While talking about entrepreneurship, we think of product, business strategy, org building, fundraising as many of the core pillars needed to create a successful venture. However, underpinning high performance across a lot of these ‘hard skills’ is the psychological jiujitsu (confidence, resilience, et al) that remains relatively under-discussed. Having faced this personally and seeing a lot of close friends across life stages get impacted by it, this is a subject close to my heart and one I intend to write a lot more about over time. This post largely centers around ‘seed confidence’ or risk appetite.
Reflecting back on the last decade of being around founders and aspiring founders, the one trait unifying everyone who ‘made it’ is their ability to take relatively large bets in life. This has implications on everything from delaying short-term personal gratification (saying no to fat paychecks, ‘chilling’) to exuding genuine belief while hiring or fundraising (both of which at the early stages require belief on the part of other people, and they can’t believe you until you truly believe in yourself) to taking ‘irrational bets’ that led them to uncover value in spaces and models most others dismissed (“small TAM”).
If this idea requires any more selling, I will leave these two quotes from the metaverse that sum it up well:
“Confidence. More than equity, more than liquidity, that’s what a man needs. I wished I had more. I wished I could borrow some. But confidence was cash. You had to have some to get some. And people were loath to give it to you” — Phil Knight, Shoe Dog
“We can say that Muad’Dib learned rapidly because his first training was in how to learn. And the first lesson of all was the basic trust that he could learn. It is shocking to find how many people do not believe they can learn, and how many more believe learning to be difficult.” — Frank Herbert, Dune
Drawing from a variety of honest conversations with founder friends over the years and my own journey dealing with confidence issues, here are tools that helped navigate the early years in our careers (and still continue to):
- Question the validity of existing power structures: Many of us develop very unhealthy relationships with power early in life. Right from our religion to our government, bureacracy, school and family, systems run on rigid pre-programmed notions of authority. PR narratives are binary — successful people were apparently born special (no!), people at the helm of large organizations have ‘figured it out’ (also no!), financial success correlates with IQ (lol). The best way to get over that hang up is to really find a chance to hang out with some of them. Michelle Obama famously said, “Here is the secret. I have been at probably every powerful table that you can think of, I have worked at nonprofits, I have been at foundations, I have worked in corporations, served on corporate boards, I have been at G-summits, I have sat in at the UN; they are not that smart.” Getting access to these rooms is not easy but the more un-filtered conversations you can get yourself privy to, the quicker you realise that none of these journeys were straightforward and obvious, that the delta in outcomes is less a function of what you’re born with and more a function of what you choose to do. Choosing what games you play is an art and you only learn it by taking that risk. There is a reason a lot of early founding team members end up starting their own companies :)
- Examine your personal default patterns: this is all the unhelpful conditioning we’ve picked up growing up. My big psychological barrier has been my strong inner critic —perhaps the voice of my dad as processed and preserved by my 5 year old self that I carried (carry?) along well into adulthood. This fear of failure / need for perfection has often come at the cost of taking high stakes bets that are so core to doing anything unusual in life. For others it might be a need to please close family and friends, being too tied to ‘acceptable’ markers of success, fear of rejection, etc. Explore both how that instinct still serves you and the ways in which it holds you back. Journalling and having an accountability buddy (ideally a coach!) on this journey are both extremely useful tools to build a deeper understanding of what gets in the way for you personally. Awareness and acknowledgement is always a great first step!
- Start with smaller bets and progressively increase stakes: Make a list of all the things you’d do if there was no fear of repercussions. Tick off items in relatively safer neighborhoods — at this point, don’t even bother thinking about what the impact is. The lesson to imbibe here isn’t about picking your battles but that taking risk is an unfairly magnified danger in our heads. I remember a founder friend who asked out 50 potential partners in a month as a way to prep himself for sales rejection before starting an enterprise software company (try this at your own risk!).
- Choose who gets to influence you: YMMV but one thing I did and still do, especially till I build up enough mental strength to completely filter away noise, is to actively avoid being around people that aggravate risk aversion or operate from a need of external validation. This also extends to the media I consume — books, movies, social apps — “every action you take is a vote for the type of person you wish to become”.
- HODL: The antidote to the doom and gloom of ‘crashing’ is really to crash more. Crash enough till you know it will pass. Till you start seeing the green shoots of what is possible when you take risk. Take time to introspect on the learnings and what you plan to carry from this experience. As Ray Dalio puts it, “pain + reflection = progress”. Self-doubt is more common than you think and is also an extremely abundant source of motivation and discipline.
To end with another of my favourite lines from Dune: “The eye that looks ahead to the safe course is closed forever.” I hope, if nothing else, this post leaves you examining the quantum of confidence you’ve had in yourself, the number of times you’ve backed your instincts and allowed yourself to make ‘risky’ choices that the world around you wasn’t open to considering. And while unlearning is a process that takes years if not decades, and nobody can guarantee outcomes, I can certainly attest to the fact that every incremental moment of backing yourself and showing up fearlessly makes the process so much more enjoyable!