then we have the sort of somewhat the opposite happening on the East Coast. So as an East Coast guy, I hope it becomes a hub. But yeah, there is some sort of. Frazer Rice (27:19.528)Right. Brady Weller (QSBS Rollover) (27:36.388)you know, state and local tax planning, strategic planning that you might be able to do if you have the foresight and, you know, the right data to determine where you might become a resident or taxpayer prior to an exit. You might talk with a. assault attorney or assault advisor state and local tax is usually tax advisors CPAs or or tax attorneys who can help you think through Hey, does it make a difference whether or not I move from California to Texas? What does that look like for my family? What does that look like for my post-tax exit situation? because where the company is headquartered, as long as it’s in the United States, doesn’t matter for QSPS, just has to be a domestic USC corporation. And so remembering that QSPS is fundamentally an individual taxpayer incentive means that regardless of where the shareholders are located, you’re gonna be beholden to that specific state of where you live and their roles around QSPS. Frazer Rice (28:36.906)Terrific stuff. Brady, we’re winding down here. How do people find you and your company and any sort of parting thoughts? Brady Weller (QSBS Rollover) (28:44.516)Yeah, I’m personally very active on LinkedIn. So you can find me there, Brady Weller and our website, qsbsrollover.com. We also have a sort of an open source QSBS advisory referral site called qsbsreference.com. And so you can find us at either of those places. We’d be happy to help you out and point you in the right direction. Frazer Rice (29:05.13)Brady, thanks for being on. Brady Weller (QSBS Rollover) (29:06.874)Thanks, Frazier, appreciate it. Keywords QSBS, tax exemption, startup founders, rollover, legal structuring, investment strategy, tax planning, startup exit, C corporation, legal advice Titles Mastering QSBS Rollovers: Strategies for Founders and Investors The Ultimate Guide to QSBS Tax Exemptions and Rollovers https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/
This week: Beaverton Startup Challenge deadline, All Raise's VC diversity survey, Dominic Kuklawood on The Awkward Handshake, my Prosperity Council response on SB 1507, the Yex Labs fiscal impact model that shows Oregon could lose a billion dollars over 10 years from QSBS taxation, and Charles Voloshin's Control Your Persona manifesto. Plus secrets.Chapters00:00 Intro00:27 Beaverton Startup Challenge — applications due01:48 All Raise survey 02:41 Dominic Kuklawood on The Awkward Handshake04:10 SB 1507 & the Prosperity Council response07:35 Yex Labs QSBS fiscal impact model — Monte Carlo simulation13:55 Control Your Persona16:20 SecretsLinks- Beaverton Startup Challenge: https://www.oregonstartupcenter.org/beaverton-startup-challenge-applications-open- All Raise: https://www.allraise.org/- Calagator: https://calagator.org/events- Portland Startup Events: https://lu.ma/PortlandStartupEvents- The Awkward Handshake podcast: https://www.youtube.com/watch?v=fjpnwIgg0K0- My Prosperity Council response: https://siliconflorist.com/2026/03/23/my-response-to-the-oregon-governors-prosperity-council/- QSBS fiscal impact model: https://www.yex.ai/- Control Your Persona manifesto (Soqratic / Charles Voloshin): https://controlyourpersona.org/FIND RICK TUROCZY ON THE INTERNET AT…- https://patreon.com/turoczy- https://linkedin.com/in/turoczy- Portland Oregon startup news on Apple Podcasts https://podcasts.apple.com/us/podcast/portland-oregon-startup-news-silicon-florist/id1711294699- Portland Oregon startup news Spotify https://open.spotify.com/show/2cmLDH8wrPdNMS2qtTnhcy?si=H627wrGOTvStxxKWRlRGLQ- Startup Stories on Spotify https://open.spotify.com/show/1Tk7bbzaNYowGouI9ucKC3- Startup Stories on Apple Podcasts https://podcasts.apple.com/us/podcast/startup-stories-with-silicon-florist/id1849468494- The Long Con on Apple Podcasts https://podcasts.apple.com/us/podcast/the-long-con/id1810923457- The Long Con on Spotify https://open.spotify.com/show/48oglyT5JNKxVH5lnWTYKA- https://bsky.app/profile/turoczy.bsky.social- https://siliconflorist.substack.com/- https://pdxslack.comABOUT SILICON FLORIST ----------For nearly two decades, Rick Turoczy has published Silicon Florist, a blog, newsletter, and podcast that covers entrepreneurs, founders, startups, entrepreneurship, tech, news, and events in the Portland, Oregon, startup community. Whether you're an aspiring entrepreneur, a startup or tech enthusiast, or simply intrigued by Portland's startup culture, Silicon Florist is your go-to source for the latest news, events, jobs, and opportunities in Portland Oregon's flourishing tech and startup scene. Join us in exploring the innovative world of startups in Portland, where creativity and collaboration meet.ABOUT RICK TUROCZY ----------Rick Turoczy has been working in, on, and around the Portland, Oregon, startup community for nearly 30 years. He has been recognized as one of the “OG”s of startup ecosystem building by the Kauffman Foundation. And he has been humbled by any number of opportunities to speak on stages from SXSW to INBOUND and from Kobe, Japan, to Muscat, Oman, including an opportunity to share his views on community building on the TEDxPortland stage (https://www.youtube.com/watch?v=Cj98mr_wUA0). All because of a blog. Weird.https://siliconflorist.com#pdx #portland #oregon #startup #entrepreneur
SMALL BUSINESS FINANCE– Business Tax, Financial Basics, Money Mindset, Tax Deductions
Most business owners think the government only takes money. In reality, there are billions in grants, tax credits, and incentives available in 2026. This episode breaks down state incentives, federal tax credits like WOTC and Section 179, and powerful strategies like QSBS, real estate depreciation, and defined benefit plans. You'll learn how to stack credits, apply before hiring or expanding, and document everything properly. These programs are not loopholes. They are written into the tax code to reward business owners who create jobs and invest in growth. If you want to reduce your tax bill legally and stop leaving money on the table, this episode shows you where to start. Next Steps: ➡️ Overpaying your CPA and the IRS? Learn how to stop it in this free training: https://go.phillipsbusinessgroup.com/registration
This week: Silicon Forest Tech Summit 2026 recap, Eclypsium raises another $25M (bringing their total past $110M), Seattle's OneCourt wins SXSW Pitch with a Portland Trail Blazers connection, PIE alum James McDermott is back with a new AI startup called Antfly, and in Secrets — why Oregon's QSBS tax policy is an existential threat to the startup ecosystem.⏱️ CHAPTERS (estimated — adjust to actual timecodes)0:00 Governor's Prosperity Council Survey (FILL IT OUT)4:55 Silicon Forest Tech Summit 2026 Recap 10:00 Eclypsium Raises $25M (Total: $110M+)15:30 OneCourt Wins SXSW Pitch (Blazers Connection)19:00 Antfly: PIE Alum James McDermott's New AI Startup25:17 Secrets
Host Gary J. Ross talks with Daniel DeWolf, Co-chair of the VC/EC practice at Mintz Levin and adjunct professor at NYU School of Law, about the practice of venture capital funds warehousing investments. Among the topics Gary and Daniel cover are the reasons fund managers warehouse investments; various structures used for warehousing; disclosure considerations; conflicts of interest; valuation issues; SEC guidance on warehousing and maintaining the venture capital fund adviser exemption for ERAs; and the impact of warehousing on eligibility for the qualified small business stock (QSBS) tax exemption.
QSBS can unlock meaningful benefits under Section 1202. Hear a practical discussion on timing, eligibility, and the details that can drive outcomes.
