“You become known for the things that hit.”
Adrian Aoun is an investor in OpenAI, Anduril, Pinterest, Stripe, Airbnb, and Uber, among hundreds of other companies. He’s backed roughly 300 startups, about 40 of which are now unicorns or decacorns. He’s also an LP in around 100 venture funds.
Ask him about his investment thesis, and he’ll tell you he tries pretty hard not to have one.
“There’s more than one way to make money in this industry… I’m just going to describe what works for me. You can do what works for you.”
Here’s what he described.
TL;DR
- Angel investing is a numbers game. You can only lose 1x your money, but you can make 10,000x. That math demands volume and pattern recognition.
- Picking a thematic lane creates cognitive bias that pushes you toward the wrong founders. Airbnb and Anduril worked because they ran counter to the prevailing thesis of their day.
- The best founders attach to problems, not solutions. Solutions change constantly. Problems stay roughly the same for decades.
- The two-part founder test Adrian picked up from Larry Page. Do they believe something no one else believes? Will they walk through walls to make it happen?
- Adrian’s real competitive edge as a young angel wasn’t brand or money. It was effort, proximity, and a non-transactional approach to the community.
The Numbers Game Most Angels Underestimate
Adrian started angel investing more than a decade ago by deliberately cutting tiny checks. He assumed his picks would be bad, and the small checks were tuition.
“It’s like my version of college… if I’m going to lose all this money, I might as well make it as small a check as possible.”
He frames those early years through the lens of the secretary problem, a classic puzzle in math and decision theory: if the first candidate you interview seems amazing, do you hire them? You can’t, because you have nothing to compare against. You need volume to develop pattern recognition.
The same logic applies to startups. You have to invest, watch the stories play out, and feed your judgment with real data points. Adrian likes to remind people of the asymmetry that makes the whole game work.
“In angel investing, you can only lose 1x your money, but you can make like 10,000x your money… You become known for the things that hit. You’re never known for the things that didn’t work.”
There was one nuance worth flagging for newer angels: Adrian thinks the check size math has shifted since he started. Fifteen years ago, 25K was a reasonable starter check. Today, anything under 50 to 100K signals amateur hour and builds a bad reputation. His advice for someone with limited capital is counterintuitive. Don’t spread a small budget across twenty 5K checks. Do fewer, more meaningful ones, or join a firm where you can build pattern recognition without your own capital at risk.
Why Picking a Thematic Lane Is a Trap
A lot of investors pick a lane and go deep. Defense. Climate. Vertical SaaS. Adrian deliberately doesn’t.
“If I’m thematic and I say, I want a robotics company that does blah, the next person that comes in, now I’ve just got this huge cognitive bias, and I’m just going to probably choose like the wrong founder, the wrong team, the wrong whatever.”
Instead, he works bottom-up. Show him a person, show him an idea, and he’ll decide. His reasoning is grounded in pattern recognition from his own portfolio. The best companies in his book often ran directly against the prevailing thesis of their day.
“Remember, like, some of the world’s best companies were counter to the prevalent thesis at the time. Like, nobody was going around saying, oh my god, we need a new hotel. Turns out Airbnb was a good idea.”
The same logic applies to defense. A decade ago, nobody was telling investors that defense tech was where the money should go. Anduril proved otherwise.
The thematic trap is also why Adrian is skeptical of incubators. When you start with “I have an idea, now I’m looking for somebody to run it for me,” you tend to attract weak founders. Real founders bring their own conviction and their own problem they care about. Adrian would rather react to the people who come to him already obsessed with something.
Anchor to the Problem, Not the Solution
If anti-thematic investing is Adrian’s macro framework, the problem-versus-solution distinction is the micro one he uses to evaluate founders in the room.
“The interesting thing about solutions is they tend to change all the time. And the interesting thing about problems is they tend to be incredibly static.”
The transportation example he gave makes it concrete. A founder who says “I’m building scooters for cities” is in the wrong business the moment hoverboards arrive. A founder who says “I’m solving safe, clean, green urban transportation” picks up new technologies as they emerge and keeps moving toward the same destination.
When Adrian started Forward, his healthcare company, he framed the problem the same way. The goal was to reduce death and suffering on the planet. AI was going to come and reshape how that gets done, but the underlying problem wasn’t going anywhere for a long time.
This framing also reshapes how Adrian thinks about pivots, which is to say, he mostly doesn’t think they exist.
“I never know the difference between a pivot and just iterating… If you defined yourself as the solution, every time you change the solution, it seems dramatic and you don’t know what you’re doing and you’re pivoting. If you define yourself as the problem, we just call that iteration.”
The rule he summed up with was simple. Be stubborn on the vision, loose on the details.
The Two-Part Founder Test Adrian Got From Larry Page
After years of working as Larry Page’s right-hand man during the formation of Alphabet, Adrian asked Page how he defined a real entrepreneur. Two criteria came back.
The first is a creative one. Real entrepreneurs believe something no one else believes.
“Entrepreneurs have something they believe that no one else believes.”
This is the contrarian insight test. What does this founder know about their market, their technology, or their customer that the rest of the room doesn’t? What hill are they willing to die on?
The second criterion is behavioral. Real entrepreneurs walk through walls.
“They’ll just look at… the no that everyone gets, and everyone says, it’s a no, I guess we can’t do it. And they’ll just say, yeah, going to figure out how to do it anyway… As Elon likes to say, all laws are suggestions except the laws of physics.”
Adrian uses this lens in the room. The first thirty seconds of a pitch tell him a lot. If he can find obvious holes in the founder’s thesis that quickly, the founder hasn’t out-thought him on something that’s supposed to be their entire life’s work. The idea itself matters less than how thoroughly the founder has wrestled with it. Have they really thought it through? Do they have insight that the rest of the room doesn’t have? That’s what Adrian is grading on.
Adrian’s Real Edge Was Always Effort
Adrian didn’t have brand or dollars when he started angel investing. His competitive advantage was the thing every newer angel still has access to.
“Your competitive advantage is that you can put in effort, not that you have a bigger brand, not that you have bigger dollars… you’re on the ground, you know the people.”
The corollary he points to is the inverse correlation between success and availability. Marc Andreessen has a household name, but he’s not the one spending hours with a twenty-two-year-old founder working through the minutiae of getting something off the ground. That gap is where newer angels can actually compete.
The deeper version of this is how Adrian thinks about Silicon Valley itself. He treats the community as non-transactional and tries to help a lot of people, on the bet that the math works out over a long enough horizon.
“I don’t focus on how do I build my investing career. Instead, I say, how do I have an enormous amount of impact. Make the world a better place, build the right things, and you’ll be in the right room.”
The same principle surfaces in how he thinks about fundraising. Founders Fund’s Brian Singerman has put Adrian in the top 1% of fundraisers, and Adrian’s explanation for why is almost anti-climactic.
“If your differentiator is fundraising, you’re probably doing something wrong… be authentic and go work on amazing things that excite people for the world that they get to live in if it works, and you’ll probably be able to raise for that.”
Big visions raise money. Effort and proximity buy access. Doing both for long enough is how a portfolio like Adrian’s actually compounds.
The full conversation covered much more ground, including Adrian’s take on the OpenAI and Anthropic FDE consulting plays, how he approaches investing in around 100 different venture funds, the story of co-founding Seneca to fight wildfires with swarms of 500-pound drones that can reach a fire in two minutes, and the founder he passed on for being a jerk in a pitch meeting whose company is now worth about $15 billion. Watch the full interview above.
