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Bill Gurley’s 5 De-Mystifying Tips For Runnin’ Down A Dream In A Practical Way

Mitchell Wilson


Mitchell Wilson


Nov 29, 2023

Bill Gurley’s 5 De-Mystifying Tips For Runnin’ Down A Dream In A Practical Way

“Greatness isn’t random, it’s earned.” - Bill Gurley

With the right approach, your dreams can become inevitable.

People make it harder than it has to be. It’s hard, really hard, but doable. It’s no wonder people give up before they get going - it’s a daunting amount of work ahead to fulfill a dream. Late nights, early mornings, lots of sweat, lots of tears, and plenty of doubters. It’s no easy path. But how bad do you want it?

Plus what better have you to do? Settle for less? That sounds miserable.

Luckily, there’s a way to start right where you are right now and advance toward your dream without depending on any Hail Mary leaps of faith or plot twists.

A while back I found this insightful talk by investor Bill Gurley, titled “Runnin' Down A Dream”. It’s a 60+ minute long video, but I thought it offered a little discussed practical plan for making your dream happen.

Here are the 5 tips I pulled out that de-mystify how to catch up to the dream you’re chasing:

Follow Your Deep, Personal Interest

The word ‘passion’ has become overplayed and it’s almost nauseating at this point.

We’ve been beaten over the head with it the last decade or so and it’s time to rethink it through with a better understanding. Deep, personal interest is a better way to view ‘passion’. Curiosity is the compass. Your personal interests, especially the deepest ones, should be fairly obvious. Capitalize when you discover it.

Bill on this:

“There’s nothing that’s going to make you be more successful than if you love doing what you’re doing because you’re going to work harder than anybody else…It’s going to feel like fun. I think this is the most important decision you can possibly make in a career…”

Simply consider what you spend your time doing that gives you the most energy, what lights you up and feels like play? What feels like play to you and looks like work to others?

That’s your sweet spot.

That’s your deep, personal interest to pursue further.

Hone Your Craft Constantly

The bulk of the solution lies in this tip right here.

Bill instantly demystifies how to approach dream achievement:

“Strive to know more than everyone else about your particular craft…you have zero excuse for not being the most knowledgeable in any subject you want because it’s right there at your fingertip, and it’s free…”

There’s no good reason why you can’t be reading, watching, listening, and studying your craft constantly. The information is available, the pieces to your puzzle await you. The only thing in your way is you. You have to prioritize it. You have to confront the work. The wisdom of your craft isn’t going to hop into your brain on its own.

Bill again:

“It’s extremely important to be obsessive about understanding everything you possibly can about your craft.”

You likely obsess about something in your life and if it’s not your craft, you’re doing it wrong.

Channel it.

Develop Mentors

Learn from those who came before you.

Aside from studying up and having mentors through the content you’re consuming, also seek out a living one too. These people have either been in or are currently wearing the shoes you hope to be in. They know things and have done things you want to know and do. And if you’ve done your homework, can speak the lingo, and are ambitious - I see no reason why they wouldn’t want to help you.

Bill puts it like this:

“Take every chance you can to find somebody who can teach you about the field you want to excel in. You can work your way up the stack. You don’t have to jump straight to the top on day one. Treat them with respect. Debate things, learn from them. Document what you hear, share it with others. Try to get these mentors interested in you and your own development.”

You will have to stretch beyond your comfort zone to access a mentor. Cold email, cold call, maybe even move cities. It’s going to take some work.

But that’s the name of the game when you’re dream chasing.

Embrace Peers

Now it’s time to work with the periphery, your peers.

It would be crazy not to sync with those on a similar path with similar dreams. They are going through the same things as you, the same hurdles, the same twists and turns. You might as well cross-pollinate your ideas and radically increase the chances of both your success. Two brains are better than one. The more the merrier.

Bill’s thought here:

“Always share best practices and don’t worry about giving any proprietary knowledge. It’s a good trade. It’s just smart. If you get caught in worrying about it, you’re going to fail to advance. The activity of sharing with mentors and peers will lead to so many positive things that help you go up, that whatever the negative costs are aren’t going to come anywhere close.”

Competition, if it comes down to it, can be healthy. It makes you step it up. It keeps you honest and sharp.

Embrace it.

Pay It Back

You’ll always be striving forward for the next thing, but at some point, you are so deep into it that you become the expert and the one people turn to.

In a beautiful way, it becomes a full circle. You eventually become the mentor. And while you could write it off as being too busy to pass knowledge backward, Bill argues that you ought to take the time to pay it back.

The people who truly love their craft always do.

If you liked this and want to see Bill’s entire talk, here’s a link to his video.

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