3 Lessons From A Dinner With 8 Millionaires


The other night I went out to an inspiring dinner.

It was for young entrepreneurs.

There were 9 of us in attendance.

Nearly all in our mid-20s.

Everyone at the table had created at least one impactful and profitable business.

Some had bootstrapped.

Some had gotten investments.

But all had been scrappy.

And, despite their success, every person at the table was so humble.

They openly shared their mistakes and lessons learned.

I came out of that three-hour meeting bewildered.


Stoked to realize the impossible.

And I also left with three great lessons.

Three points I had never thought about.

That have now profoundly changed my approach towards entrepreneurship.

Here they are:

1. Get some early wins under your belt

This came from a friend who cofounded the popular Pop Sockets (those grips everyone has on the back of their phones). Here’s what he explained…Winners want to work with winners. If you want to be involved with winners, you have to get wins early and quick. They don’t have to be huge wins either. It can be a video that gets some news coverage or a small profitable business that you started. What matters is that you created something tangible that people liked and found useful. And then you move onto the next one. So, create fast. Publish fast. Sell fast. Win fast. Then you’re more likely connect with others who’ve done the same.

2. Do less

The biggest regret that kept coming up was that these entrepreneurs had spread themselves too thin. They hadn’t focused on the one thing they could be really good at. But once they realized they were getting distracted, they all scaled back and narrowed their focus. And from that focus, they saw immediate returns. As Peter Thiel wrote in Zero To One “Instead of pursuing well-rounded mediocrity, be great at one thing.” That leads me to the next point below. And to more Peter Thiel.

3. Don’t Compete

The two founders with the largest companies at the table were the ones that had created completely unique categories for their products…ones with no competitors. These companies were Pop Sockets and Liquid IV (a healthy electrolyte drink mix that hydrates you 3x faster than water). There were no other brands on store shelves next to them when they launched. This is what’s known as the Blue Ocean Strategy. Blue oceans are areas of the market where there’s no competition. Red oceans on the other hand are filled with lookalike products and competitors fighting for dominance. Peter Thiel, a Blue Ocean Strategy proponent, wrote “All failed companies are the same, they failed to escape the competition…The more we compete, the less we gain.”

I was blessed to be at that dinner.

Blessed to be surrounded by such young and motivated people.

I’m still trying to absorb these lessons.

But I’d like to add one more.

Maybe the most important one…

Surround yourself with badasses and listen to what they have to say.

Or as Questlove said, “The only mofos in my circle are people that I can learn from.”