Can A Visionary Be A Solo Founder?

I was at a co-working event two weeks ago, in the middle of explaining my vision for Table for One, when a woman, across from me, interrupted to say:

“I don’t think I can ever be a solo founder.”

I’ve had a lot of conversations about solo founding and nobody has ever said this to me so plainly. I mean… everyone wants to believe that they could do it by themselves.

So I asked her why she thought that.

“I am a visionary,” she said. “Given how chaotic and spontaneous I am, I could never sustain a startup alone!”

It was a fair point and I didn’t have an answer for her then. But I do now.

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Before I get into this one, I wanted to share that I’m hosting a Roast My Pitch event. 1 hour. 5 presentations. Your fellow pitchers are going to be your competitors and your judges. This is a completely low stakes way to practice your pitch. And lurkers are welcome too!

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The Benefit Of Being A Visionary

The best thing about being a visionary is that you can be at the cusp of a market that other people won’t see for years.

You connect things that don’t obviously belong together.

Your tolerance for risk is pretty high. When data proves an assumption wrong, you can creatively redesign the strategy, business model, and basically everything without fear.

You also have a relentless level of optimism that comes in handy when two years into being the founder, the novelty has worn off, the numbers haven’t moved as much lately, and you still have to handle the unglamorous work.

Where It Breaks

But I see her point. I understand exactly what she was worried about.

The Execution Gap: When you are so focused on the five-year version of your startup, the boring, daily work, can get a little sidetracked.

Nobody To Say No: You generate ideas faster than the team can execute them, and with no co-founder to stop you, you pivot every few weeks. This results in a product that is either a Frankenstein version of what you wanted to build or is nowhere close to the problem you started with.

Too Much In Love With Your Idea: The high risk tolerance and deep optimism can sometimes combine into a bit of stubbornness. You fall for your own idea so completely that you stop hearing what the users are telling you. You see only what you want to see and build something nobody asked for.

Scaling Before Required: The moment you have capital, you try to scale your startup assuming it has already become the startup of your vision. Hiring, marketing, office space, infrastructure. All of these might start to seem like necessary expenses but you don’t even have product market fit.

So the real question is: How can you keep the five-year vision in your head without letting it eat the weeks in front of you?

The Locked Tiles

When I interviewed Jen Yip for the Unfair Advantage piece to learn how she bootstrapped Lunch Money for seven years, she described building the product like looking at a video game map. She wanted to only see the tiles that were already unlocked while the rest of the map stayed dark until she had enough “experience points” to unlock it.

She wasn’t planning ten moves out. She was just looking at the next one.

And this, in my opinion, is the best advice for a visionary. In fact, I believe, this is exactly how every early-stage founder should think. Obviously you should know where you are going and you need the big picture. But you should never fixate on it.

Before you have concrete evidence that people want what you are building, you simply can’t operate off what you want the company to look like a year from now. Because you don’t actually know whether you’ll be there in a year. Your job, your only job, is to survive the next month.

So… Can A Visionary Be A Solo Founder?

I believe all founders have to be a bit visionary.

And I have hit every one of the issues on some level. I’ve been fixated on the 5 year vision. I have radically changed paths. And I have spent money on things I shouldn’t have when the only job in front of me was finding product-market fit.

So yes, I do think that a visionary can be a solo founder, as long as they know where they leak and they plug it with other people or maybe even AI. Three things that can close those gaps.

Hire Your Opposite

Your first hire should be the person who can turn your chaos into coherence. You want someone detail-oriented and priority-driven, the kind of person who has probably already built their own productivity system.

They own timelines and project management. They hold you to the deadline you set back when you were feeling ambitious.

At Shezaar, my first hire was an engineer and he was as detail-oriented as they come. Every week, we had a standing meeting to discuss product feedback and I used to bombard him with insane amounts of information. He would take a few hours and then come back to me with a proper structure.

If you can’t afford someone like that yet, you can always build a version of them. I have a chief of staff now that I built with Claude. Throughout the day I send it voice notes, whatever’s in my head at the time, and it turns them into organized tasks and keeps track of what I still owe people.

Find Advisors Who Are Blunt

You want advisors who have either been founders themselves or know execution well enough to spot when you are drifting. And you have to give them the explicit permission to be blunt otherwise people tend to be polite.

I had three people who did this for me and those conversations saved me from a lot of mistakes.

Build Your Village

The case for a co-founder is that there’s one person on the team who can tell you no and who’s genuinely incentivized to do it. None of your employees will. Advisors sometimes might, if you’ve given them room but you can’t call on them often. So most days there’s nobody whose interests are tied to stopping you.

The closest replacement I have seen are other founders who are roughly at your stage.

Right before my first pitch competition, I met two female founders who were gearing up to pitch too. So we formed a little group. We met on Fridays and practiced with each other. We kept the ritual going even after the pitches were over. Some days we would just rant about our day. On others we would bring the problems we were stuck on and discuss the solutions.

That group became the informal board I never appointed.

So if you are a solo founder, I urge you to find this. Find the people you can ask stupid questions. The ones who can tell you that you are about to make a mistake because they have made it themselves 3 weeks ago. The ones who share their wins and their losses with you.

Having people like that to rely on is a dream, and it’s why I am building Table for One.

Anybody can be a solo founder now. You don’t have to fit in a box to be one. All you have to do is understand your weaknesses and plan for them.

What do you think?

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