If you are not embarrassed by the first version of your product, you've launched too late. — Reid Hoffman

Anybody in the start-up world will have heard the above quote. It makes a lot of sense, but it’s challenging to launch with an incomplete vision. After refining your idea for so long, launching with anything less than perfect doesn’t feel right.

You want to share the end result with the world and get it right from day one. It’s this danger that prevents people from shipping at all.

In August I launched With Jack. I wouldn’t say I was embarrassed by it—I was proud to get to the point of shipping because it had been a long slog. But I purposely launched with a bare bones business model.

With Jack started with just one insurance product.

Despite it not being the industry norm to offer only one type of cover, I’m glad I did. If I was to build another business I’d adopt the same one product approach. Below are the reasons why.

Avoid Making Assumptions By Gathering Data

Professional indemnity is the most popular cover amongst freelancers. Making this With Jack’s flagship product—and the one we’d launch with—was a no-brainer. I wouldn’t run any business without it.

The other key covers are:

  1. Public liability
  2. Employers’ liability
  3. Contents

I could guess what insurance my audience required, or I could let the data tell me.

After putting 60-odd freelancers on cover, buying patterns began to emerge. I can see that many require more cover than just professional indemnity.

22% also bought public liability. Some clients contractually require this if a contractor is working on-site.

17% insured their contents. This is a good move considering I was recently a victim of theft.

5% added employers’ liability to their policy. The lack of demand for this cover is because freelancers usually work solo. A digital agency will sometimes arrange their insurance via Jack, hence the request for this cover.

This data is influencing the business and what products I offer. Looking at these figures, it’s obvious my audience want more cover options.

Professional indemnity alone isn’t enough. Customers also want to protect their work tools (contents), themselves in case of causing third-party property damage (public liability), and their clients in case of injury (public liability).

This month we’re improving the quote system to include options to add public liability and contents insurance.

With only 5% buying employers’ liability, it doesn’t make sense to include this just yet. If With Jack starts attracting more digital agencies and teams, then it would be worth building it into the quote system.

I could have guessed what cover was relevant to my audience, but assumptions can be costly if you get them wrong. Instead I’m letting the data I’m gathering influence the direction of With Jack.


Professional indemnity is the most popular cover for freelancers. It made sense to launch with this product, then use data from sales to influence what other products we offered. We didn’t make assumptions. My customers told me what cover they needed.

Keep Costs Down

Launching with one product keeps development costs down. The more products I offer, the more options we’ll have to build into the quote system.

It’s not just that. We’d have to implement the extra functionality into the risk question form and my CRM tool. It all adds up.

I’m bootstrapping With Jack from money I earned doing wedding photography. I’m not a venture-backed start-up with deep pockets, so I have to be wary about expenditure.

One of my struggles with Jack has been knowing where to spend money. It made sense to launch with one product, earn money from that and invest it back into the business based on what the data / feedback was showing me.

Also, launching with one product has the benefit of getting to market quicker.


Launching with one product reduces the cost of development, design and other factors. This is crucial if you’re bootstrapping.

Do One Thing And Do It Well

With Jack’s focus is on building a better customer journey for freelancers. I didn’t want to get bogged down in making the system more complex.

I also wanted to avoid decision fatigue. Instead of overwhelming freelancers with different products, I wanted to give them the most popular cover for their type of work.

My goal is to use design and technology to remove barriers, making it simpler for freelancers to source the insurance they need. I wanted to say, “Hey, this product is ideal for your business and it’s easy to buy”.

Excuse the pun, but I don’t want to be a Jack of all trades. I want to offer a great product (professional indemnity) to a specific audience (freelance web designers and developers). Once I got that right, then I could expand.


Take one thing and own it. Specialise.

Launching without the bells and whistles of your competitors can make your business feel incomplete. I get that. I’m breaking into an industry where the big players have been established for decades (or in some cases over a hundred years).

Some of the other factors I’d like to have launched with:

  • Instant quotes and cover
  • Customer dashboard
  • Better benefits
  • Referral program

Not having these features hasn’t prevented people from using With Jack to arrange their insurance. Instead I was able to launch quickly, start generating income and use feedback to influence the direction of the business.

That’s why you should launch with one product.