2 - Deciding Whether To Start A New Startup

Over the next three posts I’ll cover my experience addressing the following cascading questions of starting up again:

• Whether to start a new startup

• When to start that startup

• What that startup will be

Spending time deciding whether to start a new startup sometimes felt counterproductive. The decision could always be reversed. There was a risk of placing too much pressure on it; of chasing an illusory certainty. And consequently never getting going in the first place. On the other hand, as that startup progressed there would only be more commitments - customers, co-founders, team members and investors. There would be the inevitable and frequent low points when prospects look bleak - ample ammunition to question whether it was right to start in the first place. Comprehensively considering, without procrastinating, whether starting a startup was the right decision could only be of benefit to my future self. The confidence and peace of mind it provides is an invaluable asset on the entrepreneurial balance sheet.

Here’s how I went about the process.

Is It Possible To Start?

The first consideration was whether my life was compatible with starting a new startup. 

I started Chaser when I was 29. I was getting married the next year. I had a very modest pre-financial crisis tracker rate mortgage and a reasonable amount of savings. I could afford not to earn a salary for a while. I’m now 37 with three children under five. We have a family home mortgage, childcare costs and the larger outgoings that come with being a quintet not a couple.

I’m fortunate that my wife’s career means we are financially in a position for me to start a new startup. I, and Jess my wife, can attest to how easy it is to take that enabling factor for granted. Cicero said “gratitude is not only the greatest of all virtues, but the parent of all others''. Aside from the obvious benefit of ensuring that it’s viable, considering whether I could afford to start a new startup brought a valuable reminder to be grateful for what enables me to do so.

Beyond the financial considerations, there is consideration of whether starting a startup is compatible with other life priorities. I became a father when I was three years into Chaser. The thing I am most grateful for from the last year is the way it has given me the opportunity to: 1) question whether, and map how, being a great parent and entrepreneurship are compatible, and 2) I realise I previously fitted being a father around running a startup. Now I can fit running a startup around life as a father.

One of the best things I’ve done in the last year is invest time in personal mission, life priorities and values. My 29 year old self would likely have been cynical about the value of this. But now I see the impossibility of deciding a) whether entrepreneurship and starting a new startup is the right thing for me, and b) how it should function alongside other life priorities, without first having identified what those whole of life priorities are. Alongside personal learning, I worked with a coach on this. Having a thought partner for this project was invaluable and I look at it as time and money excellently spent.

Do I Want To Start?

Having concluded that it was possible to start, the question was then whether I wanted to. It is recognised that the salary, security and prestige of employment can present handcuffs to making the leap into entrepreneurship. Handcuffs can also operate the other way around. That because you’ve started a business previously, you must start another business because that is who you “are”. Pride and ego can also flex their muscles here. It would have been very easy to just automatically conclude that I did want to start up again, but it was best to test.

One thing I’m glad I did was apply for a couple of jobs (I didn’t get them). Going through that process helped me consciously confirm that I didn’t want to work for a business that wasn’t my own creation. 

I’ve done a bunch of consulting work in accounting tech over the last year, working with businesses who want to partner with accounting firms as a route to market. Alongside working with more established businesses, I’ve also mentored and consulted with some very early stage startups. That was invaluable when it came to deciding whether I wanted to start up again. It gave me a representative trailer of the full length film. It gave me source data to inform my decision that yes I did want to start up again. It also provided first hand exposure to the warts and all challenges of starting up. I couldn’t hide from them and make my decision to start based on an inaccurate rose tinted picture.

A culmination of whether I wanted to start up again was explaining what an entrepreneur is to my four year old twin sons. That you use your detective and noticing skills to find an unmet need that a big enough group of people have. You use your creativity to come up with and then test solutions to meet that need. You then find a way to sell that solution for more than it costs to deliver it. If you do that, you get to hire people you want to work with, who inspire you and you can learn from. You get to shape your own role around your strengths and what you’re most passionate about doing. All of this whilst creating something that can be much much bigger than you as an individual. It’s the best job in the world!

Can I do it?

Having concluded that it was possible and I wanted to start, the question then was whether I could.

This was about looking at what I’d learnt about starting up. And looking at what I’d learnt about myself. This will not be my first rodeo. I have a lot of things that I am proud of from my seven years with Chaser. At the same time, my leaving was what would euphemistically be described as an unplanned departure. Prior to deciding to start something new, it was incumbent on me to ask what that temporary defeat was telling me. Where was I coming up short as an entrepreneur? And was I both excited and willing to work to grow and get better? Based on the experience I have, and with as much objectivity as possible, did I believe that I could be successful?

It was essential to ask those questions. Otherwise I’d have been wilfully blind (and would have missed out on invaluable raw material for growth). At the same time, to anyone in a similar situation I would advise not to expect definitive answers. As Voltaire famously said: “Uncertainty is an uncomfortable position. But certainty is an absurd one”. There will always be raw material for doubt if you choose to feed it. Henry Ford captured it well when he said:

“Whether you think you can, or you think you can't, you're right”

And Then

This nested algorithm was the first part of deciding whether to start up again. Comprehensively considering whether: i) it was possible to start, ii) I wanted to start, and iii) believed I could do it; provided me with a foundation. Those questions are like preliminary gates to go through. They provide an invaluable underpinning; a confidence I’d considered things fully and had a sound basis to make the decision. Entrepreneurship is part art, part science. The decision of whether to start is no different. T.S. Eliot said: “We shall not cease from exploration. And the end of all our exploring. Will be to arrive where we started. And know the place for the first time”. This process, this exploring, was the science that gave me the ability to see things clearly.

The art of deciding whether to start up again was the final part of the process. It sat on top of the science. It was a judgment call based on instinct informed by asking those questions. It was about trusting the gut on top of that foundation. I find regret minimisation a really useful framework for decision making. Visualising myself in the future looking back on this decision and imagining what I’m more likely to regret. This was wonderfully brought home to me in a talk by Jerry Colonna where he cited Jesus:

“If you bring forth what is in you, what you bring forth will save you. If you do not bring forth what is in you, what you do not bring forth will destroy you”

In the end, the judgment call was extremely easy. It was made much easier by the process I went through beforehand. And I believe my future self will thank me for the knowledge that I considered this decision as comprehensively as I was capable of at the time.

The subsequent question was when to start up again, which will be the subject of my next post. Thanks for reading and stay tuned!