Podcasts about business lunch

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Best podcasts about business lunch

Latest podcast episodes about business lunch

Business Lunch
The CFO Reality Check Every Entrepreneur Needs: Leading Through the Numbers

Business Lunch

Play Episode Listen Later Dec 11, 2025 43:58


In This Episode of Business Lunch, join Ryan Deiss and I in this enlightening episode of Business Lunch, where they delve into the often overlooked yet crucial topic of accounting and finance. We discuss how entrepreneurial optimism can clash with the harsh realities of financial reporting. Learn how to navigate these challenges and foster a productive relationship with your CFO to ensure your company's financial health.Timestamps:00:00 – Entrepreneurial Optimism vs. Financial Realism01:36 – Why Accounting Reporting Shapes Company Culture02:37 – Switching from Cash to Accrual Accounting03:17 – When Financial Reports Become Depressing05:41 – Fixing the Reporting Process08:29 – Avoiding Obstacles: A Common Entrepreneurial Pitfall09:54 – Support Your Team… or Change It12:19 – Leadership's Role in Financial Clarity17:34 – Preparing for Exit & Upgrading the Finance Team20:17 – Why Accounting Method Changes Can Distort Profit27:03 – Restructuring Contracts to Fix Revenue Recognition31:54 – Challenging Accounting Assumptions37:15 – The Importance of Cash Flow Over Profit40:54 – Don't Let Accounting Wag the Dog43:10 – Final Thoughts & OutroConnect with me on social:TikTok: Check out my TikTok HereInstagram: Check out my Instagram HereFacebook: Check out my Facebook HereLinkedIn: Check out my LinkedIn HereSubscribe to my YouTube

Business Lunch
The Cash Flow Reality Check Every Business Owner Needs

Business Lunch

Play Episode Listen Later Dec 5, 2025 59:19


In this episode of Business Lunch, we walk you through the ins and outs of managing business finances. We explain the potential pitfalls of keeping more than a month's worth of operating expenses in the account. We explain how that can lead to complacency and unnecessary spending. We also explain how business can cover unexpected events and tricky payroll situations, like those pesky months with three payroll cycles or prepaying for holidays. We go beyond the glamor of being an entrepreneur to the real details behind the scenes.Highlights:"We're very big on lifestyle and freedom and all those kinds of things. But it's also important to acknowledge that it's not a perfect situation very often.""There are times when things are absolutely amazing. And there's times when things could frankly be a hell of a lot better. And I think that's called life. I think that's called entrepreneurship""If we're buying a business, I hate the agreement part. I love negotiation and strategy. But when it comes to reading a 75-page document, I just absolutely can't stand it."Timestamps:00:00 - Operating Account Insight01:15 - Personal Calendar Reflection02:15 - Acknowledging Imperfections03:15 - Loving Strategy but Hating Legal Work06:52 - The Reality of Entrepreneurship07:39 - Cyclicality in Business08:54 - Handling Excess Profit10:20 - Minimum Operating Reserve10:37 - Importance of Operational Cash10:44 - Prepaying Payroll ChallengesConnect with me on social:TikTok: Check out my TikTok HereInstagram: Check out my Instagram HereFacebook: Check out my Facebook HereLinkedIn: Check out my LinkedIn HereSubscribe to my YouTube

Wintrust Business Lunch
Noon Business Lunch 12/5/25: The Holly House, Uniting Voices Chicago, and the hottest holiday gifts with Abt electronics

Wintrust Business Lunch

Play Episode Listen Later Dec 5, 2025


Wendy Snyder steps in for John Williams on today’s Noon Business Lunch! Segment 1: Samantha Frontera, Co-Owner, The Holly House, a mother–daughter–built boutique that celebrates local artisans, meaningful moments, and the kind of small-town magic you can actually feel. Segment 2: Jospehine Lee, president of Uniting Voices Chicago, a nonprofit that provides music education and performance opportunities […]

Wintrust Business Lunch
Noon Business Lunch 12/4/25: Housing affordability, market optimism, transitioning economy

Wintrust Business Lunch

Play Episode Listen Later Dec 4, 2025


Segment 1: Jeff Ostrowski, Analyst, Bankrate, joins John to talk about why first-time homebuyers keep getting older. Segment 2: Faron Daugs, CFP, Founder and CEO, Harrison Wallace Financial Group, to talk about what he expects from the inflation and consumer sentiment data released tomorrow, how people are still feeling the impact of inflation, if we will see some tariff […]

