To The Top: Inspirational Career Advice

Dan Stein is a former recruiter at Google, SnapChat, and the VC firm A16Z. His wellness journey was featured in Men's Health and he launched an athletic apparel brand focused on mental health called Pax. Dan has also visited over 30 countries. In this episode we discuss: -The best career advice from a recruiter's perspective -Why money is a renewable resource, advice from his dad that has helped him take more calculated risks -How a cross-country move and a chance encounter with a waitress helped him land a job at Google -Why "being seen" matters more than the perfect resume -Why your manager can make or break your career -The most important life lesson from visiting 31 countries -What he means by 'finding what works for you' around health & fitness and more Get my free Career Pivot Playbook to help navigate your next move: www.omaid.me/newsletter Follow me on LinkedIn: www.linkedin.com/in/omaidhomayun/

My guest today is Josh Panko, President of Leaf Trading Cards. Josh's journey in the sports card industry started at age seven when he opened a card shop in his basement. That childhood passion turned into a remarkable career that's taken him from working at card shops as a teenager, to Upper Deck's product development team, to now leading one of the most creative trading card companies in the industry. What I love about Josh's story is how he built his career by working every angle of the business—retail, distribution, manufacturing, customer service. He learned the entire supply chain, which gave him a perspective that few in the industry have. And today, at Leaf, he's creating some of the most innovative products in the space, from on-card autographs of Hollywood legends like Al Pacino and Clint Eastwood, to unique sports card concepts that major licensed manufacturers can't touch. This conversation is packed with wisdom on hard work, taking initiative, building relationships, and staying humble even as 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: Why working every level of your industry early in your career creates an unfair advantage - and how Josh's experience in retail, distribution, and manufacturing shaped his leadership at Leaf The handwritten letter strategy that landed Josh his dream job at Upper Deck - and why his father's unconventional advice to FedEx overnight it to the CEO actually worked How being kind to everyone (especially people outside your department) can fast-track your career - Josh's finance department friendships got his projects prioritized over senior colleagues Why Josh would rather employees take initiative and make mistakes than wait for permission - and the Shawshank Redemption lesson about not asking to go to the bathroom The "harder you work, the luckier you get" philosophy - and how Josh turned clocking out at 5pm then returning to work unpaid into career-defining opportunities 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/

Kendall Berg is a career strategist and author of Secrets of the Career Game who helps ambitious professionals navigate corporate politics with integrity and transform strong performance into visible, undeniable value. After being told early in her career that "everybody loves having you on their team, but nobody likes working with you," she dedicated herself to learning the unspoken rules of advancement—and was promoted five times in six years. Now, through her coaching practice and her tactical, no-nonsense approach, Kendall teaches thousands of clients across 27 countries how to earn more, advance faster, and feel in control of their career trajectory without burning out or losing themselves in the process. In this episode, you'll discover: Why your boss has NO idea what you're actually doing—and the weekly habit that fixes this blind spot The one person you must talk to during interviews that reveals the REAL company culture (hint: it's not the hiring manager) How asking for help makes people think MORE highly of you—the counterintuitive psychology that changes everything The "influencer list" strategy: Why you're networking with the wrong people and how to identify the 5 who actually control your career Why 82% of jobs are filled before they ever hit the job board—and what to do about it 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/  

Jamie Siminoff is the CEO and founder of Ring, the camera company that transformed home security. While his viral Shark Tank episode didn't yield a deal from the sharks, it launched the video doorbell company. In 2018, Ring sold to Amazon for $1 billion. Jame published a book titled Ding Dong: How Ring Went from Shark Tank Reject to Everyone's Front Door.  In this episode we discuss:  -the greatest lessons from his failures -the 1 question he'd ask James Dyson in an elevator -why often the most important decisions are the ones we say "no" to -how the best thing that never happened was not getting acquired by ADT -what he learned about the relationship between money and happiness -the best career advice he ever received -the nicest thing anyone has ever done for him and more -- go to www.omaid.me to sign up for the Career Compass newsletter where I share the best career advice from high achievers 

