To The Top: Inspirational Career Advice

My next guest spent over two decades at the intersection of banking, venture capital, and the innovation economy — helping founders, fund managers, and investors build, grow, and scale some of the most exciting companies and firms in the world. He co-built one of the most respected venture banking practices in the country at First Republic Bank — and when that institution collapsed overnight in 2023, he did what great leaders do: he steadied his team, made the right call under enormous pressure, and rebuilt from scratch. Today, as Head of Emerging VC and Innovation Banking at Citizens Private Bank, he's doing it all over again — and by most accounts, better than ever. But what makes Sam Heshmati worth listening to goes beyond his résumé. He's someone who traveled the world at 24 with Richard Branson, lost everything in the 2008 real estate crash, rebuilt his career from his parents' couch, and came out the other side with a philosophy about work, leadership, and life that is as hard-earned as it gets. In

Mark Matson is the founder and CEO of Matson Money, one of the nation's leading financial coaching and investment advisory firms serving over 500 advisors and 35,000 families. A fierce advocate for evidence-based investing, Mark is the author of the six-time national bestseller The American Dream — which he narrated himself across 40 hours in the studio. Over 35 years, he's built a business on one core conviction: that speculation and gambling with money destroys futures, and that disciplined, science-backed investing builds them. Mark brings the same no-nonsense clarity to entrepreneurship, leadership, faith, and family that he brings to finance — and today, he's back for a second conversation. What you'll learn: Stop gambling with your money — Why Bitcoin, gold, hedge funds, and AI-powered day trading tools are speculation dressed up as investing — and what the actual science says about building lasting wealth Figure out what AI can't replace — The one question every professional needs to answer right no

You've read the books. You know what to do. So why aren't you doing it? That's the question my guest couldn't shake — and it sent him on a six-year journey that became his most important work yet. Nir Eyal is the author of the million-copy selling books Hooked and Indistractable, and his brand new book is called Beyond Belief. Nir argues that motivation isn't a straight line between knowing and doing — it's a triangle, and most of us are missing the third side entirely. That missing piece is belief. Today we talk about why successful people are actually just better losers, how your beliefs filter the reality you're able to see, and the simple but powerful practice that can make you up to 240 times more persistent. If you've ever felt stuck between knowing better and doing better, this conversation is for you. The real reason your motivation dies before you reach your goal — and it has nothing to do with discipline or willpower Why two people can look at the exact same situation and see completely different r

What if the secret to building a great career wasn't about having all the answers — but knowing how to ask the right questions? Today's guest, Yue Zhao, has lived that philosophy across one of the most varied and impressive career paths you'll hear on this show. Yue is a Chief Product & Technology Officer turned executive coach. She helps aspiring executives accelerate their careers and reach the C-suite. Yue worked at Thumbtack, Meta, Instagram, and growth-stage startups. She co-founded a wine startup out of Harvard Business School, helped shape the future of Instagram Feed at Meta, and led product at McKinsey-backed Thumbtack from a 20-person garage startup to a scaled technology company. But beyond the resume, Yue is someone who has thought deeply about what makes great leaders great, what it really takes to grow in your career, and why the best decision you can make isn't always the obvious one. She's also a career coach herself — so she brings both the frontline experience of building products peo

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