Business Lunch
Why the First One-Person Billion-Dollar Company Is Closer Than You Think

Business Lunch

Play Episode Listen Later Dec 3, 2025 15:50


In this episode of Business Lunch, we dive into extreme leverage—how solo founders are building multi-million dollar businesses with basically zero headcount. We break down the playbook: finding expensive problems, validating demand before writing code, and letting AI handle the execution. We also cover the risks, the new KPIs that matter, and the vision of one founder running a portfolio of micro businesses on a single AI-driven back office.Chapters00:00 Building a Billion Dollar AI Company Alone13:18 Leveraging AI for Business Solutions13:45 Redefining Roles in the Age of AISpecial AnnouncementAfter 5 years of teaching entrepreneurs how to build, buy, and sell companies, I'm retiring all Epic courses and educational content permanently. This isn't because they didn't work, thousands have built real wealth with these frameworks, but because AI, capital markets, and collaboration have changed the game. I'm shifting from teaching deals to doing deals. Want access to everything before it disappears forever? This is your last chance to grab 5 years of proven frameworks, strategies, and training materials before they're gone for good. See the full story and whats going into the vault here: Go to the vaultConnect with me on social:TikTok: Check out my TikTok HereInstagram: Check out my Instagram HereFacebook: Check out my Facebook HereLinkedIn: Check out my LinkedIn HereSubscribe to my YouTube

Wintrust Business Lunch
Noon Business Lunch 12/3/25 – Terry Savage: How ‘Trump Accounts' will work

Wintrust Business Lunch

Play Episode Listen Later Dec 3, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about Medicare Open Enrollment ending, what you should know about ‘Trump accounts’ and how they will work, and why she always adheres to Warren Buffet’s advice that, ‘nobody ever got rich betting against America.’ Terry also suggests you visit her Year-End Planning Checklist.

Wintrust Business Lunch
Noon Business Lunch 12/2/25: Ghost jobs, Giving Tuesday, market opportunity

Wintrust Business Lunch

Play Episode Listen Later Dec 2, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins John to talk about the health of the labor market, how companies have job listings for positions that are never filled, and the issues that companies have with the amount of applicants who aren’t qualified. Also, Tom weighs in on the overall health of the […]

Wintrust Business Lunch
Noon Business Lunch 12/1/25: Cyber Monday, Cameo's court win, Broken Oar Arctic Winter Bar

Wintrust Business Lunch

Play Episode Listen Later Dec 1, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media, joins John Williams to talk about what we can expect from Cyber Monday this year. Ilcye also reminds you to spend your FSA balance, and the state of Florida looking to eliminate property taxes for residents. Segment 2: Jim Dallke, Director of Communications, TechNexus Venture Collaborative, tells John about Cameo scored a […]

Business Lunch
The 90-Day Proof Pack: How PE Firms Engineer Instant Value

Business Lunch

Play Episode Listen Later Nov 27, 2025 21:56


In this episode of Business Lunch, we dive into the critical 90 to 100-day period following a private equity acquisition, emphasizing the need for rapid, auditable value creation. It outlines a strategic framework for CFOs, detailing tactical moves to achieve immediate financial impact while integrating lean thinking principles to eliminate waste and enhance operational efficiency. The discussion also highlights the importance of human behavior in executing these strategies effectively.Chapters00:00 The Critical 90-Day Sprint10:05 Strategic Framework for CFOs18:37 Tactical Moves for Immediate ImpactSpecial AnnouncementAfter 5 years of teaching entrepreneurs how to build, buy, and sell companies, I'm retiring all Epic courses and educational content permanently. This isn't because they didn't work, thousands have built real wealth with these frameworks, but because AI, capital markets, and collaboration have changed the game. I'm shifting from teaching deals to doing deals. Want access to everything before it disappears forever? This is your last chance to grab 5 years of proven frameworks, strategies, and training materials before they're gone for good. See the full story and whats going into the vault here: Go to the vaultConnect with me on social:TikTok: Check out my TikTok HereInstagram: Check out my Instagram HereFacebook: Check out my Facebook HereLinkedIn: Check out my LinkedIn HereSubscribe to my YouTube

