My First 100 Customers

My First 100 Customers

9 months ago I launched With Jack.

This wasn’t my first launch. I’ve shipped a few projects over the years;

  • A podcast
  • An email course
  • A SaaS app
  • Insurance by Jack
  • A vlog (coming soon)

Each launch had varying degrees of success, but one thing has always struck me. Launches are unpredictable and often underwhelming.

I used to expect big things from launches. “This is it. This is the idea that’s going to take off. It’s a guaranteed win.” After a while I learned to scale back my assumptions and have more realistic expectations.

When it came time to launch With Jack from a hotel room in Berlin, I didn’t set expectations. Yes, I’d spent years trying to get it off the ground and invested thousands of pounds into it. The stakes felt high. But I wanted to quietly push it live, iterate on it every day and see where it could go.

Where Can It Go?

Today I reached the 100 customer mark.

To say I’m excited is an understatement! 100 isn’t a sustainable business, yet it’s a milestone that validates I’m headed in the right direction. If you can get 100 customers, you can scale beyond that to 200, 400, 1000 etc.

Simply getting to launch day was a hurdle. Reaching 100 customers is… I can’t describe it. It makes me feel optimistic. Like this idea for Jack has potential. It’s got legs.

How Did I Get 100 Customers?

All the feels and past disappointments aside, how did I get 100 customers?

  1. Networking
  2. Referrals
  3. Twitter
  4. Leads from Jack’s MVP
  5. Organic search

Networking

It’s no surprise that relationships have had the biggest impact on my business.

With Jack targets an audience of creative professionals. 70% of my customers are web designers and developers, and the rest are a mix of graphic designers, photographers, copywriters and more.

Years ago—before With Jack was conceived—I took an interest in the web industry. I was fascinated with web design and learned to code.

To learn more about web design and development, I started attending conferences. I read web industry publications and followed designers and developers on Twitter.

Sean McCabe suggests building relationships now for the business you’ll be building in 3 years.

This is what I was doing, albeit unintentionally. I didn’t have anything to sell, I just really liked the web industry and found these people fun to hang out with.

Socialising at industry conferences
Being sociable and making new friends at conferences. Photo by Filly Campbell.

Every year I’d travel to New Adventures in Web Design in Nottingham or Build in Belfast. It was through networking at these conferences I met people I’m still friends with today. Many of these friends became With Jack’s first customers.

Lesson: Take Sean’s advice about building relationships now. Pick an audience you like, focus on helping them and grow your network. Start with people.

Referrals

Referrals are the strongest indication you’re doing something right. Every time I hear, “My friend got their insurance through you and recommended your service” it’s proof With Jack is on the right path.

What’s worked with Jack is being laser focused on a specific audience.

Most insurers tend to target every type of business. So their web site copy and marketing material is trying to appeal to, say, traditional tradesmen and digital businesses. It’s hard to make that work.

When a designer or developer asks for business insurance recommendations, With Jack is often suggested. This is because our marketing, copy and customer rewards are all aligned with that particular audience.

Jack immediately pops into their head instead of ‘that insurer that offers every type of insurance for every type of occasion’.

Lesson: These referrals came my way without prompt or actively encouraging them. I think referrals happen when you do something well and are generally just helpful.

Twitter

When I say Twitter I’m not talking about sponsored tweets (that’s no.7 on the list), but from being active on Twitter for the past decade.

Wow. For 10 years I’ve been tweeting about the video games I’m playing and what lunch I’m eating.

On a serious note, I joined Twitter in 2007. Back then there was no With Jack. I was unhappy in my job and had never owned a camera. I was a hardcore gamer with an anxiety disorder.

Over the years, people have followed my journey in insurance through Twitter. The idea of improving technology in the insurance industry. Building my first quote system prototype. Starting to get invited to speak at conferences. Launching Insurance by Jack (and that not doing so well). Trying to find an insurer to come onboard with Jack. Being totally burnt out and admitted to hospital. Passing my first insurance exam. And finally launching With Jack.

Inviting people on this journey with me has been invaluable. Not all of them are in the market to become Jack’s customers, but for those who are they feel like they’ve gotten to know me. They want to support the business I’ve worked hard to launch.

Lesson: Document your journey. Twitter isn’t a platform that will work for everyone, but I got on it early and became an active user. It can be uncomfortable sharing the vulnerable moments. It’s easier to show up when you’re financially stable and have 10,000 customers, but I think being transparent about your journey and involving people in it will help you get there quicker.

