Podcasts about invest like

William Hockey is the co-founder of Plaid and the founder and CEO of Column, a software company that owns a bank and powers Ramp, Wise, Bilt, Mercury, and others. He funded Column by borrowing against his Plaid shares and has never raised outside capital.  William talks about what owning 100% of his company allows him to do that other venture-backed founder cannot and the personal risk he took to do so. He shares how Silicon Valley's consensus culture produces consensus founders, and why becoming a founder has become too safe. He believes the best builders are specialists and explains with unusual clarity what it takes to become the best in the world at one specific thing. William also spends a lot of time in emerging markets which has given him a unique perspective of the power of the US dollar. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.  ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp's⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠.  ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Rogo⁠ is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at ⁠Rogo.ai/invest⁠. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:02:43) Intro: William Hockey (00:03:49) Column: A Software Company That Owns a Bank (00:06:46) Finding Ideas in Emerging Markets (00:11:58) Why Constrained Societies Are More Innovative (00:16:02) What's Wrong With Silicon Valley (00:19:28) Building a Business Without Raising Money (00:22:48) What Venture-Backed Companies Can't Do (00:28:39) Getting Margin Called (00:31:41) Starting Companies Has Become Too Safe (00:34:23) Why Employees Take More Risks Than Founders (00:37:09) A Maniacal Commitment to Research (00:39:09) Finding Boring Problems to Solve (00:41:45) Why Building a Second Company is Easier (00:42:36) Missionary vs. Mercenary (00:45:49) Funding a Company with Cash Flows (00:50:04) Perspective on the Venture Ecosystem (00:52:48) The Dominance of the US Dollar (00:58:37) The Future of Financial Services (01:02:06) Why Big, Inefficient Brands Win From AI (01:06:29) The Opportunity for Non-Consensus Founders (01:08:03) The Kindest Thing

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you building wealth in the right order—or accidentally delaying the very foundation that makes bigger opportunities possible?If you're a business owner sitting on retained earnings, it's easy to treat every new opportunity like the priority—especially when real estate, acquisitions, or other growth plays look exciting. But this episode challenges a costly assumption: that a corporate wealth reservoir has to wait until after the next deal. Instead, it reframes that reservoir as the infrastructure that helps you pursue future opportunities with more control, liquidity, and long-term efficiency.In this episode, you'll hear how to:Rethink corporate-owned whole life insurance as foundational wealth infrastructure—not as a competing investment.Avoid the sequencing mistake that can quietly cost you years of compounding.Build a smarter capital strategy that supports liquidity, leverage, tax efficiency, and future investing flexibility.Press play to learn how to build your financial foundation first—so your next investment opportunity doesn't come at the cost of long-term wealth.

Thank you to our sponsors:Hungry Root - Get 40% off first box + free item in every box for life → https://www.hungryroot.com/gj using code GJBetter Help - Get 10% off therapy sessions → https://www.betterhelp.com/gjCure Hydration - Find on Amazon or local stores → https://www.curehydration.com/gjEarnin - Download app (App Store/Google Play), enter "Gin and Juice" under podcast when signing upIn this episode of Gin & Juice, Melissa and Mel kick things off by clapping back at anyone who thinks they don't look alike (spoiler: they're sisters, so duh). Melissa admits she's been "pre-luteal angry" all weekend and had to take herself to a nap like a cranky toddler.The sisters dive into legal tea with Brian Steele joining Lil Durk's defense team, then rave about seeing "Bigfoot" - Robin Thede's hilarious, politically-charged play in New York. The conversation takes a wild turn when they discover Shaquille O'Neal's insane investment portfolio (155 Five Guys, 40 gyms, Ring cameras, and apparently the reason we all need printer subscriptions). They joke about partnering with Shaq despite having a combined total of 25 cents between them.Melissa becomes volleyball's biggest advocate after watching Joe's tournament, declaring it more exciting than basketball and begging parents everywhere to keep their kids in the sport for scholarship opportunities. McKinley just started playing, and the family enthusiasm is infectious.Pop the Trunk segment brings complaints about nail salons (stop suggesting daisies!), restaurants changing menus (RIP California Pizza Kitchen's Jamaican Jerk Pizza), and a Labradoodle's year-long ear infection that cost $1,000+.The bulk of the episode breaks down Love is Blind's latest season with zero mercy:Emma gets dragged for saying yes despite not wanting kidsAlex H shows up to his own wedding looking homeless and gets righteously read at the altar by AshleyBrittany desperately clings to Devonte after he literally shakes her hand and says "we'll be in touch"The couple's therapy discussion reveals one man lied about a vasectomy for 20 years, another hasn't worked in 2 months but wants to buy an AudiThey wrap with a scathing review of Netflix's "Blue Therapy" - calling it an unfinished knockoff of Showtime's superior "Couples Therapy," where the therapist opens wounds and says "good luck!" before kicking couples out.Send Your Pop The Trunk Story: https://www.speakpipe.com/gjLet's Connect on Socials:- Instagram:  https://www.instagram.com/mrskevonstage/- TikTok:  https://www.tiktok.com/@mrskevonstage-Facebook: https://www.facebook.com/MrsKevOnStage-Patreon: https://www.patreon.com/c/kevonstagestudios-Business Inquires: hello@mrskevonstage.comShop My Outfits: https://www.liketoknow.it/mrskevonstage

Most real estate investors hit a ceiling — and they don't even know it. Lane Kawaoka scaled to 10,000 apartment units and over $1 billion in deals, and he's been completely transparent about what worked, what blew up, and what he's doing differently now.   In this episode, Lane breaks down his "Wealth Elevator" framework — the actual stages wealthy people climb through, from collecting rentals to syndicating commercial deals to investing alongside nine-figure family offices. He shares why the 2022 rate hike stopped him cold, why he's now buying businesses instead of chasing risky multifamily deals, and what average retail investors get dead wrong when evaluating syndications.   This one is packed. No fluff.  

Maybe you should invest like a dead man. Sounds crazy, right? But studies have shown accounts belonging to dead people often outperform those that are actively managed.  In this episode of the Midweek Memo podcast, host Mike Maharrey makes sense out of this phenomenon and explains why it's particularly valuable to understand during a war. He also highlights how the ongoing conflict with Iran is causing logistical disruptions to the precious metals markets, and speculates how the war could impact gold and silver prices down the road. 

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereDo you really need $5 million in cash to be financially free—or is that number missing the bigger point?Many people hear bold retirement numbers from wealthy entrepreneurs and assume financial freedom is a fixed target. But the real question isn't just how much money you have—it's how much liquid, flexible capital you control. Without that buffer, investing can feel risky, market swings become stressful, and opportunities pass you by. Understanding your personal “wealth reservoir” could be the difference between constantly worrying about money and confidently making financial decisions.In this episode, you'll discover:Why the famous $5 million rule is less about the number and more about creating true financial flexibility.How a wealth reservoir (your “sleep-at-night” money) allows you to invest, take risks, and weather downturns with confidence.The different places your liquidity can live—from home equity and cash accounts to insurance strategies and other safe assets.Press play now to learn how building your own wealth reservoir can give you the freedom to invest smarter—and live on your terms.

My guest today is Shyam Sankar, the CTO of Palantir Technologies. In this conversation, we explore the ideas that shape how Shyam thinks about technology, talent, and national power. We discuss the origins of Palantir's forward-deployed engineering model and the lessons he learned from Alex Karp about identifying people's "superpowers". We also talk about Shyam's fascination with the "heretics" of American history, the unconventional builders who challenged bureaucracy and created many of the systems that powered America's military and industrial success. Shyam argues that the United States must reindustrialize after decades of moving production overseas, and explains what we can learn from America's industrial past. In a new Colossus profile, our Editor in Chief Jeremy Stern tells the story of how Shyam became one of the most important but largely unseen figures behind Palantir, tracing his journey from immigrant roots to employee #13 and the architect of the company's success and distinctive culture. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.  ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp's⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠.  ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Rogo⁠ is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at ⁠Rogo.ai/invest⁠. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:02:43) Intro: Shyam Sankar (00:03:24) Defining Heretics in US Military History (00:05:01) The Story of Hyman Rickover (00:09:55) Formative Experiences & Worldview (00:14:50) Components of American Greatness (00:17:56) How to Unlock Talent (00:25:56) Palantir's Distinct Culture (00:28:15) Origin of Forward Deployed Engineering (00:34:24) What Does Palantir Actually Do? (00:36:19) Example: Airbus (00:40:20) State of the US Military Today (00:47:33) The U.S. Needs to Reindustrialize (00:52:19) Perspective of China (00:55:56) Our Key Asymmetric Advantages (01:00:57) Executive Orders for a Day (01:02:37) Negative Aspects of US Culture (01:04:47) Managing Rapid Pivots (01:09:17) Where Will AI Value Accrue? (01:12:37) Undeclared State of Emergency (01:15:45) Surprising Aspects of Palantir (01:17:50) To Do or To Be (01:18:50) Reflecting on Fatherhood (01:19:46) The Kindest Thing