Wintrust Business Lunch
Noon Business Lunch 11/26/25 – Terry Savage: Big markets swings are concerning

Wintrust Business Lunch

Play Episode Listen Later Nov 26, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about the markets bouncing back of late, what concerns her about the market moving forward, why consumer confidence has faltered, and if the Fed will cut interest rates again in December, and why Thanksgiving is a good time to have the ‘bills and wills’ conversation. Terry […]

Wintrust Business Lunch
Noon Business Lunch 11/25/25: Work communication, ‘overqualified' job seekers, Black Friday streaming deals

Wintrust Business Lunch

Play Episode Listen Later Nov 25, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins John to talk about the importance of effective communication in the workplace. Segment 2: Philippe Weiss, President, Seyfarth at Work, joins John to talk about the risks involved in rejecting job candidates who are ‘overqualified’ for a position. Segment 3: Longtime Chicago radio veteran Harvey Wells, Founder, Lower […]

Wintrust Business Lunch
Noon Business Lunch 11/24/25: Thanksgiving costs, home prices drop, Abbott buys Exact Sciences

Wintrust Business Lunch

Play Episode Listen Later Nov 24, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media, joins John Williams to talk about the cost of Thanksgiving this year, home buyers seeing record discounts, and why you should always ask for a discount. Segment 2: Jim Dallke, Director of Communications, TechNexus Venture Collaborative, tells John about EV startup Harbinger raising $160M to bring EVs to the medium-duty truck space, […]

Wintrust Business Lunch
Noon Business Lunch 11/21/25: Rate cut coming, consumer sentiment slides, EV sales

Wintrust Business Lunch

Play Episode Listen Later Nov 21, 2025


Segment 1: Craig Bolanos, Founder and Wealth Advisor at VestGen Wealth Partners, joins John Williams to talk about the likelihood we see an interest rate cut in December, why the stock market likes the idea of a rate cut, where people should be putting their money considering the volatility in the market, why consumer sentiment is down, his […]

Business Lunch
Identity Trust: Why 125 Years of Marketing Just Died

Business Lunch

Play Episode Listen Later Nov 20, 2025 36:51


In this episode of Business Lunch, Roland Frasier and Ryan Deiss discuss the evolving landscape of the customer journey, emphasizing the importance of trust in modern marketing. They explore how traditional stages of the buying process are being replaced by a more fluid approach, where trust becomes the key driver of transactions. Through case studies and examples, they highlight the significance of identity trust, authenticity, and the role of founders as trust agents in building strong connections with consumers. The conversation also touches on the challenges and strategies for effectively engaging audiences in both B2B and B2C contexts.Chapters00:00 The Death of the Traditional Customer Journey02:51 The Role of Trust in Modern Marketing06:09 Case Studies: Successful and Controversial Campaigns09:05 Identity Trust: Connecting with Consumers11:57 The Power of Authenticity in Advertising14:56 Building Trust in B2B vs B2C17:59 Actionable Strategies for Trust Building20:47 The Importance of Founders as Trust AgentsSpecial AnnouncementAfter 5 years of teaching entrepreneurs how to build, buy, and sell companies, I'm retiring all Epic courses and educational content permanently. This isn't because they didn't work, thousands have built real wealth with these frameworks, but because AI, capital markets, and collaboration have changed the game. I'm shifting from teaching deals to doing deals. Want access to everything before it disappears forever? This is your last chance to grab 5 years of proven frameworks, strategies, and training materials before they're gone for good. See the full story and whats going into the vault here: Go to the vaultConnect with me on social:TikTok: Check out my TikTok HereInstagram: Check out my Instagram HereFacebook: Check out my Facebook HereLinkedIn: Check out my LinkedIn HereSubscribe to my YouTube

Wintrust Business Lunch
Noon Business Lunch 11/20/25: Jobless boon, Gemini 3, Addison Business Exchange

Wintrust Business Lunch

Play Episode Listen Later Nov 20, 2025


Segment 1: Michelle Seiler, Real Estate Agent at Century 21, and President of the Addison Business Exchange, talks to John about the work that the Addison Business Exchange does, how the real estate market is doing in Addison, the impact interest rates are having on the real estate market, and why Addison is such a […]

Wintrust Business Lunch
Noon Business Lunch 11/19/25 – Terry Savage: Big ‘ifs' hanging over the market

Wintrust Business Lunch

Play Episode Listen Later Nov 19, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about why everybody is watching Nvidia earnings, why the market has dipped recently, the two big ‘ifs’ hanging over the market, and what to know about RMD time. Terry, as always, answers all of your financial questions.

