It’s been 12 months since my last blog post, my 2019 year in review. I don’t want this to be a traditional year in review, but I do want to document what it was like bootstrapping my business through a pandemic. 2020 turned out to be the most testing and lonely experience I’ve faced as a solo founder.

Expectation vs reality

When this all kicked off early 2020, my expectations of the impact it would have on my business were grim. A side effect of working in insurance is adopting a risk averse mindset.

I forecasted that I could lose 75% of my customer base that I’d spent years building and I’d be able to scrape by with the aim of getting out of this with a business and then going again. Starting over. And I felt invested enough in what I’m trying to achieve for that to not be the worst outcome.

In the beginning those expectations seemed plausible. A lot of small businesses were encouraged to cut costs and prepare for a worst case scenario. That meant a lot of panicked freelancers were reviewing their monthly outgoings and I was flooded with cancellation requests.

I fulfilled them all. I’ve never made customers jump through hoops to cancel their insurance and I wasn’t about to start.

Cancellations at the best of times feel like a dagger to the heart. I think you’d be hard pressed to find a founder whose mood isn’t affected by them. I think cancellations carry an extra sting when bootstrapping because you don’t have external funds to fall back on—your cashflow is everything.

When those cancellations all come at once and it’s how you’re starting your day, every day… I have no words. It’s brutal. You’re beginning every morning having to climb out of a mental and financial hole.

On top of this there were some freelancers who didn’t cancel their policy, just their direct debit. This meant they still had an active policy that needed to be paid for and, with most of these freelancers becoming difficult to reach, that cost fell to me.

As the year went on and we all adapted to (is she going to say it? Yep) the new normal, the number of cancellations reduced. Churn remained high throughout the year (my churn was up 12%) but the frequency steadied.

It did feel like I was signing up new customers at the same rate that I was losing existing ones meaning the business wasn’t growing—just stagnating. Considering I had originally anticipated losing most of my customers and starting over, the idea of maintaining the business wasn’t terrible. Compared to how some other businesses would be impacted I was one of the lucky ones.

It turns out, though, that the ‘feelings’ you experience during a pandemic are misleading. Once I’d got the courage to look at the numbers, the reality was that the business did grow. Just not by much and nowhere near the growth I had the year before.

One thing I’d say about removing friction with cancellations—especially in unique circumstances like a pandemic—is that it’s likelier customers will return if their circumstances change. I learned this quickly and it happened a lot throughout the year.

Many of the people who understandably cancelled in a panic came back when work picked up, or when they realised their business wasn’t affected as badly as they feared.

Keeping freelancers in business was more important than ever

I think anybody who knows me can see how passionate I am about business insurance (seriously!). How is helping freelancers stand up to unreasonable clients not something to be excited about?

With the number of freelancers who aren’t insured or don’t understand their insurance, I’m on a mission to educate and help them. This duty remained the same throughout the pandemic. In fact, we saw a rise in payment disputes due to COVID-related budget cuts so being insured was more important than ever.

However, my enjoyment of my job on a day-to-day basis did falter. I found myself waking up on Monday with dread around what kind of week it was going to be.

The focus shifted from, “How many freelancers can we help?” to “How many cancellations are we going to get?”.

It’s easy to be motivated when customers are happy, when you’re making money, when business is growing. That is the easy part. Anybody can thrive in that situation even if you’ve not emotionally bought into the company mission. The hard part is remaining motivated when churn is up, sign-ups are down and there’s nothing to suggest that this is temporary.

I mentioned the importance of bootstrapped businesses making money due to not being subsidised by investors, but I’ve never been driven financially and it’s this bigger goal of helping to keep freelancers in business that drives me each day. It became clear during the COVID outbreak that this goal remains the same whether I have 200 customers or 20,000 customers.

The reason I mention this is because I don’t think I would have had the mental capacity to last the year if I wasn’t bought into what With Jack is trying to achieve. If I’d started this business purely because I’d identified a good industry and demographic to profit from (spoiler: it isn’t), I think that would have made a difficult year even more challenging.

When the chips are down and the numbers are heading in the opposite direction of where you need them to go, it will make a difference believing that the product you are offering impacts a person’s life in a better way.

That belief kept me going.

My new full-time role

Despite the yo-yo in numbers with sign-ups and churn, it was business as usual and the year was busy with claims coming through.

Clients were still pointing their finger at freelancers and blaming them for all sorts (usually for the client’s shortcoming). Freelancers were still breaking equipment.

There was a huge increase in customer support and for a big chunk of last year my full-time role was in customer service. An abundance of freelancers were getting in touch to ask how their insurance would help them through Coronavirus.

Generally these questions fell into two categories.

  1. My project has been cancelled. Will my insurance help me bridge the gap financially?
  2. If I get ill will my insurance help me pay my bills?

The type of insurance I arrange is professional indemnity. It’s a complex product, but the simplest explanation is that it provides you with legal help if a client threatens to sue you or tries to recover compensation. Mostly this is due to work being delivered late or it not being to the standard the client expects.

It doesn’t act like a savings pot for cancelled work. It doesn’t protect your income if you’re ill (there is insurance for that, but it isn’t what we do… yet). Ultimately, professional indemnity is a buffer for mistakes you make in your work or problem clients.

It became clear that a lot of people didn’t know what the insurance they’d bought actually does. I’ve always known this is a problem and it’s something I’ve tried tackling with my Unsure? Insure! series and ‘Why do I need insurance?’ guide, but the surge in customer support shone the spotlight on this issue even more.

