At some point this year I started considering investment. The initial build of With Jack was funded with my own money (money I’d earned photographing weddings at the weekend).

I liked the idea of bootstrapping. The investment scene mystified and intimidated me, but bootstrapping had its downsides. It meant taking short cuts, iterating slowly and being limited with marketing experiments.

Taking Short Cuts

A lot of With Jack’s tech was built on a shoestring budget. Some of it’s a quick fix to get the job done. It’s fine at the moment with just me working on Jack, but once I grow it’ll get complicated and have to be reconsidered.

Iterating Slowly

I don’t have the budget to match my ideas. That’s frustrating. When bootstrapping you have to ruthlessly prioritise. You don’t have the capital to explore every idea. Even the process of iterating on one feature is slow. I’ve focused on the onboarding process, but there are features for existing customers I’d love to build.

Limited With Marketing Experiments

Most of With Jack’s customers have come from organic search, word of mouth and referrals. Not having a pot of cash to dip into means being limited with marketing. I’d like to experiment with conference and podcast sponsorship, but it isn’t cheap.

My numbers have been consistent from day one. 10-12 sign-ups a month. Retaining 83% of customers come renewal. But I hit a plateau. I didn’t have the capital to reach more people and With Jack’s product wasn’t evolving as quickly as I’d like.

That’s when I applied to join an accelerator. A £25,000 cash injection with connections to the investment scene, meaning there was the option to raise more if needed.

(At the crux of it, I was excited to tap into the mentor’s experience and meet like-minded people. That was my priority and the accelerator delivered on that front.)

Truthfully, I was never fully committed to the idea of investment. Even during the application process I wasn’t sure if it was right for me. It was more of a, “Let’s dip my toe in and see what happens” vibe. But before I knew it, I had drank the Kool-Aid and got sucked into startup mentality.

“A lifestyle business isn’t good enough.”

“You have to think bigger and be more ambitious.”

“Not getting funding means you’re not good enough.”

“You need to disrupt an existing business model.”

These were just a few of my thoughts.

As well as the cash injection I wanted validation. Getting investment was like somebody saying, “I believe you can do this”. After years of insurers rejecting working with me, my fragile ego craved validation.

But I didn’t get investment.

After the initial disappointment I felt OK about it. No, really. I trust the accelerator. I respect the people who made that decision. I understand why they passed on investing. It wasn’t right for them… and in hindsight it wasn’t right for me.

Side note: You may be wondering why I didn’t get investment. I think it was down to being a solo founder, not solving a big enough problem and being unclear on where the £25,000 would go. I’m sure there were other factors, but these are the obvious obstacles.

I had no desire to apply for other accelerators. I’d been on the fence about investment, so when it fell through my thoughts turned back to bootstrapping.

Why I'm Bootstrapping

I realised I’d prefer turning my attention towards getting 1000 true fans.

I realised the funding process isn’t for me. I’ve spoken to my friend, Cally, at Mallzee about this (they’ve raised over £4 million). Taking time away from work and exhaustive travel wouldn’t make me happy. I like working from Glasgow, having my routine and hanging out with my dog.

I realised I want to figure things out in my own time and retain control, instead of having strings attached and scaling quickly to satisfy investors.

I realised I want to focus solely on my customers. Not on VC’s or getting wrapped up in the insurtech bubble. To be laser-focused on the people that will make With Jack profitable.

Above all else, I realised I didn’t want to disrupt an industry. I want to pick a small corner of the web that I can call mine and build something great.

That’s it.

What Do I Want To Achieve?

Building something profitable and of value for thousands of happy customers.

I still have an internal struggle. I wonder if I’m taking the easier option (although nothing about this journey has been easy). I feel bad about myself for not maxing out my ambition. Especially as—with no family or children—I’m in a position where I can take more risks.

But then I go back to what success means to me.

Success is crawling into my bed at the end of the day feeling creatively satisfied and challenged. Currently, I feel that way most days.