Investing in Startups

Jason Freedman is a serial founder and General Partner at Orange Collective. Orange Collective is a Y Combinator-focused venture fund that aims to invest in the most promising YC companies before Demo Day. We talked about YC, exits, AI, open source, raising founders up, and why ownership percentages are overrated. We also discussed:   YC’s radical candor + optimism Orange Collective’s super-power: “use the product” diligence Early, relationship-first checks beat ownership math Real-world example: Mastra AI Doubling down on AI infrastructure Why open-source wins long-term Exits require as much craft as fundraising “Raise founders up” in practice Ownership percentages are overrated   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Host Joe Magyer is on the other side of the microphone in this episode as we share a recent interview he did with Chris Hill on Money Unplugged. The conversation explores Joe's earliest experiences with money, including his first hustle, and his thoughts on compounding, debt, Warren Buffett, charity, and the timeless business lessons from Narcos: Mexico.   We also discussed:   The importance of early financial education and experiences. Influence of family, especially grandparents, on financial perspectives. Character-driven investing: the significance of doing business with good people. Debt aversion shaped by personal experiences and family lessons. The value of open conversations about money in families. Understanding the long-term benefits of compounding and investing early. The impact of Warren Buffett on the investing community and future of Berkshire Hathaway. Personal spending should align with what brings joy and happiness. Charitable giving can significantly improve quality of life for others. Media can provide valuable business lessons, even in unconventional formats.   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Our guest this week is Jamie Melzer, Managing Partner at Altra Venture Partners. Altra invests in late-stage and pre-IPO venture-backed startups via secondaries. Jamie took us on a behind-the-scenes tour of the secondary market, how it works, why it is relevant to early stage investors and founders, and where the market is heading. This was the first time we’ve talked about secondaries on Investing in Startups but it probably won’t be the last because it is becoming more important as startups stay private for longer. Please enjoy.   We also covered:   The nuts and bolts of a secondary deal—finding a seller, agreeing on price with scant data, and getting past ROFRs or outright company blocks that kill roughly a third of transactions. Why the late-stage secondary market now looks like public-equity investing, with the top 10 U.S. unicorns (SpaceX, Stripe, OpenAI, etc.) representing more than a third of all private-tech value—a true power-law. Common shares trading at premiums to fresh preferred rounds, and how hidden liquidation stacks can wipe you out if you don’t model the waterfall. The surge of giant institutional funds and private-wealth vehicles buying $100-300 M blocks—versus retail SPVs chasing “Birkin-bag” names like Anduril or SpaceX, often at double the institutional price. Lessons Jamie brought from distressed credit: pricing risk, valuing businesses bottom-up, and why share-class selection matters as much as entry multiple. Rethinking portfolio construction: focus on position size and access, not “own 10 %,” and accept that 15-30 late-stage names can give better exposure than hundreds of seed bets. How evergreen, index-style funds could let employees and early VCs tap liquidity every 6-12 months while letting new investors hold compounders indefinitely. The coming “secondary-of-secondaries” wave, when today’s growth-stage and secondary funds will themselves need liquidity from even later buyers.   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Our guest this week is Itamar Novick, Founder of Recursive Ventures. Itamar is a solo capitalist with a focus on pre-seed startups built around data and AI. We talked about the opportunities and challenges that AI presents, anti-patterns to avoid in startups, winning deals, and why Itamar thinks that most VCs do NOT add value to startups. Itamar has been a founder, executive, and investor, so this was a really thoughtful, nuanced conversation.    We also covered:   Common startup mistakes that feel smart but kill companies Lessons from a failed $50M strategic deal with ADT at Life360 What actually creates defensibility in generative AI startups Why valuations in AI aren't a full-blown bubble—yet Building a solo VC firm with AI as leverage (“Portfolio GPT”) The new era of lean, high-output startups—and what it means for VC Itamar’s go-to founder question: Why will you stay ahead five years from now? Why most “value-add” from VCs is overhyped   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Our guest this week is Tyler Norwood, Managing Partner for Antler in the US. Antler is the world’s most active seed investor backing founders at the inception stage from all over. We talked about the impact of vibe coding, the traits that Tyler sees in Antler’s most successful founders, why timing matters, and the value of surrounding yourself with other builders. Please enjoy.    