The Founder's Dilemma

When Unspoken Stories Sabotage Success

“All men should strive to learn before they die, what they are running from, and to, and why.” – James Thurber

In September 2022, my startup went kaput! joining the soberingly long list of startups that don’t make it, and I walked away from more investment, laid off my team, and closed the book on the biggest project of my life. Today, with a whole year’s worth of reflection time behind me, and some big insights gained, I’m sharing what I think I did wrong.

Starting my startup was easily the most exciting and liberating thing I’ve ever done, complete with all the freedom, promise, power, and prestige that a founder enjoys. But eventually it began to close in on me, bringing me face-to-face with a deep-seated fear, and I unconsciously sabotaged myself to avoid having to deal with it.

I spent ten years working as an electrician battling pay problems, dodgy contractual arrangements, and dangerous working conditions – and five years subsequently trying to fix it all with my startup. The product, Worker Feedback Club (WFC), was “Slack for construction.” The mission was to get the right information to the right people at the right time to improve productivity, safety, and mental health on-site. I completed over 1,000 hours of user interviews, raised £500,000 from VCs, and landed pilots with billion-pound clients.

But there were three key moves I made wrong in the business, and at the heart of them all was avoidance – obvious forms of avoidance like dodging hard conversations and being passive with investors, as well as less obvious forms of avoidance that were more insidious. I’ll share it all here. Hopefully it can be helpful to anyone who’s founded – or is considering founding – a tech startup.

Artist as Genius 

A few days after my 25th birthday, I moved from Sheffield to work as an electrician in London’s Olympic Village. I rented a room in nearby New Cross behind Goldsmiths University, one of the world’s top art schools, where I regularly used the college gym and hung out around all the art students. I’d watch them grazing on the grass, books and portfolios under their arms, having what looked like an absolute blast, and I’d go home and Google the shit out of contemporary artists and their work. Art had been my favourite subject at school. All this proximity to it gave me the nudge to apply for art school myself, and I finally fulfilled a long-held dream of pursuing work that was more creative and purposeful.

Over the next six years, I went on to complete a Foundation in Art & Design at Blake College London, a BA in Fine Art at Central Saint Martins London, and I was completing an MA in Contemporary Art Practice at the Royal College of Art London when I spotted a startup pitching competition seeking “innovations in the future of work.” It promised the winner £10k of investment and biz dev support from the RCA’s leading centre for entrepreneurship, InnovationRCA, which helps student startups become profitable businesses.

This competition was made for me. The first decade of my working life had been defined by hating my job, and it felt like the perfect moment to take all the things art school had given me – the networks, the confidence, the ideas – and apply them to something that could make a real impact for thousands of construction workers. My pitch for WFC won the competition, and I swapped the chalky art studio for the sleek lines of the incubator.

A slide from my original pitch deck that landed me a place at the coveted InnovationRCA.

I knew I could succeed as a sole-founder because I'd been succeeding as a solo artist, and artists and entrepreneurs are basically the same people. They question everything, zig when others zag, make things and break things, take risks and go first.

The incubator Director told me I was the first art student ever to get a place there, and this further strengthened my belief that I was the person for the job.

To me, being a sole-founder was essential to building a business that was valuable. Artists are individualistic by necessity (how can they make unique work and stand out otherwise?) and I could see strong parallels in entrepreneurs and startups – all require unique selling points. The singular genius mindset artists need to succeed was clearly what a successful entrepreneur would need to succeed too.

My past work experiences had taught me that I was better off steering my own ship anyway. Construction’s a fragmented and inhospitable place to work. It’s every man for himself, and I'd never worked in a cross-functional team towards collective goals; I'd only ever followed orders, under the supervision of men who’d been thrust into management roles without adequate training by virtue of nepotism or simply their age.

Compared to that, being a founder blew my hair back. At last, I could be my own boss, set my own vision, and do things for reasons that were important to me alone.