Patrick Mouratoglou is one of tennis's most successful and unconventional coaches, known for his work with Serena Williams during her dominant return to form—helping her win 10 Grand Slams and reclaim the world number one ranking. But his journey to the top began in the darkest of places: a childhood marked by crippling shyness, zero self-esteem, and such severe social anxiety that he couldn't make eye contact without fear of vomiting. When his dream of becoming a professional tennis player was crushed at 15, that rock bottom moment became the catalyst for an extraordinary transformation. Today, Patrick coaches the next generation of champions, founded the innovative Ultimate Tennis Showdown (UTS), and has written a book about the "progress zone"—the space where confidence is built through small, daily victories. His approach to coaching is refreshingly transparent in a sport known for secrecy, and his insights on building champions apply far beyond the tennis court. What You'll Learn in This Episode: Why the worst thing that happens to you might be the best thing—how Patrick's devastating rejection at 15 became the turning point that saved his life and launched his coaching career The hidden truth about motivation—why players (and people) who seem "unmotivated" are actually protecting their confidence, and what really drives elite performance How to rebuild someone's confidence from zero—Patrick's unconventional methods, including secretly rigging matches to create winning streaks and psychological breakthroughs What separates champions from great players—the mindset traits of Serena Williams, Roger Federer, and Novak Djokovic that have nothing to do with talent The art of hearing what people think, not just what they say—Patrick's most powerful coaching skill and why "the weather is nice" means completely different things in London versus Miami

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: How Bill McDermott's simple advice—"just be you"—freed Steve from a decade of self-doubt and changed his career trajectory The power of saying "no": How Steve took Marketo from $1.6B to $4.9B by doing less, not more Why talking to a customer every single day is non-negotiable and how it transforms your entire organization Turning adversity into strength: Steve's journey with type 1 diabetes and the moment that changed his perspective forever The future of AI in the workplace and why we're the last generation of managers to manage only humans

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      

Max Richter grew up in Stuttgart, Germany, surrounded by cameras—his father was a photographer with a Leica who ran an advertising business. After studying engineering and business, Max found himself restless in corporate life, eventually making his way to Shenzhen, China, where he met a campus legend named JK who had borrowed $2,000 from his father to start a camera company. What happened next was a decade-long journey of near-bankruptcy, pivotal pivots, and ultimately building Insta360 into a company that challenged GoPro and partnered with the very camera brand that filled Max's childhood home. Today, Max serves as a co-founder of Insta360, a company that's redefined how millions of people capture and share their lives. In this episode, you'll discover: The "dark year" of 2017 when Insta360 had over 100 employees, was running out of cash, and Samsung had just entered their market—and the unexpected user behavior that saved the company Why the moment you're closest to giving up is often the exact moment you need to push through, and how this principle turned a struggling startup into a company that makes $30+ million annually The career advice Max wishes he'd known at 25 about the dangers of overthinking and why "just starting" beats perfect planning every single time How immersing yourself in uncomfortable, foreign environments shapes you into a more open-minded person—and why Max believes traveling early is one of the most underrated career accelerators The sacrifices nobody talks about when building a global company, and why finding the intersection of passion, profit, and societal impact matters more than any single factor alone

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

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

Ariel Kaye is the founder and CEO of Parachute, the Los Angeles-based home essentials brand she launched in 2014. With no prior retail experience, Ariel transformed a simple observation about the lack of quality, non-toxic bedding into a multi-million dollar company that has redefined the direct-to-consumer home goods space. Before founding Parachute, she worked in marketing and media, experiences that proved invaluable in building a brand known for its storytelling and customer-centric approach. Today, Parachute operates retail stores across the country and has partnered with major retailers like Target, all while maintaining its mission of bringing comfort and quality into people's homes. In this episode we discuss: Why "I'll figure it out" is a legitimate business strategy – How embracing uncertainty and learning as you go can be more powerful than having all the answers upfront The transformative power of belief – How one friend's confidence in her abilities changed everything, and why believing in others (and telling them so) can literally change lives Why asking for help is your secret weapon – How to overcome the fear that not knowing everything makes you weak, and why the best leaders are the ones who know what they don't know How to handle rejection without losing momentum – Practical strategies for dealing with hundreds of "nos" from investors while staying focused on your vision The art of progress over perfection – Why small, consistent actions often matter more than grand gestures, especially for high achievers who get stuck in perfectionist cycles -- Check out the t-shirts for the podcast: https://www.bonfire.com/to-the-top-4/    

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.

