I like being a second-time founder.
It’s like having your second kid. You don’t sweat the small stuff because you know what the small stuff actually is. You feel more confident in your instincts and rely on your gut more than your hyperactive mind and what other hyperactive minds around you tell you.
You have a general sense of the shape of things — the highs, the lows, the things to watch out for, the things to not stress about so desperately.
Being a second time founder is such a gift in so many ways.
But it can also be a danger. There is a unique flavor of paranoid confidence that is bestowed upon repeat founders — more confident in what’s possible and how to pursue it, but also constantly aware of all the ways you can fuck it up.
Beyond that, startup years are hard on a founder. The hours worked, the heart and soul consumed, the impossible decisions, the painful people calls. All buried deep down, in service of keeping the company alive.
All of this accumulates and unless it’s being processed by some high power therapy (which, let’s be honest, for most of us, it isn’t), it’s just pile on and piles up, a toxic carbon compressed under the highest of pressures into a deadly diamond that is what shines when others look at us.
But we know the truth. It’s dangerous if not handled correctly. Instead of the being the hardest substance that gives us superhuman strength, it can be the brittle kryptonite that crumbles with the wrong crack and leads to our downfall.
If you’ve been a founder and you’re considering getting back into the arena here’s what I would say are the 3 biggest superpowers you can count on and the 3 areas of danger to be aware of.
You trust your gut more than any other input. This, I think is THE most important thing, and my guess for if second time founders are more successful, the reason why. That you even have a gut to trust. Over the months and years of the first company, we’ve all built up a sense of how to things and how to do it in a way that works for us. With Poppy, I would constantly be asking others how to think about hiring and giving equity; about raising money; about product sprints and growth. With Milo, I know how to do it, and how I can do it better and faster for me. Doesn’t make the doing of it any of any easier per se, but at least this time around I don’t have the weight of my newness weighing me down at each turn.
You can make bigger, bolder calls. Because you know the lay of the start-up game better, you can start being bolder on what you’re building, especially because it’s likely you’re able to raise more capital to do it with. You’re also building with all the hard fought learnings you gained from yes, your last startup, but also all the other experiences in your life. You’re able to connect more dots in more unique ways because you have more insight and instinct.
You can do more, because you can see more.
That said, this cuts both ways. Being a repeat founder carries the burden of knowing when a thing isn’t working and knowing that you have to make harsher calls, faster. You can’t claim ignorance. So you have to make the equally bigger, more brutal team and product calls.
You can out persist even your former self. This one stands to be really proven but, in my case, my first start-up was sort of accidental. I was curious more than anything and I found myself trying to do right by a product that just took off. To start Milo, I had to make the explicit call that I was going to do this again. That I was willing to devote the next decade of my life — of my girls’ lives — to this. That made me choose a problem and a space that I knew I could make my life’s work if I was lucky enough to keep it going. I started this one knowing that it was a marathon and have been pacing myself as such. It’s still at a sprint pace but one that I know how to maintain when and how I need to.
I could tell you more ways being a second time founder helps — established investor network, better hiring pool, focus on distribution vs. product — but in the end, all that matters, I think, is that it gives me the confidence to do a thing that requires endless boatloads of it, powered by my gut, which I trust above all. Even above my closest mentors and friends. That’s the ultimate superpower.
And the ‘downside’
And if those are the things you can count on as tailwinds, here’s what I think are the headwinds:
Any unprocessed PTSD will come back to haunt you. There’s a joke among founders that no matter what space you work in on the first, you vow to never do that again. Marketplace people jumping to saas software, saas people jumping to hardware, hardware people jumping to anything else. It’s one of those “if you don’t laugh, you’ll cry” kind of jokes.
Because what each of us works on is extraordinarily complex and we learn the hard way all the brick walls that exist in a category (by running head first into them, realizing it’s not one that can be bust through, and leading our battered bodies and teams around it). For Poppy, it was the relentlessness of building a marketplace — there was literally never rest. Fix one side, break the other and on and on you go, forever. That’s the game. Add on the labor law and trust and safety parts of a childcare marketplace and I vowed to myself to take a break from people and marketplaces and to go into “just” software.
That PTSD put blinders on me on how a true solution would work for what I’m building with Milo until I was willing to reconsider both people and a marketplace. Then, guess what? An unlock based on my ability to build with both.
The lesson? Rest. And then process that PTSD so you can build this next start-up without any of the bad baggage.
Your knowing too much can stay your hand and make you timid. There is power in the sheer naivety of a first-time founder. I was too clueless to know better, and in a lot of ways, it helped me keep going even in the face of stupid odds. This time around, I would get into my head before I could ever get going on a thing. The fear would roar louder, fuelled by the memory and pain and skepticism held by my body. I would hypothesize all the ways this thing wouldn’t work, or couldn’t make money or would just result in weeks wasted. Ironically, I wasted weeks because my “knowing too much” got in my own way.
In time, I had to learn to just focus on my best testable hypothesis. To use all my knowledge to craft that, and then to just get going. Knowing better can be a good thing — but let it power your gut, not cloud your mind.
It can keep you in the game too long. It almost doesn’t matter how your first startup went. The second go at it comes with higher stakes. If you knocked it out of the park, you’re being chased by the ghosts of a “one-hit-wonder”. If you failed and either ended up as an “acquihire” or a shut-down like Poppy, you’re been chased by the ghosts of “don’t actually have what it takes”. Either way, this point of ego and pride plays with your mind and how long you persist on a thing. I’ve found myself going longer on a product or a direction because “it had to work” and “I couldn’t fail” more than what actually served the company. I’ve had to honestly just get over this. To know that my worth as a founder isn’t wrapped up in the outcome of even this go at it, but rather how I go about building it. That even if this were to end again not how I wished, that I would still have a next chapter. This is really harder to do in practice than theory, especially when you have a family and bills to pay and a very real “opportunity cost”. And yet. Ironically, this can make you make the kind of bad calls that will sink you anyway. Stay in the game as long as it serves the purpose and serves you.
I love being a second time founder. But as you can see, the benefits come at a cost, as most things of value do.
Above all: I wake up with gratitude. That I’m one of the lucky few that gets to do this job. That gets to get up and try. Again and again and again. And if the cost is that I need to be as self-aware as I can, of my own limitations and fallibility, I’m okay with that.
Because breakthrough lies in the trying again and again. In the 10,000 ways that don’t work until you find the one that does.
So my hope is for the world to have countless second and third and fourth time founders, no matter the individual result.
There is magic in the trying and learning and trying again.
And I wouldn’t change that superpower, no matter all the kryptonite.