Invest Like the Best: Read the notes at at podcastnotes.org. Don't forget to subscribe for free to our newsletter, the top 10 ideas of the week, every Monday --------- My guest today is John Arnold. John is probably the most famous energy trader of all time and certainly the most successful. One of the things John talks about is cultivating the best seat in your industry – the seat with the best perspective, the most information, the best systems..  John has been closely watching China's convergence in robotics, AI, and EVs, and shares his perspective from his recent trip to the country. We talk about the state of energy markets today – the misaligned goals and incentives, the NIMBYism that prevents building in America, and what he actually thinks about the wave of nuclear energy startups that everyone seems excited about.  John is also one of the most innovative philanthropists working today, applying that same analytical rigor to diagnosing structural failures across America — in healthcare, criminal justice, education, and beyond For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.  ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- Ramp's mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest.  ----- WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps (00:00:00) Welcome to Invest Like The Best (00:02:43) Episode Intro (00:03:43) Learnings from John's Trip to China (00:06:28) The EV Industry in China (00:08:43) How Subsidies Create Intense Competition (00:10:54) US-China Relationship (00:12:42) The Cost of Greatness (00:14:52) Creating the Best Seat in the Market (00:19:30) Baseball Card Arbitrage (00:23:03) Trading Natural Gas Futures (00:24:59) Energy Market Making Explained (00:27:11) Why Energy is Exciting Again (00:31:14) Meeting the Increased Demand for Energy (00:32:53) Why Policy is the Biggest Threat to Progress (00:36:28) Fixing Energy Infrastructure in the US (00:39:29) Advanced Nuclear Technology (00:42:05) The Prospects of Energy Startups (00:43:44) Input Costs in Solar & Batteries (00:47:54) Geothermal Energy: The Most Exciting Sector (00:50:57) Housing Reform in the US (00:53:39) The Role of Philanthropic Foundations (00:57:00) Reforming the Criminal Justice System (01:03:48) Social Outcomes Downstream of Education (01:07:20) Misaligned Incentives in the Healthcare System (01:12:08) Journalism as a Public Good (01:14:17) The Kindest Thing

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you avoiding your RRSP because you're afraid it could become a massive tax problem later?If you're a high-income earner or incorporated business owner, you've probably wondered whether stuffing money into your RRSP today just means paying 50% tax on it tomorrow. Maybe you've even held back contributions, thinking you'll “optimize it later” when you have the perfect plan. But in trying to avoid a future tax issue, you could be missing the bigger risk: not building enough in the first place. Wealth doesn't grow because you perfectly optimized every detail — it grows because you consistently created bigger “problems” worth solving.In this episode, you'll discover:Why an “RRSP that's too big” is usually a sign you're doing something right — and how to handle it strategically.How leverage strategies and smart withdrawals can turn a future tax concern into an opportunity to grow even more.How to think about asset location across RRSPs, corporate accounts, and non-registered investments to maximize flexibility and long-term tax efficiency.Press play now to learn how to use your RRSP as a powerful wealth-building tool — not something to fear.

Brazilian Treasury Bonds: 12% real yield

My guest today is John Arnold. John is probably the most famous energy trader of all time and certainly the most successful. One of the things John talks about is cultivating the best seat in your industry – the seat with the best perspective, the most information, the best systems..  John has been closely watching China's convergence in robotics, AI, and EVs, and shares his perspective from his recent trip to the country. We talk about the state of energy markets today – the misaligned goals and incentives, the NIMBYism that prevents building in America, and what he actually thinks about the wave of nuclear energy startups that everyone seems excited about.  John is also one of the most innovative philanthropists working today, applying that same analytical rigor to diagnosing structural failures across America — in healthcare, criminal justice, education, and beyond For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.  ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp's mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Vanta. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest.  ----- This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- This episode is brought to you by Rogo. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at Rogo.ai/invest. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps (00:00:00) Welcome to Invest Like The Best (00:02:43) Episode Intro (00:03:43) Learnings from John's Trip to China (00:06:28) The EV Industry in China (00:08:43) How Subsidies Create Intense Competition (00:10:54) US-China Relationship (00:12:42) The Cost of Greatness (00:14:52) Creating the Best Seat in the Market (00:19:30) Baseball Card Arbitrage (00:23:03) Trading Natural Gas Futures (00:24:59) Energy Market Making Explained (00:27:11) Why Energy is Exciting Again (00:31:14) Meeting the Increased Demand for Energy (00:32:53) Why Policy is the Biggest Threat to Progress (00:36:28) Fixing Energy Infrastructure in the US (00:39:29) Advanced Nuclear Technology (00:42:05) The Prospects of Energy Startups (00:43:44) Input Costs in Solar & Batteries (00:47:54) Geothermal Energy: The Most Exciting Sector (00:50:57) Housing Reform in the US (00:53:39) The Role of Philanthropic Foundations (00:57:00) Reforming the Criminal Justice System (01:03:48) Social Outcomes Downstream of Education (01:07:20) Misaligned Incentives in the Healthcare System (01:12:08) Journalism as a Public Good (01:14:17) The Kindest Thing

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you holding too much cash “just in case” — and missing bigger wealth-building opportunities because of it?Most Canadians start with a simple emergency fund. But as your net worth grows, your “wealth reservoir” gets more complex — and more powerful. The problem? Many people never redefine their number. They double-count safety, sit on excess liquidity, or stay overly conservative without realizing it. Meanwhile, others jump into advanced strategies before they've earned the right to. If you've ever wondered whether your cash buffer is too small, too big, or just inefficient, this conversation will challenge how you think about financial security and opportunity.In this episode, you'll learn:How to clearly define your personal “tier one” emergency number — and why it should evolve over time.When excess liquidity becomes “gravy” that can strategically supercharge wealth through smarter moves.How your asset mix (real estate, ETFs, leveraged investing, business ownership) changes the size and role of your reservoir.Press play now to rethink your wealth reservoir and discover whether you're protecting your future — or unintentionally holding it back.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereShould you actually retire with debt on purpose?For years, you've probably pictured retirement as completely debt-free — no mortgage, no payments, no financial pressure. But what if aggressively paying off your home is actually slowing down your path to financial freedom? If you're a high-income earner, business owner, or someone intentionally building wealth, the real question isn't “How fast can I kill this debt?” — it's “Is this debt strategically working for me?” Understanding the role of cash flow, inflation, taxes, and risk can completely change how you see retirement planning.In this episode, you'll discover:How inflation quietly makes long-term debt less expensive over time — and why that matters for your strategyWhen carrying debt into retirement can actually improve tax efficiency and preserve wealthThe key difference between emotionally uncomfortable debt and strategically powerful debt (and how to know which side you're on)If you want to rethink retirement planning and learn when debt can be a tool — not a threat — press play now.

Invest Like the Best: Read the notes at at podcastnotes.org. Don't forget to subscribe for free to our newsletter, the top 10 ideas of the week, every Monday --------- My guest today is Dan Sundheim. Dan is the founder and CIO of D1 Capital Partners. He thinks about markets and businesses constantly, and has built a career entirely around that obsession. He manages over $30B across both public and private markets, with investments in SpaceX, OpenAI and Anthropic, and a public portfolio of names you may never have heard of. Dan shares the story of the short case he wrote on Orthodontic Centers of America and posted on Value Investors Club, which crashed the stock, and helped him land his first job. He shares why he backed Anthropic at a moment when many people told him it was the Lyft to OpenAI's Uber, what reading Dario Amodei's essays reminded him of Jeff Bezos, and how he thinks about LLM business models through the lens of Netflix and Spotify. We spend time on the extraordinarily stressful moment in early 2021 when GameStop hit the firm, and what Dan believes is the single biggest tail risk facing the global economy right now. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.  ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp's⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠.  ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Rogo⁠ is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:02:43) Intro: Dan Sundheim (00:03:58) The State of Public & Private Investing (00:07:32) Investing in OpenAI and Anthropic (00:10:22) LLMs Business Model (00:14:13) How LLMs are like Netflix and Spotify (00:17:08) Focus v. Scope (00:22:43) The Bear Case for Hyperscalers (00:26:36) The Software Sell-Off (00:31:08) If Scaling Laws Stopped (00:32:18) Advice to a 12-Year-Old Investor (00:33:54) GameStop: D1's Darkest Hour (00:37:14) The Pivotal Dinner with LPs (00:40:56) Staying Calm and Confident (00:42:08) Economic Optimism vs. Societal Uncertainty (00:44:26) Investing on SpaceX and Rivian (00:48:09) Why Dan Loves Shorting (00:48:51) Sources of Inefficiency in Today's Markets (00:51:45) The Importance of Loyalty (00:53:11) Dan's Group Chat for Founders (00:55:39) What Motivates Dan (00:57:28) Posting on Value Investors Club (01:01:46) What Dan Learned at Viking (01:04:22) The Beauty of Art (01:06:49) Under-appreciated Parts of the Global Economy (01:08:00) The US-China-Taiwan Collision Course (01:12:10) Good Leaders vs. Good Businesses (01:13:15) The Kindest Thing

Alternative investments produce more cash flow with less volatility than public markets. This is why money invested in alternative assets have more than doubled over the last decade, from $7.2 trillion to $18 trillion, and expected to grow to $29 trillion by 2030.  Investments like Private Credit, niche commercial real estate, oil & gas, and specialized finance are exploding. Bob Fraser, Co-founder and CFO of Aspen funds, and USA Today bestselling author of Invest Like a Billionaire, has several specialized high performing funds with over 1000 retail investors in search of high-yielding, consistent cash flow with conservative risk profiles. 

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you accidentally letting hundreds of thousands of dollars sit idle in your holding company… unsure how to deploy it without triggering unnecessary tax?If you're a Canadian business owner with retained earnings building up in your holdco, you've probably felt the tension. You want to grow your wealth—but you don't want to make a costly mistake. Your accountant tracks what's happened, but who's helping you think proactively about what to do next? With salaries, RRSP room, rental properties, corporate investments, and tax efficiency all in play, it's easy to feel stuck between “do nothing” and “overcomplicate everything.” What you really want is clarity—and optionality.In this episode, you'll discover:A simple 50/50 framework for splitting retained earnings between risk-off liquidity and long-term growth.How to structure corporate investments to create tax-efficient capital gains and future tax-free income through the Capital Dividend Account.Why thinking holistically—across your corporation and personal assets—unlocks powerful flexibility, leverage, and long-term tax control.Press play now to learn how to turn your holding company into a strategic wealth engine—not just a parking lot for cash.