The week started great — Silicon Forest Tech Summit lineup, Agility's rebrand, SBIR grants returning, Portland Dining Month — and then Oregon's QSBS legislation landed on the governor's desk. Let's break down what qualified small business stock exclusion meant for Oregon founders and investors, why removing it hurts the people who can least afford it, and what (if anything) you can do about it. Plus: the annual Black History Month / Pitch Black recap tradition with Stephen Green.TIMECODES00:00 Oregon startup news intro04:27 Silicon Forest Tech Summit 202609:10 Oregon QSBS drama24:45 Black History Month 2026 recap28:35 SecretsLINKS Silicon Forest Tech Summit 2026 - Tickets / info: https://www.steamcircuit.com/events/61b8c1ba-e9bf-4dfc-b86e-17c125cd685b - SF post: https://siliconflorist.com/2026/03/06/why-is-no-one-talking-about-oregon-eliminating-qsbs-tax-breaks/ Black History Month / Pitch Black recap - SF post: https://siliconflorist.com/2026/03/02/black-history-month-2026-a-recap-of-pitch-black-participants/ - Pitch Black: https://pitchblack.org - Stephen Green's Instagram: https://instagram.com/pdxstepheng Mary Williams / Sasquatch Media Grounds - SF post: https://siliconflorist.com/2026/03/05/chatting-with-mary-williams-of-sasquatch-media-grounds/FIND RICK TUROCZY ON THE INTERNET AT…- https://patreon.com/turoczy- https://linkedin.com/in/turoczy- Portland Oregon startup news on Apple Podcasts https://podcasts.apple.com/us/podcast/portland-oregon-startup-news-silicon-florist/id1711294699- Portland Oregon startup news Spotify https://open.spotify.com/show/2cmLDH8wrPdNMS2qtTnhcy?si=H627wrGOTvStxxKWRlRGLQ- Startup Stories on Spotify https://open.spotify.com/show/1Tk7bbzaNYowGouI9ucKC3- Startup Stories on Apple Podcasts https://podcasts.apple.com/us/podcast/startup-stories-with-silicon-florist/id1849468494- The Long Con on Apple Podcasts https://podcasts.apple.com/us/podcast/the-long-con/id1810923457- The Long Con on Spotify https://open.spotify.com/show/48oglyT5JNKxVH5lnWTYKA- https://bsky.app/profile/turoczy.bsky.social- https://siliconflorist.substack.com/- https://pdxslack.comABOUT SILICON FLORIST ----------For nearly two decades, Rick Turoczy has published Silicon Florist, a blog, newsletter, and podcast that covers entrepreneurs, founders, startups, entrepreneurship, tech, news, and events in the Portland, Oregon, startup community. Whether you're an aspiring entrepreneur, a startup or tech enthusiast, or simply intrigued by Portland's startup culture, Silicon Florist is your go-to source for the latest news, events, jobs, and opportunities in Portland Oregon's flourishing tech and startup scene. Join us in exploring the innovative world of startups in Portland, where creativity and collaboration meet.ABOUT RICK TUROCZY ----------Rick Turoczy has been working in, on, and around the Portland, Oregon, startup community for nearly 30 years. He has been recognized as one of the “OG”s of startup ecosystem building by the Kauffman Foundation. And he has been humbled by any number of opportunities to speak on stages from SXSW to INBOUND and from Kobe, Japan, to Muscat, Oman, including an opportunity to share his views on community building on the TEDxPortland stage (https://www.youtube.com/watch?v=Cj98mr_wUA0). All because of a blog. Weird.https://siliconflorist.com#pdx #portland #oregon #startup #entrepreneur
Send a textWe unpack how marriage can meaningfully lower taxes for high-income earners and how to plan before and after the wedding. We share practical strategies on timing income, creating deductible losses, leveraging participation rules, and using healthcare and equity tools to keep more of what you make.• why joint filing usually reduces total tax• doubled standard deduction and home sale exclusion• capital gains thresholds and NIIT mitigation• pre‑wedding income shifting and gifting stock• delaying sales with loans and cash‑out refis• accelerating deductions in the final single year• state moves, residency timing, and common law options• building a joint asset and income map• combining hours to meet material participation• short‑term rental losses to offset W‑2 income• excess business loss limits for joint filers• hiring a spouse and using an HRA via sole prop• enabling HRA with rental management work• stacking QSBS exclusions with smart gifting• real estate professional status and cost segregation• estate planning updates for married wealthGo to prosperalcpa.com/opportunityreport for a personalized video on potential tax savings. Go to http:///www.prosperalcpa.com/apply to explore services and advanced tax planning.
From Olympic sprinter to trusted advisor helping entrepreneurs save millions in taxes, David Flores Wilson shares proven strategies for QSBS planning, equity compensation design, and preparing business owners for successful exits both financially and personally. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with David Flores Wilson, CFA, CFP, Managing Partner at Sinceres, who advises entrepreneurs and business owners in New York City on personal financial planning from formation to exit and beyond. David is a multiple Investopedia Top 100 Financial Advisor whose guidance has appeared in CNBC, Yahoo Finance, the New York Times, US News and World Report, and Investment News. WHAT YOU'LL LEARN: In this episode, you'll discover how QSBS planning can potentially exclude $10 million to $70 million or more in capital gains from taxes when structured correctly, why LLC to C Corp conversion timing creates dramatic differences in tax outcomes, and how QSBS stacking through non-grantor trusts multiplies exclusions. David shares why equity compensation plans often fail to motivate the specific people they target and what questions to ask before choosing a vehicle. You'll also learn about the personal readiness component of exit planning that determines whether entrepreneurs thrive or struggle after selling their businesses. DAVID'S JOURNEY: David's path to financial planning started with entrepreneurial instincts in an unexpected place. Growing up in Guam, he ran a comic book arbitrage business as a kid, discovering price differences between local stores and mainland mail-order catalogs. His father was a CPA with a home office, and despite wanting nothing to do with accounting, David absorbed financial concepts through osmosis that would later prove invaluable. After college at UC Berkeley, David joined Lehman Brothers and worked through the financial crisis. During that time, colleagues started coming to him with financial planning questions, and he realized helping people with their money was his true passion. He sat on that realization for years before eventually transitioning to financial planning. When Covid hit in 2020, David and his partner Dan Ryan launched Sinceres, and the firm has been growing since. OLYMPICS LESSON: David represented Guam in track and field at the 1996 Atlanta Olympics, competing in the 200 and 400 meters. The experience taught him something crucial about career selection. Unlike running, where pushing harder brings diminishing returns and constant injury risk, financial planning offers the opportunity to improve incrementally every single day. That compounding knowledge approach now drives how he serves clients. KEY INSIGHTS: QSBS planning stands out as potentially the most powerful tax planning tool for qualifying entrepreneurs. C Corps meeting holding period and active business requirements can exclude $10 million in gains, or 10 times basis for older shares, with new legislation increasing that to $15 million. The planning becomes even more powerful with LLC conversions where market value at conversion becomes the QSBS basis. The biggest mistake with equity compensation involves choosing vehicles based on what owners like rather than what motivates specific employees. "Equity" can mean participation in profits, upside potential, a seat at the table, or financial disclosure. Different people value these differently, and the best planning starts with understanding objectives before selecting tools. Exit planning involves three components that David implements from the first meeting with business owners. Getting personally ready addresses what provides purpose after selling. Getting financially ready ensures the numbers work. Getting business ready covers everything from customer concentration to management team development. The recent One Big Beautiful Bill Act has changed QSBS holding periods, SALT deductions, and AMT rules. Business owners should review their planning with advisors rather than assuming previous strategies still apply. Perfect for entrepreneurs considering entity structure decisions, business owners thinking about exit planning, and anyone interested in tax-efficient wealth building strategies. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davidfloreswilson FOR MORE ON DAVID FLORES WILSON: https://www.planningtowealth.com https://www.linkedin.com/in/davidfloreswilson/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps: [00:00] - Introduction: David Flores Wilson's credentials and areas of expertise [02:55] - Growing up in Guam with a comic book arbitrage business and CPA father [07:58] - Representing Guam at the 1996 Atlanta Olympics and career lessons from athletics [09:28] - QSBS fundamentals: Exclusions, holding periods, and qualifying business requirements [10:45] - LLC to C Corp conversions and the basis multiplication strategy [11:40] - QSBS stacking through non-grantor trusts and family gifting [19:40] - Equity compensation design: Why attraction, retention, and incentive vehicles often miss the mark[28:37] - Journey from Lehman Brothers through the financial crisis to launching Sinceres [31:59] - Exit planning framework: Personal, financial, and business readiness [41:27] - Recent tax law changes from the One Big Beautiful Bill Act [44:09] - What freedom means: Making impact through continuous improvement Guest Bio David Flores Wilson, CFA, CFP, is Managing Partner at Sinceres, advising entrepreneurs and business owners in New York City on personal financial planning from formation to exit and beyond. His areas of expertise include qualified small business stock planning, business exit planning, and equity compensation planning. David is a multiple Investopedia Top 100 Financial Advisor whose guidance has appeared in CNBC, Yahoo Finance, the New York Times, US News and World Report, and Investment News. He represented Guam in the 1996 Atlanta Olympic Games and sits on the Board of Directors as treasurer of the Lower East Side Girls Club. David is active in Entrepreneurs Organization, the Estate Planning Council of New York City, Advisors in Philanthropy, and the Exit Planning Institute. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Episode 325 - Kelly Finnell: Using ESOPs in Ownership Succession Planning Episode 350 - Tom Dillon: Understanding Business Valuation and Exit Planning Realities Episode 328 - Richard Manders: Post-Exit Transitions and What Comes After Selling Your Business Episode 339 - Solocast 74: Equitizing Key Employees and Succession Planning Strategies Follow DealQuest Podcast: LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/ Follow David Flores Wilson: Website: https://www.planningtowealth.com Keywords/Tags QSBS planning, qualified small business stock, business exit planning, equity compensation, entrepreneur tax strategy, LLC vs C Corp, financial planning for business owners, exit planning institute, tax-efficient wealth building, business succession planning, capital gains exclusion, non-grantor trusts, C corporation conversion, equity incentive plans, entrepreneur financial advisor
