Tough Questions, Hustle, and Investing in Hilariously Early Startups with Elizabeth Yin
- Joe Magyer
- Mar 31
- 3 min read
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.
The episode is now available on Apple Podcasts, Spotify, Amazon, and YouTube Music.
Chapters
Intro & Guest Welcome – [00:00]
Why Hustle Fund Shares Pitch Questions Publicly – [01:50]
Zoom-Only Meetings & Founder Accessibility – [03:00]
Elizabeth’s Favorite Founder Question (Burn Rate) – [04:30]
The Co-Founder Selection Goldilocks Zone – [05:30]
How Hustle Fund Navigates Internal Disagreements – [07:30]
Hustle Fund’s Ecosystem-First Advantage – [09:00]
What “Hilariously Early” Really Means – [10:30]
Portfolio Construction: 250 Pre-Seed Bets – [11:30]
Follow-On via SPVs, Not a Multi-Stage Fund – [12:30]
Angel Squad: Training 2,000 Emerging Angels – [14:30]
Fundraising is Not Sales: The Urgency Dynamic – [16:00]
What Separates Great Founders: Hustle – [18:00]
Ranking Product, Founder, Market – It Depends – [19:30]
Why Hustle Fund Prefers Small Fast-Growing Markets – [21:00]
Where AI Investment Makes Sense in 2025 – [22:00]
Founders in Crowded Markets: Bootstrap or Seedstrap – [24:00]
Using AI Internally for Content Ops – [24:30]
Advising Founders in No-Man’s Land – [26:00]
Some Wins Take Over a Decade to Bloom – [30:00]
Venture Conventional Wisdom Elizabeth Disputes – [32:30]
How Founders Can Pitch Hustle Fund – [34:30]
Takeaways: Elizabeth Yin of Hustle Fund on Investing Hilariously Early, AI, the art of pitching, and more
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.
The content here is for informational purposes only and should not be construed as investment, legal or tax advice. The opinions expressed by guests are their own and do not reflect the views of Seaplane Ventures. Our host, guests and clients may hold investments discussed in this podcast. Please invest responsibly.