My guest today is Dan Sundheim. Dan is the founder and CIO of D1 Capital Partners. He thinks about markets and businesses constantly, and has built a career entirely around that obsession. He manages over $30B across both public and private markets, with investments in SpaceX, OpenAI and Anthropic, and a public portfolio of names you may never have heard of. Dan shares the story of the short case he wrote on Orthodontic Centers of America and posted on Value Investors Club, which crashed the stock, and helped him land his first job. He shares why he backed Anthropic at a moment when many people told him it was the Lyft to OpenAI's Uber, what reading Dario Amodei's essays reminded him of Jeff Bezos, and how he thinks about LLM business models through the lens of Netflix and Spotify. We spend time on the extraordinarily stressful moment in early 2021 when GameStop hit the firm, and what Dan believes is the single biggest tail risk facing the global economy right now. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.  ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp's⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠.  ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Rogo⁠ is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:02:43) Intro: Dan Sundheim (00:03:58) The State of Public & Private Investing (00:07:32) Investing in OpenAI and Anthropic (00:10:22) LLMs Business Model (00:14:13) How LLMs are like Netflix and Spotify (00:17:08) Focus v. Scope (00:22:43) The Bear Case for Hyperscalers (00:26:36) The Software Sell-Off (00:31:08) If Scaling Laws Stopped (00:32:18) Advice to a 12-Year-Old Investor (00:33:54) GameStop: D1's Darkest Hour (00:37:14) The Pivotal Dinner with LPs (00:40:56) Staying Calm and Confident (00:42:08) Economic Optimism vs. Societal Uncertainty (00:44:26) Investing on SpaceX and Rivian (00:48:09) Why Dan Loves Shorting (00:48:51) Sources of Inefficiency in Today's Markets (00:51:45) The Importance of Loyalty (00:53:11) Dan's Group Chat for Founders (00:55:39) What Motivates Dan (00:57:28) Posting on Value Investors Club (01:01:46) What Dan Learned at Viking (01:04:22) The Beauty of Art (01:06:49) Under-appreciated Parts of the Global Economy (01:08:00) The US-China-Taiwan Collision Course (01:12:10) Good Leaders vs. Good Businesses (01:13:15) The Kindest Thing

Travel headaches mount as a major storm slams the U.S. Northeast - plus investing cues from millennials and the latest on travel to and from Mexico amid cartel violence.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereIs index fund investing really the best path to financial freedom — or is it only effective if you can survive the emotional rollercoaster that comes with it?Most investors are told the same advice: buy the market, hold for decades, and trust long-term averages. And yes… mathematically, it works. But the real question is: can you stick with it when the market drops 20%? Or when you're retired and withdrawing income during a downturn?In this episode of Canadian Wealth Secrets, Kyle Pearce and Jon Orr break down a powerful question many Canadians overlook:Index Fund Investing: Growth Strategy or Income Strategy?They explore why index funds feel simple on paper, why real estate often feels “safer,” and how the best portfolio isn't just the one with the highest average return — it's the one you can actually stay committed to.This conversation dives into:The real reason many investors abandon index funds during market volatilityIndex fund vs real estate: why real estate feels more stable (even when it isn't)How an income investing strategy can reduce emotional decision-makingWhy leveraged investing in Canada looks great in spreadsheets but feels scary in real lifeWhat the 4 percent rule in Canada misses when markets decline during retirementHow to think about diversification, “dry powder,” and building a portfolio that supports long-term income needsIf you've ever wondered whether your RRSP, TFSA, or corporate investments are built for true financial freedom — or just built for average returns — this episode will shift the way you think about investing.

This is my second conversation with Josh Kushner, founder and managing partner of Thrive Capital. I recorded this conversation in October after publishing the Colossus cover story about him and Thrive. Given the overwhelming response, we created some breathing room before releasing it. Josh started Thrive in 2011. The firm now manages approximately $50 billion with a very small investment team. What makes Thrive different is how concentrated they are and how involved they get with their portfolio companies. We cover the iconic investments that defined Thrive: Instagram, Stripe, GitHub, and spend a lot of time on OpenAI. Josh explains how Thrive thinks about investing today and the three categories they're currently focused on. Josh also talks about building the firm, why they keep the team small, and what he's learned from A24 about enabling artists to do their best work. He shares personal stories that shaped him, including his grandmother's experience surviving the Holocaust, and lessons from Stan Druckenmiller, Jon Winkelried, and others at formative moments in Thrive's history. Please enjoy my great conversation with Josh Kushner. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.  ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp's⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠.  ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Rogo⁠ is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at ⁠Rogo.ai/invest⁠. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:02:43) Intro: Josh Kushner (00:03:46) How Thrive Has Changed Since 2023 (00:05:18) Thrive's Entrepreneurial Culture (00:12:22) The Power of Small Teams (00:13:35) Sponsors (00:14:35) Concentration as Differentiation (00:16:16) The Github Deal (00:18:08) Lesson from Stan Druckenmiller (00:20:37) Leading Stripe's $50 Billion Round (00:23:16) Instagram: Doubling an Investment in Days (00:25:43) Isomorphic: Thrive as an Enabling Technology (00:27:04) Thrive & A24 (00:28:19) OpenAI: The Product Josh Couldn't Unsee (00:32:09) Pricing the OpenAI Investment (00:33:40) OpenAI and Power (00:35:26) Finding Joy in Hard Work (00:39:15) Inside View of the Tech & AI Landscape (00:42:28) Three Investment Categories Thrive is Focused On (00:44:37) Thrive Holdings: Inside-Out Disruption (00:48:54) Competition in Venture (00:50:49) Sponsors (00:51:48) Thrive's Immutable Values (00:54:21) A Family Story of Survival (00:56:43) The American Dream (00:58:03) What Artists Can Teach Investors (01:00:26) Never Compromise Your Values (01:01:33) The Story Behind Josh's Forever Watch

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you accidentally letting “dead equity” sit idle when it could be working harder for you?Most Canadians think financial freedom optimization is about cutting expenses or chasing the next hot investment. But what if the real opportunity is hiding in plain sight — in your car, your mortgage, or any asset quietly losing value? In this episode, we unpack a simple car lease scenario that reveals a much bigger question: Are you thinking strategically about debt, equity, and optionality — or just following the default path?If you've ever wondered whether to pay cash, finance, lease, invest, or “just play it safe,” this conversation will challenge how you evaluate those decisions.In this episode, you'll discover:How to spot “alpha” opportunities — small arbitrage moves that compound into meaningful advantagesThe difference between depreciating vs. appreciating assets — and how to reposition equity more strategicallyWhy optionality might be one of the most overlooked principles in building long-term financial flexibilityPress play now to start seeing everyday financial decisions through a sharper, more strategic lens.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to KylIn this episode of Canadian Wealth Secrets, a simple vehicle scenario becomes a powerful lesson in alpha, arbitrage, and optionality — revealing how smart CanReady to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Seth Bradley interviews Ben Fraser, Managing Director and Chief Investment Officer at Aspen Funds, on how Aspen built a scalable fund-to-funds platform to support more than 40 independent capital aggregators in 2025 alone. Ben breaks down Aspen's macro-driven investment philosophy, how the firm evolved from distressed mortgage notes after the Great Financial Crisis into a multi-asset platform, and why focusing on tailwinds matters more than sticking to a single asset class. The conversation dives deep into the structural shift from co-GP capital raising to compliant fund-of-funds models, the importance of simplifying backend infrastructure for promoters, and why recurring cash-flowing products can unlock true scalability for capital raisers. Ben also shares where he sees the independent capital aggregator model heading as private market demand accelerates. Guest InfoBen FraserCurrent role: Managing Director & Chief Investment Officer, Aspen FundsBased in: United StatesSay hi to them at: https://aspenfunds.us | Invest Like a Billionaire Book your free demo today at bill.com/bestever and get a $100 Amazon gift card. Visit ⁠www.tribevestisc.com⁠ for more info. Try QUO for free PLUS get 20% off your first 6 months when you go to quo.com/BESTEVER  Join the Best Ever Community  The Best Ever Community is live and growing - and we want serious commercial real estate investors like you inside. It's free to join, but you must apply and meet the criteria.  Connect with top operators, LPs, GPs, and more, get real insights, and be part of a curated network built to help you grow. Apply now at⁠ ⁠⁠⁠www.bestevercommunity.com⁠⁠ Podcast production done by⁠ ⁠Outlier Audio⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Our guest on the podcast today is Jim O'Shaughnessy. Jim founded O'Shaughnessy Asset Management, a quantitative investment management firm in 1993. Franklin Templeton acquired the firm in 2021. Jim is also an author of several books, including Invest Like the Best and What Works on Wall Street. His latest book, Two Thoughts: A Timeless Collection of Infinite Wisdom, is a compilation of quotations from famous artists, writers and thinkers. Jim also hosts his own podcast called Infinite Loops. In addition, Jim is the founder and CEO of O'Shaughnessy Ventures, which provides financial backing and other support to individuals and projects.Episode Highlights00:00:00 Building a New Way to Analyze the Stock Market00:07:18 How Stock Brokers Sold Stories Before Quants00:12:19 Stock Price vs. Narrative and How Quants Avoid Stock Investing Pitfalls00:20:05 Long-Term Investing, Bonds, and Keeping Emotions Out of Your Portfolio00:29:50 Pre-Seed Investments, Finding the Right Founders, and Valuations Today00:40:08 The Making of Two Thoughts: A Timeless Collection of Infinite Wisdom00:47:29 Voices on the Infinite Loops Podcast00:53:12 “Statis is Death” and Lifelong LearningMore From The Long ViewNick Maggiulli: Climbing the Wealth LadderLawrence Lam: ‘The Types of Companies That Attract Me Are Founder-Led and Profitable'More From MorningstarHow to Determine What a Stock Is WorthHow to Build a Portfolio to Reach Your Financial Goals5 Ways Emotions Sabotage Your Investment SuccessFOMO Can Lead to Lower Returns. Don't Fall For ItIf you have a comment or a guest idea, please email us at TheLongView@Morningstar.com.Follow Christine Benz (@christine_benz) and Ben Johnson (@MstarBenJohnson) on X, and Christine Benz, Amy Arnott, and Ben Johnson on LinkedIn. Visit Morningstar.com for new research and insights from Christine, Ben, and Amy. Subscribe to Christine's weekly newsletter, Improving Your Finances.If you want more Morningstar podcasts, check out The Morning Filter and Investing Insights. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereWhat if carrying debt into retirement could actually reduce your taxes and increase your long-term flexibility?Many Canadians are taught that being mortgage-free is the ultimate financial goal—but what happens when that mindset clashes with taxes, retirement withdrawals, and lost growth opportunities? If the Smith Maneuver or leverage-based investing has ever made you uneasy, especially when you picture retirement looming, you're not alone. This episode breaks down why “good debt” doesn't suddenly stop working when your house is paid off—and how intentional use of leverage can turn future tax problems into strategic advantages.In this episode, you'll discover:How investment debt can offset RRSP/RRIF withdrawals and potentially eliminate taxes in retirementWhy starting the Smith Maneuver earlier creates more optionality and smoother income later onHow combining RRSPs, non-registered investments, and leverage can increase net worth while reducing long-term tax dragPress play now to learn how strategic debt, done right, can give you more control, lower taxes, and greater financial freedom over your lifetime.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to KylReady to connect? Text us your comment including your phone number for a response!Ready to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you sitting on rental or business cash flow that could be quietly accelerating your mortgage payoff and cutting your tax bill at the same time?If you're a Canadian business owner, sole proprietor, or personally hold rental properties, chances are cash flows into your account each month—and then slowly leaks out to cover expenses. In this episode, Kyle and Jon unpack how that “idle” money can be put to work instead of collecting dust, using a strategy that builds on the Smith Manoeuvre without requiring you to go all-in or take on more risk than you can handle. They walk through real-world scenarios, common misconceptions, and the practical constraints that determine whether this strategy fits your situation.By listening, you'll learn how to:Turn non-deductible mortgage interest into deductible business or investment interest using cash damming—without increasing your overall debt.Improve cash-flow efficiency by recycling the same dollars to pay down your mortgage faster while still funding business or rental expenses.Apply the strategy conservatively or aggressively based on interest rates, mortgage rules, and your personal comfort level—so you stay in control.Press play now to see how cash damming could quietly boost your net worth and tax efficiency using money you already have.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to KylReady to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

