Why Some Founders Keep Landing the Right Rooms, People, and Timing (And How to Replicate It)
How founders stop waiting for the right moment and start engineering it
I write for founders and executives navigating the inner game of scaling. Every week you’ll get one core idea, one tiny experiment, or one founder insight you can apply now.
This issue was inspired by my recent conversation with Haris Butt, product leader, former VP of Product and Design at ClickUp, and founder. If you haven’t listened to that episode yet, it’s worth your time.
What if the thing you called luck was actually a system you built — without ever realizing it?
Think about the best opportunity you’ve ever landed. Before you read on, sit with that for a moment.
The Belief Worth Challenging
Most founders have a complicated relationship with luck.
On one hand, they’ve been told it doesn’t exist: that outcomes are a direct result of work, skill, and execution. On the other, they’ve watched people with worse ideas and thinner resumes land better outcomes, and they know something else is in play.
So the working belief tends to land somewhere in the middle: luck exists, but it’s random. Some people have it. Some don’t. You can hustle, but you can’t manufacture it.
That framing is the problem.
Luck isn’t random. And waiting for it to find you, rather than building the conditions that make it likely, is one of the quieter ways founders stall. They keep executing, keep grinding, keep doing the visible things. But they’re not moving into the environments where luck concentrates. They’re not shortening the distance between themselves and the right moment. And when something doesn’t break their way, they chalk it up to probability rather than design.
What It Actually Looks Like
Haris Butt will tell you, without hesitation, that his career has been largely lucky. Pre-med student turned product designer. Barista to VP of Product at ClickUp. Reluctant job applicant who famously never applied for a job after his first one.
But spend an hour with him and a different picture emerges.
Haris didn’t wait for opportunities to find him, he systematically inserted himself into proximity with the people and problems that excited him. When he wanted to work somewhere, he reached out directly and told them exactly why. When he got fired from his first job in San Francisco, his response wasn’t to update his resume and start applying. It was to ask a simpler question: what do I want to learn next? That question led him to Square, which led him to Detour, which led him to Notion, to ClickUp, to his own company.
“You got to learn how to get good at finding luck. It doesn’t find you at all.”
The mechanics he describes are specific. When he wanted to work with someone, he’d reach out, tell them what excited him about what they were building, and explain how he thought he could contribute, before any job had been posted. The effect, as he puts it, was moving himself from a pool of thousands to a pool of ten overnight.
“That’s how you create luck. Sometimes the luck is: do they notice you? Do they open the message?”
He also talks about reducing the cost of the jump. Not by pretending the risk isn’t real, but by being honest about the worst case and deciding he could live with it. “What’s the worst that can happen?” is less a rhetorical question for him than a genuine filter. When the worst case was survivable, he moved. He’d been doing it long enough that it became a repeatable process rather than a leap of faith each time.
What ties all of it together is something he said almost in passing: “It becomes easier for luck to find you when you start listening to the right things.” He wasn’t talking about mindset. He was talking about signal, being embedded in the right conversations, the right rooms, the right questions, so that when something worth noticing surfaces, you’re close enough to notice it.
None of it was a grand strategy. Most of it looked, from the outside, like impulsiveness or good fortune. But each move followed a consistent internal logic: get close to what excites you, reduce the friction to jumping, and make yourself easy to find for the people who are building what you want to be part of.
If this resonates, forward it to a founder who’s waiting for the right opportunity rather than engineering the conditions for it.
A version of this has played out in my own work too.
For years, I’ve made a habit of reaching out to people I want to learn from, with no agenda, no ask, just genuine curiosity about what they’re building and how they think. Some of those conversations led to clients. Some became podcast guests, workshop collaborations, or ongoing partnerships with communities I didn’t know existed when I sent the first message. Others led to nothing professionally, but became some of my closest friendships.
None of it felt like a system while I was doing it. It felt like staying curious. But looking back, it was the single most consistent thing I did to put myself in the path of opportunity. Not a strategy. A practice.
That’s the thing about building the conditions for luck, it rarely looks like luck when you’re doing it.
