Why I'm Bootstrapping

Why I'm Bootstrapping

At some point this year I started considering investment. The initial build of With Jack was funded with my own money (money I’d earned photographing weddings at the weekend).

I liked the idea of bootstrapping. The investment scene mystified and intimidated me, but bootstrapping had its downsides. It meant taking short cuts, iterating slowly and being limited with marketing experiments.

Taking Short Cuts

A lot of With Jack’s tech was built on a shoestring budget. Some of it’s a quick fix to get the job done. It’s fine at the moment with just me working on Jack, but once I grow it’ll get complicated and have to be reconsidered.

Iterating Slowly

I don’t have the budget to match my ideas. That’s frustrating. When bootstrapping you have to ruthlessly prioritise. You don’t have the capital to explore every idea. Even the process of iterating on one feature is slow. I’ve focused on the onboarding process, but there are features for existing customers I’d love to build.

Limited With Marketing Experiments

Most of With Jack’s customers have come from organic search, word of mouth and referrals. Not having a pot of cash to dip into means being limited with marketing. I’d like to experiment with conference and podcast sponsorship, but it isn’t cheap.

My numbers have been consistent from day one. 10-12 sign-ups a month. Retaining 83% of customers come renewal. But I hit a plateau. I didn’t have the capital to reach more people and With Jack’s product wasn’t evolving as quickly as I’d like.

That’s when I applied to join an accelerator. A £25,000 cash injection with connections to the investment scene, meaning there was the option to raise more if needed.

(At the crux of it, I was excited to tap into the mentor’s experience and meet like-minded people. That was my priority and the accelerator delivered on that front.)

Truthfully, I was never fully committed to the idea of investment. Even during the application process I wasn’t sure if it was right for me. It was more of a, “Let’s dip my toe in and see what happens” vibe. But before I knew it, I had drank the Kool-Aid and got sucked into startup mentality.

“A lifestyle business isn’t good enough.”

“You have to think bigger and be more ambitious.”

“Not getting funding means you’re not good enough.”

“You need to disrupt an existing business model.”

These were just a few of my thoughts.

As well as the cash injection I wanted validation. Getting investment was like somebody saying, “I believe you can do this”. After years of insurers rejecting working with me, my fragile ego craved validation.

But I didn’t get investment.

After the initial disappointment I felt OK about it. No, really. I trust the accelerator. I respect the people who made that decision. I understand why they passed on investing. It wasn’t right for them… and in hindsight it wasn’t right for me.

Side note: You may be wondering why I didn’t get investment. I think it was down to being a solo founder, not solving a big enough problem and being unclear on where the £25,000 would go. I’m sure there were other factors, but these are the obvious obstacles.

I had no desire to apply for other accelerators. I’d been on the fence about investment, so when it fell through my thoughts turned back to bootstrapping.

Why I'm Bootstrapping

I realised I’d prefer turning my attention towards getting 1000 true fans.

I realised the funding process isn’t for me. I’ve spoken to my friend, Cally, at Mallzee about this (they’ve raised over £4 million). Taking time away from work and exhaustive travel wouldn’t make me happy. I like working from Glasgow, having my routine and hanging out with my dog.

I realised I want to figure things out in my own time and retain control, instead of having strings attached and scaling quickly to satisfy investors.

I realised I want to focus solely on my customers. Not on VC’s or getting wrapped up in the insurtech bubble. To be laser-focused on the people that will make With Jack profitable.

Above all else, I realised I didn’t want to disrupt an industry. I want to pick a small corner of the web that I can call mine and build something great.

That’s it.

What Do I Want To Achieve?

Building something profitable and of value for thousands of happy customers.

I still have an internal struggle. I wonder if I’m taking the easier option (although nothing about this journey has been easy). I feel bad about myself for not maxing out my ambition. Especially as—with no family or children—I’m in a position where I can take more risks.

But then I go back to what success means to me.

Success is crawling into my bed at the end of the day feeling creatively satisfied and challenged. Currently, I feel that way most days.

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A Week In The Life Of…

A Week In The Life Of…

I enjoy reading other people’s ‘week (or day) in the life of’ posts to get a glimpse into their routine, so I micro-blogged every day last week. No week is the same when building a business, but how did last week look as a one-woman, bootstrapped business?


