My Journey To 250 Customers

My Journey To 250 Customers

This post is available in audio format.

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!

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The 'Why' Behind Building With Jack

The 'Why' Behind Building With Jack

This post is available in audio format.

Last week was challenging. Personally and professionally I felt worn down and tested. It was one of those moments where I question why I’m doing this. Those times don’t happen often, but when they strike they’re debilitating.

Breaking into the insurance industry is tough. Doing it as a self-funded, solo founder is crazy.

A few things aggravated me, but a big source of stress came from my delegated authority application. If approved it means selling policies from With Jack’s platform instead of manually processing quotes.

(Fun fact: I’ve manually processed £200,000 of quotes. This equates to 45 consecutive hours at a computer. One of those quotes was from on top of a volcano in Spain!)

I can’t emphasise this enough, but insurance is not start-up friendly. It’s heavily regulated, capital intensive, low margin and highly competitive. It’s times like this—with the red tape and paperwork—that test me.

I can admit my strengths and weaknesses. Filling out applications, writing business plans and financial projections is not my strength.

There were a lot of spinning plates last week and I don’t have a co-founder to split the workload with. It all got on top of me. This lead to me questioning why I didn’t choose an easier industry, or why I’m building a business altogether.

The Start-Up Rollercoaster

It doesn’t actually matter what industry you build a business in. There are always going to be moments of self-doubt and questioning your sanity. Irrespective of sector, building any kind of business is hard work.

This paragraph from the Baremetrics blog nails it.

"I always remember one of the first days we started working on our business full time in a coworking space in London and someone who had done it for a while came up to me and said “be prepared to find out what it’s like being bipolar” — it’s always stuck with me as a reminder that it always gets bad, but you’re on the journey because the highs make up for the lows"

Last week was one of the ‘lows’. I was juggling multiple balls at work, working to various deadlines and trying to complete my application. I’ve put a lot of pressure on myself regarding the latter. In my personal life, my flat had flooded and I was living in a building site. I felt a bit fed up.

Fortunately, I was reminded of why I’m doing this in the form of a post-it note I wrote in December 2013. This was when I first started thinking about what would become With Jack. It summarises my motivation for starting my own business in the insurance space.

My post-it note from December 2013
It needs to be human, it rewards loyal customers and the technology doesn't suck.

It addressed some of the problems I was noticing in insurance at the time. Such as:

  • 74% of insurance companies see technological innovation as a challenge, but few are developing their own offerings in-house or partnering up with start-ups.
  • 73% of consumers don’t trust their insurance provider.
  • 2 out of 3 customers are unhappy with their journey through buying insurance.

Basically, the technology sucked and insurers weren’t customer-focused.

Solutions Are Born From Frustrations

When I wrote this post-it note, I had been working in insurance for 8 years and was frustrated with the industry. I wanted change and started exploring how my own insurance business would look.

My insurance company would be human, I thought. Nobody needs another faceless corporation. Let’s drop the legal jargon that litters the buying experience. People should understand what they’re paying for. I’d build it with modern technology and good design instead of the legacy systems insurers are locked into. Loyal customers will be rewarded. We’re accustomed to rising premiums every year even when we haven’t claimed. Why do insurers punish us for being loyal customers? They do a great job of making us feel unappreciated.

During last week’s slog I returned to this post-it note. It was a reminder of my motivation for starting With Jack—the ‘why’ behind it—and served as a sanity check during a tough week.

I remember writing this. I was working from Toad’s Caravan and excited about beginning something new. That place of not knowing where the idea would take me, but being optimistic about the outcome and what lay ahead.

The reality of what lay ahead was a long and bumpy journey fraught with obstacles and rejection. If a crystall ball had shown what would stand between me and those objectives on the post-it note, I’d never have started.

Here are just a few of the obstacles I’ve faced on my start-up journey:

  1. Getting dropped by the insurer I was an affiliate for
  2. Spending 2 years trying to find an insurer to work with
  3. A lot of rejection, knock-backs and dead-end meetings
  4. Getting admitted to hospital with burnout
  5. Navigating an industry that isn’t start-up friendly without a conventional background in insurance, co-founder or funding

There are various stages of building a business. I’m sure they look different for everyone, but for me they look like this:

  • “This is a great idea. I am so going to do this” (initial excitement. This was when I wrote the post-it note)
  • “Huh. This is kind of hard. I’m not so sure about this” (trying to find an insurer to work with)
  • “This totally sucks. I suck. What was I thinking!” (various moments—most recently last week!)

