Startup Ideas Are Like Waves

Hey y’all — do you ever wonder if you’re thinking too small?

A friend, who’s deciding whether to keep focusing on his 7-figure bootstrapped business or go after a venture-scale opportunity for the first time, reached out this week to ask me this question.

And, to be honest, I’m a good person to ask it to.

Since I left my own venture-backed company at the end of 2022, I’ve spent the last 3 years building a bootstrapped business.

A lot of people hear that and think it’s weird.

But we make our best decisions when we approach them from a place of abundance instead of looking for something new to latch onto right away.

I explained to my friend why that’s especially true for founders, and he said it was valuable, so this week I’m sharing it with you too…

Startup Ideas Are Like Waves

Founders tend to have a chip on their shoulder.

Maybe they were overlooked. I still remember not getting into the college I wanted to go to and then writing an email to the dean telling him he was making a mistake. Kind of cringe given how unimportant college ended up being, but I digress…

Maybe they had no connections.

Maybe something deeper is driving them.

Either way, this is one of the most beneficial traits a founder can have. It motivates them to go on building in the face of doubts, and to will their vision into existence. It creates relentlessness.

But it isn’t without its downsides.

Namely, it makes it hard for founders to be patient. And while that lack of patience can sometimes work to your advantage when you’re pushing ahead with growth, or your product, it can work against you when you’re trying to make big decisions that aren’t easy to reverse.

Our natural motors encourage us to swing from vine to vine, like Tarzan, even if we have a larger plan we’re executing against.

And, don’t get me wrong, things can work out that way. I went from zero connections → early Uber Eats → Airbnb Product Manager → founder whose startup raised a Series A from a16z + VC in 5 years, basically by just jumping at the highest leverage opportunities that were in front of me.

I’d even argue the startup world is set up to promote this — with all the capital on the hunt for unicorns, new markets emerge and get saturated quickly. It pays to be quick on the draw, even if it makes failure more likely.

But if we let that be the default all the time we risk two things: 1) missing something larger down the line and 2) jumping into something at the wrong time in our own lives.

It’s like relationships.

If you end a serious relationship, is it healthier to go start dating someone new right away, or take time to reflect and make a new plan for your future?

We can argue about that one, but I know my answer.

When I left Launch House at the start of 2023, basically everyone I knew expected me to go build a GPT wrapper and raise a bunch more money.

But I didn’t.

I went ahead writing this newsletter instead, and it has since evolved into a holdco.

That company has done millions in revenue now, but if I had gone out and raised venture for some new AI company instead who knows where things would be.

Am I supposed to regret that?

Is my friend supposed to regret not taking a venture shot now, if he decides it’s not the right time?

To be clear, I’d recommend every founder take on a venture-scale opportunity at least once.

You learn a ton in a short period of time, meet incredible and passionate people, and the upside is obviously amazing and motivating.

I haven’t ruled out building another venture-backed co at some point. I think I probably will in a few years, actually.

But timing doesn’t just matter in terms of whether a market is ready for your solution, it also matters for whether it’s the right time in your life to go after it.

Not taking that into account is the same type of energy first-time founders give off when they make everyone who they tell their (unproven, maybe even unbuilt) idea to sign an NDA.

It’s an intense scarcity mindset that leads to bad decisions.

And it misses something important:

Startup ideas are like waves crashing on the shore of the world.

If a wave looks good to surf, but you miss it, that’s ok — there’s always another one coming.

There will always be good startup ideas. Markets are mutating and emerging all the time. New problems emerge all the time and need to be solved. This world is a long way from perfect.

Even if you’re Tarzan, even if you have a chip on your shoulder to make your mark on the world, don’t let that make you operate from a place of scarcity.

Avoiding this trap lets you live your life with intention and find the right moment to do each thing you want to do.

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