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What I learned from my first hire-n-fire (and what I still haven’t learned)

There’s a bit of me that feels proud that I managed to win a startup weekend as a team of one, and that, against the odds, I was also accepted onto an accelerator and completed the programme as a team of one. That almost never happens. But it has been out of necessity rather than choice. I just haven’t managed to find a co-founder or other teammate to join me. I realise that this is one of the top three common problems with startups, along with funding and focus (HT to the TeamUpp team at Startup Weekend Sheffield).

As James Clear recently wrote in The Mission, there is much more to it than finding someone with the techie skills that I lack. Less easy to define things like passion for the idea, a similar work ethic, shared values, can make all the difference between a successful partnership and a short-lived disaster.

I experienced the latter, where it all went horribly wrong, not long after I completed the accelerator.

My first hire-n-fire

I had been having a series of startup coffees with a guy I met doing my first startup weekend. It seemed more like a friendly co-support, as both of us had senior level experience in our previous professions. He had been pursuing a startup of his own, but the funding he was expecting to take it to the next level had hit a roadblock. I valued his views from being a few years ahead of me in his entrepreneurial journey. We eventually came round to discussing the possibility of joining forces, and him coming to help me with my startup while he waited to see if his funding issue would be sorted.

We discussed terms, and what our respective roles would be. It seemed the perfect solution to getting the extra person-power I needed to meet my company’s growing needs and his need to be involved in something during his enforced down time, whilst also hopefully building up some equity in something that would have value.

I knew exactly what had been holding me back, and I could identify the tasks that had priority and particularly those that I struggled the most with myself. I oriented him to the background and vision of the company. We discussed all these things, and I felt confident that we were both clear on what our plan of action was, and why.

We got legal advice on an appropriate agreement to protect us both in the arrangement, and to be clear about what the terms and conditions were.

But early on there were red flags, even before the legalities got done and signed.

Suddenly he had lots of ideas for taking the company in another direction. He wanted to add lots of features and complexity to the product before we had adequate traction in the current project or any customer feedback or research to say those things were wanted or needed, or indeed that anyone would actually pay for them if they were built. He had also been working with a tech agency on his project, and wanted to get them working on these things. He felt bad not being able to progress his work with them, and wanted to get them some alternative work.

I kept reiterating my commitment to LEAN principles, and how satisfied customers were with the product in its current state. I felt strongly that we needed to get more traction and revenue through the books before diversifying the features.

I did want to improve some of the administrative capabilities, to make it more efficient to onboard new customers and give them better customisability- those things I knew were most important to them, and to me as well. So I agreed to have the tech agency do those things only. (More on how that turned out later!)

In the meantime, I was struggling to get my new partner to deliver on anything. I felt like I was having to pull him physically up a steep bank in order to get anything out of him. I was clear and specific about what I wanted, and he was hemming and hawing and just not getting the work done. Everything was a chore. It seemed the clearer I was with my expectations, the more he waffled, and didn’t complete anything. It was as though he didn’t want my solution or idea to be the right one, but he couldn’t come up with anything better, so he kept putting off implementation until he had some epiphany for a solution that would be better than mine.

My reaction was to get more assertive and fall back into my old public sector director persona, which I am sure was exactly the wrong thing to do. It got his back up, and he dug in harder. I wasn’t familiar with working so closely to someone with the attitude “the more you tell me what to do, or what not to do, the more I will push back”.

Yet leaving him to sort things out on his own got even less progress. It felt like such childish behaviour, I couldn’t navigate it. I didn’t have a strategy for working it through.

It was my first real lesson in the manifestation of how someone can behave when it was not THEIR company, THEIR vision, THEIR passion they were working on. I thought bringing him on board with equity and vesting would overcome that issue. It was a rookie mistake of a new entrepreneur.

I really had thought this guy was as near-perfect a solution I could hope to find in the circumstances. I handled the realisation badly that I did not want to work with him and I especially didn’t want him to be vested in the company. I made some lame excuse at first as to why I didn’t want to pursue the arrangement.

He tried to say he was entitled to a percentage of the company for the six weeks we had worked together. I knew then had to put on my big girl britches and tell the truth about why I wanted to part ways. I told him I was frustrated by his lack of commitment and his laissez-faire attitude to getting things done. I was honest about my view of the work he had done as half-ass and shoddy. I challenged him to list his contributions.

After looking at the list of accomplishments together (there wasn’t much, but also included things I had done myself- cheeky!), I agreed to pay him a set amount for his work and to part ways.

What I learned (and still need to learn)

  • It’s challenging to attract someone else to your existing idea/product that they have not been a part of developing (how do you go about it?)

Though I know it is a common problem to try and find someone who is as excited and passionate about an idea or product as an original founder, it feels particularly acute for a solo female non-techie founder over 40, with a simple, mission-driven, accessible technology. I am not on the cutting edge with a shiny new tech that will make us all a billion pounds one day. I believe it is a useful, necessary technology that can make decent money while doing good. That just doesn’t seem to be enough to attract the people in my ecosystem who might have the skills my company needs.

  • As an outlier, it’s hard to compete in a pool full of peers who enjoy each others’ similarities such as age, skill set, culture (am I thinking about this wrong? Are there others out there like me who seek diversity?)

I don’t have the advantage of attracting my peers, of which there don’t seem to be many of a similar demographic in my geographic area in a position to take a punt on a new company, and that also have the skills to do so. We see that many startups are groups of friends or at least peers that come together with the promise of building the next big thing. The fun of clubbing together with people who share similar lifestyles and skills to make something great has a definite appeal. I would like that, too. It’s just that if I did that we wouldn’t be able to do what needed to be done to build the company. We just don’t have that skill set.

But I am also excited by the prospect of working with people who have very different circumstances than me. I have met some incredible entrepreneurs from diverse backgrounds in my local community and I would feel privileged to work with many of them. Women who are half my age provide me some of the most valuable insight and advice in my journey. People I know who are from different countries and ideologies are exciting to be around for their ambition, dedication to entrepreneurialism, and intense intellectual abilities and varied perspectives that they are so willing to share.

  • Not many people have the luxury of being able to gamble on the future of a company (can you still bootstrap and overcome recruitment issues? Do you have to give up the idea of bootstrapping or keeping a large share of the company?)

I don’t yet have the revenue to attract teammates by offering attractive above-market rates. Or even market rates for that matter. Anyone willing to come aboard would also have to be willing to have some faith that together we will be building something that will pay off in the future. My plans and projections show that is the case, but it is still a punt.

  • It is better to bootstrap and struggle alone than work with someone who doesn’t respect you or what you are trying to build (how do you maintain your key principles when you are desperate for help? How do you find the right places to compromise?)

But I was also convinced that it is better to have no one than have someone who would add time and energy drain to my already monumental startup workload. And perhaps even in that drain become detrimental to the company’s performance. It’s much better to be honest and get rid. Quickly. As soon as you know it’s not going to work.

That is one thing I have learned in this journey which you will have seen if you have read the previous instalments of my story- is that I don’t need to settle for less than what is good for me, and I will always stand up for myself. I believe that doing that is not only best for me but is also what is best for the company. But clearly I don’t have all the answers. I am still on a steep learning curve. I would be grateful for any comments or lessons learned that you would be willing to share!

This is the latest story in my series on how I became the founder of a tech startup as a non-techie, over-40 female with no entrepreneurial experience. You can see more here: If you think this might be helpful for others on their entrepreneurial journey, please recommend and share by clicking the green heart.

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