I’m going to skip the generic advice.
You’ve read “fall in love with the problem, not the solution.” You’ve read “talk to your customers.” You’ve read “hire slow, fire fast.” Everyone says these things. They’re true and they’re useless because they don’t tell you what they actually mean until after you’ve learned them the hard way.
Here’s the specific stuff. The things I got concretely wrong that nobody warned me about in a way that landed.
I Confused Motion With Progress
In the first 6 months I was extraordinarily busy. I was in meetings, sending emails, building decks, attending events, having coffees with advisors, iterating on the product, hiring, managing.
I was also not making meaningful progress.
Busyness is the founder’s most seductive trap. It feels like work. It looks like work. It produces the anxiety relief of constant activity. But most of it is displacement — doing things that feel productive instead of doing the one hard thing that actually matters this week.
The question I now ask every Monday morning: “What is the single most important thing I could do this week that would change the trajectory of this company?” And then I do that first, before anything else, every day.
I Hired for Potential Instead of Proof
I gave enormous weight to intelligence, attitude, and fit. I gave insufficient weight to evidence of actual output.
Smart people with great attitudes who can’t do the specific job you need done right now are a luxury. Early-stage startups cannot afford potential. You need proof — specific examples of someone doing exactly what you need them to do, at a comparable level of ambiguity and resource constraint.
The interview question I didn’t ask enough: “Show me something you built or created in a previous role that you’re proud of. Walk me through exactly what you did, what was hard about it, and what you’d do differently.”
I Treated Investors Like Bosses
After our first raise I unconsciously restructured my behaviour around what I thought our investors wanted. I optimised for metrics I thought would impress them rather than metrics that reflected real business health. I delayed hard conversations because I didn’t want to report bad news.
Investors are not your bosses. They are shareholders. The relationship works best when you treat them as informed, interested parties who have given you money to do something specific — not as authority figures you need to perform for.
The best investor relationships I’ve had are the ones where I’ve been uncomfortably honest about problems early. They can’t help you if they don’t know what’s actually happening.
I Underestimated How Long Everything Takes
Double every timeline estimate you have. Then add 50%.
Not because you’re bad at planning — because startups operate in conditions of genuine uncertainty where the things you’re depending on are themselves depending on things outside your control. A key hire takes 3 months longer than expected. A partnership takes 6 months to close. A feature takes twice as long to build. Regulatory approval takes a year.
This isn’t pessimism — it’s the empirical reality of building something new. The founders who plan for it maintain their composure. The ones who don’t spend most of their time in crisis mode managing slippage.
I Underinvested in My Own Development
For the first 18 months I read almost nothing, talked to almost no mentors, and did almost no reflection. I was too busy building.
This was a mistake. The quality of your decisions is the quality of your company. The inputs to your decisions are your mental models, your knowledge, your perspective. If you don’t invest in those, you make the same category of mistake repeatedly until something forces you to change.
One hour a week of reading, one honest conversation with someone further ahead than you per month, and one hour of genuine reflection on what’s working and not working — that’s the minimum viable investment in yourself. I wish I’d done it from day one.
The One Thing I’d Tell Myself
Do fewer things better.
Not because simplicity is virtuous — because your attention is the most finite resource in your company, and spreading it across 12 priorities means none of them get enough of it to actually move.
The founders I most respect have an almost uncomfortable clarity about what they’re working on and what they’re not. They say no constantly. They disappoint people regularly. And they make more progress in a month than most founders make in a quarter.
That clarity is a skill. And like all skills, it gets better with practice.
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