Business Lunch
Navigating Business Transitions: From Epic to Scalable

Business Lunch

Play Episode Listen Later Nov 18, 2025 58:04


In this episode of Business Lunch, Roland Frasier and Ryan Deiss discuss the recent transition from Epic Network to a more focused approach with the Scalable Company. They explore the challenges of running a business that has taken on a life of its own, the importance of making changes when a business no longer serves its founders, and the evolving landscape of course creation in the age of AI. The conversation emphasizes the need for entrepreneurs to take action, embrace change, and focus on what truly brings them joy in their business endeavors.Chapters00:00 Introduction and Context of Change03:02 The Evolution of Epic Network05:58 The Decision to Pivot: Why Change is Necessary08:53 Understanding Business Ownership and Personal Happiness11:48 The Importance of Knowing What to Exit To14:56 The Future of Course and Information Businesses21:05 Lessons Learned from the Epic Network Experience30:35 The Reality of Course Consumption33:10 Reflections on 2020 and Business Decisions36:07 Navigating Change and Decision-Making40:06 What Would Need to Be True?43:12 Future Plans and New Directions46:24 Final Thoughts and Messages to the CommunitySpecial AnnouncementAfter 5 years of teaching entrepreneurs how to build, buy, and sell companies, I'm retiring all Epic courses and educational content permanently. This isn't because they didn't work, thousands have built real wealth with these frameworks, but because AI, capital markets, and collaboration have changed the game. I'm shifting from teaching deals to doing deals. Want access to everything before it disappears forever? This is your last chance to grab 5 years of proven frameworks, strategies, and training materials before they're gone for good. See the full story and whats going into the vault here: Go to the vaultConnect with me on social:TikTok: Check out my TikTok HereInstagram: Check out my Instagram HereFacebook: Check out my Facebook HereLinkedIn: Check out my LinkedIn HereSubscribe to my YouTube

Wintrust Business Lunch
Noon Business Lunch 11/18/25: Market drop, tariff rollback, Thanksgiving spending

Wintrust Business Lunch

Play Episode Listen Later Nov 18, 2025


Segment 1: Ryan Messner, President of Long Grove's Historic Downtown Business Association, joins John Williams to talk about all the holiday festivities the town has planned for the upcoming holidays. Segment 2: Matt Schultz, LendingTree Chief Consumer Finance Analyst, talks with John about a new Lending Tree survey that shows Thanksgiving hosts are expected to spend an average of $487 […]

Wintrust Business Lunch
Noon Business Lunch 11/17/25: Home values, property tax jump, Chicago conventions

Wintrust Business Lunch

Play Episode Listen Later Nov 17, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media, joins John Williams to talk about 53% of U.S. homes losing value in the past year, and some Chicago homeowners seeing a sizeable jump in their property taxes. Segment 2: Jim Dallke, Director of Communications, TechNexus Venture Collaborative, tells John about Rivian Automotive announcing a spin off company called Mind Robotics, […]

Wintrust Business Lunch
Noon Business Lunch 11/14/25: Retirement planning, property taxes, zoom towns, and holiday shopping trends

Wintrust Business Lunch

Play Episode Listen Later Nov 14, 2025


Segment 1: Brian Speers, Wealth Management Advisor at Merrill Lynch joins John joins John to break down retirement planning strategies across generations, from Gen Z just starting out to Baby Boomers watching their spending in retirement. Brian explains why tackling high-interest debt first, using Roth accounts early, and building long-term saving habits can make all the […]

Wintrust Business Lunch
Noon Business Lunch 11/12/25 – Terry Savage: Why you should wait to take Social Security

Wintrust Business Lunch

Play Episode Listen Later Nov 12, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about maximizing your social security. And John and Terry are delighted to be joined by Laurence Kotlikoff, professor of economics at Boston University, president of Economic Security Planning, and a New York Times best-selling author for today’s special edition of the Noon Business Lunch. Terry, John, […]

