What I Learned About Product, Growth And Strategy At Turing Fest

What I Learned About Product, Growth And Strategy At Turing Fest

Turing Fest returned to Edinburgh for another year. It’s a multi-track, two-day conference for the tech industry spanning 6 topics—product, engineering, strategy, growth, marketing and culture.

I could only attend the first day as I was in Newcastle for a friend’s wedding on day two. This meant I could choose any of the talks from day one’s three tracks—product, growth and strategy.

When I attend conferences, I want to come away with ideas, inspiration or knowledge I can apply to With Jack. Here’s what I learned.

Roan Lavery | Product | Driving Growth vs. Building Core Value

Roan Lavery

Roan spoke about FreeAgent’s three-step approach to perfect product harmony. This was my favourite talk of the day. It felt the most relevant to what I’m doing at With Jack and was also the most practical talk I attended.

Step One: Articulate Core Value

Roan shared the core value map that’s helped articulate FreeAgent’s vision (making businesses happier by putting them in control of their finances).

I’ve been learning about JTBD recently and exploring what that means for With Jack, so this was timely content. I’ve been shifting my mindset from “we’re an insurance business” to “what are our customers hiring us to do and how do we help them succeed?”.

The core value map helps you make sense of user needs, jobs to be done and features, which is all tied together by vision.

Step Two: Map User Journeys

The idea here is to engage users with your core value early and often. There are various stages to do this—initial onboarding, early usage, established use and even when customers churn.

Roan walked us through FreeAgent’s user journey and the decisions they made to drive growth by engaging users with their core value. Remember, FreeAgent’s core value is to make businesses happier and more successful by putting them in control of their finances.

There were a few points in FreeAgent’s onboarding that frustrated users. By combining or removing steps they were able to improve the customer journey and user happiness. This puts the user closer to being in control of their finances quicker.

Step Three: Create A Balanced Scorecard

Roan introduced us to Google’s HEART framework.


I had never heard of this framework before, but it’s used to measure the quality of user experience. From there you can identify which areas need improved, helping you decide what to prioritise.

I recommend checking out Roan’s slides from his talk Driving Growth vs. Building Core Value.

Gabrielle Bufrem | Product | Bootstrapping User Research: No Budget, No Team, No Buy-in, No Problem

The reason I chose Gabrielle’s talk was because I’m bootstrapping With Jack and user research is a huge part of what I do. I think I’ve got a good handle on conducting user research without a budget, but thought I might pick up a tip or two from Gabrielle.

At the moment I schedule calls with customers and use Iterate to capture feedback from sign-ups and lapsed users. I’ll also meet them in person, if possible.

Some of the talk wasn’t relevant to me, such as how to get your team to buy into user research, because I work alone.

This talk was a welcome reminder to get out from behind your computer screen and speak to real people. That you should be recruiting your customers to be your user research.

With Jack has an engaged customer-base and they’re willing to share feedback, but Gabrielle provided some ideas for getting people to do your user research without a budget. She suggests giving away swag or early access to a beta.

See Gabrielle’s slides from her talk Bootstrapping User Research.

Steli Efti | Growth | The 7 Deadly Startup Sales Sins

Steli Efti

I’m familiar with Steli because of his podcast with Hiten Shah (I was surprised so few people had heard of him). This talk had a lot of swearing. Whilst I’m not offended by swearing, I felt the content of the talk was lost amongst that.

A few of my favourite sales takeaways:

  • Simply ask, “What will it take to make you a customer?”. This is very simple advice yet something I’ve never done! I dance around sales and feel uncomfortable being so direct. I’m going to try this next time someone’s on the fence or weighing us up against a competitor
  • Be confident in your product and don’t offer discounts. Discounting is a race to the bottom. Nobody expects to use their insurance, so it’s no surprise many don’t see the value in it and haggle on price. I rarely give discounts (my profit margin is small enough and I actually want to be in business for many years) and prefer to sell With Jack on having a great product and customer experience. This is something I feel strongly about. I don’t want to be known as the cheapest, I want to be known as the best
  • Follow up more often. Do it until you get a yes or a no. My current approach to following up is lax. I only follow-up twice because I hate the harassing sales culture of insurance. However, a large portion of my sales come from follow-ups so I know it’s effective. It’s difficult balancing respecting people’s time with driving growth

See Steli’s slides from his talk The 7 Deadly Startup Sales Sins.

