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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 Alex Sacerdote, founder of Whale Rock Capital Management. Whale Rock is a technology focused investment firm that manages more than $17 billion across hedge fund, long only, and hybrid strategies. Over the past three years it has been one of the best performing hedge funds, compounding at roughly 44 percent a year. Alex invests through a single lens that he has refined over twenty years. He looks for technology S-curves, durable competitive advantages, and underappreciated earnings power. This conversation is a tour through how he applies that framework right now. We start with his highest conviction position, which is Anthropic, and use it to work through the entire AI stack from chips to models to applications. Please enjoy my conversation with Alex Sacerdote. 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. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to vanta.com/invest. ----- WorkOS is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- 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 (00:00:00) Welcome to Invest Like The Best (00:02:29) Alex Sacerdote (00:03:08) Anthropic: Highest Conviction Position (00:13:23) Investing in Private Markets at Scale (00:19:08) S-Curves: The Full Framework (00:25:08) When to Buy Tech Companies (00:30:20) Identifying the Leader from the Pack (00:34:04) Anthropic & OpenAI's Competitive Moats (00:37:31) AI's Threat to Enterprise Software (00:43:18) Network Effects in the Agent Era (00:44:22) The Hardware Renaissance: Chips & Infrastructure (00:53:56) Why So Few Investors Get This Right (00:55:36) Key Risks to the AI Bull Case (00:57:47) The Application Layer (00:59:40) How AI Is Changing Research at WhaleRock (01:02:53) The Role of Investor Networks & Idea Sharing (01:03:40) Building a Multi-Product Firm (01:07:58) WhaleRock as a Learning Machine (01:09:15) 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 hereIs leverage really the risky part of wealth building — or is the bigger risk misunderstanding how, when, and why to use it?Many Canadian business owners and investors already use leverage every day through mortgages, vehicle financing, business debt, or lines of credit — yet borrowing to invest often feels like a completely different level of risk. In this episode, Kyle and Jon unpack why some forms of debt feel “normal” while others feel dangerous, and how education, experience, asset choice, and the right support can dramatically change how risk is perceived. If you've ever wondered whether leveraged investing is smart strategy or unnecessary danger, this conversation will help you think more clearly about the difference.You'll walk away with:A clearer way to compare “acceptable” debt, like mortgages, with investment leverage that may create income or tax advantages.A practical lens for understanding objective risk versus perceived risk — and why your experience with an asset class matters.A better sense of when leverage may be an opportunity, when it may be a red flag, and why guidance or deeper education can help reduce costly mistakes.Press play now to rethink leverage, risk, and opportunity through a more strategic wealth-building 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 Kyle if 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 large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.For Canadian entrepreneurs and investors, building long-term wealth Canada starts with a clear Canadian wealth plan that connects leverage, risk management, investment strategies, financial education, and tax optimization into one intentional system. Whether you are comparing real estate investing Canada with real estate vs renting, exploring passive income planning, optimizing RRSP room, or weighing salary vs dividends Canada, the goal is to use smart financial planning, personal vs corporate tax planning, and corporation investment strategies to reduce investment risk while creating more financial freedom Canada. A strong plan may include RRSP optimization, tax-efficient investing, Canadian tax strategies, capital gains strategy, corporate wealth planning, business owner tax savings, corporate structure optimization, and financial systems for entrepreneurs, all supported by retirement planning tools, financial buckets, an investment bucket strategy, and financial vision setting. By focusing on financial diversification Canada, modest lifestyle wealth, early retirement strategy, passive income, estate planning Canada, legacy planning Canada, and financial independence Canada, Canadians can create wealth building strategies Canada that balance real estate, corporate assets, tax planning, and long-term investment risk management.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.
My guest today is Alex Sacerdote, founder of Whale Rock Capital Management. Whale Rock is a technology focused investment firm that manages more than $17 billion across hedge fund, long only, and hybrid strategies. Over the past three years it has been one of the best performing hedge funds, compounding at roughly 44 percent a year. Alex invests through a single lens that he has refined over twenty years. He looks for technology S-curves, durable competitive advantages, and underappreciated earnings power. This conversation is a tour through how he applies that framework right now. We start with his highest conviction position, which is Anthropic, and use it to work through the entire AI stack from chips to models to applications. Please enjoy my conversation with Alex Sacerdote. 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. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to vanta.com/invest. ----- WorkOS is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- 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 (00:00:00) Welcome to Invest Like The Best (00:02:29) Alex Sacerdote (00:03:08) Anthropic: Highest Conviction Position (00:13:23) Investing in Private Markets at Scale (00:19:08) S-Curves: The Full Framework (00:25:08) When to Buy Tech Companies (00:30:20) Identifying the Leader from the Pack (00:34:04) Anthropic & OpenAI's Competitive Moats (00:37:31) AI's Threat to Enterprise Software (00:43:18) Network Effects in the Agent Era (00:44:22) The Hardware Renaissance: Chips & Infrastructure (00:53:56) Why So Few Investors Get This Right (00:55:36) Key Risks to the AI Bull Case (00:57:47) The Application Layer (00:59:40) How AI Is Changing Research at WhaleRock (01:02:53) The Role of Investor Networks & Idea Sharing (01:03:40) Building a Multi-Product Firm (01:07:58) WhaleRock as a Learning Machine (01:09:15) The Kindest Thing
We'd love to hear from you. What are your thoughts and questions?Bob Fraser, CFO and Chief Macro Strategist of Aspen Funds, a private fund sponsor with a 12 year track record, distributing over $85M to investors, and over $700M in AUM across private credit, commercial real estate, distressed debt, and energy, shares insights on how the ultra wealthy build and protect wealth through strategic structuring, private investments, and risk management, emphasizing the limitations of public markets and the advantages of private alternatives.Main Points: Volatility drag and its impact on long-term compoundingLimitations of diversification in public marketsAdvantages of private alternatives for risk reductionHow billionaires think differently about volatility and riskOperator due diligence and risk mitigation in private marketsThe democratization of private market investing post-2012Practical steps for high-income professionals to access private investmentsConnect with Bob Fraser:bob@aspenfunds.ushttps://www.linkedin.com/in/bobfraser10/https://www.instagram.com/ritteronrealestate/https://www.youtube.com/@investlikeabillionairepodcast
My guest today is Dara Khosrowshahi, the CEO of Uber. Before Uber, Dara ran Expedia for thirteen years. We start with why he took this job in 2017, and a big part of that story is Daniel Ek, who told him that life is not about happiness, it is about impact. We talk about what the chaos felt like on day one, and how his family leaving Iran when he was nine shaped the way he handles pressure today. We spend most of our time on autonomous vehicles and Uber's role as the demand aggregator in a world of physical AI. Dara explains why Uber is a supply-led company, what it will take to win, and why he expects many winners in AVs rather than one. We also discuss Uber's $10 billion in free cash flow, the push toward a single app for everything, and what he has learned from Allen & Co, Barry Diller and Reed Hastings. 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. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to vanta.com/invest. ----- WorkOS is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- 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 (00:02:29) Intro to Dara Khosrowshahi (00:03:37) How Daniel Ek Convinced Dara to Take the Uber Job (00:06:54) Bringing Order to Chaos (00:09:20) Managing Stress as a Leader (00:11:22) The Chip on His Shoulder (00:12:53) Parenting Lessons (00:17:01) Mandate for AI Adoption (00:21:21) Uber's Role in Physical AI (00:22:48) Winning the AV Demand Race (00:27:41) Partnering vs. Competing with Waymo (00:32:05) AV Success Unlocks New Markets (00:35:09) Why Drones Haven't Arrived Yet (00:36:27) Regional AV Rollout Differences (00:37:35) Uber Eats International Winning Formula (00:39:44) Key to Aggregating Supply Well (00:44:34) Adding Hotels to Uber Platform (00:50:46) Lessons in Marketing at Scale (00:52:59) Apps vs. AI Agents in Seven Years (00:54:08) What Dara Learned from Barry Diller (00:56:52) What Dara Learned from Allen & Co (01:00:09) Buybacks vs. Growth Investing (01:04:17) Lessons from Reed Hastings (01:05:49) 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 hereIs Ontario's small business tax cut actually saving you money—or just shifting the tax bill somewhere else?A lower corporate income tax rate sounds like a win for business owners, especially when headlines make the cut look dramatic. But if you eventually need to pull retained earnings out of your corporation, the personal tax side matters just as much as the corporate savings. This episode breaks down what the change really means, why the “savings” may not be as generous as they appear, and how business owners should think more strategically about salary, dividends, and retained earnings.You'll walk away with:A clearer understanding of how Ontario's small business tax cut affects active corporate income.The round-trip math behind saving tax inside the corporation versus paying more when dividends come out personally.Key planning questions to consider around retained earnings, passive income, salary, dividends, and long-term tax efficiency.Press play now to understand whether this tax change helps your business—or quietly creates a bigger planning problem down the road.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 if 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 large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.For Canadian entrepreneurs, building a strong Canadian wealth plan starts with understanding how small business taxin Ontario, a corporate tax cut, dividend tax, and personal vs corporate tax planning can impact long-term decisions around tax planning, business strategy, and wealth management. Whether your goal is financial freedom Canada, financial independence Canada, or an early retirement strategy, the right approach may include corporate wealth planning, salary vs dividends Canada, RRSP optimization, optimizing RRSP room, tax-efficient investing, passive income planning, and smart corporation investment strategies. For business owners pursuing modest lifestyle wealth, legacy planning Canada, and building long-term wealth Canada, it's important to align financial buckets, an investment bucket strategy, financial vision setting, retirement planning tools, and financial systems for entrepreneurs with practical Canadian tax strategies, business owner tax savings, capital gains strategy, and corporate structure optimization. From real estate investing Canada and real estate vs renting to financial diversification Canada, passive income, and estate planning Canada, the best wealth building strategies Canadahelp connect today's cash flow decisions with tomorrow's freedom, security, and family legacy.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.
