What happens when AI lets five people build what used to take fifty? Can you scale to eight figures in revenue without ever touching a “Series A treadmill”? In this episode, I talk with Henry Shi, co-founder of Super.com and creator of the Lean AI Leaderboard, about seedstrapping (raising once, then reaching escape velocity), outcome-based pricing, and a new, non-dilutive way to finance lean, profitable startups. We also get into how Henry “vibe-coded” an AI VC tool over a weekend, why survival rates should improve in the lean-AI era, and what founder traits show up again and again among these ultra-efficient companies.
Highlights:
- Why AI-native teams can hit $10M+ ARR with tiny headcount: lower fixed costs + higher willingness to pay for outcomes.
- Outcome-based pricing beats per-seat SaaS when you deliver measurable business results (example discussed: GrowthX).
- Seedstrapping defined: raise a solid seed round, then avoid the pre-seed→A→B→C treadmill by using capital discipline and AI leverage.
- Henry’s investor model: non-dilutive, non-recourse revenue share structured like a founder-optional line of credit (5–10% of revenue; 2–3× cap).
- Why “reach Series A” is a broken success metric—and why DPI/ongoing cash generation matters more.
- Founder traits that correlate with lean-AI success: repeat builders, high agency, resilience, and comfort going against pattern-matching orthodoxy.
- “Vibe-coding” an AI VC assistant in a weekend: auto-memos, competitor scans, forecasting, and draft term sheets.
- Will YC adapt—or will AI-native incubators centered on seedstrapping emerge? Henry’s take.
Guest Bio:
Henry Shi is the co-founder of Super.com (originally Snaptravel/Snapcommerce), founded in 2016 and rebranded to Super.com in Oct 2022 as the company expanded beyond travel into a savings-focused “super app.” WikipediaPR NewswireSuper Super.com raised $85M Series C in Apr 2023 (over $150M total raised reported at the time). PR NewswireCrunchbase News Henry also launched the Lean AI Leaderboard, tracking ultra-lean, high-revenue AI-native companies; he describes himself as a repeat founder who built a $150M+ annual-revenue startup before “recently exiting.” leanaileaderboard.com He was named to Forbes 30 Under 30 (Consumer Tech, 2019).
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Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Henry Shi: https://www.linkedin.com/in/henrythe9th/
Links:
Super.com: https://www.linkedin.com/company/superdotcom/
Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.
(0:00) Preview
(2:44) AI's Role in Lean High Growth Companies and Outcome-Based Pricing
(5:08) Ideal Capital Structure for AI Startups and Venture Capital Challenges
(7:53) Seed Strapping and its Suitability for Different Company Types
(10:24) Vibe Coding and AI's Potential to Support Diverse Founders
(15:26) Founder Characteristics and Incubator Models for AI Startups
(18:32) Seed Strapping Investment Model and Fundraising Challenges
(23:09) Startup Survival, Revenue-Based Funding, and Success Metrics
(30:04) Henry Shi's Fundraising Experiences and AI Startups' Potential
(32:52) Infinite Innovation and Encouraging Global Entrepreneurship
(34:03) Closing remarks
How I Invest with David Weisburd 
