My Journey To 250 Customers

My Journey To 250 Customers

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Somebody I follow on Twitter recently launched a new product. Within 2 months he had tweeted about hitting $10,000 MRR. Wow. I’m 1.5 years into building With Jack and nowhere near that figure.

For a minute I felt disheartened. Maybe I’m not good enough. Maybe I’m not cut out for this.

I’m putting a lot of work in and still at a place where the money I’m earning doesn’t reflect the hours I’m investing. (I’m OK with that. I fully expect the first few years of starting a business to look like this).

I started comparing my success to his and felt like a failure.

Then I remembered an important detail. This person has a huge existing audience to launch to. He also has a team of people working on it, existing capital and has already built a successful business in that space. Most of us don’t have that audience or leverage, so why was I comparing my success to his?

This got me thinking about my own journey. It’s been slow, organic and probably how it looks for a lot of people (no overnight success, no large audience to leverage).

With Jack has grown recently. I’m hitting monthly targets in 8 days. Just two months ago I was celebrating 200 customers. Now I’m at 250!

Every week I have to pinch myself because I’m signing up more customers. Is this really happening? Is the growth a fluke? It’s taken 1.5 years of work just to get to the “it’s starting to look like a real business” stage.

I’ve built and launched a lot of projects over the years. SaaS apps, podcasts, online courses… I used to expect big things from launches. “This is it. This is the idea that’s going to take off.” Over time I’ve learned to drastically scale my expectations back.

The truth is that launches are underwhelming for the majority of us. If the project doesn’t bomb altogether, it can take a long time to get traction. Hitting $10,000 MRR within 8 weeks is unrealistic for most of us.

I want to share how growing With Jack has looked for me. Starting off with no capital for marketing, a small audience and bootstrapping my way to 250 customers.

The Evolution Of With Jack's Customers

0-1 month

I recognised every name that signed up to With Jack when I first launched. These were friends and people from my immediate network who wanted to support my business. Thanks, fam!

1-6 months

At this stage I started seeing people I didn’t personally know, but there was one degree of separation. These were friends of friends who signed up from recommendations and referrals.

6-12 month

After 6-12 months I stopped recognising most of the individuals signing up to With Jack. They’re within the initial audience of web designers and developers I launched to, but I’m not familiar with them. This is exciting territory, but also scary!

12-18 months

Most recently I’ve seen a surge of quotes from people outside of the audience I’ve built With Jack for. These are occupations I’ve never advertised to or targeted, but are on the fringes of my target market.

18 months+

There’s now a trickle of quotes from occupations that have no connection to With Jack, like carers or plumbers. I turn these businesses away (politely, of course!).

Month One: Selling To Friends

Getting friends and family to be your first customers is a smart move with any product launch. It’s easy for a couple of reasons.

  1. You don’t have to convince them to trust you
  2. They’ll want to support your business

I’d spent a lot of time in the web industry before launching With Jack because of my interest in design and tech. I was attending conferences, speaking at meet-ups and was active on Twitter. Because of this I made friends in the industry.

I didn’t realise it at the time, but this would come in handy when launching With Jack a few years later. When I look through my first 30 customers, I count many of them as friends.

1-6 Months: Getting Friends To Recommend

Growing beyond friends was a fairly easy transition. All I had to do was convince my existing customers to recommend With Jack to their friends. This wasn’t difficult because, again, friends want to support your business. They should be happy to spread the word.

These days referrals account for most of my sign-ups. Existing customers refer us on Twitter or Facebook (if someone asks for a recommendation), or tell their friends about us.

I try encouraging referrals in two ways.

  1. Post-purchase I urge customers to tweet about being professionally insured via With Jack.
  2. Existing customers can intro a warm lead. If the lead buys insurance, they both get a reward.
Post-purchase I urge customers to tweet about being professionally insured via With Jack

We’ll have more scope to encourage referrals once we build the self-service quote system. They’ll be baked into the dashboard and customers will be able to track them.