Lowenstein Sandler's Trusts & Estates Podcast: Splitting Heirs
In this episode of Splitting Heirs, partners Beth Shapiro Kaufman, National Chair of Private Client Services and Trusts and Estates Chair, and Kristin V. Taylor join host Warren K. Racusin to discuss the One Big Beautiful Bill through a tax and estates lens. They talk about "permanence" in the tax law while explaining the new estate and income tax benefits in OB3. Kaufman, Taylor, and Racusin elaborate on and debunk some of the bill's hot topics, including no tax on tips, no tax on social security benefits, SALT deductions, QSBS, and the 2/37ths rule. Speakers: Warren K. Racusin, Partner and Chair, Trusts & Estates Beth Shapiro Kaufman, Partner, National Chair, Private Client ServicesKristin V. Taylor, Partner, Tax, Private Client Services
This conversation delves into the intricacies of Qualified Small Business Stock (QSBS) and its significant tax benefits for founders. MICHAEL ARLEIN, Partner at Patterson Belknap, explains the eligibility criteria, the importance of strategic planning, and the potential pitfalls that can arise. The discussion also covers the implications of state taxes and the advantages of gifting strategies. We cover innovative approaches like the “GOAT” trust to maximize tax-free gains. Founders are encouraged to engage with legal experts early in their business journey to fully leverage QSBS opportunities. https://youtu.be/lfBt0j7BlW0?si=LufZ8j2YtgdspLMJ Takeaways from “QSBS For Founders” QSBS is a powerful tax benefit for founders.The maximum exclusion amount has increased to $15 million.Careful planning is essential to avoid QSBS pitfalls.Gifting QSBS stock can multiply tax exemptions.State tax implications vary; California does not recognize QSBS.Discounting shares can aid in estate planning.Converting from an S-Corp to a C-Corp can preserve QSBS benefits.Early engagement with legal counsel is crucial for founders.Innovative strategies like the GOAT trust can maximize benefits.Almost all businesses should consider QSBS eligibility. Chapters 00:00 Understanding QSBS: A Founder’s Guide.02:56 Navigating the QSBS Landscape: Common Pitfalls.06:07 Maximizing QSBS Benefits: Stacking Strategies.08:42 The Importance of Timing: Gifting and Valuation.12:03 State Tax Implications: The QSBS Challenge.14:52 Entity Structures and QSBS: What Founders Need to Know.17:37 Transitioning to C-Corp: Strategies for S-Corps and LLCs.20:29 Who Should Pay Attention to QSBS?23:44 Innovative Business Structures: Technology and QSBS-26:36 Early Stage Strategies: Cloning Yourself on the Cap Table- Transcript of “QSBS for Founders” Frazer Rice (00:01.109)Welcome aboard, Michael. Michael Arlein (00:03.096)Thank you. Good to be here. Frazer Rice (00:04.617)So let’s get started here. QSBS, Qualified Small Business Stock, is something that certainly all founders should be aware of. It’s a tax feature. It’s probably one of the nicest goodies that the federal government gives to people who are starting businesses. Take us through a little bit about what happens there. For founders, you’re going to hear the numbers 1202, which is the section that is quoted here. Take us through a little bit about what happens at QSBS and why it’s a powerful feature. Michael Arlein (00:37.496)Sure, that sounds good. To your point, the New York Times called QSBS a lavish tax dodge that is easily multiplied. And I happen to. I’m not aware of any other provision of the tax code that can save anyone as much money as QSBS. It’s really incredible. I think the policy reasons behind the provisions are that they’re designed to encourage entrepreneurship. Everyone on both sides of the political aisle is in favor of. The basic premise of it is that if you create a company.You own the stock for five years. The company’s in the form of a C corporation, It’s not in one of a series of restricted industries. Mainly service industries, that when you sell the stock, you can exclude from paying tax $10 million, the first $10 million of your gain. That’s the old rule, which I’m still dealing with, that that’s for stock that was issued before July 4th, 2025. And now QSBS has gotten even better. So if you get stock after that date. You hold it for actually now three years, you can exclude ultimately up to $15 million from tax. So we’re now dealing with two different regimes. I’m still stuck in the old regime. Most of the people I’m dealing with got their stock before last July. But I’ll try and point out the differences as we go along. Frazer Rice (02:29.066)Sure, as you said, there are a bunch of things you have to jump through. To make sure that you can sort of apply and then to further comply with the rules associated with it. Things like services. Making sure that maybe you don’t have too much cash and that it’s deployed correctly. Making sure that the original stock issuance persists throughout. What are some of the things that you tell your clients? How do you walk them through the process so that they don’t trip on themselves and lose this nice tax advantage? Michael Arlein (03:09.676)Yeah, there are some landmines, things that you can step on and blow it. There’s some weird rules around redemptions. Like if you have redemptions. Let’s say you create a company and then there’s three co-founders. Then very early on, one of the co-founders wants out or you want to kick them out. And then the mechanism for that is the company kind of buys back their stock. You know, there’s complicated rules that can, you know, blow up QSBS for the entire company. I think some people start their businesses as LLCs or S-Corps or things like that, and then later convert them. And that has to be done very, very carefully with good tax advice. Otherwise that can also blow things up. When I talk to founders, it’s pretty clear their business qualifies. They didn’t screw anything up. Frazer Rice (04:19.626)So the OBBBA in a sense turbocharged a little bit the tax savings. That five year requirement that you talked about. You can now get some of the benefits even as early as three years. And then the dollar amounts got expanded. In addition, and this was not necessarily OBBBA related. The ability to take one exemption and maybe multiply it via stacking continues to be a powerful tool. For those people who are walking into your office now. How do you get them when they sit down situated so that they do that planning upfront? Michael Arlein (05:08.598)Yeah, that’s, you we kind of buried the lead. The benefit of QSBS: it would be incredible if you could just pay no tax on 10 or $15 million. But what’s even more incredible is that you can stack or multiply the number of exemptions. You have using a provision of the code. It says that if you gift QSBS stock to some other person or entity. That that person or entity can take their own up to 10 or 15, their own QSBS exemption. I’m just gonna say it’s 15. We understand that’s for newly stocked. So, classic move for a founder would be to set up trusts for children. There’s a special kind of a trust for a spouse. You can do this with sometimes people make trust for their parents, their siblings. There are certain states where you can actually make a trust for yourself. Usually when people come to my office, the conversation is around creating entities. Typically trusts, and then gifting shares to those trusts. that As a family, you could go from 15 million tax free to 30 or 45 or 60 million tax free. The record I had one guy who had a very large family. He married, he had kids and was very close not only with his parents. With his siblings, his nieces, his nephews, even his aunts, uncles, and cousins. He created 23 trusts, which on paper at least would save up to $230 million. Wow. Yeah. Frazer Rice (07:08.896)There’s a danger with that though, with those 23 trusts had to be different. I imagine the IRS would say, wait a minute, we see what you’re doing. Stacking all of these different things is theoretically nice and all, but is there a way to create differences within those trusts so that the IRS doesn’t view them as one big pot? Michael Arlein (07:39.692)Yeah, great question. So you can’t create multiple identical trusts. Meaning I can’t create five trusts for my child. The IRS has rules that consider those trusts as one trust and would have only one exemptions. So, one of the limiting factors on creating trust is often, who are the people you’re willing to gift to? You know, so this guy with the 23, he actually was willing to create trust for his cousins, his aunts, uncles. Now, those individuals were the beneficiaries of the trusts, which means that they were eligible to receive money from the trust. But those trusts were designed so that when those people passed away, the money would circulate back to his children. So, you we never talked about it, but it’s possible that in his head, his plan was that he would maybe provide some benefit to his cousin. Maybe he’d say to his cousin, hey, if there’s $5 million in this trust and you need a little money, I’ll make some distributions to you, but I’m going to request that the trustee kind of withhold most of the money. And then when you die, it’ll come back and benefit my kids. So there are nuances there. But generally speaking, most people aren’t willing to do that. They’re not close enough with their cousins and their aunts and their uncles. So they end up maybe creating trusts, you