Investing in Startups

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.

Sonia Nagar is the Founder and Managing Partner of SNAK Venture Partners. SNAK is a Chicago-based firm that invests in Seed stage marketplace startups. We talked about why SNAK loves marketplaces, what surprised Sonia about starting a new firm, why SNAK prefers B2B to B2C, first-mover advantages, and how AI has and hasn’t changed marketplaces. Please enjoy.   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Graham Pingree is a Partner at Cendana Capital, a fund of funds firm that invests in small venture funds investing at pre-seed and seed. We talked about why Cendana is focused on small funds, why it has a concentrated strategy, what the firm looks for in emerging managers, how to think about reserves and recycling, and why big venture firms are surprisingly hard to kill.    Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.

Jenny Fielding is a Cofounder and General Partner of Everywhere Ventures. Jenny is a pre-seed investor with a fascinating background. She’s a founder, lawyer by training, has lived in 12 countries, and ran Techstars New York for many years. She’s also the author of Venture Everywhere, a book which comes out in March. We talked about Jenny’s strategy, why venture doesn’t scale, why everywhere doesn't use follow-on capital in its funds, and how Everywhere is navigating the Seed and AI markets.    Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.   Investing in Startups: https://www.investinginstartups.com/ Joe Magyer: https://www.linkedin.com/in/joemagyer/ Seaplane Ventures: https://www.seaplaneventures.com/

We're celebrating our 20th episode with a super cut of 17 contrarian takes on venture capital and startups. Our guests talked about AI, SF, false signals from coinvestors, why venture isn't an access game, network effects, emerging managers, portfolio construction, and more. Special thanks to the following guests for their contributions to this episode:   Niki Scevark, Blackbird Ventures Martin Tobias, Incisive Ventures Mike Cardamone, Forum Ventures Nick Moran, New Stack Ventures Mac Conwell, RareBreed Ventures Rajiv Bala, Clutch VC Peter Walker, Carta Eric Golden, Canopy Capital Colin Gardiner, Yonder Ventures Zach Coelius, Coelius Capital Jerry Neumann, Neu Ventures   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.   Investing in Startups: https://www.investinginstartups.com/ Joe Magyer: https://www.linkedin.com/in/joemagyer/ Seaplane Ventures: https://www.seaplaneventures.com/

Amber Illig is the Founding General Partner of The Council, an early stage venture firm focused on essential industries like supply chain and healthcare. Amber has a deep operating background having worked at Apple, Cruise, Snap, and Eli Lilly. We talked about why Amber loves essential industries, how she built a proprietary network of operator angel investors, how she and that network help support founders, and her nuanced take on AI. Please enjoy.   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.   Investing in Startups: https://www.investinginstartups.com/ Joe Magyer: https://www.linkedin.com/in/joemagyer/ Seaplane Ventures: https://www.seaplaneventures.com/