About four months ago I quit my job at Doublepoint and decided to start my own thing.
I'd been working on a little project with Pedrique (who would become my co-founder) for a bit over half-a-year and decided I had enough signal to determine he was someone I wanted to start a business with.
I was excited about the idea we were working on at the time, but being truly honest about my motivations, I mostly wanted to run my own thing. In a dream world I'd have had the "idea of my life" while working at PostHog or Doublepoint and have gone on to build that with maximum conviction but this wasn't the case, so I got tired of waiting for a spark and decided to go out and make it happen, with the idea we were working on being our best bet at the time.
Since I'd just quit my job, I had my finances well in order. Thus, my ideal scenario would have been to work on the idea we had the MVP for, try to get it off the ground, and if that didn't work, try something else, then something else, until something did indeed get off the ground, and only at that point we would consider whether or not to raise VC funding, depending on whether it made sense or not.
My ideal scenario wasn't going to work for Pedrique, though. He had told me for a while that the money he had saved up for trying to build his own thing was running out and that soon he'd need to start freelancing or something to make some income in order to sustain the search for a little longer. Prior to us working together, he had a bit of success with his MicroSaaS products but only just enough to increase his personal runway, which was now reasonably short.
We had spoken about this before, but with me now being 110% in, we had to do something about it. I had just come in full-time so we weren't about to go back to a dynamic where one person was full-time and the other part-time because they needed to make ends meet. The decision then became clear: we're gonna raise.
At that point, it was an easy decision to make. Again, we have two co-founders who have a lot of confidence in each other, and we don't want to let the opportunity pass us by. So while this wasn't my ideal choice, we were a business now and this was the best decision for the company. "Just don't die" goes the advice I think, and Skald had just then been born.
And so raise we did. We brought in four phenomenal angels, including, and this is relevant, my last few bosses (PostHog co-founders James and Tim and Doublepoint co-founder Ohto), and then decided to look for an early-stage fund. We eventually landed with Broom Ventures and passed up on a few other opportunities to limit dilution.
Great, right? I didn't need a salary yet, but for equality purposes, I now had one. Our investors are amazing. James and Ohto have been particularly helpful as angels (thank you!), and our investors are all founders of successful companies, including Jeff and Dan, the Broom GPs. We're super early, but Broom has been massively helpful and all-around just a great hands-off VC to deal with.
Most importantly, none of them put any pressure on us. All understand the nature of pre-seed investing well, and that can't be said about all the potential investors we took meetings with.
So some time passes and we decide to pivot. We're really excited about the new idea. We launch and get a bit of early traction. The open source project is doing well, but we're struggling to monetize. We fail to close a few customers and the traction wanes a bit.
Then I find myself fucked in the head.
And here's where we get to the point that I'm not sure I should be talking publicly about. Does this hurt my image a bit? Maybe. Do I look like I'm not cut for this? Potentially. But I've always appreciated when people share about the process rather than just talking about things in hindsight, and reflecting while things are happening + being super transparent publicly is how I am. You're witnessing my growth, live, as I type these words.
Anyway, so what happened is I found myself spending days with my head spinning, searching for ideas. I'm angry, I'm annoyed, and I'm not being super productive.
As I dug deeper into these feelings, I realized I was feeling pressured. We weren't making that much money, we weren't growing super fast. Then you look around and see "startup X gets to $1M ARR a month after launch" and shit like that and I'm feeling terrible about how we're barely growing. I'm thinking people that I really respect and admire have placed a bet on me and I'm letting them down.
Except they're not saying this, I am.
There's an interesting reflection that came up in a discussion between me and my girlfriend a few months prior that I realized applied to me, but in reverse. It's much more comfortable to be the person that "could be X" than to be the person that tries to actually do it. We were speaking about this regarding people who have a clear innate talent for something like music or sports but don't practice at all. Everyone says things like "you'd be the best at this if you just practiced more" but then they never do.
The thing is: it's a lot easier to live your life thinking you could have done X if you wanted to, than to "disappoint" these people that believed in you by trying and failing. You can always lean on this idea in your head of what you could have been, and how everyone believed in you so it must be true, but you just chose not to follow that path.
In my case, I found myself on the other side of that coin. Throughout my career, I've always had really high ownership roles, and have been actively involved in a couple 0 to 1 journeys. This led me throughout my career to get many comments about how great of a founder I'd be or how I have the "founder profile". I led teams, I wore a bunch of different hats, I worked hard as fuck, and I always thought about the big picture.
Those traits led my former bosses to then invest in me, and now suddenly I have to, in my head, live up to all of this. I can no longer take solace in some excuse like "I could have been a founder but working full-time was the best financial decision (it almost always is) so I never started my own thing". I set foot down a path from which there's no return. I've begun my attempt. I can of course stop and try again later. But from now on, I'm either gonna be a successful founder, or I'm not. And if I'm not, I'll have to deal with having broken with the expectations that people had of me.
There's a lot to unpack here, including what "success" means, and how most of what I say are other people's expectations are actually my own projected onto them (I've learned this about my relationship with my father too), but this post is already a bit too long so I'll save those for another time.
But the whole point here is not just that having raised this money from friends my head got a bit messy, but that I started to actually operate in a way that is counterproductive for my startup, while thinking I was actually doing what was best.
Ideas we considered when pivoting were looked more through a lens of "how big does this feel" rather than "what problem does this solve and for who". The slow growth was eating me, and while slow growth is terrible and can be a sign that you're on the wrong path it needs to be looked at from an objectively strategic lens. Didn't we say we were going to build an open source community and only later focus on monetization? Is that a viable strategy? Do we actually have a sound plan? Those were the things I should have been thinking about, rather than looping on "we need something that grows faster".
The people who invested in us, invested in us, not whatever idea we pitched them. And the best thing we can do is to follow our own process for building a great business based on what we believe and know, rather than focusing on making numbers look good so I can feel more relieved the next time I send over an investor update.
We have a ton to learn, particularly about sales (since we're both engineers), so we can't just be building shit for the sake of building shit because that's our comfort zone. But if our process is slower than company X on TechCrunch, that's fine. It's a marathon after all.
So after probably breaking many rules about what a founder should talk about publicly, what was my whole goal here? I mean, the main thing for me with posts like this is to get things off my chest. I've always said that the reason I publish writing that includes poems about my breakup, stories about falling in love, posts about my insecurities, and reflections about my dreams is that by there being the possibility of someone reading them (because technically it could be the case that nobody does) I can truly be who I really am in my day-to-day life. If I'm ok with there being the possibility of a friend I'll meet later today having read about how I felt during my last breakup, I can be myself with them without reservations, because I've made myself available to be seen. That's always been really freeing to me.
As a side effect, I'd hope that if this does get read by some people, particularly those starting or looking to start a business, that they can reflect about themselves, their lives, and their companies through listening to my story. I thought about writing a short bullet list about lessons I learned from raising money and dealing with its aftermath here, but honestly, that's best left to the reader to figure out. We're all different, and how one person reacts to a set of circumstances will differ from someone else. Some people don't feel pressure at all, or at least not from friends or investors. Or they only respond positively to pressure (because it certainly has benefits too). Maybe they're better off than me. Maybe they're not.
This is my story, after all. I wish you the best of luck with yours.