When I wrote this post-it note, I had no idea it’d take another 2.5 years to launch With Jack. Beyond launch, it’d be another 1.5 years (and counting) of manually processing quotes. That’s a lot of opportunity to get distracted, want to start over or give up entirely.

As founders, we all experience moments that test our commitment. I think it’s important to talk about them because most people only highlight the wins. As much as I enjoy celebrating my wins, I’ll admit I’m not “crushing it” 24/7.

There are some moments it all feels impossible. With those periods it’s easy to forget the ‘why’ behind what you’re building and consider abandoning ship.

Pre and post-launch there will be those moments. Prepare to have times you’ll feel lost, distracted and burnt out. I was there last week. I’ll be there again in the future.

To get through it, it helps to know your ‘why’. This keeps you focused when sign-ups aren’t growing quickly, or when a competitor is shipping more features, or when you have to write another business plan because the last 2 were rejected, or when churn is higher than normal.

You get the gist.

The Reasons I Started My Business

I’m 1.5 years into building With Jack. Does my original mission still drive me and get me out of bed in the morning?

Yes, it does. Although it’s still a work in progress (but that’s part of the fun and frustration).

It Needs To Be Human

This is one thing With Jack does well. My customers even say so.

What does With Jack do well?
What does With Jack do well?

With Jack achieves this through a combination of its conversational interface, and genuinely caring that customers have a good experience.

I’ll refrain from cookie-cutter customer service terminology (“We apologise for any inconvenience”) and try to be real. It’s obvious when a customer service rep is reading from a script. There’s nothing human about that.

With the customer journey, we strive to keep it personable and engaging. When I deal with customers, I try to be anything but a corporate insurer. My target audience appreciate this.

This is a crucial part of With Jack’s DNA. It’s still just as important to me 1.5 years into building my business.

It Rewards Loyal Customers

As a consumer, I regularly see my premium skyrocket only to be offered a better deal when I threaten to leave. A lot of big companies treat existing customers unfairly. Bells and whistles are reserved for attracting new customers.

I tackle this by allocating more resources to pleasing existing customers instead of chasing new ones.

As a bootstrapped start-up it’s going to cost more to acquire new customers than retain existing ones. It’s more effective to treat my existing customers well and let them market With Jack for me. It’s not rocket science.

Rewarding loyal customers isn’t just about not nonsensically raising premiums. I’ll share their achievements on Twitter, show gratitude for their support and take an interest in their work. This is another important part of With Jack’s DNA.

The Technology Doesn't Suck

Technology in the insurance industry has changed a lot since 2013. There was no ‘insurtech’ scene (gosh, I despise that term).

Now the entire industry is focused on technology. When I built my first quote system it was fully responsive—an approach that hadn’t yet been adopted by the industry. Now there are a lot of interesting ‘insurtech’ start-ups, and With Jack is lagging behind on the tech front.

That won’t always be the case. Part of last week’s stress stemmed from submitting my delegated authority application, which will open doors to improving the technology. It means building a self-service platform and gives us more scope for creativity.

From the three objectives on the post-it note, this is the one I’ve made the least progress with. That surprises and disappoints me.

Chasing The Dream 4 Years On…

Building a business is hard work and emotionally draining. Remembering my ‘why’ has helped keep me focused during those low moments.

As my stressful week has come to a close, I feel better having revisited the reasons I started With Jack. I remember why I’m doing this. I acknowledge there will be other tough periods and every founder has these moments. I prepare for another week of putting one foot in front of the other, even if it doesn’t always feel like I’m moving forward.

My goal is to build a customer-focused insurance business with design and technology at its core. Achieving this means helping more freelancers protect their business and livelihood. That’s something that drives me forward and gets me out of bed, however challenging things seem.

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Start Talking About Your Idea

Start Talking About Your Idea

I’ve built (and shipped!) various projects over the years. These have ranged from online courses to SaaS apps and podcasts. Some of these projects have failed. Others did OK. And With Jack—the business I’m building now—made money before it even launched.