"Individuals play the game, but teams beat the odds." – SEAL Team Saying

However, I soon faced the realities of business. I discovered that investors value the productivity advantages teams have over individuals, and that a qualitative business plan is nothing without a quantitative backbone. I was no good alone. I needed a COO or CFO whose favourite game was Excel, someone who could bring some pragmatism and professionalism to my creative impulses.

I went out and found a consultant to partner with, and together we raised £500k from VCs. As we got ever closer to the elusive terms sheet, I grew fond of the consultant, and, naturally, we began to discuss our respective roles once he’d come aboard as my co-founder.

Feeling confused about how to divvy-up (share) responsibilities, I sought the advice of a trusted mentor who’d already built a billion-dollar business with a model similar to WFC’s. He pointed out that my partner’s technical skills (ie, finance, mergers, and acquisitions) were not what my business needed right then, which was software engineering and product design.

I finally wrote the consultant a letter, explaining why I was reneging on my verbal promise. It was messy and painful, and had it not been for our solid contract that ensured he got paid for finishing the job, we might have parted ways with bad blood and the whole investment might have collapsed. It was fine in the end. We got the cash. And we’re still friends today. But what’s important to understand is that I would not have overlooked his (or anybody’s) unsuitability for a role if I’d had a greater appreciation of what I myself could and could not do well, if I wasn’t so blinded by my I-can-do-everything artistic-founder genius delusion.

It was a wake up call. The first major inflection point where I knew I needed help. Not just investor help or advisor help or employee help or contractor help; I needed co-founder help. I hated number-crunching. I hated marketing. I hated operational-type stuff. The business was crying out for co-founders who could take those things and run with them.

By the time I did find people – employees – who wanted to join the mission, three years had passed since setting up the company, and it was too late to share the reins. I’d already raised investment, and the business was financially and conceptually too far along for there to be space for co-founders. My chance to have that unique level of support was gone.

With half a million quid of other peoples’ money now sitting in the account, I persevered. However, going it solo had the knock-on effect of prematurely tying me into learning how to manage people. I was fortunate to have fantastic employees who I’d choose to work with again in a heartbeat. But I was an inexperienced and doubt-riddled manager – I hated managing! – and I went into a state of panic, spending too much time, money, and energy seeking management training, insisting on more meetings, running 1-2-1s, and fretting over the company culture.

What the business needed most urgently at that embryonic moment is clear to me now: it needed a flat structure of two or three fiercely autonomous, cross-functional co-founders to go all in on their area of speciality with laser-like focus and superhuman intensity.

It’s obvious I went wrong by avoiding help. And it turns out avoiding help was a way for me to avoid something deeper, something even scarier.

Swiss Army Knife

Construction is fragmented. One site can have 50+ companies on it at any time. Each company can have hundreds of workers who are managed by supervisors, who answer to site managers, who report to project directors, who report to regional directors, who answer to clients, and on it goes. It’s like a big game of Chinese whispers.

WFC’s remit was to bring these scattered stakeholders closer together using technology. Our product did three important jobs:

Communication: Construction sites are full of silos. Our comms feature enabled site-wide messaging – either publicly or privately. Site Manager Mike could send a round-robin notifying everyone that the canteen had been moved. Groundworker Jason could send his supervisor a message when his digger ran out of diesel. It was about making information transfer more seamless to improve productivity.

Reporting: A common problem in construction is that bosses can’t get honest feedback or hear about dangers because too many workers are afraid of losing their jobs if they stick their hand up. Our reporting feature allowed workers to flag poor working conditions with anonymity guaranteed, and continue the conversation with management until the problem was resolved. It was about encouraging proactive feedback and making sites safer.

Recognition: Every worker we spoke to had a motivating story about being praised for their workmanship. But praise is rare on-site and is given out piecemeal. Our recognition feature encouraged everyone to take a few seconds each week to send public praise to others, and there were regular prizes for top scorers with leaderboards for tracking achievements. It was about rewarding people for their work and making sites more supportive.

An image we used to promote the benefits of WFC’s Communication feature.

