Startup Events

Your default answer to any startup event is no. Decide that now so you don't have to fight the urge every time a Luma invite lands in your inbox.

Why Events Are So Tempting

There are multiple events you could reasonably attend every week. Founder meetups, pitch nights, investor dinners, accelerator demos. They're fun. You get to tell people what you're building. You get a free drink. You feel like part of the startup world.

That feeling is the trap. It's all the social rewards of progress without any of the actual progress.

The Real Cost of Saying Yes

It's never just the two hours at the event. Add travel. Add the mental context switch out of whatever deep work you were in. Add the time it takes to get back into flow afterward.

A two-hour evening event routinely costs you four or five hours of productive work. Could you have closed more leads if you'd stayed locked in and sent emails instead? Probably.

When You Actually Should Go

There are real reasons to attend events. Just fewer than you think.

You're new to the area and need to get connected

If you just moved and you're building a network from zero, a few well-chosen events can shortcut months of isolation. Go intentionally. Attend 3-4, meet people, follow up properly. Then stop. This isn't a permanent strategy.

Your customer is in the room

This is the big one. If you sell to startup founders, a founder meetup is a sales opportunity. Go. Sell. If you sell to doctors, go to medical conferences... not startup events. You want to be where your customers are, not where other founders are cheering you on.

Cross-reference this against your founder-led sales work. If the event puts you in front of qualified buyers, treat it like a sales call and go in with that mindset.

Pitch competitions

Pitch competitions are free entertainment... and you're the entertainment. There are a few legitimate reasons to do one:

• The audience is full of your target customers
• You're actively working on public speaking and need real reps
• You've been heads-down for weeks and want a structured excuse to articulate what you're building

Be honest about which of those actually applies. “It might be good for exposure” is not one of them.

Paid Events: Do the Math First

Some conferences and multi-day events are genuinely worth attending... but they come with a real price tag. Registration, flights, hotel, food. A legitimate industry conference can easily run $2,000-$4,000 all-in by the time you're back home.

That's not automatically disqualifying. But it does require actual math, not vibes.

You know your average deal size. You know your close rate. So figure out how many customers you need to close at that event just to break even on the cost of going.

The key question is whether your actual customers will be there in real numbers. Not “adjacent to your customers” or “people who might know your customers.” Your actual buyers, with budget, who have the problem you solve.

If the math pencils out and the audience is right, paid events can be some of the highest-leverage customer acquisition you'll do. You get face time, real conversations, and the ability to close deals on the spot. Go in with a goal... a specific number of conversations, demos, or closes... and treat it like a sales trip, not a vacation.

The “I'll Meet Investors” Justification

The most common bad reason founders give for going to events: “We're fundraising later this year and it'll be good to know investors before then.”

Here's the thing. Investors want to invest in great companies. They don't need to have met you at a cocktail party six months ago to take your meeting. Build a great company, get real traction, and they'll take the call. You don't need to work the room for a year hoping someone remembers your face.

If You Need a Break, Actually Take a Break

If you're burnt out and want a night out... fine. You're human. But think about what actually recharges you.

Is it a loud event with a hundred people you half-know? Or is it a real dinner with a close friend, a long walk, a night reading, or just doing nothing? Know what genuinely restores you and do that. Don't confuse “getting out of the house” with “recovering.”

If a specific event genuinely recharges you, go. But optimize for restoration... not for feeling like a founder.

The Workout Analogy

There are dozens of ways to exercise and dozens of outcomes you can optimize for. If your goal is building muscle, you do the specific exercises that build muscle... the ones that are hard, maybe uncomfortable, but that actually drive the result.

Battle ropes feel amazing. They look intense. They are not great for building muscle. If they help you enjoy the gym enough to show up and do the real work, fine. But if you fill your entire workout with fun-but-wrong exercises, you won't hit your goal.

Startup events are battle ropes. If going to one founder meetup a month keeps you motivated enough to grind the other 29 days, that's fine. But if you're going to three events a week and calling it networking... you're not building a company. You're doing battle ropes.

Know what your goal is. Plan your work to maximize outcomes. Be honest when the fun stuff isn't aligned with the actual goal but you're doing it anyway because it feels good.