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On this week’s dose, we have Larry Aschebrook, Founder and Managing Partner at G Squared, a venture capital firm specializing in growth-stage tech investments with a sharp focus on the secondary market. Larry kicks things off by sharing his fascinating journey from college athletics to the world of private markets, ultimately leading to the creation of G Squared.

From there, he dives into the firm’s unique thesis—why secondaries represent a critical liquidity bridge between early-stage startups and public exits—and how that insight has helped G Squared back iconic companies like Uber, Spotify, Airbnb, Instacart, and more. Larry also opens up about memorable wins, the deals that slipped through the cracks, and the hard-won lessons that followed.

We also get his take on some of today’s headline-making moves in venture, including Stripe’s choice to remain private and Robinhood’s bold attempt to democratize access to private investing. It’s a masterclass in venture strategy from someone who’s seen it all—tune in for a front-row seat to the stories and insights that have shaped some of the biggest names in tech.

Sources:

https://www.linkedin.com/in/larry-aschebrook-54724629/

https://gsquared.com/

Music Credit: Chapter One by Cole Bauer and Dean Keeton

https://www.instagram.com/deankeeton/?hl=en

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And now for this week’s prescription:

On this week’s dose, we welcome Hoolie Tejwani, head of Coinbase Ventures, the investment arm backing startups that align with Coinbase’s mission of creating more economic freedom worldwide. We kick off with how Hoolie got connected to Coinbase (2:13) and the origins of Coinbase Ventures before diving into their investment thesis and mission (4:28). He shares insights on his approach to investing in potential competitors (6:40) and how the team sifts through the noise (8:10) in such a fast-moving industry.

Next, we explore the synergies between AI and crypto (10:05), Hoolie’s perspective on meme coins (13:15), and how the new Trump administration (16:24) is shaping the regulatory landscape for both Coinbase and its portfolio companies. We also discuss Coinbase Ventures’ portfolio (19:02) and get an inside look at what it’s like working at a company that still operates with a startup mindset despite its massive scale (21:35). Finally, Hoolie shares his five-year predictions for crypto and AI (24:52), how he manages to stay up to date with everything happening in the space (26:59), and the best ways to follow along (28:42).

Sources:

https://www.linkedin.com/in/hoolietejwani/

https://www.coinbase.com/ventures

Music Credit: Chapter One by Cole Bauer and Dean Keeton

https://www.instagram.com/deankeeton/?hl=en

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And now for this week’s prescription:

On this week’s dose, we begin (1:42) with Gumloop, a startup that allows users to automate any workflow using AI without requiring any coding experience, hot off a $17M Series A. Next (10:13), we spotlight Oura, the pioneering sleep-tracking ring leveraging strategic partnerships to strengthen its position in the wearables market, fresh off a $200M Series D. Finally (17:22), we turn to xAI, Elon Musk’s contender in the AI arms race, breaking down their massive $6B Series C.

Sources:

https://www.gumloop.com/

https://blog.gumloop.com/gumloops-17m-series-a/

https://ouraring.com/

https://www.fiercehealthcare.com/health-tech/oura-closes-200m-round-boosting-smart-ring-makers-valuation-52b

https://techcrunch.com/2024/12/25/elon-musks-xai-lands-billions-in-new-cash-to-fuel-ai-ambitions/

https://x.ai/blog/series-c

https://pitchbook.com/news/reports/q3-2024-ai-ml-report

Music Credit: Chapter One by Cole Bauer and Dean Keeton

https://www.instagram.com/deankeeton/?hl=en