May 25, 2018 · 37m · 20vc
20VC: The Core Lessons From Building a 150 Startup Angel Portfolio, Why Founders Who Angel Invest Have Such Strong Advantages and Why The Lean Startup Makes Less and Less Sense Today with Adrian Aoun, Founder & CEO @ Forward
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In this episode of The 20 Minute VC, host Harry Stebbings interviews Adrian Aoun, founder and CEO of Forward, about building full-stack healthcare platforms, rethinking the Lean Startup methodology for systemic industries, and the strategic advantages gained from maintaining a 150+ company angel investment portfolio.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 23.3% of the talking time here. How this is scored →
Harry as informed peer 3.2 Guest teaching 3.8 Guest disagreement 2.3 Harry pushing back 1.9
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 13:18 Rejecting the Lean Startup doctrine for hardware/healthcare systems
Adrian explicitly rejects Eric Ries' Lean Startup model for healthcare and systems problems, insisting that a lightweight MVP fails when a complete full-stack experience is required from day one.
Hardest push from Harry ▶ 18:44 Harry challenges regulatory risk exposureHarry forcefully questions Adrian from a VC perspective, asking why an investor shouldn't be deeply concerned about high dependency on external regulatory meta-bodies beyond the company's control.
Biggest teaching moment ▶ 15:57 Deconstructing the tech industry's misperceptions of regulationAdrian systematically educates Harry on regulation by breaking it into three clear categories, demonstrating how Silicon Valley entrepreneurs habitually throw their hands up in defeat before understanding regulatory realities.
Harry holds his own ▶ 18:44 Harry asserts investor thesis on external dependenciesHarry brings his own domain expertise as a VC to bear, pressing the guest on how to underwrite external regulatory risks that lie entirely outside management's control.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Adrian Aoun's Path to Entrepreneurship and Startups | 2 | 3 | 1 | 0 | Harry asks standard background questions about Adrian's path to entrepreneurship and key learnings. Adrian shares his early self-taught coding background and key principles like prioritizing problem meatiness over solutions. | |
| Evaluating Market Size versus Problem Meatiness in Healthcare | 3 | 4 | 3 | 2 | Harry contrasts VC preferences for large markets with Peter Thiel's focus on niche markets. Adrian challenges traditional market sizing, explaining how new tech creates entirely new markets and why problem value outweighs initial market dimensions. | |
| The Evolution of Consumer Branding and Disintermediation | 4 | 5 | 4 | 2 | Harry cites Scott Belsky and questions the relevance of the Lean Startup methodology today. Adrian politely dissents regarding Eric Ries' model, explaining that complex systems problems like healthcare require full vertical integration rather than lightweight MVPs. | |
| Demystifying Regulatory Fears in Healthcare Startups | 3 | 5 | 3 | 2 | Harry asks why Adrian views healthcare regulation as non-threatening. Adrian educates on the three distinct tiers of regulation, arguing that tech founders prematurely throw their hands up before seeking to understand regulatory frameworks. | |
| Patient Capital and Navigating Long-Term Systemic Bets | 5 | 4 | 2 | 5 | Harry pushes back from a venture investor perspective, questioning the danger of relying on external regulatory meta-bodies. Adrian responds by detailing patient capital strategy and predictable regulatory pace. | |
| The Strategic Advantages of Founder Angel Investing | 3 | 3 | 1 | 2 | Harry inquires about the pros and cons of founder angel investing. Adrian outlines his philosophy of paying it forward and gaining crucial pattern recognition from investing across 150 companies. | |
| Angel Portfolio Construction and Power Law Dynamics | 4 | 4 | 2 | 2 | Harry asks about portfolio mechanics, check consistency, and pro rata rights. Adrian explains the power law dynamics of venture outcomes and why he prioritizes founder success over demanding strict pro rata terms. | |
| Uncovering Venture Capital Behaviors in Downturns | 3 | 3 | 3 | 1 | Harry asks if angel investing unveiled the inner mechanics of VC behavior. Adrian candidly describes how VCs act during downturns, highlighting how angel networks act as a check against bad actors taking advantage of struggling founders. | |
| Quickfire Insights and Building a Scalable Global Healthcare System | 2 | 3 | 2 | 1 | Harry conducts the quickfire round on books, quotes, talent compensation, and crisis management. Adrian presents a contrarian view on talent, advising never to pay up in salary but rather in mission and environment. |
Statements from this episode (16)
Adrian Aoun raised Forward capital from Marc Benioff and Eric Schmidt
“To date, Adrian has raised funding from some of the true greats of the business, including Mark Benioff, Eric Schmidt, Joe Lonsdale, Aaron Levy, and Josh Kushner, just to name a few.”
Adrian Aoun's angel portfolio includes WorkRamp, Atrium, and Convoy
“Adrian's also a prolific angel investor With the likes of WorkRamp, Atrium, Convoy, and many more in his incredible portfolio”
Forward built a functioning physical doctor's office 90 days after launch
“90 days into starting forward, we had a full doctor's office up and running with real doctors, real patients.”
Adrian Aoun: Direct tech disintermediation makes consumer brands far more powerful
“Technology empowers us to make decisions for our own lives, as opposed to allowing others to do so. And as you do that, this notion of a consumer brand becomes Far more important and far more powerful.”
Adrian Aoun: Systems startups require an MVP covering the entire vertical system
“And the truth is that you can't go after systems problems until your MVP, your minimum viable product, is a version of the whole system.”
Adrian Aoun: Tech founders dismiss regulation prematurely due to online freedom
“We are so used to just being able to do whatever we want online that any sort of regulation we look at, and we honestly throw our hands in the air and say, ah, screw it. This is dumb. Before we even seek to understand.”
Adrian Aoun: Regulation is less prohibitive for startups than founders think
“I don't think it actually is as prohibitive for startups as people would imagine.”
Adrian Aoun targets unsexy sectors like energy, education, and healthcare
“As an angel investor myself, frankly, I love those. I'm not looking for the Get rich quick scheme. More what I'm looking for is things that are going to have massive, massive impact on the world. What are the next Google, the next Apple, but let's go after the…”
Adrian Aoun does not angel invest to generate financial returns
“The reason I angel invest is not because I'm hoping to make a return.”
Marissa Mayer invested as an angel in Adrian Aoun's startup Wavy
“So one of the angel investors in Wavy was Marissa Mayer. Now, Wavy was a search company, and Marissa at the time ran search at Google.”
Adrian Aoun has built an angel portfolio of nearly 150 startups
“I'm lucky to be in almost a 150 companies”
Adrian Aoun discloses early angel investment in Wish
“So for example, a company I'm lucky enough to be an investor in is wish which used to be called context logic.”
Adrian Aoun does not ask founders for pro-rata rights in angel deals
“I actually don't try and ask people for pro rata rights, et cetera. I figure, you know what, if I'm a helpful added value investor and it's good for the company and it's good for them, then they'll go ahead and they'll give me an allotment and they'll be nice.”
Adrian Aoun: Founders Fund and Khosla Ventures treat founders well during downturns
“The investors that I went with in forward, people like Founders Fund or Kosla, Keith Raboy at Kosla, who I know has been on your show. These are people that when times get tough have been good actors.”