Money Issues

Money Issues

Hosted by Scott Kitun, Money Issues dives into the strategies and stories behind modern capital formation and how today’s operators fund growth, stay liquid, and keep control.

Episodes

July 2, 2025 47 mins
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 break...
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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 i...
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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...
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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,...
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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 ...
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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...
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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 ...
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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 philos...
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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...
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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, h...
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In this episode, Scott sits down with Darren Marble — the creator of Going Public and founder of Issuance — for a wide-ranging conversation on the rise of retail investors, the evolution of equity crowdfunding, and why he believes the best days of this industry are still ahead. Darren shares the inside story of launching Going Public, a groundbreaking series now partnered with X (formerly Twitter), where everyday people can invest...
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In the inaugural episode of The Scott Show, host Scott Kitun welcomes his good friend and Founder of Republic, Kendrick Nguyen, to break some BIG news and to discuss the game-changing shift towards retail happening across private markets. Key Takeaways: → Republic’s Major Announcement – A new partnership with Hamilton Lane, bringing institutional-grade private equity to retail investors via blockchain tokenization. → The Power of...
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In this episode of the Technori podcast, host Scott Kitun interviews Jeff Annison, the co-founder and president of Legion M. They discuss Annison's journey from mechanical engineering to entrepreneurship, highlighting his experiences in various startups, including a streaming mobile television venture and a music-related startup. Annison shares insights into his career transitions, the challenges he faced, and the evolution of his ...

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Scott Kitun sits down with acclaimed journalist and author Taylor Lorenz to set the record straight regarding internet history, the premise of her book, "Extremely Online," (available now). She discusses the evolving landscape of the tech world, the importance of strong social safety nets, the impact of AI on content creation, and Lorenz's thoughts on various social platforms. 

Key Highlights:

  • The impact of social media on fame a...
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Scott Kitun talks to StartEngine co-founder Howard Marks. The conversation starts with Kitun's curiosity about Marks' early involvement in crowdfunding, despite having been an entrepreneur (founder of Activision) for a long time. Marks recounts his journey from investing in entrepreneurs in Los Angeles to eventually building StartEngine. He reflects on entrepreneurs' difficulties when raising capital, especially those who don't fit...

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Scott Lynn, founder and CEO of Masterworks, joins Scott Kitun on the show. As a long time art collector and enthusiast, Lynn saw a massive space in the market for fine art - which includes many pieces that are valued in the millions of dollars - to be invested in fractionally but art lovers and investors worldwide. In this episode, Scott Lynn shares his foray into entrepreneurship, developing the Masterworks platform and the promis...

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Bored Elon Musk, a pseudonymous influencer, joins Scott Kitun on the pod. Bored has built his following over most of the past decade on Twitter. What started out as a joke account gradually - alongside the growing notoriety of Elon Musk - into an influencer account with over a million followers. Bored shares how he built his following and monetized his account, including his Bored Box. Scott and Bored talk about the idea of playing...

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December 8, 2022 39 mins

Harper Reed, founder and CEO of Galactic, joins the show with Scott Kitun. Reed, the former Head of Commerce at Braintree and President Obama's CTO during his re-election campaign, is a longtime tech entrepreneur (and Technori supporter) working to make technology work better for everyone. Like many founders experienced early on in the pandemic, Reed had to make a major pivot. He shares his latest entrepreneurial journey moving Gal...

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Milan Kordestani, founder and CEO of Audo, joins the show with Scott Kitun. Audo is a career building platform that combines e-learning and job opportunities that fit the skills you learn. Scott and Milan dig into the changes coming to education, the value of college and avoiding debt. They also touch on just how gamification could and should play into the ways we learn, and building curriculum around engagement. Milan dives into h...

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Lorel Scott, co-founder and COO of StartupStarter, joins the show with Scott Kitun. StartupStarter is launching the first ever in-person Equity Crowdfunding Week (ECW), a showcase and awards show for equity crowdfunding startups and investors to come together for a 3 day celebration of a growing crowdfunding community. Lorel shares  how he and his co-founder came up with  StartupStarter in the height of the pandemic and have been w...

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