Since the sale of our company, a lot of friends and fellow founders have reached out asking for advice. It’s made me reflect on how easy it is to believe that what worked for me must be some kind of universal truth. But most advice is at risk of being little more than a single data point dressed up as wisdom and, frankly, I’m not sure what worked for me will necessarily work for others.
Brainstorming session in Porto, Portugal (Aug 25)
The illusion of authority
Once we’ve successfully ‘done’ something, it’s easy to start living with an overinflated sense of having acquired a unique knowledge. The heightened attention we receive from the people around us, coupled with our increasingly mechanical regurgitation of oversimplified instructions, can make it tempting to feel a level of authority on a certain topic. With increased credibility also comes a greater likelihood of people actually listening to what you have to say, and consequently a greater responsibility to measure your words carefully.
I don’t write this to diminish my own growth but to keep myself honest; the series of events and decisions that lead to our outcome may very well be applicable to someone else’s path. And also may very well lead them astray.
Thanks, but No Thanks
I’ve thought about some successful founders who have offered me advice over the past few years. During YC, a founder friend insisted we needed to raise at least $5M to survive the unpredictability of enterprise sales cycles. Had we followed that advice, we’d have given up 12% more of our company and significantly altered the financial attractiveness of an early exit.
Similar nuggets of wisdom would have delayed our exit by 2-3 years; likely prevented me from meeting life partner (by virtue of where I chose to live); and conscripted me to the pool of founders who build their companies from a place of fear, rather than love. People mean well, but “what worked for me” is not the same as something which is universally applicable.
The Smart Intern Shadow
Even if my advice sounds good, a big fear of mine is that in practice it is hollow; sharing polished platitudes that don’t actually reflect my way of working.
I often imagine that an aspiring founder is coming to shadow me for 2 weeks – closely following my rituals and routines. The mere thought sheds light on the disparities between what I say and what I do.
Despite being a proponent of automated systems, efficient working and difficult conversations — this thought exercise has showed me the messy reality: my clunky LinkedIn tracking, the half-kept dream of inbox zero, and my tendency to avoid uncomfortable pricing conversations with prospect customers.
A close cousin of hypocrisy is idleness. I have many times found myself seeking advice as a mechanism to delay action. In many situations, if we’re honest with ourselves, we actually know pretty well what we should do. Instead, we continue to seek out wisdom from more trusted sources, often as an escape: a way to prolong the period of indecision and avoid committing to a path of action.
Accounting for Luck
Perhaps the biggest blind spot in giving advice is how little we account for luck. When I tell friends I was lucky, they push back — crediting work ethic and decision-making. But many events outside of my control fell neatly into place.
In general, we greatly overestimate how much control we have over the wins, and we downplay the role of luck in the losses.
Why is this important?
- People who ‘succeed’ but are not aware of the role of luck in their outcomes are likely to overestimate their own ability.
- People who don’t succeed can end up blaming themselves far too easily, or giving up prematurely.
As Morgan Housel points out in The Psychology of Money, it’s usually worth remembering that extremes make for bad role models. Outliers are so often shaped by chance, and their lessons are the least repeatable. This was one of the things I liked about Y Combinator: with thousands of data points, their patterns were broadly generalizable.
Becoming Wiser
Socrates said, “The only true wisdom is in knowing you know nothing.” Einstein elaborated, “As our circle of knowledge expands, so too does the circumference of darkness surrounding it.”
People pay attention to the decisions you made, when they should be paying more attention to how you made them. Trust yourself – people can give you advice until your ears bleed, but ultimately you’re the only person who can determine what makes sense for you.
I write this post as a preface to everything that is to come and to hold myself to account when sharing my own learnings. Wisdom isn’t in following someone else’s playbook. It’s in building the confidence to decide, under uncertainty, for yourself.
Stillness & Scale 