The failed projects taught me a lot. Each mistake I made culminated in a successful launch for the project that’s mattered most—With Jack. (Well, successful by my standards given I had no money for marketing.)

But let’s not get into With Jack just yet. First I want to explore why it’s important to talk about your ideas before you write a line of code.

The Project Where I Kept My Cards Close To My Chest

One of the first projects I wanted to monetise was Lodger, a SaaS app for landlords. It was a simple tool for landlords to manage tenants and payments. Lodger is one of my many ideas that flopped.

Reasons Lodger Failed

It’s easy to see why Lodger failed. There’s nothing I did right at any step in this project.

  • I targeted an audience I had no interest in
  • I didn’t do customer development or research what features users would want
  • I spent 9 months building a fully functioning SaaS app I hadn’t validated
  • I had no existing audience to market to

I built something I thought landlords would value, instead of researching what they actually need.

Not having an audience to market to was also an issue, but that’s secondary to not recruiting feedback prior to and during the development stage. After all, it doesn’t matter how big your audience is—if what you’re building only solves an imaginary problem, nobody’s going to give you money for it.

Since then I’ve taken online courses, listened to podcasts and read blog posts on the subject of product creation. They’ve all taught me the same thing. To have any chance at building a successful business, you must uncover a pain or desire a group of people have and work with them to develop a solution to it.

That’s the opposite of what I did with Lodger. I had an idea, locked myself away in my office and built it.

This wasn’t a quick mistake I got out of the way after a few evenings and weekends spent coding. This was the project that taught me how to code, so it wasn’t built overnight. 9 months of learning Ruby and a lot of hours on Stack Overflow. Women grow human beings in that time!

With Lodger being my first app I wanted it to be perfect. As I was progressing with learning Ruby, I’d go back and refactor my early code. A completely pointless act given I had 0 users. Hey, at least I felt like I was being productive.

Not only did I invest a lot of time building it, I wanted it to look slicker than the competition. This was going to be the edge against my competitors (or so I thought), many of which were desktop apps with clip-art inspired icons. So, I hired a designer and Lodger looked great.


I received compliments like this:

And this:

On the surface these compliments felt like validation and made me feel good, but there was a big problem. These words weren’t coming from the people who would pay for the app. There were no glowing testimonials from landlords who’d finally found the solution to their burning problem, because Lodger wasn’t solving a burning problem.

Speaking to my target market and validating there was a need for Lodger—instead of diving into Sublime Text and Photoshop—would have saved me 9 months of work. (Another lesson I’d learn is that landlords don’t care if software looks nice or has squeaky clean code.)

What design can’t do is solve a fundamental problem in your business model — Reid Hoffman

Where I failed was by not talking to landlords and uncovering a pressing pain they all had. I didn’t design a solution they’d pay for. I just built something I thought they would like, which is stupid because I’m not a landlord.

This all sounds obvious, but I’m not alone in doing this. A lot of people take this approach when building stuff.

“I have an idea. It’s going to be brilliant and will make money. Instead of validating there’s any need for it, I’ll dive into my code editor and start building it.” Does this thought process sound familiar?

In a monetory sense Lodger was a failure. My SaaS app generated £0 in revenue and I’d spent thousands of pounds in design fees. The only purpose it served was a lesson in how not to build a business (and also how to code).

Learning From Past Mistakes

Now onto the story of With Jack…

This looks very different to my experience building Lodger. I intentionally did things differently.

With Jack is the first project I’ve made money from prior to launching. It’s the first project I’ve embraced imperfections with and built in a public way, with the input of my customers. Maybe that’s why it made money prior to launch.

I started small. I tested the water by signing up as an affiliate for an insurance broker. Whilst I couldn’t build my own tech and customer journey, it meant I could launch something quickly and gauge interest. That interest was 55 sign-ups, £14,000 Gross Premium Written and positive feedback towards the brand.

That was my first step in validating With Jack.

The next step was to get authorised and partner with an insurer so I could build my own tech (insurance is a regulated industry). Whilst going through that process, I put up a landing page with a few paragraphs about my vision for With Jack. I followed this with a call to action to be notified of launch.

