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CanvasRebel: Meet Garrett McClure - Investor, advisor, and CEO with a passion for helping entrepreneurs.



One of the biggest mistakes I’ve ever made in life has been to blindly chase after success (or fame, fortune, money, achievements, etc). In life, anytime you want to know how to achieve something, such as “success”, you first need to know deeply what you are trying to get.


To be successful in life, you need to start with the end in mind and define what success is for in business, health, love, family, and your life overall.


And I mean to go deep and create a story, a vision, of what that looks, smells, feels, acts, and tastes like. What are you doing? Where are you living? Who’s around you? What’s your morning like? How’s the air smell? Get specific!!


My definition of success is flexible and ebbs and flows over time depending on life circumstances, needs, and desires. But one measure of success that is paramount is the answer to this simple question, “Am I happy?”


Happiness, for me, comes from many factors such as financial security, a healthy body, a curious mind, having deep friendships, engaging projects, and committing to audacious goals in business and physically.




I’m an investor, advisor, and CEO with a passion for helping fellow entrepreneurs achieve their goals and do good in the world. Probably not surprisingly, it’s been a winding, surprising road to this place in my career. After almost 20 years in digital media and advertising, including roles at Yahoo! and Basis, working with 100s of agencies, publishers, platforms, and 1,000s of ad executives, media execs, and advertisers, I have transitioned into the exciting role of Investor.


Today, I partner with agency owners as we acquire, merge, and grow businesses. This strategy helps legacy owners realize their greatest dreams in an exit – growing faster and bigger than they could alone.


Through a merger or acquisition, we can solve most business challenges faster with greater outcomes and shave 2-5 years or more off the process. But all this requires high levels of trust, strong communication, and some risk-taking.


The COVID-19 pandemic is a major pivot point (also known as a major life crisis) that might be a lesson your readers could benefit from. The few years before the 2020 shutdown, I had left the digital advertising world and pursued several more entrepreneurial pursuits. I worked briefly in a role as the Corp Relations Manager at the world’s largest LGBT non-profit, helped found an HR-Tech start-up, and had 3 advisory clients. I was having fun, doing lots of different things – but was seeking a new adventure to completely throw myself into.



My pivot from CEO into advising and investing is creating a future where I can make this a reality. Getting back to the earlier section on success – this is one of the big projects that brings me incredible pride and happiness – even when it’s still in the planning and vision stages.


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