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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

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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

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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

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And now for this week’s prescription:

On this week’s dose, we begin (1:33) with Roon, a digital health startup aiming to replace “Dr. Google” with trusted doctor-driven video content, fresh off a $15M Series A. Next (7:54), we spotlight Slip Robotics, the Atlanta-based innovator transforming logistics with its SlipBot Automated Loading Robot, and their $28M Series B. Finally (16:18), we turn to Boom Supersonic, the aerospace pioneer securing over $100M to fund "Symphony," its first supersonic jet engine prototype.

Sources:

https://www.roon.com/

https://techcrunch.com/2024/11/26/roon-raises-15m-to-replace-dr-google-with-real-doctors-sharing-videos-about-illness-treatments/

https://techpadi.africa/2024/11/nyc-based-health-guidance-platform-roon-secures-15m-in-series-a-funding/

https://www.wect.com/2019/06/24/study-finds-us-citizens-turn-google-before-their-doctor/#:~:text=WILMINGTON%2C%20N.C.%20(WECT)%20%2D,before%20going%20to%20their%20doctor

https://techfundingnews.com/roon-doses-up-on-15m-funding-to-replace-dr-google-with-expert-healthcare-answers/

https://blog.roon.com/post/roons-next-chapter-one-step-closer-to-a-doctor-in-your-pocket-for-health

https://www.sliprobotics.com/

https://techcrunch.com/2024/12/17/slip-robotics-snags-28m-for-its-bots-that-can-load-a-truck-in-five-minutes/

https://www.ourcrowd.com/startup/slip-robotics?utm_source=chatgpt.com

https://boomsupersonic.com/

https://viewfromthewing.com/rejected-by-the-industry-boom-supersonic-raises-100m-to-prove-critics-wrong-but-at-a-cost/

Music Credit: Chapter One by Cole Bauer and Dean Keeton

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And now for this week’s prescription:

On this week’s dose, we start (1:52) with a breakdown of Growl, a connected fitness startup aiming to create the “Peloton of Boxing,” fresh off a $4.75M seed round. Next (12:38), we spotlight Liquid AI, a company taking a radically different approach to AI by modeling their technology on the brain of a worm rather than a human, backed by a $250M funding round. Finally (18:08), we wrap up with a deep dive into Public, a startup empowering users to invest smarter. What began as a social stock trading platform has evolved into an AI-enabled investment tool, fueled by their recent $135M Series D.

Sources:

https://www.joingrowl.com/

https://techcrunch.com/2024/12/04/growl-is-building-the-peloton-of-boxing/

https://www.sportsbusinessjournal.com/Articles/2024/12/04/growl-funding

https://www.globenewswire.com/news-release/2024/12/04/2991330/0/en/GROWL-Raises-4-75M-to-Launch-the-World-s-First-AI-Powered-Life-Sized-Interactive-Boxing-Fitness-Coach-for-the-Whole-Family.html

https://www.liquid.ai/

https://www.liquid.ai/blog/we-raised-250m-to-scale-capable-and-efficient-general-purpose-ai

https://public.com/

https://medium.com/the-public-blog/public-announces-135m-series-d-2-capital-raise-8eef9f33b2ad

Music Credit: Chapter One by Cole Bauer and Dean Keeton

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On this week’s dose, we have Mike Panos, Vice President of Operations at SkyFi, an Earth intelligence platform providing user-friendly access to geospatial data for individuals, SMBs, enterprises, and government agencies. Mike kicks things off by sharing his impressive journey, including 10 years in the US Navy, earning an MBA from Harvard, and eventually joining SkyFi in Austin. From there, he dives into SkyFi’s mission to bridge the gap between the growing demand for geospatial data and satellite operators focused on government contracts. Mike also shares insights into SkyFi’s growth plans, how they fit into the expanding satellite and geospatial data industry, and teases some exciting upcoming developments for the team. We wrap up with valuable advice for aspiring entrepreneurs in the Pillgrim community.

Sources:

https://skyfi.com/

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

Music Credit: Chapter One by Cole Bauer and Dean Keeton

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On this week’s dose, we have Sergey Gribov, Partner at Flint Capital, an early stage VC firm based out of Boston that invests in the greatest companies from the US, Israel, and Europe and helps them by being a bridge to the US market. Sergey kicks things off by sharing insights from his early career as employee #1 at Compugen, one of Israel’s pioneering startup success stories. He also offers a deep dive into the Israeli startup ecosystem, highlighting its unique attributes. From there, Sergey discusses what founders should prioritize when selecting investors and what he and the Flint Capital team look for in founding teams. Stay tuned for Sergey’s perspective on the AI space, how he assesses AI investment opportunities, and his vision for the future of the Israeli startup ecosystem. We wrap up with valuable advice for aspiring venture capitalists in our Pillgrims community.

Sources:

https://flintcap.com/

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

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 start (1:46) with a breakdown on Infinite Machine, a startup designing high-performance electric scooters tailored for urban environments, which recently raised a $9.3M seed round.. Next (10:14), we spotlight SuppCo, an app designed to personalize and track users’ supplement “stacks,” supported by a $5.5M seed round. Lastly (20:40), we wrap up with a deepdive on Waymo, Alphabet’s autonomous vehicle robotaxi service, which secured a landmark $5.6B Series C round.

Sources:

https://www.infinitemachine.com/

https://www.infinitemachine.com/newsroom/infinite-machine-raises-9-3m-in-seed-round-led-by-a16z-to-fuel-non-car-revolution

https://supp.co/

https://supp.co/about/beta

https://waymo.com/

https://waymo.com/blog/2024/10/investing-to-bring-the-waymo-driver-to-more-riders/

https://www.cnbc.com/2024/10/25/alphabets-self-driving-unit-waymo-closes-5point6-billion-funding-round.html

Music Credit: Chapter One by Cole Bauer and Dean Keeton

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