120+ people signed up. It was a small list, but they were engaged. I shared what I was building with this list, sourced feedback from them and invited them to beta test. Several of these beta testers became my first customers.

This process of sourcing feedback before writing code is still at the core of With Jack, 1.5 years later.

Unlike the SaaS app, With Jack is growing every month. It’s consistently made money from day one. Out of all of the ideas I’ve executed on, this is the one that functions like a business.

Don't Make The Same Mistake I Did

Maybe I’ve skirted around why I’m writing about this, but I wanted to open by sharing my different experiences of building Lodger and With Jack.

The point of this post is to prevent people from making the same mistake I did. Coming up with an idea, convinced it’ll work without validating it, then spending months building out a complete vision.

More often than not, the idea doesn’t take off. It’s a lot of work and disappointment that could have been avoided had there been some initial validation.

I’ve seen a lot of people skip idea validation. Recent experiences of seeing this happen have been the catalyst for this blog post.

Last month I gave my talk—Idea to Execution and Beyond—at Frontend NE in Newcastle. Afterwards somebody approached me with a question. Our conversation went like this:

Guy: “How much would insurance for my startup cost?”

Me: “It depends. What does your startup do?”

Guy: “I can’t tell you. We haven’t launched yet and we don’t want anybody stealing our idea”.

I had just given a talk about the importance of idea validation. He said he’d enjoyed most of my talk, but disagreed with that part. That’s OK, I don’t expect everyone to agree with me. Yet I couldn’t help but feel he’s shooting himself in the foot before he’s even started. And I told him that.

“How do you know this idea is worth your time and money if you aren’t speaking to people and validating it?”

“How do you know you’re building something people want if you aren’t talking to potential customers?”

Those were a couple of the questions I asked him. I wish somebody had asked me this when I was building Lodger. I wouldn’t have had an answer, which would hopefully have served as a wake-up call.

Not long after my conversation at Frontend NE, I watched a friend of mine start a business. She’s following my doomed footsteps with Lodger. She’s avoided doing any customer development and is building her app in secrecy, but she has printed business cards and t-shirts with her business logo on them.

I love how excited she is about this, but it’s quite simple—before you invest resources into building something you must validate there’s a need for it. Otherwise you’ll potentially waste time and money only to realise that nobody wants it.

I’ve been there. I’ve done that. It sucks.

Why It's Important To Talk About Your Ideas

Despite idea validation being an important step of building something, a lot of us skip it. Here’s why you shouldn’t:

  • It helps you avoid spending time and money building pixel perfect products. You don’t want to wait until launch to discover nobody wants what you’ve built (I should know. I did this)
  • Whether it’s from pre-orders or beta testers, you can generate revenue earlier. If people aren’t prepared to give you money then you’ll know the idea doesn’t have legs and you should pivot
  • You’ll build a product people want, instead of building what you think people want
  • Our ideas usually aren’t as good as we think they are. It’s better to get real feedback from people who aren’t emotionally invested in it

Building stuff is hard. Be it a side project or business, burying your head in code and emerging months down the line with a finished product is taking an expensive stab in the dark. You’re making the process harder for yourself.

The top reason that startups fail is that there’s no market need. I’m guessing a lot of those failures—Lodger included—could have been dodged if we talked about our ideas earlier. The odds of success could have been improved if we were speaking with potential customers, validating there’s a market need and generating revenue.

Okay, I’ve oversimplified the reason startups fail. But talking to people about what you’re building is a great place to start!

Why Don't People Talk About Their Ideas?

I’m sure everyone has different reasons for not sharing their ideas. The guy that spoke to me at Frontend NE was worried people would steal his. My friend with her new business is excited to get stuck in.

When it came to building Lodger, I had three reasons for diving into the build instead of talking about it.

  1. I was convinced my idea was good
  2. I was embarrassed by the thought of sharing a product that was less than perfect
  3. I didn’t have any connections in the buy-to-let scene. Rounding up a herd of landlords for customer development seemed intimidating

I’m a big fan of Reid Hoffman’s podcast, Masters of Scale. One of the recent episodes saw Reid Hoffman interview Payal Kadakia about her startup, Classtivity. Classtivity didn’t have a successful launch and would later pivot to ClassPass.