Involvement from all stakeholders on-site was therefore key to our success. After all, similar workplace communication platforms like WhatsApp, Slack, and Microsoft Teams are only useful insofar as the whole team uses them. So I made sure we didn’t leave anyone in the dark.

"Trying to please everyone is a recipe for stress, misery and frustration. Be yourself. It'll be good to know who's down with that." – Unknown

The big problem was that my lack of focus and clear problem-solving led to a product that defied definition. It began as a recruitment platform. Next it became a site-reviewing platform. Then it became a communication platform. In each of its guises, it was multifaceted and didn't excel in any one area. I began to joke to friends that, “I was building an ‘MVP’ – it’s just that it was not a minimum, but a maximum viable product!”

I pushed ahead with a Swiss Army Knife solution, convinced it wouldn’t work unless all stakeholders benefited, but this lack of clarity made it difficult for users to understand what problem the product was designed to solve. We had to rely on enforcement rather than enrollment to get people using it, which explained the apathy and lack of engagement I encountered whenever I went on-site to deploy it.

Crucially, the workers themselves even handed me this insight on a silver platter. I was on-site presenting prototypes to them when they stopped me and asked, “Yeah this seems good, but who’s paying you, mate?” They weren’t stupid. They knew full-well that they weren’t the only beneficiaries, thus the product wasn’t prioritising their needs and they didn’t feel truly seen or understood. The clue was right there, but I ignored it.

When I reflect on why I didn’t get real about who I was trying to help, I realise there are two reasons.

The first is that I was being driven more by personal dissatisfaction with my previous jobs in construction and the desire to escape it, rather than a genuine passion to solve a specific problem. I managed to convince others (and myself) that I was on a mission to address a significant issue, but in reality, it was more about my personal journey.

To be fair to myself, there are real, documented issues in the construction industry, such as high suicide rates, that prove there are important and urgent problems in need of solving. Having worked on the tools for over ten years, I did (and still do) feel a connection to this tribe of construction workers and their shared experience of isolation, and I genuinely did want to help. But creating technology solutions to complex social and organisational problems is…I don’t want to say impossible, but it’s ridiculously hard…especially when you don’t have a discreet or crystal-clear sense of who you’re helping.

Source: https://www.bbc.com/news/uk-england-39303187

The other reason I built a Swiss Army Knife? I was basically scared of committing. I didn’t want to privilege one set of needs at the expense of anybody else’s. But it ultimately meant that I deployed resources unwisely, sent out the wrong messages, and built a vitamin instead of a painkiller.

What was so scary about building a well-defined product? It turns out my steadfast insistence on trying to please everyone points, again, to a deeper, more terrifying prospect that I now know doomed me to fail as a founder. And, in the process, provided me with plenty of opportunities to divert myself with dubious tasks.

Perfect Playbook

When I was ready to hire my first employees, I took the time to write a comprehensive company playbook, laying out our values, influences, history, where we worked, how we worked, our rituals, our benefits and perks, our internal tools and systems, and other important context. It was a beautifully designed document, available online and in hard copy, and was one of the pieces of work I was most proud of.

I’d read that the best companies have amazing onboarding programs, and I wanted to do the best job I could of bringing people into the team. I wasn’t aware of other early-stage founders going to such lengths for their employees, and I sensed this was one of the ways I could leverage my artistic flair to bring an unfair advantage to the business.

“Hire slowly,” is the prevailing advice, and my playbook went hand-in-hand with a thorough recruitment process I designed – four stages that included:

• Written applications

• Two online interviews (one technical and one cultural)

• And an in-person trial day

I enlisted senior engineers and designers to sit on the interview panel with me and, with their help, I brought on my team.

I saw an opportunity to give a similar artistic flourish to the employee onboarding materials. There were welcome packs and toolboxes. Walks in the park. Meals out. User Manuals and group coaching sessions. I read whole books that helped me prepare for, conduct, and record effective meetings and 1-2-1s. It was a lot to do, but I was pleased I was putting so much effort into things that might easily get forgotten about.