My guest today is Dan Loeb, the founder and CEO of Third Point. Dan started Third Point in 1995 with a few million dollars, and today the firm manages over 24 billion across equities, corporate and structured credit, venture, and insurance. He is best known for his activist work at companies like Sotheby's, Sony, and Yahoo, and for the public letters he has written to boards over the years. What I find most interesting about Dan is how much his approach has evolved across thirty years. He came up as a credit and event-driven investor at Warburg Pincus and Jefferies, built Third Point, then layered in quality investing, thematic technology investing, and now a very large credit business that sits alongside the hedge fund. We cover how he thinks about the AI stack and the companies inside it he believes matter most, the difference between good and bad governance, what FTX taught him about due diligence, the Sony and Sotheby's stories, and the power of writing. Please enjoy my conversation with Dan Loeb. 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. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to vanta.com/invest. ----- WorkOS is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- 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 (00:02:29) Dan Loeb (00:03:21) Mental Models Information Overload (00:06:50) Dan's Identity as an Investor (00:11:24) The End of Classic Event-Driven Investing (00:13:52) Evolving Strategy Over 30 Years (00:17:48) Return Opportunities in Today's Market (00:21:12) Sources of Alpha for Fundamental Investors (00:22:10) Good vs. Bad Governance (00:26:17) Writing as an Investing Tool (00:27:29) The Sotheby's Story (00:30:04) Activism Opportunities Today (00:31:03) Third Point's Evolution to 60% Credit (00:36:10) Dan as Sole Portfolio Manager (00:38:09) Value Investor Perspective on Today's Market (00:39:23) Investing Outside the US (00:40:33) The Sony Activism Story (00:43:59) Lessons from 30 Years of Investing (00:46:26) Danaher and Operational Excellence (00:48:48) Building the Insurance Liability Business (00:51:19) The FTX Story (00:53:07) Leading a Team Through Uncertainty (00:54:29) Where Third Point Is Most Contrarian (00:56:22) What Makes a Great Analyst Today (00:58:12) The Next 10 Years (01:00:24) 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 your corporate retained earnings really worth what you think they are once they finally reach your family's hands?If you've built up cash inside your corporation or holding company, it can feel like that money is fully part of your net worth. But once passive income taxes, dividend taxes, and the small business deduction grind come into play, the number on paper can look very different from what actually lands in your personal pocket. This episode helps incorporated business owners rethink retained earnings not just as “money in the corporation,” but as dollars that need a smart path to eventually reach human hands.You'll walk away with:A clearer understanding of why passive income inside a corporation can trigger heavy tax drag and reduce access to the small business tax rate.A practical way to compare income-producing investments versus capital-appreciating assets inside a corporate structure.Insight into how strategies like the capital dividend account and corporate-owned life insurance may support tax-efficient cash flow, legacy planning, and long-term wealth transfer.Press play now to learn how to think more strategically about retained earnings, corporate investing, and getting more of your business wealth into your family's hands.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 if 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 large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.A strong Canadian wealth plan for incorporated business owners starts with understanding corporate retained earnings Canada, retained earnings tax, and the difference between personal vs corporate tax planning so you can make smarter decisions around salary vs dividends Canada, RRSP optimization, optimizing RRSP room, and long-term corporate wealth planning. For Canadian entrepreneur finance, the goal is often financial freedom Canada, financial independence Canada, or an early retirement strategy built around modest lifestyle wealth, financial buckets, an investment bucket strategy, and practical retirement planning tools. Whether you are comparing real estate investing Canada, real estate vs renting, holding company investments, or other corporation investment strategies, the right approach should consider passive income corporation Canada, passive income planning, the small business deduction grind, capital gains strategy, the capital dividend account, corporate-owned life insurance, and broader Canadian tax strategies. With thoughtful corporate structure optimization, tax-efficient investing, business owner tax savings, financial systems for entrepreneurs, and financial diversification Canada, Canadian business owners can create stronger wealth building strategies Canada, support building long-term wealth Canada, clarify their financial vision setting, and strengthen legacy planning Canada and estate planning Canada through a more intentional corporate wealth strategy.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.
My guest today is Darren Farber, and this is his second appearance on the show. Darren is a Managing Partner of Albion River, a defense-focused investment firm and he previously served as a special advisor to the Deputy Under Secretary of Defense. We recorded this conversation in the middle of the Iranian contingency, and we spent most of our time on what winning actually means in a theater like Iran. We discuss why magazine depth matters for the American industrial base, lessons from Ukraine, and what the rise of neo-prime defense companies will require from Congress. Please enjoy my second conversation with Darren Farber. 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. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to vanta.com/invest. ----- WorkOS is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- 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 (00:02:29) Darren Farber Intro (00:02:59) Defining What Winning Looks Like in Iran (00:12:16) The Strait of Hormuz (00:13:27) Eisenhower vs. Taylor: Two Military Doctrines Explained (00:17:12) US Military Readiness vs. the Pentagon Era (00:20:05) America's Magazine Depth (00:21:36) China's Vulnerability (00:25:28) Trading Freedom for Security (00:27:31) Today's Industrial Base (00:29:30) Lessons from the Ukraine War (00:31:11) Impact of Iran Conflict on Taiwan Risk (00:33:02) What Neo-Prime Defense Companies Need to Succeed (00:39:53) Can We Win Without Full Regime Change in Iran? (00:45:46) AI's Impact on Modern Warfare
Invest Like a Billionaire - The alternative investments & strategies billionaires use to grow wealth
Bourbon might be one of the most overlooked alternative investments in America.In this episode of Invest Like a Billionaire, Brian Rosen, founder of InvestBev, breaks down how his firm built a portfolio around bourbon barrels, beverage brands, and alcohol infrastructure and why family offices are paying attention.We cover:• Why bourbon barrels have historically produced strong returns• The “dirty secret” behind most liquor brands• How billionaires invest in beverage infrastructure• Why alcohol is considered a non-correlated asset• The macro trends reshaping the beverage industryHave more questions, or want more resources like a tax calculator? Go to https://investlikeabillionaire.org/ to learn more about our community. Check out Ben & Bob's company and invest along at https://aspenfunds.us/
My guest today is Gavin Baker, founding partner and CIO of Atreides Management, and this is our sixth conversation. The central theme is watts and wafers, the two physical constraints that in Gavin's view will dictate the next phase of AI. On power, he thinks the near-term shortage starts to ease in 2027 and 2028 as new sources of energy come online, and that orbital compute solves it in the long term. On wafers, he explains what is different this time from the dotcom bubble and why TSMC's capacity decisions may be the single most important variable to watch. We also discuss Elon's Terrafab, the disaggregation of GPUs, the role of new chip companies, and whether the economic value of AI will keep accruing to frontier models. 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. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to vanta.com/invest. ----- WorkOS is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- 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 (00:02:29) Gavin Baker Intro (00:03:32) Anthropic's Record ARR Growth (00:11:49) Should OpenAI and Anthropic Raise at a Much Higher Valuation? (00:13:23) How Elon Preserves Investor Trust (00:14:00) Watts & Wafers (00:15:45) Data Centers in Space Explained (00:20:51) Orbital Compute's Impact on Terrestrial Data Centers (00:26:24) TSMC Supply Discipline & Bubble Risk (00:30:50) Demand for Frontier Tokens & The Bitter Lesson (00:35:33) Continual Learning & Memory (00:40:01) New Chip Companies & Startups (00:42:49) Prefill vs. Decode Disaggregation (00:48:40) AI-Native Founders: Different & Hard (00:51:27) Token Path & Application Layer (00:56:13) How Gavin Uses AI in Atreides (01:00:06) Signs of a Diversity Breakdown (01:05:42) Google, Meta, Amazon, Microsoft (01:11:42) Broader Knock-On Effects of AI
