Explore every episode of the podcast To The Top: Inspirational Career Advice
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|---|---|---|---|
| #137 Dr. Guy Winch: How to Break Free When Work Hijacks Your Life | 24 Jul 2026 | 00:53:18 | |
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:
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| #136: Daniel Rausch: Disrupt Yourself First | 14 Jul 2026 | 01:00:42 | |
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:
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| #135 Jon McNeill: The Algorithm That Transformed Tesla | 06 Jul 2026 | 01:01:27 | |
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. | |||
| #134 Sam Heshmati: Don't Let Fear Kill Your Career | 07 Apr 2026 | 01:22:57 | |
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. | |||
| #133 Mark Matson: Recession-Proof Yourself | 24 Mar 2026 | 01:08:35 | |
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:
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| #132 Nir Eyal: Belief Drives Everything | 13 Mar 2026 | 01:24:07 | |
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.
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| #131 Yue Zhao: The Best Leaders Don't Give You Answers | 04 Mar 2026 | 01:05:58 | |
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:
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
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| #130 David Herrera: Leave No Doubt | 24 Feb 2026 | 01:20:10 | |
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:
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| #129 Howard Chasser: Love What You Do Or Start Over | 18 Feb 2026 | 01:48:07 | |
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:
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| #128 Eri Iozdjan: Having a Bias for Action | 11 Feb 2026 | 01:31:34 | |
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:
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. | |||
| #127 Travis Rea: Embracing the White Belt Mentality | 03 Feb 2026 | 01:46:12 | |
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:
Get your free copy of The Career Pivot Playbook: https://www.omaid.me/newsletter
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| #126 Sahand Dilmaghani: Everything Is Solvable - Building Terra Kaffe Against All Odds | 28 Jan 2026 | 01:26:32 | |
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:
Get your free copy of the Career Pivot Playbook here: https://www.omaid.me/newsletter | |||
| #125 Dan Stein: Career Truths Nobody Tells You | 19 Jan 2026 | 01:44:59 | |
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/ | |||
| #124 Josh Pankow: Becoming Indispensable | 12 Jan 2026 | 01:13:06 | |
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:
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/ | |||
| #123 Kendall Berg: Secrets of the Career Game | 05 Jan 2026 | 01:19:15 | |
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:
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/
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| #122 Jamie Siminoff: Lessons From Building Ring | 29 Dec 2025 | 00:32:31 | |
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 -- go to www.omaid.me to sign up for the Career Compass newsletter where I share the best career advice from high achievers | |||
| #121 Patrick Mouratoglou: Building Unshakeable Confidence | 22 Dec 2025 | 01:11:10 | |
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:
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| #120 Steve Lucas: Embracing Your Superpowers | 16 Dec 2025 | 01:16:33 | |
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 expertise and people-first leadership to one of technology's most transformative eras. In this episode, we discuss:
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| #119 Jeff Pearlman: The Art of Storytelling | 05 Dec 2025 | 01:10:33 | |
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 one simple principle: getting the details right and treating people with kindness along the way. In this episode we discuss: -Why getting the facts trumps fancy writing -Why we should build relationships through kindness -Why other people's success doesn't diminish yours -His extraordinary story he published on 9/11 and more.. - email questions to omaid@omaid.me | |||
| #118 Max Richter: Moving Fast and Breaking Things - Buidling Insta360 | 11 Oct 2025 | 01:12:10 | |
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:
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| #117 Jay Shetty: On Finding Your Purpose | 05 Aug 2025 | 01:06:49 | |
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 | |||
| #116 Keith Hawk: Relentless Focus on the Process | 31 Jul 2025 | 01:17:30 | |
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 | |||
| #115 Ariel Kaye: The Art of Progress Over Perfection | 22 Jul 2025 | 00:57:46 | |
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:
-- Check out the t-shirts for the podcast: https://www.bonfire.com/to-the-top-4/
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| #114 Jeanelle Teves: Unshakeable Self-Confidence | 17 Jul 2025 | 00:44:49 | |