I’ll paste part of the transcript below, but you should really download and listen to all of the episodes.

Hoffman: Frequent listeners of this show may recall my theory that you never want to release a fully realized vision in the software world — because it’s most likely flawed. In fact, if you’re not embarrassed by your first release, you’ve released it too late. Many successful entrepreneurs have discovered this counterintuitive theory the hard way. They perfect their product, as Payal did, and then on launch day, well…I’ll let her tell the rest.

Kadakia: And so, June of 2012, we launched Classtivity, finally open to the public. We had thousands of classes listed, a beautiful design. And I would say we did about ten reservations a month. It was terrible.

I can relate to Kadakia with my SaaS experience. We both focused on honing a beautiful design. We both launched with a feature-rich product. We both failed.

Later in the podcast, Kadakia talks about the pivot to ClassPass.

Kadakia: We were sitting behind the screen here, right? For a year-and-a-half, we were building API integrations. We were building scrapers to get the schedule data. We weren’t talking to our partners or our customers. And that was also something that we started doing.

Hoffman: Payal started interviewing fitness studio owners. She asked one after the next, how do you get people to sign up for a class? And immediately she spotted a pattern of responses.

Classtivity pivoted to ClassPass when they finally got away from their screens and started speaking to customers. ClassPass was last valued at $400 million.

But what if somebody steals your idea? This is the fear the guy I spoke to at Frontend NE has.

Don’t let fear of idea theft stop you from speaking to potential customers. My logic is that people can steal your idea post-launch. You may as well start talking about it now. You’ll get a head start, build a product people actually want and start to acquire customers.

In Closing

I did a lot of things right when building With Jack. It wasn’t the perfect formula, but it was better than my attempt at building Lodger.

I started small. I made a bit of money by testing the water as an affiliate. I spoke to my target audience. I built an email list and involved them in the build process. I launched with manual processes. The business has been growing every month, unlike Lodger that was dead in the water.

All idea validation should involve speaking to potential customers, but here are some other avenues to test if your idea has legs.

Publish a blog post

A great example of validating an idea with a blog post is Ghost, the blogging platform. John wrote about his concept for Ghost in 2012. It generated enough of a response to justify exploring a prototype.

Monitor interest with a tweet

Today I saw my friend, Ben, publish a Twitter poll. He was using the answers to “validate a tiny idea for a tiny app”.

Design a landing page

Landing pages are typically what spring to mind when talking about idea validation. I used this method to build a small email list and get beta testers, several of whom became my first customers.

Build a micro version of your idea

Pieter wrote about surpassing $50K a month in revenue, but Nomad list originally began as a spreadsheet. It was a tiny version of what’s become the biggest crowdsourced database of cities in the world.

Please don’t waste resources building something before validating it. I don’t care how good you think your idea is or how afraid you are that someone will steal it. You need to confirm it’s something people want. How you validate it is up to you. Don’t wait until your product is perfect. Involve your audience as early as possible. Never assume you have a million-pound idea.

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Improving With Jack's Sign-Up Rate By 14%

Improving With Jack's Sign-Up Rate By 14%

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I first mentioned With Jack’s conversion rate when writing about my goals for 2017. As of December 2016, 26% of people who got a quote with Jack became customers.

Over the past 12 months we’ve been tweaking key parts of the customer journey. The conversion rate is now at 40%—a 14% improvement from 2016.

Scrappy Beginnings

It’s everyone’s goal to launch with a polished, feature-rich product. I did the opposite. I talk about this in my last post, Minimum Viable Process.

A lot of tasks at With Jack are manually processed by me (generating quotes and binding policies). This is something I thought would be a hindrance, but has stood me in good stead with talking to customers and building a better experience. Every day I’m getting some form of customer feedback—good or bad.

I speak about launching with one polished feature in my talk, Idea to Execution and Beyond. For Jack that was the conversational interface. This was where I channeled my money and attention. There were other important parts of the customer journey that I launched without.

For example, With Jack launched without a risk questions form. I was sending people to Typeform to answer them.

Aside: The risk questions cause the biggest friction in With Jack’s customer journey. It’s a necessary part of buying insurance to see if your business is insurable or a liability. That you implement good practices like obtaining licenses for images you use, haven’t had any claims etc. That kind of thing.