know, for their kids, for their parents, sometimes, you know, for their spouse and maybe sometimes they go a little beyond that, but not that far. One thing that’s important is that the U.S. Frazer Rice (09:33.472)One thing that’s important is that the the QSBS is a capital gains tax Concept meaning you’re you’re saving on the tax. From a QSBS for Founders standpoint when the the founder sells the business, and you have to pay capital gains tax on that front. Part of the reason I’m skewing this toward founders is that there’s an gift in a state exemption of 15 million dollars. So it’s important to get these assets into these trusts as early as possible and with as low evaluation as possible. That in many ways is where the real leverage is. Does that square with your thinking? Michael Arlein (10:11.019)Yeah, absolutely. We have a permanent $15 million lifetime gifting limit. $30 million for spouses. And when you gift stock into these trusts, you’re typically gifting at a common stock valuation. People are familiar, founders are familiar with common stock valuations because they do that for purposes of issuing stock options, you know, the so-called 409A valuation. Now, a gift tax appraisal is different than a 409A valuation, but in many ways, they’re very similar. S0 founders know that, you know, they could be raising a preferred round at $10 a share, but their 409A common stock valuation is still $2 a share. So you can get a lot of gifting done. You can give a lot of shares away. You know, using your $15 million exemption, even if the company is very valuable. So we see founders doing this sort of gifting, you know, late in the game, even right before a transaction or an IPO. But if you had a crystal ball, or at least, you know, you were willing to take some risk, obviously, the earlier you do it, the better, because you could gift… I mean, theoretically, if you set up trusts and you gifted shares the day after you created your company, they would be worth essentially nothing. And so you wouldn’t have to use hardly any of your gifting exemption. The problem is most people, A, aren’t thinking about that on the day they create their company. They don’t have anyone whispering in their ear and telling them to do that. And number two, they wouldn’t want to spend the money on legal fees to set up structures because at that point they’re like, don’t know what this is going to be worth. This could be zero. This could go out of business in a year. So there’s a trade off that I see between doing this later in the process where you’re gaining visibility into outcomes, maybe for younger people sometimes, you know, there’s visibility into their family lives. Maybe when they founded the company they were single. Then if they wait five years they marry, they’ll have children, i.e. people who they could create trust for. But the cost of doing that is that you’re gifting at a higher value. Frazer Rice (12:46.591)One of the considerations that people don’t understand is the state tax implication. QSBS is a federal concept that a lot of states join onto and link to. But a state like California isn’t. And so sometimes that can be an untoward surprise to people that there’s a state tax that happens that they may not have expected. Michael Arlein (13:16.299)Yeah, it’s kind of bizarre that California, the home of Silicon Valley, doesn’t recognize QSBS. But most states do. My home state of New Jersey, in fact, very recently joined the QSBS club and now recognizes it at the state level. There are a few other states, I think. Pennsylvania, I don’t think recognizes it, but the vast majority of states do. But unfortunately, if you live in California, you’re probably only in quotes saving the federal tax. But the federal tax on $15 million, 23.8 % of 15 is a pretty big number. Frazer Rice (14:01.086)No question and absolutely worth doing. one of the things that I find happens is that from an income capital gains tax perspective, we’re on top of it with the QSBS. When we get into the estate planning world, we use the concept of discounting, meaning putting QSBS shares or any shares for that matter into other entities so that you get discounting for lack of marketability and the ability to make decisions around it. Are there any tripwires on that front as far as putting things into other LLCs so that you don’t, maybe in a sense that in trying to really maximize the estate planning and the estate tax avoidance that you create issues that might cause problems with your QSBS tax avoidance usefulness there. Michael Arlein (15:02.413)Yes. Again, the rules under Section 1202 of the code for QSBS have some strange traps for the unwary and some gray areas. And one of those gray areas is around transferring interests in partnership type entities, which would mean like an LLC or a partnership. that owns QSBS. So essentially, it’s very clear that if you have QSBS stock and you gift it into one of these entities we’ve been talking about, that that entity would take the QSBS attribute and be able to enjoy the benefits of QSBS. If the QSBS is held in an entity like an LLC, let’s say you set up a, well. Let’s say a realistic example is that you made an investment in a venture capital fund that invested in an early stage company that’s QSBS. And now you’re a limited partner in that fund and you know that that fund is going to have a large exit in this QSBS position and that you’re going to get the benefits of that, but it’s going to exceed $15 million. So you say, what I should do is I should take my interest in this venture capital fund. I should give them to trust for my kids so that when the fund distributes those shares or distributes the proceeds from selling that company, it’ll be split among various entities and I’ll be able to stack QSPS. The transfer of an interest in a fund that owns QSPS, there’s a gray area about whether the recipient of that fund interest would actually have QSPS and it’s generally viewed as something to be avoided. Frazer Rice (17:08.944)In a sense putting it at risk. A question that I think pops up is that there are people who started businesses maybe pre that July 4th date that you were talking about and maybe they chose an entity like an S Corp or an LLC that isn’t sort of a good qualifying C Corp and they’re looking and saying you know what I may be able to sell this business three to five years or beyond and take advantage of this QSBS. Are there avenues to be able to change that tax elections so that you can begin that QSBS and what’s the analysis around? Michael Arlein (17:44.972)Yeah, in fact, a fairly common structure is, and we haven’t really gotten into these details, but it’s a great question. So QSBS is actually the greater of $15 million or 10 times your basis. Now we ignore the basis rule for the most part because the vast majority of founders do not have basis. They create their company and they put nothing into it. With a bank account with $10,000 in it, and they’re not contributing actual dollars into their business. And so the 10 times basis rule doesn’t actually apply. But there’s a way for a founder to take advantage of that, and this strategy is actually called PACKING. And the packing strategy involves starting your business as an LLC and with an LLC and then converting it to a C corporation. with an LLC, when you convert, there’s an attribution of basis to the founder based on the value of the LLC’s assets. Theoretically, if you started off as an LLC, and before the LLC hit $75 million value of its assets, $75 million being sort of the cutoff for qualifying for small business, you have to acquire your stock before your company assets are worth $75 million. Theoretically, let’s say you did that when it was $74 million, then if your basis was $74 million, 10 times your basis would be $740 million, you would have up to $740 million tax free. So people kind of play this game. I think for a lot of companies, it’s not realistic to be an LLC because venture cap, if you’re going to raise venture funds, they want you to be a C Corp. This works for bootstrapped companies, but most companies are forming a C corporations. You know, there is a path to convert from an S-Corp to a C-Corp and preserve QSPS for Founders. I’m no expert in that. All I can tell you is that it has to be done very carefully and very specifically. And I’ve seen a lot of people who didn’t know they needed to do anything specific and they do not qualify for QSPS. Frazer Rice (20:45.085)As we sort of, I’m not going to say wind down here because we may have some other topics that pop up. But when someone walks through their door, I guess maybe the way to think about it is, who does this apply to? You said the services industry. So accounting, finance, that type of thing- NO. For those things that venture tries to invest in, whether it’s software or other processes, who is really should be paying attention to this? Michael Arlein (21:16.491)I mean, I think almost anyone should be paying attention to this because it may be that you don’t qualify, but often people do. And more often than not, you do. This has broad application for most businesses. There are excluded industries, architects and lawyers and accountants. But if you’re doing something in the tech world, you’re probably going to qualify. It’s good to get some advice from the corporate lawyer who’s helping you create your business. I think one of the considerations of whether you form as a C Corp or an LLC is probably the availability of QSBS status. You know, I think stacking strategies, it’s worth having a conversation probably sooner than later with a lawyer to find out what the menu of stacking options is. I talk to people all the time and we decide it’s premature for them to do something. And then they call me back a year or two later and all the time I’m calls from people who say, hey, we spoke a few years ago and now Frazer Rice (22:34.013)Alright. Michael Arlein (22:39.913)the time is right. So it’s good to get educated, learn what the options are. QSBS stacking is not just about giving shares to your kids. There are strategies that are specifically designed for single people where you can create these benefits for yourself and You know, it’s too good to be missed. if you, I do talk to people who say to me, they’re usually on their second venture or third venture and they say to me, I really screwed this up the first time around. I paid no attention to it and I was focused on my business and I just screwed it up. I literally cost myself millions or tens of