Greg Isenberg is a multi-exit Silicon Valley entrepreneur and owner of Late Checkout product studio. He has:
- Headed Product Strategy at WeWork
- Been an advisor to Reddit
- Founded a startup, Islands, which was sold to WeWork
- Founded 5by, which was sold to StumbleUpon
Guest Author: Greg Isenberg
How you can get “lucky” as an entrepreneur, creator:
1. You can chill.
Sometimes, the best way to be productive and come up with the best ideas is to do nothing at all.
Allow yourself the space to just be.
2. You dare to disagree.
Lucky people don’t just go with the flow.
They challenge the status quo, question established norms, and aren’t afraid to disagree with popular opinion. True innovation starts with a different perspective.
3. You know how to listen to the fringe.
The mainstream might give you volume, but the edges give you insights.
Pay attention to the outliers, the ones who don’t quite fit in. They often see what others miss.
4. You are human, embrace it.
I know that sounds obvious, but the best copy sounds like you’re speaking to a good friend.
Jargon and lots of adjectives is unlucky. 4. You post on social, don’t scroll on social.
5. You ignore noise.
There’s more noise than ever. Deep down, you know what to tune out.
6. You’re weird.
The odd, the unusual, the things that don’t fit neatly into a category – these are often the seeds of something truly remarkable. Normal gets forgotten, weird gets remembered.
7. You accept pain, don’t suffer (pain is inevitable, suffering is optional)
8. You’re obsessed.
This isn’t about liking what you do, it’s about living it. Your work isn’t a part of your life; in many ways, it is your life. Take your mission as seriously as a life-long vow.
9. You know how to save money.
Self-explanatory. Spend less than what you make.
10. You have a bias for action.
Understand the urgency. Time is ticking.Taking swift, decisive action sets you apart.
11. You embrace the “cobbler’s children syndrome'”.
The cobbler’s children have no shoes, reflecting how experts often neglect their own needs.
For founders, this means valuing your own product or service enough to use it personally. This self-use can reveal insights you’d never see otherwise.
12. You ignore instant gratification.
The lucky path is often slow and uncertain. Resist the temptation of quick wins that don’t align with your long-term vision
13. You’ve got a bench of cheerleaders.
Success isn’t a solo journey. You need people at all levels – those ahead to guide you, those beside to walk with you, and those behind to remind you of how far you’ve come (and to help them, it’ll pay back too)
14. You don’t follow growth hacks.
If someone is telling you about them loudly on the internet, it’s too late
15. You don’t trust what you read.
Those public revenue numbers some Twitter creator is posting is probably 1/10 of what you read. Stick to your plan.
16. You build brands that pass the “T-shirt test”.
Your brand should be so good people want to wear it on t-shirts.
17. You know how to subtract.
Luck doesn’t always come from adding more features, elements, or services. Sometimes, taking away – simplifying – leads to a more powerful impact.
18. You know all about reverse mentors.
Usually, mentorship flows from more experienced to less. But reverse mentorship – seeking insights from those younger or less experienced – can open up new perspectives and innovative ideas, tapping into fresh, unjaded viewpoints.
19. You know how to celebrate the “near wins”.
Not every effort will be a resounding success. Sometimes, the near wins – the almost-there’s – can teach more and lead to greater long-term success than immediate victories.
20. You create movements, not businesses.
The most interesting businesses people rally around them. They are movements.
21. You have a 1000 true fans.
Everything else is gravy.
22. You embody “Schrödinger’s Cat in decision-making.
Just like the famous quantum physics thought experiment, where a cat in a box is simultaneously alive and dead, founders often face decisions where outcomes are equally probable and uncertain.
Embracing this uncertainty can lead to exploring multiple pathways simultaneously, keeping options open until the last responsible moment. It’s going to be okay, go back to bed.
23. When you’re reaching out to someone be short and sweet.
No one has time to read long emails.
Bonus points if you send short, interesting Loom videos.
24. You design brands that have lotus qualities.
The lotus flower remains clean in muddy water due to its self-cleaning properties.
For brands, this represents maintaining integrity and clarity of purpose amidst market turmoil and chaos. You think about this often.
25. You start with the end.
Instead of starting with what you want to create, start with what you want to change. Lucky work often comes from looking at the end goal and working backwards.
26. You know how to unlearn.
Sometimes, the barrier to being lucky is what you already know. Challenge your own expertise and be willing to unlearn and relearn.
27. You have physical density, internet density or both.
Physical density is living in NYC and meeting your business hero in a coffeeshop. Internet density is building an audience so your hero DMs you on a random Tuesday.
28. You turn your work into fun.
If it’s fun, you’re playing a game and you tapdance to work everyday.
29. You stay healthy.
Sometimes you get dealt a rough hand, but you do everything in your power to stay as healthy as you can
30. You pay it forward.
(feel free to share this post to spread it) What would you add to this list? Lots of this is easier said than done. But the idea is to work on it.
Everyone is a work-in-progress. I remember meeting some of my heroes and realizing that they have the same insecurities as we all do. Everyone is doing their best.
Keep going. — Follow me @gregisenberg for more.
Check out the original tweet here.
