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Success Story Podcast

Soledad O’Brien & Ian Freeman | Bridging the Equality Gap

By August 26, 2023September 25th, 2023No Comments

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About The Guest

Soledad O’Brien

Soledad O’Brien is a respected journalist and documentarian with a significant footprint across media channels. As the head of Soledad O’Brien Productions, she consistently delivers genuine stories on societal topics. Her experience extends through major networks such as CNN, MSNBC, and NBC, and her Emmy and Peabody awards highlight her dedication to journalism and documentary work, notably her series “Black in America.” Away from the camera, she helped establish the PowHERful Foundation to further young women’s education. O’Brien also actively engages as a speaker and author, making notable contributions to journalism, social causes, and educational discussions.

Ian Freeman

Ian Freeman, a Manhattan native, took a leap of faith in 1987. Starting with a $5,000 loan and a drive to make a difference, he ventured into the insurance realm after stints in banking and investment. Fast forward, and The Freeman Group in Boca Raton stands testament to his determination. Over the years, Ian’s endeavors have secured $1.8 billion in death benefits, impacting over 4,300 individuals and families. Today, from his home base in Deerfield Beach, FL, Ian remains steadfast in his commitment to leveling the playing field and fostering financial equality in communities.

Talking Points

  • 00:00 — Intro
  • 03:02 — Soledad O’Brien: Unveiling Her Journey
  • 05:56 — Ian Freeman: Forging His Path
  • 08:16 — Growth Mindsets: Key to Success
  • 18:34 — Ian Freeman: Evolving Perspectives
  • 21:58 — Embracing Failure: Lessons Learned
  • 29:56 — Empowering Underrepresented Voices
  • 42:24 — Sponsor: The Goal Digger Podcast
  • 43:09 — Diversity Teams: Power of Differences
  • 46:02 — Inclusion Struggles: Unseen Biases
  • 50:42 — Driving Change: Individual Roles
  • 59:12 — Expanding Financial Advice Access
  • 1:08:02 — D, E & I: Corporate Paradigm
  • 1:10:06 — Connect Online: Soledad & Ian
  • 1:12:24 — Wisdom for the Younger Self
  • 1:15:40 — Success Redefined: Insights from Soledad O’Brien and Ian Freeman

Show Links

Soledad O’Brien

Ian Freeman

Podcast & Newsletter Sponsors

Watch on YouTube

Show Summary: The Winding Roadmap to Lasting Success: Lessons on Passion, Purpose and Grit

What’s success?

If you asked me 10 years ago, I may have pointed to status and money. But the more leaders I speak with, the more I realize true success lies in purpose.

This truth comes through in my latest interviews with media icon Soledad O’Brien and financial advisor Ian Freeman. Their careers have taken wildly different trajectories yet led to the same insight: fulfillment comes from uplifting others.

See, Soledad and Ian didn’t compromise their values chasing clout. They put people first, even when it cost them. And they found that impact matters more than acclaim.

So how did two leaders from separate worlds reach the same conclusion?

That’s what I want to explore here. Below you’ll discover what fueled them, what they’ve learned, and how their wisdom can guide us, too.

From Newsroom to Impact Productions

If you’ve flipped on the TV in the last 20 years, chances are you’ve seen Soledad O’Brien. She’s brought nuanced reporting to CNN, NBC News, HBO and more.

But before Soledad commanded anchor chairs and shows bearing her name, her start in journalism was raw.

She recalled:

“In my very first live shot ever, I was literally groped on air,”.

Imagine that nightmare your first week on the job. Most would curl up and hide.

Not Soledad. She brushed off jerks and honed her craft, rising to become an Emmy-winning journalist praised for her rigorous yet empathic style.

So how did she power through those painful early days?

Purpose was her North Star…

See, Soledad never bought into the myth of objectivity. She knew stories affected real people, both as subjects and viewers.

And she believed everyone deserved to be seen in their full humanity, regardless of race, class or creed.

That’s why she pivoted from establishment newsrooms to start her own production company, Starfish Media Group.

There, Soledad could finally tell overlooked stories her way. And tackle topics like racial injustice with unflinching focus.

Like her work with “Black in America”, which explored the lives and challenges of African Americans in the United States, Soledad O’Brien shed light on the stories and struggles of the marginalized and oppressed.

Soledad gave voice to victims and connected the dots to our country’s long history of white nationalism.

This takes courage. To call out injustice you must first believe a better world is possible.

Soledad stays grounded in this vision. It’s why at her stage in her career, with enough acclaim to rest on her laurels, she still pushes for change.

Because she knows her privilege and platform come with a responsibility. To open eyes, create understanding, and help all belong.

Now let’s see how Ian Freeman cultivated this same purpose across a very different path.

From Wall Street to Main Street: Ian Freeman’s Journey

Ian Freeman stumbled into finance after college chasing a paycheck, not purpose.

But today he leads with conviction rare in money management. His mission? Bring financial access and literacy to underserved communities.

Because growing up, Ian saw the real-world impacts when families lack resources.

Ian reflected.

“Finance wasn’t part of my childhood because we didn’t have any… when you don’t understand it, you don’t have access.”

This drove Ian to bring change within and beyond his industry. Propelled by empathy spurred early on.

See, just two years into Ian’s finance career, he received a devastating call. A policyholder he had failed to advise adequately passed away.

Ian discovered gaps in the man’s coverage too late. His missteps meant the family was left stranded.

“I never did it again.”

Ian told me solemnly.