Wintrust Business Lunch
Noon Business Lunch 11/11/25: Hiring disconnect, work leadership, luxury home sales

Wintrust Business Lunch

Play Episode Listen Later Nov 11, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins John to talk about a recent speech he gave to Google about the disconnect between executives, managers and HR/ recruiting when it comes to hiring. Tom says communication without fear is what separates the good companies from the great companies. Segment 2: Philippe Weiss, President, Seyfarth at […]

Wintrust Business Lunch
Noon Business Lunch 11/10/25: Consumer debt, AI supercomputing, Fiserv Small Business Index

Wintrust Business Lunch

Play Episode Listen Later Nov 10, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media, joins John Williams to talk about the stock market being up a bit today, the latest on a possible end to the government shutdown, consumer debt being very high right now, and how ICE / Border Patrol activity is causing economic mayhem in certain areas of Chicago. Segment 2: Jim […]

Wintrust Business Lunch
Noon Business Lunch 11/7/25: Job layoffs, AI advances, AARP caregiving support

Wintrust Business Lunch

Play Episode Listen Later Nov 7, 2025


Segment 1: Craig Bolanos, Founder and Wealth Advisor at VestGen Wealth Partners, joins John Williams to talk about what’s weighing on the market this week, how the government shutdown has been impacting the economy, his thoughts on the Supreme Court hearing on the Trump administration’s tariff power, why he thinks the Fed will cut rates again in […]

Wintrust Business Lunch
Noon Business Lunch 11/6/25: Economic uncertainty, work loyalty, tariff impact

Wintrust Business Lunch

Play Episode Listen Later Nov 6, 2025


Segment 1: Steven Esposito, President of Yellowstone Wealth Management in Lake Forest, joins John to talk about why the market is pulling back a bit today, how uncertainty is impacting the economy, if he expect the Fed will cut rates again before the end of the year, the government shutdown slowing down the economy, the SCOTUS hearing […]

Wintrust Business Lunch
Noon Business Lunch 11/5/25 – Terry Savage: Worrisome signs for the stock market

Wintrust Business Lunch

Play Episode Listen Later Nov 5, 2025


Segment 1: Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about the market being up by a few hundred points today, why she’s concerned about the strength of the market, the importance of having ‘chicken money’ right now, and what you need to know about RMD time. And as always, Terry answers all of […]

Wintrust Business Lunch
Noon Business Lunch 11/4/25: Market pullback, shutdown impact, HumanWare

Wintrust Business Lunch

Play Episode Listen Later Nov 4, 2025


Segment 1: Phillip Shaw, CFP, Senior Advisor, Goldstone Financial Group, joins John Williams to talk about the stock market pulling back today, the impact of the government shutdown and the release of economic data, the latest on the administration’s trade deals, his concern about an AI bubble, the importance of getting a tax plan in order, and […]

Wintrust Business Lunch
Noon Business Lunch 11/3/25: SNAP funding, healthcare costs, Cameo suing OpenAI, Phraze

Wintrust Business Lunch

Play Episode Listen Later Nov 3, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media, joins John Williams to talk about the latest on the government shutdown, SNAP benefits, and the fight over the cost of Obamacare subsidies. Segment 2: Jim Dallke, Director of Communications, TechNexus Venture Collaborative, tells John about Cameo suing OpenAI for trademark infringement, and LinkedIn naming their top Chicago startups for 2025. […]

Wintrust Business Lunch
Noon Business Lunch 10/31/25: Strong market, AI v. bosses, Chicago budget impact

Wintrust Business Lunch

Play Episode Listen Later Oct 31, 2025


Segment 1: Paul Nolte, Senior Wealth Advisor and Market Strategist, Murphy & Sylvest, joins John to talk about monetary policy and Fed movement for the rest of the year, the market continuing to hit new highs, and where he suggests putting your money right now. Segment 2: Sarah E. Needleman, Leadership & Workplace Correspondent at Business […]

Wintrust Business Lunch
Noon Business Lunch 10/30/25: Monetary policy, tariff cost, Posto 31 in LaGrange Park

Wintrust Business Lunch

Play Episode Listen Later Oct 30, 2025


Segment 1: Jason Korinek, Executive Chef/Owner at Posto 31 in LaGrange Park, talks to John about where they are located in LaGrange Park, how long they have been in business, what the restaurant is most known for, how they use locally sourced products, the importance of making most of the items on the menu being […]

Wintrust Business Lunch
Noon Business Lunch 10/29/25 – Terry Savage: No big surprises from the Fed

Wintrust Business Lunch

Play Episode Listen Later Oct 29, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about today’s policy decision by the Federal Reserve, the stock market hitting all time highs, and some of the economic areas that she’s concerned about. Terry also answers all of your financial questions.

