To The Top: Inspirational Career Advice

Omaid Homayun
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We interview authors, entrepreneurs, and thoughts leaders to share their blueprints for success that you can also apply in your own life.

  1. Apr 7

    #134 Sam Heshmati: Don't Let Fear Kill Your Career

    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 this episode you'll learn: 1. Fear is not a reason to avoid opportunity Richard Branson's advice stuck with Sam for decades: assess the risk, and if it's worth it, don't let fear be the deciding factor. Fear alone is disqualifying yourself before you even try. 2. Never blindly follow a leader — ask questions The Victoria Falls barrel moment was the lesson Sam didn't expect. Just because someone you respect is willing to do something doesn't mean you should do it too. Qualify the risk yourself. 3. The first 13 years are for learning, not earning Don't chase titles, promotions, or salary bumps early on. Chase skills. If your employer won't reward those skills, someone else will — but you have to build them first. 4. Setbacks shape you more than success ever will Sam lost everything in 2008 and later watched his bank collapse overnight. Both experiences grew him more than any win. Wisdom comes from getting punched and staying standing, not from gray hair. 5. Solve problems, don't sell things Nobody wants to be sold to. Ask questions, listen, understand what the other person actually needs — and then bring that to the table. Sales is a byproduct of problem-solving. 6. Grittiness beats talent The world is full of smart, talented people. What separates high achievers is the willingness to outwork everyone else and adapt when things don't go as planned. 7. Early arrogance is a silent career killer Sam went on an apology tour years later for how he behaved as a young analyst. Be a sponge early on — you know far less than you think, and the people above you are watching. 8. Authentic relationships are your career infrastructure Being liked and building real relationships are not the same thing. In a small industry, genuine care and consistent value-add over time is what makes you the tiebreaker when it matters. 9. Set boundaries — no one will do it for you People respect the limits you clearly establish. If you don't define what matters outside of work, work will fill everything. And the people counting on you at home can't negotiate on your behalf. Get your free copy of The Career Pivot Playbook

    1h 23m

  2. Mar 24

    #133 Mark Matson: Recession-Proof Yourself

    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 now: what can you offer that a machine never will? Mark breaks down exactly where human value is irreplaceable Discipline is the real investment — Why even a perfectly engineered portfolio fails without this one ingredient, and the story of a woman who sat in cash for 25 years because she panicked once One bad apple costs you everything — What Mark learned from Pat Riley about core covenants, and the research that shows a single negative team member can destroy 80% of a group's productivity Do what you love, then outwork everyone — The hat salesman story his father told him as a kid that became the foundation of his entire philosophy on career and entrepreneurship Time accelerates faster than you think — What Mark says he'd tell his 40-year-old self, and why the gap between 40 and 60 feels like a flash compared to everything that came before it Download my free Career Pivot Playbook

    1h 9m

  3. Mar 13

    #132 Nir Eyal: Belief Drives Everything

    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 realities How to use belief as a tool — not a truth — to get unstuck and start moving The science-backed practice that even non-religious people can use to dramatically increase their pain tolerance and persistence Why stress and productivity are not the same thing (and the limiting belief that's quietly burning you out) How to stop being a prisoner of your own diagnosis, your own story, and your own excuses

    1h 24m

  4. Mar 4

    #131 Yue Zhao: The Best Leaders Don't Give You Answers

    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 people love and the perspective of someone who has helped countless others navigate pivotal career moments. Whether you're just starting out, stuck at a ceiling, or wondering if it's time to make a leap — this conversation is packed with hard-won insight you won't want to miss. Here's what you'll learn in today's episode with Yue Zhao: Why the best leaders never give you answers — and why that's actually the greatest gift they can give you How to choose your next job — and why your future manager matters more than the company name or the salary The one communication habit most product managers skip — and how mastering it will set you apart at any level What a wine startup, a bioengineering degree, and Instagram Feed have in common — and what Yue's winding path teaches us about building a career that compounds The mindset shift that changed how Yue coaches people — understanding what's within your control versus what isn't, and why confusing the two keeps so many talented people stuck Why two years is not that long — and how reframing the length of your career can take the pressure off your next decision The simple calendar trick Yue uses to get back on track — when life, work, or routines go sideways Land your dream job in half the time and get paid your worth with the Career Pivot Playbook for free: https://www.omaid.me/newsletter

    1h 6m

  5. Feb 24

    #130 David Herrera: Leave No Doubt

    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.

    1h 20m

  6. Feb 18

    #129 Howard Chasser: Love What You Do Or Start Over

    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

    1h 48m

  7. Feb 11

    #128 Eri Iozdjan: Having a Bias for Action

    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.

    1h 32m

  8. Feb 3

    #127 Travis Rea: Embracing the White Belt Mentality

    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

    1h 46m
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We interview authors, entrepreneurs, and thoughts leaders to share their blueprints for success that you can also apply in your own life.

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