This nightmare birthed Ian’s purpose. He vowed to equip people neglected by traditional institutions. To serve with the care this moment demands.

That’s why Ian pushes his firm to reflect the community. And dedicates time to educating underrepresented groups on money management.

He also walks the talk of inclusion…

While some in finance talk diversity without action, Ian leads by example. He shared a telling story from early in his advocacy journey:

“I was speaking to an African American business group. The first questions were always ‘What box are you trying to check? Why are you here?’”

But Ian kept showing up. And his sincerity showed. Years later, attendees embrace him as their own. Because they know his care is real.

Like Soledad, Ian leans into tough conversations. It’s growth, notcomfort, that pulls us forward as individuals and a society.

This takes bravery. To let your heart guide when logic shouts to take the easy route.

But purpose gives us courage to change course — and change minds.

The Purpose and Passion Paradigm

Stories of Soledad and Ian reveal a shared truth:

True success lies beyond status and salary. It stems from uplifting others using your unique gifts.

This requires silencing the voices pushing us to conform. Of seeking validation from awards or money or acclaim.

Instead, we must listen within. Discover our inner light. Then let it guide us to light the way for others.

This purpose-first paradigm allows passion to flourish. When work aligns with mission, it energizes.

Sure, there will be obstacles. Unjust systems block much needed progress.

But purpose-driven leaders like Soledad and Ian show us the way forward. Their compassion sets an example to follow.

One exchange with Ian captured this ethos:

“Do what’s right. Treat people the right way,” he told me. “It’s simple.”

Simple, yes. But often forgotten.

The Winding Roadmap to Lasting Success

As a lifelong student of success, I’m fascinated by how life’s twists and turns shape our character and lead us to our true calling.

This was the overarching lesson from my inspirational conversation with acclaimed journalist Soledad O’Brien and financial advisor Ian Freeman.

Their remarkable careers exemplify how cultivating flexibility, resilience and conviction can unlock lasting success.

In our far-ranging dialogue, Soledad and Ian shared their winding journeys that revealed 4 key lessons for finding purpose and passion:

Lesson 1: Persevere through failure and embarrassing mishaps

Soledad O’Brien’s path to journalism glory was marked by rocky valleys as well as triumphant peaks. After realizing pre-med wasn’t her passion, she found her way into TV news production. This led to an on-air reporting role at an NBC affiliate station.

But Soledad’s early live shots were baptisms by fire:

“In my very first live shot ever, I was literally groped on air. Someone behind me pinched me on the behind. I was so new I didn’t even realize you shouldn’t let people stand behind you.”

Talk about being thrown in the deep end! But Soledad persevered through this humiliating experience and honed her craft. Her resilience enabled her to rise above embarrassing mishaps that would have made others quit.

Key lesson: Don’t let failures or mistakes derail your dreams. Stay determined even when the journey gets messy. Use every setback as a lesson to improve.

Lesson 2: Follow your inner compass, not external markers

Over years navigating TV news, Soledad realized true success is not defined by money or job titles. What matters most is:

  • Doing work you find meaningful
  • Collaborating with people who inspire you

Once she tuned into her inner compass, Soledad felt empowered to start her own production company. This gave her the creative freedom to tackle topics like systemic racism.

Key lesson: Don’t just climb the ladder others expect. Listen to your inner wisdom and create your own definition of success.

Lesson 3: Use your abilities to serve those in need

Whereas Soledad found clarity through her career twists and turns, Ian Freeman stumbled into finance but it never felt right. He shares:

“I went back to banking in Connecticut but realized there was no gratification. I couldn’t go through life feeling that way.”

Eventually Ian followed his heart and started his own firm. His “A-ha” moment came when a grieving widow’s call revealed his higher purpose — serving overlooked communities through financial education and planning.

Key lesson: Use your unique abilities not just to enrich yourself but to serve people and communities in need. This brings true fulfillment.

Lesson 4: Have the courage to take the unconventional path

Ian offered this advice on achieving success:

“At some point you must look in the mirror and step up. You can’t only do what’s right when it’s convenient. Either you do what’s right, or you don’t.”

Key lesson: Don’t just follow the herd. Have courage to take the road less traveled if it aligns with your passion and purpose.

The Purpose and Passion Paradigm

Soledad and Ian’s journeys reveal that real, lasting success requires internal clarity and conviction. It’s not about skill, hustle and charm alone. You need a clear sense of purpose beyond status and accolades.

Money itself will not satisfy. Think beyond superficial titles and symbols. Instead, fully utilize your unique talents to contribute value. Collaborate with people who expand your thinking. Derive meaning from the work itself.

This fulfilling path often requires the courage to pivot off the well-worn conventional track. As Soledad and Ian proved, success rarely follows a perfect script.

But with flexibility focused on purpose, your passion will ignite.

By walking your own winding road guided by inner wisdom, you will find success on your own terms.

And you just may change lives along the way.

What is the Success Story Podcast?

On this podcast, you’ll find interviews, Q&A, keynote presentations & conversations on sales, marketing, business, startups, and entrepreneurship.

The podcast is hosted by entrepreneur, business executive, author, educator & speaker, Scott D. Clary.

Scott will discuss some of the lessons he’s learned over his own career, as well as have candid interviews with execs, celebrities, notable figures, and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas, and insights.

He sits down with leaders and mentors and unpacks their stories to help pass those lessons on to others through both experiences and tactical strategies for business professionals, entrepreneurs, and everyone in between.


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