Greg Isenberg - How to win in your 20s

How to win in your 20s

For all those in their twenties, and those who want to reminisce about their twenties, have a read below:

1. Move to a big city. Don’t have to live there forever, but being in NYC or SF even for a short while will pay you back like crazy in your 30s.
2. Be a YouTuber. You’re young, your unfair advantage is how you film. Pick a niche, share one video a day, and let it compound. By 30, you have 100,000 subscribers.
3. Be a generalist. The internet belongs to people who understand design, copy, paid ads, new technologies. You don’t need to be amazing at everything, just a generalist.
4. Accept the days. Good days, bad days. Being okay with the randomness of life.
5. Don’t send angry emails or texts. Wait 24 hours. Eat, sleep, listen to music, and remember that it’s probably not worth it.
6. Launch one new thing per year. It’s the only way to really learn to become a generalist.
7. Do everything you can to not get into debt.
8. Get insanely good at cold DMs.
9. Build a bunch of internet MRR (monthly recurring revenue). Don’t rush into building a VC-backed startup. Your odds of building your nest egg that way are tiny with VC. For 99% of people, securing the bag will be a weight off your shoulders.
10. Buy a high-quality set of headphones. When the beats are hitting, you’ll be more inspired to create and publish your work on the internet.
11. Be addicted to real dopamine, not digital dopamine. Laughing with friends. Seeing a sunrise. That’s the real stuff.
12. Create a "failure resume". Document your mistakes and what you learned from them. This helps normalize failure and turn it into a powerful tool for growth. You'll read it and be reminded.
13. Write a weekly reflection. Spend 10 minutes every Sunday to reflect on the past week. What went well? What didn’t? What can you improve? This habit helps you stay mindful and intentional.
14. Sacrificing your reputation in the short term is always a bad idea.
15. Your 20s are about variety. To learn what you like/dislike. The rest of your life will be to apply those learnings.
16. Learn to cook a few staple meals. Not only will this save you money, but it’s also a valuable life skill. Plus, cooking can be a great way to unwind and be creative.
17. Turn your quirks into assets. If you have a unique hobby or an unusual skill, showcase it. The beauty of the internet is it makes you stand out and attract opportunities.
18. Know that other people’s negativity is not yours. There are many insecure, sad people on this planet. Their sadness comes out in strange ways.
19. Travel often but have a home base. Home base keeps you grounded, travel keeps you evolving.
20. You don’t need the last word.
21. Fruit is as good as candy. Sometimes the natural version is better and usually better for you.
22. Create a personal mission statement. Clarify what you stand for and what you want to achieve in your life. This statement will guide your decisions and keep you focused on your long-term goals. It’s okay if you change this.
23. Surround yourself with people who think big. And if you can’t find them, listen to their podcasts. You’ll live a lot differently.
24. Don't get a "safe" job at a big company. You’ll learn those jobs aren’t safe. 500,000 tech workers have gotten laid off since 2022. Join a smaller company and soak up as much as you can learn.
25. Get really good at a hobby. Lots of people lose hobbies in their 20s, find one and become ridiculously good at it. You’ll have it for life.
26. Approval of others is expensive. You just need the approval of yourself.
27. Making others look bad is never a good look.
28. Create a list of energy drainers and energy givers. Put people and things in both. Update it every three months.
29. Being a friend to everyone is being a friend to no one. People-pleasers go nowhere.
30. Run a paid community. IRL or digital. But bring people together and charge for it. I use Skool for digital mostly and IRL I like throwing dinners.
31. Don’t forget about your parents/grandparents. Just because you’re an adult doesn’t mean they are out of your life.
32. Work for someone you look up to.
33. Don’t believe what you read. Most social posts aren’t really real. Focus on yourself.
34. Be good at balance. The “richest” people have the most balance in their lives. Doesn’t mean you can’t work hard. Work hard but be balanced.
35. Lift weights. Strong body, strong mind.
36. Create a “story bank.” Collect and document interesting stories, anecdotes, and insights you come across. These can be used in writing and speaking. Show up to dinners with these stories.
37. It’s not supposed to be easy. It gets easier with experience. You’ll mellow out.
38. Offer “office hours” for your skills. Set aside a couple of hours each week where people can book time with you for advice or help on a specific skill you excel in. It’s a way to give back and build relationships.
39. Master the power of silence. In negotiations or heated discussions, silence can be a powerful tool. It often compels the other person to fill the gap, sometimes revealing valuable information.
40. Turn life into a game. Makes it feel less serious, and you end up doing.
41. In my day, you’d work at McDonald’s as your first job. You’d learn a lot. Today, go work on Upwork. You’ll learn a lot.
42. It’s okay to start from zero. Everyone has. Gotta get used to it. Life is a game of starting from zero many times and climbing back up.
43. Build cash-flow. Have a job? Build cash-flow on the side with something on the internet. It might look small in the beginning, but it’ll compound.
44. Be kind, trust your gut, work hard and you'll do well.

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I hope you enjoyed.

Next up, bookmarks I saved this week worth reading

#1

Drice @driceroland This kind of wallpaper 🌱 5:29 AM • Jun 4, 2024 16321 Retweets 91943 Likes Read 117 replies

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I changed my wallpaper to this the other day, and honestly, my phone feels so much more calm. I love it. So, this is your reminder to change your wallpapers (phone/desktop).

#2

anu @anuatluru The Rise of the “Software Creator” 4:18 PM • Jun 4, 2024 241 Retweets 1698 Likes Read 49 replies

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This is so true. I'd re-read this and take the time to understand this shift that is happening right now. If you understand this, you'll understand where the world is going. A bunch of businesses to be built based of this trend.

#3

Jeremy Giffon @jeremygiffon In every single interaction in your life you bring an implicit ask. For some it's impress me, others it's confess to me, help me, compete with me, dominate me, etc. It's worth knowing what yours is and understanding how to use it. 1:42 PM • May 30, 2024 5 Retweets 132 Likes Read 5 replies

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Every interaction has an ask. Never thought of it that way.

#4

michael s galpert @msg knowing when to go fast vs slow is the name of the game 6:16 PM • May 23, 2024 0 Retweets 5 Likes Read 1 replies

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This is true. Especially with respect to launching publicly, versus to be quietly building.

Thanks for reading Greg's Bookmarks.

2 new podcast episodes are live this week How to come up with startup ideas based on nostalgia with Jonathan Courtney. This was a fun one, lots of laughs and ideas were shared. Watch on YouTube​ Listen on Apple Podcasts Listen on Spotify​ 2. Matty "The Most Famous Artist" Mo gave 3 brilliant easy to start startup ideas around the art space. Someone is going to start one of these and do really well. Watch on YouTube Listen on Apple Podcasts​ Listen on Spotify

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