Three Whiskeys with an Entrepreneur

Buy me a drink and I’ll tell you everything I know.

Whenever a would-be entrepreneur asks me for advice, that’s my answer. When the ones that are serious take me up on it, it goes something like this.

We sit down somewhere with a pretty bar. I like pretty bars. You know, the kind where all the bottles are backlit? Then we ask the bartender to pour us some bourbon. This is not a beer and wine conversation. Whiskey is required.

Okay, I begin. Let’s talk vision. That word gets thrown around a lot but it really is the foundation. So we have to start there. Let’s push past business school theory and talk about what really matters when it comes to vision. 

A Vision Worthy of Sacrifice

You need a clear vision that is worthy of sacrifice. Because sacrifice is required. You will very likely will lose a shit-ton of money in the early years, whether it’s a direct loss as you live off your savings or the opportunity cost of making less than you could make working for an established company.

The would-be entrepreneur makes a nervous joke. I continue.

Be prepared to lose money before you make money and probably more than you anticipated. Is what you’re building going to be worth it? You will sacrifice time, too. Because you will work harder at this thing than anything you’ve ever done in your life. And understand it’s not just you who sacrifices. You’ll ask everyone around you to sacrifice. Family, friends, and most of all, your business partners and those first employees that are brave enough to join you on this mad expedition into the unknown. Their willingness to sacrifice will be defined by your ability to inspire. Which brings us back to the vision.

The would-be looks scared now. That’s good. Fear is a sign of intelligence.

Above all, your vision has to be super fucking clear. So clear you can repeat it again and again and again for the rest of your life without a script or a slide. So clear the dumbest person who ever sits in your conference room will totally get it. So clear you can hire and fire to it and still live with yourself. So clear that you know when to say “No” to opportunities that could dilute or sidetrack. So clear you’ll know the difference between a smart pivot and surrender. And let’s not get hung up on the distinction between a vision, a mission, or whatever Simon Sinek calls it in his latest TED Talk. Some will split hairs and tell you those are all different things. But we don’t have the patience for a 30-page deck. We’re entrepreneurs. Our story has to be visceral. Why are you building something new and what will it look like when the dream is realized? That’s your vision. It has to be clear and it has to be worthy of all that will be required to see it done.

Our glasses are empty. The bartender asks and I answer with a gesture. Two more.

Okay, what’s next? Talent.

Build a Talent Development Culture

Whatever you do, build a culture that is centered around talent development. It’s your only chance of competing, really. To use a sports metaphor, you’re not the school that’s going to get a ton of 4-star and 5-star recruits. You’re the school that’s going to get mostly 3-star recruits and you will have to coach them up and turn them into killers who can beat up the 5-stars and take their lunch money. If you can’t do this, you will fail. And if you can’t build a culture full of leaders who do this, you will not scale. 

It starts with how you hire. Most people are too focused on qualifications. Qualifications define a candidate’s floor but ambition is what defines their ceiling. Hire ambitious people.  I will always take a moderately qualified person who’s burning with ambition over a super qualified person who’s happy coasting. Give me a few months with the ambitious person and they will run circles around the coaster.  Ambitious people respond to a coach who cares about their development. They crave high standards and gnarly challenges. Give them both. Put them in situations that scare them a little and then be there to coach them through it. Do not lower the standard. The standard is the standard.

Build a culture where all the leaders care more about their people’s careers than they do their own and watch it snowball. This is how challengers compete and win. 

The bartender asks if we want one more. Yeah, okay. One more.

Alright, what else can I tell you?

Choose Partners Who Share Your Values

Leadership is lonely. Ownership is lonelier still.

The journey is much better with partners. The ideal partner is someone who has very different strengths than yours but shares similar values. Shared values are the most important thing. The hardest issues you’ll face aren’t the dry business issues, it’s the messy human issues. Dealing with real live human beings is hard stuff, whether they are employees, clients or vendors. Clients are just as messed up as anyone but the power dynamic with that relationship makes it especially challenging. How do you know which battles to pick? Values. How you manage your relationship with vendors feels safer in comparison but there are consequences there, too. How you handle vendors can either strengthen your company’s reputation or ruin it. Most important are the humans who walk your halls every day and managing them will test your values. Employees do weird, unexpected things that force you to have weird, unexpected conversations. You will have to talk with your partners about hard things, sometimes under great pressure. No two humans see the world exactly the same but the more aligned your core values are, the easier these conversations will be and the more confident you’ll be in the decisions you make.

Choose partners with great character and grit. Choose partners who you sincerely admire for their talents and accomplishments. Choose partners who have good judgment and are good communicators. Choose partners you trust with your livelihood, if not your life. If you pick the right ones, you will develop an incredible bond. There is an intellectual intimacy that is hard to explain until you’ve experienced it. Those relationships, in many ways, are their own reward and can sustain you on days when your tank is running empty. Choosing your partners is probably the most important decision you will make. So get it right.

I ask for the check. We call a couple UBERs. Time to wrap up.

Okay, that’s enough. Three whiskeys is plenty and if we keep going you won’t remember the rest of what I say anyway. Good luck. Reach out after you’ve been running your business a couple years and we’ll have three more. Maybe you’ll have some advice for me. I would love that because – and here’s a bonus lesson on our way out the door – successful entrepreneurs never stop learning.