Des Traynor | What We’ve Learned From Scaling to 0-25k+ Paying Customers

Des Traynor

Des was the keynote speaker and the talk I was anticipating the most. I’ve followed Des on Twitter for several months and enjoy his writing.

This talk didn’t disappoint, but it was typical I had a flurry of sales come through just before it started. This meant I missed the first 5 minutes, then spent much of the rest of Des’ talk processing and sending quotes.

I’m used to this. I’m not complaining. With Jack is growing—what more can I want? But I would love another chance to hear Des speaking and give it 100% of my attention.

The parts of the talk I did catch:

  • Questions to ask yourself before starting a business. Will this problem exist in 10 years? How do people currently solve it?
  • Knowing your competitors. There are direct competitors doing the same job as you in the same way. Secondary competitors doing the same job in a different way and indirect competitors doing a different job with a conflicting outcome (think Weight Watchers and McDonalds). Know your competitors and understand why people should switch to you
  • Understanding how people buy your product. Is it problem based where they’ll search for a description of their problem? (“My client is threatening legal action against me.”) Category based where they’ll search for a solution? (“I need insurance that protects my business”) Competitor based where they’ll search for a better version of what they have? Or brand based where they’re looking for you?

What I Liked And Didn't Like About Turing Fest

Mark Logan

I’ve fallen away from the conference circuit in recent years. It’s because of exactly what happened during Des’ talk—I was preoccupied with running my business. However, it’s not often something like Turing Fest happens on my doorstep.

One thing I felt let down by was that many of the talks weren’t as advertised. The content of them didn’t match my expectations from the titles. I attended many talks only to find the content was different to what I was anticipating. After speaking to others about this I know I wasn’t the only person who felt this way.

What I did like about Turing Fest is the variety of talks. Having 3 to choose from ensures you’re picking what’s most relevant to you at that stage in your business. I also like the shorter format of talks. They’re about half an hour long, which I think is the perfect length for a full-day conference.

I definitely picked up a few tips and ideas for With Jack. Now to get to work implementing them!

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Positioning Your Product To A Tiny Audience

Positioning Your Product To A Tiny Audience

There is no silver bullet in building a remarkable product and it might take you months or even years to find the right recipe, but if you start with a small audience and gather feedback on the way, your chance of coming up with a remarkable product or service will get much, much higher. — How Seth Godin Would Launch a New Business

My business, With Jack, isn’t reinventing the wheel. It’s all manual processes and I’m not doing anything innovative.

If you were to ask what makes With Jack different, currently I’d say not much. Sure, people enjoy the conversational interface instead of a generic form. And yes, customers are delighted when I respond to enquiries at lightning speed. But I’m not disrupting an industry.

What I am doing is building my book of customers. I’m talking to people and making discoveries that will in time lead to creating a remarkable product, all whilst growing monthly revenue.

This approach has enabled me to get to market quickly, at a low cost and start collecting insights.

Build a remarkable product for a tiny audience

I’ve created With Jack for a small audience. 70% of my customers are freelance web designers and developers. The rest is comprised of internet marketers, photographers and businesses that fall on the fringes of digital and creative.

If you’re a plumber or estate agent, I’ll recommend you go elsewhere.

Getting a quote with Jack means not being shown 200+ occupations that aren’t relevant to you. You won’t have to scroll forever to find a category you think you fit into.

We know who we’re building With Jack for, so every design, copy and product decision is influenced by that.

Positioning With Jack for freelancers means only showing the type of insurance that’s relevant to them. A lot of sole traders approach me with insurance packages they’ve purchased elsewhere that have uneccesary cover added.

It’s not that the insurer intentionally tried extracting more money from the sale. It’s that they’re targeting so many types of businesses, their customer journey, packages and products aren’t right for everyone. This means some businesses end up paying for cover they don’t need.

On With Jack’s blog, you’ll find stories that resonate with freelancers. You won’t read about the importance of public liability because of the risks working on a construction site presents.

Instead you’ll hear stories about insurance helping with scope creep, missing project deadlines and client relationships breaking down. You know, the kind of stuff that’s relevant to our target audience.