Bootstrapping means moving slowly. This can be frustrating when it feels like everyone around me is raising investment and moving quicker. But I’ve really started to see bootstrapping as a blessing.

It means not building features for the sake of it because I don’t have the money to do so. It means taking one step at a time and using feedback to ensure what we’re building or the changes we make serve a purpose.

After launching with one, polished feature (the conversational interface), we turned our attention to the risk questions. It was a quick win. We stepped away from Typeform and built a self-hosted form. Nothing fancy. It looked like this:

The original risk questions form

The risk questions suck, but not answering them invalidates your policy. They’re the worst part of the process and embody everything I hate about insurance.

Legal jargon that nobody understands. Text that doesn’t read in plain English. Questions that aren’t tailored to your chosen industry. I can’t imagine any scenario where a web designer’s work could result in loss of life, yet that’s one of the questions.

Frustratingly, I’m not allowed to change the risk questions (at least not now. In the future I may have enough clout to work with an insurer to write them). This part of the process is where users drop off.

The customer journey starts on a friendly tone (the conversational interface), but ends on something different (the risk questions). Transitioning from a chatty tone to stuffy and corporate is never going to be smooth.

That wasn’t the only problem. Some of the users who did hunker down and answer the risk questions found the process confusing.

“Is it the final step?”

“How do I pay?”

The Three Key Problems And How We Addressed Them

  1. People felt thrown by the change of tone and copy.
  2. There was nothing to indicate this was the final stage of getting insured.
  3. Payments weren’t clearly explained. Customers would receive an invoice after they submitted their risk questions. This wasn’t obvious.

Somebody once bought insurance ‘accidentally’. When I sent them their policy and invoice, they said “I didn’t mean to buy insurance. I thought this was just another step in getting my quote”. Clearly there was a problem.

I was enjoying a weekend away with Naomi Atkinson when talking about this. (Yes, I have bad chat. This is why my friends don’t want to hang out with me.) Naomi is a designer, so she suggested redesigning the risk questions to address these common confusions.

People felt thrown by the change of tone and copy

As I mentioned, there isn’t much we can do about this at the moment. We did make one tiny change that helped. We switched the ‘yes’ or ‘no’ answers to ‘true’ or ‘false’. This framed the questions in a way that read slightly better.

This has worked well. We no longer have people misunderstanding the questions and selecting the wrong answer. Emails from users asking for clarification about the questions have reduced.

There was nothing to indicate this was the final stage of getting insured

Naomi pre-faced the form by outlining the steps.

  1. Confirm your details.
  2. Answer the risk questions.
  3. Choose how you’d like to pay.

We also changed the call-to-action from ‘Submit risk questions’ to ‘Get insured’.

Changing the call-to-action is the simplest fix, yet gives the form focus. Asking people to submit their risk questions poses more questions (“Why? What happens next? What am I committing to right now?”), but providing a button to get insured gives clear direction.

Payment options weren't clearly explained

We changed how payments are handled. Gone is the option to pay by bank transfer and we’ve limited it to Direct Debit. Users can now choose monthly or annual payments (I’d estimate 95% of customers choose to pay monthly).

Taking Direct Debit details makes it feel more like a check-out process. It’s eliminated any confusion around payment.

This is what it looks like now:

The redesigned risk questions form that improved sign-ups by 14%

These tweaks significantly reduced the drop-off rate.

  • Changing the call-to-action
  • Setting expectations by outlining the steps
  • Offering better payment options

It all helped increase the conversion of quote to purchase by 14%. Oh, and since implementing these changes nobody has ‘accidentally’ bought insurance.

There's Always Work To Be Done

The sticking point is still the copy. The nature of the questions and the legal wording means some people abandon the process without getting insured. This pains me because the benefits of being insured outweigh the temporary inconvenience when buying it.

It’s a case of getting a cup of coffee, putting on your headphones and spending a few minutes pushing through the pain. A small trade-off for the sake of protecting your business from shit like this and this.

With that said, Scott (the designer I’m working with) and I brainstormed how we’re going to address this with the next version. We think we’ve come up with a solution.

