It's About the Journey, Not the Outcome: Some Thoughts About my 45 Years of Startups

Inspired by this post (Chapeau bas à Charles Tenot ), I’ve decided to list my own startup journey, and why I still love startups after 45 years of them, and maybe even a little advice.

• At my first startup (Automatix), I received a very small percentage of shares, as a young IC.? The company went public and I made enough money to buy a house in the Boston area at 27.? Wow!? Let’s do this again!
• My second startup (Telesis) was more mature, so I received less equity.? After some years it was finally sold.? Then the company that acquired it was sold.? That, and some additional shares on acquisitions let me cash out enough to pay for private school for my son.

After being 2 for 2, I then learned over the next 10 years or so that I got lucky - it really is not that easy to win at a startup.? But I also found that I was no longer doing startups in hopes of getting rich;? I was doing startups because I liked the excitement, the adrenaline of being on the edge, the impact I could make, and the camaraderie that comes from all being on the same adventure.? In other words, I just got hooked - I became a startup junkie.??

• Then, after a couple of failures and one exit that made back just the investment and paid the founder some, I joined Virtual Machine Works as the 5th employee with 1.5%, brought on by the CEO to coach the VPE who was right out of his graduate program.? The CEO self-described as a hired gun, who was 70% on his way to “a Unit” as he called it…personal wealth of $100M.? After 18 months, he sold the company, and we all made out some. (College fund) (learning - sell early & sell often). I stuck through the sale for a couple of years, and learned a bunch of stuff from my mentor Robert Hum.

By this point, I was joining startups because that’s what I did.? The money was a nice surprise, but I wasn’t disappointed if it didn’t happen.? And although I came nowhere near even the first step in a “Unit”, I have been thrilled with my career, and wouldn’t have wanted it any other way. I have made fast friends, and I have great stories to tell.

So, did I learn anything?? Here’s some bon mots, and you can decide:

• Do a startup because you have to.? If you do it for the hope of striking it rich, remember that only 1 in 11 succeed, and only 1 in 100 of those make significant money. It took me almost 10 years of startups to learn this, which is way too long.? A musician once said to me that he didn’t become a professional musician by choice - he had to;? the drive to make music prevented him from doing anything else.? I finally realized after those 10 years that my choice to do startups was the same, and that executing on that passion has been a lifelong reward.??
• Make it everybody’s startup.? You started the company because you believed in the idea, and had a picture of what it could become.? Let others into your dream, and value their ideas and contributions, even if they differ from your picture;? you may not know everything, and you certainly can’t do everything.? People who feel they own an emotional stake in what they are doing perform better.??
• BUT… listen to your spidey-sense.? Even when others have good intentions, you own the vision.? Let your intuition tell you when ideas are too far off from your picture;? if you later discover that your intuition was wrong, you’ve at least learned something important.? And it won't be wrong all the time.
• Sell early and sell often.? Mr. CEO Unit taught me this one.? The longer you wait to cash out, the greater the risk that you won't.? The bigger your company becomes, the more crowded the space gets, the more opportunity you have to screw things up.? If you’re in this for life, take a lot of small wins.
• Fundraising is a grind - there's no two ways about it. It's also the CEO's main job. It's a horrible gig, filled with rejection and doubt. But don't take it personally - fundraising is about the investor and even what kind of day their having. But also don't focus on your company operations as a way to avoid the nasty parts of the job.
• Up & side-ways, a CTO’s job (a startup or otherwise) is all about cost.? A CTO’s job is to clearly explain the cost of everything tech (building, running, maintaining, etc).? A CTO’s job is also to explain everything tech in non-tech terms, so that informed decisions can be made by those who are not tech.
• ?Downwards, a CTO’s job is to make sure it gets built, operated, maintained.? That simple. But how you do that makes all the difference.? You can be a martinet or a mentor, your choice of style.
• A CTO has 2 years at a startup to accomplish what is needed.? After that, the CEO may think they can do it better ??? (and I’ve verified this across multiple CTOs!)