“The person who feels time poor is often the person obsessing over what coffee to buy for the office, the pointless thing in the meeting, or where to find the cheapest gas. They "win" all of these points, yet they "lose" because they're focused on the wrong things.” – Shane Parrish, Former Intelligence Officer

But I shouldn’t have even been doing any of that stuff because I should have been someone’s co-founder, not their boss. The playbook and the onboarding process contributed diddly-squat to business success; I was just being a busy fool who was paying the price of my earlier bad decisions.

A screenshot of the comprehensive playbook (online version). A good effort? Or a costly diversion?

My perfect playbook was one example among many of an over-engineered solution to a problem that didn’t exist. Whilst the clock ran down and my runway ran short, I diverted myself with such things as maths revision for, I told myself, “Better understanding the data we were collecting from our user-testing.”

There were my weekly reports to the team, which, instead of being short and to the point, I always treated like War and Peace.

And there was my insistence on participating to an excruciating, pixel-perfect degree in the product design standups (I just couldn’t keep the artist at bay), even after I’d hired a Chief Product Officer to own that part.

Don’t get me wrong, good execution is table stakes for startups and I’m not saying we shouldn’t aim to do things really well. But, like an artist, I wanted to do everything really well, which is silly, especially in the unforgiving crucible of startups. As the former president of Y Combinator – which has incubated many of the world’s most successful companies including Airbnb, Stripe, and Dropbox – Sam Altman advises, “Write code, talk to users, and build the company. Most other things that founders do are a waste of time.”

Trying to do everything perfectly may seem like it stems from a place of principle and empowerment. It did allow me to feel like I was being accomplished and productive. But when you strip it back, perfectionism is nothing but a high-end, more sophisticated form of fear.

There was definitely some classic imposter syndrome stuff going on in there, which I suppose you’d expect from trying to do something you’ve never done before.

But it was more than that for me. Perfectionism was a way to cover up the fact that I was noncommittal. And I was noncommittal because I was conflicted on a fundamental level.

It was the same conflict I knew getting co-founders would force me to confront.

The same conflict building a more successful product would force me to confront.

Confrontation

There was so much I loved about entrepreneurship. I loved the social side of networking and meeting new clients. I loved being on-site and talking to users. No surprise I loved all the aesthetic parts – from copywriting and branding to graphics and experience design. I basically liked doing all of the things I was good at, and that made people like me.

“If you absolutely can't tolerate critics, then don't do anything new or interesting.” – Jeff Bezos

But I can count on just one hand the number of times I made unpopular decisions. There was the time I fired someone who wasn’t a good fit. And the time I almost had to break my promise of giving existing investors the tax relief they’d earned by investing. Just the possibility of breaking a promise was enough to make my skin crawl.

Overall, I found that building a startup was something that seemed disproportionately fraught with opportunities to make me dislikable to someone, and I really didn’t want to be disliked. I’d sooner be disrespected than disliked.

What I’ve realised is: I’ve always been conflicted about becoming successful in business, and particularly about becoming wealthy. I grew up in a working-class, Labour-voting environment in the deindustrialised north, ingesting a diet of disempowering beliefs and reverse snobbery about money: “Don't worry about money; the universe will give you what you need when you need it.” “It’s better to have great relationships than lots of money.” "Only shallow people care about wealth." "You have to be ruthless to be rich." "Some people have more money than sense." “How the other half live, eh?” “Those fat cats!” “Those filthy rich!” “Those selfish so-and-sos!” “You can never get rich without ripping someone off!”

It’s not surprising I’ve always been funny with money. I’ve grown up basically believing that money is outside of my control, that it’s not possible to have wealth and great relationships at the same time, and that behind every great fortune there is a crime.

In a time when we’re bombarded on all sides by a culture that constantly reminds us we’re not enough, that we could do more and should try harder, entrepreneurship presents as one of the highest forms of achievement. As a creative and enterprising young man who was lucky enough to study at the world’s most innovative art school, I was bound to be seduced by entrepreneurship. And even though my conscious mind knew my old money beliefs were bullshit and unhelpful, my subconscious still steered the ship, believing that success and wealth would make me unpopular with the most important people in my life – even with myself – and it all added up to a slow, subtle, but steady self-sabotage.