millions of dollars had I done it correctly. And now that’s why I’m calling you, because I want to do it correctly the second time around. Frazer Rice (23:33.278)Part and parcel with that, I ran into somebody really more of what’s called a media personality. And usually the way I think of it is that the QSBS isn’t necessarily available for people whose value is centered around them as a personality or them as a brand. But I said, you know what, the QSBS component, while it might not apply here, if your business morphs into something where you’re developing other things, slash maybe you turn into a media production company or, youbecome involved in a technology that drives other things, that you shouldn’t dismiss that. The pivot in the business from sort of a personality generated to something a little bit more business process generated might be something to think about, not only from a strategy standpoint, not that you necessarily wanna do things purely for tax reasons, but if that’s a natural consequence, that’s something to think about. Has that ever popped up in your world? Michael Arlein (24:31.915)Yeah, for sure. Every business these days is technology enabled. And I think sometimes businesses that you wouldn’t think of as being technology businesses are doing enough technology things that they can claim that they’re a technology business and not a business providing a particular kind of service. So, you know, with the help of a clever accountant or a tax lawyer, this is not an area that I operate in. I’m more about multiplying QSBS once you have it. But there are tax lawyers and corporate lawyers and accountants who can advise you how to make your business eligible for QSBS by leaning into, as you said, things that you’re doing that may be…you know, eligible versus other parts of your business that would not be. Also, you know, you can, sometimes you see companies that are divided, right? Like, so there’s a company who provides counseling services, like, you know, they’re actually hire psychotherapists that will counsel you, you know, online, like on a Zoom. and their business is split. There’s a medical services company that employs all the counselors and medical services is one of the excluded industries. But then they also have a completely separate business that is their technology platform. And the way they structured it, the value is really in the technology platform. That business is QSBS eligible because it’s a completely separate company. Frazer Rice (26:28.771)That’s a great example. part of the purpose of the question was to elicit that, is that people may say, well, we fall squarely into one classification when maybe some underlying thought might lend itself to structuring from a tax perspective that might be useful later on. OK, now as we wind down, for someone who is, at this point, starting a company when they’re forming these things, not that you, QSBS for Founders should drive the world, but how do they get involved with the discussions so that they do the right things early? Michael Arlein (27:06.401)Yeah, I mean, I do have a very specific strategy that I love for people who are about to form a company. And it really works best in that scenario of an early stage company that’s just about to launch. The way I describe this to founders is that you can and should clone yourself on the cap table. So if you start off a company and you own all of the shares, you’re basically eligible for 15 million tax free. That’s great. But what if you could clone yourself and there were three Frazers on the cap table, then Frazer would have $45 million tax free. So how do you do this? You can do it with trusts. And the beautiful thing is if you have other people create trust for you, then you can be the beneficiary of the trust and control it as well. And I have sort of branded and named this strategy a GOAT trust, which of course has the double meaning, know, greatest of all time. Frazer Rice (28:21.02) QSBS for FoundersRight. Michael Arlein (28:21.165) QSBS for FoundersBut actually stands for gift optimized to alleviate taxes. The essentials of it are is that we would work with your parents, the founders parents, we would work with your grandma, your uncle, and we would spin up some trusts that they create for the benefit of you as the founder. You would have all sorts of control and access to those trusts and they make a gift into those trusts, probably something fairly modest. Then those trusts on the day of formation buy up some of the common stock. And so those are your clones. You know, you’re having your cake and eating it too. You’re getting, you know, QSBS stacking for Founders. You’re getting some other benefits we haven’t even talked about. Those trusts can be exempt from a state tax and state level income tax. And you control those trusts and benefit from them. So we’ve essentially cloned you on the cap table. And that is a beautiful strategy that most people miss out on because they don’t do it. And then they come to me a few years later and they own the stock and it’s valuable and then we have to do the more traditional stacking strategies. Frazer Rice (29:40.432)Really cool stuff. Michael, how do people get in touch with you if they have these problems slash opportunities? Michael Arlein (29:48.525)Sure, well they can Google me. I have a nice web presence. We have our…Founder Focus Practice Group that I lead at the firm, which is very specifically tailored to provide legal services to founders, personal legal services. And I focus on the tax side of that and QSBS stacking for Founders. My email, msarlein at pbwt.com. Phone number 212-336-2588. Frazer Rice (30:23.324) QSBS For FoundersThat will all be in the show notes. Michael, thanks for being on. Michael Arlein (30:26.753) QSBS For FoundersThank you. FAMILY OFFICE MYTHS https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/ QSBS for Founders QSBS for Founders
גיא קצוביץ' מארח את עמית קרפ (Bessemer Venture Partners), ברק שוסטר (Battery Ventures) וינאי אורון (Vertex Ventures) לדיון סוער על האירועים המרעישים בהייטק.הפרק עוסק ברכישת QAI על ידי אפל (Apple) בסכום של 1.5 מיליארד דולר וטכנולוגיית ה-Silent Speech, בניסוי החברתי המרתק והמסוכן של OpenClaw (לשעבר ClaudeBot) שיוצר רשת חברתית של סוכני AI, ובמגמת המעבר של סטארטאפים ישראלים לרישום כחברות דלאוור (Delaware) בארצות הברית.בנוסף, מנותחים ביצועי מניות ה-SaaS בבורסה, השפעת הבינה המלאכותית על עולם הגיימינג (Google Genie) והתמריצים הנדרשים ליזמים בישראל.(00:00) - פתיחה (02:37) -אפל רוכשת את QAI ב-1.5 מיליארד דולר(09:32) - הניסוי של OpenClaw: רשת חברתית לבוטים(32:32) - סוכני AI אישיים: פרודקטיביות או סכנה? (44:17) - משבר הרישום: ישראל נגד דלאוור (QSBS)(54:12) - גוגל ג'יני והתרסקות מניות הגיימינג וה-SaaSלאינסטגרם של גיא: https://bit.ly/48OziEHלפודקאסט באינסטגרם: https://bit.ly/4oND8Toלפודקאסט באפל: https://apple.co/3Lfv8Mbלפודקאסט בספוטיפיי: https://bit.ly/47Th96H
American Institute of CPAs - Personal Financial Planning (PFP)
Non-grantor trusts are stepping into the spotlight, not for estate tax, but for income tax planning. In this episode, Cary Sinnett sits down with tax expert Bob Keebler to explore how the One Big Beautiful Act (H.R.1) reshapes the planning landscape. You'll hear how you can use trusts to reclaim lost SALT deductions, stack §199A benefits, shift income across generations, and even layer in QSBS exemptions. If your clients are hitting phaseouts or facing high state taxes, this episode delivers advanced strategies to optimize their tax position now and into the future. Non-Grantor Trusts: Keebler explains how trust structures can sidestep phaseouts and help clients reclaim deductions previously lost due to high AGI. The "Tax Trifecta Trust" Explained: Learn how to stack SALT deductions, layer multiple §199A deductions, and shift income strategically using non-grantor trust planning. Five Strategies You Can Use Today Income shifting to lower-bracket heirs Stacking SALT deductions across multiple trusts Boosting §199A deductions with trust-level taxpayers Expanding QSBS exemptions via strategic trust ownership Reducing or deferring state income tax through out-of-state trust situs Real-World Implementation Advice: Bob outlines guardrails around IRC §643(f) to avoid having multiple trusts collapsed into one. Hear how to structure trusts legally and practically for high-impact planning, and how to identify ideal client profiles for this approach. What CPA Financial Planners Need to Watch For: Bob discusses state-specific issues, kiddie tax complications, trust drafting must-haves, and how CPAs can lead the planning process with confidence. AICPA Resources: Video: Decoding Trusts and Wills: Provisions for PFP Practitioners Video: Year-End Planning Through the Lens of H.R. 1 Resource: Charitable planning post OBBBA rules This episode is brought to you by the AICPA's Personal Financial Planning Section, the premier provider of information, tools, advocacy, and guidance for professionals who specialize in providing tax, estate, retirement, risk management and investment planning advice. Also, by the CPA/PFS credential program, which allows CPAs to demonstrate competence and confidence in providing these services to their clients. Visit us online to join our community, gain access to valuable member-only benefits or learn about our PFP certificate program. Subscribe to the PFP Podcast channel at Libsyn to find all the latest episodes or search "AICPA Personal Financial Planning" on your favorite podcast app.
In this episode of the Be Wealthy Podcast, Brett Tanner sits down with his longtime CPA, tax strategist, and trusted advisor Brian Muia for a deep dive into entrepreneurship, wealth-building, and advanced tax strategy.Brian shares his journey from growing up with limited resources to building and exiting multiple businesses, including companies in software, steel recycling, and accounting. He breaks down how early lessons around hard work, leverage, and replaceability shaped his entrepreneurial mindset — and why building a business that doesn't rely on you is the key to true freedom.The conversation goes deep into passive income, leverage, exits, subscription-based businesses, and the latest tax strategies from the “Big Beautiful Bill.” Brian explains how smart planning around depreciation, Section 179, QSBS, and opportunity zones can dramatically accelerate wealth creation for entrepreneurs and real estate investors.This episode blends real-world business lessons, mindset, and highly tactical tax insights every serious entrepreneur should understand.