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 occasionally great" and how small, compound actions build extraordinary careers -The art of "praising in public and criticizing in private" to build psychological safety and high-performing teams -How she identified the perfect career opportunity at the intersection of personal experience and professional growth -Bugaboo's obsessive approach to solving real parental problems and why their durability standards are seven times higher than industry minimums -The power of treating your network like a bank account and making relationship deposits before you need to make withdrawals Whether you're early in your career or leading teams of your own, Jeanelle's insights on communication, consistency, and finding green shoots of optimism even in challenging times will change how you think about building both professional success and personal resilience. | |||
| #113 Tim Bantle: Authenticity is Your Competitive Advantage | 24 Jun 2025 | 00:52:54 | |
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:
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| #112 Sara Sugarman: Empathy is Your Competitive Advantage | 22 May 2025 | 00:50:34 | |
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 meaningful impact. Her journey represents a modern evolution of family legacy, transforming traditional design industry practices for the digital age. In this episode, we discuss: 1. Trust People and Let Them FailSara's father taught her that "any decision is better than no decision" and the importance of not micromanaging. She learned that failure isn't actually failure—it leads to success and opportunity. As a leader, giving people autonomy to make decisions (even wrong ones) builds stronger, more capable teams than controlling every outcome. 2. Follow Your Passion, Not a Predetermined PathSara studied English and Psychology without a clear career plan, worked in magazines, and eventually found her way to entrepreneurship organically. She didn't follow traditional business school routes or entrepreneurial playbooks, proving that authentic success often comes from pursuing what genuinely interests you rather than forcing a prescribed formula. 3. Experience Trumps Formal EducationWhen Sara wanted to attend business school, her father refused to pay for it, telling her "if you want to learn business, you're going to work for me." She acknowledges that while she missed out on some formal skills like accounting, the hands-on experience taught her invaluable lessons that couldn't be learned in a classroom. Real-world application often provides deeper learning than theoretical study. 4. Empathy is Your Competitive AdvantageSara's approach to customer service centers on understanding that home décor purchases are tied to important life moments—parties, new babies, family gatherings. By genuinely empathizing with customers' disappointments and taking authentic action to fix problems, you build lasting relationships that differentiate your business from competitors who treat interactions as transactions. 5. Constraints Can Force Better Decision-MakingHaving three children while running a company taught Sara the power of intentional time management. Working mothers, she notes, "know how to prioritize" and "spend their time really wisely" because time is limited. Rather than seeing constraints as limitations, they can force you to focus on what truly matters and make more decisive, efficient choices in both life and business.
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| #111 Sam Vander Wielen: The Million Dollar Pivot | 09 May 2025 | 01:09:10 | |
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.
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| #110 Garry Ridge: A Masterclass in Culture Building (Former CEO, WD-40) | 16 Apr 2025 | 01:03:12 | |
In this enlightening conversation with Garry Ridge, former CEO of WD-40 Company, you'll discover powerful leadership insights that transformed an ordinary product into an extraordinary company. Here's what to expect:
The interview offers a masterclass in building cultures where people feel they belong, know they matter, and can contribute meaningfully - all proven through 25 years of leadership without a single layoff. | |||
| #109 Rich Gannon - The Playbook for Building Mental Toughness | 09 Apr 2025 | 00:33:35 | |
Rich Gannon is a former NFL MVP and quarterback for the Vikings, Chiefs, and Raiders. He's currently a broadcaster and analyst for CBS. In this interview we discuss: -How he responded when he was at a crossroads in his career -How his experience in Minnesota and Kansas City may have prepared him for the unique situation in Oakland -What made him believe the Raiders would give him the 'keys to the kingdom' -What he did to change the culture at the Raiders -How to move on from a bad play, his favorite comeback win and more.. | |||
| #108 Raffi Grinberg: The 14 Essential Skills You Didn't Know You Needed | 31 Mar 2025 | 00:56:45 | |
Today we're sitting down with Raffi Grinberg, author of "How to Be a Grownup: The 14 Essential Skills You Didn't Know You Needed Until Just Now." After walking away from Wharton's MBA program just two weeks before it started, Raffi challenged conventional wisdom and created a wildly popular college course teaching the life skills most schools never address. His journey from management consultant to educator offers a refreshing perspective on designing a meaningful life in a world that tries to program our decisions. In this enlightening conversation, we explore:
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| #107 Ximena Vengoechea: The Counterintuitive Secrets of Listening That Will Transform Your Relationships | 06 Mar 2025 | 01:09:57 | |
