The Untold Dangers of Startup Life
As a young kid I was groomed by my father to find a job at a giant corporation, clock in, collect a paycheck, then retire 40 years later. “It was less risky,” he said. “Your family will need stability,” he also added. Of course I was decades away from a family when he gave me this advice.
Now I’m 11 years into my career in FinTech and finally understand what he was talking about.
I started my career at the largest FinTech company in the world, they processed $40T in 2022, which is half of the world’s total. I worked my way up from a lowly customer support analyst to a revered account executive working with some of the largest financial institutions in the world. I did well. I routinely exceeded quota, went to President’s Club, and enjoyed a quality of life completely free of fear about my job security. They say you never realize how good you have it until you lose it…
I became fed up with the “sales prevention” nature of our business — all the red tape I had to wade through to get a deal done. No room to negotiate on terms or prices. On top of that, my commission rate was cut in half after an acquisition so I had to sell twice as much to get the same pay as before. I was young, entitled, and fuming. “How dare they treat ME like this” I said to myself. I’ll show them…
So I left the company for the start up life. I was completely seduced by the stories of Silicon Valley successes. I wanted to be a part of the next Uber or AirBNB or Salesforce. I found an interesting start up that was playing in the AI space way before all of the hype we’re hearing now and just assumed my equity would turn into millions in a few years and I’d be able to retire in my 30s. That, of course, did not happen. Despite the tech being pretty cool, there was really no product market fit. We weren’t even really sure where our product should be used. It felt like every quarter we pivoted to target a new persona for a different use case. Frustration set in and deals did not come. What did come, however, was another start up knocking at my door…
Thinking to myself, “I know better this time”, I asked about traction, revenue growth, leadership, funding…all the stuff you’d want to know before accepting a job. I’ve learned the hard way that when pursuing talent, my experience has been that those startups tend to mislead future employees on the health of their business. This was the case for me. In 5 years of existence the company was at about $800k ARR when I joined. My quota was $400k my first year — essentially expected to add 50% to the top line in a fifth of the time it took to get to current revenue levels. Needless to say, this did not happen. I watched as people came and go, with each passing day feeling more insecure about my own job security. Until eventually the axe came down on me. I was laid off. And that equity they gave me, they never bought it back from me. I’m not even sure if I still have it as I write this — it’s worthless anyway. The company hasn’t budged since I was let go.
Fortunately, I wasn’t out of a job for long as a former colleague of mine scooped me up to join his sales team at another exciting AI firm. This would be different because the CEO/Founder promised me that they grew 3x revenue consecutively over the past three years. They had an amazing comp plan so I jumped on (I was desperate too, needed a job).
My quota was $700k, which they picked by simply working backwards from my expected commission. It was atrociously unjustified. I later found out that in all of 2022 the company closed under $150k in new business across 7 reps.
I joined in large part because of my relationship with the CRO. Two months later that CRO was dismissed and replaced with two VPs. Another two months after that, one of those VPs was gone along with 3 of my colleagues. Our team was down to three. It felt like each week someone else was being let go. Our COO, who happens to be the wife of the founder, was on a never ending mission to establish her dominance and prove she’s always right. If anyone had any constructive criticism they’d be fired within the month. She was the type of person who would skewer you if you had any suggestions to the point where no one said a thing. With this toxic environment, there was no improvement. How could you improve if you couldn’t constructively criticize.
Today I’m writing this two days into my furlough. The sales team is now 1. This just 10 months after I joined to sell a product where the average sales cycle was 9 months. It gets better, neither the CEO nor the COO had the balls to furlough me or my colleagues in person. They made the cowardly move of outsourcing that responsibility to this poor VP who joined in his later years to “have some fun and make a little extra cash.”
At this point, you might be asking what a furlough is. Essentially, it’s a cruel employment trick that allows the company to NOT pay a severance. Where a lay-off would.
After three swings and misses with startups, I’m desperate to get back to that bureaucratic environment that comes with large and stable organizations. It took me 5 years and 3 startups to realize all of this. It’s hard for me not to be extremely angry, but a part of me knows that despite the lack of success, I’ve gained a wealth of experience.
My point in writing this is two-fold: 1. to get this shit off my chest. and 2. to warn those who might be looking to join a startup. I’m not saying that you shouldn’t do it, but I am suggesting that you make sure you have your questions ready and that you get concrete answers for them before making a decision.