Leads from Jack's MVP

In May of 2014 I launched Insurance by Jack. I’ve described this as my MVP, but I’m in two minds as to whether I should have ever taken that route. (I’ll write a post dissecting where and why this business went wrong. Subscribe to my newsletter if you don’t want to miss it.)

I did a lot of brand damage with this business. I had a website that did a great job at communicating my vision, but fell short where it actually mattered. Delivering on that vision.

People came to the web site with certain expectations, but those expectations weren’t being met. People’s first experience with Insurance by Jack was poor—and first impressions matter.

On the other hand, some of the people that stumbled upon Insurance by Jack took an interest in where it could go. They signed up to the newsletter or became followers on social media. Some of those leads are now With Jack customers.

Speaking about Insurance by Jack
Speaking about taking a chance with Insurance by Jack, and how it may not be a success but a stepping stone to something else. Spoiler: It wasn't a success, but it was a stepping stone to what became With Jack.

Lesson: Although I’m disappointed that Insurance by Jack delivered a poor first impression, it served a purpose despite its imperfections. I got a lot of mistakes out of the way and drummed up interest from people that would later become customers.

Organic Search

Organic search has been great for bringing people outside of my network to With Jack. As Jack becomes more of an established brand, I think I’ll see more customers come via this channel.

Currently, the customer journey via organic search looks like this:

  • Somebody searches for an answer on Google
  • They find one or two of Jack’s articles
  • They like the brand
  • They get a quote
  • They become a customer

Jack’s rankings will only improve as I write more content. I use Answer The Public to discover what questions people are asking, then I create blog posts or landing pages around it.

Again, because I’m focusing on a specific audience it’s easy to find out what to write about. I can learn what confuses them about insurance and use examples that hit home.

Lesson: I don’t think I need to tell you the value of ranking in Google with valuable content. Your audience is searching for answers. By providing value, you build trust and potentially win customers.

The List Goes On…

I’ve covered the top 5 channels, but there are many more that have brought me customers.

  1. Public speaking
  2. Promoted ads on Twitter
  3. With Jack's beta testers
  4. Designer News
  5. Podcast appearances
  6. Product Hunt
  7. A blog post about chat bots

I think getting to 100 customers boils down to a few things.

Finding An Audience You Want To Serve

One of the reasons I couldn’t make a success of my Dad’s insurance business was that it served an audience I was disinterested in. You’re going to be hanging out with these people, talking to them and getting into their heads. If you don’t see yourself having coffee with them every day, it’s not the right fit.

Keeping It Simple

If I was to follow industry trends, I’d have launched with a similar format to other insurers. Multiple providers, different types of cover and aiming to appeal to every type of consumer. Instead I worked with one provider, offered one product and catered to a specific group of people. This approach meant I could launch quicker and with less capital. It also helped with tailoring Jack’s customer journey to a particular group of people. This makes the experience as good as possible for them, which leads to happy customers and referrals.

Figures

Lastly, I will leave you with some stats.

  • 21,992 visitors
  • 291 quotes
  • 100 customers
  • £24879.53 gross premium written

Here's To The Next 100?

I believe I can scale this business, but I want to take a moment to appreciate getting to 100 customers.

In business you always look forward. “Okay, we launched. What’s next? Okay, we have 100 customers. How do we get to 200?”. But this milestone is one I want to savour. It took so bloody long to get here.

Thank you to each of you who have used Jack to arrange your insurance.

read more

A Few Updates…

A Few Updates…

Since launching With Jack I’ve stuck to semi-regular updates. Usually I write a blog post every fortnight or so, but life got in the way.

Here are some of the events that took priority over blogging:

  • My dog got sick. A cancerous tumour followed by pancreatitis. I’m really attached to my dog, so that sucked
  • Wedding season kicked off. I’m still shooting weddings so I have funds to put into Jack
  • Traveling. I flew to South Uist for an island wedding and visited England to film a segment for Right on the Money

Now that my dog’s better and I have no more weddings until July, I have a couple of (relatively) uninterrupted weeks to get back into my routine! Let me fill you in on what’s been happening.

Improvements To The Onboarding Process

It’s funny looking back on the first few months of With Jack. The only part of the process with any polish was the quote system. Beyond that it was scrappy, not to mention I was only offering one product.

I’ve enjoyed iterating on With Jack since its soft-launch in August. First by rolling out new products based on what customers were requesting. And now by polishing the rest of the onboarding process—the risk questions.

