tl;dr – Two companies let me go and had to replace me with numerous workers, costing them a huge amount, one of which went out of business over it. The 3rd burnt me out and it basically doomed the company.
It’s interesting how I work very hard yet frequently get let go.
I have identified the issue and addressed it. It comes from having been a very busy CEO of a successful company. My time was my most valuable asset. I became pretty irritable whenever people forced me to spend time on anything not tied to increasing our value or to trying to show off. I’d very quickly tell them I didn’t have the time, direct them to their boss, sometimes forcefully, and get back to what was important.
So when I started being a CTO at companies after that, my approach was to do my job very well……and stay out of the CEO’s way. In many ways, to be an invisible CTO. I viewed that technology should just work and be invisible. The CEO shouldn’t have to worry about it. That’s what I had wanted and what I figured other CEO’s wanted.
I could not have been more wrong. We’ll revisit how I was wrong later. But first, some stories.
The first company to hire me after mine was like an Alibaba like bulk purchase drop shipping company. I was hired as CTO to both architect and build their backend, hire, and manage their entire engineering team as well as manage their infrastructure. I hired a very talented front end dev and a designer and we set off. I knew exactly what needed to be built so I didn’t interact with the CEO much, and he seemed very busy with other things. We were dealing with a huge amount of data and products so our SQL queries required a lot of horsepower and our COO had given us a large hosting budget so I picked Softlayer as our hosting provider given that they could provide the fastest servers which would cut down on page response times significantly. We were spending a lot on hosting but it was well below budget. After a while, the three of us got a first version out the door. The CEO was happy, but sales never really came in.
There’s always this slack time in startups between the first prototype, sales, and adjustment to the product. Especially when you don’t have a product manager. There’s not that much to do. Software kind of runs itself. So sometimes you do end up sitting around without much to do, especially when you work as fast as I do.
The company did eventually hire a product manager from eBay. Not to be insulting, but he was an idiot. He was clearly used to working with a team of yes men and hundreds of engineers. First, all of his ideas wouldn’t move the needle of sales at all when our problem wasn’t closing sales but that we weren’t getting any page views in the first place. Second, his concepts were ideas that would take months to complete a single feature for our small team. As I said, he was used to working with huge teams on a much longer timeline.
So unfortunately, I was placed into the role of the voice of reason for the company. We didn’t need new, insane features. We needed eyes on our website. Our marketing team was failing completely. Of course, the marketing team pointed the finger at product but the conversion rate for anyone who actually visited was actually pretty high so that was easy to refute.
I think the product manager lasted 3 weeks before the CEO realized he was not a fit.
The CEO did have a bad habit. He’d fire people if he so much as got a bad feeling about them. Turnover at the company was somewhere around 10% a month just from the CEO randomly firing people. It made me very uncomfortable which is also why I avoided him. The tech worked and worked well. I was also the only Python engineer at the company, the only one who knew how our code was deployed, and the only one who could even login to our infrastructure. No one else was qualified. He was a penny pincher so the idea of suggesting we hire someone else to be my backup never even crossed my mind. We were always short on cash so we simply didn’t have it. Documenting it didn’t make sense because the other engineers didn’t have the know how to do any of it.
Well, the time came for me to go to my first nephew’s bris. The CEO literally called during the ceremony. Having to red button him I knew was a very bad idea. I called him immediately after. He said we needed a change on a feature on the backend and wanted it pushed immediately. I explained no one else could do it but me. He was furious. How could this happen? More specifically, how could I allow this to happen? Why didn’t we have a backup for me? (Because you wouldn’t pay for it asshole)
He demanded I work on it immediately and document the process to deploy code. So as soon as I could, I made the change (it took 5 minutes) and wrote the documentation (another 5 minutes) and sent it to the only other developer. He immediately asked what he was supposed to do with it since he didn’t know how to make changes to the back end code as he didn’t know Python. I said, “I don’t know, the CEO Just asked me to get it to you.”
Well, I got back and the next day the CEO brought me into the meeting room.
“Do you know what our server costs are?”
“Yes”
“They’re huge!”
“They’re under budget”
“Whose budget?”
“The COO”
“He was fired because his budgets were terrible. I rant his past one of our advisors who said we should be on AWS and it should be 10% of this. I am very upset. I expect you to move everything there in 72 hours.”