Another issue we’re tackling with the redesign is the feeling of abandonment once you buy your insurance. At the moment, the customer journey is optimised around quoting and buying. Once you become a customer it can feel like you’re being deserted. That is until things get hairy or your annual renewal is due. We’re tackling this next. More on that soon…

This is what I love best about building With Jack. Listening to feedback and implementing it, then watching the effect it has. Finding problems or inefficiencies and trying to solve them. Getting more freelancers insured.

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Minimum Viable Process

Minimum Viable Process

This post is available in audio format.

I’m probably the only person to launch an insurance company in 2016 without automated quotes. How very internet of 1996. This was because I had:

  • no existing book of customers
  • no indication I could build a succesfull company
  • no funding

It’s easy to see why insurers weren’t beating down my door, wanting to work with me. I’d have to start at the bottom and prove I could convert leads.

It had taken 2 years to get an insurer onboard. When the opportunity came to work with an insurer but manually process quotes, I took it.

It wasn’t perfect, but I was eager to launch. This was the quickest way to get With Jack in front of real users! Plus, I figured it’d only be a few months before I’d have an automated system. In the meantime I was happy to handle everything manually.

This meant checking for quotes in a CRM tool, logging into my broker panel, processing the customer’s quote and sending it to them. A minimum viable process.

The manual process of customer quotes

It did seem unthinkable that this would be the long-term solution. My goal was to build an insurance company with design and technology at its core. A manual process contradicted that and assumed the role of a traditional broker—not a technology start-up.

I had other concerns about not having an automated quote system:

  1. It was 2016. People could buy their insurance with the click of a button elsewhere. How was I making insurance accessible if it wasn’t instant? I was worried people would be put off by Jack’s “sit back and have a doughnut while we process your details” approach.
  2. I’d lose sales. Simple. Without an automated process that flowed cohesively, users would drop off.

Expectations wouldn’t be met and the conversion rate would suffer.

16 months and 190 customers later, there’s still no automated quote system. I didn’t expect to be manually processing quotes for this long, but it turns out it’s been a blessing.

The Beauty Of The Manual Process

High Conversion Rate

40% of the people who get a quote with Jack become customers! Conversions have improved over time, starting at 26% when I launched (I’ll share the tweaks that have contributed to the change another time). My concern about users dropping off was unfounded.

Understanding Customers

I’ve spent the past 16 months having customer conversations. Most insurers have few touch points with customers and it’s usually in negative situations. Such as when a payment has failed or a customer makes a claim. Because they’re mostly dealing with customers in sensitive situations, this contributes to the negative connotations people have about insurance.

Let’s talk about customer conversations.

I’ve manually processed each of the 190 sales. This means I’ve conversed with 190 of the very people I’m building With Jack for. That’s invaluable! I’ve learned:

  • Where customers come from
  • Who referred them
  • Why they signed up
  • What they thought of the experience—good and bad
  • Their motivations for getting insured

Forming an understanding of this helps me improve the service and understand how and where to market it. This has been crucial in informing my decisions. It’s also influenced the copy and design changes we’re making.

Lastly, it’s enabled me to connect and build deeper relationships with customers.

Don’t get me wrong, not everybody wants to engage. Some people prefer to sign up with as little interaction as possible. They want to check a box, be on their way and don’t care who is powering the experience for them.

(Despite having to manually process everything, it’s possible to buy a policy via Jack without interacting with me personally.)

But for many—and the type of customer I’m hoping to attract—they want more from their insurance. They’re happy to engage and shape With Jack.

After the fear of launching without instant quotes, it turns out people are OK with the human element. The proof? 40% of people who get a quote convert to customers and 87% choose to stay come renewal time. (The 13% churn is attributed to freelancers taking up full-time employment, winding down their business or relocating abroad.)

Customer development has been the most valuable thing we’ve done when it comes to moving our product and company forward, and I wish we would’ve done more of it in our early days. — What To Do If You Didn't Get Into Y Combinator

When I launched in 2016 I wasn’t thinking along the lines of customer development. I didn’t even know what that was. The manual process was simply the quickest way to ship.

16 months later and I echo Alex’s comment above—customer development has been the most valuable thing to inch With Jack forward. Speaking to customers has been as a direct result of having to manually process quotes.

The Downside Of The Manual Process

I can never be too far from a computer.

