There are these two young fish swimming along and they happen to meet an older fish swimming the other way, who nods at them and says ‘Morning, boys. How’s the water?’ And the two young fish swim on for a bit, and then eventually one of them looks over at the other and goes ‘What the hell is water?’ - David Foster Wallace
I read that quote in Just Evil Enough, a new book on subversive marketing by Alistair Croll and Emily Ross. The book reminds us that to be disruptive you need to be subversive, and to subvert a system you need to know you’re part of one.
Founders are part of many systems. The one I’ve been thinking about lately is the system of startup experts. Because we’re living in a culture of experts.
I can hear their influence when I listen to the questions I get in my founder workshops:
“What unit economics is a Series A VC looking for?”
“Should I have a discount on my SAFE?”
“How do I show a big TAM?”
I have no problem with the questions. But I always get the feeling founders are grasping at surface level tactics but not understanding what‘s underneath. I think what they’re really asking is “what's the right way to do it?” The correct way according to top-tier VCs and billionaire founders.
That’s troubling because it tells me founders believe there is a set path to success, a set of secrets they need to discover. They need to be in the know.
Let’s look at some examples of conventional startup wisdom:
- you need to live in a tech hub
- the best founders go to top tier universities
- you must have a background in your industry
- you must have a technical co-founder
- never start a company with your spouse
I mention these because they aren’t true. Not checking these boxes does not disqualify you from becoming a Unicorn. Super Founders by Ali Tamaseb specifically debunks these myths. The Founder’s Dilemmas by Noam Wasserman also has some surprising findings. Like co-founders who are related outperform those who aren't.
Founders are busy. Grabbing a framework or playbook is obviously attractive. The problem is, as soon as someone publishes a playbook, another person comes along to blow it up. Because that’s what disruption is.
In the expert soup we’re swimming in, the most important ingredient is certainty. The more certain an expert appears, the less important what they say matters.
A recent example is Founder Mode. I feel like I'm obligated to love this idea because I’m a founder and I respect the special abilities of founders. I like Brian Chesky and Paul Graham.
But I struggle with just one thing: I have no idea what it is.
Is it micro-management? Because someone else already invented that, unfortunately. Perhaps it’s micro-management but done by the right charismatic leader, i.e. not just any hired-gun CEO. A couple come to mind: Elizabeth Holmes and Sam Bankman-Fried.
Until someone can explain what founder mode is, or isn’t, we’re left mostly with a focus on who said it, not what they are actually saying.
That pretty much sums expert culture.
A more general example is how VCs talk about what they're looking for.
Unless it is a late-stage fund, which is more like traditional capital than venture capital, founders need to take what they say with a grain of salt. Because the VC who has never generated a return on a fund appears just as certain as the O.G. The most precisely-articulated fund thesis could be right or wrong. We won't know for about a decade.
That blog post investors write about “things I hate in founder pitches” is all theory until the next great founder walks in the room who doesn’t fit the mold. Because early stage venture capital has always been and will always be about weak signals.
No matter how certain fundraising advice is, founders should keep in mind that the VC on the other side doesn’t really have an objective checklist. So don’t try to check off all the boxes.
I feel like I’m stating the obvious. But like Wallace's fish, it’s only obvious when you realize the system you’re swimming in.
Entrepreneurship wouldn’t exist without a healthy dose of exuberant naïveté or irrational certainty. Not all certainty is bad.
But it doesn’t matter how successful someone is or how loud their certainty is.
What matters, to you, is whether they’re right. On that journey it’s better to have a skeptical mindset and a default question: I wonder if that’s true?