Wintrust Business Lunch
Noon Business Lunch 10/28/25: Amazon layoffs, meeting overload, Simple Flooring in Elk Grove Village

Wintrust Business Lunch

Play Episode Listen Later Oct 28, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins John to talk about Amazon announcing a new round of layoffs, and what corporate layoffs mean for the health of the economy. Segment 2: Philippe Weiss, President, Seyfarth at Work, joins John to talk about how numerous surveys have shown that managers who spend more time in […]

Wintrust Business Lunch
Noon Business Lunch 10/27/25: Market soars, China trade truce, Halloween spending rises

Wintrust Business Lunch

Play Episode Listen Later Oct 27, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media, joins John Williams to talk about the big stock market rally on Friday that continues today, the latest on a possible truce on China trade, the latest on the government shutdown and if their is an end in sight, and the impact of the SNAP program ending on November […]

Wintrust Business Lunch
Noon Business Lunch 10/24/25: Inflation climbs, Chicago sweets, Runaway Cow

Wintrust Business Lunch

Play Episode Listen Later Oct 24, 2025


Segment 1: Craig Bolanos, Founder and Wealth Advisor at VestGen Wealth Partners, joins John Williams to talk about the newest inflation data, why the market jumped today, his concern over debt, the overall strength of the economy, the latest on the government shutdown, the forecast for food prices, his expectations for Fed rate cuts for the rest […]

Wintrust Business Lunch
Noon Business Lunch 10/23/25: Cautious Fed, Loop activity, robot delivery

Wintrust Business Lunch

Play Episode Listen Later Oct 23, 2025


Segment 1: Michael Edwards, President and CEO, Chicago Loop Alliance, talks to John about Chicago Loop Alliance's State of the Loop quarterly report for the 3rd quarter of 2025. Segment 2: Abrar Al-Heeti, Senior Technology reporter for CNET, tells John about Waymo and DoorDash teaming up to deliver your food via Robotaxi, and OpenAI saying it is working with actors to […]

Wintrust Business Lunch
Noon Business Lunch 10/22/25 – Terry Savage: Don't take Social Security until age 70

Wintrust Business Lunch

Play Episode Listen Later Oct 22, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about why it is best to wait until you are 70 before taking Social Security (if you can!), what is going on with the price of gold, and to tell us what to know about Medicare Open Enrollment. And as always, Terry answers all of […]

Wintrust Business Lunch
Noon Business Lunch 10/21/25: Work hours, job search scams, rising streaming prices

Wintrust Business Lunch

Play Episode Listen Later Oct 21, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins John to talk about how many hours a week people should be working, if you need to be working more if you want to get ahead, and the rise of scammers preying on those looking for a job. Segment 2: Longtime Chicago radio veteran Harvey […]

Wintrust Business Lunch
Noon Business Lunch 10/20/25: Container homes, Chicago quantum hub, Halloween at Windy City Sweets

Wintrust Business Lunch

Play Episode Listen Later Oct 20, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media, joins John Williams to talk about her recent visit to SI Container Builds, who are doing remarkable things with used containers (40’x8′) and turning them into affordable housing.  Segment 2: Jim Dallke, Director of Communications, TechNexus Venture Collaborative, tells John about a French quantum company establishing its US headquarters in Chicago, Chicago […]

Wintrust Business Lunch
Noon Business Lunch 10/17/25: Fed cuts, market inflated, hot appliances, World's Fair exhibit

Wintrust Business Lunch

Play Episode Listen Later Oct 17, 2025


Segment 1: Steven Esposito, President of Yellowstone Wealth Management in Lake Forest, joins John to talk about how many interest rate cuts he expects before the end of the year, how the interest rate cuts could impact the economy, his concern over the banking system and credit markets, where he believes your money should be moved to, […]

Business Lunch
The Bottlenecks Billionaire Playbook: How the World's Richest Build, Scale, and Keep Their Fortunes

Business Lunch

Play Episode Listen Later Oct 16, 2025 40:11


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.

