A Letter to Frustrated Founders (and the people surviving them)

10 min read
Sep 27, 2023 12:00:00 AM

Letter to a Frustrated Founder (and the people surviving them)

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The ideas explored in this article give you a glimpse at my upcoming book, Renegades: Break Rules, Find Freedom (A Book for Founders).

Sign up here to get on the launch list and access a free chapter.


Dear fellow founder,

I hate to be the one to break it to you. 

None of us escape the moment when what works for five or ten years to grow the business just doesn’t work anymore. Your grit, decisiveness, rule-breaking and bending, your ability to find new opportunities and chase them down all become liabilities to the future of the business instead of the way things get done. 

Instead of being the hero, you end up feeling like the villain—your team doesn’t respond to your visionary leadership like they used to, your customers are confused or disengaged, and stakeholders are looking at you for an answer. And the truth is (at least for me) I didn’t want to have to answer to anybody. I just wanted to keep exercising the freedom to run my business like I’d set out to from the beginning. If I gave into what everyone else wanted, I felt like I’d lose that freedom.

Maybe you’re feeling that pain now, or you will in the not-too-distant future as your business reaches new phases of growth.

I get it. It feels like we’re staring into a mirror where our strengths and weaknesses are reflected back as one and the same. The very factors and characteristics that got us here are the same ones preventing future progress.

I’m writing you this letter because I think this is a problem few people understand unless they’re in our shoes and I want you to know you’re not alone. Either by luck, determination, or insanity, I’ve gone through this challenge as a founder 10 times now. I know the journey you’re on extremely well. 

Lucky for you, each time I’ve encountered this battle, I gained some insights—from success and failure alike—that I think can save you some time and heartache. I can help us move forward with a better plan than giving into the business and losing yourself as a “Renegade” Visionary or continuing to face the resistance you’re likely feeling all around you.

I know you’re short on time. Everybody still needs you. You’re the center of your business universe. So I’ve outlined a list for you of the things I learned to take a business to scale, re-engage your strengths, AND allow you to re-discover your entrepreneurial freedom.

Bottom line: You don’t have to trade anything about who you truly are. You don’t have to give up your entrepreneurial spirit for rules and systems. 

You have the opportunity to lead through your strengths and shift your focus to leading your people. Freedom like you’ve never known is on the other side.

These are the key three things I learned that changed everything I ever thought about how to run and lead my businesses. They’re counterintuitive to what most people have told you throughout your entire life. But that’s how we roll as Renegades, right? Break the rules, find more freedom.


3 Counterintuitive Ideas No One is Going to Tell You About Your Business 

  1. It’s not you, it’s you.

  2. It takes an army to be a founder.

  3. Don’t run the business.


1. It’s not you. It’s you. 

For the longest time, I believed…

If I wanted to see my vision come true for the business, it was all on me—my focus, my time, and my life had to get extremely dialed in to accommodate all that it required of me. And that worked for a while. The business grew, BUT I felt like my sandbox to innovate, create, and change course got smaller and smaller.

What I learned was…

That the more freedom I created for myself, the better the business could succeed. I learned that I was not my business and the business was not ME. I had to take the part of my identity that attached itself to the performance of the business over the years and rediscover my value outside of what the business could accomplish.

The first step in this counterintuitive approach is rethinking your role in your organization. This might be the hardest shift in thinking that you have to make because the idea of “doing less” seems to equal “being less.” Less aware, less involved, less influential, less present. We get addicted to being “needed”. Being needed gets twisted into being valuable. So too many great founders stay at the center of their universe because they’re afraid their value won’t exist outside of it.

Here’s why that’s wrong. 

  1. If you or your identity are at the center of the business, it’s always at risk to react to emotion and circumstance.

  2. If you’re doing all the things, you’re not doing the best things.

A great mentor and friend of mine, John Richie says, “The root of all business issues flow from the heart of the leader.”

The counterintuitive step I had to take was to begin to separate WHO I was (my identity) from WHAT I DID for my organization. The clearer those boundaries were for me and my people, the more stable the business became and the more free I became.

Check out this free assessment to evaluate your own leadership effectiveness. Have you truly separated who you are from what you do? Let’s find out.


2. It takes an army to be a founder

The other thing I got wrong was how I built the team around me. 

It’s simple: We hire people to do a job and carry a portion of the workload, right? Because as a founder, hiring people for the first several years is about helping us keep our heads above water and do things we don't know how to do very well. It’s about getting more work done as demand increases. The goal is straight-up survival.

Founders are usually master generalists. They know a little about a lot. So we hire people to help us carry the ball, send them off with general expectations, and leave them to figure out the small stuff.

The only problem with this approach is whether you’re a team of 3, 30, or 300, you’ve designed your business with YOU at the center. I doubt you did this consciously. You’d likely prefer it if every question and decision didn’t come your way. This happens because it’s easy to start this way, but it’s hard to break out of this design when it no longer works at scale.

