Investor rejections are the easy part
heartbreak with a two week notice
You get good at handling rejection as a founder. Of course it sucks when a potential customer or investor tells you no, but it happens all the time. After like ten minutes of being bummed I usually decide, "well, they're idiots" and add them to the list of people I want to prove wrong.
The one rejection that used to crush me though was whenever an employee I was close to would quit. Unlike the random potential customer or investor that says no, someone who quits your company had, at some point, bought in and believed. As a founder, I've always had a hard time separating my own identity from the company I am building. So when someone believes enough in the company to come join, it feels like they also believe in you. Then after working together, if instead of believing more they decide to bounce, it's crushing.
I like to think I've always done a good job of being professional and gracious publicly in these situations. In private though I've legit cried about this. Sometimes this was pure ego bruising and felt like being dumped. Other times it felt much more existential. Like they too saw the thing that was keeping me up at night. They got close enough to see it and knew it was true and before long everyone else would too.
Most of the time this was just me being paranoid. There wasn't anything that was actually going to imminently kill the company. I've seen it play out the other way too though. When the growth slows and one by one your best people start leaving the company. There was a stretch at Klout where every time a meeting request popped up on my calendar made me feel like I was going to throw up.
"Get out the tiny violin for the ceo who feels sad when his employees quit.” That's fair. I know people lose jobs that they really care about every day and it doesn't just hurt their feelings but can cause major economic uncertainty. I am sure I've even put people in that situation and the weight of that will never be lost on me. The people part of this job is really fucking brutal.
It's been interesting catching up with ceo friends as I am stepping back into the game. The conversation always drifts to how hard it is to hire and retain people in the current market. As someone who built their last company pre-Covid, I feel like a married dude being warned about the dating scene from single friends. It sounds rough out there.
I've been mentally and emotionally preparing myself for this part of the next journey. One big change I started while building Joymode is that I now broadcast my secret fears to the team and even the people we are recruiting. "That thing that's going to kill us is right there and we better kill it first." A lot of people will opt out and go work somewhere that paints a prettier picture. I am fine with that. I love having a team that has full context on all our challenges and finds energy in the difficult conversations.
I am also embracing the inevitability that the people who start are going to bounce at some point. It's a lot easier now. Not because I care any less. Mostly because I've grown up and realize that the world doesn't revolve around me (a hard thing for a founder to come to terms with). People leave because it's the right thing for their career or life and it's not some kind of personal slight. All I can do is try and build a company and culture where people feel they have the opportunity to continuously grow and be thankful for the time I get to build with them.