This isn’t the freelancer’s fault. It’s my job to explain the problem insurance helps you solve and it’s something I clearly need to improve. This is a more interesting and, in my opinion, important piece of the puzzle to crack than, say, improving the customer journey. Onboarding is still important, but what’s the point in getting more customers if they don’t understand what they’ve bought? This will only lead to unhappy customers and churn.

As much as it hurt to say “no, this insurance product isn’t going to help you in those scenarios”, I used this as an opportunity to educate them about what their insurance does and when we can help them.

For an audience that’s usually disengaged (due to the subject matter, nothing to do with the audience itself), it was the perfect chance to open that dialogue. I also highlighted features that could assist them through the pandemic like the confidential counselling helpline, debt recovery service or legal advice helpline.

Difficult situations can emphasise areas that need improved. It showed me that my main focus should be our positioning, which is something I’ve been tweaking over the years.

I spent a lot of the year learning more about the JTBD framework because of this. I’m hoping the framework helps me to unlock the missing piece of the puzzle.

If the JTBD framework interests you, I recommend reading The Jobs To Be Done Playbook by Jim Kalbach. It’s the best business book I read last year.

A problem shared is a problem halved

This is the first time I’ve shared my experience navigating the business through a pandemic as a solo founder. The truth is I felt like I couldn’t be honest with how I was feeling.

Even when everything is going smoothly, working in financial services means customers need reassurance that your business will be here in a year. They need a sense of stability using a financial services company that they don’t need from other businesses.

For example, if the coffee shop you order your flat white from when walking the dog closes, you’ll replace it with another cafe that’s on the same route. When people buy into a financial services company, a big factor in their choice is trust.

I felt I had to project a facade of perfection because of the industry I work in.

I watched my friends who are independent sellers or run bricks and mortar stores open up about the impact the outbreak was having on their livelihood. Their authenticity encouraged people to support them by buying gift cards or sharing their work. I never felt like I could show the same vulnerability.

It’s only now—a year into this—that it feels safe to talk about my experience because, whilst we’re not out of the woods yet, I know my business is OK. We survived. Whether rightly or wrongly, I felt I couldn’t plant any seed of doubt about the wellbeing of the business when in the thick of it.

Being bootstrapped factored into this hesitancy, too. Every one of my competitors is VC-backed. Whilst I’ve talked in the past about how I’m not conviced VC is the best model for insurance, I did wonder if—under these circumstances—customers felt more secure placing their business with funded companies.

I always wanted to reflect openly about this experience and I’ve been making notes on my thoughts and feelings throughout the year. It’s just easier to share them now that it’s clear things will turn out OK.

Of course, rewinding to March I didn’t know that would be the case. I just knew that I was losing a lot of customers whilst watching enquiries dry up and had no indication of how long this unsustainable pattern would last.

Collectively we were facing a problem that impacted us all so it makes little sense that I felt isolated. I realise this stemmed from the fact that, as a solo founder, I was carrying the burden alone. There was nobody I could share the load with.

The founder journey is very long and difficult. It definitely helps to have someone to share the responsibility with. By the end of the year, weathering this storm alone had left me dangerously close to burn out.

Have I mentioned I love bootstrapping?

I’ve mentioned a few things about bootstrapping that might not seem positive; more pressure on cashflow, customers feeling more secure under these circumstances with funded companies. But—despite some initial anxiety which was compounded by not being eligible for any government support—this year actually emphasised my love of bootstrapping!

I’ve always felt pride in being bootstrapped. I’ve talked in the past about how I feel aligned with the ethos of bootstrapping and this was one situation where it felt beneficial to be in control of my business. To be profitable, to not be dependent on external money, to not be in debt.

To be a self-sufficient business which isn’t always the model of funded companies.

The thing about bootstrapping is that you have to be smart with your money. You can’t be extravagent and spend money on things that you don’t need. Bootstrapping forces you to run a tight ship from day one.

I felt I was in as strong a position as I could possibly be to deal with things because my overheads were low and I was profitable. Admittedly I’m not familiar with how the year looked for funded companies (I’ve seen a few fire sales), but I’d imagine if you were dependent on raising funds to stretch your runway the pandemic might have made that more challenging.

How has business changed?

Aside from the obvious stuff like working from home, running an insurance business presented other challenges.

The protocol for dealing with contents claims had to be changed. Prior to COVID we’d need accidental damage claims to be accompanied with a damage report. With everywhere being closed and shipping services taking longer, we had to offer people alternative solutions to resolve their claims quicker.

There was a surge in payment disputes. COVID-related budget cuts lead to clients refusing to pay freelancers for the work they’d done or even requesting refunds. We doubled down on talking about how to handle these situations and reminded people of the help their insurance can offer.

I mentioned earlier about customers cancelling their direct debits but not their policies. There was a massive increase in credit control issues (probably my least favourite part of running a business!) due to COVID. I was left to fund a lot of premiums from customers who went AWOL. It’s hurtful when this happens given how straightforward we make cancelling and how empathetic we try to be given the circumstances. It’s the actions of one small business negatively impacting another small business when we should all be in this together.

Small wins that kept me sane

  • Weightlifting. This is number one on the list of daily activities that keep me going. It’s one hour of the day I’m not at my computer or thinking about work. I’ve always loved training, but 2020 highlighted just how important it is to my mental health.
  • Football. It helps my team is having a good season! It’s been almost a year since I attended a game and I miss it so very much. Having one or two matches a week to watch gives me something to look forward to.
  • Cycling. About 5 years ago I won a bike in a competiton and it spent years gathering dust. It’s pink. I’m not really a pink kind of girl. One upside of the essential travel rule was quiet roads and that allowed me to build my confidence cycling.
  • Film photography. Another hobby I’ve been wanting to do for years. 2020 was the year I learned to shoot film. Badly. But you’ve got to start somewhere.