Alright – so today we’ve got the honor of introducing you to Stephen A. Hart. We think you’ll enjoy our conversation, we’ve shared it below.
Stephen A., thanks for joining us, excited to have you contributing your stories and insights. Can you talk to us about a project that’s meant a lot to you?
In my 20s, my sole pursuit was material. I wanted to be a millionaire by time I was 30. And I did become a millionaire at 30, but lost it all 3 months into being 31 … and 3 weeks after getting married. My business lost several million dollars in the summer of 2008.
The life lesson in that was that the money and material things will come and go, and while they’re great to have, we should never define our life and the legacy we live and leave by those things only.
In 2015, I was looking for a way for my then 5 year old daughter to see Black and Brown folks that looked and sounded like her doing dope things. In February 2016, I launched the Trailblazers.FM podcast, as a platform to showcase the success stories of accomplished Black leaders, entrepreneurs and creatives.
Trailblazers.FM is one of the most meaningful projects I’ve worked on. Over the past 7 years, I’ve interviewed over 250 guests, including Janice Bryant Howroyd (the first Black woman to build a billion dollar company in the United States), John Rogers Jr (Black man who founded the largest Black run mutual fund in the country), Dr Dennis Kimbro (author of several best selling books, including Think & Grow Rich, A Black Choice), and so many others.
Over the years, I’ve had countless listeners reach out from our now 400k plus downloads in 150+ countries around the world. Many have shared how the stories, wisdom, and the resources/tools shared have helped them to blaze their own trails.
One such story that pulls at my heart strings everytime, is what happened following an episode I did with Art Steele, ep 103, talking about Wills, Trusts and Estate Plans. After that episode, a listener who was married with kids, reached out to get help with finding a lawyer and securing the necessary plans for his family. In that moment, I realized that even if I hadn’t created another episode, that this one episode created real impact that would outlive me. If and when he and his wife pass, that he’d have positioned his generational wealth and assets to be passed along to his children. In a time and season where closing the racial wealth gap is such a big challenge, that episode mattered.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers
I was born in Kingston Jamaica, but came of age in the United States.
Being of Jamaican roots, I’ve got a ton of hustle and jobs lol.
By day, I’m a marketing leader for the SANS Institute, the largest provider of cybersecurity training, research and certification globally. As the Head of Content Marketing, I help to lead our strategic approach to creating and distributing unique, valuable, and relevant content consistently.
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Beyond the 9-5, I am also the founder of Isles Media, LLC, and host of the top rated Trailblazers.FM podcast.
For podcasting as shared on the prior page … in 2015, I was looking for a way for my then 5 year old daughter to see Black and Brown folks that looked and sounded like her doing dope things. In February 2016, I launched the Trailblazers.FM podcast, as a platform to showcase the success stories of accomplished Black leaders, entrepreneurs and creatives.
The problem: I was tired of seeing the lack of representation of successful Black people in all fields. Main stream media would present athletes, musicians, celebrities, but fail to share Black and Brown people being great in other occupations and industries.
Eventually, I was telling the stories of success of a few, but wanted our listeners to have better pathways and knowledge to blaze their own trails. Many of the people pitching me to come on the show, had little to no digital footprint. I’m a big believer that someone is Googling you, and the results they find will leave them either more or less inclined to do business with you, hire you, or even to date you.
Today, I offer consulting, community and courseware offerings. I have bootcamps on personal branding and building a podcast, and also offer a mastermind offering.
I’m most proud to be living out and leaving a legacy that will impact not only my children, but the future generations of Black leaders and entrepreneurs.
Can you share a story from your journey that illustrates your resilience?
In late December 2019 4-days before Christmas, after having published 205 consecutive weekly episodes on Trailblazers.FM, my dad suffered a stroke back in Kingston, Jamaica.
I was empty. I had nothing more to give. I paused the podcast for what I thought would be a few weeks, that turned into 8-months, having dealt with COVID, a freak injury to my wife, kids home, wife furloughed, and biggest of them all, having to wind up a 40-year old catering business for my dad in a third world country, in a pandemic.
Anxiety and depression overwhelmed me.
I got things going again in September 2020 for a series sponsored by P&G, but by January 2021, my dad suffered another stroke here in Maryland at my home. In the midst of his recovery, I knew I didn’t have the bandwidth to podcast but needed to create.
Instead of stopping, I pivoted.
I began to leverage live streaming on social media. I was determined I was going to be BAD til things got good. I’d wake up and do live streams in the mornings on LinkedIn several times a week.
Then in November 2021, the seemingly impossible happened, LinkedIn tapped me as a 1 of 100 creators to be part of the inaugural cohort of LinkedIn’s Creator Accelerator program. I was given a grant and a platform to continue creating on the platform.
I went on to create 50 live streams in 10-weeks under a test pilot program I called missionfuel.tv which will fuel the rebirth of Trailblazers.FM in February 2023.

For you, what’s the most rewarding aspect of being a creative?
The most rewarding aspect of being a creative is adding value and having an impact on my community.
As a podcaster, it’s amazing to see the reach of your content. There are people in countries I’ll never visit in my lifetime, who have consumed episodes of my show and will go on to impact their communities for generations to come. That is so inspiring.
Contact Info:
- Website: https://stephenahart.com
- Instagram: https://instagram.com/stephenahart
- Linkedin: https://linkedin.com/in/stephenaihart
- Twitter: https://twitter.com/stephenahart
- Other: My podcast website is https://iamblacksuccess.com

