Last week With Jack hit a huge milestone. My book of customers is now worth over a quarter of a million pounds. This isn’t an arbitrary number. There’s a reason it’s an important milestone.

Before launch—when all I had was an idea and a scrappy MVP with little traction—a string of insurers passed on working with me. Most of them said the same thing:

”You need existing business worth £250,000 for us to consider working with you.”

My brain asked the logical question, “How do I get to that figure if I don’t have any insurance products to sell?”. It was another obstacle that made breaking into an already challenging industry even more difficult. A chicken and egg situation. I can’t reach that figure without having an insurer’s products to sell, but they won’t give me their products to sell until I’ve reached that figure.

I also remember thinking, “Why won’t one person give me the opportunity to show them there’s nothing I want more than reaching this milestone and I’ll do whatever it takes to get there? I’ll put in the work”.

Maybe that sounds self-pitying, but it was a frustrating situation to be in. You know you’re capable, but nobody else is buying it.

At the time I was pre-revenue and had 0 customers, so reaching this goal seemed so far away. Almost impossible. But I put my head down, did the work, and with a small amount of progress each day I inched towards my goal of £250,000.

What does this mean for With Jack?

Getting here puts me in a stronger position to negotiate new products and prices, and hopefully even create unique products for my customers. I now have more of an advantage to execute on some of the bigger ideas I have.

Despite this being a figure I have been working towards for so long, I didn’t feel anything when it happened. I got a sale, I updated my spreadsheet, and I watched that number tick over the £250,000 threshold.

I waited for the emotion to kick in. Nothing. I thought about my Dad and how he’d feel. Nothing. I reflected on everything I’ve been through to get to this stage. Losing a parent and taking over the family business, driving it into the ground and spending years fighting to make this business happen. Nothing.

I went out for dinner, ordered two sparkling wines and waited for something to happen. Nothing.

My friends said I was in shock. Over a week has passed and I’ve had plenty of time to let this achievement sink in. Whilst I’ve certainly had a few, “this is cool” moments I haven’t really celebrated. Here’s why I think I’m finding it difficult to celebrate these tiny wins.

Tiny Wins Are Always Followed By Tiny Fires

I’ve been doing this long enough to know that triumphs are always closely followed by roadblocks. Within hours or days of celebrating a milestone, I’m going to be putting out a fire in another area of the business.

If I allowed my mood to be dictated by what’s happening in the business (which I used to do and it’s taken a long time to detach myself), emotionally I’d be up and down in a very unstable way. That’s not healthy.

Instead I try to keep my mood as flat-lined as best as I can.

Just 2 days after reaching £250,000, I had a record number of cancellations in one day. It was a coincidence and nothing to indicate this will happen regularly, but having just one cancellation can ruin my day. You can imagine how 4 made me feel…

This was followed by a few other negatives. Instead of letting it fill my head with the usual doubts, “I’m not cut out for this. I’m not doing a good job. I’m going to fail”, I acknowledged that I’m going to have these days every so often and we move forward.

It works both ways. I think the same attitude applies to my better days, too. I’m not saying this is a good thing. I’m saying controlling my mood is something I’ve had to do for my own sanity as a founder.

Thank U, Next

Even though this was a goal of mine for some time, it’s one of many goals and as a founder you’re constantly focused on the future and what’s next. This year I have several other, big goals to reach that feel a lot more tangible than this one. These include:

  • building our self service platform
  • launching new products
  • new features that will help you be a confident freelancer (sorry for vagueness)

I get more excited about product goals than I do about financial ones because they benefit my customers in a more direct way.

Reaching £250,000 does make the above easier to achieve. I’m likelier to get a delegated authority so I can quote and bind policies direct from my website. It should be easier to convince insurers to give me their products to sell, or even collaborate on creating products.

This moment should have been something to celebrate, yet my mind instantly diverted to “what’s next?”.

The Business Isn't Good Enough

This is a mental battle I face every day. With Jack is nowhere near where I want it to be. Not in terms of sign-ups or revenue, but products, features and value. Even little imperfections with the existing website drive me crazy.

The truth is, I’m embarrassed about where things are because I know they can be better. I got to £250,000 with manual processes and this certainly isn’t how I expected my business to look almost 3 years in.

By now I thought I’d have instant quotes and cover. A dashboard that users are onboarded to (we have some interesting ideas around this). An array of products and services that help to keep you in business.

Momentum with building and shipping is slow. This is an infuriating industry to build in if you want to move quickly, but not all of this is the fault of the industry’s red tape. Some of it is mine.

Then you have the natural desire to pit yourself against others. With all of my competition being VC-backed I assume they’re further ahead of me. This doesn’t really matter, but any success I experience is dampened with thoughts of, “It’s probably taken me longer to get here than everybody else”.

Am I Normal?

So much of being a founder is having the mental toughness to withstand the daily challenges you face. There are feelings of insecurity, vulnerability, instability and putting so much of yourself into something—and in a very public way—that could fail. It’s emotionally taxing.

I’m not speaking for every founder, but I do think we have the tendency to shut down in a lot of ways to get through it. And I think that’s what’s happened here. I am happy about this milestone, but I don’t feel the way I thought I’d feel because my mind is now focused on making With Jack better to get to the next £250,000.

P.S. Thanks to everyone who has been involved in helping me reach this number. No, really. Thank you.