What if the values that made you who you are — resilience, service, empathy — could become the operating system for an entire organization?

Today's guest grew up in Hialeah, Florida, the son of Cuban immigrants who arrived in America with almost nothing and built everything through grit, integrity, and an unwavering belief that hard work is the price of admission. He lost his father at 12 years old, found his footing in the U.S. Army — where he'd eventually jump out of planes at night as part of an Airborne unit — and then quietly built one of the most storied careers in the travel industry.

David Herrera served as President of Norwegian Cruise Line, where over more than a decade he helped transform the company's commercial operations, led its expansion into China, and championed a genuine, veteran-driven military appreciation program that earned him letters, mugs, and thank-you notes from guests whose gratitude had nothing to do with the bottom line.

But what strikes you most about David isn't the titles or the milestones — it's that he leads the same way his mother lived, the same way his Army sergeant Mahoney taught him: from the front, with his word as his bond, leaving no doubt whose side he's on.

In this conversation, we talk about growing up in a Cuban immigrant household that embodied the American dream, what the military teaches you about trust and team that no MBA program can replicate, how he thinks about culture not as a poster on the wall but as the answer to the question — who's winning here, and why? — and what it really means to be a servant leader when the stakes are high.

In this episode we discuss:

• Hire your manager, not just your job. The person above you shapes everything about your early career experience. Choose them wisely.
• If you're not early, you're late. Punctuality is ultimately about respect — for other people's time and for the commitments you make.
• Share the victory, own the setback. When things go right, celebrate the team. When things go sideways, step forward and take responsibility.
• Culture is what gets rewarded. Not what's written on the wall — but who's winning in your organization and what it is about them that you actually respect and want to replicate.
• Treat everything as a learning opportunity. Doesn't matter if you're painting parking lots in Miami heat or running a division — be in the moment, observe what works, and study what doesn't so you can avoid it.
• Lead from the front. Never ask someone to do something you haven't done or aren't willing to do alongside them. That credibility is the foundation of real trust.
• Know your foxhole friends. Who in your life both genuinely cares about you and is capable of showing up when it counts? That combination is rarer than most people realize.
• Sometimes the right business decision comes at a personal cost. Separating emotion from judgment is one of the hardest and most important skills a leader can develop — and it never fully stops stinging.

What does a childhood obsession with comic books, a family health food store, and a Roberto Clemente rookie card have in common? For Howard Chasser, they're all threads in a life built around passion, people, and the relentless pursuit of doing work that actually means something. Howard spent over 30 years running a natural food store on Long Island that his parents opened in 1976 — navigating the loss of his father at 17, a monster expansion, a brutal economy, Superstorm Sandy, and a divorce — before walking away and ultimately finding his way back to what he'd loved since childhood: sports cards and collectibles. Today he runs a thriving sports cards business built not on transactions, but on trust, genuine enthusiasm, and an ability to make people feel like family. This is a conversation about reinvention, resilience, and what happens when you finally stop fighting what you were always meant to do.

In this episode, Howard shares:

• Why the things we're meant to pursue often find us before we're ready for them — and how a $68 baseball card his mom almost didn't buy changed the entire trajectory of his life
• How soft skills will outwork hard skills in the room — Howard was a B+ student surrounded by straight-A accounting majors, but his years behind a store counter made him the one people actually wanted to hire
• Why you can hold an apology and a boundary at the same time — the moment he snapped at an employee taught him that accountability and delivering a message aren't mutually exclusive
• What a difficult customer's secret revealed about human nature — the woman who cursed at his staff turned out to be a mother whose teenage daughter had terminal cancer, and it changed how he sees every hard interaction
• How the right door often only opens after the wrong one finally closes — after a year of uncertainty post-store, Howard reluctantly returned to card shows and stumbled into his true calling right before COVID sent the hobby through the roof
• Why your kids reflect your energy, not their own chaos — a therapist-backed insight that transformed how he showed up as a father, and a lesson that applies far beyond parenting

What if the secret to building a thriving business wasn't an MBA, a venture capital check, or even a business plan — but simply the courage to say yes before you're ready?

Today's guest is Eri Iozdjan, founder of Maven Lane, a premium direct-to-consumer furniture brand that's redefining what it means to bring quality, story, and soul to the spaces where we live our lives. Eri's journey is anything but conventional. He arrived in the United States from Bulgaria at age five, speaking no English, with his young mother and nothing but a relentless drive to figure it out. From working HVAC jobs as a teenager, to producing a New York Fashion Week runway show, to building a furniture brand that sells out its first inventory run in weeks — Eri is proof that the most unlikely paths can lead to the most extraordinary destinations.

In this episode, Eri pulls back the curtain on what it really takes to build something meaningful from the ground up — and why staying true to your vision, even when the money is tempting you otherwise, is the ultimate competitive advantage.