Monday and Friday are my favourite days of the week. I’m excited about the week ahead. There are still a lot of unknowns at this stage in my business. Whilst that would scare some people, I see it as an exciting time.

This particular Monday was interesting as it began with a shot of champagne. This doesn’t normally happen, but one of the businesses in my co-working space secured money to launch their product.

I made an ‘Insured Via’ badge for our customers. This is a badge they can display on their site to show clients, potential clients and visitors they’re professionaly insured. To my surprise a customer immediately adopts it!

A proof of insurance badge

I had a call with From Scratch who is working on With Jack’s copy. The current site doesn’t convey the value With Jack provides freelancers or the problem we solve. Sabine is helping me hone my message (a piece of advice drilled into me from Ignite).

I also finished watching the last of the InsurtechCon videos on YouTube. I watched every one of them to get an idea for where the UK insurance industry is headed.

In the evening I attended Tech Masterclass at Glasgow University. Rachel Evatt, who sold her startup to Skyscanner, was speaking about creative courage. I get a lot of value out of these masterclasses and use them as an opportunity to ask questions and seek advice.


I have a few copies of Learn From Great Design in my arsenal, so decided to run a giveaway through With Jack. My thinking here was purely traffic-related. A quick win (or so I thought) to get more eyeballs on the site.

It took time to get the landing page right, but one of the Slack groups I’m in provided critique (thanks!). For the amount of effort I put into this, however, it was a total flop.

Today was also about budgeting. I sent From Scratch, my copywriter, an email with the budget for writing With Jack’s copy. Budgeting is hard at this stage. I’m bootstrapped, early stage and a one-woman band, but I’m also open and transparent about money with any of the freelancers I work with.

One of my customers has built a forecasting tool. We worked out a special deal for With Jack customers and added it to the growing list of benefits. Having this kind of collaborative relationship with my customers makes me happy.

Another sociable evening. A photography group I’m a part of has their ‘end of wedding season’ party tonight. We meet in a pub, drink a few rums and talk shop.


Gah. Today I woke up with sore throat and cold symptoms so I worked from home. I wasn’t as productive as I am in the office and mostly used today for research purposes. There’s a new direction I’m flirting with for Jack.

For someone who likes technology and design, I’m not sure why it took me up until now to sign up to Tide—a business current account packed with powerful tools. First impressions: Why have I been using my crappy, dinosaur bank for so long?

I sent some cold emails today. I haven’t had any success with this so far, but I only do it when I genuinely stumble upon a business I’d like to work with and think would be a good fit. It’s probably strange for them to receive an email saying, “I really like your work. Let me arrange insurance for you!”.

Tonight I was supposed to attend GAB, my favourite meet-up. Feeling sniffly I decided to stay indoors. Instead I worked on clarifying my message after listening to How to Tell People What You Do in 3 Easy Steps.


Out of the office today. I’m visiting my old high school in Dunoon! Since leaving school 14 years ago I haven’t given much thought to education. That was until a couple of weeks ago when I gave a talk at my old school.

It made me think how powerful it is to have a positive impact on even one student’s career or attitude. Today I’ve returned to judge the YPI final alongside ex-pupil Sam Coley. Sam now runs a startup TickX.

The winners of YPI!

Apparently my old school has a poor uptake of girls with computing, so I’d like to get involved in addressing that.


I’m currently going through the Ignite programme. Well, kind of. I didn’t get investment or fully onboarded, but I’m attending the monthly off-sites in exchange for creating content for them. Today I edited and uploaded my latest Ignite video, so I’ll be sharing this on my YouTube channel come Monday.

I’ve been working with Catch Media, another of With Jack’s customers. Catch Media is managing my Twitter and Facebook ads, so I sent them copy and assets. It’s scary delegating tasks (and spending the money), but it frees me up to focus on other things. Everybody keeps telling me I can’t do everything alone, so I’m taking their advice onboard.

The Learn From Great Design giveaway came to an end. What a flop. I have 10 copies and only 5 people entered—so they automatically win. What should I do with the 5 remaining copies?

I end Friday with a few boring tasks. Catching up on email, going over analytics, sending payments to suppliers.

Now it’s time for mulled wine at the Christmas market.