My guests today are Alex Behring and Daniel Schwartz, Co-Managing Partners of 3G Capital. 3G has built one of the most distinctive firms in investing around a simple idea: there are only a handful of truly great businesses and even fewer great CEOs. Their model is to raise capital with the intention of making just one investment per fund, commit meaningful amounts of their own money alongside their partners, and focus all of their time and best people on that single opportunity.  Their approach has produced a series of iconic deals, including Burger King, Tim Hortons, Hunter Douglas, and Skechers. They have also become known for developing talent early, giving young leaders real responsibility and ownership, and holding an unusually high bar. Once you've heard from Alex and Daniel, I highly recommend you read our in-depth profile on them and 3G Capital. They gave our managing editor Dom Cooke unprecedented access and the outcome is an excellent profile about the fifty year history of 3G and how the model began with Jorge Paulo Lemann in Brazil. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.  ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠Ramp's⁠ mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠.  ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Rogo⁠ is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at ⁠Rogo.ai/invest⁠. ----- ⁠Ridgeline⁠ has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps (00:00:00) Welcome to Invest Like the Best (00:02:43) Episode Intro: Daniel Schwartz & Alex Behring (00:04:03) The “One Investment Per Fund” Model (00:08:22) Great Businesses Own the Relationship With Their Customers (00:11:23) The Unique Structure of 3G Capital (00:13:36) How a Transaction Takes Shape (00:17:04) Why Hunter Douglas Was Appealing (00:21:34) The Advantages of Staying Small (00:23:58) Alex's Railroad Story (00:26:36) Ownership is Key (00:30:26) Centralize the What, Decentralize the How (00:31:55) The “Burger King is Run by Children” Story (00:34:21) Negotiating with Tim Hortons (00:40:39) Never Compromise on Quality (00:42:01) Talent Over Tenure (00:50:26) 3G's Operating System (00:57:14) When a Brand is Bigger than the Business (01:00:17) Why Burger King Was Undervalued (01:03:15) The Beauty of the Franchise Model (01:06:24) Kraft Heinz: A Case Study in Concentration Risk (01:09:07) Skechers: Great Product Meets Great Distribution (01:16:07) Finding Forever Businesses (01:17:52) Zero-Based Budgeting & When It Works (01:21:10) The Current State of Capital Markets (01:25:23) Misconceptions About 3G (01:32:01) The Power of Patience (01:33:39) The Kindest Thing

What does it really mean to invest like a billionaire? Kathy Fettke sits down with Bob Fraser, author of Invest Like a Billionaire, to explain how ultra-wealthy investors build long-term wealth — and why public markets often fail everyday investors. After losing everything twice in the public markets, Bob breaks down why billionaires focus on private markets, including real estate, private credit, and alternative investments that offer lower volatility and stronger returns. You'll learn why diversification strategies can fail, how private investments reduce risk, and what today's market conditions mean for multifamily and commercial real estate investors.

Wealth that ends with you is success, but wealth that outlives you is a legacy.In this episode, Corwyn J. Melette sits down with Mark Miller, CEO of Hilton Tax and Wealth Advisors, to provide the tactical manual for dynasty building. Mark is a returning guest where he previously talked about the foundational concepts of wealth preservation and the mindset required to stop the "start-over" cycle. While that first conversation was a primer on financial literacy, this episode dives into the "what's next": creating the enduring trust systems and "wholesale" investing strategies used by the Hilton family.Mark bridges the gap between simply having money and systematizing it. If the first episode taught you how to start the car, this episode teaches you how to build a self-driving vehicle that ensures your great-grandchildren never have to start from zero again.The Legacy Moment:True legacy isn't about leaving a lump sum of cash; it's about building a disciplined system and imparting the financial wisdom that ensures your family never has to start from zero again.Key Takeaways0:00 - Legacy vs. Success: Defining wealth that outlasts you.5:38 - Why the third generation often loses everything and how to stop it.7:23 - The "Sieve" Strategy: Using trust structures to prevent "lump sum" wealth destruction.11:35 - Parenting & Money: How to teach heirs the value of a dollar before they inherit.15:21 - Retail vs. Wholesale: The hidden 3-4% fees eating your investments.17:40 - The "Bucket" Concept: Following Warren Buffett's lead in asset diversification.24:18 - Safety First: Why the ultra-wealthy prioritize downside protection over high-risk gains.Catch Up on the Foundation:Missed Mark's first appearance? Before you dive into the systems, make sure you have the right mindset.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereHave you ever felt pressured into a “sophisticated” financial strategy you didn't actually understand?As a Canadian incorporated business owner or high-net-worth professional, you're used to handling complexity — but financial decisions feel different when the stakes are personal and the explanations fall short. Too often, strategies like estate freezes, corporate insurance, or private investments are presented with urgency instead of clarity, leaving you overwhelmed, hesitant, or quietly unsure if you're making the right move. This episode challenges the idea that pressure equals progress and reframes what real sophistication in wealth planning actually looks like.In this episode, you'll discover:Why poor financial outcomes usually come from lack of understanding, not bad strategiesHow to spot pressure from financial advisors disguised as “best practices” or “what wealthy people do”What confident, flexible wealth planning looks like when every tool has clear purpose and contextPress play to learn how clarity — not urgency — becomes the foundation of a wealth plan you can trust and stand behind.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyleif you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…leReady to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereIs the 4% rule still a reliable path to financial freedom in Canada—or is it holding your retirement plan back?You've heard it a hundred times: save 25x your annual expenses and withdraw 4% per year in retirement. But in 2026 and beyond, does that formula still stack up? Whether you're 10 years out from retirement or already hitting your financial freedom number, rigidly following outdated rules could put your lifestyle—and peace of mind—at risk. This episode dives into how the 4% rule was built, why it may not fit today's market realities, and how to think more flexibly about spending, investing, and enjoying your money without watching your net worth dwindle.In this episode, you'll discover:Why the original 4% rule was designed for failure avoidance, not lifestyle optimizationHow a flexible approach to withdrawals can empower smarter spending decisions year by yearThe mindset shift that can help you grow your net worth even in retirementPress play now to rethink your retirement strategy and build a wealth plan that works for your real life—not just the spreadsheets.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyleif you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a laReady to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Market volatility doesn't just test portfolios. It exposes how founders think under pressure. In this episode of Founder Talk, Alex Sheridan sits down with Matt Rice and Bill Seyfarth of Vistamark Investments, two experienced investment professionals who have built and scaled an advisory firm by staying disciplined when markets — and emotions — swing hard.Together, they tackle a common but dangerous founder mistake: treating investing like a reaction instead of a system. Matt and Bill explain why panic selling, market timing, and overconfidence quietly destroy long-term outcomes — especially for entrepreneurs used to controlling every variable in their business. The conversation offers a calmer, more strategic lens for thinking about wealth, retirement, and capital allocation alongside building and running a company.Rather than quick takes or hype, the episode delves into mindset shifts. Founders will come away with clearer thinking around volatility, a better framework for separating business risk from personal wealth, and practical lessons drawn from real market cycles, not headlines.Q&A-Style Takeaways with Timestamps00:00:00 – Introduction00:03:40Q: What helped Vistamark grow from zero to hundreds of millions in assets so quickly?A: Years of credibility, deep relationships, and trust built long before launching the firm — not overnight tactics.00:08:42Q: Why do many founders delay retirement and investment planning?A: They over-invest in their business and underestimate how hard it is to catch up later without time and compounding.00:11:50Q: Why is “time in the market” more important than timing the market?A: Missing just a few strong market days can dramatically reduce long-term returns, especially during volatile periods.00:15:14Q: Is retirement overrated for founders who love what they do?A: Retirement doesn't have to mean stopping work — it can mean optionality, flexibility, and control over time.00:22:20Q: What should founders consider before selling their company?A: Whether they're selling for the right reasons — and whether they have a clear plan for life after the exit.00:33:15Q: Why do investors often make the worst decisions during market crashes?A: Human psychology is wired for fear and greed, which leads to selling low and abandoning disciplined strategies.00:58:48Q: Does more money actually make founders happier?A: The absence of money creates stress, but beyond a certain point, fulfillment comes from purpose, balance, and impact.Watch the full conversation to hear how experienced investors think when markets get emotional — and why discipline matters more than predictions. Subscribe to Founder Talk for more authentic, no-fluff founder interviews.

