I'm participating in the Autumn '24 cohort of Startup First Steps, a 13-week accelerator provided by Techscaler. During the months of September, October and November I'll be exploring the viability of an idea I've been noodling on and bringing it to market.

I'm excited to get back to my roots of:

1. transparency (sharing what I'm learning)
2. creativity (something the insurance industry has dulled)
3. collaboration (being a part of startup scene again)

I'm no stranger to accelerators. 7 years ago I applied to join Ignite. Whilst I didn't get accepted onto the programme because I wasn't "solving a big enough problem", I attended 4 or 5 of the offsites. I pretty much had the full accelerator experience… minus any investment!

At that point With Jack was post-launch with 100 customers but not yet profitable. Now I'm trudging towards £2,000,000 of policies sold and have tons of experience under my belt with customer development and marketing.

Why have I applied for another accelerator?

With Jack is in a good place, but I find myself working in the business instead of on it. Most of my day is spent on admin for our policyholders. Doing customer support, processing quotes, answering the phone. By the end of the day my brain is tired and I don't have the capability to explore my new idea. This gives me accountability.

My head is a mess. I have a general idea of what I want to build and I have years of data around this problem. But I just can't make sense of the muddle in my brain. The 1-1 mentorship calls and live classes will help me gain clarity.

It's free and I don't give up any equity. Applying to Techscaler was a no-brainer. It's funded by the Scottish government so there's no equity stake. You're required to attend at least 60% of the course, but there's no financial cost to me.

What's the idea?

Here's the thing. I love With Jack but other people don't. To reach product-market fit your target market must value your service. If they don't you'll find yourself in the predicament I'm in, which is:

• churn is high. Freelancers are happy to cancel their insurance in between contracts. This shows how little insurance is valued. They'll lose their history of insurance just to save £10 before they secure their next job
• nobody understands what I'm selling. For many people insurance is a box-ticking exercise. I had grand plans to educate freelancers with podcasts, video content and guides. Nobody cares enough to consume that content
• there are many objections to getting insured. "I've been freelancing for 10 years and have never had a problem with a client." When people are objecting to the product you're selling, you're never going to reach product-market fit

Remember, you don't have product-market fit if:

1. You aren’t growing
2. You have high churn
3. Your product is hard to sell
4. Customers don’t seem to care that much

I'm ticking 3 out of 4 of that checklist and honestly I'm really tired of pushing something that freelancers don't think they need. But all is not lost. As I've slowly built up my customer base I've become interested in solving a problem that keeps cropping up.

The problem of late or non-payment.

41% of clients pay freelancers late leading to an average of 20 days a year spent chasing late payments. Many aren't aware of their rights and will therefore do nothing.

I want to build a magic bullet to help freelancers get paid.

This is where Startup First Steps comes in. I am hoping that 8 years worth of payment data, 2000 existing customers to learn from, and access to skilled mentors is the recipe I need to figure out what to create.

From a With Jack perspective nothing will change. I still respect and believe in insurance. When it works it's the best thing in the world, but I'm painfully aware that I'm fighting a losing battle. It's time for me to follow my curiosity with solving a new problem.

If I don't do this then With Jack, in its current incarnation, will never find product-market fit.

Recent patterns have cemented my decision to do this. This week I've had more cancellations than new sign-ups. Whilst that's an irregular occurrence it's an indication of what I've outlined above. Churn is high on a hard to sell product that customers don't seem to care much about.

I've got my first mentorship meeting tomorrow, then the cohort kicks off on the 4th of September. I can't wait to get started!