Founders & Friends

What if Wall Street is overlooking some of the market’s biggest investment opportunities?In this episode of Founders and Friends, Michael Monaghan sits down with Erin Gibbs, Chief Equity Strategist at SlateStone Wealth, with more than 25 years of Wall Street experience to discuss why small- and mid-cap stocks may offer compelling opportunities beyond the mega-cap technology giants.Erin explains why investors may be more concentrated in the S&P 500’s largest companies than they realize, where she sees opportunities emerging from the AI infrastructure boom, and why disciplined investing sometimes means going against the crowd.Drawing on her experience at Sanford Bernstein, Citi, and S&P Capital IQ, Erin shares how quantitative models, financial fundamentals, and market sentiment shape her investment decisions, including the story of how one of Wall Street’s most hated stocks became one of her biggest winners.In this conversation:* Why Wall Street may be overlooking small- and mid-cap stocks* The hidden concentration risk in S&P 500 portfolios* Finding AI investment opportunities beyond NVIDIA and Meta* Why mid-caps could benefit from attractive valuations and earnings growth* How quantitative models help remove emotion from investing* What investors can learn from contrarian investment decisions* Why AI tools aren’t always reliable for financial research* How to evaluate stocks, manage risk, and know when to sell* Three principles for becoming a more disciplined investorWhether you’re just getting started or looking to sharpen your investment strategy, this conversation offers a perspective on finding opportunities beyond the crowd.⏱️ Chapters00:00 Highlights00:59 Meet Erin Gibbs: 25 Years on Wall Street02:45 Lessons From 25 Years of Investing04:16 From Quant Analyst to Portfolio Manager05:52 Why Wall Street Is Overlooking Mid-Cap Stocks08:14 The Jan Brady of Investing: Why Mid-Caps Matter10:00 The Hidden Concentration Risk in the S&P 50011:28 Beyond NVIDIA: Finding the Next AI Beneficiaries13:00 Investing Advice: What Beginners Should Know16:41 Quant Models vs. Human Judgment19:55 Backtesting, Bias, and Investment Discipline22:00 Stock Selection, Market Sentiment, and When to Sell25:00 Why AI Gets Financial Research Wrong26:38 Inflation, Oil Prices, and Recession Risks28:29 Why Erin Gibbs Joined SlateStone Wealth30:25 Three Rules for Becoming a Better InvestorAbout Founders and FriendsHosted by Michael Monaghan, Founders and Friends features conversations with leading investors, market strategists, entrepreneurs, and financial thinkers about investing, markets, business, and the ideas shaping the future.Subscribe for more conversations on investing, financial markets, and the people shaping them.Connect with Erin Gibbs:SlateStone Wealth: https://slatestone.com

