On Authenticity
And why it’s the most important characteristic of your early-stage startup
Show yourself. I'm dying to meet you.
Show yourself. It's your turn.
Are you the one I've been looking for all of my life?
Show yourself. I'm ready to learn.
-Elsa (Frozen 2)
Why are you even here? Why are you doing this to yourself?
Why are you building a startup when there are so many better options out there for you?
If you’re a founder, it’s likely that you’re incredibly smart. You can go get a job. You can make good money. You can be one of the many and blend in just fine. So why is it that you decided instead to jump into the abyss - a place where the expectation on a good day is that you get far more “no’s” than “yes’s”?
The opportunity cost for the best founders is incredibly high. You could be learning, earning, building somewhere that already has deep product-market fit. On a risk-adjusted basis, being a founder is definitely not the best path to earning money. It’s highly likely that your early-stage company will fail, and even as you find traction and build, there are too many potential headwinds to count. How about all of the unicorn founders who went to 0 after ZIRP ended and the goal posts shifted? How about founders who had to raise on a 3x liquidation preference just to keep the lights on, and the value of their and their team’s common stock got wiped out? Or the ones who thought they were on path to a Series A but ended up coming nowhere close and had to lay everybody off? Does that semi-secure job at Google or Amazon or Stripe look better now?
Startups are fucking hard.
If you’re still here - if you’re still building in spite of this - then you passed the first test. You’re masochistic enough to earn your title as a founder. Now it’s up to you to keep it.
It’s my belief that the best way to do that is to be…yourself. Is that simple? Is that hard? Is that the dumbest thing you’ve ever heard? Maybe to all of the above. But I think it’s true.
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What is authenticity?
Think about the weirdest impulses you have as a person. Think about what your best friends know about you but nobody else does. Think about the thing you don’t want to talk to your investor about. Now give those things a hug. You’re starting to find yourself, and that’s a really good thing.
As a founder, you really don’t have time to be anybody other than yourself. Founders often feel naked. Your whole life is on display. It’s likely that you’re going to fail. Your parents and family have no clue what you do and ask if you’re ever going to go back to a “real job”. Prospective investors say no. Prospective customers say you’re too early, or that they went with somebody else. There’s nowhere to hide.
So here’s my argument: don’t hide. Go contrarian to your founder peers. Go contrarian to what’s expected from you. Show your losses to the world like you show your wins. Show the lessons you learned and understand deeply (and talk about!) why you learned those lessons. If you’ve gone through shit in life, talk about that shit. Talk about when things were hard. And how you got past some of it, but not all of it. Talk about what you’re still getting past. Be vulnerable and open. Be you. And show how you - single single greatest asset in your early stage company - are the person to solve the problems you’re working on because of, and not in spite of, who you are. That’s power.
As an early-stage company, investors and customers are betting on you. Investors are betting that you can fight through the new set of shit you’ll endure and be a power law fund returner. Customers are betting that you can actually deliver on the promises you are making and make their lives easier, better, more productive. These are bets - part risk-adjusted calculated, part purely winging it (no matter what they say). But most of all - the common theme is you.
So give the people what they want. And go get it.
What is authenticity not?
I’ve long believed that the best founders have “strong opinions, loosely held.” You have to have deep conviction to go take on the risk and opportunity cost to build a startup, but you also need to be flexible enough to listen to the world around you and evolve as you build. That means evolving hypotheses and strategies about your business - your go-to-market, your product strategy, your hiring plan, etc. But it also means evolving your way of thinking and your approach as a founder and leader. It means you have to be quick to admit you were wrong. Because you’re going to be wrong a whole lot. And that’s ok. The best founders aren’t the ones that are never wrong - they are the ones who recognize their mistakes in motion, adjust course, and do better the next time. Incremental improvements feel just that - incremental - but there is a rich compounding effect that makes you materially better as time moves on.
The question, then, is how to reconcile the second part of the line above - the “loosely held” part - with the fact that authenticity is the most important part of being a founder. The easy way out is to view the two as mutually exclusive - that if you’re authentic you hold on to your strong convictions and don’t waiver. The more nuanced - and I’d argue more appropriate - view is that when you decide to build a startup, you’re deciding to live in the “gray” vs. black and white. In that gray lies a lot of unknown truths, and it’s your job as a founder to mine for those. And if I’m following my own advice of being authentic, this step here was incredibly hard for me as a founder.
So, then, to be authentic does not mean you’re unwilling to change. In fact it means the opposite. To be authentic is to have deep commitment and moral imperative towards mining for truth, towards mining for reason. And it’s ok (and expected) that some of the times you’ll demonstrate your authenticity is precisely when you’re showing yourself open to change.
Where can this go wrong?
There’s a really easy counterargument to this thesis. When you fit into a mold, you’ll help those around you - your customers, your investors, your employees - pattern match you into an understandable form, and fitting into that form outweighs being authentic.
I’d argue that you can’t have one without the other - that the two need to coexist. Listen, if you’re a genuine, authentic, great person, but you’re building a non-scaleable company in an industry that has gone out of cyclical favor with venture investors, you’re probably not going to raise any capital. Sorry. Authenticity won’t save you. But if you check the box of timing, size, and opportunity - which, without question, you have to do - and you pair that with the unequivocal, unabashed version of you, then you’re setting yourself up to have your best chance at winning.
Want to know the best way to illustrate this thesis in real life? Startups typically start their go-to-market with founder-led sales. The founder is the person calling on prospects, having meetings, demoing the product, and winning deals. There’s always a big adjustment moving from founder-led sales to playbook-led sales (aka a sales team). Do you know why? Authenticity. Story.
When the founder talks to me about how she beat breast cancer and is building a company around helping scale early detection, I’m taking the meeting.
When the founder talks to me about how he has lost some of his closest friends to substance use disorder and he knows the depths of the darkness that come with addiction, I’m taking the meeting.
When the founder talks to me about how she didn’t grow up learning about money, and that she realized millions of other young women were like her, so she’s building the platform for girls and women to learn about money and invest, I’m taking the meeting.
You are important and your startup is you. Tell your story, and be unapologetically you. Winning in this space is hard, but this will help you get there.
Be like Elsa, show yourself. Just don’t wait for the damn ice storm before you figure it out.