I was a schizophrenic entrepreneur, caught between the allure of creativity, innovation and societal respect, and a deep-rooted aversion to wealth and the fear that success might alienate me from my roots and the values I was raised with. It was an inner conflict that shaped my whole approach, leading me down paths that chimed with my urge for freedom and meaningful work, but clashed with the pragmatic demands of building a company.

Being a perfectionist was certainly a way to avoid being disliked by my investors, mentors and team for being careless or incompetent. But it meant I succeeded at the wrong things, took forever to do everything, and missed out on the real opportunities.

Building a Swiss Army Knife was a way to avoid being disliked by anyone left out by a more focused solution. But it meant I spread resources too thin, confused potential users, and failed to create a strong presence in the market.

Being the artistic-founder genius was a way to avoid being disliked by co-founders over differences of opinion, as well as avoid being disliked by the part of myself that privileged meaning-making over money-making. But it meant I lacked diverse perspectives, skills, and the strategic focus needed to build a sustainable business, leading to misguided efforts and ultimately failure to achieve any impact at all.

“Particularly outstanding Founders have an unusual drive coming from somewhere inside their personality. For some of them, that drive comes from feeling unworthy and thus needing to prove something. But the paradox of this personality is that these people also do things to self-sabotage. […] If you have this, you need to be aware of it, and you have to get past it. Have your co-founders call you out on it. This is a process. But there’s enough on the internet now to educate yourself about this state of mind. Spend some time thinking about the subtle ways that you might be hampering your own success.” – James Currier, General Partner at NfX

There are three things I want to say to wrap up.

The first is that there were a lot of things I believe I did right too, and I couldn’t have done any of it without the many people who helped me. I may not have had co-founders, but I did have incredible investors, mentors, employees, and champions within the industry who were all crucial to everything we built. I’m really grateful to everyone who helped me.

The second thing is that I thought being a founder would give me everything I desired. But that was before I tried doing it, and before I discovered the 5 Salaries Framework. I can’t find a source to credit, but the 5 Salaries Framework basically encourages us to think of jobs as having five different types of salary. A financial salary obviously (wages, bonuses, and equity), but also:

1. Psychological salary (sense of purpose and meaningfulness)

2. Social salary (prestige, relationships, and identity capital)

3. Educational salary (opportunity to acquire skills, knowledge, and expertise)

4. Freedom salary (ability to work on our own terms)

Honestly, I think looking back, being a founder was a huge step up from being an electrician in terms of its meaningfulness, prestige, learning new stuff, and being my own boss. But aside from my money worries, I realise I was also earning the wrong sort of social and psychological salaries from it. I was just trying to prove I was somebody important. It wasn’t really the work I wanted to be doing; it was work I thought everyone else would like me most for.

As for freedom, I couldn’t have been more unpleasantly surprised about the realities of being a founder. Coming up with an idea and launching it was freeing, yes, but with each new investor, employee, and client I brought onboard, I watched my freedom wane as I had to become more and more accountable.

The final thing I’d say is that startupland is probably the last place on earth you’d expect to find a founder with disempowering hangups about wealth. Some may argue that money worries are a personal issue and should not be discussed in the startup community at all.

But I couldn’t disagree more. Money beliefs should be the thing founders and investors talk about first. What steps can investors take to identify a founder's money worries? And what resources and support systems are available for founders to address them? It’s vital we do this so investors don’t back founders at the wrong time, and founders don’t embark on an all-consuming journey with unexamined baggage.

Our beliefs about money, like any other story, can be rewritten. Only by confronting and sharing these narratives can we script a startup culture where money stories empower rather than encumber.

Until next time!

– Harrison

Thanks to

Michael Dean

for reading drafts and providing incredible support with this essay.

---

These essays take me ages to write and I’m working hard to get better as a writer. I’d be really grateful if you shared this with anybody you think would benefit. And if you want to subscribe so you don’t miss upcoming posts, that would be great too!