Another method of encouraging referrals is the ‘Insured by’ badge. Customers (and friends!) like Naomi and Ryan are happy to plug With Jack on their site.

They get to show clients they’re equipped to get back to work quickly should something bad happen. And With Jack gets social proof and referrals. Win, win!

The Insured By badge

6-12 Months: Who Are These People?

At the 6-12 month mark I was starting to get customers who weren’t connected by one degree of separation. They’re still within the initial audience I built With Jack for, but they’re finding us through organic search and marketing channels like that.

Because of the channels they’re discovering With Jack through, they know little about the company itself. Their first interaction isn’t from seeing a tweet or blog post by me. In fact, many don’t know that With Jack is a one-woman, bootstrapped startup.

Ashley bootstrapping With Jack
This is me, Ashley. Bootstrapping With Jack as a solo founder. Hey!

This is exciting territory because it signifies growth, but it’s also scary.

It’s at this stage I started to feel With Jack was ‘growing up’. There’s less room for error. You have to work harder to convert leads and please customers who have no emotional connection to the business.

These customers are less engaged. They aren’t as likely to sign up to the newsletter, and aren’t as interested in following along the journey. Come renewal time, they’re likelier to shop around and be more willing to switch providers.

This is an interesting challenge and poses the question, “How can I turn these customers into fans?”.

12-18 Months: Potential New Markets

70% of With Jack’s customers are made up of the initial audience I launched to. The majority of my customers are designers and developers. The rest is typically made up of internet marketers, photographers and consultants.

At this stage I started getting quotes for industries I hadn’t advertised to. I hadn’t built landing pages to target them or wasn’t creating content to attract them.

It does feel like a natural progression, though, because they fall on the fringes of the audience I launched to. For example, it’s not difficult to see how a service built for web designers and internet marketers may attract copywriters.

Provided the role doesn’t stray too far from the audience I built With Jack for, they’ll be able to buy insurance without any hiccups.

If I see a lot of one sector consistently requesting quotes, that’s when I decide it’s time to build support for them into the quote system.

18 Months+: Turd Sandwich Making

Lately the phone has been ringing and quotes have been coming through from businesses I didn’t build With Jack for. This isn’t a bad thing, but more often than not I’ll send them elsewhere.

I’ve designed the customer journey for a specific group of people. I don’t want With Jack to be the insurance platform for everyone—I feel like that’s what most other insurers are trying to be. I want to build a remarkable product for a small group of people.

Being laser-focused on a specific audience means offering insurance that suits the work they do, instead of confusing them with products that aren’t relevant. The customer journey, the products we offer… it’s designed with my target audience in mind.

Maybe I could sign these businesses up as customers, but they’re not going to get the best experience because it wasn’t built for them.

P.S. A recent quote came in for ‘turd sandwich making’. An industry I don’t target, nor have I even heard of.

The Journey Looks Different For Everyone

Growth doesn’t look the same for everyone, but this is how the path to 250 customers has looked for me. There are hundreds of ways to grow your business. There’s no right or wrong way (unless you’re not providing a good service. That’s the wrong way).

But if all we hear are the stories about getting 300,000 users in 24 hours or earning 6 digits in 48 hours, many of us will feel disheartened and doubt ourselves. Maybe some will even give up.

I remember shipping a project 4 years ago on the same day a friend launched their company. I watched them share photos of celebration and champagne as I struggled to get a sale in my first 2 weeks. Nothing good came of comparing my launch to theirs.

AirBnB had a disastrous launch. They launched with only 6 listings and from those 6 listings just 2 became bookings. Can you imagine if they’d given up at that point?

Astronomical traction wasn’t a reality for me, but starting small and growing slowly has been. Sharing these stories is important so we can see how different the journey looks for everyone. The vast majority of us won’t experience the overnight success—and that’s OK!

Ashley Baxter's Picture

About Ashley Baxter

Ashley is building With Jack so you can be a confident freelancer. She likes video games, photography, and her dog, Indie. Based in Glasgow, Scotland.

Glasgow, Scotland iamashley.co.uk