Ximena Vengoechea has been UX researcher at companies like Twitter and Pinterest. She is the author of several books including the one we discuss today titled Listen Like You Mean It: Reclaiming the Lost Art of True Connection. Her writing has been published in The Washington Post, Newsweek, Fast Company, CNBC, The Muse, among others. She writes a regular newsletter on personal growth and human behavior at ximena.substack.com. In this inteview we discuss:
-- email questions to omaid@omaid.me | |||
| #106 Jeff Byers: Building Trust Through Transparency | 26 Feb 2025 | 00:46:15 | |
Jeff Byers is the co-founder and CEO of Momentous, a leading vitamins and supplements brand. He played college football at USC under legendary caoch, Pete Carrol. He also played in the NFL. In this episode we discuss:
-- email questions to omaid@omaid.me
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| #105 David Guttman: Leading Your Career With Humility | 16 Feb 2025 | 01:00:21 | |
In a candid conversation from his Miami office, veteran tech executive Dave shared insights from his journey from IT consultant to running companies with thousands of employees. A former wrestler and Division I athlete, Dave's path has been anything but conventional - from managing a help desk at 24 to leading multiple successful exits and navigating the volatile crypto space. Known for interviewing every single employee when he joins a company (whether it's 20 or 100 people), his philosophy centers on humility and service to others. "If someone isn't humble, doesn't matter what their talent stack looks like," he says about his top hiring criteria. After raising millions in capital, managing over a dozen acquisitions, and developing innovative business models that disrupted established players, Dave's most profound insight might surprise you: success isn't about being the smartest person in the room, but about being the most willing to learn from others. His advice to spend 100 hours a year mastering new skills (just 18 minutes daily) offers a practical roadmap for continuous improvement in an era often characterized by quick fixes and instant gratification. Here's what you'll learn from this interview with Dave:
-- email questions to omaid@omaid.me | |||
| #104 Jared & Jordan Schmidt: How Two Brothers Disrupted The Cutlery Industry | 13 Feb 2025 | 01:32:32 | |
Jared and Jordan Schmidt are brothers who disrupted the cutlery industry by making high-quality, beautifully designed knives affordable. They share the life and career lessons they learned through their journey that led from a concept to a successful company. You can find Schmidt Bros knives in over 10,000 retail locations across the country. In this episode we discuss:
-- email questions or comments to omaid@omaid.me | |||
| #103 Albert Chow: Why Fear Can Be A Healthy Motivator | 04 Feb 2025 | 00:53:59 | |
This interview explores the journey of Albert Chow, co-founder of Silk & Snow, a Canadian sleep & lifestyle company that started as a mattress-in-a-box business. Chow discusses how his immigrant parents and blue-collar background influenced his business approach, particularly his focus on supply chain transparency and quality manufacturing. Through organic growth and without outside funding, the company evolved from a Kickstarter campaign in 2017 to a successful acquisition by Sleep Country in 2023, maintaining its commitment to sustainable, high-quality products throughout its growth. In this episode we discuss: -Why Albert emphasizes the importance of staying true to your values, even when faced with trends or easier paths -Why he advocates for strategic risk-taking, noting how he first "de-risked" his life (established career, marriage, home) before starting his business -Why operating with a healthy amount of fear can be a powerful motivator -Being passionate about what you do is essential since your career occupies 60-70% of your life
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| #102 Amir Loloi: The Importance of Reputation | 28 Jan 2025 | 01:14:21 | |
This is the story of Amir Loloi, the founder of Loloi Rugs, one of the largest rug companies in America. It traces his remarkable journey from arriving in Dallas as a 16-year-old Iranian immigrant in 1976, barely speaking English, to building a 650-person company that has transformed the rug industry. Through early jobs at Burger King and driving an ice cream truck, to spending 25 years learning the rug business before starting his own company, Amir shares how his father's advice to "walk a straight line" shaped his business philosophy of integrity and constant improvement. The interview explores how he built his success through reputation and relationships, eventually bringing his two sons into the business to help create a lasting legacy. It's a quintessential American dream story that illuminates the power of perseverance, the importance of reputation, and the value of staying focused even after achieving success. | |||
| #101 Dan Martell: How to Buy Back Your Time | 22 Jan 2025 | 01:13:27 | |