Anthony Scaramucci joins Michael Monaghan for a wide-ranging conversation on Wall Street, the American worker, inflation, China, AI, Bitcoin, the 2008 financial crisis, politics, entrepreneurship, and what America can do next.Scaramucci, founder of SkyBridge Capital and the SALT Conference, reflects on the economic decisions he believes helped Wall Street prosper while many working-class Americans were left behind. He explains what he learned from traveling across the country, why inflation can act like a hidden tax on workers, how globalization changed American jobs, and why artificial intelligence could reshape the balance between capital and labor.The conversation also gets personal. Anthony talks about the investments he regrets selling, initially passing on Bitcoin, learning from younger generations, pivoting SkyBridge toward digital assets, surviving failure and public setbacks, and why founders need the ability to adapt when the world changes.Michael and Anthony also discuss the national debt, infrastructure spending, the 2008 bank bailout, healthcare and education, political incentives, defense spending, entrepreneurship, optimism, and Anthony’s idea of “pronoia” — the opposite of paranoia.Anthony Scaramucci is the founder and managing partner of SkyBridge Capital, founder of SALT, former Goldman Sachs vice president, author, entrepreneur, and former White House Communications Director.His latest book, All the Wrong Moves, examines the decisions that helped shape America’s current economic and political environment and what can be learned from them.If you enjoyed the conversation, subscribe to Founder & Friends for long-form discussions with investors, founders, CEOs, and market thinkers.Anthony Scaramucci, SkyBridge Capital, SALT Conference, Wall Street, American economy, working class, inflation, AI jobs, artificial intelligence, Bitcoin, China, globalization, national debt, 2008 financial crisis, investing, founders, entrepreneurship, Donald Trump, politics, optimism, pronoia.#AnthonyScaramucci #WallStreet #InvestingChapters00:00 Why success can create blind spots00:32 Meet Anthony Scaramucci01:10 The biggest investing lesson from 30 years02:27 Founder anxiety and resetting your brain04:52 Money anxiety, family, and success05:45 What America got wrong for workers07:04 China, globalization, and American jobs09:30 AI, automation, and a world of abundance10:55 Infrastructure vs. war spending13:04 Inflation: the hidden tax on workers16:27 Inequality, empathy, and anger-based populism17:52 How Scaramucci would tackle the deficit19:49 AI job displacement and capital vs. labor23:45 Healthcare, education, and equal opportunity25:52 Why American food and healthcare cost so much28:12 Is there really a left and right anymore?28:38 What Washington taught Anthony Scaramucci31:11 Why politics lacks market-style accountability32:23 War, drones, and the economics of defense35:36 What went wrong with the 2008 bailout37:42 Bitcoin and learning from younger people40:16 Why founders have to survive failure42:50 Pivoting SkyBridge into digital assets43:23 How founders make impossible decisions44:41 Hollywood, reinvention, and following your interests46:41 “My best days are ahead of me”47:31 Pronoia: the opposite of paranoia49:12 All the Wrong Moves + signed book giveaway

The next wave of IPOs could include some of the biggest technology companies in the world. But how do you actually buy an IPO without getting caught up in the hype?Jeff Bernstein spent years at Goldman Sachs working on technology IPOs before moving to the buy side and running money at Galleon and his own hedge fund. He joins Michael Monaghan to explain what actually happens behind the scenes before a company goes public, how IPO prices are set, why an offering can be “25x oversubscribed” without all of that demand being real, and how retail investors should think about buying after the opening print.They also discuss Anthropic, SpaceX, founder-led companies versus private equity-backed IPOs, what separates generational companies from the rest, lessons from the dot-com era, and why patience may be one of the biggest advantages an investor has when buying a newly public company.Jeff also shares stories from Goldman Sachs, Galleon, the late-1990s technology boom, Red Hat, Siebel Systems, and what decades around technology companies taught him about founders, markets and investor trust.Chapters00:00 Which IPO Would Jeff Buy?00:40 Meet Jeff Bernstein01:18 Why Companies Are Going Public Again04:08 Great Founders Treat Their Stock Like a Product05:48 Founder-Led vs Private Equity IPOs06:37 How an IPO Price Is Actually Set09:47 Why “25x Oversubscribed” Can Be Misleading10:08 How Big Institutions Place IPO Orders11:48 Preparing a Company for an IPO13:18 Who Actually Gets IPO Allocations?17:07 How SpaceX Changed the IPO Pricing Playbook18:57 The Danger of Aggressive Forecasts21:02 Inside the SpaceX Opening Print23:07 Why Retail Investors Matter More Now24:14 Bookings vs Real Revenue26:07 How Retail Investors Should Buy IPOs27:28 Why Great IPOs Often Come Back Down28:09 Michael’s “Public Venture” Framework29:26 How to Spot a Generational Company30:42 Anthropic, OpenAI and the Next Big IPOs32:11 What Nvidia Teaches About Long-Term Moats33:46 Is Silicon Coming Back to Silicon Valley?35:28 Why Capital Intensity Can Be a Moat36:31 Today’s AI Boom vs the Dot-Com Bubble38:09 Red Hat and “Price Per PhD”40:00 What Tom Siebel Got Right41:09 Founders Who Know How to Build an Investor Base43:17 What Jeff Believes Differently Today44:22 When a SPAC Is the Wrong Choice45:45 Jeff’s Career From Goldman to Galleon50:46 Where to Find Jeff51:13 How to Approach the Next IPO Wave53:16 Final TakeawaysSubscribe to Founders & Friends for candid conversations with investors, market strategists, financial journalists, founders, and people shaping the markets.#ipo #anthropic #spacex #investing