In this episode of Tank Talks, host Matt Cohen and recurring guest John Ruffolo kick off the new year with a true “only in 2026” combo: a front-row seat to a SpaceX Falcon 9 launch carrying Kepler Communications' satellites, followed by a hard reality check on Canada's venture capital slowdown. John breaks down what it felt like watching the rocket, the first-stage landing, and why Kepler's mission is bigger than a cool space flex: it's the early shape of space-based data centers and laser-linked networks.From there, Matt and John unpack an RBCx report arguing 2025 was Canada's worst VC fundraising year since 2016, and why “capital is fungible” is a comforting myth at the seed stage. They dig into how de-globalization and national self-interest are reshaping capital flows, why Canada is getting squeezed by the barbell effect in venture, and what policy levers (like a QSBS-style incentive) could actually restart domestic risk capital. The episode closes with two tension points that rhyme: Nvidia's $20B Groq (with a Q) deal showing how returns can flow outside Canada, and the escalating political drama of Trump's DOJ targeting Fed Chair Jerome Powell and what that uncertainty does to markets.If Canada can help put “data centers in the sky,” can it also build the domestic capital base to keep its best companies anchored at home?“A Data Center in the Sky” + Laser-Linked Networks (00:03:07)Kepler's satellites are positioned as more than comms hardware: think orbital compute + storage + real-time processing, with laser links connecting satellites like a network in space.The RBCx VC Report: 2025 Fundraising Hits a Low (00:05:51)Matt summarizes the report's headline numbers and why the pain concentrates on emerging managers and the long tail, not the handful of breakout founders who can raise anywhere.“Venture Investing Is Local” in a De-Globalizing World (00:08:39)John challenges the idea that foreign capital will fill gaps at the earliest stages. In this cycle, countries increasingly keep capital for their own ecosystems, making Canada's domestic shortage more dangerous.The Barbell Effect: Giants and Niche Funds Win, the Middle Gets Crushed (00:10:17)They outline how venture is polarizing into mega-platform funds and specialized micro-funds, while mid-sized generalists get squeezed, and why that dynamic is amplified in Canada.Nvidia's $20B Groq Deal and Canada's Return Profile (00:12:36)They break down the Groq (Q) story, Canadian ties among investors and operators, and the bigger question: if LPs can make outsized returns elsewhere, what keeps capital committed to Canada?Trump vs Powell: DOJ Pressure, Fed Independence, and Market Fallout (00:17:38)They react to the reported DOJ move against Jerome Powell, how even Republicans are uneasy about weaponization, and why political pressure campaigns tend to increase uncertainty, not lower it.Why Uncertainty Pushes Rates Up, Not Down (00:19:30)John's punchline: the intended outcome (lower costs, lower rates) can backfire as markets price in instability, and the Powell timeline may extend into a longer institutional fight.Connect with John Ruffolo on LinkedIn: https://ca.linkedin.com/in/joruffoloConnect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1Visit the Ripple Ventures website: https://www.rippleventures.com/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit tanktalks.substack.com
Stop letting your tax return tell the only story about your money. We invited Rob Cook—CPA, CFP, and seasoned advisor to executives, athletes, and families—to break down how real tax strategy starts with who you are, where you want to go, and the few moves that actually change your outcome. Instead of chasing every trick on the internet, Rob shows why stacking “base hits” creates immediate savings and flexibility, and how to choose one or two “home runs” that fit your strengths.We talk through the crucial difference between a historian CPA who files forms and a strategic partner who looks through the windshield. You'll hear why high-earning W‑2 professionals are not stuck, how accredited status opens meaningful options, and how to avoid complexity that rich headlines can afford but most people can't defend. Rob shares a simple, repeatable process: clarify your goals and constraints, close tax leaks hiding in plain sight, align strategy with life and cash flow, then implement and iterate as your fastball evolves.From HSAs, donor-advised funds, and retirement plan design to QSBS, cost segregation, and real estate professional status, we separate the tools from the hype. You'll learn how to convert personal costs into valid business deductions when facts allow, why lifestyle creep kills deployable capital, and how a personal CFO framework helps you save taxes without sacrificing sanity. The goal is clarity and control: a lighter tax bill, a simpler structure, and more energy for the work and people you love.If you're ready to make money simple and build around your true wealth creation play, this conversation is your blueprint. Subscribe, share with a friend who needs a better plan, and leave a review telling us your top “base hit” to implement this week.-----With over 10 years of experience in accounting and wealth management, Rob has worked with everyone from CEOs and world-class athletes to local families, helping them reduce taxes, build wealth, and achieve financial freedom. Holding both a Master's and Bachelor's in Accounting from BYU, he is a Certified Public Accountant (CPA), Certified Financial Planner (CFP®), and has passed Level I of the Chartered Financial Analyst (CFA) exam.Known for bringing both expertise and personality to finance, Rob is passionate about personal finance, taxes, and investing. Frustrated with the industry's lack of real impact, he set out to truly help people transform their financial futures—and now, that's what he does every day.Connect with Rob Cook:Rob Cook, Bement & Company, Director of Strategic Tax380 North 200 West Ste 112 Bountiful, UT 84010801-936-1900rob@bementcompHear Past episodes of the Way2Wealth Podcast!https://theway2wealth.com Learn more about our Host, Scott Ford, Managing Director, Partner & Wealth Advisorhttps://www.carsonwealth.com/team-members/scott-ford/ Investment advisory services offered through CWM LLC, an SEC-registered investment advisor. Carson Partners, a division of CWM LLC, is a nationwide partnership of advisors. The opinions voiced in the Way to Wealth with Scott Ford are for general information only and are not intended to provide specific advice or recommendations for an individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing. Guests on Way to Wealth are not affiliated with CWM, LLC. Legado Family is not affiliated with CWM LLC. Carson Wealth 19833 Leitersburg Pike, Suite 1, Hagerstown, Maryland, 21742.
Why do billions of dollars of stock trade hands based on napkin math and vibes? Billy Gallagher, CEO of Prospect and former Rippling employee, joins Patrick McKenzie (patio11) to walk through the information asymmetry that costs less-sophisticated employees massive amounts of money. From understanding when to early exercise options to navigating 83B elections and tender offers, they discuss the critical decisions that have a shot clock ticking the day you sign your offer letter.–Full transcript available here: www.complexsystemspodcast.com/understanding-equity-at-tech-companies/–Sponsor: Framer is a design and publishing platform that collapses the toolchain between wireframes and production-ready websites. Design, iterate, and publish in one workspace. Start free at framer.com/design with code COMPLEXSYSTEMS for a free month of Framer Pro.–Links:Prospect: www.joinprospect.com/–Timestamps:(00:00) Intro(00:44) Billy's professional journey(01:07) Equity management challenges(02:29) The importance of equity compensation(04:53) Equity grant structures in startups(06:09) Understanding vesting terms(07:09) The value of equity over time(08:48) The myth of options as lottery tickets(11:23) Career tailwinds from startup experience(14:25) Breaking into the tech industry(15:16) The role of equity in compensation(17:49) Employee equity plans and dilution(19:59) Sponsor: Framer(21:06) Stock options vs. RSUs(21:55) The decision to exercise options(27:11) Tax implications of exercising options(33:03) The role of HR in equity management(36:14) Bootleg spreadsheets and vibes-based investing(38:09) Navigating tax complexities in different scenarios(41:31) The importance of extended exercise windows(44:18) Challenges with tax residency and remote work(49:43) The role of accountants in managing equity(53:41) Understanding the 83(b) election and QSBS(01:01:03) Tender offers and secondary sales(01:08:38) Strategies for exercising and selling options(01:12:28) Navigating financial decisions in startups(01:16:59) Wrap
In this episode, Sasha Orloff talks with Nick Abouzeid, Co-founder and CEO of Rivet, about raising venture capital from XYZ, Haystack, and other angels to build a modern tax and accounting firm that serves 600+ category-defining companies like Cursor by combining world-class tax practitioners with custom-built software infrastructure, delivering premium responsive service while challenging the traditional accounting firm model of unresponsive service and outdated technology. -- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at https://notion.com/startups/puzzle Puzzle
Are you building wealth — or just hoping it lasts?In this episode of Grow Your Business & Grow Your Wealth, host Gary Heldt speaks with Katherine M. Sheehan, Managing Director and Wealth Strategist at Crestwood Advisors, about how smart planning protects both your business and your legacy.Katherine breaks down what every entrepreneur should know about estate and succession planning — from powers of attorney to corporate recordkeeping — and explains how the Qualified Small Business Stock (QSBS) provision can help business owners exclude up to $10 million in gains when selling their company.You'll learn how to avoid costly mistakes, when to bring in specialized advisors, and how to prepare the next generation to carry your vision forward.
Are you building wealth — or just hoping it lasts?In this episode of Grow Your Business & Grow Your Wealth, host Gary Heldt speaks with Katherine M. Sheehan, Managing Director and Wealth Strategist at Crestwood Advisors, about how smart planning protects both your business and your legacy.Katherine breaks down what every entrepreneur should know about estate and succession planning — from powers of attorney to corporate recordkeeping — and explains how the Qualified Small Business Stock (QSBS) provision can help business owners exclude up to $10 million in gains when selling their company.You'll learn how to avoid costly mistakes, when to bring in specialized advisors, and how to prepare the next generation to carry your vision forward.
Terry Sylvester Charron, head of investment advisory and planning solutions, and Jere Doyle, senior wealth strategist, unpack changes to Qualified Small Business Stock as result of OBBBA.
S4:E196 David gives The Venture Update with a special segment on the potential impact of Quantum Tokens on the blockchain. Then Paul provides a brief update on the current status of Capital Gains Tax Exclusion for gains on Qualified Small Business Stock or QSBS with Ben Glenn, an accountant specializing in startups. The One Big Beautiful Bill substantially updated the QSBS rules, solidifying one of the key incentives for startup investing for stock issued on or after July 5, 2025. (review recorded 10.1.25)Follow David on X at https://x.com/DGRollingSouth Follow Paul on X at https://x.com/PalmettoAngel Connect On LinkedIn with David at https://www.linkedin.com/in/davidgrisell/ Connect On LinkedIn with Paul at https://www.linkedin.com/in/paulclarkprivateequity/ We invite your feedback and suggestions at www.ventureinthesouth.com or email david@ventureinthesouth.com. Learn more about RollingSouth at rollingsouth.vc or email david@rollingsouth.vc.
