What is the best advice for a young, first-time startup CEO?

Here are 23 points to think about, loosely organised around topic:

  1. Be careful about which investor you marry: You can’t get divorced to an investor. If investors treat you bad before you marry and things are going well, they will crap all over you when things are tough. Be vary wary of investors who will micro-manage you- they are everywhere and will make your life hell! Do not give up too much equity early on (e.g. 40% at angel), you will either have to recap or not be able to raise again in future (I have seen this happen in India).
  2. Pick terms overvaluation when raising: Do not have vanity about your valuation. Don’t require too big a valuation- you need to grow into it at the next round. When faced with a slightly better valuation and worse terms, get better terms. You are highly likely not to get the biggest outcome, a medium one is more likely…. and those terms you gave up will mean you get zero to little after the liquidation preference waterfall.
  3. Raising money is not your business model: Raising VC is not a celebration moment; It means you have to get to work. You give up equity for the money, which chips away on your upside and means the company exit value needs to keep getting log bigger… Raising sucks. Hate the burn you have. Do not rely on VC $ and hate every dollar you have to spend
  4. Don’t expand too fast: Don’t launch in multiple cities. Start with ONE home market you are going to dominate.
    1. Figure everything out about your business model, then add one more market. You need to transfer learnings and document how things work, so people don’t duplicate learnings (it costs $ to figure out things, especially with marketing).
    2. Don’t be goaded into expanding too fast. Fab’s expansion to the EU was a death knell. Rocket goaded them to expand before they had validated their model. Very bad idea to ‘go big’ before you are ready. You end up going home with nothing.
    3. Your raises will be based on proving you can nail it and scale it. If you say the raise is to add more countries and you don’t, you can’t come back with the same story when you run out of cash. This is how one of the most famous startups in Singapore crashed and burned.
  5. Spend time thinking how to give performers more work: Hire awesome kids (cheap) and spend time thinking how to let them fly, and fail for themselves. Amazing kids can do more than you reasonably think. Do less yourself, get them to do more, but be a role model or they won’t respect you
  6. Keep selling the dream: You got people to join because of your vision; don’t stop selling it. Sell it every day! You are not doing this enough. Remember to ‘start with WHY’
  7. You don’t know anything!: Remember you don’t know anything. Listen more than you talk. Seek to understand, before you seek to be understood. Staff are ok with you not knowing everything (other than the high level) and depending on them- they hate an insufferable know-it-all. The best idea should always win. Go Google style and ask for data – any decision can be changed with data
  8. Don’t hire fast: It seems so tempting, but really, it does screw you. That coder ships, but is paranoid and thinks people are being mean to him. You’ll end up wasting a lot of energy bitching about him and figuring out what to do, instead of just finding someone with better fit.
  9. Get the ESOP done: You may think you have other priorities, but if staff don’t have their shares sorted, they are pissed. ESOP done means your staff feel like owners. ESOP not done means you are a dick
  10. Have the lowest salary: Set the standard for staff. By being the lowest paid, it’s really hard for new staff to argue to have outlandish salaries. Your margin is your opportunity to hire
  11. Reduce your focus: Do less, but do it better. Everyone picks too many battles. Really bad idea
  12. Ship. No construction sites: If you are moving, pick one optimisation each week and ship it. Do not pick 5 and deliver on none. Just keep getting better
  13. Work hard, but not too hard: Stop watching Netflix, you don’t have time. Working hard means a min of 12 hours a day, 6 days a week. There is no substitute for working your ass off- it doesn’t matter how smart you are if you don’t apply yourself. But, don’t work too much. This is a marathon not a sprint. Take Sunday off and shut down- you DO NOT want to burn out. What does that mean? It means you can’t face reading emails anymore etc. You just can’t face it.
  14. Learn every day: There will never be time to read a research report, or learn about a new competition tomorrow. Don’t obsess about extracting all the information in a good report- you won’t have time to read it more tomorrow. Learn today so you are smarter tomorrow, and done is better than perfect
  15. Hire smarter than you, then get out of their way: You need great people. The death dumb spiral is: A>A, B>C, C>D, D>…Z.
  16. Know your numbers: You need to know all your key metrics off by heart. Track a few daily, but check all the numbers at least weekly. Not only do you need to know them, but investors will be impressed if you do and aghast if you don’t. Staff also think you are magic if you know their numbers better than they do
  17. Your business model is wrong: You think what you are doing is right, but you are probably wrong. Your unit economics are not calculated right, or overly optimistic. LTV>CAC or 3x sounds good, but you really need 5x. Assuming your #s work is something you need to be totally paranoid about
  18. Do finance right, start clean: Finance will f*** you if you don’t keep on top it. Just be on top of everything from the beginning. Set up a chart of accounts, file receipts. Use Expensify at least
  19. Focus on burn rate and runway: You are living on borrowed cash and time. You have no time. Don’t waste cash. Don’t make hires you don’t absolutely need. Unless staff are threatening to leave, you don’t need new people etc.
  20. You are what you measure: Many staff will chase the goals you set, so be careful. Make sure your goals are the right ones. For salespeople, know they will game any comp scheme. So make it as simple as possible.
  21. Have fewer targets: If you have 50 metrics for mgmt, no one knows what matters. There should always be ONE thing you are focused on the most, and all staff should know what it is. There can be supporting metrics, but they should contribute to achieving that number
  22. Busy vs. productive: Do the right things. You can convince yourself you are getting s*** done when you are spinning tyres. Real traction matters.
  23. Don’t go to startup events: If your customers aren’t at Disrupt, why are you there? Get to the fintech event where your bank clients are etc. The tech community loves to jerk each other off. It’s a false sense of security. The people building real startups aren’t at the events

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