The Information presents Modest Conversations hosted by Sam Lessin, who writes the site's regular 'Modest Conversations' column. Modest Conversations are short conversations with interesting people about technology, culture, politics, and whatever else strikes our fancy.
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Sam Lessin Podcasts
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.
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Robinhood Drops a Nuke, Republic Reinvents The Forward Contract, and Rocket Dollar Founder Henry Yoshida On Self-Directed Private Investing
47:32
47:32
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47:32
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 …
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The Business of Buying Businesses with Acquire.com CEO Andrew Gazdecki
34:18
34:18
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34:18
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 profitab…
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Retail Private Markets Mini Series Plug and US Open Week with Venmo Joe Koziol
44:33
44:33
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44:33
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 Stuf…
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PGA Championship Storylines, Value Picks and Errant Takes with 'Big Kit & Venmo Joe'
44:54
44:54
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44:54
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 m…
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Why Jeff Bezos, Coatue Launched a New Billion Dollar Private Fund For Individual Investors
42:27
42:27
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42:27
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 H…
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RIP Venture Factory and The State of VC 2025 with Sam Lessin
38:09
38:09
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38:09
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 blin…
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Surviving The Grift Economy with Pop Culture Journo John McDermott
48:56
48:56
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48:56
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…
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Craig Kilborn's Gorgeous Life, All-Time Sandwich Rankings, and Scott's Masters Weekend Recap
42:30
42:30
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42:30
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, an…
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The Masters Edition featuring Scott's Friend "Venmo" Joe
48:25
48:25
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48:25
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,…
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Markets Tank, Stop Listening to Noise, “Private Equitification” of Venture and the New Media Universe with Eric Newcomer
47:05
47:05
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47:05
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 Cerebr…
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Darren Marble on Going Public, Market Convergence, and the Retail Renaissance
41:00
41:00
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41:00
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 groundbreaki…
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Scott Has a New Show, Republic Launches "True Retail" Private Equity Fund w/ Hamilton Lane and Why Tokenize Private Equity w/ Republic Founder Kendrick Nguyen
44:32
44:32
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44:32
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-gra…
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From Mechanical Engineering to Studio Head: Jeff Annison's Legion M Story
40:41
40:41
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40:41
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 ins…
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Taylor Lorenz on Being Extremely Online in an Internet World
28:56
28:56
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28:56
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…
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The Crowdfunding Revolution: A Conversation with StartEngine's Howard Marks
42:52
42:52
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42:52
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 reflect…
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Alts, investing and the promise of fine art with Masterworks CEO Scott Lynn
26:09
26:09
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26:09
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 share…
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Bored Elon Musk on Elon, startups, crypto and pseudonym life
33:31
33:31
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33:31
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…
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Harper Reed on making tech more accessible
39:14
39:14
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39:14
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, Re…
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Getting more out of your education minus the debt sentence
41:04
41:04
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41:04
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 …
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Changing the culture around investing with StartupStarter co-founder Lorel Scott
40:03
40:03
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40:03
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 c…
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Backstage Capital GPs on the present/future of VC and new partnership with KingsCrowd
41:21
41:21
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41:21
Brittany Davis and Christie Pitts, general partners at Backstage Capital, join the show with Scott Kitun. Brittany and Christie talk about the present day investing landscape and why the future of VC will trend towards inclusiveness (or lose). The group shares their thoughts and experiences with the top VC firms, why so many are resistant to change…
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Creating futuristic vehicle concepts with VonMercier
30:37
30:37
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30:37
Mike Mercier, founder and CEO of VonMercier, joins the show with Scott Kitun. They talk about how changing what we can do with vehicles, starting with the idea of VonMercier's electric hovercraft Arosa. Mike dives into his 10-year founding journey with late nights and weekends dedicated to coming up with the concept, finding the right materials and…
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Showplace is your one-stop shop for outfitting short-term rentals
37:46
37:46
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37:46
Justin Miller, founder and CEO of Showplace, joins the show with Scott Kitun. Showplace aims to be a one-stop shop for people looking to rent out their properties with the supplies, design, furnishings and everything else you need to set up a short-term rental. Justin shares the company's hefty aim to be the modern infrastructure for short-term ren…
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Improving shift work everywhere with Deputy CEO Ashik Ahmed
46:00
46:00
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46:00
Ashik Ahmed, co-founder and CEO of Deputy, joins the show with Scott Kitun. Deputy is a company focused around simplifying work life for the shift worker. As an employee management platform, Deputy specializes in timesheets, scheduling, tasks and workplace communication. Ashik shares the founding story starting with his own childhood growing up aro…
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S.I. Container Builds: Building ADUs with affordability and conservation in mind
24:03
24:03
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24:03
Rory Rubin, co-founder and CEO of S.I. Container Builds, joins Scott Kitun on the show. S.I. Container Builds offer customizable ADUs (accessory dwelling units) using shipping containers that are affordable, simple and environmentally conscious. Rory shares with Scott the origin story for starting S.I. Container Builds. According to Rory, there are…
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