Introduction.
In my living journal, I chatted about what my journey with running a startup called Chatsight was like. This post is really about more of what I’ve learned about startups - when you’re not necessarily in the driving seat for this trip, and what I’m figuring out about what I could have done better - now working in a successful startup. I’m taking a break from being at the wheel for now, running service founder_mode stop .
The first few days.
Something curious happens you put a high-agency person, with the desire to make decisions unilaterally into a team of engineers who operated in a flat hierarchy previously: they all complain and request that you get fired. Change is not always well received.
I had a conversation in an aside towards the end of the first week related to that material fact (something I’d only learn was on the cards many months later.) Suffice to say, it was a wakeup call to look at your role and passion from a different angle. Were you okay not having a mandate any more, as you were used to? How about decisions that alluded you as to their nature - that you would have completely gawked at if it was yours to make?
What was that wakeup call? Rowing as a team is often more important than deciding who gets to wear a crown, crowns, or otherwise. Make bad decisions together, try to inject some wisdom where you can - but ultimately don’t fall victim to something that you may have developed during your first attempt at a startup: what being burnt feels like.
The lessons of being burnt, is sometimes something to be unlearnt.
A lot of people have made comments about the problem with second time founders. That they know what feeling being burnt is, and so that the decisions they would have made a second time over that could have worked out this time - aren’t made. In fact, they’re not made simply because they remind one of the pain that occurred the last time.
Or equally, the decisions made to prevent the need to make a particular decision because of their memory of the last attempt - distract from the main obsessions with customer and product. One could interpret this, for example, as either avoiding lawyers and their fees, or focusing too heavy on engineering practices.
You see this same pattern emerge at people who’ve worked at large companies before - who fall apart when their garden of engineering tools are revoked upon their exit. And seek to build them all back before they actually start on their idea or product.
This is all to say that I’ve fallen victim to all of the above. And from that, I have this to say: integrating the wisdom you get from the failures of particular decisions must be done in concert with a reckless desire to remake those same decisions you thought were flawed. You must continue to fall off the diving board while trying to make the next jump better, instead of trying to over engineer the perfect angle to dive - or some shit to that effect.
So I guess: avoid second time founder syndrome by learning to be a first-time founder again.
I think i’m in a curious spot. I’m currently leading engineering efforts at Bland. While I watch two first-time founders crush it. I watch them from the point of view that:
- I don’t tell them what to do, or comment on what they should, or shouldn’t do - unless the conversation is open or I feel exceptionally strong about a particular facet.
- That I try to give advice, however useful it could be to a different set of material variables, and unique elements to this startup - will being extremely conscious about not transferring the fear of failure or “burn” in my advice.
- The three of us: founders in a way that no one else at the company is. There’s a sort of unspoken understanding here. A mutuality to learn together.
Decisions that burnt me in the past, that I see being played out again - turned out to not burn them. In effect, it was not the decision(s) that were inherently wrong, but it was a matter of timing and luck. Rationalizing non-deterministic decisions into some sort of internal-heuristic to calibrate your risk tolerance - that’s the danger.
Inherently the concept of a second-time founder is an over-indexing on a sample size of one. Framing it like that really reminded me that my failure was not out of necessity, but that I didn’t have the right idea, at the right stage, with the right luck - or have the right set of experiences to make my own luck at that time. While I had made luck come true in some many places, it just wasn’t the right time for me, and for Chatsight. I lacked something attainable that become clearer as time went on: a cofounder. You can be headstrong and still row together, something I believed that couldn’t happen.
People, People, People.
I’ve learned that my network wasn’t very well developed after Chatsight had failed. I was back and forth over the course of the years that it was active, between Ireland and San Francisco - and didn’t make (or rather cultivate and retain) useful connections. Equally, I didn’t exactly offer counterparties at the time, anything useful to be given back in the same vein for them to consider me into their networks.
We’re not so much talking about quid pro quo . But rather, it’s fundamentally something we proclaim as not consciously tracking - the value, or loyalty - you develop between your network and you. And yet, it’s completely how we’ve structured how we spend time. Acknowledging that while also being generous with your time is something I’m focused on.
From dates, to friends, to founders, to investors - put the effort in to retain, and show value for those around you. You never really know (as SF-coded as this is) who might want to help you in return. A person you were seeing casually, and became friends after - helped you get referred for a job. An investor who believed in you - who wants to pay it forward by introducing you to Tier-1 VCs when you had no product or customers. A friend who hits you up months after you dropped the ball, wants to catch up and create some serendipity.
All of this was something I didn’t cultivate hard enough for my last startup (although there was some solid moments I’m proud of.) Now during this one step back, I will make the time for people and to become invested in their lives. And I’ll make time for my life too in this period.
Being mature enough to allow yourself to take that one step back.
This was something I was concerned about. Previously, I had worked at Replit and felt that my desire to step back from being an authority was out of immigration fears - and a sense of when-in-rome. However, at Bland, it was extremely tempting to want to be that founder again - ignorant of the fact that it wasn’t your startup - and that you were actually an employee this time around.
I was fortunate to learn that I was mature enough to take a breath, and to take that one step back from your ultimate goal of running a startup once again. What had helped was the empathy the existing founders at Bland showed: we aren’t going to manage you, or direct you - but you should have an appreciation of what needs to get done and exist as an IC so that we can blend.
And so, I blended. I rowed with the ship. I developed some humility for my position, and that I was grateful to have survived the aftermath of layoffs previously at Replit - and given more than just safe harbor: a place to really learn and grow these missing founder-experiences in a different medium.
In doing so, I got the chance to grow and lead a team of people - engineers, and to be responsible for the company in ways that allowed these founder-traits to be exercised and not left atrophy. That was one experience I didn’t have before, managing people. Combining that same founder energy - with the real gritty problems of engineering, while also moving fast - and rowing with the boat. I know this strengthens my ability to lead and to be a founder again soon.
Had I attempted to go start another startup before these moments: it’s a toss-up if I had learned anything new. But now? I feel I will be ready again to roll the dice, and learning to forget what being burned feels like.
[Oct 27th 2024]