Last week, I stared at my best friend since 7th grade pre-algebra. She shifted in her seat, a little uncomfortable.

I stared and said: “So, what do YOU want for your life?”

Her response: “I don’t even know where to begin with that question.”

That led to this email and nailing one of the most important questions facing every entrepreneur.

Here is the backstory:

Adriane (my BFF) and I started GrowthAssistant 3 years ago this month. It took off faster than either of us expected.

In a past email I told you how, instead of hunting for product market fit, we hunted for real sales, fast.

Once we made a few sales, I tweeted our sales numbers and shared how we helped clients hire assistants for their marketing work.

And that got us even more clients. So we kept growing, Tweeting, sharing, and growing again.

That can become an unfulfilling hamster wheel if you don't stop to ask yourself, "Where is this all going?"

In this case, this deep existential question started with… TAXES.

Yes, besides death, the only other certainty of life.

When we originally started GrowthAssistant, we thought it would be a smaller “cash flow” business, so we made it a pass-through LLC (meaning we don’t pay corporate taxes, just personal taxes on the income we receive).

But as it has grown, it’s clear that it has real enterprise value. We’ve even received unsolicited buyout offers that would make it so Adriane never has to work again!

Our tax advisor shared: “Well if you plan to sell, you should consider converting to a C-corp. Because with QSBS, after 5 years you could sell and pay essentially NO taxes on the sale.”

Your situation is undoubtedly different from Adriane's but you should do this exercise too, if you want to build a business and life that energizes you.

Here is the exercise I suggested she do:

It’s funny: most people say they want to be entrepreneurs because they “want freedom” and “want to work for themselves.”

What most quickly realize is: that a JOB is WAY more free than owning a business.

You can leave a job anytime you want. You can not worry about all the other stuff happening in the company and just “do your job.”

A business owner does not have this luxury.

So most of us quickly realize that entrepreneurship is usually WAY more consuming than a job. And if you just let company-building take over, there is NO light at the end of the tunnel.

There are always more customers to grow/optimize, more employees to hire and train, and more offsites to be planned.

It’s never-ending and, especially in the early days, every job that doesn't have an “owner” goes to the CEO/Founders.

What I suggested to Adriane was to do a “personal DFS, Desired Future State.”

It's a more specific, detailed version of a vision. Her first instinct was to focus on “what was right for the business” in terms of selling/running it.

But I quickly reminded her that that is an important question, but totally separate from what is best for her.
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For a couple of reasons:
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​1) She IS NOT the business, even though she created it. It could exist without her and vice versa. So conflating them isn’t “real,” it's a story entrepreneurs tell themselves (I know from experience). And...
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​2) Because as long as she is running the business, it will be highly dependent on her. SO where/how she wants to spend her time is a more foundational question than what's right for the business. If they are the same, great, if they are not the same, that's also great. But creating clarity there is super valuable.

So what does a Personal DFS look like? Well, it can be anything that matters to you. Some topics I’d suggest:

• Family life, how much time do you want to spend there? How involved?
• Working, what type of work do you want to do? How many hours a week?
• Financial, how much money do you want? Income? Assets
• Purpose, what lights you up? What do you want to change in the world?
• Health, how do you want to eat? Exercise? Meditate, etc?

Essentially think about the exact, 10/10 life you want for yourself across all dimensions.

Beyond these categories, one of my favorite versions of this is:

Remove all constraints and just create that perfect day. And perfect week.

Once you have it written down. Then you can start to look at the “current reality” of where you stand today.

Initially, almost everyone finds TONS of low-hanging fruit. I.e. things they can change quickly/easily to better align with their true wants.

But then, some longer-dated or tougher things come up that need to be addressed.

In Adriane's case, for example, she can’t “truly” be a CEO until she hires a handful of executives, so no teams are reporting to her.

She also wants to get clearer on where she wants her time going in the biz and where she wants to partner with experienced executives.

One of the most important parts of this exercise: nailing your purpose.

Most people want to do some kind of productive work (as appealing as it may seem to sit on a beach all day) and in my experience, when they know what that is: work stops feeling like work.

It's fun and exciting and a BIG part of a fulfilled life. It MAY be the ultimate answer for every founder/ceo: Should I sell or keep running this business

You all saw my schedule in a previous email. That wasn’t an accident, it was a function of this exercise.

Beyond wanting to see my kids a lot, working a certain number of hours, having a certain financial safety net, exercising, and maintaining weight at 180 lbs…I had a very specific purpose.

I love building businesses and coaching CEOs. I DO NOT want to be the CEO of an early-stage company, but I love supporting them while co-creating something.

And in that process, uplift others and help them learn and grow. This exercise helped me realize all that.

That’s what led me to start Gateway X. Most days I ran Ampush, I felt pretty beat up and wasn’t sure what I wanted or how long I could go. GX feels very different.

If I get to start a new business with an awesome CEO every year who wants my coaching… I think I could do this until I DIE!

When I was at Ampush, I didn’t think that type of conviction was possible, but now I do.

It has required me to be clear about what I want and don’t want, dial in my purpose, and stay inside my Zones of Genius.

Is it perfect? Hell no, but it's a huge change from 5 years ago.

To Recap:

• Knowing what you want is HARD
• Do your personal DFS
• Once you’re clear on that, figure out what has to change
• Pay attention to your purpose and Genius
• Thrive

Feel free to hit reply and send me your DFS if you do this and I’m happy to give feedback!

jesse