Dan Martell is the bestselling author of "Buy Back Your Time" and a growth coach for business leaders. He is also the founder of Martell Ventures, a portfolio of companies that makes over $100M in revenue. After spending time in jail and rehab at the age of 17, Dan turned his life around. He taught himself to code, founded and led 3 tech companies to exit, and has invested in over 60 startups. Dan was named Forbes Top 10 Business People to Follow on Social Media and is a highly sought-after speaker, including events by Tony Robbins, John Maxwell, and other top leaders. His content, keynotes, and coaching programs have helped thousands of clients unlock growth, get fit, and develop the mindset to become the best version of themselves. In this interview we discuss: -How to implement the methodology of Buying Back Your Time -How to structure our time to maximize our energy -The most common pitfalls to watch out for when trying to maximize buying back your time -- email questions to omaid@omaid.me | |||
| #100 Coach Jon Gruden: The Keys to Building a Championship Mindset | 16 Jan 2025 | 00:51:49 | |
Coach Jon Gruden won a Super Bowl as the head coach of the Tampa Bay Buccaneers. He previously led the Oakland Raiders to prominence, and hosted Monday Night Football. He's currently joined Barstool Sports and has a YouTube channel called Gruden Loves Football where he breaks down game previews and interviews NFL players and coaches. In this episode we discuss: -the traits of a Gruden Grinder -why it's important to be a lifelong learner (or to accumulate knowledge) -lessons from Bill Walsh and Al Davis -how to build your adaptability muscle -how to handle pressure better -how to improve your attention to detail -why it's important to be ready when opportunity knocks and more -- email questions to omaid@omaid.me | |||
| #99 Dwayne Cowan: Exponentially Grow Your Career By Leading With Openness | 27 Nov 2024 | 00:54:50 | |
Dwayne Cowan is the President of the Residential HVAC business at Trane Technologies. He earned his degree in biological engineering from the University of Georgia and his MBA from the Arizona State University. For nearly 20 years he's led teams in the HVAC industry both at Thermo King and now Trane -- which is widely known as the leader in the HVAC industry. In this episode we discuss: -the importance of preparation -why the best leaders are inclusive -why asking for help is a sign of courage -why the best leaders usually don't have all the answers -why you should lead with openness in your life and career and more.. -- email questions to omaid@omaid.me | |||
| #98 Mark Matson: Redefining the American Dream | 17 Sep 2024 | 01:04:04 | |
Mark Matson is a financial expert and investment advisor. As the founder and CEO of Matson Money, his firm has $8.6B in assets under management while serving 35,000 families nationwide. Mark published his book, Experiencing the American Dream: How to Invest Your Time, Energy, and Money to Create an Extraordinary Life. During our interview, we discuss: -Why money can't buy happiness -The misconceptions we've been taught about The American Dream -How we can change our relationship with money and (and basic finance tips) -How challenging experiences can build character -Why sometimes your greatest strength can also be your weakness and much more.. -- email questions to omaid@omaid.me | |||
| #97 Richard Krulik: Viewing Problems as Opportunities | 10 Sep 2024 | 00:52:52 | |
Richard Krulik is the CEO of Briggs & Riley, a well established luggage brand that has been in existence for over 30 years. Richard and I discuss the rich history including: -how he onboards new employees to create a better culture at work -why good companies are built on trust -how to prepare in advance of chaos, or as he says "fly the plane" -how his father led by example -what he hopes his team would say about him as a leader -why it's important to view problems as opportunities -how they demonstrate company values like "smart & steady" -why it's important to travel for personal growth | |||
| #96 Tessa West: Finding Work That Works For You | 03 Sep 2024 | 01:29:50 | |
Tessa West is a professor of psychology at NYU. She's the author of Jerks at Work and Job Therapy: Finding Work That Works For You. Tessa's TED Talk -- The Problem With Being "Too Nice" at Work has nearly 800,000 views. In Job Therapy she provides a science-backed handbook that will help you better understand your relationship with your job and how to improve it. She also discusses the most common reasons why people are frustrated in their careers and how to address them. In this episode we discuss: -debunking career advice myths -how to balance emotion & logic when making career decisions -the difference between the person who sends hundreds of resumes out with no plan vs the person who takes action -the 5 sources of career frustration and more -- email questions to omaid@omaid.me | |||
| #95 Kim Scott: How to Work Together Better | 27 Aug 2024 | 01:01:12 | |
Kim Scott has worked in leadership roles at companies like Apple and Google. She is also a best-selling author as her book, Radical Candor, is one of the most beloved business books of the last decade. In Radical Respect: How to Work Together Better -- she details how organizations that optimize for collaboration and honor everyone's individuality are often more successful, joyful places to work. In this episode we discuss: -Why it's the leaders' responsibility to call out bias on a team -The significance of fostering a respectful culture at work -What we can all do to aspire to be better teammates (being an upstander) -Book recommendations and more.. -- email questions to omaid@omaid.me | |||
| #94 Dan Harris: Lessons from Taming the Voice in Your Head | 21 Aug 2024 | 00:46:16 | |