Here are some bullets about today's show:   - Antler’s origin story and global footprint: launching in Singapore (2018) and scaling to 27 offices as the world’s most active seed investor- The Residency model: six‑week, community‑driven program backing founders at “day ‑1” with ~US $500k checks- U.S. expansion strategy: why New York and Austin came first and San Francisco’s “Death Star” was saved for last (plus Austin’s steep growth curve)- Founder superpowers—aspiration + agency: how Tyler tests for them (the “strange hobby” question) and why timing‑misaligned founders struggle- Vibe coding and generative‑AI tooling: 95 % AI‑generated codebases, faster product‑market‑fit loops, robustness can wait- Operator‑to‑investor realities: the hard math of a first 2 & 20 fund, living on fees for ~12 years, and why VC isn’t a quick win- Myth‑busting: the “ideas don’t matter” fallacy and the case for rigorous idea selection / founder‑market fit- Advice for aspiring VCs and founders: patient idea formation, exposing yourself to diverse problems, and how to connect with Antler   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Our guest this week is Han Shen, Founding Partner of iFly.vc. iFly is an early-stage firm with a non-consensus, high-conviction approach to investing. Han himself is a very successful investor but also matches that success with equal levels of modesty and empathy. We talked about investing in non-consensus startups in an industry that is very consensus-driven, the vibe shift, investing with conviction, and how Han was turned down by hundreds of investors for his first fund and still lived to tell the tale. Please enjoy.    Takeaways + Unsexy parts of the market can yield the best opportunities.+ Non-consensus investing allows for unique insights.+ Consumer spending is a massive market with evolving trends.+ Tech enablement is crucial for driving consumer innovation.+ Listening to customers is essential for success.+ Fundraising can be an emotional journey filled with challenges.+ Building relationships is key in venture capital.+ Diversity in investing goes beyond just ethnicity.+ Concentrated investing can lead to better outcomes.+ Continuous learning is vital for founders and investors alike.   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Ethan Austin is the Founder and General Partner of Outside VC. Outside is a Boulder-based firm with a focus on pre-seed startups, outsider founders, and financial inclusion. We talked about why Ethan whether investors should be friends with founders, fintech, what it was like running Techstars Boulder during Covid, and life as a solo GP. We dove further into the following topics:   Origin Story is Everything: Grit and personal motivation trump polish. Friendship = Honest Feedback: Real relationships demand tough truths. Running a Good Fundraising Process Matters: Smart process beats a perfect pitch. Pre-Seed Valuations Remain High: Founders must focus on momentum, not benchmarks. Solo Doesn't Mean Slower: Solo founders and GPs can move faster without decision bottlenecks. Financial Inclusion as a Driving Mission: Real impact over surface-level fintech hype. Consumer Startups Reawakening: Thanks to AI, the consumer space is interesting again.   Investing in Startups explores the strategies and stories of leading early-stage VCs. The show is hosted by Joe Magyer and produced by Seaplane Ventures.

Mark Peter Davis is the Managing Partner of Interplay Ventures. Interplay is a venture capital firm, but also an incubator and family office. Mark himself is a serial entrepreneur and also the host of the Innovation with Mark Peter Davis podcast, which is a great listen for founders. We talked about the mix of geopolitics and startups, what Mark needs to see from startups to invest, why ideas still matter, and advice on how to break into venture capital. Please enjoy.   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Elizabeth Yin is a General Partner at Hustle Fund. Hustle Fund invests in “hilariously early” startups in the US and beyond. We talked about Elizabeth’s favorite questions to ask founders, navigating disagreements in a healthy way, AI, the art of pitching, and why VCs should be a little more patient with founders. I really enjoyed this one and hope you do as well.    Takeaways:   Transparent Pitch Process: Hustle Fund publishes the questions they ask founders to reduce the “inside baseball” nature of VC pitching and level the playing field.   Zoom-First Approach: The fund avoids in-person meetings to ensure geographic and socio-economic equity for founders pitching them.   Favorite Founder Question: Elizabeth’s go-to question is “What is your burn rate?”—a straightforward yet revealing probe into financial discipline.    Healthy Disagreements: Disagreements within Hustle Fund’s partnership are frequent but productive, grounded in trust and transparency.   Unfair Advantage: Hustle Fund’s edge lies in ecosystem building—supporting founders through community, content, events, and distribution.    Hilariously Early Investing: Hustle Fund backs companies pre-revenue, often before product—but with a clear and nuanced understanding of the customer problem.   High Velocity Strategy: The firm backs ~250 companies per fund, mostly with a “one-and-done” strategy, occasionally following on through SPVs.    Angel Squad as a Force Multiplier: A 2,000-person global community designed to train, connect, and co-invest with emerging angels.   Founders Need to Create Urgency: Elizabeth emphasizes the importance of generating urgency in a raise—being a “great opportunity” is not enough.    Execution Speed is King: Hustle Fund prioritizes hustle—rapid experimentation and iteration—as a key signal for founder quality.   AI Investing Shift: While crowded, vertical-specific AI applications (especially in under-explored industries) still hold promise.   Patience is Under-Appreciated: Great companies like Webflow and NerdWallet often look like duds for years before compounding takes hold.   Path Flexibility Matters: Elizabeth encourages founders to evaluate what they want—venture-scale is not the only valid path to success.   VC Conventional Wisdom Challenge: She pushes back on “growth at all costs” and the notion that digital ads never work—they can, but must be used with discipline.   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Rick Zullo is the Founder and Managing Partner of Equal Ventures. Equal is a New York-based early stage venture capital firm that takes a concentrated approach with investing themes around climate, insurance, retail, and supply chain. We talked about why Rick invests with conviction, the state of seed investing, what climate volatility means for insurers and investors, and why being kind is more important than being nice. Enjoy.    Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.