For those that haven’t yet used With Jack, the current process looks like this:

  1. You submit your details via our quote engine
  2. Jack emails you a breakdown of your quote
  3. You answer your risk questions
  4. Jack sends you your policy documents

For launch I invested my resources into step 1, the quote system. This is With Jack’s bread and butter. For step 3 we threw together a form without too much thought. It didn’t take long to notice it was causing confusion.

These were some of the questions people would ask at the risk questions stage:

“Is this the final step? Am I committed to buying insurance? How do I pay?”

I worked with Naomi Atkinson on redesigning the risk questions. We specifically addressed the above confusions and rolled out the updated form last month.

Here’s the before and after:

A before and after of the risk questions form

Aesthetically it’s a lot better, fitting Jack’s whole ‘design at the core’ ethos. More importantly—since implementing the new design—I haven’t heard any of the above questions.

Mission: Accomplished.

Inching Closer To 100 Customers

The next blog post I publish will be celebrating hitting the 100 customer mark. (I hope.)

Right now I have 95 customers. This means I’m a 1.5 weeks away from the big 100! That is unless I have a surprisingly good or horribly slow fortnight.

With Jack is about much more than the numbers, though. I could have 10 customers and it would still have the same mission—getting creative businesses the protection they need, doing so with as little hassle as possible and in a format that’s simple.

With that said, I can’t deny that getting to 100 customers as a bootstrapped, solo founder feels great.

This nicely ties into my next update…

I've Applied To An Accelerator

I did something I never thought I would. I applied to Ignite, an accelerator.

Let me back up a bit.

A few months ago I attended a startup dinner in Edinburgh where Tristan (Ignite’s CEO) was a guest. Tristan and I have met before, but this was the first time I asked if Ignite would be a good fit for me.

As much as I want to champion bootstrapping and love the idea of being a solo founder, I’m struggling with building Jack on my own. It’s growing very slowly. I feel I’d benefit from a network, mentorship and being around other startups.

I’m not comfortable with accelerators (mostly because I like hiding behind my computer). But if something scares me, it’s usually a good indicator I should try it.

I had my video interview last week. I’ve since been invited to the last stage of the application process in Newcastle. This is what determines who is accepted into the final programme.

Fingers, toes and eyeballs crossed.

read more

A Look At Jack's Figures 7 Months In

A Look At Jack's Figures 7 Months In

3 months ago I wrote Jack’s year in review post. This was after only 4 months in business—1 of which was a soft launch. After putting my 81st customer on cover this week, I looked at some of the same figures that lead to that post.

Three months ago, my figures looked like this:

  • 16,449 visitors
  • 153 quotes
  • 41 customers
  • £10293.93 gross premium written

Today, they look like this:

  • 19,482 visitors
  • 247 quotes
  • 81 customers
  • £20377.29 gross premium written

Traffic has dropped considerably, which is inevitable after the buzz of launch day fades. So have the number of quotes I’ve processed. Despite this, my conversion rate has improved and I’ve generated another £10,000 of Gross Premium Written.

I wanted to gain a better insight into these figures. I’m putting the same number of people on cover despite a drop in traffic and quotes.

I took to the solo founder group I’m a member of and asked why they thought this was.

The consensus is:

Insurance is a yearly purchase. Much of my audience wouldn’t have been ready to buy insurance initially as they had existing policies.

Secondly, Jack’s launch garnered interest from a user base that isn’t my market (geographic eligibility/fit the criteria). It also exposed Jack to people who are my market and used us to arrange their insurance. They now follow Jack on social media or recommend us to their friends, exposing us to more of our target market without the same footprint as launch.

Our overall footprint is smaller, but our target market footprint is bigger.

This sounds right. More than 50% of my visitors have come from the States. (I still receive quotes from people outside of the UK—even thought it’s a .co.uk. domain and the currency is in GBP—but fewer than before.)

I’m also seeing more sign-ups through recommendations. I’d love to encourage this behaviour with a referral program.

Top Sources of Traffic

Three months ago, my top sources of traffic were:

Today, they look like this:

  • Designer News
  • Organic search
  • Twitter

I’ve been focusing on creating content, so I’m happy to see organic search performing well.

What I’m more interested in is traffic that converts. Whilst I stupidly didn’t track this from day one, I have Goals set up in Analytics. They monitor my CTA click-throughs and those who complete a quote and submit their details.