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 chasing a tax-saving strategy that sounds smart—but may not be the biggest financial opportunity in front of you?In this episode, Jon Orr and Kyle Pearce unpack a real-world Canadian wealth planning scenario involving rental properties, cash damming, the Smith Manoeuvre, a primary residence mortgage, and retained earnings inside a corporation. While strategies like cash damming can create tax-deductible interest, the episode challenges listeners to step back and ask whether the time, complexity, and bookkeeping are actually worth the payoff right now. For business owners and real estate investors, the bigger win may come from identifying the highest-impact planning opportunity before getting lost in the weeds of smaller optimizations.You'll walk away with:A clearer understanding of how cash damming fits within the Smith Manoeuvre and why the purpose of borrowed funds matters.A practical way to think through whether a tax deduction is meaningful enough to justify the effort.A reminder to compare small tax-saving moves against larger planning opportunities, especially when corporate retained earnings and future tax exposure are involved.Press play now to learn how to spot the difference between a clever financial tactic and the strategy that may matter most.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 if 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 large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.Cash Damming and the Smith Manoeuvre are popular Canadian tax strategies, but the real question for Canadian investors, entrepreneurs, and business owners is whether these moves fit into a bigger Canadian wealth plan. In this episode of Canadian Wealth Secrets, we explore how Tax Planning Canada, Rental Properties, HELOC Strategy, and Canadian Real Estate Investing can work together with Corporate Wealth Planning, Retained Earnings, and Business Owner Tax Strategy to support long-term goals like financial freedom Canada, early retirement strategy, passive income planning, and financial independence Canada. For incorporated professionals, the conversation goes beyond real estate investing Canada and looks at salary vs dividends Canada, personal vs corporate tax planning, corporation investment strategies, corporate structure optimization, business owner tax savings, and tax-efficient investing. You'll also hear why modest lifestyle wealth, RRSP optimization, optimizing RRSP room, financial buckets, investment bucket strategy, capital gains strategy, estate planning Canada, legacy planning Canada, and financial vision setting all matter when building long-term wealth Canada. Whether you're comparing real estate vs renting, planning for retirement, exploring retirement planning tools, improving financial systems for entrepreneurs, or seeking better financial diversification Canada, this episode helps you focus on wealth building strategies Canada that align with your lifestyle, tax situation, and future goals.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.
Guest Joseph Barrato Founder & CEO of Arrow Investment AdvisorsWebsitehttps://arrowfunds.com/BioJoseph Barrato is the Founder and CEO of Arrow Investment Advisors, where he has spent nearly two decades developing institutional-style portfolio solutions designed to help financial advisors navigate changing market environments through diversification, tactical allocation, and alternative investments.With more than 25 years of experience spanning ETF innovation, quantitative modeling, managed futures, and tactical portfolio construction, Joe has been involved in the development of several pioneering investment structures throughout his career. Prior to founding Arrow in 2006, he held leadership roles at Rydex Investments, where he worked on research, momentum modeling, and product development initiatives that contributed to some of the earliest innovations in smart beta, tactical allocation, and ETF portfolio design, including work associated with the Invesco S&P 500 Equal Weight ETF.Earlier in his career, Joe spent 12 years at the Federal Reserve Board of Governors, where he worked as both a financial analyst and senior financial examiner supporting economists, analyzing monetary data, and advising Federal Reserve officials on financial and operational matters.Under Joe's leadership, Arrow became an early adopter of managed futures within the 40 Act structure and today manages one of the industry's longest-running managed futures strategies in a mutual fund wrapper. Arrow has also helped develop innovative solutions across tactical balanced portfolios, global macro strategies, income-oriented ETFs, and Tactical Bitcoin strategies focused on managing volatility within digital assets.In addition to portfolio management and product development, Joe regularly publishes market commentary and portfolio research through Arrow Insights, focusing on portfolio construction, volatility, diversification, and evolving market structure. He is also actively involved in charitable and community outreach initiatives, including Dividend Angels and service-oriented programs supporting recovery and underserved communities in Baltimore.Joe's investment philosophy centers on a belief that portfolio structure matters just as much as asset selection. His work has consistently focused on helping advisors incorporate non-correlated exposures, systematic disciplines, and dynamic allocation frameworks into modern portfolio construction.
With nearly 40 years in tax and wealth management, Mark Miller helps business owners, executives, and high-net-worth individuals build, protect, and sustain their wealth. As a best-selling author, his book Hilton Wealth: How to Invest Like an American Dynasty reveals the investment and tax strategies used by Fortune 500 firms and the Hilton family. Featured in over 200 major publications, including Kiplinger's, The New York Times, and Money Magazine, Mark has also appeared as a financial expert on Fox News and national media. Recognized as a Presidential Businessman of the Year, he received a personal commendation from President George W. Bush. Miller is the Managing Director of the Hilton Family office and CEO of Hilton Tax and Wealth Advisors, partnered with J. Bradley Hilton, the grandson of the legendary Hotelier Conrad Hilton. Via their Hilton TruWealth Portfolios™, Mark empowers clients with Smart Money level wealth-building strategies, ensuring financial security and lasting legacies. Hilton's mission is to help clients invest and grow wealth like an American Dynasty.
My guest today is Krishna Rao, the CFO of Anthropic. The center of our conversation is how he navigates the decision around procuring and allocating compute, which he describes as the canvas on which everything else gets built. We talk about what he calls the cone of uncertainty, the three chip platforms Anthropic uses fungibly across Trainium, TPUs, and GPUs, and the daily meetings they run to allocate compute between model development, internal use, and serving customer demand. He explains why the returns to frontier intelligence keep getting higher, especially in enterprise, and how Anthropic thinks about the line between platform and application and why they choose to build their own products like Claude Code. Krishna has such a unique seat watching one of the fastest growing businesses in history, and he is generous in sharing what he has learned since joining the company two years ago. 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. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to vanta.com/invest. ----- WorkOS is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- 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 (00:02:29) Episode Intro: Krishna Rao (00:03:14) Compute as Anthropic's Lifeblood (00:05:17) Three Fungible Chip Platforms (00:07:31) The Cone of Uncertainty (00:09:08) Competing Ways to Allocate Compute (00:10:36) What Drives Compute Efficiency (00:12:38) Why Frontier Returns Are So High (00:16:32) How Claude Code Writes Its Own Code (00:18:46) Will Talent Become Obsolete? (00:20:07) How Scaling Laws Are Holding (00:21:54) Exponential Thinking (00:23:17) The Layer Cake of Compute (00:26:36) How Anthropic Deploys New Compute (00:27:53) Platform v. Application Layer (00:32:42) Why Model Pricing Has Stayed Stable (00:35:26) Measuring Return on Compute (00:37:22) Working With Chip Providers (00:38:32) How Anthropic's Finance Team Uses Claude (00:41:32) The Jevons Paradox for Labor (00:43:08) Anthropic's Fundraising & Growth Journey (00:47:31) The Exponential Revenue Curve (00:49:02) The Hardest Thing to Explain to Investors (00:52:15) AI's Public Perception Problem (00:55:38) Mythos (00:57:31) Relationship With Government (00:58:51) Inside Anthropic's Culture (01:03:48) The Next Frontier: Virtual Collaborators (01:06:22) How Leaders Scale With a Business (01:10:55) The Biggest Risks to Continued Progress (01:12:09) What Krishna is Excited About (01:13:45) 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 hereCould your RRSP become one of your biggest future tax problems—and is there a smarter way to unwind it?Many Canadians spend decades building RRSP wealth, only to discover later that RRIF withdrawals can trigger a much larger tax bill than expected. This episode breaks down why the real issue is not the RRSP itself, but the lack of a coordinated system for withdrawals, deductions, leverage, and retirement cash flow. You'll hear how tax-efficient planning can begin well before retirement, especially for high-income Canadians, incorporated business owners, and anyone trying to preserve more of what they've built. In this episode, you'll learn:How RRSPs and RRIFs really differ—and why converting strategically can create more control over income, liquidity, and tax timing.What a true RRIF meltdown strategy involves, including how investment loan interest deductions can help offset taxable RRIF income.How self-made dividends and capital gains planning can support retirement cash flow while reducing reliance on fully taxable income sources.Press play now to learn how a more intentional RRSP and RRIF strategy could help you reduce future tax drag and create more flexibility in 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 if 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 large sum of liquid assets 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.
