1/ The first 18 months of a startup: After starting my 2nd company in 2019, I decided I would write down useful lessons I learned or re-learned along the way. Some were hard-earned & others required steady focus. A thread that I hope may help other founders starting out
2/ Clarifying your plans: the first thing I did was write down a 7-page Elon Musk-style master plan. Write down what problem you plan to solve, how you’ll solve it, and why it’s important. Then have your smart friends critique it. Let no valid question go unanswered.
3/ End every conversation with an expert about your industry with: “Why do you think I am going to fail?” to lean into brutally understanding what you need to de-risk.
4/ Think of a way to make your users have some skin in the game enough to yell at you to make your product better. Charge or trade for it early on. Waiting for your product to be “good enough” reduces the amount you’ll learn each day. The first set of users paid me $20 on Venmo!
5/ Occasionally someone you respect will give you unsolicited advice that may cut you down. First, absorb it. Later, try to put their advice in a way you would’ve wanted to give yourself. This removes the hurtful part allowing you to hear it in a way you can benefit from.
6/ Rolling out of bed in my pajamas and getting back to work with things precisely as I left them was the most underestimated superpower that brought me joy, focus, and speed — I had forgotten how much goes into getting ready for work.
7/ Learning from users is a practiced skill just like programming. If you don’t have experience, make a plan. Start with simple questions, then go deep. Here was mine going into early customer interviews
8/ Be married to the problem, not the technology. If you’re married to technology, you might easily give up due to stress induced by setbacks or boredom. Being married to the problem will motivate you to have the perseverance to continue through hard times or tedious work.
9/ As your relationship with your co-founder changes, there will be times of tension. Confront issues early. Be explicit about how you will divide & conquer. Lean on each other’s passions. Don’t confuse working style differences with how the company ought to work. Get a coach.
10/ I think startups often take half pivots early on. Mine did. The 1st idea might be wrong but if you stick w/ it a bit longer, you’ll often discover a deep problem people care about. All that’s stopping you is if you want to run that company to achieve that particular mission.
11/ Sometimes smart people didn’t like my idea. You don’t need to persuade everyone! Instead, I used it as an opportunity to understand their opposition & worked hard to see the truth of their opinions. I used it as a moment to strengthen my understanding from a smart critic.
12/ During the first 6 mo of my startup, I largely focused on the eradication of risk: Will people want this? Will people pay? Can this make a profit? Can it scale one day? Will the tech work? All in the pursuit of what will kill me? You just need to know there’s a solution.
13/ If you’re worried about something that will cause your inevitable demise, use my patented Threshold of Worry (tm): 1. Set a quantitative value for the worrisome issue. 2. If it’s above the value, worry! 3. If it’s below the value, focus on the next risk & ignore
14/ Every month I ran my current goals/plans by another founder outside of the company. I found it better to assume my current thinking had a subtle fatal flaw I couldn’t see. That will often save you time or make you think differently enough to break out of a local maxima.
15/ Early on, each hire should be a little anti-sold before they join vs only passionately persuaded. Every startup has setbacks, makes mistakes, might pivot, and must overcome unforeseen obstacles. The early team must be sufficiently optimistic & capable of rapid recovery.
16/ Momentum is oxygen for a startup. Without momentum, you let fear, uncertainty, and doubt cause your demise.
17/ When building a startup: If you have fear, de-risk by talking to users. If you have uncertainty, build a prototype to rapidly rebuild your conviction. If you have sudden doubt, sleep. Try again tomorrow.
18/ The first goal I set for our company was narrow: make 10 happy users use our product. A happy user uses it, pays for it, and organically praises it. Focusing on a few wonderfully happy users is a better recipe for great retention. Then go from 10 → 100 → 1K → 10K → 100K.
19/ I was ruthless about ensuring I had as much deep work time as possible. Live somewhere boring. Eliminate meetings. Don’t meet investors if you’re not raising. Build a rhythm each day that enables the largest chunk of hours to get great work done. Users will notice your pace.
20/ If you’re a 2nd-time founder, resist the urge to button everything up. It’s a trap that makes you think you’re doing meaningful work. The first time around this blissful ignorance helped me focus on what mattered most: making a great product. It’s okay for things to be messy
21/ Your company culture doesn’t need to be set & written in a handbook on day one. I think culture is best formed organically & needs time to bake with a small team. From there, you can discover what works & what breaks. The values of a company need not be preserved, they evolve
22/ Last but not least: talk to users. talk to users. talk to users. talk to users. talk to users. talk to users. talk to users. talk to users. talk to users. talk to users. talk to users. talk to users. talk to users. talk to users. talk to users. talk to users. talk to users.
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