Greg Isenburg on "How To Win in Your 20s"

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 could have 100,000 subscribers.

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 — especially in the AI age.

Accept the days. Good days, bad days. Be okay with the randomness of life.

Don’t send angry emails or texts. Wait 24 hours. Eat, sleep, listen to music, and remember it’s probably not worth it.

Launch one new thing per year. It’s the only way to really learn to become a generalist.

Do everything you can to avoid debt.

Get insanely good at cold DMs.

Build a bunch of internet MRR (monthly recurring revenue). Don’t rush into a VC-backed startup. Your odds of building your nest egg that way are tiny. For 99% of people, securing the bag this way will be a weight off your shoulders.

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.

Be addicted to real dopamine, not digital dopamine. Laughing with friends. Seeing a sunrise. That’s the real stuff.

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.

Write a weekly reflection. Spend 10 minutes every Sunday reflecting on the past week. What went well? What didn’t? What can you improve? This helps you stay mindful and intentional.

Sacrificing your reputation in the short term is always a bad idea.

Your 20s are about variety. Learn what you like/dislike. The rest of your life will be to apply those learnings.

Learn to cook a few staple meals. Saves money and is a valuable life skill. Plus, cooking can be a great way to unwind and be creative.

Turn your quirks into assets. Showcase unique hobbies or unusual skills. The internet makes you stand out and attract opportunities.

Know that other people’s negativity is not yours. Many insecure, sad people express it in strange ways.

Travel often but have a home base. Home base keeps you grounded; travel keeps you evolving.

You don’t need the last word.

Fruit is as good as candy. Sometimes the natural version is better. Frozen fruit is a great hack (like frozen cotton candy grapes).

Create a personal mission statement. Clarify what you stand for and want to achieve. This guides decisions and keeps you focused on long-term goals. It’s okay if you change it.

Surround yourself with people who think big. If you can’t find them, listen to their podcasts — it changes how you live.

Don’t get a “safe” job at a big company. These jobs aren’t really safe — 500,000 tech workers have been laid off since 2022. Join a smaller company and soak up knowledge.

Get really good at a hobby. Many people lose hobbies in their 20s. Find one and become ridiculously good at it — you’ll have it for life.

Approval of others is expensive. You just need your own approval.

Making others look bad is never a good look.

Create a list of energy drainers and energy givers. Include people and things. Update it every three months.

Being a friend to everyone is being a friend to no one. People-pleasers go nowhere.

Run a paid community, IRL or digital. Bring people together and charge for it. I sold companies before because I hosted paid IRL dinners.

Don’t forget about your parents/grandparents. Being an adult doesn’t mean they’re out of your life.

Work for someone you look up to.

Don’t believe everything you read. Most social posts aren’t real. Focus on yourself.

Be good at balance. The richest people have balance in life. Work hard, but maintain balance.

Lift weights. Strong body, strong mind.

Create a “story bank.” Collect interesting stories, anecdotes, and insights. Use them in writing, speaking, or social situations.

It’s not supposed to be easy. It gets easier with experience. You’ll mellow out.

Offer “office hours” for your skills. Set aside time weekly for advice or guidance. It’s a way to give back and build relationships.

Master the power of silence. In negotiations or heated discussions, silence can compel others to reveal valuable information.

Turn life into a game. Makes it feel less serious and more enjoyable.

In my day, you’d work at McDonald’s as your first job. Today, go work on Upwork — you’ll learn a lot.

It’s okay to start from zero. Everyone has. Life is a game of starting from zero many times and climbing back up.

Build cash-flow. Have a job? Build cash-flow on the side with something online. It might look small at first, but it compounds.

Be kind, trust your gut, work hard — and you’ll do well.