In the land of the blind, the one eyed man is king. This is the perfect medicine for the typical imposter syndrome complex. It is easy to think that because you don’t know how things are going to work out, that you are an imposter to the throne. You have no right taking your investors’ money, your team’s careers, your customer’s attention. But does anybody really have it all figured out? Aren’t we all making this up as we go? We will our ideas to power, out of sheer curiosity and novelty, and then— voila— ours becomes the solution to the most pressing problem in the world. Right?
There is nothing like numbers to kill a good story. How many times do I need to get punched in the face by this one? At some point early on in the journey, before real product market fit, you get excited by early results, which leads to overconfidence. And then, as more data starts to come in, this confidence gets challenged and then crumbles. Not so long ago I saw a startup tap into a vein of customer demand that seemed infinite. It was the perfect hockey stick. Up and to the right. An investor offered them a rich term sheet, which given their growth rate felt to them like a slap in the face. And then, like that, the signups stopped growing. They had added too many features, shifting from being problem-oriented (staying rooted in empathy for the customer’s most immediate needs) to solution-oriented (promoting the features and price points that make most sense for their business model). It is easy to see in hindsight how brittle their story was. And so they had to reframe their narrative, extend out the story over a longer time horizon, so that their actual numbers were not at odds with its believability.
If you aren’t embarrassed by what you release, you have waited too long. One could argue that in 2020, after a decade of dealing with the unintended consequences of Facebook’s “move fast and break things” mantra, that we should be more patient with our initial product releases. Yes, but that misses the point of this phrase, which traces back to Reid Hoffman. The key here is opening up to the anxious creative tension of early feedback. Yes, we only have one chance to dance, and yes, we need to lead with excellent craftwork. But we also need to ship early and often, to recognize that the perfect is the enemy of the good, and that inexact does not mean unusable. Especially in a world of instant data analysis. It is hard to overstate the importance of flipping the switch from waiting to doing, from off to on, from zero to one. In the end, this is less about design or technology, and more about our somatic state. The form of product “release” isn’t always clear. The raw emotional compulsion to act on a strong founding impulse is what is important. Beware, as if left unchecked, this impulse will wear out the patience of a team. But channeling it, and establishing a culture of frequent “embarrassing” experiments is vital.
You can’t push string. Effort doesn’t always generate impact. Some things are impossible. So don’t waste your energy. It might be the wrong time to try to raise money. It might be the wrong moment to try to recruit somebody onto the team. Be mindful of when you have leverage and control over your situation, otherwise don’t push.
You have to eat a lot of coal to shit out a diamond. I spent my senior year of high school in 1987 at Interlochen Arts Academy in Michigan. The head of the Drama Department was a chain-smoking, f-bombing ogre of a woman who really knew how to get into my head. I was an ambitious, avant-garde theater nerd who thought way too much on the stage. After rehearsing my lip-synced rendition of Elvis’ Jailhouse Rock over and over for her, I finally delivered a light moment. Without missing a beat, she growled at me: “You know, Goldstein, you have to eat a lot of coal to shit out a diamond!” And that phrase has stayed with me ever since. Rousseau apologized “I am sorry it took me such a long to write you such a short letter.” It often takes a long time to get to the point where you can express something simply, easily, purely. Steve Jobs studied Japanese calligraphy at Reed College in Oregon: one stroke, the brush never leaving the page.
No good deed goes unpunished. This hits home. Always. How often does the way we try to help somebody end up undermining the desire to help in the first place?We have our best intentions. We want to help somebody achieve their goals. And then it gets messy. Perhaps because our need to help loses contact with how they can receive it. Regardless, our spontaneous offer becomes their implicit expectation, and we get trapped in a cycle of dependency. We go from a place of abundance, to one of scarcity (where we can never do enough to satisfy them). In the end, we are the ones to blame for the drama and wasted time.
Have difficult conversations now. Do not wait. They do not get easier or better with time. That voice inside of you, the one that is so quiet you almost can’t hear it? That one. What is it saying about the person that you want to hire? Or about the new investor you want to have lead your round? When I was training for a long bike ride some years back, I remember somebody telling me that I needed to fuel myself whenever the slightest idea of eating came into my mind. That it was my body helping me to stay ahead of my hunger. Like how after an operation you need to take pain meds before it starts hurting, to stay ahead of the pain cycle. In a startup, you need to stay ahead of the drama and conflict cycle by having difficult conversations early and often.
It’s not about the money, it’s about the money. Don’t fool yourself. When it might be about money, it probably is about money. Founders argue with each other, and with their investors, investors argue with each other. The tension seeps through the organization and its cap table. Everybody comes up with all sorts of reasons for tension, but in the end it’s often just about the money (unless it’s about ego, which is often driven by founder insecurity which is a another subject worth covering). The money has a life of its own, like an immaterial energy force that is always trying to increase in value from the first dollar raised to bursting onto the public market. The money is charged with potential.
Delegate, don’t abdicate. It was 1996, I was 25 years old, and I had just started my first company, a web marketing agency called SiteSpecific. We had recently sold a minority stake to a publicly-traded direct marketing firm based in San Antonio, Texas. The CEO was twice my age and was missing a finger from a shrapnel war wound. I met him in the lobby of the Waldorf on Park Avenue. Soon we would both be featured in a cover story about startup culture clash in the WSJ. He told me that the secret to becoming a great leader was learning how to delegate without abdicating. It stuck with me ever since. The greatest challenge to a founder’s psyche: to succeed at building an organization larger than yourself, you need to break down your vision and turn it into goals that can be delegated to your team. You can’t blindly trust their execution and abdicate responsibility. You need to stay engaged, and check in on a regular basis with each team member to see how they are doing and what you might do to unblock their path. There are two gutters of a startup’s bowling lane: on the left is the risk of founder as hero craftsman, who needs to do everything himself and doesn’t trust anybody else. On the right is the risk of founder as enabling slacker, who raises too much capital, hires too many people, and loses control. Avoid the gutters.