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On this week’s dose, we’re joined by Mike Collins, CEO of Alumni Ventures, the largest venture firm in the U.S. dedicated to giving accredited investors access to professionally managed, diversified venture portfolios.Mike kicks things off by sharing his background and the early experiences that drew him into the world of startups and venture (2:00). He then unpacks how Alumni Ventures came to life and what inspired the model behind it. From there, he discusses how the firm began building access into venture investing at scale and started getting into deals by leveraging a powerful alumni-based network (7:53).(14:27) Mike then offers a primer on Alumni Ventures’ investment philosophy, walking us through how the firm thinks about raising capital and constructing portfolios. That leads into a deeper discussion about AV’s identity as a fintech company rather than a traditional VC, and how that mindset influences everything from internal operations to doing the hard things that come with scaling a venture platform (21:40).We then explore where AV is placing its bets, with Mike sharing sectors he’s particularly bullish or bearish on (26:13). That sets the stage for a broader conversation about the current AI wave and why it’s so central to both AV’s outlook and Mike’s personal conviction as an operator (30:54). He also gives us a look at what’s next on the firm’s roadmap and how AV plans to evolve in the coming years (32:50).As we move into the final stretch, Mike shares some of his more contrarian takes on venture and innovation (35:35), reflects on AV’s company culture (36:08), and offers insight into how he incorporates AI into his day-to-day leadership and decision-making (37:35). He names a few CEOs he models after (42:35), talks about how he unwinds with podcasts and uses low-tech strategies for deep focus (44:22), and gives some straightforward advice for those hoping to break into venture: just start doing the work (46:35).

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And now for this week’s prescription:

On this week’s dose, we start (1:59) with Alma, an AI-powered nutrition app using natural language processing to simplify meal tracking, fresh off a $2.9M pre-seed round led by Menlo Ventures’ Anthology Fund in partnership with Anthropic. Next (14:27), we pop open a deep dive on Olipop, the gut-friendly soda brand shaking up the functional beverage space, following a $50M Series C that brings its valuation to a bubbly $1.85 billion. Finally (24:01), we slice into Via 313 Pizzeria, the fast-growing Detroit-style pizza chain that just secured $32.5M in growth capital to fuel expansion across the U.S.Sources:

https://www.alma.food/

https://menlovc.com/anthology-fund/

https://techcrunch.com/2025/02/05/former-whoop-execs-new-app-alma-uses-ai-for-all-things-nutrition/

https://drinkolipop.com/

https://www.researchandmarkets.com/reports/4771906/functional-beverage-market-share-analysis?utm_source=chatgpt.com

https://www.foodbusinessnews.net/articles/27693-olipop-valued-at-185-billion-following-latest-funding-round

https://finance.yahoo.com/news/olipop-valued-1-85bn-following-125054362.html

https://www.bloomberg.com/news/articles/2025-02-12/olipop-valued-at-1-85-billion-in-50-million-funding-round?embedded-checkout=true

https://www.via313.com/

https://www.utahbusiness.com/press-releases/2025/02/05/via-313-raises-32-million-double-footprint/

https://www.nrn.com/restaurant-finance/via-313-pizzeria-raises-32-5m-in-growth-capital

Music Credit: Chapter One by Cole Bauer and Dean Keeton

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

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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

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