What I Would Tell the Entrepreneur I Was at 25

If I could sit across from my younger self, I wouldn't tell him to dream smaller.

That would be a waste of a conversation.

I would tell him to stop treating every warning as an insult.

At 25, confidence and ignorance can be difficult to distinguish because both speak with extraordinary enthusiasm.

Being capable is not the same as being ready

When you figure things out quickly, you start assuming you can figure out anything in time.

Sometimes you can.

Sometimes the cost of learning is higher than the problem deserved.

I'd tell him to learn cash flow before he needs to. Get agreements in writing. Think about incentives before trusting declarations. Ask one more uncomfortable question before signing.

None of this makes you timid. It makes you harder to surprise.

Don't confuse pace with progress

There is a thrill in being constantly occupied.

New company. New offer. New contact. Another opportunity that might change everything.

But a crowded calendar can conceal a lack of direction.

I'd ask him what he was building that would still matter if the adrenaline disappeared.

I'd also tell him that talent does not exempt him from consistency. Especially when his brain is capable of spectacular bursts followed by spectacular boredom.

Be careful who you become to win

This one would probably annoy him.

Winning is not only about what you achieve. It's also about which habits you strengthen along the way.

If you use anger to fuel every decision, don't be surprised when success fails to make you peaceful.

If you use work to avoid difficult conversations, a bigger company won't solve the relationships you neglected.

And if you measure your worth by outside approval, the crowd will never be large enough.

I would still encourage him to build.

I would just ask him to notice the person doing the building.