The hardest question I’ve ever asked a founder

Recently, I spoke with a founder who had quietly bootstrapped a business to $10M+ in profit. He'd been at it for almost a decade.

The business had recently experienced some growth volatility, and he seemed… tired.

We were talking about the process of selling, "post-exit" life and a variety of such topics. Finally, I posed a question to him:

"Well, what do YOU want?"

He started giving me an answer, “Well, I think we need to show another quarter of growth above 20%, then enter this new business line and then we can sell.”

I half-interrupted him, “I get all that, but what do YOU want?"

He paused. Startled. And the call went silent. Finally, he said, "I have never asked myself that question."

He is not alone. Almost every entrepreneur (or frankly, person), I speak with does not ask themself that question. 

And even those who do (including myself), have a REALLY hard time answering it.

Before we explore, pause for a second: Do you know what you want? What would make you happy? 

If so, send it to me! Try to be as detailed as possible and explain why that is the answer.

Let's dive deep into the "anti-patterns," and then I'll offer some tactics for figuring it out.

The most common trap myself and other entrepreneurs fall into: Rather than answering what they want… they answer what they think is RIGHT.

Rightness is sort of like "society’s" answer to the question of what you think you should do. Read that again.

This one shows up when you ask an entrepreneur what they want for their business, and they jump into their strategy, how they grow the business and they start talking about how they will be huge (or raise lots of rounds.)

But I've also seen it show up when friends are deciding what city to live in, whether to send kids to public or private school or any type of decision. 

We are taught to make pro and con lists, evaluate and choose the right option.

But here's a radical view: For life's most important decisions, there IS NO right answer.

Another trap I've fallen into. We don't believe it’s POSSIBLE to have what we want, so we choose something more "feasible."

This shows up in big and small ways.

The most common small way is just reflecting on your day-to-day schedule and asking about a few things you could start or stop doing that would improve your day. 

When Andrew was joining Bootstrapped Giants, we encouraged him to take Fridays off.

Often, he looked confused, "I can't do it…". We said, “Sure you can!” Once he considered it, he realized it WAS possible with appropriate planning and management. 

Most of us get stuck in our day-to-days, we are creatures of habit and we do things that are "7/10" because we just don't believe it can be better.

The big ways are more obvious: For me, at times I think I've chosen bootstrapping and certain businesses that were "sure things" because I was afraid to fail or just didn't believe I could build the big thing. 

That's a limiting belief in action.

This sort of rhymes with number 1 but can feel more emotional/charged.

It’s not about the right answer, but it’s about something we believe we want, when in fact it comes from parental or societal conditioning.

The classic founder one is… "I’ll be happy when I sell my company for tens of millions and have freedom.”

I have heard that lie, told myself it and met hundreds of founders who have done the same.

It has been true for them in ZERO cases.

It can be small, too. You might want to live in the city when you really like the suburbs. You might say you want kids when you actually don't. 

This is a tough one because it really takes courage to pause and ask yourself: Am I being honest with myself?

So, we have the anti-patterns…

For a deeper dive on this, I just recorded a podcast on it.

When my wife and I were deciding whether to stay in San Francisco, move to San Diego (where we both have family) or move to St. Louis (where we grew up but no longer have family), Dave gave us a simple exercise. 

Write down the names of each city and stand on them, then see how you feel.

Which one makes you feel most ALIVE? (The answer was St. Louis.) 

Aliveness is a mix of excitement, energy and knowing. It’s not a mind/thinking exercise. 

You know it when you feel it, and so if you don't, you probably don't WANT whatever is on the other side.

This was my first suggestion to this founder. He has a company worth $100M+, distributes cash flow to himself, but seems so burnt out. 

I said this will be much more valuable than an investment banker. Because a coach is a mirror — they help you by reflecting back your words, thought patterns and common problems.

A coach essentially stands for what you truly want and will reflect back to you when it seems like you're doing an anti-pattern.

One of my favorite learnings from Dave is just asking, "What would make it a 10/10?"

That question forces me out of my settling for less and pushes me to think about what I truly want.

Trite, I know, I know. But I have a very specific set of questions I use here (for myself and others).

Let's say you're deciding between building an ecommerce business selling desks and an AI agency. 

My first question is, "If you were assured success in five years in either option, which would you choose?"

Most people have a quick answer.

Then, the harder one, "If you were assured FAILURE in five years regardless of which you chose, what's your pick?"

This question set forces the person to simply consider: “How do I want to spend my next five years?”

There you have it — Jesse’s guide to knowing what you WANT.

As the call ended with this entrepreneur, we finally got to what he wanted: "I want to be done, but I'm scared to admit it." 

He took my advice on hiring a coach and texted me: "I'm hiring investment bankers. We are selling this puppy!"

Have a great week!

jesse