Trillion Dollar Trigger: The Upside of Founder Envy

Three years ago, I met a founder who reminded me of myself at 25, driven, ambitious, full of ideas. The difference was, by that age he had already accomplished more than I had. Instead of seeing that as inspiring, I let my insecurities get in the way. I compared his success to my own, and in doing so, I walked away from the opportunity and passed on the deal.

What I’ve realized since is that this wasn’t just about passing on one founder. It was about the mindset I was bringing into the room. A scarcity mindset of measuring myself against others, making me blind to opportunities that were right in front of me. A mindset that cost me the chance to invest in companies that went on to become unicorns.

But it also gave me something else: a wake-up call. This is the story of how I began to recognize my emotional triggers, and how that awareness is shaping me into a more grounded, self-aware, and confident investor

Three Stories I Still Tell Myself at 3 AM

The One “Who Knew Too Much”

Still a teenager. Defense tech. Described building autonomous military systems like it was as simple as shipping an app. No hedging. No “if we can figure out.” Just: here’s what we’re building, here’s when it’ll be done.

I sat there thinking: Nobody that young can possibly make something this hard sound this easy.

What I was really thinking: I’ve never believed anything could be easy.

We passed. The pre-seed was under $15M. His company is approaching a billion now.

The One “Who Didn’t Try”

Met him in South America while on vacation. The whole group felt like retired founders and people who’d given up on being ambitious. Late nights that turned into early mornings. Stories about past wins between rounds of drinks. Everyone seemed caught in a loop of self-indulgence, content to coast on what they’d already built.

He was there too. Laughing. Relaxed. Present.

“What’s someone building a ‘real’ company doing here?” I thought. I judged him for being in that group. For seeming like he lacked urgency and was hanging around with people that didn’t seem to up to big things.

What I couldn’t admit to myself — I was a part of this group as well and actively participating. And maybe I was terrified of what that said about me — did I have urgency?

We never followed up. He offered me a spot in the round. I passed. I could have been one of his first investors. The company is worth well over a billion now.

The One “Who Didn’t Need Me”

B2B SaaS founder. Our entire meeting was him showing me his pipeline. Customer logos. Revenue multiples. Next quarter’s hiring plan. Didn’t ask for my advice once.

“Too transactional,” I wrote in our notes. Translation: “My ego needs founders who need me.”

They’re worth over $2 billion now. He still hasn’t asked for my advice.

The Expensive Truth

The founders who trigger us most might be showing us exactly what we need to see. Not about them, but about us; they are a mirror for us.

That arrogance you can’t stand? Might be confidence you’ve never given yourself permission to feel.

That casual approach that seems reckless? Might be someone who’s figured out what you haven’t — that you can build a billion-dollar company and still have a life.

That founder who doesn’t need your wisdom? Might be exactly the founder who’ll succeed without you.

The Thing About Mirrors

You know that feeling when someone walks into the room and you immediately feel small? Not because they’re trying to intimidate you, but because their presence reminds you of everything you are not. Or worse — everything you could have been.

When I feel emotionally triggered in this way, I have founded myself dressing it up in professional language. “Not coachable.” “Overconfident.” “Can’t see them recruiting a world-class team.” “Something feels off.” But if I’m honest, what I’m often saying is: “This person makes me uncomfortable.”

The thing is, that discomfort can be expensive. Especially when the real reason they make me uncomfortable is because they are holding up a mirror to my own insecurities or to the limiting beliefs that I have about myself.

The Gift and the Practice

I have turned this into an actual investment thesis. When someone triggers that knee-jerk “no,” I stop. I ask myself:

What am I really rejecting here?

Sometimes it’s genuinely a bad fit. But sometimes, and this is the expensive part, I’m rejecting the parts of them I haven’t accepted in myself.

At Long Journey, our mission is to be a founder’s second believer. For this to be true, we have to believe in our own capacity to stand next to greatness. To recognize it. To know we belong there, fanning that flame.

But how can I stand next to greatness if I’m triggered by it? How can I fan a flame when part of me wants to run from the heat?

So now I’ve learned to sit with discomfort. When a founder triggers something in me now, I don’t run. I pause and I perk up. . I get curious about why I have "founder envy.” I examine what’s really happening inside myself.

This information is a gift. My emotional reaction is a reminder that there is a hidden lesson and insight behind a belief that I have about myself and is most likely an opportunity for me to grow (rather than the founder). Furthermore, I wonder if this is a sign that we should actually invest.

I’ve also started sharing this with my partners. After a triggering meeting, I’ll ask them: “Am I passing because of the business, or because this person reminds me of something I don’t like about myself or am insecure about?” Our team has gotten good at spotting when we are reacting to a mirror rather than reality.

There are now times when the founder who initially triggered me or rubbed me the wrong way, becomes the one I fight hardest to win.

The Mirror Test

I remember when Augustus Doricko from Rainmaker came on my Zoom and said, with complete certainty, that he was going to change the weather. Make it rain on demand. Control what humans have prayed and danced for since the beginning of agriculture.

The confidence. The ambition. This guy talking about what was possible to help society with clouds. I felt physically uncomfortable. Who did he think he was? The sheer audacity of it triggered every insecurity I had about thinking too small.

But something made me pause. Maybe it was the way he laid out the plan in such a matter-of-fact way. But really, it was recognizing I was triggered. That moment of awareness—of catching myself in my own insecurity—allowed me to see the sheer brilliance in his plan.

I invested. Rainmaker is now the largest cloud seeding operation in the country.

The best investments I've made have been in founders who scared me a little. Who made me question my own limitations. Who showed me what was possible when you stopped apologizing for knowing what you know.