The traffic that converts best is:

Jack's Strategy

When I launched Jack I had no idea what would work. I still don’t. But 6-7 months in I’m building a better picture of where to focus my time, energy and money.

Content is performing well. I think this is because most insurers don’t cater their content to creative professionals. They can tell you why a tradesman needs insurance or a solicitor, but not a web designer or developer.

Some of the stories I’m sharing about insurance for creatives invoke action or plant a seed. I’ve just paid for sponsored content on a popular blog, so it will be interesting to see how that converts.

I also built a tool that generated more quotes in 2 days than the entire week before. Few of these have converted yet, but I’m hoping there’s a delayed effect and it’s a slow burner. The response to the tool has been positive.

Check out those RT's!

As the months progress, I’m hoping less of my marketing will be guesswork and more decisions will be informed by data.

Something tells me, however, that it doesn’t matter if you’re 7 months or 7 years in—marketing is a constant experiment and full of surprises.

read more

What Does Validation Look Like?

What Does Validation Look Like?

As With Jack has been live for 6+ months, this is a question I’ve been exploring.

Whenever people ask, “How’s Jack going?”, I’m never sure what to respond with. Do I tell them how many customers I have? Focus on the conversion rate? Or do I be upfront and say “It’s going well, but it’s still not supporting me yet”?

Depending on who’s asking I’ll say a mixture of those things. “It’s going well. We have 73 customers and are growing every week, but it’s hit a plateau. We have a conversion rate of 25%, but it’s volume we’re lacking.”

To some this sounds like a promising start. To others, they seem sympathetic to my startup woes. This is because validation looks different to everyone.

To me, With Jack has been validated.

Here’s how I personally measure validation:

  • Creatively satisfied. I crawl into bed at the end of the day feeling challenged and creatively satisfied. Insurance isn't known for being a creative industry, but I bring those elements into my job. Making visuals, writing content, coding etc.
  • No Sunday dread. I'm not on Facebook anymore, but I'd log in on Sunday evenings to be met with a wall full of 'Sunday dread'. These are the people who aren't looking forward to work on Monday. There are 52 (or 53) Sundays in the year—that's a lot of dread!
  • Comparing it to my previous attempt. With Insurance by Jack, I won 55 customers in 2 years. Compare this to 73 customers in 6 months and With Jack is looking encouraging. It supports what I was saying all along. A better customer journey will delight visitors and improve the conversion rate.
  • Customer feedback. Emails, tweets. Every time someone vouches for With Jack, I feel a sense of validation. With Jack's goal is to make business insurance accessible to freelancers and those working in the digital sector. Statements like this affirm I'm closer to fulfilling that goal.
  • Making money. With Jack has been making money from day one, although it still isn't enough to support me. Every week we're putting new customers on cover and inching towards a sustainable business.

But maybe I wouldn’t think Jack has been validated if I had 3 kids to feed.

Maybe I wouldn’t think Jack has been validated if I’d left a job with a £60K salary to pursue it.

I’m fortunate that I’m building Jack with a financial cushion from other projects. This is why it’s impossible to have a blanket response to “What does validation look like?”. Everybody’s circumstances / goals are different, therefore validation looks different to everyone.

Playing The Long Game

Another factor I consider is time. It took my dad 2 years to start earning a decent income with his insurance business. (In case you haven’t noticed, my dad is a big inspiration to me. That’s who I named my business after.)

Year 2 is magical for brokers. On top of the new business they’re bringing in, they’re enjoying renewals from year 1. That book of customers begins to build.

Despite an insight into how my dad built his business, my mind wrestles with the articles I read on marketing and business in the startup world. You know the type. The ones with the clickbait titles?

“How My Website Made £17,000 With This One Simple Tweak”

“Idea To £25,000 In One Weekend”

“How We Got 100,000 Users In 24 Hours”

While they’re fun to read and (maybe) spark ideas to apply to your own business, they’re unrealistic. They make business sound easy. The overnight success story. My worry is people read these articles thinking that’s how business should look.

Nobody writes about “How It Took Me 500 Days Of Showing Up And Making Lots Of Mistakes To Earn Enough Money To Pay My Bills”. That’s partly why I blog about where I’m going wrong, because that part is just as important as when you get it right.

Side note: A business blog I enjoy reading that’s refreshingly honest is Adii Pienaar’s.

In 2015 I changed a lot about the way I do business. I used to follow my creative itch, starting a new project whenever inspiration hit. I’d then move onto the next thing when I got bored or lost steam.

