I recently posted the below on Linkedin

I recall a talk I was at recently where an older guy who'd had a really solid exit after 10+ years of work, after 10-20 years in industry, was being asked questions.

Someone asked him "how should founders handle stress?"

He replied something to the effect of

"I don't know...it's an intrinsically stressful path.

You can do some stuff to make it a bit better, but if you can't handle stress, maybe don't be a founder.

There are many career paths that are less stressful and can also pay you very well.

Not everyone has to be a founder."

I laughed because it was obviously not the expected or PC answer. He was expected to oblige the view that anyone can do/be anything, as to be inclusive, but his answer instead had the frank honesty reserved for the young and old, those who don't understand the norms they should adhere to, or don't care to.

We often idolize being a founder and being a leader, so much so that "too many" people want to be one - by it's nature, we can't all be leaders/founders...but with new technology and the wave of solo-prenuers, who knows.

There is upside (particularly if the company succeeds), but there are significant costs and practical limitations on your life. Stress is part of the path, undoubtedly.

The main thing is, it needs to suit your interests, temperament and aspirations above all else.

Not everyone needs to be a founder…it needs to suit your interests, temperament and aspirations.

The immediate follow-up worth discussing is just what do I mean by “it needs to suit your interests, temperament and aspirations”. I’ve had particular insight into this since doing some angel investing myself…and obviously being a founder myself.

I’ve found both through my experience and consuming relevant literature that, I’ve come to agreeing with the popular belief that there’s some combo of “grit” (as told by Angela Duckworth) and simply not giving up. That means being willing to be a “cockroach”, as Paul Graham put it rather unflatteringly.

However, I think something fundamental is missing from these ideas…being “gritty”, being a “cockroach”…we get that it means finding people who won’t give up, but it’s describing a what and not a why. The greater challenge is identifying WHY someone won’t give up, and why they would be willing to struggle on even if it looked stupid and hopeless.

My preferred framework for identifying if you’re likely to succeed as a founder…

The best litmus test for whether a founder is likely to succeed:

You’re most likely to make it a success as a founder if you literally feel that there is no other viable path for you.

Largely this view comes from self-reflection, which I expand on below. Before that though, I have to acknowledge that it feels stupid to me to call myself a “successful founder” (I can’t help but mostly reflect on our failings), but for the sake of this post I’ll allow myself that title since we haven't died and while we'd like to have achieved more we have got to a decent scale.

So, why did I feel the need to be a founder, that it was my only viable path…

I had only 1 job before founding my first company, stasher.com. As an early 20-something I was belligerent, arrogant and impatient. I quickly saw that I would not be able to rise as fast as I wanted, or even to work with a manager above me unless we happened to click perfectly…not a recipe for a corporate path.

I also had some passing experience working in finance…and I learnt that I just didn’t have the interest or energy to work exceedinly long hours on stuff I considered boring and, honestly, beneath me (again, arrogant early 20-something). In my head, there was no way that I had done all that work in life to that point, gone to the most prestigious universities and nailed all the exams, to spend 80 hours a week nudging powerpoints around for a great but not truly “freeing” salary.

I also found that my style of working and thinking was often erratic. I’ve found this can be super valuable when paired with working environments, and people, which suit / balance that out - as my co-founder and current working pattern does - but it did not suit the typical desk job and corporate hierarchy.

Finally, I’d been raised by a tough, but very loving and supportive, Eastern European mother (read into the stereotypes what you will), and a self-made father who’d gone from a single-parent, immigrant household to comfortably middle-class in one generation. They taught me (explicitly and through the stories of their lives) to expect exceptionalism of myself and to demand it of the world around me.

That’s a very grandiose and self-flattering way of saying I had a big ego and thought I was “too good” for a lot of things, and felt an immense pressure to overachieve. Time has eroded most of the negative bluster to this and humbled me time and time again, with little sign of relenting.

Anyway, this combo of being a difficult person with an erratic working style and a big ego lends itself to 2 things that I could think of: working for yourself or being an academic…and I didn’t think I was smart or patient enough to become a successful academic. So. I decided I had to work for myself.

So, I genuinely mean it when I say that I felt I really had no choice but to become a founder; it was genuinely my best option available.