Wintrust Business Lunch
Noon Business Lunch 10/16/25: Markets stretched, Fed decision, Walmart and ChatGPT, Midwestern University

Wintrust Business Lunch

Play Episode Listen Later Oct 16, 2025


Segment 1: Tom Fortino, Founder and Principal, Alpha Wealth Group and host of “The Alpha Wealth Hour” on WGN Radio, joins John Williams to talk about the markets continuing to hold up despite economic uncertainty, if he thinks the market is a little bit stretched, earnings being strong, what the Fed is likely to do with rates, […]

Wintrust Business Lunch
Noon Business Lunch 10/15/25 – Terry Savage: Answering all your Medicare open enrollment questions

Wintrust Business Lunch

Play Episode Listen Later Oct 15, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about the delay in the Social Security cost-of-living increase announcement, and what to know about Medicare open enrollment. Terry has a three part series on everything you need to know here.

Wintrust Business Lunch
Noon Business Lunch 10/14/25: ‘Bed rotting,' fed staff cuts, hot U.S. housing markets

Wintrust Business Lunch

Play Episode Listen Later Oct 14, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins John to talk about labor market concerns, why hiring continues to remain flat, and the viral trend of ‘bed rotting.’ What does Tom make of the latest trend? Tom also stresses the need for stability from the government in order to keep the economy strong. […]

Wintrust Business Lunch
Noon Business Lunch 10/13/25: Affordable housing, small business survey, top holiday toys

Wintrust Business Lunch

Play Episode Listen Later Oct 13, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media, joins John Williams to talk about the winners of this year’s Nobel Prize for Economics, Broadcom and Open AI announcing a massive deal to build specific chips, the latest on the government shutdown, details of the Road to Housing Act, and a tour that she’s taking of a container […]

Wintrust Business Lunch
Noon Business Lunch 10/10/25: China tariff threat, skilled trade jobs, Chicago youth survey

Wintrust Business Lunch

Play Episode Listen Later Oct 10, 2025


 Segment 1: Phillip Shaw, CFP, Senior Advisor, Goldstone Financial Group, joins Jon Hansen to talk about today’s market dip, President Trump threatening higher tariffs on China, the disconnect between Main Street and Wall Street, why he believes the U.S. markets will continue to grow, consumer sentiment remaining pretty strong, the health of the economy overall, and what […]

Business Lunch
The Collapse of the Funnel: How Trust Now Drives Every Purchase

Business Lunch

Play Episode Listen Later Oct 9, 2025 42:21


In this episode of Business Lunch, Roland Frasier and Ryan Deiss explain how the classic four-stage buying journey has collapsed into one moment—and why trust is the lid that keeps prospects “popping” in your pot. They unpack three forms of trust—Identity, Competence, and Proximity—with sharp wins and public flops (Nike, Sephora, Peloton, DSW, Starbucks, Apple, United). You'll get simple creative frameworks to turn short-form content into instant, in-channel conversions and a 14-day sprint to prove it on a small budget.Highlights“It's not a funnel anymore—it's a popcorn popper. Your audience are kernels heating at different speeds. Trust is the lid that keeps them popping for you.”“Competence trust means the brand ‘gets me'—often better than I can describe myself.”“Employees outperform celebrities for reach and credibility—because most buyers are employees.”“Frictionless is forgettable. Add desirable friction that helps buyers name their pain and act.”“If you can't pivot your model, bolt trust into your media: mirror-micro-media, why-what-where, people-place-proof.”Mentioned in This EpisodeThree Trust Types (MAP mnemonic):M – Identity trust: Mirror → Micro → MediaA – Competence trust: “Answer” with Why → What → WhereP – Proximity trust: People → Place → ProofCompetence wins & misses: Nike's “Why do it?” repositioning; Sephora tutorials lifting AOV; Peloton's 2019 holiday ad backlash.Proximity plays: DSW AR try-ons; Starbucks barista TikToks; Apple retail specialists; cautionary tale—United Airlines viral incidents.Localization tactics: regional currency/sites, geo-specific visuals (city skylines), and micro-influencers by market.KPI effects: higher AOV/retention/loyalty from competence; higher LTV from proximity; employee posts driving outsized reach.Timestamps00:00 – The collapsed customer journey: from funnel to popcorn popper (trust as the lid)04:00 – Recap: Identity trust (mirror, micro, media)—and why episodes stand alone but compound07:30 – Competence trust: the brand that “gets me” (Nike shift, Sephora demos) + Peloton misread14:20 – Framework for competence: Why → What → Where (myth-bust, demo, direct CTA)17:30 – Example: 30-sec tax advisory myth-buster → LinkedIn/Reels → consult link → track AOV20:10 – Proximity trust: employees, in-place context, show real proof (DSW AR, Starbucks, Apple)24:10 – Employee content > celebrity polish; make it authentic, even shot on phone26:00 – 14-day Trust Sprint and MAP recap; why proximity is overlooked yet most scalableTakeaways for OperatorsStop chasing linear funnels; engineer trust in-channel so action can happen immediately.Use Why → What → Where to collapse steps: name the pain, show the fix, drop the link.Turn staff into a media network: People → Place → Proof with incentives and simple tracking.Localize by currency, domains, visuals, accents, micro-influencers—it quietly multiplies conversion.Run a 14-day sprint: baseline CAC/AOV → recruit 3 customers + 3 insiders → record shorts →...