What the Research Actually Shows
Weak ties, not talent, drive breakthrough opportunities
The people who already know you well tend to know what you know. It’s the people at the edges of your network, loose connections outside your immediate circle, who carry information, introductions, and opportunities you don't have access to yet.¹ Founders who are only deepening existing relationships while staying inside existing rooms are, structurally, reducing their surface area for luck. This remains one of the most cited findings in sociology.
Proactive behavior predicts outcomes more than circumstances do.
People who take initiative to shape their environments, rather than adapting to them, achieve better career outcomes across industries and contexts.² This isn’t about confidence or charisma. It’s about a default orientation: moving toward the conditions you want rather than waiting for them to materialize. Haris’s career is a longitudinal case study in this exact mechanism.
Building the Conditions for Luck
The goal here isn’t a networking playbook or a hustle mandate. It’s a more deliberate relationship with how opportunity actually moves.
Ask what you want to learn, not what you want to achieve.
Haris’s recurring move when a door closed wasn’t to optimize his resume, it was to ask what he wanted to learn next. That question has a different quality to it. It’s honest about uncertainty, energizing rather than pressuring, and it naturally points toward the people and environments where the answer lives. Watch for this in yourself: if the question feels heavy, you’re probably asking it wrong. Founders oriented toward learning tend to move into higher-luck environments faster than those optimizing for a specific outcome.
Get close to what excites you before there’s a formal reason to.
The best opportunities Haris landed came before a job was posted, before a partnership was formalized, before anyone was officially looking. He was already in the room, or already in someone’s inbox when the moment arrived. The equivalent for a founder isn’t just warm intros and conference attendance. It’s being known, in the communities and conversations that matter to you, for a specific point of view. Generalists wait for luck. People with a distinct perspective attract it.
Shrink the pool. Don’t expand the blast radius.
The temptation when looking for opportunity is to cast wide: more applications, more outreach, more visibility. Haris’s insight runs the other direction. A deeply specific, well-researched message to ten people you genuinely want to work with or learn from outperforms a generic message to a thousand. Specificity signals seriousness. And it moves you from a pool of thousands to a pool of ten, which changes the math on luck entirely. The founders who complain about low response rates are almost always sending the wrong message, not too few of them.
Price the downside honestly. Then make the call.
The friction that keeps most founders from making the moves that would create luck isn’t laziness, it’s an unexamined fear of the worst case. Haris’s practice of asking “what’s the worst that can happen?” isn’t bravado. It’s a real evaluation. When the worst case is survivable, the calculus changes. Most of the time, it is. The move most founders are avoiding isn’t dangerous. It’s just unfamiliar.
The Bigger Picture
There’s a version of the luck conversation that stays safely abstract: the right mindset, the right energy, the right moment. Haris doesn’t tell that story.
What he describes is a set of repeatable moves that, compounded over a career, created the conditions for things to break well. Not because the universe was benevolent. Not because he was uniquely talented (which he is). But because he stayed curious, stayed close to the people and problems that mattered to him, and kept reducing the activation energy required to make the next jump.
“As much as I’d like to say that all of this was intentional, I think it was just dumb luck for the most part.”
He says this, and he means it. But dumb luck doesn’t land someone at Square, then Detour, then Notion, then ClickUp, then their own company, but consistently learning, consistently building, consistently finding the next thing worth jumping toward.
That’s not luck finding him. That’s a founder who built the conditions so well that luck had nowhere else to go.
Founder Circle
The founders who engineer luck best aren’t doing it alone.
They’re in rooms where the right questions get asked: where focus sharpens, hard decisions get real air, and the inner work gets done alongside the operational work.
I work with a small group of founders who want three things:
Clarity on what actually moves the needle, not just busyness.
A place to think through hard decisions, where to focus, which rooms to be in, how to make the jump when the timing feels wrong — without having to perform confidence you don’t feel.
A peer group that gets it: other founders doing the inner work alongside the operational work.
Our next circle meets soon. Grab your spot here:
P.S. Tell me: what’s the last move you made that felt like luck and what had you actually done to put yourself in that position? I read every response.
If you want to go deeper to check out the references used in our research:
¹ Granovetter, M.S. “The Strength of Weak Ties,” American Journal of Sociology, 1973
² Crant, J.M. “Proactive Behavior in Organizations,” Journal of Organizational Behavior, 2000
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