When corporations destroy the environment and ignore human rights, the loudest protests usually come from the streets. But while activists are calling for change from the outside, another movement is quietly working to steer these massive organizations from within. Discover how Friends Fiduciary is taking a seat at the shareholders' table, using Quaker values to persuade global brands to put humanity over quick profits. ----- Friends Fiduciary Is the Preferred Investment Manager for Quaker Meetings Guided by Quaker principles, values and testimonies, Friends Fiduciary Corporation provides prudent, cost-effective management of financial assets for Friends organizations. Overseeing assets exceeding $800 million and serving as trustees for more than 100 trusts, Friends Fiduciary is a preferred investment manager for Yearly, Quarterly, and Monthly Meetings of Friends. Friends Fiduciary employs a company screening process and is committed to active ownership, ensuring corporate accountability, and environmental sustainability. Discover more at www.FriendsFiduciary.org. Become a monthly supporter! Sign up for the Daily Quaker Message.
Bob Fraser reveals why billionaires keep only 20% in public markets and how private alternatives can protect and grow wealth — without chasing returns.In this episode of RealDealChat, Jack Hoss sits down with Bob Fraser, CFO and chief macro strategist of Aspen Funds and co-author of the USA Today bestseller Invest Like a Billionaire, to break down how the ultra-wealthy structure their portfolios and why most investors are playing the wrong game entirely.Bob covers:Why billionaires keep only 20-30% of their wealth in public marketsThe difference between diversification and true mathematical uncorrelationWhy the S&P 500 index is more concentrated than most investors realizeWhy public markets are driven by emotion and narrative rather than fundamentalsThe current valuation argument against public equities and what history says about forward returnsHow to evaluate private alternative investments by risk profileWhy oil and gas can function as an uncorrelated, cash-flowing assetThe natural gas thesis and its connection to AI energy demandHow the JOBS Act of 2012 opened private investing to accredited investorsRed flags to watch for when vetting syndicators and sponsorsWhy losses hurt compounding more than gains help itBob's personal story of being wiped out twice and what it taught himThis episode is essential for:Accredited investors looking to move beyond a traditional 60/40 portfolioReal estate investors who want to add true uncorrelation to their holdingsAnyone vetting private deals and syndicationsInvestors trying to understand where risk actually lives in their portfolio
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 spending your best time chasing small financial gains while your biggest opportunity is sitting right in front of you?In this episode, Jon Orr unpacks a simple but powerful question every business owner and investor needs to ask: are the inputs required to reach a goal actually worth the output? Through stories about kite surfing, marathon running, poker, and portfolio management, he explores how easy it is to confuse “I could do this” with “I should do this.”For entrepreneurs especially, the real tension is often between actively growing the business and spending countless hours trying to optimize passive investments. Sometimes the smartest move is not doing more—it is choosing where your time creates the greatest return.You'll walk away with:A clearer way to evaluate whether a goal is worth the time, energy, and commitment it requires.A practical lens for deciding whether your “alpha” comes from your investment portfolio or your active business.Permission to let passive assets stay passive so you can focus on the areas where your effort creates the biggest payoff.Press play now to rethink where your time is going—and whether the trade-off is truly worth it.
My guest today is Brian Chesky, the co-founder and CEO of Airbnb. Our conversation traces the path from his early training as an industrial designer at RISD through the pandemic moment that forced him into founder mode. He explains why he thinks AI founder mode will demand even more attention to the details and why founders are rarely good early CEOs. He walks through his eleven-star exercise, which is a way of imagining the most absurd version of a customer experience to achieve product market fit. We also talk about what changed for him when he stopped chasing adulation and started making things for the love of making them. 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. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to vanta.com/invest. ----- WorkOS is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- 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 (00:02:29) Episode Intro: Brian Chesky (00:03:07) Studying Industrial Design at RISD (00:08:30) Why Founders Don't Make Good CEOs (00:09:02) Founder Mode (00:12:51) AI Founder Mode (00:14:41) The End of Pure People Managers (00:18:42) Consumer AI (00:21:45) Project Hawaii (00:25:49) Make the Problem as Small as Possible (00:29:46) Becoming a Good CEO (00:32:11) What Brian Learned From Hiroki Asai (00:36:32) The Eleven-Star Experience (00:38:48) AI and Creativity (00:41:44) Making Things for the Love of It (00:43:36) The Adulation Trap (00:46:38) The Ham Sandwich Paradox (00:52:38) Why Founder-Led Businesses Endure (00:55:14) The Person as the Atomic Unit of Airbnb (00:59:40) Disrupting Yourself With AI (01:02:11) Lessons from Bodybuilding (01:07:55) Hiring as the Most Important Job (01:09:16) Are Founders Born or Made? (01:11:04) The Motivation of an Artist (01:11:47) The Kindest Thing
You've seen the ads. Invest like the ultra-wealthy. Get access to what the 1% does. But what does the 1% actually do -- and how much of it should a normal person try to copy? Joe, OG, comedian and finance educator Roxanne Duckels, and Jesse Cramer run every popular "rich people investing" idea through a simple filter: steal it, scale it, or skip it. The answers will surprise you -- especially the one where OG wants to delete an entire asset class from existence.What You'll Walk Away WithWhy long-term thinking is the one habit the 1% has that every Stacker should steal immediately -- and the short-term execution piece most people miss when they tryThe tax strategy obsession that the wealthy genuinely use -- and why Jesse ranks it seventh on his list of financial priorities, not firstWhat paying for advice actually means when you're smart enough to do it yourself -- and why the wealthiest people surround themselves with even smarter people anywayThe alternative investment marketing trap hiding inside every "invest like the rich" pitch -- and OG's case for why most people have no business touching any of itWhy the accredited investor designation protects almost no one -- and what the real risk is when you lock up money in illiquid investments chasing slightly better returnsThe leverage conversation that exposes a contradiction hiding in plain sight for every real estate investorWhy Roxanne's path to financial independence started with filling her gas tank all the way up -- and what that tells you about long-term thinking at any income levelThe one question that should precede any alternative investment conversation: does the expected return actually beat what publicly traded equities already offer?What the trivia competition scoreboard looks like heading into the back half of the year -- and whether OG's historic lead is as safe as it looksWhy rich habits and "what the 1% does" are two completely different things -- and which one is actually worth chasingWhy This Matters NowIn a noisy market environment, the "invest like the wealthy" pitch gets louder every time volatility spikes. Private credit, non-traded REITs, leveraged real estate, alternative assets -- the marketing machine never stops. For Stackers in their 40s who've built something real and don't want to blow it chasing a category that mostly benefits the people selling it, this episode is a useful reset. The habits worth stealing from the 1% turn out to be remarkably unglamorous.From the BasementJoe, OG, Roxanne Duckels from Finance Rox, and Jesse Cramer run the "invest like the rich" playbook through a steal-it-scale-it-skip-it framework -- and nobody agrees on everything, which is exactly what makes it useful. Doug arrives with Mayday trivia about the origin of the distress call and the year it was coined, which turns into one of the cleaner trivia finishes of the season. Whether the basement scoreboard moved in OG's favor or Jesse closed the gap is a question best answered with your earbuds in.Resources MentionedFinance Rox -- Roxanne Duckels on YouTube and Instagram @FinanceROXPersonal Finance for Long-Term Investors -- Jesse Cramer's podcast, wherever you listenStacking Benjamins Newsletter (The 201) -- recent issue: brokerage vs. UTMA/UGMA vs. Trump accounts for kids; stackingbenjamins.com/201Stacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Community -- stackingbenjamins.com/basementStacking Benjamins Meetups -- stackingbenjamins.com/badSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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 your investment results have less to do with what you own—and more to do with who you become when markets get uncomfortable?Most investors are taught to focus on picking the right stocks, funds, timing, or asset mix. But the real difference-maker is often behavior: how you react to uncertainty, losses, control, and fear. In this episode, you'll explore why two people can hold the same portfolio and still end up with very different outcomes—because their investor personality shapes the decisions they make along the way.You'll walk away with:A clearer understanding of the five investor personality types: the set-it-and-forget-it optimizer, skeptical controller, emotional reactor, confident operator, and security seeker.Insight into how loss aversion, overconfidence, and the urge for certainty can quietly influence your financial decisions.A better way to think about building an investment strategy that fits your real behavior—not just your risk questionnaire score.Press play now to discover which investor personality patterns show up in your financial life—and how to build a strategy you can actually stick with.
