Let’s begin with the good news. I’ve put 20 freelancers on cover already, which is over £5700 Gross Premium Written. This is 20 freelancers With Jack is helping build a bulletproof business. Yay!

Secondly, I’ve been shortlisted for two awards at the Digital Insurance Awards 2016. ‘Young Insurance’ and ‘The Rookie Award’. High fives all around.

The whole point of this blog, however, is to cover the challenges I face as well as triumphs. I’ve received a few emails from people complimenting me on my transparency, specifically when writing about building with Jack.

Now I’m into With Jack’s full second month of trading… and it’s hard. I’m realising just how challenging it is to market and sell insurance, especially as a newcomer to an established industry.

• People are used to instant quotes and cover. I have to manually process everything (for now)
• People expect cashback perks and financial incentives. I have a modest list of benefits
• Most people choose their provider based on price (a by-product of comparison sites). I don’t sell a cheap policy, so I’m missing out on sales. But I’m OK with that, I don’t want to sell cheap stuff—I want to sell a good policy from an underwriter with a reputation for paying claims /rant
• People are primed to buy insurance just once a year. I don’t have a database of renewals to tap into

Things have slowed down in my second full month of trading.

This is because I’ve burned through my ‘immediate network’. It’s a lame term to describe my friends in the industry, Twitter followers, email subscribers etc. Those who have watched as I’ve built With Jack and were ready to get on-board from the start (thanks!).

Now leads are generated from paid resources, ads and organic search. That’s fine, but these leads require more of the ‘hard sell’.

In hindsight, I’d have approached things differently to make post-launch easier. I wasn’t nearly as active in the build-up to launching With Jack as I could have been.

A Different Approach

If I could start all over again I’d do the following:

I wouldn’t think about what I’ll be selling down the line or the business I’m going to build. I’d pick a group I want to serve and spend a solid year focusing on that audience. No getting distracted with selling or developing a business—I’d channel all of my energy into helping, researching and speaking to that audience.

I’d start with people (freelancers)—not the idea (business insurance).

I’d go to conferences, attend meet-ups, blog regularly and participate in communities. I’d do only this for a whole year. No product to sell, no business to pitch. Just listen, research and grow.

I did some of these things to a degree, but lacked the consistency needed to produce the best results.

By the time With Jack had launched, I had 4000-odd Twitter followers (not all freelancers) and 200 email subscribers. There are many things I could have done to double, triple or quadruple these numbers, yet I focused on building my business instead of relationships.

That’s stupid—you can’t grow a business without relationships. Post-launch would be a little easier had I started with people.

Justin Jackson is a perfect example of starting with people. Justin didn’t launch a paid product for an entire year. Instead he focused on creating content, participating in communities and helping an audience of product people. Now he has a sizeable network ready to buy whatever he’s selling.

Hindsight is a powerful thing. I wish I’d set aside a year to research, help and build an audience of freelancers. What’s a year in the grand scheme of business?

Maybe you’re just starting out. Perhaps you don’t have an audience, idea or product yet. My advice would be to pick a group you know you can serve, and spend a solid 6-12 months researching, helping and growing that audience.

Don’t get distracted with selling, just focus on helping and serving the network you’re building.

Start with people.