To The Top: Inspirational Career Advice

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

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

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

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

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

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

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 MOR

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 -- go to www.omaid.me to sign up for the Career Compass newsletter where I share the best career advice from high achievers 

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

Steve Lucas is the CEO of Boomi, a leading integration and automation platform. Before joining Boomi, Steve served as CEO of Marketo, where he led the company's transformation from a $1.6 billion valuation to its acquisition by Adobe for $4.75 billion in just 24 months—one of the largest software acquisitions in history. Prior to that, he held executive leadership roles at SAP and Salesforce, and cut his teeth in technology at Microsoft in the early 1990s. Steve is the author of "Digital Impact," exploring how AI and intelligent automation are reshaping business and society. A passionate advocate for diabetes research after being diagnosed with type 1 diabetes at 26, he serves on the board of the Children's Diabetes Foundation and recently established an endowed chair for diabetes research at the University of Colorado. Known for his curiosity, authenticity, and unwavering commitment to customers—he makes it a rule to speak with at least one customer every single day—Steve brings a unique blend of technical

Jeff Pearlman is a New York Times bestselling author and one of America's most compelling sports writers, known for his meticulous reporting and ability to bring readers inside the locker rooms and lives of sports' most fascinating figures. He spent years as a writer for Sports Illustrated, where he famously broke the John Rocker story and honed his craft of finding extraordinary stories in unexpected places. Pearlman has authored numerous bestsellers including "The Bad Guys Won" about the 1986 Mets, "Showtime" about the Lakers dynasty which became an HBO series, "Boys Will Be Boys" about the Dallas Cowboys, and books on Bo Jackson, Walter Payton, Brett Favre, and Tupac Shakur—the latter requiring interviews with 650 sources. His YouTube show "Press Box Chronicles" has become a viral sensation, with millions tuning in to hear him share nostalgic deep dives into sports history's most memorable moments, characters, and forgotten stories. Today, Jeff continues to prove that great storytelling is built on o

Max Richter grew up in Stuttgart, Germany, surrounded by cameras—his father was a photographer with a Leica who ran an advertising business. After studying engineering and business, Max found himself restless in corporate life, eventually making his way to Shenzhen, China, where he met a campus legend named JK who had borrowed $2,000 from his father to start a camera company. What happened next was a decade-long journey of near-bankruptcy, pivotal pivots, and ultimately building Insta360 into a company that challenged GoPro and partnered with the very camera brand that filled Max's childhood home. Today, Max serves as a co-founder of Insta360, a company that's redefined how millions of people capture and share their lives. In this episode, you'll discover: The "dark year" of 2017 when Insta360 had over 100 employees, was running out of cash, and Samsung had just entered their market—and the unexpected user behavior that saved the company Why the moment you're closest to giving up is often the exact moment yo

Jay Shetty has inspired millions of people through his inspirational YouTube videos, best-selling books and his podcast, On Purpose. He shares much of his wisdom as a former monk through his teachings. In this interview we discuss: -The #1 trait of high performers -The hardest part of finding your purpose -Why we should study people instead of envying them -The best career advice he ever received  -What we get wrong about trauma -How to cultivate meaningful relationships and more.. -- email questions to omaid@omaid.me

Keith "Pistol" Hawk was VP of Sales at LexisNexis where he led a salesforce of over 1,000 people. He co-authored "Get-Real Selling: Your Personal Coach for REAL Sales Excellence" and he's given many keynote speeches at corporate events about leadership.  In this episode we discuss: -How his upbringing helped him become self-reliant at an early age -The power of presence when raising children -The keys to a long, happy marriage  -Pitfalls of leadership -Having hard conversations at work, and more -- email questions to omaid@omaid.me

Ariel Kaye is the founder and CEO of Parachute, the Los Angeles-based home essentials brand she launched in 2014. With no prior retail experience, Ariel transformed a simple observation about the lack of quality, non-toxic bedding into a multi-million dollar company that has redefined the direct-to-consumer home goods space. Before founding Parachute, she worked in marketing and media, experiences that proved invaluable in building a brand known for its storytelling and customer-centric approach. Today, Parachute operates retail stores across the country and has partnered with major retailers like Target, all while maintaining its mission of bringing comfort and quality into people's homes. In this episode we discuss: Why "I'll figure it out" is a legitimate business strategy – How embracing uncertainty and learning as you go can be more powerful than having all the answers upfront The transformative power of belief – How one friend's confidence in her abilities changed everything, and why believing in other

We're joined by Jeanelle Teves, Chief Commercial Officer of North America at Bugaboo, the premium Dutch stroller company known for its innovative design and engineering excellence. Jeanelle's career journey is a masterclass in turning uncertainty into opportunity—from answering phones at her parents' dental practice at age nine to scaling global brands at Nike across Europe and New York, and now leading growth for one of the world's most recognizable parenting brands. As a first-generation Filipino American who lived in the Netherlands for nearly a decade before becoming a new mother herself, she brings a unique perspective on building careers, leading teams, and creating products that truly solve problems for parents worldwide.  In this conversation, you'll learn: -The "Why Not You?" mindset that her immigrant parents instilled and how it shaped every major career decision -Her 5 AM routine and "3-3-3 exercise" for starting each day with intention and gratitude -Why being "consistently good beats being occas

In this episode, I sit down with Tim Bantle, President of heritage brand Filson and the former Patagonia executive who helped transform a $200 million company into a billion-dollar global powerhouse. From his philosophy degree to building some of the outdoor industry's most iconic products like the Nano Puff, Tim shares the unconventional path that led him to the top of two legendary American brands. You'll discover why he doesn't have a resume, how a family crisis became his greatest career opportunity, and the simple advice from his optician father that shaped his entire approach to business. Tim reveals the leadership strategies that actually work—from asking questions for six months before making changes to why authenticity is your ultimate competitive advantage. Whether you're climbing the corporate ladder or building your own business, this conversation is packed with practical wisdom from someone who's actually done it. What We Discussed: From Philosophy Student to Outdoor Industry Leader - How Tim's

Sara Sugarman is the founder and CEO of Lulu and Georgia, a leading online home décor brand that democratizes access to beautiful, designer-quality furnishings at accessible prices. Coming from a third-generation design family—her grandfather founded a pioneering rug company in Los Angeles in the 1950s—Sara initially worked in magazines at O Magazine under Gayle King before joining her family's decorative carpet business. She launched Lulu and Georgia as a side project in the early 2010s, naming it after her grandfather Lou and father George, with the mission to make high-end design accessible to everyday consumers rather than just interior designers. The company experienced explosive growth, particularly during COVID-19, and has become known for its successful influencer collaborations and empathy-driven customer service. As a working mother of three, Sara leads with an entrepreneurial philosophy focused on trusting employees, avoiding micromanagement, and creating a company culture where people can make mea

Sam Vander Wielen is the founder of a multimillion-dollar legal templates business and author of "When I Start My Business I'll Be Happy: A Practical, No-BS Guide to Successful Online Entrepreneurship." As a former corporate attorney turned entrepreneur, Sam provides legal templates and education to online business owners, helping them protect themselves and their businesses without the anxiety or expense of hiring a lawyer. After pivoting from a brief stint as a health coach, Sam discovered her niche when fellow entrepreneurs kept asking her legal questions at a wellness conference. Today, her signature product, the Ultimate Bundle, has generated over $8 million in revenue, while her weekly newsletter "Sam's Sidebar" reaches more than 47,000 subscribers. In this episode, you'll learn how Sam discovered her multimillion-dollar business idea by listening to her audience at a wellness festival, where people lined up for legal advice instead of health coaching You'll discover why Sam believes starting with a vi