Check In

Check in

Welcome to the club. I am so proud of you. You made it to the few, the proud, the people who actually take action. Be proud of yourself. You will never suck worse in your whole life than you did these last two weeks.

So: these last two weeks, what went right and what went wrong? Most importantly, what did you learn from each failure?

Your relationship with yourself and failure

The number of people selling something they don’t believe in is devastating. If you just want money, stop chasing. Be 100% committed long term, be selfless, and don’t worry about short-term feedback. Give your audience what they need, not what they want.

I have three purposes: to prove you can be honest and kind and make a bunch of money, to be a rough stone rolling, and to have an impact. I wanted an arena to step into, like the man in the arena. A place to get roughed up.

So whenever an opportunity comes my way I ask: will this refine me as a person, and can I use kindness and honesty to grow this business? If yes, I’m in. If no, it doesn’t align, and I move on quickly.

If I make $500,000 a year being kind, that’s decently impressive. If I make $5,000,000 a year being kind, that’s incredibly impressive. If I want to have an impact, I need to make more money. Not to buy a yacht. To make a difference.

People give up when their purpose is smaller than their pain.

A purpose bigger than money puts fuel in your tank when things are tough. It’s how you get through the dip and come out the other side. If you want long-term success, have a long-term vision that can be your north star when it doesn’t feel worth it.

This is a group about leadership as much as entrepreneurship, and leadership is about vision and decision making. When you know who you are and who you’re trying to become, you can make confident decisions and take meaningful action.

The dip

Talk to each other. Share with each other. Help each other out. At this stage of your life you aren’t necessarily trying to make money.

Between you and great success are milestones: life lessons and experiences. Get as many as you can, as young as you can. They are ingredients in a recipe. Mentorship is one. Real-life experience is another. Problem solving and dealing with failure is another.

Go round up ingredients, and don’t get too hung up on what the business is. Experience is the key. Don’t wait for your future wife to show up before you learn how to talk to girls. Get some reps, so when she walks into the room you’re not an amateur. (Good dating advice, and also an analogy about starting a business.)

Entrepreneurship

One thing I’ve chronically under-discussed: it is incredibly hard. Long days and nights of constant work, and the people you want to date thinking you don’t have a real job.

What it might look like

You’re in college. One friend is pre-med and knows exactly what the next 40 years look like. Another is pre-law, same thing. People are impressed. You say you’d like to own your own business. You have no idea what that means or where it goes, and nobody is impressed. They’ll think you’re poor and sad until you prove yourself.

What it might cost

Ego. That’s how people end up pre-med or pre-law: it sounds good and looks cool from the outside.

Certainty. People don’t start businesses because they’re scared it will fail, while they work a corporate job that can fire them the second someone cheaper shows up.

The illusion of certainty. There are three jobs: working for yourself; working for someone else, where you trade real security for the illusion of it and get very little time freedom; and working as a professional, where you give up the upside and your time in exchange for some financial certainty.

What it can be

A bunch of failure and uncertainty for a long time. Trying a lot of things that don’t work. It’s kind of terrible and kind of terrifying. Then, if you’re lucky, you find an opportunity worthy of your full commitment, and your prize is to grind it into dust for the better part of a decade.

What you get: maximum time freedom, unlimited earning potential, meaningful personal growth, and unlimited positive impact on your community.

Do you want the pain of growth, or the pain of a crappy life?

There is no better place to become the best version of yourself than this refiner’s fire. Choose the right hard, instead of having the wrong hard thrust upon you. Too often the easier-looking path wins only because of a lack of vision or courage.

Mentorship

I will take the right person over a good business idea any day. It’s the business of people, all day, every day. Pick teams schoolyard style: you can have all the good ideas. I’ll take the people who want to be there and want to work to become their best, because they find success wherever they are.

Value creation as a way of being. Create value and money follows. Where can you serve? How can you be valuable? If all you want is money, you’ll always be chasing it.

How do you draw high-quality people and outcomes into your life? What attribute or practice has drawn people to you?

• Role models: authors and heroes you learn from at a distance.
• Mentors: people above you whose wisdom you want. Don’t try to act like their peer. Don’t muddy the water.
• Tribe: friends who are in the trenches with you.

A good mentor / mentee relationship

Don’t wimp out. Actually do the things your mentor recommends. The people who are serious put in the work.

Ask a question that will result in a task.

Workbook activities

• Complete the role identity collapse exercise.
• Keep a business journal (below).

Journal: Business journal

• How many sales pitches did you attempt?
• What was your approach?
• What was your success rate?
• What did your successes have in common? Warm leads, a specific pitch, the same age, neighborhood?
• What will you refine based on the data?
• Will you keep going with this business, or take what you learned and try a new one?