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 Paul Tudor Jones. Paul is the founder of Tudor Investment Corporation and one of the greatest macro traders of all time, known for calling and profiting from the 1987 crash and compounding capital at extraordinary rates over more than four decades. Paul is also one of the most entertaining and interesting people I have ever met. He is full of stories and hard-earned lessons from a lifetime in markets that feels like several lifetimes compressed into one. In this conversation, he shares how he thinks about trading as a constant battle of risk management and patience, why he still wakes up in the middle of the night to watch global markets, and how he identifies the rare moments where he can take a truly big swing. We discuss whether we are in a bubble, why he sees AI as one of the greatest risks in history, and why he believes Bitcoin is the best inflation hedge. We also spend time on the difference between trading and investing, the importance of passion and discipline, and the ideas that have shaped his life both inside and outside of markets. Please enjoy this conversation with Paul Tudor Jones. This conversation was recorded in mid-February 20, 26 weeks before the geopolitical conflicts now shaping the global economy. Please enjoy this great conversation with Paul Tudor Jones. 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. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to vanta.com/invest. ----- WorkOS is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- 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 (00:02:29) Episode Intro: Paul Tudor Jones (00:04:44) Paul's Incredible Kindest Thing Story (00:06:50) Discovering a Passion for Philanthropy (00:13:12) Paul's Commencement Speech Address (00:15:24) Trading v. Investing (00:19:23) Lessons from Warren Buffet (00:23:48) The AI Industry Lacks Proper Risk Management (00:26:54) The One Regulation AI Needs (00:28:51) What Paul Learned from Eli Tullis (00:30:39) Why Trading is Like Boxing (00:32:16) The Bull Case for the Yen (00:34:30) Why Bitcoin is the Best Inflation Hedge (00:36:06) Lessons from Historical Bubbles (00:38:57) Are We in a Bubble? (00:42:10) Paul's Daily Routine (00:44:12) Managing Information Overload (00:45:35) What Exquisite Execution Means (00:46:37) Paul's Love of Games (00:48:13) The Secret to Longevity (00:50:51) Starting Robin Hood After the 1987 Crash (00:55:33) The Importance of Studying Journalism (00:57:12) Communicating Effectively in Today's World (00:59:13) The Four Components of a Great Life (01:01:10) Paul's Relationship with God and Nature (01:03:53) Kill ‘Em With Kindness
The Last Trade: Jackson, Michael, and Brian break down PTJ's bitcoin conviction, equities at 252% of GDP, TradFi's gold underweight, Sztorc's "eCash" fork, the Strategic Bitcoin Reserve tease, & why custody governance rights matter.---
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 your retirement plan depends on selling the very assets you spent decades building?For many business owners and high-net-worth Canadians, “financial freedom” often means reaching a number on paper—but what happens when that number has to be slowly drawn down to fund your lifestyle? This episode challenges the traditional retirement mindset of accumulating a pile of assets, then hoping it lasts long enough. Instead, Jon Orr and Kyle Pearce explore how to think about income, diversification, and portfolio structure in a way that can support more confidence, flexibility, and peace of mind in your financial freedom years.You'll walk away with:A clearer understanding of why relying only on asset sales can feel emotionally risky when funding retirement.A fresh way to think about diversifying not just by asset class, but by strategy and structure for retirement.Insight into how income-focused investing can help create cash flow without constantly shrinking your principal when designing retirement.Press play now to rethink how your portfolio could support your lifestyle without forcing you to sell off the assets you worked so hard to build.
My guest today is Paul Tudor Jones. Paul is the founder of Tudor Investment Corporation and one of the greatest macro traders of all time, known for calling and profiting from the 1987 crash and compounding capital at extraordinary rates over more than four decades. Paul is also one of the most entertaining and interesting people I have ever met. He is full of stories and hard-earned lessons from a lifetime in markets that feels like several lifetimes compressed into one. In this conversation, he shares how he thinks about trading as a constant battle of risk management and patience, why he still wakes up in the middle of the night to watch global markets, and how he identifies the rare moments where he can take a truly big swing. We discuss whether we are in a bubble, why he sees AI as one of the greatest risks in history, and why he believes Bitcoin is the best inflation hedge. We also spend time on the difference between trading and investing, the importance of passion and discipline, and the ideas that have shaped his life both inside and outside of markets. Please enjoy this conversation with Paul Tudor Jones. This conversation was recorded in mid-February 20, 26 weeks before the geopolitical conflicts now shaping the global economy. Please enjoy this great conversation with Paul Tudor Jones. 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. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to vanta.com/invest. ----- WorkOS is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- 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 (00:02:29) Episode Intro: Paul Tudor Jones (00:04:44) Paul's Incredible Kindest Thing Story (00:06:50) Discovering a Passion for Philanthropy (00:13:12) Paul's Commencement Speech Address (00:15:24) Trading v. Investing (00:19:23) Lessons from Warren Buffet (00:23:48) The AI Industry Lacks Proper Risk Management (00:26:54) The One Regulation AI Needs (00:28:51) What Paul Learned from Eli Tullis (00:30:39) Why Trading is Like Boxing (00:32:16) The Bull Case for the Yen (00:34:30) Why Bitcoin is the Best Inflation Hedge (00:36:06) Lessons from Historical Bubbles (00:38:57) Are We in a Bubble? (00:42:10) Paul's Daily Routine (00:44:12) Managing Information Overload (00:45:35) What Exquisite Execution Means (00:46:37) Paul's Love of Games (00:48:13) The Secret to Longevity (00:50:51) Starting Robin Hood After the 1987 Crash (00:55:33) The Importance of Studying Journalism (00:57:12) Communicating Effectively in Today's World (00:59:13) The Four Components of a Great Life (01:01:10) Paul's Relationship with God and Nature (01:03:53) Kill ‘Em With Kindness
Invest Like a Billionaire - The alternative investments & strategies billionaires use to grow wealth
Most investors think picking the right deal is how you win. It's not.In this episode of Invest Like a Billionaire, we break down why investing deal by deal can quietly destroy your returns and what actually builds long-term wealth.We cover:Why “good” deals still lose money over timeThe IRR trap most investors fall intoHow cash drag and taxes kill compoundingWhy wealthy investors focus on consistency, not home runsIf you're investing in real estate or private markets, this will change how you think about building wealth.Have more questions, or want more resources like a tax calculator? Go to https://investlikeabillionaire.org/ to learn more about our community. Check out Ben & Bob's company and invest along at https://aspenfunds.us/
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 happens if your main income engine slows down before your backup plan is even moving?If you're building a business, growing retained earnings, or counting on a future exit to fund your freedom, this episode is a timely reality check. Jon Orr and Kyle Pearce unpack why so many Canadian entrepreneurs pour everything into one flywheel—the business or job that funds life today—while neglecting the second flywheel that's supposed to protect them later. This conversation speaks directly to anyone who wants more stability, more options, and less financial stress when business gets unpredictable.In this episode, you'll hear how to:think about wealth in terms of two flywheels: your active income engine and your passive income enginestop relying on a future business sale as the only path to long-term freedomstart building a second flywheel early by allocating profits strategically between safe, liquid assets and longer-term growth assetsPress play now to learn how to build financial momentum that keeps working, even when your first flywheel hits turbulence.
