To The Top: Inspirational Career Advice

Dr. Guy Winch is a psychologist, bestselling author, and one of the most trusted voices on emotional health in the world — his TED Talks have racked up over 35 million views, and his books have been translated into 30 languages. His latest, Mind Over Grind: How to Break Free When Work Hijacks Your Life, tackles burnout, rumination, and the invisible ways work bleeds into everything else — our relationships, our health, our sense of self. Guy also co-hosts the Ambie-nominated Dear Therapists podcast and has advised governments and companies like Unilever and Apellis on mental health. In this conversation, we get into what burnout actually feels like from the inside, why "finishing work" has nothing to do with closing your laptop, and the vacation science that changed how Guy himself takes time off, including: How to recognize it's time to quit your job The biggest mistake people make when decompressing after work The dangers of ruminating about work after work How to test for work culture during the interview process Why "who" you work for is the most important factor of your success and more Please consider leaving me a review!

Daniel Rausch is Vice President at Amazon, where he leads the Alexa and Echo business — the team behind one of the most ambitious consumer AI bets on the planet, with nearly 700 million devices sold. He joined Amazon in 2009 to work on Kindle in its earliest days (keyboard included, touchscreen not yet invented), drawn in by a single line from a recruiter: "We're not trying to be a consumer electronics company — we're changing the way everyone reads." That mission-first instinct followed him into building Echo and Alexa from scratch, and now into leading Alexa's complete generative-AI reinvention. Before Amazon, Daniel was COO of an ed-tech startup that he helped scale into the tens of millions in revenue — until the 2008 financial crisis gutted school technology budgets and forced a brutal reset. He holds a background in formal logic and philosophy.   In this episode we discuss: The recruiter pitch that changed everything — how one sentence about "changing the way everyone reads" convinced Daniel to leave a C-suite startup role for an individual contributor job at Amazon Learning from failure at scale — the story behind Alexa's "Let's Chat" feature, why it completely flopped, and what it taught the team about rebuilding vs. bolting on What it's really like to work with Jeff Bezos — the level of focus and seriousness Daniel says he brings to every single meeting, regardless of how big or small Avoiding complacency as a market leader — why owning a category (like Alexa does) is actually the most dangerous position to be in, and how he pushes his team to self-disrupt His best advice for landing a job at Amazon or big tech — standing out in a flooded applicant pool, and why being AI-fluent right now is a major differentiator The one house rule that shaped his parenting — why he never checked email in front of his kids, and how simple, concrete boundaries beat vague "work-life balance" goals Balancing career ambition with family sacrifice — moving his family across the country with three young kids and no support system, and what he'd tell someone weighing a similar risk  

My guest today is Jon McNeill — a man who grew up mowing lawns in a small farm town in Nebraska and went on to become the President of Tesla, working alongside Elon Musk during one of the most intense growth periods in the company's history. Before Tesla, Jon built and sold six companies, cutting his teeth at Bain & Company and Bain Capital Ventures, where he learned the fundamentals of business from some of the sharpest operators in the world — including a young partner named Mitt Romney. At Tesla, he helped scale the company from a niche EV maker into a global powerhouse, spearheading the push to 20X online sales and negotiating Tesla's landmark deal to build the first wholly-owned foreign auto factory in China. Today, Jon sits on the boards of both Lululemon and General Motors — two companies with a combined revenue approaching $50 billion — where he's known for an obsessive focus on product. He's also the author of The Algorithm, a book that distills the lessons from his career into a simple, repeatable framework for questioning assumptions, hiring for curiosity over IQ, and finding the two or three leverage points that actually move a business forward. In this conversation, we talk about growing up without a business household, what it was like getting case-interviewed by Elon Musk at 11 o'clock at night, the hardest decision of his career, and the career advice that took him from mowing ditches in Nebraska to the boardrooms of some of the biggest companies in the world.

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

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

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

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  

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.