My guest today is Ben Horowitz, the co-founder of Andreessen Horowitz. Since its founding in 2009, a16z has grown into one of the most influential firms in venture capital, reshaping how technology companies are funded and how power and ideas move through Silicon Valley and around the world. This conversation focuses on sides of Ben's story you don't often hear. Ben reflects on the people who shaped him, including Nas, Andy Grove, and his father, and shares why he chose to personally fund new technology for the Las Vegas Police Department. We also talk about how he thinks about a16z's responsibility in shaping the trajectory of America, the scale of his ambition for the firm, and what he sees as the biggest risk facing the country. Please enjoy this great and unique conversation with Ben Horowitz. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.  ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp's mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Vanta. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest.  ----- This episode is brought to you by Rogo. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at Rogo.ai/invest. ----- This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps (00:00:00) Welcome to Invest Like the Best (00:02:43) Episode Intro: Ben Horowitz (00:03:27) The State of America Right Now (00:06:06) How Policy Could Destroy America (00:08:29) AI Changes the Laws of Company Building and Investing (00:11:40) Why AI Researchers are Paid $100M (00:13:16) Thoughts on Growing Inequality (00:18:07) Societal Challenges Due to AI (00:19:56) Ben's Scope of Ambition for the Next 20 Years (00:22:48) Andy Grove's Influence on Ben (00:27:44) Starting Andreessen Horowitz (00:32:53) Early Mistakes (00:36:17) What Capital Markets Are Missing (00:37:44) Why VC and Not PE (00:40:03) Tradeoffs with Scale (00:41:10) A Culture is Not a Set of Ideas, it's a Set of Actions (00:43:05) Lessons from His Father (00:45:03) Exciting Use Cases of AI (00:46:46) Ben's Friendship with Nas (00:50:05) Funding New Technology for the Las Vegas Police Department (00:54:07) The Kindest Thing

In this episode of the Real Estate Pros Podcast, host Micah Johnson interviews Alex Blackwood, CEO and co-founder of Mogul Club, a revolutionary platform that democratizes real estate investing. Alex shares insights into the user experience, investment process, and the unique value proposition of Mogul Club, which allows individuals to invest in real estate with minimal capital and without the traditional headaches associated with property management. The conversation also explores current market trends, the accessibility of real estate investments, and the future growth potential of Mogul Club.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true 'white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a "mini-mastermind" with Mike and his private clients on an upcoming "Retreat", either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas "Big H Ranch"? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

Mike Zlotnik breaks down real estate market cycles, why predictability matters more than hype, and how chess-level thinking applies to investing.In this episode of RealDealChat, Mike Zlotnik returns for a deep, no-nonsense conversation on market cycles, risk, and building a resilient real estate portfolio.Mike shares his journey from political refugee and chess master to tech executive and full-time real estate fund manager. We explore how chess shaped his approach to investing, why past performance is not predictive, and how investors should adapt strategies based on where we are in the market cycle.We dive into why Mike is currently focused on industrial and open-air retail, what he calls the 2% positive spread rule (cap rate vs interest rate), and why downside protection, fixed-rate debt, and tenant credit quality matter more than chasing appreciation. Mike also explains why multifamily still has unresolved risk, how AI could be deflationary, and why diversification—across assets and time—is the most underrated strategy in investing.This episode is a masterclass in patience, discipline, and thinking several moves ahead.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereWhat should you do when your corporation has more cash than clarity?Many incorporated business owners hit a silent milestone: revenue is steady, personal income is solid, but inside the corporation, retained earnings quietly pile up—doing nothing. Inflation erodes their value. Investment options seem risky, tax-heavy, or too complex. The real challenge isn't just finding a strategy—it's knowing what role that idle money should play. In this episode, Tyson, a physiotherapy clinic owner, shares his journey from uncertainty to empowerment as he reframes his financial approach and builds a stable foundation for growth.You'll discover:Why retained earnings can become a hidden liability if left unstructuredThe mindset shift from chasing returns to preserving optionalityHow corporate-owned whole life insurance can offer growth, access, and protection—without rushing into risky decisionsIf your retained earnings feel stuck or exposed, press play now to hear how stability and strategy can unlock new possibilities.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle…taking a salary with a goal of stuffing RRSPs;…inveReady to connect? Text us your comment including your phone number for a response!ManyReady to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

My guest today is ⁠Gokul Rajaram⁠, Founding Partner at Marathon Management. Gokul is one of the most prolific product builders and investors of the last twenty years. He has built the core ad and product businesses at Google, Facebook, Square, and DoorDash, working at each company during its most formative scaling periods. Alongside his operating career, Gokul has invested in more than 700 companies, giving him an unusually broad view into how products are built and scaled. This conversation is about how product building is changing with AI. We discuss the one thing Gokul believes is truly future-proof in AI, why companies like Zendesk and Slack are more exposed than Salesforce or NetSuite, and the only sources of defensibility.  We also talk about everything Gokul has learned from helping build the most important ads businesses, including the only three ways an ad business can make money, how those constraints shape product decisions, and what consumer behavior change threatens every major platform. Gokul shares lessons from working closely with Larry and Sergey, Mark Zuckerberg, Jack Dorsey, and Tony Xu. Please enjoy my conversation with Gokul Rajaram. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠.  ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp's mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠⁠ to sign up for free and get a $250 welcome bonus. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠Vanta⁠. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠.  ----- This episode is brought to you by ⁠Rogo⁠. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at ⁠Rogo.ai/invest⁠. ----- This episode is brought to you by⁠ ⁠WorkOS⁠⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠ ⁠WorkOS.com⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps (00:00:00) Welcome to Invest Like The Best (00:00:53) Meet Gokul Rajaram (00:02:05) How Product Development is Changing with AI (00:07:32) Philosophy of Product Management (00:10:19) What is Future-Proof in AI Era (00:11:25) Building AI Applications Today (00:15:03) Systems of Record vs Agent Companies (00:16:58) Which Legacy Software Companies Are Most Exposed (00:22:15) Stickiness in the AI Era (00:24:10) Learning from Larry Page and Sergey Brin (00:28:15) Learning from Mark Zuckerberg (00:31:31) Learning from Jack Dorsey (00:35:40) The Art of Great Product Design (00:36:49) Weekly CEO Communication (00:40:27) Three Ways to Succeed in Advertising (00:44:27) What Should Scare Major Ad Platforms (00:48:24) North Star Metrics (00:50:09) Self-Serve Products (00:54:50) Careers in the AI Era (00:59:03) Stay Long Enough to Have Impact (01:00:10) Founder Authenticity and Superpowers (01:02:21) Navigating the Idea Maze (01:03:42) Role of Boards (01:06:31) Excellence in Customer Acquisition  (01:09:11) The Kindest Thing 

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre dividends really more tax-efficient for business owners—or is that advice costing you hundreds of thousands over time?If you're an incorporated Canadian business owner, you've likely heard the age-old advice: “Just take dividends—it's simpler and saves tax.” But what if that oversimplified strategy is quietly undermining your long-term wealth? In this episode, Jon and Kyle unpack the real math behind salary vs. dividends, revealing how your compensation choices ripple through CPP contributions, RRSP room, investment opportunities, and future flexibility. Whether your business is just starting out or generating strong retained earnings, understanding these trade-offs is crucial to building sustainable wealth.By the end of this episode, you'll discover:Why dividends don't always save tax—and when they can actually hurt your long-term growthHow to use salary strategically to open up RRSP room and diversify beyond your businessA clear, math-based breakdown of which approach works best at different income and retained earnings levelsPress play now to finally take the guesswork out of how you pay yourself—and make smarter, wealth-building decisions as an incorporated business owner.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle…taking a salary with a goal of stuffing RRSPs;…inveReady to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Robert Netzly joins Steve today on the podcast to discuss investing in a different light, the Light of the Bible. Should we as Christians be more careful with our investments, and if so, how? Here is the free tool that Robert spoke about towards the end of the video for seeing if what you're invested in is God-honoring: https://inspireinsight.com/about You can learn more about his book here: (Canonpress) https://tinyurl.com/4cwnrzeh We hope that Grounded has been a help to your walk with our Lord. in Christ, the Grounded Team

