It's pretty common for founders to write about their experiences following an exit. After even a few years of running a startup there's usually much to write about.
I started a company called Cloudability in April 2011 which we sold in May 2019. Although this was the first startup I had founded and had been properly funded, I had spent much of my career working at startups.
As said, you work your ass off for 20 years, and then suddenly you're overnight success. I must be a bit slow, because I founded my first company in 1987, so that's 32 years of working my ass off. I must be a bit of a slow learner.
One reason I enjoyed startups was the pace of learning and growth, and a startup stretches you over extended periods of time like almost no other business activity does. As anyone who knows me will tell you, I'm a very different person today even compared to 10 years ago, mostly thanks to changing effect lessons learnt tend to have on oneself.
Along the way, I was lucky enough to meet a few people who were willing to truthfully and completely share with me their worst moments. Some of the most difficult lessons come from the most difficult moments. These were my most impactful learning moments. If you're someone who shared their worst screw-up with me, well thank you. You were an inspiration in more ways than you'll ever know.
Part of the deal to sell Cloudability involved me stepping back, and I left just a few weeks after the deal closed. I really needed a break, and did the usual exiting entrepreneur activities: bought a car, traveled a lot, ate even more and slept like the dead.
Pretty soon though I began to mull the future. We had built a strong culture at Cloudability which in turn had attracted and retained really talented people who had built a strong product and growing business. What should I do next? If I was going to do it again, what would be the best way? As a founder? A board member? And investor? Maybe as a VC?
As I weighed these options, something kept bugging me. I felt like we hadn't really lived up to our full potential. It felt like we could have done so much more.
One of my biggest mentors, in fact probably the single most influential outsider on our business, told me once very early on: "I have companies in three leagues: Premier League, going to the stars; Second Division, going to be okay but not great; and the Dumpster Fire, going to zero. Your company is in the Premier League, but it's at the bottom." I didn't really get what he meant at the time, but suddenly one day I got it.
I'm not going to write about our biggest strategic errors (or even mistakes ), decisions that turned out to be wrong in hindsight, etc. This kind of thing is easily found, it has been written about many times over.
Looking back in perfect 20:20 hindsight, what hit me was that we had not been paying enough attention to the dignity of our people.
What does this even mean? Let me explain.
The word 'dignity' has a Latin root, 'dignitas' meaning the worth of a person. Ancient societies quickly realized that the most powerful or moneyed citizens weren't the only ones with value. The wise, the skilled, the talented all made invaluable contributions. Hence, the notion of the total worth of a person, allowing for all the pluses and minuses of their contributions to the people around them.
And, critically, dignitas -- well the generally perceived level of dignitas at least -- decided how these individuals were treated by the rest of the group, what kind of privileges and tolerations they were entitled to.
Wordologists will tell you that ancient, unchanging words describing ancient, unchanging things in our lives. We picked up many words in English from other languages, but some base concepts -- death, shit, blood, flea, fuck, etc. -- are the oldest. Dignity is almost unchanged from 2,500 years ago.
So speed forward to today, and notice many trends related to dignity. Firms which treat their staff well, they get the best people. Movements all over our nation are protesting because their worth is not being recognized. From BLM to Maga via Google, how we perceive others is very important and often measured totally inaccurately.
And Cloudability was no different. I was and am a huge believer in our people. I wanted every one of them to succeed. We tried our very best to get the very best out of them. And, for the most part, we succeeded.
However, due to this non-malicious, inherent and persistent bias that our people were high worth, we had difficulty in recognizing and reacting to instances where we got it wrong. Where we wanted to believe but person x or y just wasn't up to the role at this time, or needed help, etc.
Don't get me wrong: in no way am I saying that in these cases I now think this people had no value. What I mean is, when asking the question: in this role, at this time, how valuable is this individual? We often failed to act when we thought they were a better fit, or setup for success, than they were.
This leads to outcomes we did recognize at the time, for instance: conflict avoidance; difficulty conversations happening late, weakly, slowly, inconsistently; team struggles when the leader was not the best fit; a lack of data relating to poor performance because nobody wanted to the person who got their colleague fired; discovery of poor performance and/or behavior after the individual departed; surprisingly poor results in some teams or projects at times.
All of these were symptoms of our, of my, unshakeable belief that we had the best people, all the time, and if there were difficulties, they just needed some help to work it out.
If we had mastered the concept of dignity, we could have spent a lot more time attempting to get better at it. For instance, when a new hire doesn't work out, the hiring manager is partly responsible. Sure, the individual represented they could do the work, but the manager believed that. What could we have done, in hindsight, to have measured the individual more accurately? Or did we measure them accurately and just failed to onboard them? Moved their cheese, under-resourced them, or some other way set them up for failure?
Our inherent positivity made it very difficult to be great at asking and answering all these questions.
I realized that, in many ways, being too nice is almost as bad as being too nasty. And, crucially, both involve an inaccurate valuation of the worth, to the organization, of a person and their efforts.
They say the first challenge in any problem is to recognize it. Now I have, I see the benefits and opportunity of solving this problem every where. We spend massive amounts of time and energy on accurately measuring our business but, meh, when it comes to people it's impossible, so let's just do an annual review and ignore this problem, right?
Over the course of this book/series of blog posts, I will share with you some thoughts on how to nourish dignity in your own organization. I will not tell you you should be doing this, instead I will strive to demonstrate the benefits. I will not judge you for going beyond or doing only a part of this, even deploying a part of this thinking, should, in my mind, make your business stronger.
I just want to help you learn from my own mistake, one I committed over and over again, despite all the evidence I should adapt. While it's a positive experience to study one's path and grow wiser from it in hindsight, it's also a less than pleasant experience to realize that, all things being equal, a different approach would surely have yielded an even better outcome. Hopefully, I can help you avoid making a similar mistake.
