An Orphan, A Single-Wide and A Compass: My Life In Symbols

A lot of founders and entrepreneurs see investors as an insider group – elite, card-carrying members of a secret financial world. And the ingenuity and creativity that inspires founders to start their own businesses are qualities that can make them feel like outsiders in that so-called secret business world. Oftentimes, entrepreneurs come from nontraditional, educational, or professional backgrounds and they see that as a bad thing, a reason they won’t be taken seriously in the business world.

But I see it as a good thing. That rebel nature, that quirky past – it sets you apart from the pack. It got you where you are today. It’s what created your endless drive and work ethic and it makes you so much more interesting – from a business perspective and a human one.

I say that with certainty, because I wasn’t born into wealth or power and I wasn’t a legacy graduate from an Ivy league school. I was an orphan. And I was raised in a trailer park by a mother with a sixth grade education and a father who was an auto mechanic. My parents didn’t insist on great grades; instead they fostered my innate curiosity and fascination with learning about things that appealed to me. And as a result, I threw myself into anything that caught my interest – weightlifting, sports, music – especially Iron Maiden.  I learned from all kinds of people in the process which has turned out to be so much more valuable in business and in life. Here’s why…

3 Ways Being An Outsider Makes Me A Better Investor.

1. I learned to trust my gut.
   Early on, it’s tempting to follow the advice of anyone who has more experience than you. But over time, I started to hear a voice in my head and, after a few times of seeing something coming and ignoring that voice, I learned to trust it.
   
   And trusting my instinct has made me less afraid to fail. My first company failed, my second succeeded and, even though I got fired, I still ended up with a $150mm exit. I exited my third company, myMatrixx, for $250mm. After over $400mm in exits, I have learned from each of the risks I have taken and have developed the ability to follow my instinct. I do what’s right for me even when others don’t get it – especially when others don’t get it.
   
   Which is why I use the symbol of a compass in my work; it’s a symbol of clear direction and that little bit of risk and faith that you’ll get where you’re going if you just follow your course.
   
   
2.  I learned how to build a community.
   When you’re not born into a powerful world, you have to build your own community the hard way. But guess what? It’s so much more fulfilling. When you’re surrounded by people of diverse backgrounds and experience and you’re open to hearing what they have to say and looking at things in a different way, you’ll learn so much more than you could learn in a business school classroom.
   
   One of the most effective pieces of advice I give founders is to ask potential investors for advice, not money. You’ll find you may get both and, even if you just get advice, you’ll find it pays back in dividends.
   
   
3.  I learned to appreciate a rebel spirit in myself – and in others.
   For all my talk about rebellion, you might be surprised to learn that I joined the Air National Guard to pay for college – and that I flourished there. My commanding officers saw “something” in me and put me in leadership positions. Granted my nickname was “mean old red rope” so I clearly had some communication skills to work on, but those experiences prepared me for future positions of leadership in the business world. They lit a fire inside of me. They gave me the confidence to see myself as an entrepreneur. I’ll always remember the feeling of being seen that way and it’s made me more conscious of looking for, and fostering, that spark in others.
   
   Funny story: the rebel in me refused to cut my long hair so on my “one weekend a month” I stuffed it in a short-hair wig ala Tattoo from “Fantasy Island”. It definitely freaked a few people out…

Part of my job is to help others define their unique path.
Mentorship is a big part of what I do and what draws me to Angel Investing. I launched MacDonald Ventures with the goal of providing mentorship along with my investment, combining my experience with the next generations’ innovations. Helping founders learn to follow their own unique path and develop the technology that will change our world is how I hope to contribute to the future of tech.

Do you have a maverick spirit and a startup that you believe in? I want to fund a select group of phenomenons. Follow our new page on LinkedIn to learn more about us or to direct message my team.