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you relying on “just growing the pile” to fund your retirement?Too many Canadian business owners hope their savings will be “enough” without ever truly running the numbers—or questioning the assumptions behind their plan. In this episode, Jon Orr and Kyle Pearce break down a real case study of a listener preparing to retire at 55. They uncover the common blind spots around equity-heavy portfolios, the behavioral traps that derail even the smartest strategies, and why knowing your number isn't the same as building a system that gets you there. Whether you're 5 or 15 years out from retirement, this deep dive is full of insights to tighten your approach.You'll discover:Why a clear monthly cash flow target is more useful than a vague retirement “pile.”The risks of a 100% equity portfolio during the decumulation phase—and how to mitigate them.How to align your investment strategy with your behavior, so your plan doesn't fall apart when the market does.Press play now to find out where this listener nailed their strategy—and where small shifts could mean a more confident, flexible retirement.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle…taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large suReady to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereIs your financial freedom being hijacked by your emotions?We all like to think we're logical with money—crunching the numbers, weighing the odds, making the “smart” move. But the truth? Most of our financial behavior is driven by emotion, not math. In this episode, Jon Orr and Kyle Pearce unpack the hidden psychological tug-of-war that shapes our habits, investment choices, and long-term wealth strategies. Inspired by Freakonomics Radio and grounded in behavioral finance, they explore why knowing what to do isn't the same as doing it—and what actually makes the difference.You'll discover:A practical framework (elephant vs. rider) for understanding and overcoming self-sabotaging money habits.How to bridge the gap between financial theory and real-life action—even when fear or doubt creeps in.Smart ways to align your investments and financial systems with behavior you can actually sustain.If you've ever struggled to follow through on the “right” financial move to gain financial freedom, press play now—this episode could change how you think (and act) with money.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle…taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earReady to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

This week is a special episode. Only David Senra could get me to be on the other side of the mic. Because I don't plan on being interviewed often, I wanted to share this conversation, which I so enjoyed, with our audience. It went in a very different direction than I expected. We barely talk about investing or interviewing. Instead, we talk about finding an organizing principle for life, undiscovered talent, and the idea that “the reward for good work is more work.” We also discuss the principles that guide how I think about building Invest Like the Best, Colossus, and Positive Sum. This conversation was originally recorded and released on David Senra, and I wanted to share on the Invest Like The Best feed as well. Please go follow what he's doing, there's no one like David. Enjoy! For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp's mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Vanta. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest.  ----- This episode is brought to you by Rogo. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at Rogo.ai/invest. ----- This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps (00:00:00) Welcome to Invest Like The Best (00:04:26) Intro (00:05:14) The Joy of Championing Undiscovered Talent (00:07:33) How One Tweet Changed David's Life (00:10:16) The Upanishads Passage That Shaped Patrick's Worldview (00:15:32) Growth Without Goals  (00:17:24) Why Media and Investing Are the Same Thing (00:33:05) The Search for True Understanding (00:35:36) The Daniel Ek Dinner That Launched David's Podcast (00:39:02) Making Your Own Recipe From the Ingredients of Great Lives (00:43:46) The Privilege of a Lifetime Is Being Who You Are (00:52:06) Bruce Springsteen (00:57:23) Clean Fuel vs Dirty Fuel: The Source of Your Ambition (01:01:43) The Unfair Advantage of Podcasting (01:04:12) Relationships Run the World (01:11:10) The Origin Story of Invest Like the Best (01:12:45) Building Colossus: Why Start a Magazine in 2025 (01:18:42) People Are More Interested in People Than Anything Else (01:22:12) Hiring Through Output (01:26:23) Learn, Build, Share, Repeat (01:30:01) The Daisy Chain: How Reading Books Led to Everything (01:33:15) Red on the Color Wheel: Sam Hinkie's Observation (01:40:17) Finding Your Superpower and Becoming More Yourself (01:45:06) Repetition Doesn't Spoil the Prayer: Teaching as Leadership (01:48:11) Life's Work: A Lifelong Quest to Build Something for Others (01:52:00) The Ten Roles Game and What Matters Most (01:59:12) Husband, Father, Grandfather (02:01:52) The Kindest Thing

Okay. This show today is part of our Relentless Health Value "The Inches Are All Around Us" series. This Inches Talk is a metaphor for finding all those little places where there is healthcare waste as a first step in an effort to excise all these little pockets of waste. For a full transcript of this episode, click here. If you enjoy this podcast, be sure to subscribe to the free weekly newsletter to be a member of the Relentless Tribe. Shane Cerone said this phrase during episode 492, and I loved it because there are inches all around us for sure. And the thing with all these inches that we're gonna talk about today and last week and next week and the week after that, yeah, these are inches that actually you could cut them. And there are millions and billions of dollars, and you actually improve patient care. You improve clinical team experience. Also, you're cutting out friction and making it easier to do the right thing to care for patients. These are no-brainer kinds of stuff if your North Star is better and more affordable patient care, but they are also somebody else's bread and butter in a "one person's cost is another person's revenue" kind of way. So, yeah … what makes perfect common sense might not be as easy as it might look on paper, as we all know so well. So, last week we dug into all of the inches of expensive friction that develop when stakeholders interact—like, a clinical organization and a payer and a plan sponsor, self-insured employer. They try to get paid or pay. They try to direct contract because what will be found fast enough is that the data is not the data is not the data, as Mark Newman talked about last week (EP496); and a dollar is not a dollar is not a dollar. Again, you'll find this out fast enough. All of you know when you talk to entities up and down the patient journey or across the life of a claim, otherwise known as a healthcare transaction. It's mayhem to get a claim paid often enough. Each stakeholder comes in with their own priorities and views and accounting methods and various rollups. I like how Stephanie Hartline put it. She wrote, "Healthcare … moves through many hands without a rail that preserves truth along the way. Attribution breaks, and truth gets reassembled later. The difference isn't capability—it's infrastructure. Line-item billing ≠ line-item settlement." Or I also like how Chris Erwin put it. He wrote, "When the blueprint isn't standardized, you aren't scaling. You're just compounding chaos." And yeah, then all of a sudden when there's no through line, there's no rail that connects all the data to the data to the data, or all the dollars to the dollars to the dollars. Suddenly 30% of any given healthcare transaction goes to trying to straighten it all back out again—to reassemble it, as Stephanie said. It's like unleashing 100 chaos monkeys and then having to pay to recapture them all. Listen to the show with David Scheinker, PhD (EP363) from last year about "Hey, how about we all just use the same template and avoid a lot of this." Or read Zeke Emanuel's book about how the USA should potentially consider copying the Netherlands model because they have private insurance. But they cut admin costs 75% or something like that. Oh, right … through standardization. Jesse Hendon summarized this the other day. He wrote, "Providers don't need armies of coders to fight 50 different insurance rule books [when you have some standardization here]." I say all this to say after recording the episode with Mark Newman from last week, I have become intently fascinated by what goes on in this non-standardized or otherwise friction points between stakeholders. There are a lot of inches in this gray area land of confusion.   This show today digs into one of them, which is what does it take to process a claim? Just technically. What are the pipes involved to submit a claim and, again, get paid for it, which is a healthcare transaction—just simply the technology moving the data around—even if everything in the pipes is a non-standardized hot mess. Because just fixing up the processing and the pipes here—again, while this doesn't solve the entire data isn't a data isn't a data or a dollar isn't a dollar isn't a dollar problem—if we can just cut out some of the processing and the moving the data around costs, just this all by itself is $6 billion a year worth of inches. Plus, as an added bonus, fix up the pipes for better data flow and now patient care can be faster if, for example, the prior auth or etc. processes transpire faster. And clearinghouses have entered the chat. But you know, when clearinghouses come up, at least in my world, when the clearinghouse word gets dropped, it's usually accompanied by like a puff of smoke because no one is quite sure what those guys do all day. So, we all sort of look at each other in the conversation and move on. Lucky for me and possibly you if I've managed to suck you into my web of intrigue, I ran into Zack Kanter from Stedi, a new clearinghouse, who agreed to come on the pod here and aid my exploration into this demarcation zone between stakeholders. So, let's start here. What is a clearinghouse? Well, a clearinghouse is the same thing as a switch when we're talking about pharmacy data transfers, if you're familiar with that terminology and that's helpful. But either way, in the conversation with Zack Kanter that follows, Zack will explain this better; but clearinghouses are like a hub, maybe, that connects all the payers with all the providers. So, if you want an eligibility check or you wanna submit a claim or do a prior auth of the payer, whatever you're trying to do, get paid, you as an EHR system or a doctor's office or an RCM (revenue cycle management) company, you don't have to set up your own personal data connection with every single payer out there. You don't have to go through all the authentications and the BAAs (Business Associate Agreements) and map all the fields and set up the 100 SOC 2–compliant APIs (application programming interfaces). Instead, you can hook up to one clearinghouse, and then that clearinghouse connects with everybody else. So, most medical claims transactions have a clearinghouse in the middle, like an old-timey telephone operator routing your claim or denial or approval of that claim or eligibility check or whatever to the right place. And unfortunately, old-timey telephone operator is a pretty apt metaphor, depending on which clearinghouse you're using. Anyway, Zack Kanter told me that the price to just send and receive an electronic little piece of data in healthcare through a clearinghouse costs about 1,000 times more than any other industry would pay. Like, if you do an eligibility check, that's gonna cost 10 to 15 cents per. The trucking industry pays that much for 1,000 such data transfers. They would riot if someone asked them to spend a dollar for 10 data transfers. That'd be ridiculous in their eyes. But in healthcare, all these dimes add up to, again, $6 billion a year—them's some inches there—which also equal delays in payment and patient care. Now you might be thinking, "Oh, well, maybe it costs this much because healthcare is so much more complicated than trucking or whatever." Well, turns out the opposite is true: Because of HIPAA, ironically enough, healthcare is, in fact, much more standardized (we were talking about standardization before); but healthcare is actually much more standardized than many other industries due to HIPAA's administrative simplification rules, which mandate a universal language for transactions—the pipes I'm talking about now. So, actually, for as much as I was just kvetching about chaos monkeys, compared to other industries, the baseline construct here is actually much more orderly than, for example, the trucking industry or whatever, like Amazon or Walmart has to deal with with their millions of vendors. Now—and here's a really big point, especially for self-insured employers—you know who the main customer is for a lot of the more programmatic, the newer kinds of clearinghouses? I'll tell you: newer digital entities who do RCM (revenue cycle management) for provider organizations, and that can be great if you're a practice just trying to keep up with payer denials and expedite patient care. But look, all you plan sponsors and self-assured employers and maybe unions out there, the more RCM purveyors start working with programmatic clearinghouses, the more you not doing programmatic prepayment integrity programs with unconflicted third-party prepayment integrity vendors who are as hooked into the data streams and the clearinghouses as the RCM vendors are, the more, as I said last week, increasingly you're bringing an ever more rusty knife to a gunfight. So, that is certainly something to consider. There's a whole episode next week about this with Mark Noel from ClaimInsight. Or if you just can't wait, go back and listen to the show with Kimberly Carleson (EP480) just for the gist of it, or the one with Dawn Cornelis (EP285) from a few years ago. They're talking post-payment integrity programs, but a lot of the same rules apply. The show today is sponsored by Aventria Health Group, as usual. But I do want to say that we got some very appreciated financial support from Stedi, the only programmable healthcare clearinghouse. And here is my conversation about all of the inches that are all around us, specifically in the healthcare data pipes, with Zack Kanter, who is the CEO and founder over at Stedi. Also mentioned in this episode are Stedi; Shane Cerone; Mark Newman; Stephanie Hartline; Chris Erwin; David Scheinker, PhD; Zeke Emanuel, MD, PhD; Jesse Hendon; Mark Noel; ClaimInsight; Kimberly Carleson; Dawn Cornelis; Aventria Health Group; Preston Alexander; Eric Bricker, MD; and Kada Health. For a list of healthcare industry acronyms and terms that may be unfamiliar to you, click here. You can learn more at stedi.com. You can also follow Zack and Stedi on LinkedIn.   Zack Kanter is the founder and CEO of Stedi, the only programmable healthcare clearinghouse. Stedi has raised $92 million from Stripe, Addition, First Round, USV, Bloomberg Beta, and other top investors. He has previously appeared on podcasts, including In Depth by First Round Capital, Invest Like the Best, Village Global, and Rule Breaker Investing.   09:47 What things are being paid for that we might not be aware we're paying for in healthcare? 12:09 Why HIPAA actually makes healthcare more standardized than other industries. 15:35 How healthcare is ahead in some ways and behind in others. 18:03 Where do the 4 to 5 days come from in healthcare transaction processing? 20:39 Why these transaction delays affect care delay. 23:14 EP482 with Preston Alexander. 23:18 EP472 with Eric Bricker, MD. 27:10 How should the process work from the time a provider clicks "validate"? 30:19 Why is the clearinghouse the right place to solve all these issues? 31:41 Why are we where we are in terms of these issues? 35:28 Why people should be looking at their clearinghouse costs. 36:59 What to know about Stedi.   You can learn more at stedi.com. You can also follow Zack and Stedi on LinkedIn.   @zackkanter discusses #healthcaretransactions and #clearinghouses on our #healthcarepodcast. #healthcare #podcast #financialhealth #patientoutcomes #primarycare #digitalhealth #healthcareleadership #healthcaretransformation #healthcareinnovation   Recent past interviews: Click a guest's name for their latest RHV episode! Mark Newman, Stacey Richter (INBW45), Stacey Richter (INBW44), Marilyn Bartlett (Encore! EP450), Dr Mick Connors, Sarah Emond (EP494), Sarah Emond (Bonus Episode), Stacey Richter (INBW43), Olivia Ross (Take Two: EP240)