“Respectfully, sir, we have so much data, with transfer rates being what they are, we simply cannot move all our data in that timeframe. I am happy to do it and it won’t be difficult, but it’ll take till the end of the week.”
“No, 72 hours.”
“Sir, that’s physically impossible.”
“Get out.”
I got out and as it was the end of the day. Around 8am the next morning, I got a call from the CEO. He told me today was my last day and there was no need to come into the office.
I was livid. But I also knew he was fucked. For several reasons.
The first call came around 2pm that day.
“Hi. Ummm, do you have the password for our hosting provider?”
“Yes”
“Ok, I need you to send that to me.”
“No.”
“What? It belongs to us.”
“No it doesn’t. You fired me and it’s on my personal laptop.”
“You’re fucking kidding me. Give it to me.”
“No.”
“I’m calling my attorney”
I knew my rights. It might have technically been their property but I hadn’t signed anything saying I would hand over their property when fired (I had re-read my employment agreement) and they hadn’t given me a my severance yet. And even still, they would have had to sue me to get it, which would take years.
My phone rang again in 10 years.
“We need that password.”
“Ok, pay me”
“What? No. It’s ours.”
I’ll make a long story short. I explained I not only had the passwords to every infrastructure and hosting service, but every service they used, plus the root passwords for all their servers and databases on a personal cloud synced (Evernote) note software. It was backed up and safe but on my personal property. If they wanted access to any of their own infrastructure, they’d need to pay me for it.
In the end, they gave me a severance of $250,000 to get their passwords back.
This is why you always give people corporate laptops and make sure you set up proper documentation and don’t fire your CTO out of nowhere and piss him off.
Now began their real problem: They didn’t have anyone who knew Python, infrastructure, devops, or how to do any of what they needed.
The frontend engineer was a good friend of mine so he kept me apprised of what happened.
First, it took them 4 months to hire a Python engineer and a Devops engineer.
Then it took them 2 months to figure out how everything worked.
So about 6 months later, they finally made the move to AWS. Something I said would take me a week. All the while paying the $4,000 a month or so in higher hosting fees we were paying at Softlayer.
The issue was, these were average developers. And I’m significantly better than average.
In the end, my friend told me it took about 6 hires and 9 months to get back to the pace that we were at before they got rid of me.
So that was the 1st company.
Then there was my friend Matt’s company.
This company was a B2B/C business selling building materials. I build their entire e-commerce site from scratch, a huge effort, as CTO and we had a pretty good relationship.
Again though, when we launched, the sales never came. This was primarily because their business model was broken and the images of their products were in consistent and bad.
So we tried a truly fantastic designer to remake the site…….except he was very slow and did not like having a timeline put on him, which the CEO did. When he missed deadlines, he had a really bad habit of…….blaming me. And he got very close to the CEO so no matter how much I protested, the CEO believed him and bought that it was actually me missing deadlines despite my never being given anything to work on by this designer.
Additionally, again, the site reached a steady state and I didn’t have much to work on. This was in a highly visible office so it was very hard to look busy, especially while waiting for weeks on end for this designer to finish up his front end work. So I looked like a very expensive paperweight.
Finally, the designer gave me the files. I literally got the new site done in the same day. It looked lovely. We all celebrated. But my relationship with the CEO had completely soured.
Again, I had told him many times we should get someone to work alongside me so “if I get hit by a bus” nothing will happen. They had a very tight budget and he always said no. In this case, I did have spare time so I made some documentation but the infrastructure was much simpler so there wasn’t much to document. But as before, there was no one else who even knew how to login to AWS (our hosting provider) or knew Python.
There was another sign that I was being let go. The CEO had contacted me about a typo in my RSU grant document. It said that their repurchase rights were accidentally at fair market value instead of par value. That would make them worth about $65,000 instead of $0.0001. He demanded I agree to change it. At first I declined, but then he found ways to make my life hell. So what I agreed to was to change it to the “maximum tax I might pay if these RSUs were ever exercised.” He immediately agreed thinking it meant $0. What it really meant was 53% of the total amount. Moron.
So I got a text from the CEO one night asking to have breakfast at the Omni hotel the next morning at 8am. He knew I hated mornings so I figured that was my first punishment. I had given many months of 80+ hour weeks to this company.
