Recently, I started advising a few early stage founders and investing in a couple.

I realized today after one of those sessions that there are 2 types of problems in early stage startups: business problems, and founder problems.

I wrote down a few notes to discuss problems I saw with the founder’s execution: marketing, product, and hiring.

I was unhappy with their execution, and I felt that something was off.

For some reason, I got the inspiration to ask: are you okay? Is everything fine on your end? Before pestering them with specific feedback on their execution. That unpacked a lot, and we didn’t need to discuss the business problems.

My initial impression of this founder was very positive. High agency, gets things done, hungry, etc. However, my impression was changing as a response to poor execution in the past couple of months.

I told him “there are 2 types of problems: business problems, and founder problems”. Business problems are easy – you can resolve all of them. I can help you with those.

However, I can’t help much with founder problems.

What are founder problems?

A founder’s job is really hard. Full of existential angst, doubt, fears, etc.

Not to mention that life gets in the way: conflict with personal goals, family issues, social life, etc.

If founder issues are taken care of, all business problems are resolvable.

If there’s a delta between your plans and your execution, more likely than not, there are “founder problems”.

• Lack of motivation
  • This one is really hard to resolve. It’s actually the main differentiator between a founder that perseveres and wins, and one who doesn’t.
  • A very simple test is what Andy Grove shares in his book High Output Management: if your life depended on it, would you do it? If the answer is yes, then it’s a motivation problem. If the answer is no, then it’s a skill problem. And if given enough time, then every skill problem is also a motivation problem (you can learn it, find those who are good at it & pitch them to join you, etc.)
  • I can’t advise you on how to change this. If your life is too comfortable (the alternative of not doing it is fine) then you won’t do it. This is why founders with tough circumstances are more likely to win; it’s because they “need” to win to escape their circumstances. Those with a very comfortable safety net struggle to move, because why should they?
  • One piece of advice could be to simulate a tough circumstance if you don’t get it done (public commitment/accountability, taking a bigger financial risk, etc.)
  • If you want it badly enough, you will do it. If you don’t do it, then you don’t want it badly enough. Read Back Against The Wall
• Fear of failure/judgement
  • Do you care about people’s opinions of you too much? That’s a recipe for failure. You must want to “win” more than you want people’s approval and cheers. You must accept that not everyone will approve of or like what you’re doing. Even if those are the closest people to you.
  • Perfectionism is an excuse for procrastination.
    • He had a concern that the product he was about to launch was not “good enough”. It was far from perfect, and it wouldn’t be a much better improvement to what’s already out there.
    • I challenged him on it. Told him I as a customer have tried to search for a company to help me doing X, and I couldn’t find anything that was remotely convenient. I told him that if you ditch the current product and just have a slick landing page with a WhatsApp number where you offer the service yourself offline, that would be a 10x better solution than what exists out there.
    • It’s easy to be a perfectionist. It’s normal to feel these doubts. You might feel like your identity is linked with the product your launching, and if it sucks then you suck. That’s stupid. Just take the first step. Get the first customer. Be obsessed with delivering the best experience to them. Then rinse and repeat. Read Going Live
  • What’s the worst that could happen? It’s good to keep asking that question and reminding yourself that the worst that could happen is you learn a ton and get closer to your goals.
• Lack of accountability/structure
  • Too much freedom is crippling. Share what you’re trying to do publicly. Put yourself under pressure.
  • We operate best when there’s a clear expectation of the next milestone, and a deadline/date for that to be achieved. Set that and share it with the world or with a trusted few that you don’t want to disappoint. Read The Wolfpack
• Poor environment
  • If you want to achieve something nobody around you has achieved, you need to change your environment.
  • If your environment is keeping you too comfortable, change it.
  • All your time and mental energy should go into 1 thing: your business.
  • I asked him: if I was to tell you that in order for me to keep investing/advising, you’d need to move to X country and work 10+ hours a day on your startup, would you do it? Do you think that would make you achieve better results?
• Low Intensity of Execution
  • The only thing getting in the way of you achieving your goals is execution. Why can’t you 10x the intensity of your execution? (do more in a shorter period of time)
  • Read Beast Mode

There are possibly others, but that’s it for today. To avoid procrastination, I’m walking the talk and publishing this without perfectionism 🙂

It all boils down to this: how badly do you want it?

I believe we’re all capable beyond measure.

Countless cases occur to my mind of men who think that what they themselves are unable to do is impossible, who maintain that we utter words which are too big for man’s nature to carry out. But how much more highly do I think of these men! They can do these things, but decline to do them. To whom that ever tried have these tasks proved false? To what man did they not seem easier in the doing? Our lack of confidence is not the result of difficulty; the difficulty comes from our lack of confidence. – Seneca