A letter to my 20 year old self

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A letter to my 20 year old self

My 20s were full of mistakes, but also some cool wins. I got to start and sell some companies.

If I could guide my 20 year old self, I’d share a few tips.
I’m sharing them with you too because they might add value to you.

1. Mentors are overrated

I always sought after mentors. I thought it was the cheat code to going further. I was wrong. It’s only a piece of the puzzle.

How I’d think about spending time with the right people:

Spend 1/3 of your time with mentors. People ahead of you. Find people who have walked the path you want to walk and try to walk like them.

Spend 1/3 of your time with peers. People on your level. Hang out with people in “your boat”. Share ideas, offer advice, support them and most importantly — listen.

Spend 1/3 of your time with people who look up to you. People who are behind you in the game of business and life. Not only is it good karma to help out, but you will learn a lot about yourself and business by helping others walk the path you’ve been on. 

Constantly edit this list of people. Keep it changing because you’re changing too.

2. Be remarkable in the right rooms

There are two types of rooms.

1. Digital rooms (aka group chats)

2. IRL rooms (aka parties, restaurants, invite-only events etc).

Both matter. I stayed in Montreal, Canada longer than I should have when I knew the action was in San Francisco, California and a plane ticket costed $500 (and I had a credit card).

When I finally moved to SF, my learning and connections went haywire. All of a sudden I was getting into the rooms I wanted. Dreams seemed closer to reality.

If you can go to where the action is, it’s an unfair advantage. Can’t move to San Francisco or NYC? I get it. Then, build the largest audience on social in your niche so you’re noticed in the right digital rooms.

And once you make it to the room, your next step is being remarkable. I like how Seth Godin frames it:

“Being noticed is not the same as being remarkable. Running down the street naked will get you noticed, but it won’t accomplish much. It’s easy to pull off a stunt, but not useful.”

If you can be in those rooms and be remarkable in those rooms, good things will happen.

3. Think bigger

I used to believe I “thought big” until I met “think bigger people”. These are people who believe anything is possible.

Think big: “What if my tweet gets 1000 likes about my product?”

Think bigger: “ What if Mr. Beast RTs me and becomes my co-founder?”

Woah is having Mr. Beast as a co-founder in my company even possible?

Anything is possible. And thinking bigger is a fun wave to surf.

Always challenge yourself to think bigger in small, medium and big decisions.

4. How to pick who you work with

This might sound obvious but there have been a bunch of times in my career where I’ve worked with smart, well-known people who turned out to be low integrity people.

And I kinda knew it from the beginning but I forgave them because I was trying to learn and accelerate my career. That’s a mega mistake and is really leading from a place of fear.

My advice to myself would be lead from a place of abundance, not fear. You don’t need to work with low integrity people. You have your pick of the litter.

I’d rather less customers but better customers

I’d rather a co-founder who lifts me up than brings me down.

It isn’t worth it. There are enough opportunities that you do not need to work with people you do not think are easy

The counter point: “Well, Steve Jobs was a nightmare to work with… wouldn’t you work with him”

No, I wouldn’t. I sleep better this way.

5. Diversify more

People always say: in order to win big, you need to focus on 1 thing.

But if that 1 thing doesn’t work out, even for reasons out of your control (like a pandemic or a recession), it’s nice to be diversified.

I like what I do now operating a holding company Late Checkout because we have a 10+ revenue streams. For example, we’re seeing record revenue months from both Dispatch and BoringMarketing.com so it’s okay if other business units may be less busy.

In a no-code, AI world, global workforce world making more revenue streams and managing them is even more doable.

Create more revenue streams and by your 30s you might be riding down a mighty river.

6. The two pizza rule

I grew some large teams in my 20s and realized how important a small team is in my 30s.

In the early days of Amazon, Jeff Bezos created a small but important rule: every internal team should be small enough that it can be fed with two pizzas.

The goal wasn’t to cut down on the food bill. It was, like almost everything Amazon does, focused on two aims: efficiency and scalability. The former is obvious.

A smaller team spends less time managing timetables and keeping people up to date, and more time doing what needs to be done. But it’s the latter that really matters for Amazon.

7. Get to the point

Whatever it is you’re doing, get to the point.

Have to fire someone? Get to the point.

Writing a blog post? Get to the point.

Fluff is not cool. Getting to the point is.

You are empathetic by getting to the point.

8. Do more founder meetups

I used to hangout with 6 other founders in a house in LA every few years where we chatted startup ideas for 72 hours. The first one I attended I was 23 years old.

This was the invite to the first one from my friend Dario Meli (Co-Founder Hootsuite) who I met at SXSW in 2011

Some of these people I’d just reach out to on Twitter and said you should come. Surprisingly, really cool people came.

2013 with me, Dario (Co-Founder of Hootsuite), Rob (Co-Founder of VidIQ), Milun (Partner, Expa), Julien (Co-Founder of Breather, now Practice)

Some major big ideas came from these meetups. For example: Julien Smith refined his idea for Breather which ended up raising $250M+. Nicholas Reichenbach refined his idea for Flow Water which ended up becoming a publicly traded company (and Gwyneth Paltrow loves it too!)

I did this every few years. I wish I did it every year.

Do more of this.

9. Tune In & Tune Out

Tune in to the things that matter and that you care deeply about. This could be your work, your relationships, or your hobbies.  Tune into yourself. Be yourself and let the “me flag” go wild.

Tune out the things you can't control or don't matter, such as politics or the news cycle. Focusing on the things that matter to you will help you stay motivated and focused on your goals.

So there you have it — those were some of my top pieces of feedback to my 20 year old self.

If this post was interesting to you or a friend, share it with them. It might be helpful.

Be well,
Greg Isenberg

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