How to Succeed In Startups (Without Getting Lucky)

1. If it doesn’t feel like the market is pulling you, it’s not. Consider if the friction in your business is a function of poor market picking vs poor execution. The best markets forgive horrific failures of execution.

2. Build something people want, not just what you want. You may think you know how to actualize something people want, but can’t articulate. Maybe so, but that’s also a way to delude yourself, so ruthlessly prove they actually want it.

3. Be resilient to the point of being relentless. Successful startups are the culmination of repeatedly messing up, yet not dying. Over many, many years. As you iterate, you’ll gain new opportunities to hit product-market fit.

4. Practice emotional stability. Celebrate the wins, but know it’s never as good as it seems. Recognize the losses, but know it’s never as bad as it seems.

5. Pursue a mission that is bold / serves a greater purpose / is the future, but don’t forget that in the end, ability to deliver growing positive cash flow is what will define whether your startup succeeds or fails.

6. Angel or VC money can make otherwise great operators lazy. Experiment like you have no money, even if you do.

7. Be real and get real. Be your own worst critic. Get to ground truth before anyone else. Discourage vanity metrics.

8. Focus on your customers, not the competition. Satisfied customers are not enough. Generate fanaticism and love.

9. Sending regular investor updates is a forcing function for progress or problem identification and a way to nurture alignment that can be redeemed in future times of need. Go silent at your own peril.

10. You can build your business like a flywheel or like a hamster wheel. Build a flywheel. The more customers / users, the easier it should be for you to deliver a superior experience vs anyone else.

11. Remember that you can lower or raise the bar with every new hire. Always raise the bar in at least one area with each hire. And raise it by hiring based on likely trajectory, not simply past experience.

12. Hire people who are either obsessed with your mission or who are obsessed with excellence in their craft. Preferably they’re obsessed with both.

13. Commit to clear communication at your startup. Practicing effective communication will be a lifelong evolution for your company and you.

14. High margins provide high margins for error.

15. Scrutinize the capital efficiency of your model. Don’t let yourself or customers turn you into a lender with the best rates.

16. As founders we are accountable for everything that goes wrong. The Board is dysfunctional? The VP Sales missed their targets? Marketing overspent? Our fault; fix it.

17. Society is optimized in the present for the past. When you build the new, societal pressure nudges you down paths of consensus & external validation. Yet that’s not how you’ll build the future. Follow the paths of truth, even if you must initially move forward alone.

18. Never let yourself become jaded. Keep that optimism that got you started in the first place. The canvas is waiting.