Guest: Alex Duta CEO/Founder at Albi (restoration management software) https://albiware.com/ Thinking about selling to PE? Alex explains why many contractors should hold and tech-enable instead then shows how to do it: AI for ops, revenue per-employee targets, CRM→Ads feedback loops, valuation math (service vs. software), and the QSBS play to keep more at exit. Real tactics for restoration/roofing/plumbing/HVAC leaders who want margin, scale, and optionality.You'll learnWhat “tech-enabled” actually means for a contractor (and how to measure it)A prioritization toolkit (RICE) to pick high-leverage automations firstCRM→Google Ads conversion feedback to drop CPL & boost job sizeHow tech enablement changes valuation multiplesA primer on QSBS and why waiting can be worth millionsConnect with Alex: https://alexduta.com/ • @itsalexduta Hire Hook Agency for home-service growth: https://hookagency.com/
גיא קצוביץ' מארח את עמית קרפ (Bessemer Venture Partners), ברק שוסטר (Battery Ventures) וינאי אורון (Vertex Ventures Israel) לניתוח גל הפיטורים באמזון (Amazon) ולייטריקס (Lightricks) והשאלה האם AI הוא הסיבה האמיתית, או תירוץ להתייעלות. הדיון עובר לעתיד חברות ה-SaaS מול חברות "AI FIRST", בוחן את "כלכלת הבחירות" של שר האוצר בצלאל סמוטריץ', ומסביר מדוע יזמים ישראלים מעדיפים להתאגד בדלאוור (Delaware) בזכות הטבת המס QSBS. בנוסף, נתונים חדשים על יזמים סדרתיים (Wiz, CyberArk) בישראל, והמעבר של OpenAI למבנה רווחי בשווי 500 מיליארד דולר(00:00) - פתיחה(04:24) - פיטורי AI באמזון ולייטריקס: האם AI הורג משרות?(12:14) - למה חברות AI FIRST יהרגו את תעשיית ה-SaaS?(24:21) - "כלכלת בחירות" והטבת המס (QSBS) שמושכת יזמים לדלאוור(37:14) - יזמים סדרתיים בישראל (Wiz, CyberArk)(57:08) - המבנה החדש של OpenAI: שווי 500 מיליארד דולר והעסקה עם מיקרוסופט
Welcome back to The Entrepreneur's Journey. In this episode, Jason Gabrieli sits down with John Cavanaugh, CPA and tax attorney at Firenze Advisors, to discuss the foundational role that legal entity structure plays throughout the life of a business—from launch to scale to exit. They explore common pitfalls, how to adjust structures as businesses grow, and key planning considerations for exits, succession, and estate transitions. If you're a business owner thinking about growth or preparing for a future sale, this episode is packed with practical knowledge.Tune into this episode to also learn:● Why your legal entity structure isn't just paperwork—but the core of your business.● How and when to shift from LLC to S-Corp or C-Corp status.● The role of installment sales, trust planning, and QSBS in reducing tax liability.● What business owners often overlook when preparing for a sale or succession.What we discussed● [00:01:36] Why entity structure is foundational—and what most owners overlook.● [00:03:16] How and why business structures should evolve over time.● [00:05:06] The niche John fills: strategic planning across legal and tax.● [00:06:54] Real estate and multi-entity structures: liability and tax traps to avoid.● [00:09:01] Debt, partners, and why cross-collateralization needs careful planning.● [00:10:40] Transitioning a business: selling to outsiders vs. keeping it in the family.● [00:13:03] What surprises owners during due diligence and how to be prepared.● [00:16:45] Why planning ahead matters: using trusts and state residency smartly.● [00:18:11] Charitable trust and life insurance planning to reduce estate tax.● [00:20:31] Holding company structures: when and why to consider one.● [00:24:31] What clients usually miss: books, documentation, and cleanup.● [00:26:24] Installment sale example that saved significant taxes.● [00:30:07] Managing wealth post-sale and preserving it for future generations.● [00:32:06] The power of looking at your structure every 2–3 years.3 Things To RememberYour legal and tax entity structure should evolve as your business grows.Planning for sale or succession starts years in advance—don't wait.Holding companies, trusts, and installment strategies can drastically reduce taxes and protect assets.Useful LinksConnect with Jason Gabrieli: jgabrieli@HFMadvisors.com | LinkedInLike what you've heard… Learn more about HFM HERE Schedule time to speak with us HERE
In this week's episode of Business Lunch, Roland Frasier and Ryan Deiss continue breaking down the “Bottlenecks” framework—the 11 proven playbooks that billionaires use to grow, protect, and multiply wealth.From AI-driven acquisitions to tax-optimized exits, this conversation dives into the strategies that separate ordinary entrepreneurs from long-term empire builders. You'll hear how the world's wealthiest think about capital allocation, scaling “boring” businesses, and structuring companies for massive, tax-efficient exits.Whether you're scaling your first venture or managing a growing portfolio, this episode is a tactical deep dive into how to think—and act—like a billionaire.Key Takeaways • Tech Is Not a Moat: With AI making innovation easy to copy, your real advantage is distribution and users. • The QSBS Advantage: How the Qualified Small Business Stock exemption can eliminate up to $10M (or more) in capital gains per shareholder. • DAFs & Charitable Strategy: Donor Advised Funds can combine tax savings with long-term impact—if structured correctly. • Boring Businesses, Billionaire Results: Logistics, energy, and real estate can quietly create generational wealth when value is added and scaled. • Capital Cycling: Why the world's best investors (like Blackstone and Berkshire) act like banks—recycling capital and compounding returns.Episode Highlights [00:02:00] – Why tech is easy to copy—and why users, not code, create real enterprise value. [00:10:00] – The billionaire tax play: how QSBS and DAFs legally minimize or eliminate capital gains. [00:18:00] – When to start thinking about tax strategy (hint: usually not before $10M net worth). [00:25:00] – Logistics, land, and “boring” businesses that create quiet fortunes. [00:33:00] – The ESG arbitrage: adding sustainability to raise valuations. [00:40:00] – Network effects and marketplace rollups: creating compounding flywheels. [00:55:00] – The rise of “edge retail”: micro-brands, coffee chains, and inversion models that scale fast. [01:05:00] – Capital cycling and other people's money (OPM): how billionaires play the funding game.Memorable Quotes“If all you are is a feature that someone else could build, you don't have a business—you have a countdown clock.”“Boring businesses aren't boring when they compound quietly into billions.”“It's not what you make—it's what you keep.”“Billionaires don't think like operators; they think like capital allocators.”Mentioned in This EpisodeQualified Small Business Stock (QSBS) – U.S. tax exemption strategyDonor Advised Funds (DAFs) – Philanthropic and tax planning vehiclesRoss Perot Jr. – Logistics real estateDutch Bros – Scalable retail model exampleBlackstone & Berkshire Hathaway – Capital cycling and compounding modelsListen If You'reA founder or investor learning to structure smarter deals.A CEO or operator ready to scale beyond execution into capital allocation.A strategic thinker who wants to play the long game in business and wealth creation.ConnectHosts: Roland Frasier & Ryan DeissPodcast: Business Lunch with Roland FrasierMore at: businesslunchpodcast.comMentioned in this episode:Join Roland & Ryan at Get Scalable LiveIf you're a founder, CEO, or operator running a 7- or 8-figure business, Get Scalable Live was built for you. This is not your typical business event. It's 3 days of hands-on strategy, real-world frameworks, and next-level networking with the smartest operators in the game.
Dan Gray is the Head of Insights at Equidam.If you're a tech and investing nerd like us, you'll love this conversation. We cover everything Dan's learned reading dozens of academic research papers on startups and venture capital, debunking many popular narratives of the industry.We talk about the dangers of pre-mature startup scaling, the importance of origination stage investing, the concept of startup catering and why so many startups look the same, and the role of mega funds play in the ecosystem.We also discuss what the data says about concentration vs diversification, what VC's get wrong about pattern matching, and why pivoting is more valuable than you thinkThanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTry Harmonic - The startup discovery engine https://harmonic.ai/turnerTimestamps:(6:43) What's the required rate of return in VC?(9:29) Venture capital needs new definitions(16:10) QSBS(18:23) Are we in an AI bubble?(24:07) Re-branding early and late stage venture(28:25) We need more origination stage capital(40:05) Survivorship bias in emerging manager outperformance(42:57) Incentives driving larger fund sizes(48:10) Raising overvalued rounds re-risks a startup(52:08) Startup catering: why all startups look alike(58:42) Are VC mega funds still an experiment?(1:08:06) Late stage VC is competing with PE(1:13:42) a16z's Fund 1 strategy(1:18:18) How diversified should VC funds be?(1:25:06) Performance of Generalist vs Specialist firms(1:30:35) How to value a startup(1:40:58) Why VC firm location correlates to returns, but startup location does not(1:44:05) Founder background doesn't predict success(1:48:27) Startups with one pivot are most successful(1:50:24) Premature scaling kills 70% of startups(1:54:47) Does mega fund model work for origination investing?(1:56:15) Value of Twitter and writing onlineReferenced Research PapersVenture Predation: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4437360Process Alpha: https://angelspan.com/process-alpha-how-to-construct-and-manage-optimized-venture-portfolios-joe-milam-journal-of-portfolio-management-august-2022/The Sunk Cost Fallacy in VC: https://www.sciencedirect.com/science/article/pii/S0929119924000518Predictably Bad Investments in VC: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4135861Startup Catering to Venture Capitalists: https://afajof.org/management/viewp.php?n=58968Premature Scaling: https://innovationfootprints.com/wp-content/uploads/2015/07/startup-genome-report-extra-on-premature-scaling.pdfReferenced BooksThe Otherland Tetrology: https://www.goodreads.com/series/43762-otherlandPermutation City: https://www.goodreads.com/book/show/156784.Permutation_City?from_search=true&from_srp=true&qid=lf7FuUR9se&rank=1Necromancer: https://www.goodreads.com/book/show/6088007-neuromancer?ref=nav_sb_ss_1_29Other Referenced ItemsQSBS changes: https://www.dwt.com/blogs/startup-law-blog/2025/07/qsbs-big-beautiful-bill-tax-code-upgradesMega funds and the great re-risking: https://nextview.vc/blog/megafunds-and-the-great-re-risking/Rex Woodbury's post on hot companies: https://www.digitalnative.tech/p/the-taxi-cab-theory-of-venture-capitalThe VC Performance Paradox: https://www.linkedin.com/pulse/performance-paradox-venture-capital-dan-gray-2fqrePrior episodes mentionedDan Feder: https://youtu.be/_Ou6D9PLSBIMichael Dempsey: https://youtu.be/UzSbG6DL8CMSolugen: https://youtu.be/ofkNiB2nI3QFollow DanTwitter: https://x.com/credistickBlog: https://credistick.comFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