Lastly, once you’ve bought your policy you’ll receive a host of benefits that are relevant to the work you do. This includes discounts for software, eBooks or learning material for freelancers.

Perhaps I’ve overused the term ‘relevant’, but that’s the key word here. Applicable. Apt. Fitting. Because we’re not trying to target every type of business in all industries, we can perfect each area of With Jack for our tiny audience. That’s the power of positioning.

Why freelancers?

There were a few reasons I positioned With Jack for freelancers.

I had experience in their world

I was a freelance wedding photographer for 6 years. I know some of the fears I faced when freelancing. Equipment failing, not meeting client expectations. Maybe I’d miss a crucial moment at a wedding or work with a problem client.

There was one difficult customer I had (I was lucky for the majority of my freelance career). It was the first time I worried a situation could escalate to something more. Whilst it was a stressful situation to handle, there was a lot of comfort in knowing that I had insurance if it did escalate.

There would be a team of legal experts to help me and a policy to cover my defence costs. Even though the situation diffused after some time, that one difficult client—and the fear and anxiety I felt whenever I received communication from them—was worth the £300 I had paid for insurance that year.

I had a small audience to launch to

I had previously launched Insurance by Jack (I’ll talk more about this later). Whilst this project wasn’t a success, hundreds of people had submitted quotes which gave me a lot of data to analyse.

I surveyed every quote and noticed an overwhelming amount were from freelancers. This was clearly something they were interested in. It also gave me a small audience to launch With Jack to.

Most insurers target every type of business

There weren’t a lot of options on the market for freelancers. The incumbents that have a monopoly on business insurance target sole traders, limited companies, traditional tradesmen, digital trades, high-risk careers like financial advisors etc.

It felt like there was a gap in the market for somebody to say, “We do this one thing really well for this one group of people”.

I like freelancers!

Having previously worked in buy-to-let insurance and selling to landlords, I realised it was important for me to like the audience I’m serving. I measure this by asking myself;

  • Would I have coffee with them every day?
  • Do I enjoy chatting to them?
  • Am I interested in what they’re working on?

If I can answer ‘yes’ to those questions it’s the right fit for me as a founder. Justin Jackson has a great article on founder / market fit.

The importance of positioning

We’ve established that With Jack isn’t doing anything innovative. What it does a good job of is positioning. This means freelancers feel With Jack is unique to them.

Take these tweets as an example.

Only offered in UK currently but this is the kind of insurance I want for freelance work in the US.
Got super excited about this until I saw the .uk extension.
We need a service like this in the US—freelancer insurance.

With Jack specialises in professional indemnity insurance. This product does exist in the US and elsewhere in the world. It has existed for a very long time.

What’s confusing people is the terrible job insurers do of positioning. Remember, most insurers are trying to be everything to every type of business. They cater to large businesses with employees and complex risks the same way they’re catering to sole traders turning over less than £50K per year.

People are unaware this policy exists in their line of work because insurers take a product (in this case professional indemnity) and package it for lawyers, SME’s, freelancers and more.

These are all different sizes of businesses across different industries with different needs and risks. This leaves the messaging of how this product can help you lost, unfocused and—you guessed it–not relevant.

This is why positioning is important. Not just in insurance, but any business. It helps you speak directly to a particular group of people.

If With Jack was targeting plumbers as well as web developers, our messaging would be muddled. We’d be sharing stories about burst pipes as well as the dangers of scope screep. There’s no crossover and—as a result—our messaging wouldn’t ‘speak’ to anyone.

Web developers would visit the website and think, “I’m not doing manual labour. This product must not be for me”. Tradesmen would visit the website and think, “I’m not building features for a client’s app. This product isn’t for me”.

The result? Fewer sign-ups.

In the latest episode of Build Your SaaS, Justin and Jon are exploring what to charge for their podcast hosting app. They’ve been looking at how competitors price themselves and their differentiator.

Rob Walling, co-founder of Drip, offered advice on charging more than your competitors. First, you can have features that no one else has. Secondly, you can position yourself differently by saying: “We are the podcast host for businesses”.

Justin acknowledges the successful job ConvertKit did of positioning themselves.

Your positioning matters a lot. Is there a huge difference between Nathan Barry's ConvertKit, which is email marketing for bloggers, and MailChimp, which is email marketing for whatever. Is there a big differentiator? No. A lot of it is the language they're speaking.