I tend to forget how strong my gravitational pull can be on my business. This is problematic when I want to skyrocket toward an opportunity and I yank the entire orbital system of my business from its atmosphere to come along for the ride. 

If this continued to be the case, then as the business got more complex, I would be standing at the center of everything causing massive disruption and spending all of my time trying to manage the mess.

That’s not what I wanted and it’s not what my team wanted either.

I had to learn how to structure my team so they could steadily make progress on the goals we set out to achieve. And I had to build support around me to ensure I stayed on track with what mattered most and continued to grow in my ability to lead.

The counterintuitive shift I had to make here was that I couldn’t hire people to simply do work anymore, not if I wanted to grow the business beyond my capacity. And more importantly, I could not keep “going it alone” and believe I’d eventually reach my destination on my intuition and ideas.

Here are the five key relationships I added to my army to keep my business in orbit and help me grow into the kind of leader I wanted to become:

  1. An Operator: to run the day-to-day and be my thinking partner

  2. An Admin: to make sure the right things get done

  3. A Leadership Team: to ensure execution and drive results

  4. A Coach: to help me be the version of myself I aspire to be

  5. A Peer Group: to expand my thinking and pressure test ideas


All in all, what I learned was…

A founder needs an army to do the job well. There’s no such thing as a successful founder who did it all on their own. I had to build the business WITH my people, my mentors, and my peers, not despite them. And I can tell you, doing the work of building a business with an army of people around you is a hell of a lot more fun than doing it alone.


3. Don’t run the business.

The last idea I had to accept was that the way I operated in the past was not going to take us to where we wanted to go in the future. There were things the business needed that I simply did not have the skills, capacity, or interest to pursue. 

In the early years as founders, we get used to being all things to all people and making every decision for the business. This works if our biggest aspiration for ourselves is to stay enslaved to the business, and only grow it as big as our individual capacity.

If I wanted something different for my life as an entrepreneur and for the future of my business, I had to face the fact that I did not need to run the business.

  • I was creating ambiguity where we needed clarity.

  • I assumed everyone understood the vision, mission, and goals but was not intentionally reinforcing those ideas.

  • There was no accountability, inconsistent communication, and a lot of confusion and inefficiency around the work being done day-by-day to get us to those goals.

  • Frankly, I did not want to be the person to try to manage it all even if we did figure it out.

I had to give the business the systems and “soul” it needed for it to grow beyond me.

There are six specific mental shifts I had to make that truly transformed how my business operated. I’ll give you what those six things were and one question or idea you can use to take the next best step.

  • I had to DESIGN my business with clear intentions. Ask everyone on your team to tell you the mission of their role. Do they know why they do what they do?

  • I had to create a CADENCE for our workflow. Set a weekly meeting with your team, set your agenda, and don’t skip it.

  • I had to set the SCORE so we could know if and when we were winning. Build a scoreboard with the top 5 most important metrics that demonstrate to the team when they are winning in the pursuit of your most important goals.

  • I had to communicate the DESTINATION. Can you answer WHY you want to grow, expand, and be the #1 company that does X in the next 5-10 years? Can your people?

  • I had to define our ETHOS. What matters to you about how you do the work you do and the identity you represent?

  • I had to build this WITH healthy, growing PEOPLE. Your business is built on the quality of your leadership and how you pass that leadership along to the team. Ask them to answer the questions above with you. Invite them into the conversation.



  1. It starts with YOU.

  2. It multiplies with THEM.

  3. It scales with a SYSTEM and a SOUL at the foundation.

I learned what I’m sharing with you over several decades of figuring it out, failing, and piecing together wisdom I’ve picked up along the way. It’s not the method that they teach you in business school. It’s not intuitive for entrepreneurs like us who are used to making our own way and shirking the system.

But, the results I’ve seen for myself and the founders I know are unreal.

I’ve seen nine-figure exits with businesses that were projected to run out of money in less than a year.

I’ve seen small agencies double their revenue.

I’ve seen family-run businesses build succession plans that allow the business to continue to grow from generation to generation.

Best of all, I’ve seen hundreds of founders and leaders like us rediscover their freedom to bring the best of themselves to their work and truly be able to trust the team they’ve empowered to run alongside them.

I see dignity for everyone on the other side of these shifts. 

Especially for you, fellow founder. There is dignity in rising to your highest and best use in your organization. There is dignity in being able to redefine yourself as a Renegade Leader.

In the journey with you,


These ideas and more are explored in my new book, Renegades: Break Rules, Find Freedom (A Book for Founders). Discover a counterintuitive approach to scale your business, re-engage your strengths, AND allow you to fully engage your entrepreneurial freedom.

Sign up here to get on the launch list and access a free chapter.

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