Welcome back to another episode of The Richer Geek Podcast! Today our guest is David Flores Wilson, founder of Sincerus Advisory and named an Investopedia Top 100 Financial Advisor. He helps entrepreneurs, tech professionals, and business owners maximize wealth, optimize equity compensation, and exit businesses the smart way. In this episode, David breaks down tax-saving strategies, the power of donor-advised funds, how to use real estate for wealth building, and why exit planning should start on day one, not the day you're ready to sell. If you want to keep more of what you earn and create a lasting financial plan, this conversation is a must-listen. In this episode, we chat about… How David's early experiences with family businesses shaped his career in financial planning. Why entrepreneurs need a different approach to financial planning than traditional employees. Strategies for deferring taxes and leveraging state residency for long-term savings. Understanding Qualified Small Business Stock (QSBS) and how it can save millions in taxes. The role of charitable giving strategies (like DAFs and charitable buyouts) in wealth preservation. Why exit planning should start when you form your business, not when you're ready to sell. How to balance wealth-building in real estate vs. stocks based on personal skills and opportunities. The emotional and identity shifts entrepreneurs face when selling a business. Key Takeaways: Entrepreneurs often need customized financial planning because most of their wealth is tied to their business. Tax deferral strategies can provide huge advantages, especially when combined with residency planning. QSBS can exempt up to $10 million in capital gains if structured correctly, an often-overlooked opportunity. Charitable giving can be structured to maximize both impact and tax benefits (e.g., bunching, DAFs, charitable redemptions). Real estate offers unique tax advantages but requires clear strategy and sometimes specialized partners. Exit planning isn't just about money, it's about legacy, lifestyle, and identity after the sale. Resources from David LinkedIn | Sincerus Advisory | Blog: Planning to Wealth Resources from Mike and Nichole Gateway Private Equity Group | Nic's guide
Did you know that a tax benefit, the Qualified Small Business Stock (QSBS) tax exclusion, can save you millions? Discover how properly structuring your company from the start can lead to a tax-free sale of your C Corporation, potentially saving you millions. You'll learn the crucial steps to take now to prepare for a successful and highly profitable exit later. View the complete show notes for this episode. Want To Learn More? Allocation of Purchase Price & Taxes When Selling a Business Business Exit Plan & Strategy Checklist | A Complete Guide Why You Need to Consider Taxes Before Selling Your Business Additional Resources: Selling your business? Schedule a free consultation today. Sign up for an Assessment and Valuation of Your Business. Courses: The Art & Science of Selling a Business Download The Art of The Exit: The Complete Guide to Selling Your Business Download Acquired: The Art of Selling a Business With $10 Million to $100 Million in Revenue If you have any topic or guest suggestions, please email them to podcast@morganandwestfield.com.
Explore OB3 Act changes to QSBS rules, including the new $75M limit, $15M exclusion, and strategies to maximize tax savings for founders and investors. The American College of Trust and Estate Counsel, ACTEC, is a professional society of peer-elected trust and estate lawyers in the United States and around the globe. This series offers professionals best practice advice, insights, and commentary on subjects that affect the profession and clients. Learn more in this podcast.
Send us a textSome entrepreneurs sell their companies and walk away with zero federal taxes. How? This is thanks to a strategy called QSBS.In this episode, tax strategist Alessandro of Get Dynasty breaks down Qualified Small Business Stock, new changes from the “Big Beautiful Bill,” and how founders can use trusts to multiply tax-free exits. If you're building or investing in startups, this could be the single most powerful tax break you'll ever use.
Welcome back to Belk on Business! I'm Josh Belk, and in today's episode, I'm diving into a new set of provisions from the recently passed “Big Beautiful Bill.” We're shifting gears from the last few episodes and breaking down five key areas: tax relief on overtime pay, updated estate and gift tax exemptions, gambling deduction limits, changes to qualified small business stock, and updates to FMLA and meal deductions.Whether you're an employer managing payroll, a high-net-worth individual planning your estate, or a business owner looking at stock-based growth, there's something in here that can affect your planning and your bottom line. Let's get into the details.3 Key TakeawaysNo Tax on Overtime (2025–2028): Employees in tip-eligible industries can deduct the overtime portion of their pay (above their normal rate) up to $12.5K (single) or $25K (joint), regardless of itemizing.Estate Tax Exemption Raised: The federal estate and gift tax exclusion jumps to $15M (plus inflation), giving families and high-net-worth individuals more room to plan.QSBS Gains Can Be Excluded: Qualified Small Business Stock purchased after July 1, 2025, may offer up to 100% capital gains exclusion if held for five years, or rollover options similar to a 1031 exchange.Episode Timeline & Highlights[0:00] - Recap of previous episodes and what's new in this one[1:15] - No tax on overtime explained: who qualifies and what's deductible[3:25] - Example breakdown of how overtime deduction works[6:32] - Employer payroll implications and what reporting might look like[6:57] - Estate and gift tax exemption increased to $15M[8:54] - Gambling losses now limited to 90% of winnings[10:04] - What is Qualified Small Business Stock (QSBS) and how gain exclusions apply[11:42] - Eligibility rules for QSBS, asset limits, and holding period[14:00] - Family Medical Leave Act credits made permanent[14:54] - Meal deduction changes—who still qualifies for 100%Links & ResourcesIRS Guidance on Overtime Tax Treatment (coming soon)Estate & Gift Tax Overview: https://www.irs.gov/businesses/small-businesses-self-employed/estate-and-gift-taxesQualified Small Business Stock (QSBS) Rules: https://www.irs.gov/pub/irs-drop/n-18-48.pdfFamily and Medical Leave Credit Info: https://www.irs.gov/newsroom/employer-credit-for-paid-family-and-medical-leaveIf this episode gave you a clearer understanding of the new tax provisions, don't forget to rate, follow, and review Belk on Business. And share it with a colleague or business owner who should be planning ahead. Until next time—stay smart and strategic.
In this episode of Future Focused: Sophisticated Estate Planning, hosts Michael Clear and Erin Nicholls are joined by Corporate Partners Scott McClure and Len Gray to discuss how the One Big Beautiful Bill Act (OBBBA) is expanding opportunities with qualified small business stock (QSBS). OBBBA brought about key updates to QSBS, including an increased capital gain exclusion amount, a higher asset threshold for a company to qualify as a small business, and reduced holding periods. Tune in, as this conversation emphasizes the importance of proactive tax planning for founders and business owners to maximize their benefits under this new legislation.
Group Chat News is back with the hottest news of the week including Trump calls Elon's third party "ridiculous." Your kid is getting a ‘Trump account.' Should you put your money in it, Trump's One Big Beautiful Bill Act (OBBBA) offers an incredible incentive to startup founders and early employees with more lenient QSBS, President Trump announces plans for UFC fight on White House grounds in honor of America 250, TikTok Building New Version of App Ahead of Expected U.S. Sale, China Plans Nationwide Subsidies to Boost Birthrate.
Today's show:Startup exits are heating up with $67.7B in Q2 activity, QSBS just got a major expansion, and Robinhood is pushing boundaries with tokenized SPVs. In this episode, @Jason and @alex break down what it all means for founders and investors, plus the rise of Elon's “America Party,” TikTok's potential reboot, and why SaaS startups must rebrand around AI to stay competitive. A must-watch for anyone building, investing, or navigating tech in 2025.Timestamps:(04:29) Jason's thoughts on Elon Musk's America Party(10:05) Oracle - Try OCI and save up to 50% on your cloud bill at https://www.oracle.com/twist(15:02) M&A keeps heating up and why a big fintech IPO could be on the way!(20:00) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist(26:32) Unpacking liquidation preferences for non-experts(29:11) AI companies are soaking up the majority of investment dollars but what does that really MEAN?(30:02) MonarchMoney - Get 50% off your first year by going to MonarchMoney.com and using the offer code TWiST(36:26) Why Jason's group chat will love the QSBS expansion but it's not really that big of a deal…(46:27) TikTok seems poised to make a deal… Why Jason thinks they do pose a national security threat.(59:22) Why is CoreWeave picking up Core Scientific, and is now a good time to sell your shares?Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisThank you to our partners:(10:05) Oracle - Try OCI and save up to 50% on your cloud bill at https://www.oracle.com/twist(20:00) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist(30:02) MonarchMoney - Get 50% off your first year by going to MonarchMoney.com and using the offer code TWiST.Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarlandCheck out Jason's suite of newsletters: https://substack.com/@calacanisFollow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
© 2020-2026 Ivy Podcast Discovery LLC
