#344 Sienna Jackson: From Hollywood to Hard Metrics — Part One
From film sets to SaaS, Sienna Jackson has lived through more than one reinvention. A two-time founder, former entertainment executive, and current tech CEO, she joins Chief Change Officer to break down what it means to build, to create, and to change—on your own terms. In Part 1, she shares what it was really like working in the music and production trenches at the Weinstein Company, how she navigated a high-glamour industry with clear-eyed curiosity, and why she never let a job title define her. But it’s her unfiltered take on generative AI that steals the show. Sienna dismantles the hype, calling it what it is: regurgitated content dressed as intelligence. From energy waste to algorithmic bias, she unpacks the hidden cost of convenience—and why human storytelling still matters.Key Highlights of Our Interview:From Red Carpets to Real Work“All the Quinton Tarantino films, all the Oscar Batty films… Project Runway… I also worked on our internal music catalog… and it would just be usually me and Richard for most of that run.”Curiosity > Career Ladder“I thought I was going to be the rebel… I was doing things during the Arab Spring… I also reported on the honor killing of one of my classmates when I was 16.”AI ≠ Creativity“Some people will say AI-generated art is art. And I think that’s a misnomer… Art is an action. It’s something that you do. It reflects technical skill that you have to develop over time.”The Hidden Cost of ‘Smart’“There are human beings at the other end of the pipeline… being paid pennies on the hour to train chatbots… it uses up 10 to 30 times more energy.”Garbage In, Garbage Out“GenAI will reify or reinforce patterns… there’ve been significant issues with algorithmic bias on the axes of race… who gets an insurance policy or not.”___________________________Connect with us:Host: Vince Chan | Guest: Sienna Jackson
--Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<
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#343 Brian Sims: From State House to Soul Work—Driving Change With Smarter Tools — Part Two
Brian Sims, the CEO of Agenda PAC, walks us through what it was really like inside the halls of power—getting his mic cut on the House floor, confronting closeted anti-LGBTQ colleagues, and learning the limits of both strategy and ego. Now in the private sector, he’s using data to fight back—not with louder voices, but with smarter ones.Key Highlights of Our Interview:When the Mic Goes Dead“I got half a word out. Then it cut. They didn’t even pretend it was technical.”No Friends Across the Aisle“They all voted against us—100% of the time. Colleagues? Yes. Friends? Absolutely not.”Losing the Big Fights“I wrote the Equal Pay Act. I wrote the state’s Marriage Equality bill. Neither passed. And I had to learn: that’s not failure—it’s legacy work.”Arrogance vs. Strategy“I thought just being bold was the answer. It wasn’t.”A New Way to Win“Now I use data to expose the gap—between what voters want and how leaders behave.”Fighting Dirty ≠ Fighting Back“There’s a difference. And it matters. You can run into the fire without lighting yourself on fire.”Change the Decision Makers, Not Just Their Minds“Every single thing I’ve ever cared about gets better when more women, more people of color, and more LGBTQ people hold power.”_______________________________Connect with us:Host: Vince Chan | Guest: Brian Sims
--Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<
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#342 Brian Sims: From State House to Soul Work—Driving Change With Smarter Tools — Part One
From a military childhood to a college football captain, Brian Sims didn’t exactly grow up in activist circles. But a fiercely independent mother and a slow-burning coming-out story set the stage for something bigger. In Part One, Brian, the CEO of Agenda PAC, opens up about finding his voice, leaving law for civil rights work, and eventually winning his first election—becoming the first out gay man elected to Pennsylvania’s state legislature.Key Highlights of Our Interview:Raised by Leaders“Both my parents were lieutenant colonels. I grew up on army bases, but my mom was always the only woman in uniform.”Confidence Is Contagious“She wasn’t arrogant. She just always knew who she was.”Coming Out Through Brotherhood“My football teammates asked if I was gay… and then wrapped me in the most awkward but beautiful kind of love.”A Gay Job and a Day Job“I had a law firm paycheck. But my soul work? LGBTQ civil rights.”Why He Ran“I couldn’t change their minds. So I ran to change the people holding the power.”David vs. Goliath“She’d been in office since I was three years old. I beat her by 233 votes.”_______________________________Connect with us:Host: Vince Chan | Guest: Brian Sims
--Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<
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#341 Jennifer Selby Long: Politics, Power, and the Choice to Stay or Go