My guests today are Tom Digan and Greg Stewart. Tom is the co-founder of Ladder, and Greg is its CEO. Ladder was my first angel investment. What followed over the next seven years is one of the most unlikely and dramatic business stories I've been a part of. Today, Ladder is the number one grossing fitness app in the App Store, approaching $100M in ARR with more than 300,000 paying members. But the path from near death to dominance involved debt collectors, leadership changes, and a full reset during the pandemic. Tom and Greg built Ladder by being relentlessly empirical about their customers, ruthless about prioritization, raising money wherever they could, and doing whatever it took when most founders would have quit. We cover the messy early years when survival meant negotiating creditors, how they found PMF by reading thousands of app store reviews, and how they built a TikTok growth engine with no performance marketing experience. They share their long-term vision for becoming the category winner for health and fitness and the impact of AI and GLP-1s on their business. This is a conversation about how hard it really is to build something valuable, told by two people who lived through all of it. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp's mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Vanta. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest.  ----- This episode is brought to you by Rogo. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at Rogo.ai/invest. ----- This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps (00:00:00) Welcome to Invest Like The Best  (00:04:26) Episode Intro (00:05:45) Ladder: The #1 Fitness App (00:09:28) The Messy, Early Years (00:14:47) Sponsors (00:16:20) The Darkest Point (00:18:17) Why Greg Joined Ladder (00:19:45) The Turning Point: Ladder 2.0 (00:21:57) The Key to Negotiating with Creditors (00:23:16) Fundraising Challenges and Strategies (00:25:50) Developing Ladder Teams (00:31:31) Listen to Your Customers (00:32:57) Launching Nutrition (00:38:53) Sponsors (00:39:31) Don't Listen to Investors on Product Feedback (00:40:18) The Cave Process (00:43:13) Crossing the Chasm (00:43:53) How to Crack TikTok (00:51:10) The Content Frontier (00:52:07) Controlled Bets at Scale (00:54:19) Why you should Build a B2C Company (00:57:37) The Impact of AI and GLP-1s (01:02:32) Sponsors (01:02:53) Staying Focused on the Core Product (01:05:00) Building the System of Record for Health and Fitness (01:09:45) What It's Like Talking to Investors Now (01:12:32) The Kindest Thing

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Bob Fraser, bestselling author of Invest Like a Billionaire and CFO and Chief Macro Strategist at Aspen Funds. Bob shares how billionaire investors moved away from traditional 60/40 portfolios toward alternative investments—and why everyday investors can adopt the same mindset without billionaire-level wealth. Throughout the conversation, Bob explains why professionally managed real estate is often the most approachable entry point into alternatives, especially for investors who want exposure without taking on a second full-time job. He and Jonathan explore the differences between active and passive investing, the importance of aligned partnerships, and why many investors underestimate the operational demands of being a landlord. The discussion then dives deep into macro-driven investing, with Bob outlining why industrial real estate stands out today due to reshoring trends, logistics demand, and lower construction and operational complexity compared to multifamily. Bob also explains why fund structures can be more efficient than single-asset syndications, offering better capital deployment, diversification, and investor control—especially around taxes and liquidity. In this episode, you will hear: Why billionaires shifted away from traditional portfolios toward alternatives How everyday investors can think like billionaires without massive capital The difference between active real estate and truly passive investing Why industrial real estate is outperforming multifamily in the current cycle How fund structures can improve diversification, tax efficiency, and liquidity What macro trends Bob looks for when evaluating alternative investments Follow and Review If you enjoy the show, please follow Zen and the Art of Real Estate Investing on Apple Podcasts and leave a rating and review. It helps other listeners discover these conversations and supports the show's growth. Supporting Resources Connect with Bob: Website: http://aspenfunds.us/  Instagram: https://www.instagram.com/aspenfunds  LinkedIn: https://www.linkedin.com/in/bobfraser10/  Connect with Jonathan: Website - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos  Instagram - www.instagram.com/trustgreene  Instagram - www.instagram.com/streamlinedproperties    Zillow - www.zillow.com/profile/streamlinen​j Bigger Pockets -  www.biggerpockets.com/users/jonathangreene Facebook - www.facebook.com/streamlinedproperties  Email - info@streamlined.properties   This episode was produced by Outlier Audio.