So I came in and sat down. In about 2 minutes, he just said today was my last day and there was no need to go into the office. He didn’t thank me or say much more than that at all. Then he got up and left.
Now, he was a first time CEO. I also knew he really didn’t know CA labor law well so knew this would go badly for him. So I kind of chuckled, ate breakfast, went home, and relaxed.
And waited.
The first sign something was amiss was about a week later when their website suddenly disappeared, never to be seen again. Whoops.
They also never paid my my last paycheck on my last day which is CA law. If you don’t get it, it basically means you’re still employed. They have to pay you up to the day when they actually give you your final paycheck.
So, I casually wait, knowing they have great attorneys (that I introduced them to) who will eventually notice what happened.
About two months later, I get a big envelope in the mail.
Inside it, are:
• A dismissal letter
• A long severance agreement
• A repurchase agreement for my RSUs
• A check for around $35,000 for two months of wages
• A severance check for $40,000
The severance agreement apologizes for not getting me all of this sooner. It also clarifies that I should have been classified as a W-2 employee and not 1099 and the size of the severance was to make up for that provided I did not sue the company. The final paycheck size was mandated by state law.
The RSU repurchase agreement was as I suspected. 53% of $65k. Except they would pay me it in 60 days. I signed and returned it. 59 days later I got another huge check. In total, firing me cost them around $110,000.
As for the company, the loss of their primary technical resource entirely killed their product. I’m not quite sure what happened, but their website died and never came back. I later learned they ran out of cash and went bankrupt around 5 months after I was fired since they couldn’t raise anything without a product.
I actually ran into Matt, the CEO, about a year later at a social club in downtown SF. He actually came up to me. He said hi nicely. I was still a little mad. And he actually apologized. And took his time too. He explained he didn’t realize the designer was such a liar who was also actually stealing from him. He should have trusted me. He also had no idea how important I was to their operations and deeply regret letting me go. They had tried to work on the site and accidentally deleted their production database which permanently took down their website. They tried to hire a replacement for me but couldn’t find anyone and ran out of cash.
Since he was independently wealthy and the failure of the company didn’t really affect him, he was really willing to own up to his mistake and recognize how crucial I was and that he hadn’t respected it. It was really quite nice to hear. We ended up reconciling and becoming friends again.
Lastly came the fintech company.
To put it simply, I built an entire division at there: their bank. I did not hold back at all in my requests for help. I told them straight out they needed to hire similarly senior people to help me and to keep the knowledge at the company “in case I got hit by a bus.” They refused to spend the money.
I also was working was was probably a $500k job for $165k. I asked for raises and more equity dozens of times and was denied. I was only given a hint that I might get a “small” raise in August at the annual performance review. I was literally doing the work of 5 people, with long, long hours. The stress was unbelievable.
I couldn’t maintain the lifestyle I wanted. I developed a severe drinking habit. I was miserable and my mental health was shattered. So I finally submitted my resignation in early July 2019.
Instead of offering me more to stay, they threatened me and yelled at me. My Dr saw the shape I was in and gave them a note for medical leave and then they denied me my final two weeks pay.
Well, I got the last laugh. Through my friends there, I quickly found out no one could figure out the software I had built and of course, they had given me no time budget to document it. So they were forced to scrap it. They lost tens of thousands of customers and all of their momentum going into the launch. It must have been highly embarrassing to explain that to their investors. I was told they had to hire a new team and start from scratch. From what I could see on LinkedIN, during development, they had around 15 engineers related to “Banking” plus some managers.
They didn’t relaunch a banking product until over 13 months later, at the height of Covid. It was a complete flop.
Later, after they went public, their first financials showed the status of their bank. They had around 10,000 customers. Total. We had over 500,000 on the waiting list that we were slowly rolling out to when we had initially launched.
In essence, my leaving had permanently doomed the bank, costing them potentially billions of dollars in value. We had worked out that every banking customer was worth $156 of revenue per year. So a million customers was $156mm in revenue or at 20x, our current revenue multiple, around $3.2 billion. We figured we could achieve that in about 2 years, which all of our financial modeling was based around including the fundraise we did while I was at this company, which took our valuation from $400 million to $1.1 billion on the back of the work I was doing.
All over not giving me a raise.
Fuck them. Fuck them all.