This is my second conversation with Dylan Patel. Dylan is the founder and CEO of SemiAnalysis, where he tracks the semiconductor supply chain and AI infrastructure buildout. This conversation is about the supply and demand of tokens. On demand, Dylan describes something completely explosive. He explains why the frontier model is the only model anyone wants, and willingness to pay for it is nearly unbounded. His own firm has gone from tens of thousands of dollars in AI spend last year to seven million this year. On supply, we walk through the bottlenecks across memory, logic, and fab equipment that will determine how fast any of this can scale. We also cover Claude Mythos and what the leading labs need to do to fix their growing public perception problem. 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 the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- 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 (00:02:29) Intro: Dylan Patel (00:03:09) Semi Analysis AI Spend: Zero to $7M (00:05:16) Real-World Examples of Claude Code (00:11:41) Token Demand: “Completely Explosive” (00:14:48) Why Everyone Wants the Frontier Model (00:15:36) Mythos: Biggest Model Capability Jump in Two Years (00:20:54) Fear of Rapid Model Progress (00:23:45) Robotics as the Next Demand Wave (00:26:03) Scaling Laws & Compute Efficiency (00:27:24) OpenAI vs. Anthropic (00:31:33) Supply Side: Bottlenecks Across the Stack (00:33:26) TSMC CapEx Could Cause a Shortage (00:36:45) CPUs, ASICs, and FPGAs (00:40:12) Tokenomics (00:42:20) Protests & AI Backlash
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 Alex Karnal. Alex is the co-founder and managing partner of Braidwell, a life sciences investment firm he built after spending 15 years at Deerfield Management. The frame we use throughout the episode is the health stack. Alex talks about how most of the diseases that will claim most of our lives are already addressable with medicines that exist today. We work through the five layers of what a defensive health strategy looks like, why GLP-1 medicines represent the first commercial proof that people are ready to be proactive about their health, and why PCSK9 inhibitors may ultimately be the more important drug class even though they get far less attention. We also get into the science and business of drug discovery itself — why most of the published literature that AI companies are training on cannot be replicated, what it would mean to have a truly agentic scientific lab running 24 hours a day, and why Alex believes we are now on a deterministic curve toward scientific superintelligence in biology. 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 (00:02:29) Intro: Alex Karnal (00:03:15) State of the Union: GLP1s and Life Sciences (00:07:01) The Health Stack Framework (00:12:49) Breaking Down the 5 Defensive Layers (00:21:18) GLP-1: What's Driving the Inflection (00:28:28) Diet vs. Drugs: Is Food Enough? (00:31:15) Barriers to Access: Complexity, Cost & Compliance (00:35:04) PCSK9: The Closest Thing to a Free Lunch (00:44:10) Alzheimer's & Neurodegenerative Disease (00:46:59) Cancer: Early Detection & New Treatments (00:54:49) Body Imaging & Diagnostic Trade-offs (00:56:31) How Drugs Are Discovered (01:02:39) AI in Drug Discovery (01:10:57) The Automated Lab of the Future (01:13:05) Peptides & Citizen Pharmacology (01:16:45) Alex's Background (01:28:25) Braidwell's Investment Approach (01:30:39) 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 hereWant to turn corporate retained earnings into future tax-efficient cash flow without locking your money away?If you are a business owner sitting on retained earnings, you have probably felt the tension between paying personal tax now or leaving money in the corporation and dealing with the tax consequences later. This episode walks through a strategy designed to create more flexibility: using a corporate-owned permanent life insurance policy as a pass-through structure that can support borrowing, asset growth, and long-term estate planning. It is especially relevant if you want more optionality with your money while keeping an eye on taxes, liquidity, and legacy.In this episode, you'll learn how to:Understand how a corporate-owned permanent life insurance policy can help reduce future personal tax friction on retained earnings.See what funding levels like $1 million per year versus $100,000 per year can actually look like in practice, including cash value growth, leverage potential, and policy offset options.Grasp how this structure can support both living benefits now and estate planning advantages later through growing cash value, borrowing flexibility, and tax-efficient death benefit planning.Press play now to see how this strategy can create more control, more flexibility, and a more tax-efficient path for your corporate wealth.
My guest today is Alex Karnal. Alex is the co-founder and managing partner of Braidwell, a life sciences investment firm he built after spending 15 years at Deerfield Management. The frame we use throughout the episode is the health stack. Alex talks about how most of the diseases that will claim most of our lives are already addressable with medicines that exist today. We work through the five layers of what a defensive health strategy looks like, why GLP-1 medicines represent the first commercial proof that people are ready to be proactive about their health, and why PCSK9 inhibitors may ultimately be the more important drug class even though they get far less attention. We also get into the science and business of drug discovery itself — why most of the published literature that AI companies are training on cannot be replicated, what it would mean to have a truly agentic scientific lab running 24 hours a day, and why Alex believes we are now on a deterministic curve toward scientific superintelligence in biology. 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 (00:02:29) Intro: Alex Karnal (00:03:15) State of the Union: GLP1s and Life Sciences (00:07:01) The Health Stack Framework (00:12:49) Breaking Down the 5 Defensive Layers (00:21:18) GLP-1: What's Driving the Inflection (00:28:28) Diet vs. Drugs: Is Food Enough? (00:31:15) Barriers to Access: Complexity, Cost & Compliance (00:35:04) PCSK9: The Closest Thing to a Free Lunch (00:44:10) Alzheimer's & Neurodegenerative Disease (00:46:59) Cancer: Early Detection & New Treatments (00:54:49) Body Imaging & Diagnostic Trade-offs (00:56:31) How Drugs Are Discovered (01:02:39) AI in Drug Discovery (01:10:57) The Automated Lab of the Future (01:13:05) Peptides & Citizen Pharmacology (01:16:45) Alex's Background (01:28:25) Braidwell's Investment Approach (01:30:39) The Kindest Thing
Welcome to episode 327 of Grow Your Law Firm, hosted by Ken Hardison. In this episode, Ken sits down with Bob Fraser, CFO and Chief Macro Strategist at Aspen Funds. Bob is also the co-host of Invest Like a Billionaire, a podcast dedicated to educating investors on the power of private alternatives. Bob has a background in tech startups, a history of overcoming financial setbacks, and a passion for helping investors diversify their portfolios beyond traditional markets. The conversation delves into Bob's book Invest Like a Billionaire and explores the world of alternative investments. Bob shares how he transitioned from losing everything in the dot-com crash and the financial crisis to discovering private alternatives, which offer higher yields, less volatility, and unique investment opportunities. He explains why billionaires invest 50-60% of their wealth in private markets, and why average investors can benefit from similar strategies. Bob's insight provides a clear roadmap for law firm owners and high-income professionals looking to protect and grow their wealth in a volatile financial environment. What you'll learn in this episode: The Billionaire Investment Strategy - Why billionaires invest 50-60% of their wealth in private alternatives, not the stock market - How private investments offer superior returns with less volatility Understanding Alternative Investments - How private credit, real estate, and private equity differ from traditional stocks and bonds - Why private credit can provide higher yields and stable cash flow Why You Should Avoid DIY Investments - Why the DIY real estate or small business investment isn't part of the "alternative" world - The advantages of professionally managed, diversified private funds The Power of Diversification in Private Markets - How building a portfolio of uncorrelated assets can protect you from market volatility - Bob's "Billionaire Portfolio" strategy that balances risk with high returns The Role of Natural Resources in Your Portfolio - Why energy investments are a great hedge against inflation and market downturns - Why now is a generational opportunity in energy Resources: Website: aspenfunds.us LinkedIn: linkedin.com/in/bobfraser10/ Facebook: facebook.com/aspenfunds Additional Resources: https://www.pilmma.org/the-mastermind-effect https://www.pilmma.org/resources https://www.pilmma.org/mastermind https://www.pilmma.org/events/super-summit DISCOUNT CODE: 26SSGROW
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 would it actually take to make work optional by age 50?As a Canadian business owner or investor, If you have a good income, some investments, and a rough number in mind for “financial freedom,” it is easy to assume you are on the right track to financial freedom without ever testing the math. But there is a big difference between a financial goal that sounds safe and a goal that truly fits the life you want. This episode helps you cut through the guesswork so you can stop chasing arbitrary numbers and start building a financial plan that matches your timeline, spending, and priorities.In this episode, you'll learn how to:figure out whether your financial freedom number actually covers the lifestyle you want in the futurereverse-engineer your financial target based on spending, inflation, rate of return, and time horizonseparate your minimum financial goal from your stretch goal so you can grow wealth without losing sight of what matters mostPress play now to build a clearer, more realistic path toward financial freedom without sacrificing the life you want along the way.