In this final installment, Gen X executive coach Jennifer Selby Long goes deep on the real decision behind office politics: should you stay or should you go? Drawing from decades of experience guiding leaders through complex change, she lays out the subtle dynamics that determine whether a culture is salvageable—or just stuck. From the hidden toll of hybrid models to bosses who subtly push out high performers, Jennifer offers tools for cutting through confusion. And with a memorable framework inspired by civil rights leader Clarence Jones, she helps listeners evaluate not just what they want—but whether the system they’re in will ever let them have it. For Gen Xers caught in the gray area between loyalty and realism, this episode offers clarity with no illusions.>>Why Toxic Cultures Repeat“People leave a bad boss… only to land in a similar situation.”Jennifer explains how unaddressed internal patterns can reappear in new jobs—and what to do before making another move.>>Hybrid Work, Hidden Agendas“If your team isn’t working together in person, politics won’t disappear—they’ll just change form.”She discusses the tradeoffs of hybrid workplaces and how physical distance can mask, not eliminate, power struggles.>>When the Best Performers Leave“I’ve seen bosses quietly engineer ways to push out brilliant people.”Jennifer and Vince unpack the dynamic where insecurity—not excellence—shapes who gets to stay.>>Conflict is Not the Enemy“Most people waste time fighting battles that could’ve been solved with a conversation.”She breaks down how conflict-avoidance fuels politics—and why stepping back to understand styles and misalignment is essential.>>Clarence Jones’ Test for Staying or Leaving“You won’t prevail unless the powerful majority sees that what you want is in their interest.”Jennifer shares hard-earned political wisdom: how to evaluate whether your values and goals can survive the system—or if it’s time to walk._________________________Connect with us:Host: Vince Chan | Guest: Jennifer Selby Long
--Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<
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#340 Jennifer Selby Long: Office Politics Without the Eye-Roll
In this third installment with Gen X executive coach Jennifer Selby Long, we zoom in on one of the messiest, most misunderstood realities of modern work: office politics. Jennifer breaks down why politics often stem less from individual egos and more from structural dysfunction, emotional disconnection, and leadership blind spots—especially in hybrid teams. She explains how outdated views of leadership, chronic misalignment, and even cost-cutting decisions like slashed T&E budgets can quietly poison team trust. But this isn’t just a takedown—Jennifer arms listeners with a real-world playbook to navigate power struggles without becoming part of the problem. For seasoned professionals tired of performative team building and empty culture talk, this episode reframes politics not as inevitable—but as solvable.>>Politics ≠ Power-Hungry People“The majority of leaders are not political animals.”Jennifer challenges the stereotype that all office politics are about ego—revealing how misaligned strategy and trust gaps often create dysfunction.>>Remote Work’s Invisible Cost“You might not feel like getting on that plane… but complex decisions require in-person time.”She explains how budget cuts, virtual distance, and hybrid habits are quietly damaging team cohesion.>>Toxic by Design“I’ve worked with clients who were pretty mercenary at first… but some became the most dedicated leaders.”What happens when cold-blooded management isn’t an accident—but a strategy?>>Five Moves to Navigate a Political Culture“Stop venting. Start observing.”Jennifer offers a practical five-step approach to surviving—and even reshaping—a political workplace, starting with curiosity, not complaints.>>Why Some People Don’t Struggle with Politics at All“There’s a portion of the population just wired to be unbothered by it.”From temperament to neural wiring, she explains why some Gen Xers are naturally equipped to handle the drama without burnout._________________________Connect with us:Host: Vince Chan | Guest: Jennifer Selby Long
--Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<
What’s Stopping You from Outgrowing Yourself?
Change Ambitiously. Outgrow Yourself.
Chief Change Officer isn’t just another podcast. It ranks in the Top 3% globally, hit #1 in Careers (US), and cracked the Top 10 in Business (US)—because it offers what others don’t: expansive human intelligence, shared by the world’s most extraordinary thinkers and doers.
This is the space for transformation gurus, bold hearts, black sheep, and unsung visionaries. We go beyond digitized tips and AI-smooth talk. Here, you get real, time-tested, experience-driven wisdom—the kind that blends logic and love, art and science, hindsight and foresight.
For me, this show marks career transition #18. Across 17 transitions, I’ve been mentored by global changemakers who helped me emerge stronger and freer. Now, I’m passing that power forward—through raw, unfiltered conversations with extraordinary people across cultures, industries, and identities.
If you’re a growth progressive, a black horse, a visionary underdog, or someone boldly rewriting the rules—you’re already one of us. Because you are the Chief Change Officer.
Our mission?
To help you become wiser in action, clearer in thought, and more ambitious in motion—so you can outgrow yourself and unlock outcomes beyond imagination or calculation.
A better you is already unfolding.
130,000+ followers are outgrowing.
Join them on LinkedIn, Apple, Spotify, and YouTube @chiefchangeofficer.
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