This month I enjoyed my first holiday since launching With Jack. A Canary island off the coast of West Africa, 24 degrees celsius in January. The catch? I had to carry my laptop everywhere.

I onboarded a customer on the airport bus. I sent quotes by the poolside. I answered emails over dinner. Most impressively, I emailed somebody their quote from on top of a volcano! Amen for tethering.

The view from the volcano

Fun fact: Volcano quote converted and was the biggest sale I’ve had this year. It was definitely worth it.

I did get stick for being on my laptop. A lot of the people I was holidaying with work 9-5 and have the luxury of switching off. Being my own boss meant I couldn’t disconnect completely. If quotes came in, they had to be dealt with.

This is the downside of manually processing quotes, but it’s a small price to pay and is temporary. I’m at a stage where every sale is crucial.

Automation Is Coming

Instant quotes. They’re coming. Scott’s in the process of designing the customer journey and the insurance paperwork is being completed.

I’m aiming to keep an element of human throughout. It will be a balancing act and I won’t get it right from day one, but I’ll iterate on it.

With a customer journey that’s scoring a 40% conversion rate, I am afraid the automation will negatively affect that. However, from the customer conversations I’ve had I know that I’ve lost sales due to not having instant quotes. Existing customers have also expressed their preference for automated quotes when shopping for insurance. It will also allow us to experiment more with the customer journey.

What's The Point In All Of This?

I have two takeaways.

  1. Launch with the simplest version of your product or service (a small experiment).

    At one point I’d have considered delaying the launch of With Jack until the system was automated. Not because I was deterred by the work involved in manually processing everything, but because I believed customers would be discouraged by it.

    I was wrong. The idea should always be to launch with the simplest approach, speak to customers and learn. Sometimes that means manual processes!

    An MVP is a process that you repeat over and over again: Identify your riskiest assumption, find the smallest possible experiment to test that assumption, and use the results of the experiment to course correct. — Minimum Viable Product Process
  2. Build customer development into your business from day one.

I can’t stress this enough. With Jack’s growth has been slow and steady—this is the nature of bootstrapping. But long-term I’ll have a competitive advantage because of these conversations.

Speak To Everybody—Customers, Potential Customers and Lost Customers

40% of people who get a quote convert to customers, but that leaves 60% who don’t. I don’t ignore them, even if it does mean having uncomfortable conversations about why they didn’t sign up.

It’s trickier getting a follow-up from lost sales. They’re not invested in the service, so likely won’t take the time to provide constructive feedback.

The direct approach has had little success for me. A final email to ask why they didn’t sign up mostly goes ignored. I’ve had more success using a survey tool (I use Iterate). I still won’t get a high response rate, but it’s worked better than email. I create a short survey with 3 questions and stress it’s anonymous.

When I send a link to the survey, I try appealing for feedback on a personal level (“As a one-woman startup, this feedback really helps and goes into shaping With Jack”).

Here’s some of the feedback I’ve been getting:

Using Iterate to collect lapsed user feedback

Decided not to take out insurance policy

That in itself isn’t helpful, but they elaborated on the question that follows it (What can we do to make With Jack better for you?). From their response I can gather they were happy with the customer journey, but were shopping around and choosing a provider based on price.

My client insisted on a ridiculous level of cover

I see this a lot. Their client gave them a boilerplate contract they also use for big companies. It demanded £10,000,000 of professional indemnity, public liability and employers’ liability! This isn’t an uncommon scenario and freelancers should push back on those terms. From this feedback, I could write a blog post about what to do when your client requests a high level of cover.

I needed worldwide cover

This is interesting. With Jack can arrange worldwide cover, but this indicates I haven’t done a good job of being clear about that. Now I have something actionable to implement; do a better job of highlighting this feature.

Manual Processes FTW

Waiting until With Jack was automated would have delayed my launch and cost significantly more to build. Instead I was able to ship quickly, start earning money and learn from customers immediately. With the automated system, I would have missed out on a lot of insights.

Switching to instant quotes means missing out on conversations at this point in the customer journey. That’s something I’ll miss. I believe this is what’s helped me bootstrap With Jack from the first 20 users to (almost) 200.

I hope automated quotes will take me from 200 to 2000.

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