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 hereWant a smarter way to use corporate retained earnings without triggering a massive personal tax hit?If you're a successful incorporated business owner in Canada, you've probably felt the tension between leaving profits trapped in the corporation or pulling them out and losing a huge chunk to tax. This episode explores a different path: using a permanent insurance policy as a strategic pass-through structure so your money can keep working, give you more flexibility, and support both current cash-flow goals and long-term planning.In this episode, you'll learn how to:Turn retained earnings into a tax-efficient asset that can grow inside your corporate structure instead of sitting in taxable passive investments.Create a strategy where the same dollars can support future investing opportunities through leverage, helping your money work in more than one place at once.Build in long-term upside through tax-free death benefit planning and greater flexibility for personal cash flow, estate planning, and eventual extraction strategies.Press play to hear how this corporate strategy can help you keep more of what you've built while expanding your options for the future.
Scott Nolan spent 12 years at Founders Fund looking for the most important problems that no one else was funding. Then he found a problem so critical, and so ignored, that he couldn't find a company to back. So he started one. General Matter is rebuilding US uranium enrichment. The United States was the world leader in enrichment through the 1980s and then stopped entirely. Today roughly a quarter of US enriched uranium comes from Russia, a ban on those imports takes full effect in 2028, and the advanced reactors everyone is counting on to power the next wave of data centers have no reliable domestic fuel source. Scott believes enrichment is the single bottleneck to a nuclear future, and that the window to solve it is narrow. The conversation covers how Peter Thiel influenced him, why being in love with an idea is dangerous for investors but required for founders, and what it actually takes to rebuild an industrial capability the country let atrophy for 40 years. Please enjoy my conversation with Scott Nolan. 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 (00:02:45) Guest Intro: Scott Nolan (00:03:36) SpaceX, Founders Fund & General Matter (00:08:04) What Scott learned from Peter Thiel (00:10:05) The "Avoid Trends" Concept (00:10:55) Finding Important Problems No One Is Working On (00:17:32) Gut v. Intuition (00:18:49) Valuation, Competition & Capital Intensity (00:20:20) Founders Fund Strategy (00:21:06) The Steeper the Up Round, the Greater the Undervaluation (00:21:41) Being in Love with the Problem (00:26:07) Governments, Technology & History (00:28:54) Lessons from SpaceX and Elon (00:29:42) Vertical Integration (00:33:07) The Role of Energy in Civilization (00:37:36) State & Direction of US Energy (00:38:58) Why Nuclear? (00:42:20) Taxonomy of Advanced Reactors (00:45:33) The BYOE Concept (00:46:50) What Could Make Advanced Reactors Fail? (00:48:04) General Matter: Product, Business & Company (00:50:12) Enrichment & Weapons-Grade Uranium (00:56:45) North Star Metric (01:01:05) Building a Great Enduring Company (01:04:01) How Scott Runs the Company (01:06:11) Overcoming Irrational Fears About Nuclear (01:08:25) Why Aren't There More Founders Funds? (01:10:03) Operating vs. Investing (01:11:56) Kindest Thing
#342: In this week's episode of She's So Lucky, we're continuing our Lucky Girls Invest series with a guest who defines what it means to build power, wealth, and legacy — Emma Grede.This is one of those conversations.The kind that recalibrates how you think about money, ambition, and what it actually takes to create the life you say you want.In this episode, I sit down with Emma for an unfiltered, deeply tactical conversation on what it means to invest. Not just in the market, but in yourself, your relationships, and your long-term vision. From her early days growing up in East London to building and scaling multi-billion-dollar companies, Emma breaks down the real decisions, trade-offs, and mindset shifts that got her here.We talk about the difference between being in proximity to power and actually having it. Why so many people are distracted by visibility instead of focusing on what truly moves the needle. And how learning to think like an investor – before you ever write a check – can completely change the trajectory of your life.This episode is packed with gems and never-before-told stories from Emma, it's the kind of insight you only get from someone who has actually done the work, built the businesses, and made the money.If you're serious about building wealth, stepping into your ambition, and operating at a higher level… this one is required listening.This episode is for you if:You're ready to move differently when it comes to money, power, and decision-making — and start thinking like an investor in your own lifeYou've been caught up in visibility, networking, or “being in the room” and are ready to refocus on what actually moves the needle.You're learning how to prioritize yourself, your vision, and your goals without guilt or second-guessing.You want to shift from asking “how do I get in the room?” to becoming the person who owns the room.You're navigating your relationship with money from scarcity, to stability, to building real wealth.You want to understand why profit matters more than perceptionYou're building (or want to build) something of your own and need clarity on what actually makes a business… a business.You're ready to invest in the relationships that matter and stop overextending yourself in one-sided dynamics.You need the reminder that ambition requires discomfort and that choosing yourself is the work.Episode Links:Get Emma's new book, Start With Yourself, and take what you learn here one step further.Visit Emma's website, https://www.emmagrede.com/, for more.Follow Emma on Instagram: https://www.instagram.com/emmagredeListen to Aspire With Emma Grede link.pscrb.fm/f0281/Aspire_YTSponsors:Nutrafol: For a limited time, Nutrafol is offering our listeners $10 off your first month's subscription and free shipping when you visit Nutrafol.com and enter promo code BALANCEDLESMonarch Money: Use code LUCKY at monarch.com to get your first year half off at just $50.No Bull: Exclusively for She's So Lucky listeners, NOBULL is offering 35% off your FIRST order. Visit www.nobullproject.com and use code DMLUCKY for 35% off your entire FIRST orderConnect with Les:Ready to apply what you hear? Subscribe to the She's So Lucky Newsletter to get weekly episode guides and journal prompts: https://shessolucky.kit.com/newsletterSubscribe to The Lucky Playbook on Substack: https://lesalfred.substack.com/Follow Les on IG @lesalfredFollow She's So Lucky on IG @shessoluckypodFollow Les on TikTok @theluckylesFollow She's So Lucky on TikTokVisit our website at shessoluckypodcast.comThis episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.Produced by Dear MediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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 spending too much time trying to optimize your money instead of making the moves that actually build wealth?This episode is for the Canadian business owner who wants to be smarter with taxes, investing, and long-term planning—but also knows how easy it is to get stuck in analysis. Hosts, Jon Orr and Kyle Pearce unpack a powerful mindset shift for the year ahead: stop chasing every tiny optimization and focus on the habits and decisions that create real momentum. If you have ever wondered whether your financial strategy is actually helping—or just distracting you—this conversation will hit home.You'll hear how to create one simple, repeatable money habit that can quietly build wealth over time.You'll learn why increasing income and protecting your focus can matter more than endlessly tweaking tax and investment decisions.You'll also get a practical lens for deciding when to keep managing things yourself and when it may be smarter to systematize or delegate.Press play now to reset your financial focus for the next year and make the moves that matter most.
My guest today is Alan Waxman, co-founder and CEO of Sixth Street, a $130B global investment firm. Private credit is one of the most discussed topics in markets right now, and there is a lot to make sense of. The current discourse is almost entirely focused on symptoms. Alan Waxman has spent the time diagnosing the root cause. Alan thinks about the financial system the way a historian would, studying the incentives, guardrails, and market structure that determine how things play out. In this conversation, he traces the evolution of American finance from the 1929 crash through Glass-Steagall, the GFC, and Basel III to explain how we arrived at what he calls the factory model, the industrialization of liability-gathering and asset deployment that he believes is the root cause of everything happening in private markets today. This is my second conversation with Alan, our first one is one of my favorites from last year. 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 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. ----- 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. ----- 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) Intro: Alan Waxman (00:04:35) Financial System Guardrails & Incentives (00:05:56) System 1: Pre-1933 to 1999 (00:07:39) Glass-Steagall Legislation (00:10:46) Deregulation & Rise of System 2 (00:12:27) Leverage, GFC, and System 2's Collapse (00:14:25) Basel III, Dodd-Frank, and System 3 (00:15:32) Why System 3 Could Be the Best Ever (00:19:04) Behavioral Shifts Starting in 2018 (00:19:52) The Factory Model (00:24:33) Acceleration of Factory Model (00:28:25) FRE Multiples and GP Incentives (00:34:59) Wealth Channel & Asset-Liability Mismatches (00:36:15) Why This Won't be the Next GFC (00:45:31) AI, Creative Destruction & Opportunity (00:49:35) Alan's One-Sheet Brain System (00:55:01) Lessons by Decade: Hui (00:59:28) Face the Tiger
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 a business you can actually step away from—or just creating a job that depends on you forever?If you're a Canadian incorporated business owner thinking about retirement, succession, or a possible exit, this episode digs into the messy middle most people face. What happens when your business creates strong income, but only because you are still carrying so much of the load? You'll hear a real-world discussion about how to start shifting from being the engine of the business to building something more sustainable, valuable, and flexible for your next chapter.In this episode, you'll learn how to:think more clearly about whether your best move is to sell, stay, or gradually step backincrease the value of a business by making it less owner-dependent and more self-sustainingexplore practical transition options like hiring the right operator, profit sharing, and phased ownership over timePress play to hear a smarter way to prepare your business for freedom, flexibility, and a more confident exit.