It turns out, this really really matters when it comes to not giving up

I’ve had several times where I’ve met brilliant people who chose to start a company. There was a small amount of the time that things would go just right and they would become a successful founder, but more often than not some blow would arrive along the path before they reached a reasonable level of success and they would duck out of this path.

When push comes to shove, if you don’t feel that there is literally no other viable path for you, unless you have a remarkably lucky ride then when shit goes wrong and you haven’t got far enough along to get hooked, then the draw of cushy jobs and conventional prestige is just too strong. You usually you have to grind for 6-12 months with no apparent success before anything good happens. If you feel you have other choices, you’ll never do this.

I’ve seen this time and time again, hugely talented people who I respect start with the intent to strike out by themselves, and in reality they’re doomed by being too good at other things. That said, sometimes I’ve seen the opposite…successful career people who low-key have felt it chipping at their soul, who’ve found their own route feeling they have no choice but to make it work.

As with all things, the art is in identifying something that no science (i.e. prescribed background) necessarily dictates…it’s a feeling I look for in my gut when I chat to people.

So why does being a founder often suck? Hence, why doesn’t everyone need to be one?

I said that blows will hit and you’ll want to quit unless you feel you have no choice but this path. Why? Why does being a founder suck so much?

Well, it’s all great when things are going good, but when things are just OK (or even bad), the reality of being a founder can’t be masked by the intoxication of growth and success.

Before considering the subjective or objective reasons, consider one thing in your perspective. Whatever you feel about your work will be magnified, and for many this sort of intensity is uncomfortable. You are literally creating an organism, but its composition is institutions and processes and people rather than organs and muscles. You will be attached to it emotionally, and deeply financially interwoven, so the highs are unspeakably high (honestly, totally intoxicating) but when the lows hit they are absolutely crushingly low. Like, scream into a pillow low. It’s like trading the stock market with 10x leverage with all of your money, but you feel everything over weeks rather than hours.

So, onto the subjective reasons… There are so many of these. What to some is a dream is to others a nightmare.

“No one bossing you around” can easily be “No direction in my day to day work”

“No prescribed hours” can often mean “all my hours are up for grabs”

“I’m directly connected to adding real value” can mean “I’m not protected if for a single second we’re not adding value”

The list goes on. The point is that whether this is desirable is highly subjective and just so dependent on your life circumstance - and particularly whether you can afford to fail, which is why entrepreneurship is the reprieve of privilege masking as “self-made”.

On top of this, there’s a bunch of objective reasons.

Firstly, consider that it’s not necessarily a good way to make money. The distribution is wider (so you have a chance of being really rich), but the median outcome is worse than a high paying corporate/finance jobs and the modal outcome is failure. You need to be wildly excited by the chance of riches vs the sort of person who prefers meticulously planning sure-things. You need to enjoy hoping for future riches and riding compounding curves vs having riches today. When you don’t feel that hope, you feel like giving up unless you can’t see any other professional path for yourself.

You’re also very locked in vs other jobs. Building a business to reasonable maturity or exit can take 10+ years nowadays and to get most of the value, you need to be around at the critical late stages. You can’t take a 1 or 2 year career break to travel, or change things up, unless you are quitting (no matter how you dress it up) or finally get to exit. Your company needs you to be the point of stability, and if you have investors this is what you are promising them. Even if you do exit, you probably have to work for someone else for 2-3 years.

Finally and really importantly, we often think we all want to be leaders. Being a leader is lonely and hard. I’ve seen for myself that it’s hard to balance building a team that inevitably feels like a group of friends, and the responsibilities of being “a boss” which often means having to do some pretty unfriendly things; I don’t care how nice you are, you will never run a meaningfully sized business for 10+ years and avoid having to let someone go or having some hard conversations. You will have to be the counteracting force to payrises and other general policy requests. You will sometimes have to say that things are not up for further discussion. You also often have nowhere to hide…these choices are yours and there’s no other way to dress it up. It’s hard. Having a co-founder helps, but it’s still hard.

There are plenty more subjective and objective reasons, these are all just examples but I think you get the point.

Often, and for many people, unless you are wired so that you feel you have no other option, there are simply better choices than being a founder. It makes you wonder if being wired that way is really a good thing at all…but at least when you know you are it helps you find your direction and your flock.

What’s your thoughts, do you still want to be a founder? Do you agree with my thoughts? Comment or message me on Linkedin.