I first heard this term on Justin Jackson’s blog. I’m not 100% sure if I’ve understood it correctly, but my interpretation is that company/founder fit is ensuring the business you build fits the kind of life you want to live.

As Justin says, “If you want to get to $1 million in sales, you’re going to need to build a company. Does being a boss fit into your dream?”.

Jarrod, The PE Geek, created a company around live events “because I wanted to travel and I love to talk and teach directly with people”. A company like Jarrod’s isn’t ideal for you if you’re an introvert with travel anxiety. That’s (my interpretation of) the idea behind company/founder fit.

Company/founder fit popped into my head again when reading Will It Fly?, Pat Flynn’s book on idea validation.

I got a lot out of Pat’s book despite being post-launch and having already validated With Jack. There was a particular exercise early in the book that helped me understand what kind of company I want to build, but more on that later.

First, let’s back up a bit.

With Jack is self-funded. I did briefly toy with investment when I unsuccessfully applied to join an accelerator. I’ve also had some recent interest from investors.

Instead I took a different route. I built With Jack with money I’d earned from freelance photography (this money has dried up now and I quit photography in 2018). This helped fund a lot of the initial design and developments costs.

But every so often I find myself thinking about investment. Sometimes I feel myself being pulled in that direction. There are lots of people who have tried to convince me it’s the best route to take. “With Jack is going well, but it could be doing so much better! Don’t you want to think bigger and go after the whole market?”

I never know how to answer that. I’ve always struggled to define what kind of business I want to build. But I do know a few things;

  1. My gut feels more comfortable with bootstrapping as opposed to taking someone else’s money (however, feeling comfortable isn’t an indicator you’re doing the right thing. I often see it as a negative. If something makes me feel uncomfortable, I’ll do it to push myself out of my comfort zone)
  2. My values align more with bootstrapped companies than VC-backed companies. I’m not here to build a Unicorn and make a quick exit. Perhaps foolishly, I still see myself doing this in 10+ years
  3. I want to focus strictly on pleasing customers—not investors

However, maybe investment would be the right route for With Jack. After all, my mission is to help every freelancer be a confident freelancer. There are 2,000,000 in the UK and to get in front of as many of them as possible I’d need money. Way more money than I currently make or have at my disposal.

This question of taking investment and thinking bigger—and deciding on the kind of company I want to build—has always been something I’ve struggled with. Spiritually I feel more aligned with the bootstrapped ethos, but there are millions of freelancers I want to help and having money would make that mission more achievable.

Back to Pat’s book.

This exercise encouraged me to write down 4 areas of my life that are important to me and to think to the future about how these areas of my life would look in an ‘ideal world’ scenario.

Mine were business, health, finances and leisure. Maybe yours would include family, travel, career etc. Whatever is important to you.

Here’s a snapshot into mine. Remember, this is an ideal world scenario.


  • Customers get a lot of value from using our service and With Jack has made the lives easier for millions of freelancers.
  • We’ve expanded globally so we can help more freelancers.
  • Some of my friends are employed by the business.
  • We have a great culture at the office and it’s a happy environment to work.
  • The business is self-funded so I can focus on the best outcome for customers and don’t have to answer to investors.


  • I have the time to train regularly.
  • I’m running a handful of half marathons a year.
  • My deadlift PB has exceeded 100KG.
  • I’ve adopted a vegetarian diet.


  • I support my family with the business.
  • Money is no longer a worry.
  • I give back to charity and use my wealth to contribute to making the world a better place.
  • I own a holiday home abroad.


  • I travel freely and regularly.
  • I have time to play video games.
  • When I’m not travelling I spend every day with my dog.
  • I have the freedom over my routine to do what I like whenever I want.

Two of the key themes I picked up on when doing this exercise were freedom and flexibility. These are important to me.

Traveling freely and having control over my routine doesn’t involve getting on planes to secure the next round of funding before cash flow bleeds dry. That’s my idea of hell.

Building the business on my own terms—and having control over the direction I take it in—was one of my ideal outcomes. Because freelance premiums are small and the market isn’t very large, investors may try to push me down another avenue.

Some of these ideal outcomes seem ambitious as a bootstrapper. One of them is to expand globally so we can help freelancers in Europe and beyond. Again, money would make expansion easier but I don’t need VC money to go global. Fortunately, With Jack is already profitable!

I spent 30 minutes of my train ride to Nottingham doing this exercise and it was time well spent. It gave me the clarity that I’ve been missing over what kind of life I want to live and how With Jack fits into that.

Building a business is all consuming and so much of your identity becomes wrapped up in it. Especially in the early days. But life isn’t just about business, and therefore it’s important to ensure the company you’re creating fits the kind of life you want to live. You have to have company/founder fit.

Just after doing this exercise I read a fascinating blog post from Cheri Baker called Patreon, Venture Capital, and the Loss of the Win-Win. It really hit home that building a VC-backed company isn’t for me.

“Here we have a business that people like, offering a service we value, and it enables small businesses to grow, benefiting many people. That’s how business should work. But because Patreon took in a shit-ton of VC money, they don’t have the freedom to stay in that business. They have to chase more money, a lot more, just to stay afloat.”

This blog post isn’t to bash VC. It’s the right avenue for some people and when it does work the impact can be insane! But for me I want to build a company that people like and value, and have the freedom to take it in the direction I want—which is the one that’s best for freelancers.