Wintrust Business Lunch
Noon Business Lunch 10/9/25: Retirement tips, AI tasks, fall at Gallagher Way

Wintrust Business Lunch

Play Episode Listen Later Oct 9, 2025


Segment 1: Jordan Brummett, Senior Manager, Integrated Marketing at Marquee Development, tells Jon Hansen about all the great fall events happening at Gallagher Way! Segment 2: Jason Hiner, Editor in Chief, ZDNET, joins Jon to talk about ChatGPT having apps you can now chat with, and a Deloitte survey found that 86% of businesses use AI for […]

Business Lunch
The Subscription Trap: Why Recurring Revenue Isn't Always King.

Business Lunch

Play Episode Listen Later Oct 2, 2025 31:13


In this episode of the Business Lunch podcast, Host Roland Frasier and guest Richard Lindner break down the subscription trap and why recurring revenue isn't always the ultimate solution it's made out to be.From the outside, subscription models look like a dream: predictable cash flow, higher valuations, and a business that doesn't start at zero each month. But as Roland and Richard reveal, the reality can be far more complicated.They dive into real stories from their portfolio companies, showing how recurring revenue can backfire through hidden churn, customer support debt, and endless innovation demands. You'll hear how even big players like Netflix constantly battle to keep customers engaged, and why smaller businesses often underestimate the true cost of service.This episode is a must-listen if you're considering shifting to a subscription model—or if you've already launched one and want to make sure it's sustainable.HIGHLIGHTS“Recurring revenue is great… until you're losing more members each month than you know how to gain.”“There's voluntary churn, where people cancel. But the killer is involuntary churn—declined payments, expired cards—that can quietly eat your business alive.”“If you're creating content subscriptions, pair them with community. Access is the real value that keeps people sticking around.”“Don't fall in love with the model. Define your business by who you serve, not just how you charge.”Mentioned in this EpisodeThe difference between breakage vs. consumption models (think Netflix vs. gym memberships)Why AI in customer support is changing the economics of subscription businessesHow to tell if your business should pursue a bolt-on subscription or avoid it altogether

John Williams
Noon Business Lunch 9/30/25: Workplace values, CEO ‘Generation Skip,' retirement planning

John Williams

Play Episode Listen Later Sep 30, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins Jon Hansen, filling in for John Williams, to talk about why workplace values are holding up some younger workers. Segment 2: Philippe Weiss, President, Seyfarth at Work, joins Jon to talk about new trend where companies are either holding on to seasoned CEOs in their later 60s and […]

WGN - The John Williams Full Show Podcast
Noon Business Lunch 9/30/25: Workplace values, CEO ‘Generation Skip,' retirement planning

WGN - The John Williams Full Show Podcast

Play Episode Listen Later Sep 30, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins Jon Hansen, filling in for John Williams, to talk about why workplace values are holding up some younger workers. Segment 2: Philippe Weiss, President, Seyfarth at Work, joins Jon to talk about new trend where companies are either holding on to seasoned CEOs in their later 60s and […]