In this episode, Michael sits down with Bob Fraser, CFO and Chief Macro Strategist at Aspen Funds and author of Invest Like a Billionaire. Bob shares why billionaires invest very differently than most people—and why relying solely on stocks and bonds may be limiting your ability to build long-term wealth.The conversation explores alternative investments like multifamily, private credit, industrial real estate, oil and gas, and private equity. Bob explains how to think through market cycles, why diversification across uncorrelated assets matters, and how investors can position themselves to benefit from long-term tailwinds instead of chasing the latest trend.Key TakeawaysBillionaires don't rely on a traditional 60/40 portfolio—they allocate heavily to alternative investments and uncorrelated assets. There is always an asset class that is working, even when another is struggling, which is why diversification across market cycles matters. Private credit can provide equity-like returns with lower risk by acting as the lender instead of the owner. Investors should focus on long-term macro tailwinds like reshoring, industrial real estate, and energy demand rather than chasing short-term narratives.Great operators are defined by how they perform during difficult market cycles, not just during boom years.You don't need to master every asset class yourself—joint ventures and partnerships can help you gain exposure to new opportunities. Connect with MichaelFacebookInstagramYouTubeTikTokResourcesTheFreedomPodcast.com Access the #1 FREE Apartment Investing Course (Apartments 101)Schedule a Free Strategy Session with Michael's Team of AdvisorsExplore Michael's Mentoring ProgramJoin the Nighthawk Equity Investor ClubReview the Podcast on Apple PodcastsSyndicated Deal AnalyzerGet the Book, Financial Freedom with Real Estate Investing by Michael Blank For full episode show notes visit: https://themichaelblank.com/podcasts/session518/
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 paying 1% for investment management a waste of money—or the exact support that could protect your wealth?If you've ever wondered whether you should keep investing on your own or hand the reins to an advisor, this episode gets right to the heart of that tension. It speaks to the very real struggle between wanting to minimize fees and wanting more confidence, better decision-making, and less stress when markets get shaky. Whether you're early in your investing journey or getting closer to financial freedom, this conversation helps you think beyond simple math and make a choice that actually fits how you operate.You'll walk away with:A clearer way to decide whether DIY investing or professional management fits your personality, habits, and goalsA better understanding of what you're really paying for with a 1% fee, including coaching, accountability, peace of mind, and complexity managementA practical lens for comparing options using time, behavior, and risk-adjusted returns—not just headline performance numbersPress play now to figure out whether paying for investment management is costing you too much—or saving you from bigger mistakes.
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 do you do when you've built more wealth than you need—but your success is quietly setting up a massive future tax bill?This episode walks through a real planning scenario that will hit home for many Canadian business owners, entrepreneurs, and investors. You'll hear how one retired entrepreneur did almost everything right—paid off the house, built strong investment buckets, and created lasting financial security—yet still ended up with hidden tax inefficiencies inside a RRIF, personal accounts, and a holding company. If you've ever wondered whether your current structure could create unnecessary drag later, this conversation shows where those problems come from and what can still be done to improve them.You'll learn:How large RRIF balances can create a growing tax problem in retirement, even when you do not need the income.Why asset location matters—especially when comparing TFSAs, non-registered GICs, and corporate investments.How strategies like leveraged investing and corporate-owned whole life insurance may help reduce tax drag, improve estate efficiency, and create more flexibility for future withdrawals.Press play to hear how a “good problem to have” can become a smarter, more tax-efficient wealth plan. Built from your uploaded transcript.
My guest today is Sergey Levine, a professor at UC Berkeley and co-founder of Physical Intelligence. The company is building robotic foundation models designed to control any embodied system to do any task in any environment. Sergey argues that solving robotics at full generality is the right path, and that building systems that learn across many robots, environments, and tasks may be the more scalable approach than building narrow specialists. We discuss how these models can perform new tasks without being trained on them directly, and why everyday human actions remain the hardest problems in the field. He also reflects on how human trust and acceptance may matter as much as technical breakthroughs in determining when robots become part of daily life. Please enjoy my conversation with Sergey Levine. 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: Sergey Levine (00:03:29) Why Bet on Generality Over Specialization (00:07:24) What if PI succeeds? (00:09:05) Pros and Cons of Humanoid Robotics (00:11:02) Timeline of Major Milestones in Robotics (00:15:47) Sergey's Personal Journey (00:18:22) Making General Intelligence Happen (00:19:57) Understanding Robot Data Collection (00:22:12) Most Surprising Discovery at Physical Intelligence (00:24:48) The Science of Common Sense (00:25:36) Long-Range Tasks in Robotics (00:27:24) Why Wouldn't We Have A Robot in Our Kitchen by 2050 (00:31:21) Other Interesting Approaches (00:32:38) Cool vs. Useful in Robotics (00:36:48) Form Factor Innovation (00:38:22) Physical Intelligence Analogy (00:39:30) Economic Transformation from Robotics (00:40:48) Controversies in the Robotics Community (00:42:16) Arguments Against End-to-End Learning (00:42:34) Compositional Learning Explained (00:43:25) Last Tasks Robots will Conquer (00:44:30) Dark Parts of the Robotics Brain (00:47:05) What Makes a Great Researcher (00:50:15) Manufacturing and Scale Challenges (00:51:17) How Companies Should Prepare for Robotics (00:53:38) Boston Dynamics' Demos (00:55:43) Converging Technologies Enabling Robotics (00:56:47) How to Stay Up To Date in Robotics (00:59:51) Near Term Objectives (01:00:49) Confidence Level Among Researchers (01:03:31) Google's Experimentation Culture (01:04:24) The Kindest Thing
My guest today is Mitchell Green. Mitchell Green is the co-founder and managing partner of Lead Edge Capital, a growth equity firm that has spent 15 years building one of the most disciplined investment machines in the business. Unlike most firms chasing power law outcomes, Lead Edge is designed to deliver consistent returns by talking to thousands of companies a year, applying a rigorous eight-point criteria to filter down to a handful of investments, and leveraging a uniquely constructed LP base of world-class executives and entrepreneurs. In this conversation, Mitchell walks through every component of the machine, from how they source and evaluate companies to how they think about selling, building culture, and staying competitive in a world being reshaped by AI. 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 (00:00:53) Episode Intro: Mitchell Green (00:02:01) Cold Calling 10,000 Companies (00:03:54) Building the Lead Edge Machine (00:06:15) Lead Edge's LP Profile (00:09:22) Hitting Doubles and Triples (00:11:39) Knowing When to Sell (00:15:08) Lead Edge's Eight Buying Criteria (00:18:12) The Opportunity in Enterprise Software (00:24:54) Using Criteria for Filtering, Not Prediction (00:27:11) Building Relationships with Entrepreneurs (00:29:16) Improving the Investment Machine at Scale (00:31:59) Lead Edge's Culture (00:35:08) Mitchell's Schedule (00:36:37) The Mount Rushmore of Investment Machines (00:38:40) The AI Readiness Score (00:40:50) Overhyped, Frothy Markets (00:42:16 When AI Will be a Good Opportunity (00:44:29) Lessons from Competitive Skiing (00:47:33) Starting a Fund & Keeping Score (00:49:15) The Kindest Thing
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
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
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
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
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