Here's a taste of what you'll walk away with:

• Why saying yes before you're ready is the single greatest career accelerator — and how Eri used it to go from knowing nothing about furniture to building a brand people call life-changing
• The complacency trap that derails even the most successful entrepreneurs — and the simple mindset shift Eri uses to stay sharp no matter how well things are going
• How a late-night dream gave Eri the name, the logo, and the soul of Maven Lane — and what it teaches us about trusting our instincts
• The phone call from a stranger that gave Eri the confidence to go all in — and why that one conversation changed everything about how he saw his business
• Why "nobody cares" is actually the most liberating career advice you'll ever receive — and how embracing it can unlock a level of ownership and accountability most people never find

This is a conversation about grit, creativity, identity, and the quiet power of just getting to tomorrow. You're not going to want to miss it.

What happens when a classically trained chef who cooked at Michelin-starred restaurants decides the future of cooking isn't fire—it's light?

Today's guest is Travis Rea, Head of Culinary at Brava, the company that's reimagining home cooking with an oven that uses infrared light instead of traditional heat. But Travis's path to revolutionizing kitchen technology wasn't straightforward.

Born and raised in Houston, he grew up watching his mom cook from scratch and fell in love with the transformation of ingredients at just eight years old. That passion led him to ditch a conventional business career for culinary school in San Francisco, where he spent four grueling years cooking at Restaurant Gary Danko—eventually helping the restaurant earn its Michelin star.

But after years of vampire hours and relentless pressure, Travis made a bold pivot back to the business world, spending eight years at Williams-Sonoma developing over 800 food products and collaborating with legendary chefs like Thomas Keller. When he first heard about Brava—a startup claiming they could sear a steak in seven minutes using light bulbs—he thought it was "total nonsense."

Now, eight years later, Travis has helped build a product that's been used over 13 million times, with a digital library of 9,000+ recipes. This is a story about knowing when to pivot, surrounding yourself with people smarter than you, and why the best career moves often require you to embrace being a beginner all over again.

What You'll Learn in This Episode:

• How failing a class became the wake-up call that changed everything – Why Travis's freshman year failure was "one of the best things that happened" to him and taught him the importance of living up to his own potential
• The real cost of following your passion – Why Travis walked away from Michelin-starred kitchens after realizing he loved cooking but couldn't sustain the restaurant lifestyle for 30 years
• How to know when you're ready for a pivot – The signals Travis noticed (and ignored) that revealed he was reading cookbooks while his peers read marketing journals, and what that meant for his career
• Why working for the best matters more than the biggest paycheck – Travis's philosophy on taking lower-paying jobs at elite organizations early in your career and how it compounds over time
• The white belt mentality in action – What it's like to be the only "cook" in a house full of physicists and engineers, and why being the least qualified person in the room might be exactly where you need to be

Get your free copy of The Career Pivot Playbook: https://www.omaid.me/newsletter

Sahand Dilmaghani is the founder and CEO of Terra Kaffe, a design-led coffee company reimagining the home espresso experience. Frustrated by the limitations of pod-based machines and the outdated technology dominating the super-automatic espresso category, Sahand set out to build something better—a beautifully designed, app-connected espresso machine that delivers café-quality coffee at the push of a button. What started with him walking the streets of SoHo with two prototypes and eating one meal a day to conserve cash has grown into a company serving tens of thousands of customers who demanded more from their daily coffee ritual. With a background spanning finance, hardware, and design, and fluency in Chinese that took him from Saturday school as a kid to manufacturing facilities in Shenzhen, Sahand brought a unique perspective to an industry that hadn't innovated in decades. Today, Terra Kaffe's machines—from the flagship TK-02 to the compact Demi—represent what happens when you refuse to accept the status quo and build with relentless attention to detail.

In this episode, you'll learn:

• How Sahand's parents' immigrant journey shaped his "everything is solvable" mentality and entrepreneurial grit
• The moment he realized the espresso machine industry was ripe for disruption—and why DeLonghi's executives completely missed it
• Why the best ideas get a 50/50 reaction—half your friends think you're crazy, half think it's brilliant—and why that's exactly where you want to be
• How to navigate the hundreds of daily decisions that can make or break your business without letting perfect become the enemy of done
• The critical difference between asking "should I do this?" versus "can I do this?"—and why it defines your entire career trajectory

Get your free copy of the Career Pivot Playbook here: https://www.omaid.me/newsletter

Dan Stein is a former recruiter at Google, SnapChat, and the VC firm A16Z. His wellness journey was featured in Men's Health and he launched an athletic apparel brand focused on mental health called Pax. Dan has also visited over 30 countries.

In this episode we discuss:

-The best career advice from a recruiter's perspective

-Why money is a renewable resource, advice from his dad that has helped him take more calculated risks

-How a cross-country move and a chance encounter with a waitress helped him land a job at Google

-Why "being seen" matters more than the perfect resume

-Why your manager can make or break your career

-The most important life lesson from visiting 31 countries

-What he means by 'finding what works for you' around health & fitness and more

Get my free Career Pivot Playbook to help navigate your next move: www.omaid.me/newsletter

Follow me on LinkedIn: www.linkedin.com/in/omaidhomayun/

My guest today is Josh Panko, President of Leaf Trading Cards. Josh's journey in the sports card industry started at age seven when he opened a card shop in his basement. That childhood passion turned into a remarkable career that's taken him from working at card shops as a teenager, to Upper Deck's product development team, to now leading one of the most creative trading card companies in the industry.