Barry Ritholtz explains why getting rich through investing is simpler than most people think, why market forecasts are so often wrong, and why your own behavior may be the biggest threat to long-term investment success.Michael Monaghan sits down with Barry Ritholtz, Chairman and Chief Investment Officer of Ritholtz Wealth Management, host of Masters in Business, and author of How Not to Invest, for a wide-ranging conversation on stock market investing, compounding, index funds, active management, investor psychology, financial media, market predictions, and building wealth over time.Barry explains why investors should focus on getting rich slowly, why humans are psychologically wired to make poor decisions in volatile markets, and why the most confident market forecasts can often be the least reliable.They discuss why so few active managers outperform over long periods, what Barry learned from Warren Buffett, Ray Dalio, Howard Marks, and Daniel Kahneman, and why he believes most investors should keep the core of their portfolio simple.Barry also shares his “cowboy account” strategy for investors who still want to pick stocks, including how he thinks about Nvidia and speculative investments without putting long-term wealth at risk.The conversation also explores what financial advisors actually add beyond investment performance, direct indexing and tax-loss harvesting, and why Barry believes the purpose of money is not simply to accumulate a bigger number.Topics include:Stock market investingHow to build wealthLong-term investing and compoundingWhy market predictions failInvestor psychology and behavioral financeActive management vs index fundsS&P 500 and Vanguard investingNvidia and individual stock investingRay Dalio and learning from mistakesHoward Marks and second-level thinkingDaniel Kahneman and behavioral investingFinancial media and market noisePortfolio constructionThe 3% to 5% “cowboy account”Ritholtz Wealth ManagementHow Not to InvestThe purpose of moneyChapters00:00 Getting Rich Slowly00:57 Writing as an Investing Tool03:29 The Simple Path to Wealth05:00 Why Humans Are Bad at Investing06:22 Financial Media and Investor Behavior09:46 Why Short-Term Market Noise Doesn’t Matter11:19 Nobody Knows What Comes Next12:00 John Wick and the Problem With Forecasting13:00 Why Most Active Managers Underperform14:02 Why Big Market Forecasts Usually Fail16:33 Financial Crises and the Power of Markets17:59 How Barry’s Investing Philosophy Changed22:41 Lessons From Ray Dalio, Howard Marks, and Kahneman26:09 The Case for Index Funds27:40 Barry’s 3% to 5% “Cowboy Account” Strategy29:10 What Investors Actually Need From an Advisor31:10 Direct Indexing and Tax-Loss Harvesting34:10 Why Extreme Frugality Can Backfire36:38 What Money Is Actually For39:19 Spend Less Than You Make, But Enjoy Your Life41:32 Book Giveaway and ClosingSubscribe to Founders & Friends for candid conversations with investors, market strategists, financial journalists, founders, and people shaping the markets.#Investing #StockMarket #BarryRitholtz #WealthBuilding #LongTermInvesting