That’s not me anymore. I’ve learned to focus. I give one project my attention, I experiment with it and I’m patient. I don’t expect overnight results.

To answer the question, “What does validation look like?”. You can decide based on your circumstances and goals. Ignore the clickbait headlines, how others measure their success and focus on what validation looks like to you.

Header icon is from Hand Drawn Goods, which is licensed under CC BY 2.5.

read more

Turning My Robbery Into A Positive Experience

Turning My Robbery Into A Positive Experience

Last month I celebrated my birthday in Geneva. While turning 30 in Switzerland, my home in Scotland was robbed.

The intruder broke in via my terrace door. He stole my PlayStation 4, 13 video games, iPad, sound dock, iPod Touch, my camera bag, which had a Canon 5D MK II in it, two flash guns, 7 CF cards and a 28mm lens. Yes, a lot.

If anybody was going to have insurance, it was me!

Working in insurance yet being on the consumer end has been an interesting experience. Going through the claims process, I made observations I can apply to my own insurance business.

An Easy Way To Know What You Own

Problem: Not having proof of purchase, knowing when you bought items, their value and the specific model. This can slow down the claims process.

When I made my claim, I was aware I didn’t have proof of purchase for a number of items and figured this could give my insurer an easy out. “We’re not paying for that item. You can’t prove you even owned it.”

I tried to provide evidence where possible. I have a freakishly good memory of dates. This came in handy for remembering when I bought items. I was able to search my bank statements and locate specific purchases.

If you’re with a good insurer, they’ll understand you haven’t kept a receipt for Wolfenstein: The New Order that you bought 3 years ago. A good insurer will honour the claim.

This is (one reason) why you shouldn’t choose the cheapest provider. Most people don’t trust their insurer, but I’d guess a majority of those bought the cheapest cover and got burnt. Not all insurance policies are created equal.

I digress. Relying on your memory for dates of purchase, what model you own and its worth won’t always cut it. It will also slow down the claims process.

Solution: An app for customers to itemise their contents. If ever they were to make a claim, they could easily select which items had been stolen or damaged without digging up receipts or product information.

This does pose another problem. Who can be bothered taking the time to file their contents? An incentive could be offered by the insurer for doing so, whether it’s cashback or a reward.

Digital Update On The Progress Of Your Claim

Problem: The process of making a claim is archaic. Phone a call centre, wait in a queue. Lame. I can quote and buy my insurance online, but that’s where the digital experience ends.

My insurer paid out for all of my stolen contents. One advisor even investigated the payout for my video games, thinking their colleague had wrongly price matched them against second-hand games. This is from an industry that’s associated with doing anything to get out of helping their customers.

Where it fell short, however, was the lack of communication. If I wasn’t chasing them up I had no indication as to what stage my claim was at. When your house has been burgled and your valuables have been taken, you want to know when you’re going to get your stuff back.

I come from a generation who hate speaking on the phone, so liasing with a call centre every few days was a nuisance.

What I really wanted was the ability to login to a dashboard and see what stage my claim was at.

  1. “We’ve received your claim”
  2. “We’ve appointed an electrical specialist”
  3. “Your electrical specialist is price checking your contents”
  4. “Your claim has been processed. We’re sending you a cash settlement of £3000”.

That kind of thing.

Solution: A dashboard for customers to login and have an overview of the status of their claim. I understand the phone can’t be avoided completely, but it’s uneccesary and time consuming for small updates as to what point you’re at with the claims process.

I had a pleasing experience with my insurer, yet I couldn’t help but make these observations. I’d love to apply my experience to Jack in the future. At least this robbery would have had something positive come from it.

Misc Notes

If you’re buying contents insurance these are some things to be aware of:

  • Make sure you have new for old cover. This means if your 10 year-old dSLR gets stolen, the insurer will replace it with the current model.
  • Inform your insurer of any high value items. If your £3000 TV is damaged, your insurer may not pay out because it’s a high value item you didn’t disclose. The more honest you are, the better. Don’t leave stuff out so your premium is cheaper.
  • Your work equipment won’t be insured under your home insurance, so ensure you have business insurance for your contents. According to Gartner, a laptop is stolen every 53 seconds! Coincendentally, Jack just rolled out the ability to insure your business contents.
  • I wrote a about my burglary from a business perspective on Jack’s blog. If your work equipment is stolen, can you still function as a business? What about back-ups? These were the questions I had to address when it happened to me.

read more