My guest today is Reed Hastings, the co-founder and former longtime CEO of Netflix. Netflix is an example of two ideas that everyone talks about, but are extremely hard to do in practice. The first is finding a simple idea and taking it extraordinarily seriously. Reed talks about how even the DVD business was nothing more than a stepping stone toward streaming, which they envisioned from the company's inception in 1997. The second is talent density, and what it actually takes to set and sustain an exceptionally high bar over decades as a company grows.  We talk about how those ideas shaped Netflix's culture and strategy, what Reed learned from mistakes like Qwikster, and why Netflix treated content like a venture portfolio. We also discuss Reed's work today. He shares how he's thinking about AI, what he's learned from serving on the boards of Microsoft, Meta, Anthropic, and Bloomberg, and what excites him about Powder Mountain, the ski resort he acquired after Netflix. Please enjoy my conversation with Reed Hastings. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp's mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ramp.com/invest⁠ to sign up for free and get a $250 welcome bonus. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Vanta. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest.  ----- This episode is brought to you by Rogo. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at Rogo.ai/invest. ----- This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps (00:00:00) Sponsors (00:03:33) Welcome to Invest Like The Best (00:04:29) Intro (00:05:43) Sponsors (00:07:16) The Concept of Talent Density (00:11:19) Evaluating Talent (00:13:47) Managing on the Edge of Chaos (00:14:51) Why Netflix Gave Large Severance Packages (00:16:37) The Keeper's Test (00:17:07) The Qwikster Mistake (00:19:15) The Informed Captain (00:20:39) How to Come Up with Good Ideas (00:22:32) Transitioning to Streaming (00:23:05) Being on the Board of Facebook, Microsoft, Anthropic & Bloomberg (00:26:25) The Role of a Board Member (00:29:37) Sponsors (00:30:15) Why Netflix Had Open Compensation (00:32:04) Netflix's Content Strategy (00:37:52) Competing with YouTube and Traditional TV (00:39:23) Creating Hit Content (00:40:02) Impact of AI on Netflix (00:41:24) Innovations in Show Formats (00:43:23) Sponsors (00:43:44) Netflix's Technology Backbone (00:45:29) Expanding into Gaming (00:46:06) Lessons from Failed Projects (00:47:30) Financial Strategy and Capital Allocation (00:50:27) Stepping Down as CEO (00:50:52) Powder Mountain (00:56:08) Focus on Education and AI (00:59:00) Risks and Benefits of AI (01:00:56) The Kindest Thing (01:02:56) Sponsors

Today, I am replaying my conversation with Nick Kokonas, one of my favorites from the show. Nick is the co-founder of 3 of the best restaurants and bars in America - Alinea, Next, and The Aviary as well as the co-founder and CEO of Tock, a comprehensive booking system for restaurants. He majored in philosophy before becoming a derivatives trader and is now one of the most well-known names in the hospitality industry. In this conversation, Nick shares his experience of bringing a business mindset to the restaurant industry. I'll remember it for why it's so important for a business to really know what it's selling and then actually sell it. Nick also pulls back the curtain on why restaurants and even book publishers can be great businesses if you do them the right way. I felt like this conversation could have gone on for hours and I hope you enjoy it. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp's mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ramp.com/invest to sign up for free and get a $250 welcome bonus. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform. ----- This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Timestamps: (00:00) Welcome to Invest Like The Best (03:58) Intro to Nick Kokonas (4:36) – Why it's so important to own something (6:09) – Make decisions that have outcomes (8:34) – His interest in the restaurant business (10:28) – Why restaurants are so tough (13:39) – How their business mindset changed their running of the restaurant (16:09) – Words they would avoid in the restaurant (17:53) – Asking the right questions in the restaurant business (22:14) – Importance in taking the right risks (23:36) – Coming up with innovative strategies for ticketing, selling meals ahead of time, and dynamic pricing (31:42) – Can dynamic pricing be extended to other businesses (32:54) – Origin of Tock (37:51) – Early days of Tock and identifying the right customers/challenges (43:07) – Importance of the first customer (45:56) – The typical restaurant business model (50:57) – Lessons from Tock and the importance of knowing what you're selling (55:21) – Lessons from publishing (57:18) – Other aspects of business that people know but do nothing about (1:01:53) – Their response to Covid and lessons learned (1:09:17) – The real impact to the food delivery companies (1:10:58) – How businesses communicate their end processes to their customers (1:15:41) – The Kindest Thing

Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS] Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. Ric Elias is the CEO and co-founder of Red Ventures, which has a portfolio of fast-growing digital businesses like Lonely Planet, The Points Guy, Bankrate, and large investments in a variety of other businesses across industries. He began the business in 2000 and has grown it to now a global company with thousands of employees. Ric walks us through the early struggles that have led to what is now a flourishing investing platform, but mostly this episode is a masterclass on cultural values and philosophies that transcend mere financial gain. We discuss the difference between living good and well, the power of forgiveness, and compounding more than just your capital. Ric's story is one of resilience, humility, and grace. His story about being in the front row of the plane that Captain Sully landed in the Hudson is singular and very moving. Please enjoy my conversation with Ric Elias. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by WorkOS. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit WorkOS to Transform your application into an enterprise-ready solution in minutes, not months. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @joincolossus ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:02:00) Meet Ric Elias (00:02:49) Chasing the Big Dream (00:05:38) Understanding Red Ventures: Origin and Evolution (00:10:25) Operational Success and Company Culture (00:25:30) Reflections on Money and Personal Well-being (00:28:49) The Difference between Good and Well (00:32:55) The Hudson River Plane Crash Experience (00:42:37) Reconnecting with Puerto Rico and Reviving the Basketball Team (00:45:07) Underdogs to Champions (00:48:09) How to Build Trust and Culture (00:52:29) Reflections on Leadership (00:56:12) The Role of Confidence and Courage (00:59:38) The Value of Family and Friendships (01:01:57) The Pursuit of Purpose Over Profit (01:06:52) Recruitment and Company Culture (01:10:07) Reflecting on Success (01:14:33) The Importance of Pace and Speed (01:16:23) Other Business Philosophies (01:23:17) The Kindest Thing

My guest today is Henry Ellenbogen, founder and Managing Partner of Durable Capital Partners. Henry built his reputation at T. Rowe Price, where he led the New Horizons Fund and turned it into one of the best-performing small-cap growth portfolios in the country. In 2019, he left to start Durable. His philosophy is grounded in a simple belief that great investing is about understanding people and change. Henry has spent his career studying the rare 1% of companies that drive nearly all long-term returns . Durable's edge comes from being able to tell the difference between a company that is failing and one that is transforming. Henry often talks about “Act II” teams – founders who take the lessons from their first company and apply them to a new frontier. Durable itself is his Act II. In our latest Colossus profile, Managing Editor Dom Cooke traces Henry's story and specifically how he became one of the most influential investors of the 21st century, having learned from founders like Jeff Bezos and John Malone in the early part of his career. I always hear the same thing from founders who've met Henry: “he understood my business faster than anyone”. The thing that sticks with me from our conversation and Dom's profile is just how much he loves investing. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ramp's mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ramp.com/invest to sign up for free and get a $250 welcome bonus. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about the platform. ----- This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Alpha-Sense.com/Invest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠). Show Notes: (00:00:00) Welcome to Invest Like The Best (00:04:00) Meet Henry Ellenbogen (00:05:29) Origin of Henry's Investment Philosophy (00:08:12) Identifying the 1% of Great Companies (00:12:53) Patterns of Successful Compounders (00:20:34) Act Two Entrepreneurs and Teams (00:25:43) Building Durable Capital: Henry's Act Two (00:30:11) Dollar Cost Averaging Up Strategy (00:35:02) Market Structure and Agency Problems (00:38:26) Impact of Quant Funds and Short-Term Capital (00:42:21) AI as Transformative Change (00:45:30) How Affirm Uses AI (00:48:23) Amazon's Cost Curve Advantage (00:51:48) Leadership Through Change (00:56:54) Robotics and Physical Kaizen (01:01:29) Favorite Types of Competitive Advantages (01:05:25) Investment Memo Structure (01:09:21) 2022 CEO Tour on Market Transition (01:19:18) Hiring and Developing Talent (01:24:09) Making Colleagues Better (01:27:56) Being Intellectually Honest in Investing (01:29:11) Lessons from Success (01:33:04) Case for Going Public (01:36:32) Netflix Transition Example (01:41:29) Two Types of Greatness (01:45:42) The Kindest Thing

Tobi Lütke is a German born Canadian who built a multibillion-dollar company from a snowboard shop; champions economic freedom for regular people starting businesses; combines old-world craftsmanship with modern innovation. He is an entrepreneur, software developer, best known as the co-founder and CEO of Shopify, a leading e-commerce platform powering over 4 million merchants worldwide as of 2024, generating billions in annual revenue. Born in Germany, Lütke discovered his passion for coding at a young age with a Schneider CPC computer, rewriting game code by age 11. A self-taught programmer who dropped out of school after tenth grade to pursue a computer programming apprenticeship at Koblenzer Carl-Benz-School, he moved to Canada in the early 2000s. In 2004, as a snowboard enthusiast, Lütke co-founded Snowdevil, an online snowboard shop, but frustrations with existing e-commerce tools led him to build a custom platform using Ruby on Rails, which became Shopify in 2006 in Ottawa, Canada. Under his leadership, Shopify went public in 2015, reaching a market capitalization exceeding $100 billion at its peak. He is a core contributor to Ruby on Rails and creator of open-source libraries like Active Merchant. Lütke joined Coinbase's board in 2022. Tobi is a competitive racing driver in the 2025 IMSA SportsCar Championship's LMP2 class for Era Motorsport. He is married to Fiona McKean, a former Canadian diplomat, with three children. He co-founded the Thistledown Foundation, supporting environmental causes through initiatives like Shopify's Sustainability Fund. Lütke advocates for ethical technology, small business empowerment, and innovative leadership, often speaking on platforms like Invest Like the Best about building sustainable tech ecosystems. Shawn Ryan Show Sponsors: Visit https://shopbeam.com/SRS and use code SRS to get our exclusive discount of up to 50% off. Go to https://ShawnLikesGold.com right now to get your free 2025 Gold & Silver Kit. Ready to upgrade your eyewear? Check them out at https://roka.com and use code SRS for 20% off sitewide. Upgrade your routine with Caldera Lab and see the difference for yourself. Go to https://CalderaLab.com/SRS and use SRS at checkout for 20% off your first order. Tobi Lütke Links: X - https://x.com/tobi IG - https://www.instagram.com/tobi Get started with Shopify - https://shopify.com/srs Learn more about your ad choices. Visit podcastchoices.com/adchoices