What I love about Josh's story is how he built his career by working every angle of the business—retail, distribution, manufacturing, customer service. He learned the entire supply chain, which gave him a perspective that few in the industry have. And today, at Leaf, he's creating some of the most innovative products in the space, from on-card autographs of Hollywood legends like Al Pacino and Clint Eastwood, to unique sports card concepts that major licensed manufacturers can't touch.

This conversation is packed with wisdom on hard work, taking initiative, building relationships, and staying humble even as you climb the ladder. Whether you're in the trading card world or not, Josh's lessons on career development and leadership are gold.

In this episode we discuss:

• Why working every level of your industry early in your career creates an unfair advantage - and how Josh's experience in retail, distribution, and manufacturing shaped his leadership at Leaf
• The handwritten letter strategy that landed Josh his dream job at Upper Deck - and why his father's unconventional advice to FedEx overnight it to the CEO actually worked
• How being kind to everyone (especially people outside your department) can fast-track your career - Josh's finance department friendships got his projects prioritized over senior colleagues
• Why Josh would rather employees take initiative and make mistakes than wait for permission - and the Shawshank Redemption lesson about not asking to go to the bathroom
• The "harder you work, the luckier you get" philosophy - and how Josh turned clocking out at 5pm then returning to work unpaid into career-defining opportunities

Get my free Career Pivot Playbook to help navigate your next move: www.omaid.me/newsletter

Follow me on LinkedIn: www.linkedin.com/in/omaidhomayun/

Kendall Berg is a career strategist and author of Secrets of the Career Game who helps ambitious professionals navigate corporate politics with integrity and transform strong performance into visible, undeniable value. After being told early in her career that "everybody loves having you on their team, but nobody likes working with you," she dedicated herself to learning the unspoken rules of advancement—and was promoted five times in six years. Now, through her coaching practice and her tactical, no-nonsense approach, Kendall teaches thousands of clients across 27 countries how to earn more, advance faster, and feel in control of their career trajectory without burning out or losing themselves in the process.

In this episode, you'll discover:

• Why your boss has NO idea what you're actually doing—and the weekly habit that fixes this blind spot
• The one person you must talk to during interviews that reveals the REAL company culture (hint: it's not the hiring manager)
• How asking for help makes people think MORE highly of you—the counterintuitive psychology that changes everything
• The "influencer list" strategy: Why you're networking with the wrong people and how to identify the 5 who actually control your career
• Why 82% of jobs are filled before they ever hit the job board—and what to do about it

Check out Kendall's website: www.thatcareercoach.net

Get my free Career Pivot Playbook to help navigate your next move: www.omaid.me/newsletter

Follow me on LinkedIn: www.linkedin.com/in/omaidhomayun/

Jamie Siminoff is the CEO and founder of Ring, the camera company that transformed home security. While his viral Shark Tank episode didn't yield a deal from the sharks, it launched the video doorbell company. In 2018, Ring sold to Amazon for $1 billion. Jame published a book titled Ding Dong: How Ring Went from Shark Tank Reject to Everyone's Front Door.

In this episode we discuss:

-the greatest lessons from his failures -the 1 question he'd ask James Dyson in an elevator -why often the most important decisions are the ones we say "no" to -how the best thing that never happened was not getting acquired by ADT -what he learned about the relationship between money and happiness -the best career advice he ever received -the nicest thing anyone has ever done for him and more

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Patrick Mouratoglou is one of tennis's most successful and unconventional coaches, known for his work with Serena Williams during her dominant return to form—helping her win 10 Grand Slams and reclaim the world number one ranking. But his journey to the top began in the darkest of places: a childhood marked by crippling shyness, zero self-esteem, and such severe social anxiety that he couldn't make eye contact without fear of vomiting. When his dream of becoming a professional tennis player was crushed at 15, that rock bottom moment became the catalyst for an extraordinary transformation. Today, Patrick coaches the next generation of champions, founded the innovative Ultimate Tennis Showdown (UTS), and has written a book about the "progress zone"—the space where confidence is built through small, daily victories. His approach to coaching is refreshingly transparent in a sport known for secrecy, and his insights on building champions apply far beyond the tennis court.

What You'll Learn in This Episode:

• Why the worst thing that happens to you might be the best thing—how Patrick's devastating rejection at 15 became the turning point that saved his life and launched his coaching career
• The hidden truth about motivation—why players (and people) who seem "unmotivated" are actually protecting their confidence, and what really drives elite performance
• How to rebuild someone's confidence from zero—Patrick's unconventional methods, including secretly rigging matches to create winning streaks and psychological breakthroughs
• What separates champions from great players—the mindset traits of Serena Williams, Roger Federer, and Novak Djokovic that have nothing to do with talent
• The art of hearing what people think, not just what they say—Patrick's most powerful coaching skill and why "the weather is nice" means completely different things in London versus Miami