The Scott Show

In this episode of The Scott Show, Scott sits down with Henry Yoshida, founder of Rocket Dollar and now head of Retired.com, to talk about the massive wave of innovation coming to the $18 trillion retirement market. From launching Rocket Dollar to help everyday investors use their IRAs to invest in real estate, startups, and crypto — to now running Retired.com with a vision for a fully self-directed retirement future — Henry breaks down how we’re on the verge of a generational unlock in private market access. Scott and Henry dive deep into the rise of private equity for retail investors, the shrinking public markets, and why the 401(k)-only model is bleeding out. Bonus: Scott unpacks the implications of Robinhood’s tokenized stock announcement and Republic’s tokenized forward contract product “Mirrors”, and debate whether tokenization is a feature or the product. What You’ll Learn: - Why your IRA is the smartest way to invest in alternatives - How Rocket Dollar lets you deploy dormant dollars into private equity, real estate, and crypto - What Robinhood’s tokenized stock move really means - Why Republic’s “Mirror” might be the most innovative product in fintech right now - The real future of tokenization: stablecoin rails, 24/7 trading, and AI-powered portfolios. Support the show by creating a free account at Kingscrowd.com Follow Henry at Retired.com Follow Scott on IG/Twitter @Kitun

In this episode of The Scott Show, Scott sits down with Acquire.com founder and CEO Andrew Gazdecki to explore the fast-growing world of micro acquisitions. From his early Twitter rise to landing the premium domain Acquire.com, Andrew shares how he built a breakout marketplace where anyone—from side hustlers to solopreneurs—can buy or sell profitable businesses with ease. Scott and Andrew dive into the future of entrepreneurship in a post-AI economy, where owning digital assets like newsletters, SaaS products, or niche content brands may be the new path to self-employment. They break down how Acquire.com works, why niche is the new scale, and how the platform unlocks liquidity for founders who might otherwise have no path to exit. Plus, Andrew shares his brand-building playbook: bootstrapped growth, the art of founder-led marketing, and how a he bought an entire category for $200K. What You’ll Learn: - Why micro acquisitions are the future of entrepreneurship - How Acquire.com is changing the game for bootstrapped founders - The power of premium domains and founder-led branding - Why the “dream” phase of a startup often beats early revenue - What solopreneurs should build, buy, or sell in a post-AI world Support the show by creating a free account at Kingscrowd.com. Follow Andrew on Twitter @agazdecki Follow Scott on IG/Twitter @Kitun

Scott’s back with golf betting consigliere Joe Koziol to preview the 2025 US Open at Oakmont, the hardest test in golf—and the most honest major to bet. The guys break down who can survive the brick-wall greens, brutal rough, and USGA sadism, then roll through their top plays, longshots, and the unofficial return of their flagship segment: Guy Stuff. What You’ll Learn: Why Oakmont rewards discipline, not dopamine Scott’s favorite Top 10 prop that’s free money (he swears) Joe’s sleeper pick who’s either missing the cut or finishing T-3 The one LIV player neither of them will touch Why betting the cut line might be more fun than betting the winner Follow Scott on IG/Twitter @kitun

Scott's back with his golf wagering pal Joe Koziol to break down this week's PGA Championship and whether or not Quail Hollow is just "Rory McIlroy Country Club". The two discuss a few emerging storylines such as; will Jordan Spieth sneak into the elite Grand Slam club? Who has the tastiest odds coming into the weekend, and whether or not the PGA made the right call moving its championship to May. 📓 What You’ll Learn: - Top bets, longshots, and DraftKings pool plays from $7,500–$9,500 - Why Scottie Scheffler might run away with it—and why Rory still gives pause - The problem with Rahm - Why 4-times per year Bryson, is the perfect amount of Bryson 🔥 Featured Picks: - Keegan Bradley (110:1): The degenerate’s dream and Ryder Cup chaos agent. - Victor Hovland (50:1): High ceiling, high variance—he’s one swing from elite. - Patrick Cantlay: Secretly cool IRL? Scott thinks so. Support the show by creating a free account at kingscrow.com. Follow Scott on IG/Twitter @kitun

This week, something seismic happened in private markets. Jeff Bezos, Michael Dell, and Coatue’s Philippe Laffont announced a $1B tech fund that’s now accessible to individual investors — with minimums starting at just $50K. Let that sink in. The floodgates are opening. What used to require millions and insider access is now coming to retail. First Hamilton Lane launched the first truly retail private fund exclusively on Repubic with a $500 minimum and now Coatue offering access to its own unique offering at $50k (funds like these typically have minimums in the millions). In this episode, Scott is joined by KingsCrowd's Head of Product, Brian Belley, to unpack the real impact of this new "public-private" trend — and how everyday investors (and fintech bros) can take advantage of this radically evolving market. What they discussed: - Why this marks the official arrival of the retail private equity era - The pros, cons, and potential traps for new investors - How to build a modern portfolio without getting wrecked by fees, hype, or fine print - Why the next generation of private investing will blur the lines between public and private assets Support the show (and your wallet) by creating a free account at Kingscrowd.com. Follow Brian @ Linkedin.com/in/brianbelley Follow Scott on IG/Twitter @Kitun