ConvertKit is now doing $1,000,000 MRR. They carved a niche as email marketing for professional bloggers, and have evolved their positioning to email marketing for creators.

At With Jack, being clear on our positioning allows us to build a customer experience that’s easy to navigate, use content to deliver a focused message and offer the neccessary products to our target audience.

Positioning is scary. Trust me, I get it

Before With Jack there was Insurance by Jack. When I launched Insurance by Jack, I was trying to target lots of different businesses. Creative agencies, technology start-ups, freelancers and more. I was terrified of excluding people and losing sales. There was nowhere on the site that actually said who Insurance by Jack was for.

It’s no coincidence that Insurance by Jack never gained traction.

Lesson: Start by focusing on the tiniest audience possible. It doesn’t mean you’re stuck serving that tiny audience forever. Mark Zuckerberg launched Facebook for Harvard students and it’s now at 2.19 billion monthly active users.

It’s easy to think that by launching to more verticals you’ll increase sales. You might attract more people through the door, but it’s tricker to win them over.

A freelance web designer should feel like With Jack has been built for them. They should feel like we understand the challenges they experience as a designer, and have stripped out all of the crap so they can get the insurance they actually need, quicker.

Philip Morgan, a consultant who specialises in positioning, says that when you define your positioning you are making a claim of expertise. So, what do you want to be an expert in?

Our statement is that we understand freelancers and the kind of problems they face with clients. Because of this we can offer them a product (professional indemnity insurance) to solve those problems.

Other insurance companies insure 300+ industries and sectors. But being the insurer for all businesses means people don’t know what products to buy, if they’re applicable to them and how they serve them in their line of work.

Again, this isn’t exclusive to insurance. All businesses should be positioning themselves to occupy a niche.

Final thoughts

Positioning focuses your messaging, marketing, customer service and products. With Jack isn’t doing anything innovative (yet!), but we’ve done a good job of the above which is how I’ve been able to organically bootstrap to almost 300 customers.

It can be scary because you’re worried about excluding potential customers, but by positioning yourself to a tiny audience you’ll know things about your customers’ needs and problems that competitors don’t. This will give you an advantage. From there you can gain access to other ideal customers.

Positioning doesn’t mean you’re locked into serving that audience forever, but it’s a great place to get started. You’ll gather feedback and learn from your customers, helping you build a truly great product.

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Bootstrapping Niice to 100,000+ Users

Bootstrapping Niice to 100,000+ Users

A few years ago, when great conferences like Build and New Adventures existed, I met Chris Armstrong. We became friends and have sporadically kept in touch over the years.

Chris went onto bootstrap Niice—a tool that facilitates creative discussion within teams—to over 100,000 users. I’m bootstrapping With Jack and felt I could learn some lessons from Chris. A 1 hour discussion on building and bootstrapping Niice was born.

Here are some things I learned from my chat with Chris, but I recommend you listen to the whole conversation.

  • Chris built Niice—which started as a side project—in one week to scratch his own itch
  • He built it quickly because momentum is everything. He found that having a working prototype to show a developer helped them get excited about working on it with him. His developer was able to jump in quickly and fix the bits he couldn’t get working
  • The idea for Niice was sketched on a plane from Toulouse on Monday. Chris launched it the following Monday
  • It was a modest launch, but it was enough to validate the idea
  • It took 2 years before Chris could dedicate full-time to it (he now has a small team working on it)
  • At some point Niice shifted from an advertising model to subscription model. The advertising model wasn’t great for advertisers as people didn’t use Niice to click an ad and be taken elsewhere
  • Chris launched at 2.30AM and quickly made his first sale. He’s since become friends with his first customer, Mark, and has lunch with him when he’s in the USA
  • To Chris, bootstrapping means slow but sustainable
  • His goal isn’t to get rich. It’s to have freedom
  • Chris says that being in business is being able to pay your bills. It doesn’t matter what the rest of them (competitors, other startups) are doing
  • Initially he wasn’t sure what problem he was tapping into. He figured that out as the app developed by speaking to people and building new features
  • Niice had 100,000 visits in the first month of launch and was covered in The Next Web. Growth has been organic
  • You don’t know what will resonate with people, so keep building stuff and get it out there

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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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