Dan Harris was an award-winning ABC Journalist who anchored Nightline. He's widely known for having a panic attack on national TV. Through a lot of inner work, he published 10% Happier about his traumatic experience and how he was able to rehabilitate himself which included practices like meditation. Dan's TED Talk on self-compassion has eclipsed 3 million views. We discuss his work including: -What he learned about himself through interviewing hundreds of people -The inflection point that led to his 360 assessment to understand what people really think of him -What he learned from his mentor, Peter Jennings -What he recommends to try to strike balance in life -- email questions to omaid@omaid.me | |||
| #93 Brianna Wiest: Defeating Self-Sabotage | 14 Aug 2024 | 00:45:09 | |
Brianna Wiest is the best-selling author of The Mountain Is You, 101 Essays That Will Change The Way You Think, and The Pivot Year. Her books have been read by millions of people and she is widely recognized for her wisdom of navigating life's challenges. In this episode we discuss The Mountain Is You including: -the definition of self-sabotage -the ways you can recognize self-sabotage -how we can begin to course correct -the significance of following your intuition or gut -what she's learned about happiness and more.. -- email questions to omaid@omaid.me | |||
| #92 Scott Tannen: Disrupting the Status Quo to Make an Impact | 22 Jul 2024 | 01:17:47 | |
Scott Tannen is the founder and CEO of a luxury linen and home goods company called Boll & Branch. They're best known for their luxury organic cotton bed sheets. Scott began his career working for established consumer packaged goods brands like Nabisco and Wrigley where he led digital marketing teams. He went to become the founder of Boll & Branch with the goal of bringing products to market that were sustainable for cotton farmers that eventually disrupted an industry. You'll enjoy this episode if you're curious about: -How mentors can challenge you to level up your game -How our parents can influence our life and career decisions -Why it was important for Scott to invest 2 years figuring out how to make products in a sustainable way that was good for people and the environment -How is $2 million bet with Howard Stern paid off -Why you should never sacrifice things that are important to you that you'll regret for work (and how to do it) and more.. -- email comments or questions to omaid@omaid.me | |||
| #91 Jacob Pechenik: Embracing the Beginner's Mindset | 27 May 2024 | 01:11:21 | |
Jacob Pechenik is the co-founder and CEO of Lettuce Grow, a company that makes hydroponic, self-watering farm stands that help you grow your own fresh fruits and vegetables at home -- the way nature intended. Jacob has sustained success in multiple industries and brings a unique perspective in terms of what habits and mindset has helped him over the years. In this episode we discuss the mission behind Lettuce Grow including: -How he's been able to sustain excellence in multiple careers -How in hindsight, his past expereince became the stepping stones for his most important work -How to embrace the beginner's mindset, and more.. -- email questions or comments to omaid@omaid.me | |||
| #90 Ryan Hawk & Brook Cupps: The Score That Matters | 05 Apr 2024 | 01:23:12 | |
The Score That Matters is a book by Ryan Hawk and Brook Cupps about personal excellence and narrowing down on what really matters in your life rather than comparing yourself to others. Ryan is the host of The Learning Leader Show, 3-time author and a keynote speaker. Brook is the head basketball coach at Centerville High School in Ohio where they've won a state title and are one of the top teams in the nation. In this episode we discuss: -Core values and how to develop them -The importance of foxhole friends both personally and professionally -The importance of trust and your reputation, and more.. --- email questions to omaid@omaid.me | |||
| #89: James Clear: Making Habits Stick & Breaking Bad Ones | 04 Mar 2024 | 00:43:55 | |
James Clear is a habit formation expert. His book, Atomic Habits, has sold over 20 million copies. He ships a weekly newsletter to 3 million subscribers. His new app, Atoms, is the digital extension of his book to help people make their habits stick. In this episode we discuss: -The difference between someone who can lose 180 lbs doing P90X compared to the one who won't make a change -The deepest level of behavior change, identity-based goals, and how to achieve them and stay on track -How to break bad habits, and more.. -- email questions to omaid@omaid.me | |||
| #88 Michael Lombardi: How History Shapes Our Future | 31 Jan 2024 | 00:59:09 | |
Michael Lombardi is one of the leading experts in analyzing the NFL. He currently hosts The GM Shuffle and recently published his second book, Football Done Right, which pays homage to the history of the NFL and former great players and coaches. He's the former General Manager of the Raiders and Patriots, and he learned the game as a scout under the legendary Bill Walsh with the San Francisco 49ers in the mid 1980s. In this episode we discuss: -The impact of Monday Night Football in pop culture -How he got his break at UNLV -The impact of Bill Walsh had on him as a lifelong learner -Draft picks that were successful and ones that he regrets -Advice to his sons on how to be the best coaches and more.. --- consider leaving a review and email questions to omaid@omaid.me | |||