Navigating Startup Funding in the AI Era

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