Investing in Startups

Charles Hudson, Managing Partner and founder of Precursor Ventures, shares his expertise as a seasoned investor in over 400 startups. He emphasizes the importance of founder-centric investing, the challenges of liquidity in early-stage ventures, and the need for a resilient firm structure. Hudson also discusses how market forecasting can be tricky, advocating for focusing on founders instead. He provides insights on varying LP expectations and the potential pitfalls of early employee hires, highlighting the evolving landscape of venture capital.

David Cohen is the CEO and Cofounder of Techstars. Techstars is one of the OGs of startup accelerators, investing in almost 5,000 startups since Techstars was founded in 2006. David himself is a serial entrepreneur who was the founding CEO at Techstars, later stepped back from that role, and then returned as CEO in 2024. We talked about the problems that Techstars solves for founders, how vibe-coding affects accelerators, why Techstars finally opened up in SF, and why bigger isn’t better – better is better. Please enjoy.    A few longer highlights:   Techstars was founded to create a supportive community for entrepreneurs. The accelerator model has evolved, with many new players in the market. Quality of support is more important than the number of companies funded. Techstars is focused on improving the offer for founders to attract high-quality startups. The network of mentors and alumni is a key asset for Techstars. Founders often come in with hubris but learn to embrace feedback. The experience of founders in the program can lead to significant transformations. Market selection is based on capital availability and community strength. Techstars aims to maintain quality while allowing MDs autonomy in decision-making. AI is changing the landscape of startup development, emphasizing storytelling and long-term vision.   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Gigi Levy-Weiss is a serial founder and a Founding Partner at NFX. NFX is an early-stage firm that has established itself as one of leading experts in network effects. We talked about network effects, AI agents, the importance of speed of exectuion, why first-mover advantages are overrated, and how NFX has built its own brand, systems, and network effects.    We also covered:   Going global without going local — Despite a 10-hour time gap between Israel and Silicon Valley, NFX partners rejected the easier path of separate regional funds, instead building a fully integrated, unified investment process based on trust, asynchronous communication, and individual founder meetings. Content as a competitive weapon — Early, sustained investment in short-form, actionable founder content gave NFX outsized market presence. Articles like the “Network Effects Bible” turned content into a persistent competitive advantage, positioning NFX as the definitive voice on network effects. AI's future is agent-to-agent, not agent-to-human — Gigi sees current AI implementations as merely transitional (agent-to-human workflows), predicting the true revolution lies in agent-to-agent interactions, cutting entire human-dependent processes from months down to minutes. B2C is AI’s biggest opening — Contrary to many investors betting big on AI-driven enterprise SaaS, Gigi argues consumer and SMB markets offer more attractive opportunities. Large enterprises will adapt quickly, limiting disruption, while SMBs and consumer verticals are ripe for agent-first innovation. First-mover advantage is overrated — Gigi challenges the widely-held VC belief in the inherent value of being first. Pointing to past failures, he argues that "being great is more important than being first," and successful fast-followers often become category leaders. Great products rarely sell themselves — Founders mistakenly obsess over perfecting product details (“product delusion”), yet distribution and defensibility usually matter more. NFX advocates for “product-market-network-distribution fit,” highlighting cases like Craigslist where distribution outshone product polish. VC needs its own disruption — NFX built internal VC tooling (“The Force”) and founder-focused products like Signal and BriefLink, seeing tech-driven innovation as essential for winning deal flow. They reject the outdated assumption that every industry except VC itself can be disrupted by technology.   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Josh Muccio is the Founder of The Pitch and The Pitch Fund. The Pitch is a show that features startup founders pitching a panel of VCs and getting live-fire feedback. The Pitch Fund invests in Josh’s favorite startups that appear on The Pitch. We talked about the behind-the-scenes of how the show works, pitching, whether the market matters more than the founder, and the dangers of consensus investing.   We also dove into:   – Josh shares how selling an iPhone-repair startup and falling in love with Gimlet’s Startup podcast led him to create The Pitch to “democratize access” to startup investing and storytelling.    – Why The Pitch is “like Shark Tank for tech” but with real, check-writing VCs. Less ego, more thoughtful questions, and founders who actually get funded.    – Inside the funnel: ~1,000 companies apply each season; venture partner Peter Liu screens hundreds before Lisa Muccio and Josh decide who records—only after all three have met the founder to curb bias.    – The backstory of The Pitch Fund and Josh’s investing rubric: market > founder > product—he weights market roughly 60 % and warns that even great founders struggle in weak markets.    – Railing against “consensus chasing,” he argues that investing purely for quick mark-ups hurts returns and founders; instead, he hunts non-consensus deals—like a snack-chip startup he backed at a $4 million valuation.    Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Shawn Merani is the Founder and Managing Partner of Parade Ventures. Parade is a seed stage venture firm with an affinity for enterprise software. We talked about the state of seed investing, relationships, observing vs. predicting, cheating, AI and a huge win Shawn had recently with the acquisition of Moveworks. Shawn is a sharp guy and this was a really fun conversation. Please enjoy.   We also covered:   The story behind Shawn’s early bet on Moveworks — and what made the founders stand out Why Shawn isn't big on predicting market trends How Shawn thinks about building high-conviction, concentrated portfolios The rise of secondary sales and what they mean for early-stage investors Why Shawn still believes in the power of enterprise software despite the hype cycles How he balances being relationship-driven with moving fast in today’s competitive seed market Shawn’s candid take on AI: opportunity, overuse, and what actually matters Why he tells his Berkeley MBA students that cheating only hurts themselves (and how he really feels about grades)   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

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.