My Heart’s a Mess (A Debrief on Startup Disappointment)
There’s a great Goyte song called “Heart’s a Mess” that I love the chorus from, which goes:
Your heart's a mess
You won't admit to it
It makes no sense
But I'm desperate to connect
And you, you can't live like this\
These lyrics really resonate with me right now, as I find myself in a very difficult and painful spot in my career.
Many years ago, I launched a startup company with a good friend of mine, which ended up taking off and attracting a big investor to put almost half a billion dollars into the company. At first of course my partner and I felt like kings - scions of industry who had attracted an amazing opportunity for ourselves. There were a lot of “toast of the town” interviews and podcasts.
As time went on however, we slowly realized that there was an incredible amount of gap between what was possible in the market we worked in, and what these particular investors expected the company to accomplish.
There were some early warning signs as to this disconnect - statements around profit margin expectations (north of 60% minimum) where we would look at each other and say “Uh - that’s never going to happen in our industry”, or pressure from the new investors (who had board control) to do things like stiff long term partners on their invoices, fire hardworking people who had worked for us for years based solely on some assessment of “not our type of people”, and blanket statements about how we should “force our customers to pay more”.
The root of a great deal of the problems at the company were product/market fit - the product we were selling required a higher commitment that our customers were willing to make, and it was priced too high for them compared to what they were paying now. We spent months on end trying to explain to our investors that these were “invisible hand of the market” problems, and the only response we’d ever get was “figure it out”, and no flexibility at all.
I can’t tell you how mind-warpingly frustrating it is to have a goal in front of you that you know you cannot hit, but no ability to do anything to change that.
As the company struggled, my partner, who led the sales team, faced most the mounting pressure to deliver upon these unreasonable expectations.
Before long, after we failed to hit the insane goal before us, the investors put their own guy in charge, and us founders ended up reporting to a new boss, and unable to drive the ship. Let me tell you, it sucks to be a founder of a business and end up reporting to someone else who is trying to run your business. Lobotomy-like, seventh level of hell, pulling toenails out with pliers-type suckage.
But guess what - if you have a product that customers don’t want to buy, just putting a new pilot in the cockpit doesn’t change anything. No change in pricing, strategy, features or plan was made, and surprise - it didn’t change the market realities that our product wasn’t a fit for what customers wanted.
We of course kept trying to fix these problems, pushing back and educating, with the hope that eventually our shares might gain some value and not go to zero, but eventually, the true plan was made known, and the board fired my partner - showing him the door without any warning to either of us. He was now kicked out of the company he helped give birth to, and of course had a pretty toothsome non-compete that leaves him unable to work in the industry that he helped create.
This event was pretty traumatic to a lot of our team members, who had come to see my partner as not just a visionary in the industry, but as a leader and friend. I found myself left behind in the business, but for unclear reasons. Did the investors just want to make sure they had at least one founder of the company around? Did they think I was valuable in some way that my partner had not been? Did I have some connection to customers and relationships that they couldn’t rebuild themselves? Or did they just think I was a “nice guy” and I hadn’t pissed them off enough yet to terminate?
All of these changes and disruption have left me pretty depressed and confused. I don’t know what this company that we created is anymore, nor what my place is in it, or whether I should expected to be fired at any moment.
As I have a large amount of equity in the business still, it’s tempting for me to think that I need to stay here just on the off chance that my shares increase a lot in value and we have a successful exit. At the same time, with my unhappiness increasing every day and my frustrations around this situation rising, can I really afford to stay for my own mental health?
As we round the corner here on the end of the year, it just feels like there’s bad news after bad news. The economy, political environment and industry is struggling, and our leadership/investors are even more out of touch than they ever have been. As a founder, the toughest decision of all is, do you walk away from what you built, what you put blood sweat and tears into, when it changes into something barely recognizable to you? When something is to completely tarnished and ruined, is it worth it to stick around, hanging onto hope that there might be some way of it turning around for the better?
Do you stick around because there’s too much of your identity tied up in this business, and all your friends and family know you as “that guy who did that thing”? Do you sit quietly and draw a paycheck while others drive the ship into a coral reef and sink it?
Or do you pull the ripcord, sacrifice everything you’ve built to the dumpster, go off and create something new, and hope to make better decisions during Round 2?
I’m really not sure what I want to do.