Adam Parker of Trivariate Research joins Michael Monaghan on Founders and Friends to discuss NVIDIA, the AI supercycle, semiconductor stocks, stock market strategy, valuation, portfolio construction, and where investors may still have an edge.In this episode, Adam Parker explains why the AI investment cycle may still have years to run, why NVIDIA could potentially reach a $10 trillion market cap, and why traditional valuation metrics do not always work when selecting stocks. He also discusses Micron, memory stocks, semiconductor cyclicality, AI earnings estimates, physical AI, humanoid robots, healthcare stocks, data centers, U.S. manufacturing, and the impact of artificial intelligence on jobs and productivity.Michael and Adam also explore long-term investing versus short-term trading, hedge fund pod shops, risk management, portfolio diversification, leveraged ETFs, zero-day options, and how investors should think about finding alpha in today’s market.Adam shares lessons from his career at Sanford Bernstein, Morgan Stanley, Eminence Capital, and from founding Trivariate Research. He also discusses TriVector Research, his investment research platform for individual investors and financial advisors.Topics include:NVIDIA stock and the AI supercycleNVIDIA $10 trillion market cap potentialAI investing and semiconductor stocksMicron and memory stocksStock valuation and earnings estimatesLong-term investing vs. short-term tradingHedge funds and multi-manager pod shopsPhysical AI and humanoid roboticsAI and white-collar jobsHealthcare investment opportunitiesData centers and AI infrastructurePortfolio construction and risk managementLeveraged ETFs and zero-day optionsFinding alpha in the stock marketAdam Parker’s investing frameworkTrivariate Research and TriVector ResearchChapters:00:00 Nvidia Supercycle Teaser01:01 Meet Adam Parker01:32 Flexibility as Alpha04:19 Long Term vs Pod Shops07:37 Why Valuation Misleads10:42 Bernstein Semis Origins13:00 Micron From Disaster to Titan16:04 Are Memory Stocks Still Cyclical18:21 Nvidia to Ten Trillion23:38 AI Estimates Still Too Low26:13 What Could Go Wrong30:03 Physical AI and Humanoid Care32:53 Humanoids And New Jobs33:38 Debt Fears And Markets35:40 AI Purpose And Joy37:01 College ROI And Trades39:26 Data Centers And Narratives41:09 Productive Years And Healthcare43:30 Portfolio Strategy Not Calls46:39 Trivector Edge And Clients48:37 Career Speedrun And Newsletter52:52 Leveraged ETFs And Zero DTE57:42 Running Your Own Firm01:02:52 Wrap Up And Where To Subscribe

Father and son. Both left Merrill Lynch to build a firm of their own.Bob and Ryan Payne took decades of experience inside Wall Street and chose a different path: building Payne Capital Management as an independent advisory firm around their own philosophy, processes, and approach to clients.In this episode, Michael Monaghan sits down with Bob and Ryan to talk about what pushed them toward independence, how they scaled from advisors working one account at a time into business builders, and why they believe some of the best ideas in financial services come from thinking outside the industry.They also discuss contrarian investing, investor psychology, why human behavior matters more than predicting markets, what founders and entrepreneurs do differently, and what Bob has learned over more than 50 years in the financial industry.And behind it all is a unique partnership: a father and son who built the business together, remain 50/50 partners, and say they have never had an argument about the direction of the firm.Chapters00:00 Meet Bob & Ryan Payne00:38 What Running Teaches You About Business02:20 The Turning Point in Building Their RIA05:00 What Bob Learned at Merrill Lynch07:38 Why the Future Was Independent10:26 Putting the Client Before the Product11:31 Building an RIA Differently14:04 Why It Pays to Be Contrarian15:16 Building a Business as Father & Son18:04 Ryan on Media, Music & Entrepreneurship20:09 The Psychology Behind Investor Mistakes24:20 Why Consensus Can Be Dangerous25:47 “You Make All Your Money in Bear Markets”26:35 What Founders Do Differently28:36 What It Really Means to Be an Entrepreneur30:23 Success, Optimism & Enjoying the Process32:40 The Lessons That Matter After 50 Years34:32 Closing Thoughts

In this episode of Still Building, Michael sits down with long-time friend, author, and wealth advisor Frazer Rice to talk about what it actually takes to preserve and protect multi-generational wealth.While traditional wealth management often focuses purely on investments and tax planning, Frazier shares why the biggest threats to wealth aren't bad markets, they're communication breakdowns, lack of execution, and unaddressed family dynamics.CHAPTERS00:00 Introducing Frazer Rice01:02 What makes Next Capital different02:39 Planning before a founder’s liquidity event03:58 Passing down values and legacy04:41 How generational wealth can go wrong06:04 Concentration vs. diversification08:45 Bill Gates, Steve Ballmer, and Kodak10:42 Balancing family priorities11:36 When founders should begin planning12:30 When to involve the next generation14:59 Building plans that are durable and flexible16:13 Frazer’s background in law and wealth management19:58 Lessons from writing a book about wealth21:51 Advice for the next generation of advisors22:40 How to connect with FrazerConnect with Frazer:Website: next-vantage.com / wealthactually.com