Mulled wine at the Christmas market

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Beating Shiny Object Syndrome

Beating Shiny Object Syndrome

It took me over 2 years to launch With Jack. Here are three reasons why:

  1. Insurance is a regulated industry, but it was a minefield for me to navigate. I had trouble knowing how to even get started.
  2. Insurers didn’t want to work with me. I had no existing customers or any indication I could build a successful business. I also had no money to fund it. This was a red flag for insurers.
  3. I wasn’t focused enough.

Today I want to write about number 3. Not being focused enough. Or in my case, executing on so many of my ideas that I was being pulled away from my ultimate goal; to launch With Jack.

Here are just some of the projects I was working on:

  • Wedding photography
  • Weekly podcast
  • Gaming blog
  • Photo course
  • SaaS app for landlords
  • Photo walks

The list goes on…

A list of my projects

I had all of these projects that I was giving a little of my time to. I wanted to build and launch With Jack, but I wasn’t putting 100% into it.

I thought I was, but in hindsight I was giving 5% to one project, 20% to another etc. What did this leave for With Jack?

I was good at dreaming up ideas and executing on them. I thought this was something to be proud of, but now I realise it was holding me back. We all have a limit of time, energy and focus. Having so many projects meant spreading myself thin.

I was owner of a bunch of half-baked projects or inactive domains that never had the commitment they need to become great projects.

Maybe you are, too.

Ideas need an extraordinary amount of work behind them to become great projects. An extraordinary amount of work. Unless you’re Superhuman, you can’t do that with 3, 4 or 5 projects on the go. I wish I’d learned that earlier.

Two unrelated events brought me to this conclusion. It first struck me after reading about Nathan Barry’s experience. His product, ConvertKit, was failing and he was considering shutting it down. Instead he decided to focus on it full-time.

What resonated with me was the following quote from Nathan’s post on growing ConvertKit to $30,000 in monthly recurring revenue.

“Have I given my company every possible chance to succeed?” If the answer is no (as it was for me), then truly give it everything you have.

And look at ConvertKit now.

Secondly, getting admitted to hospital with pneumonia caused me to reconsider where I was investing my time. I love my life and I’m very lucky, but one of my businesses was failing and the other wasn’t even up and running. I was stressed and my body was trying to tell me something.

Realising this, I culled my personal projects and gave With Jack my full commitment.

I don’t have anything against personal projects, and I’ll certainly come back to some of mine in the future. They’re great for learning a new skill or figuring out what you enjoy doing. But they played a vital part in holding me back from launching.

With Jack still doesn’t yet have 100% of my focus. Due to a lack of funding, I’m still juggling wedding photography with building With Jack (wedding photography has funded a lot of my development costs).

Ruthless Prioritisation

Once I’d culled my personal projects, I saw a big difference in my output with Jack. This was when everything changed for me. The results spoke for themselves.

I sat (and passed) my first insurance exam. I flew to London and met the person who would help me launch my business. Three months later With Jack was live. A little over a year later I have 150 customers.

Ruthless prioritisation is where the magic happens.

We’re creatives, we’re makers. We come up with new ideas and—because we have the skill set to execute on them—end up being pulled in different directions.

Are you guilty of shiny object syndrome? Are you owner of a bunch of halk-baked projects or inactive domains? My advice is to pick one idea, give it the resources it needs to become a great project and cull the rest.

Each idea needs an extraordinary amount of work behind it to become a great project. Understanding that and realising I couldn’t do that with multiple projects is what helped me beat shiny object syndrome.

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Speaking At Web Dev Conf

Speaking At Web Dev Conf

Last week I gave my talk, Idea to Execution and Beyond, at Web Dev Conf in Bristol.

Side note: Web Dev Conf is one of the friendliest and funniest conferences I’ve attended. It’s an annual event, so make sure you attend next year.

This was the first time I’ve delivered this talk. My aim was to give a high-level view of building and launching something, drawing from my experience of building With Jack.

I covered the idea stage, build process, what to expect when you launch and what happens after you launch. Specifically, I spoke about topics such as idea validation, embracing transparency, shipping anxiety and customer development.

You can see the slides from my talk on SpeakerDeck.

Speaking at Web Dev Conf

Here are the resources I mentioned in my talk:

I compiled a Storify of the event and made a YouTube video of the experience.

10/10. Would Web Dev Conf again.

