Hollies Winston

5 Things I've Learned: Hollies Winston

Friday, April 8, 2022

Hollies Winston

Hollies Winston

Hollies Winston, ’13 MBA, is owner of Guaranteed America, LLC, (GA), a firm he founded in 2017. GA offers full services to clients in the arenas of advocacy/government affairs, coalition building, and strategy.

Winston also sits on the MN Council of African Heritage, which advises the governor and Legislature on policies that affect communities of African descent. He is married to his wife of 18 years, Latrice, and has three children.


1. Make your choice, lose the guilt.

After graduating from the Carlson School in 2013, I took a job with a company that was at the time in the Fortune 15. I was miserable after a year. At this time, I also rediscovered my passion for community. I’d often balance dedicating time to my passion with a job that paid the bills, knowing that if I spent more time at that job I’d be promoted quickly. I felt a tremendous amount of guilt as I pursued this path. In 2017 I cut ties, started Guaranteed America LLC, and was off to the races. Had I ignored my passion, I’d still be in that environment and far less successful and fulfilled. The choices made were necessary, the guilt was not.

2. Relationships matter.

We’re often told growing up to be the hardest-working, smartest person in the room. The reality is, those are just some of the factors. Building relationships with folks who trust your character and your work product gives you access to business opportunities and expertise others won’t have access to. Invest in relationships just as much as you invest in your job skills to increase your mid-term and long-term prospects.

3. Be humble with pride.

Being humble wasn’t always a strength. Over time (life humbles you), I learned its value. By being humble, you don’t have the baggage of embarrassment if you overlook minor details and you’ll find people will willingly share key information with you. Since people will want to trust you, it makes it easier to maintain key relationships of trust. Still, you must conduct business with a pride that encourages people to believe in the quality of your product, your service and your character.

4. Stay grounded.

The rat race of life can be stressful. There’s pressure to win and to earn more money and recognition than your coworkers or competing businesses. Taken to its extreme, this encourages focus on the things that matter least. Take time to be thankful for key family and friends and your health. This grounds you in the present, but prepares you for the future. No matter how big your house is, or your retirement, it means little if your family and friends aren’t there to enjoy life with you over a meal.

“Looking at a setback as a temporary adversity to overcome, that you must overcome, is a paradigm that sets you up to achieve eventual greatness.”

– Hollies Winston, '13 MBA

5. Let your adversity define you.

I’m aware this may sound similar to saying let your failures define you. There’s a key difference, failure is finite. It’s complete. Looking at a setback as a temporary adversity to overcome, that you must overcome, is
a paradigm that sets you up to achieve eventual greatness. It creates the same bulldog tenacity seen in the likes of a Michael Jordan, a Martin Luther King Jr., or even a Joe Biden—who finally achieved his goal of being president after more than 30 years. This lesson has served me well in my career.

Spring 2022 alumni magazine cover

This article appeared in the Spring 2022 alumni magazine

Strength is determined by how we rise in the face of challenges. 

The Carlson School community remains an unstoppable force. 

Spring 2022 table of contents