Scott sits down with venture capitalist, essayist, and Slow Ventures GP Sam Lessin for a candid, high-signal conversation about the state of venture capital—and why the old playbook is officially dead. Sam unpacks the ideas behind his viral VC25 manifesto, including why the startup conveyor belt model is broken, how today’s founders are flying blind, and what it really takes to build something worth betting on in a post-factory era. Together, Scott and Sam dive deep into the evolving role of seed investors, the myth of the “10x engineer,” and why most unicorns are now zombified corpses soaking up capital and talent. They riff on founder delusion, LP dysfunction, the commoditization of software, and how a new generation of operators must be built for long-term reality—not short-term hype. It’s a provocative, honest, and sometimes brutal look at how we fund, build, and believe in companies today—and why SFD (Straight F*cking Down) might be the new north star for modern venture. What You’ll Learn: -- Why the “VC Factory” model is gone for good -- How to survive as a seed fund in the mega-fund era -- Why great companies must now be built for forever, not acquisition -- What matters more than tech: story, founder, deal Support the show (and your wallet) by creating a free account at Kingscrowd.com Follow Sam Lessin on Twitter @lessin Follow Scott on IG/Twitter @Kitun

Scott sits down with longtime friend, journalist, and cultural critic John McDermott for a no-holds-barred conversation on the rise of the grift economy. John and Scott re-trace the evolution of modern hustle culture to unpack the cult of tech founders, the blurred lines between personal branding and deception, and why irrational self-confidence is both a feature and a bug of startup life. Along the way, the duo riff on everything from J.R. Smith’s delusional greatness to Mark Zuckerberg's masculinity arc, fake wellness routines, and the eerie emergence of AI-driven misinformation. John shares what it was like to go toe-to-toe with Jay Shetty, the media’s retreat from accountability, and how we're all becoming lone agents in a broken information ecosystem. It’s a sharp, funny, and sobering look at an era where everything is a grift—and everyone’s a brand. What You’ll Learn: -- Why the “rise and grind” founder archetype is built on delusion -- How fake personas thrive in a media landscape with no referees -- Why we’re only at the beginning of the grift era—and how AI will amplify it -- What snake oil salesmen of the 1900s can teach us about today’s digital hucksters Support the show (and your wallet) by creating a free account at Kingscrowd.com Follow John McDermott on Twitter @McDermott Follow Scott on IG/Twitter @Kitun

In this episode, Scott sits down with legendary host and comedic trailblazer Craig Kilborn for a wide-ranging conversation on life after late night, creative independence, and what it really means to stay above the fray. From his iconic runs at ESPN, The Daily Show, and The Late Late Show, Craig reflects on the highs of fame, why he walked away, and how he found peace (and punchlines) off-camera. Scott and Craig share their philosophies on aging gracefully, drinking in moderation, and never chasing the night. They riff on Frasier, Scotch, the Reuben sandwich, and their favorite rewatchable movies—from Predator to North by Northwest. Plus, Craig shares what he’s up to now with his podcast The Life Gorgeous, his love for California road trips, and why leadership and attitude matter more than ever. Lessons Learned: - Why Craig Kilborn left late night at the top—and doesn’t regret it. - How to craft a creative life without burnout or bitterness. - Why being genuinely happy is a competitive advantage. - What makes a sandwich truly great. Support the show by signing up for a free account at KingsCrowd.com Subscribe to Craig’s podcast: The Life Gorgeous Follow Craig on Instagram: @mrcraigkilborn Follow Scott: @kitun

A different tradition unlike any other... Gambling on golf. Welcome to Scott Show: Masters Week Edition. Scott is joined by local legend and friend Joe Koziol to dive deep into one of the year’s most beautiful, chaotic, and bank-breaking sports weekends, The Masters 🏌️‍♂️ A few highlights: - Why the Masters is our Super Bowl - Intruiging bets, props, and pools - The case for Maverick McNeely at +750 - Angel Cabrera… yes, that Angel Cabrera - Golf psychology - Masters Pool Draft: top picks to win, best old guys, young studs and who's to lose This episode has rare degenerate energy with just enough stats to sound smart. Unoffical Sponsor of this week is Montucky Cold Snacks -- please drink (and gamble) responsibly. Follow Scott: @kitun

In this episode, Scott sits down with journalist-turned-operator Eric Newcomer for a wide-ranging conversation about building in public, the evolution of venture capital, and what it’s really like to run a media business. Eric shares the backstory of launching Newcomer, from a solo Substack to a $2M+ revenue business with marquee events like Cerebral Valley. The two reflect on the blurred lines between media and entrepreneurship, how trust and access shape great reporting, and the surprisingly human side of building a company. Then, Scott and Eric dive deep into the state of venture capital: the private-equity-ification of mega-funds, the uncertain future for emerging managers, and why it’s getting harder to find the next generation of category-defining companies. Eric offers sharp takes on AI, fundraising hype, and what LPs really want. It’s a thoughtful, honest, and often funny look at what happens when a journalist steps behind the curtain and becomes a founder himself. What You’ll Learn: - Why Newcomer leaned into events—and how it became a real business. - The unspoken truth about founder glorification (and how hard building really is). - How venture capital is shifting—and why SaaS may have spoiled the party. - What separates good journalism from performative puff pieces. - What it feels like to lead a small team and be responsible for real livelihoods. Bonus: Invest with your eyes not your ears. Markets tank following Trump tariffs. Support the show by signing up for a free account @ Kingscrowd.com Subscribe to Eric’s newsletter and podcast: Newcomer.co Follow Eric: @ericnewcomer Follow Scott: @kitun