Issue No. 15

Solopreneur or Cofounder

For years I took a solo approach, but I've come to a new conclusion on co-founders. Here's how I thought through the choice.

Reading Time: 3 min

Solopreneur or Cofounder

Source: DALLE, told to extract key phrases from this newsletter, create a prompt and using the style illustrative, colorful, futuristic create an image.

This week’s main topic is how I decided go stop being a solopreneur and chose a co-founder.

What you’ll read this week:

  • My day job was acquired
  • My refocus on Interweave
  • How I thought through and chose a cofounder


🔹 My day job was acquired

If you follow me on Twitter (err X), you may know that the company I was the startup CTO for was acquired. You can read about that here.

For 10 years I was the startup CTO of a cybersecurity company creating a new space.

I know from first hand how startups are hard.

I’m still unpacking the lessons learned (the link above is a thread and shares the main ones)

But one of the biggest one I learned.

When doing a startup it’s easier to pivot a category than it is to make one.

I’ll be talking about that more in the next newsletter.

🔹 My refocus on Interweave

If you’ve followed along for a bit I had been working on a startup called Interweave. For day-job reasons I had temporarily shelved it to work on something smaller, but even smaller didn’t work.

The goal of Interweave is to be the AI copilot for product managers.

A few things have changed since my idea for Interweave. And while I’m not floating in free time (since I’m the VP of Product Management at the acquiring company) the time is right for Interweave.

It’s currently a night’s and weekend endeavor, but it’ll be launching late this fall.

My cofounder and I are currently working to figure out what’s needed for an MVP and what can wait. (See I follow my own advise.)

I’ll be sharing a lot of the journey about Interweave in this newsletter that I won’t be sharing on X. I hope you enjoy.

Which brings me to…

🔹 How I thought through and chose to have a cofounder

In the past the idea of a co-founder wasn’t appealing to me.

Being the “master of my domain” was more appealing. But frankly when I started thinking about it three things kept coming to mind.

1. Going solo is lonely

Startups are hard.

And while my wife is amazing and get’s what I’m doing. She’s not “in the trenches” debating code, partnerships, sales and marketing, and the 100 other things a startup needs with me.

When push comes to shove I’d rather have someone else rowing with me.


2. Empirically startups grow faster with a founder

I recently saw an interesting stat in 2022 State of Independent SaaS report by Microconf.

It shows that startups with more than one founder grow faster. It’s not a huge amount, only 7%. But given how many startups fail, why not pile on advantages?

And really, if I’m going through all this to build a company…

3. I want this to be a company not a solo project

As I started imagining what Interweave would be I realized it was always with people.

I want to do this journey with people, not just by myself.

Many startups begin with a solo founder and then hire. There’s nothing wrong with that. But I realized, why not start out that way on day one?

As simple as that

So there you have it. Pretty simply really.

As for how I picked someone? That was simple as well.

I met my cofounder a bit over a year ago when I hired him as a senior software engineer. I’ve had a chance to know his work, become friends with him, meet his family, and see how on many fronts (other than software) we’re compatible.

As I started talking about Interweave he expressed interest in working on it and in wanting to have always started something.

Given how I’ve gotten to know him as a quality person it became obvious he’d be a great person to build this with.

We’re still hammering out equity, etc. But to be clear, he’s not a hired employee, he’s putting in as much as I am in this.

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