ARE YOU UPLEVABLE?
Scale Or Fail?
Below are some of the most salient questions that I use when working with entrepreneurs and analyzing businesses. Individually taken, each question poses an entirely new series of questions behind it.
Taking the time to contemplate both the question and your answer will bring insights and strategies that will help you avoid failures and capture some serious wins. Have fun going down the rabbit hole.
1) WHICH STAGE OF GROWTH IS YOUR BUSINESS IN?
Every successful business transitions through three distinct stages of growth. Pinpointing your company's current phase helps you clarify immediate priorities and strategic next steps. It's not uncommon to be half in one stage and half in the other.
Which stage of growth do you think you’re primarily in?
1. The Pioneering Stage (Start-Up)
Focus: Passion, ideas, and purpose.
Driver: Fueled by the entrepreneur's vision to bring a new concept to market.
2. The Established Stage (Growth & Stabilization)
Focus: Balance, momentum, and operational efficiency.
Driver: Building predictable profitability and implementing structured systems.
3. The Mature Stage (Success & Transformation)
Focus: Stability, market leadership, and evolution.
Driver: Maximizing profitability while deciding the next chapter—whether navigating an acquisition or reinventing the company with a fresh pivot to spark new inspiration.
2) WHAT TYPE OF ENTREPRENEUR ARE YOU?
Every business owner operates with complete freedom, carving out a unique path—which is precisely why many choose entrepreneurship in the first place. Naturally, no two founders are identical. While some possess exceptional mastery over a few specialized skills, others excel as versatile generalists, and many truly hit their stride years into their careers.
The Artist (The Visionary)
Driven by innovation and a rebellious spirit, Artists defy conventional limits to pioneer new products and services. They possess an extraordinary capacity for creative risk and are constantly inspired by new ideas, though keeping them focused can be a challenge.
The Engineer (The Operator)
Engineers ground abstract ideas into functional reality. They design the systems, enforce predictability, and maximize efficiency to ensure flawless execution. Risk-averse and highly disciplined, they prioritize consistency over novelty.
The General (The Executive)
Generals excel at leadership, organizational culture, and strategic alignment. With exceptional emotional intelligence, they synchronize team dynamics and cultivate trust across the organization, fully accepting final accountability for all corporate outcomes.
3) THE 3 "R"s IN ENTREPRENEURSHIP
Forget the boring 50-page business plans—building a company is a full-contact sumo wrestling matching that requires a completely different kind of survival dress-code. To make it out alive, you need to master the 3 R's of entrepreneurship.
Respect
When you give respect you get respect. Business is about walking through open doors and rarely do know-it-alls get party invites.
Resilience
Back in the late 90's one of my very first mentors told me that the difference between someone who is successful and someone who isn't is whether or not they get back up after getting punched in the stomach. Learn how to get back up.
Resourcefulness
The most important resource is resourcefulness. When you master "Solution Based Thinking" you'll know you've arrived.
4) WHAT IS ENOUGH? (no wrong answers)
Choosing the ultimate scale of your company starts with a brutal reality check about how you want your actual Mondays to look. You must weigh the thrill of a massive enterprise against the heavy burdens of complex management, finding the sweet spot where your goals match your definition of freedom. Ultimately, the perfect business size is the one that fuels your financial goals without consuming your peace of mind.
Not sure yet - lets see what unfolds
Your curious. You are a born learner. You have a hunch and a level of control and self awareness to keep you out of bankruptcy and more importantly from being eaten by sharks.
Hey I'd like a little success
I just want to be able to shop at Whole Foods regularly, take a trip or 2 a year with my family and afford a house cleaner every 2 weeks.
$4 Trillion Dollar IPO! LETS GO!!!
Playlist blasting, hyper caffeinated, all gassed up and ready to ride it till the wheels fall off.