Entrepreneurship Ruined My Life

And it was the best thing that ever happened to me!

Grant G. Leonard
6 min readFeb 20, 2021


A very candid shot taken on the set of The GLG’s commercial shoot

See that guy in the banner image? That is who I like to call “GLG Grant,” aka me in the height of building The Grant Leonard Group. This picture was taken in June 2018, just over 3 years after starting my company at the age of 22. What was initially just a grand experiment to differentiate my early career resume bullets (almost accidentally) morphed into an all-consuming lust for “the grind” that eventually lead to a massive burnout followed by an intentional sabbatical that culminated into my first major “pivot.” I put “pivot” in air quotes because it was not only a professional pivot, but a personal — dare I say spiritual — pivot that culminated in a refreshed perspective and enlightened lifestyle. The poise, balance, and patience I now operate with would not be possible without my entrepreneurial bull ride, and while I never expected for things to transpire the way they have, I could not be more grateful for the lessons learned from building my company in my early 20s. Without these, I would not feel as grounded, as confident, and as resourceful as I do now; and it is for this reason, I candidly say entrepreneurship ruined my life in the best way possible. Here are the main takeaways:

Entrepreneurship is like choosing the “red pill” in the Matrix

My mentor who helped me start my company even described it as such; wow, was he spot on! In his Matrix-style analogy, he presented the “red pill” as the pill of choice, of autonomy, of creativity, of courage, and of adventure. Taking the red pill meant that I would build things how I wanted to build them, with whom I wanted to build them, where I wanted to build them, and why I wanted to build them. It was the freedom to operate self-sufficiently and to not have to wait for someone else’s permission to live life on my terms. The “blue pill” in his analogy was learning that this self-driven livelihood was not only possible, but plausible, and still choosing a life of reactivity and compliance — or, candidly, a life in Corporate America. In choosing the red pill, I became a 20-something business owner sitting at the same tables as business owners 3 times my age, or venture capitalists with 300x my wealth. Eavesdrop on your typical corporate hierarchy…