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A Look Back On With Jack's First Year

A Look Back On With Jack's First Year

Last week I cleaned out my home office and found a post-it note from 2013. It was a scribble of the insurance company I wanted to build, forming the basis of what would eventually become With Jack.

My post-it note of the insurance company I wanted to build
  1. It needs to be human.
  2. It rewards loyal customers.
  3. The technology doesn’t suck.

I remember writing that note. I was working from Toad’s Caravan at the time and fed up of being in buy-to-let insurance.

That business impeded my creativity. While there were challenges in insurance I wanted to solve, I was itching to work on something that would allow me to be more, well, me.

This nostalgia ties in nicely with the fact it was a year ago today I launched With Jack!

Although I’d soft-launched a few weeks earlier to iron out kinks, I was now opening up to the public. This was a long time coming.

For years I’d been in a flux of one step forward, two steps back. Usually when I launch something there’s a degree of shipping anxiety, but I felt elated to get With Jack out into the world. I was so ready to devote myself to this.

12 months down the line, how does With Jack look? Well, it’s starting to look more like a business!

  • 135 customers
  • £36000+ gross premium written

Provided my customers stay with Jack come renewal time, I’ll see revenue double. Year two is magical for brokers and I’m excited to feel the effect of that on my cash flow!

Top Sources of Traffic

  • Organic search
  • Twitter
  • Designer News

The traffic that converts the best is:

Organic search has been performing well recently. With Jack is now on the first page of Google, sandwiched between my big competitors (and the insurers who passed on working with me).

Google—as we all know—involves playing the long game. A year of creating content like this is paying off.

Although Analytics can’t display this data, I’ve seen a lot more customers coming from recommendations through Slack. Technology and design communities are big in Slack, and this is the audience With Jack targets.

An avenue I’ve just started experimenting with is YouTube. A few weeks ago I launched a YouTube channel intended as a weekly insight into my work.

It’s too early to gauge if this is a good marketing channel, but the reaction has been positive and I’m enjoying learning something new (filming and editing).

On the topic of learning something new, I thought I’d find taking up video frustrating because I’m just learning and not very good at it. It was important I gave myself permission to ‘be crap’ in the beginning while finding my feet. That’s what’s enabled me to dive in with YouTube—this acceptance that it’s rough and doesn’t need to be perfect.

Paid Ads Suck

I keep learning this the hard way.

The last update I did on Jack’s figures, I had just paid for a sponsored post on a design blog. I was apprehensive about this because—from all the marketing I’ve done—the free tools I’ve built, recommendations and presence on Twitter convert the best. Paid ads always left a bad taste in my mouth.

“Maybe this time will be different”, I thought.

It wasn’t.

I don’t think insurance translates well to ads. You’re only shopping for insurance when it’s something you need—not something you see and think, “That would be nice to have”.

My Highlights of the Year

  • Winning The Rookie Award at the Digital Insurance Awards.
  • Meeting my customers. With each city I’ve visited in the UK, I’ve made a point of meeting my customers. Katherine, Rachel and Mikleo in Manchester, Martin in Newcastle, and Sabine and Rohan in Glasgow.
  • Applying to an accelerator. I didn’t get investment from Ignite, but attending the monthly off-sites has provided me with so much value. Being around other founders, learning from other startups… it’s been invaluable.

What's Next?

Instant quotes.

For the last year I’ve been manually processing quotes. It’s nice being in the trenches with my customers, but I know from customer development that people want instant quotes.

Side note: For customer development I’ve started using a neat tool called Iterate.

I won’t bore you with the logistics of why we haven’t implemented instant quotes, but things are moving in that direction. Scott is mocking up the customer journey as I type. However, in the insurance world this could take a while to roll out…

Ultimately, I want to build the best suite of tools for freelancers to buy and manage their insurance. This requires money and I’m self-funded. I didn’t get investment from Ignite (more in that another time), so weekend photography jobs are funding the development of With Jack.

I’ve had to ask myself how serious I am about this and how much I believe in what I’m building. The answer is “100% serious”. Now I’m weighing up my options for putting money into With Jack.

Getting to 135 customers with no money and bootstrapping as a solo founder is good validation, but now it’s time to up the ante.

Thank you to my 135 customers who have supported With Jack and are helping to shape insurance for freelancers.

Follow With Jack

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