In this episode, I sit down with Tim Bantle, President of heritage brand Filson and the former Patagonia executive who helped transform a $200 million company into a billion-dollar global powerhouse. From his philosophy degree to building some of the outdoor industry's most iconic products like the Nano Puff, Tim shares the unconventional path that led him to the top of two legendary American brands. You'll discover why he doesn't have a resume, how a family crisis became his greatest career opportunity, and the simple advice from his optician father that shaped his entire approach to business. Tim reveals the leadership strategies that actually work—from asking questions for six months before making changes to why authenticity is your ultimate competitive advantage. Whether you're climbing the corporate ladder or building your own business, this conversation is packed with practical wisdom from someone who's actually done it. What We Discussed: From Philosophy Student to Outdoor Industry Leader - How Tim's unconventional academic background in philosophy and literature led to a career building billion-dollar outdoor brands, and why his father jokingly told other parents to have their kids "just study philosophy" The Product Innovations That Changed Everything - The inside story of creating Patagonia's breakthrough products like the Down Sweater and Nano Puff, including how a failed fleece project accidentally revolutionized down insulation and became a billion-dollar product line How Family Crisis Became Career Catalyst - Why having a special needs child and his wife leaving her career actually freed Tim to pursue global opportunities, leading to roles across California, Utah, Europe, and Canada Leadership Without a Playbook - Tim's approach to taking over heritage brand Filson, why he spends six months asking questions before making changes, and how he avoids the trap of bringing solutions from previous companies The Network Effect and Authentic Success - Why Tim doesn't have a resume, how every job opportunity came through relationships, and his philosophy that being the best version of yourself is the key to finding the right opportunities

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 Fail Sara'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 Path Sara 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 Education When 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 Advantage Sara'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-Making Having 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.  

Sam Vander Wielen is the founder of a multimillion-dollar legal templates business and author of "When I Start My Business I'll Be Happy: A Practical, No-BS Guide to Successful Online Entrepreneurship." As a former corporate attorney turned entrepreneur, Sam provides legal templates and education to online business owners, helping them protect themselves and their businesses without the anxiety or expense of hiring a lawyer. After pivoting from a brief stint as a health coach, Sam discovered her niche when fellow entrepreneurs kept asking her legal questions at a wellness conference. Today, her signature product, the Ultimate Bundle, has generated over $8 million in revenue, while her weekly newsletter "Sam's Sidebar" reaches more than 47,000 subscribers. In this episode, you'll learn how Sam discovered her multimillion-dollar business idea by listening to her audience at a wellness festival, where people lined up for legal advice instead of health coaching You'll discover why Sam believes starting with a viable business concept is more important than just "following your passion" and how differentiation beats trying to be better than competitors You'll hear about Sam's ingenious "broccoli and mac and cheese strategy" that helped her grow an email list of 47,000 subscribers by balancing necessary legal content with topics people actually want to consume This conversation reveals why Sam intentionally keeps her business streamlined around one core offering (her "Ultimate Bundle") rather than constantly expanding - and how this approach supports both profitability and work-life balance You'll understand the central message behind Sam's book title "When I Start My Business I'll Be Happy" as she challenges the "when-then" mindset and explains why external success doesn't automatically bring happiness

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: How values create freedom - Gary explains his hierarchical value system that empowered employees to make independent decisions anywhere in the world without "quacking up the hierarchy." Embracing "learning moments" rather than failures - Learn how reframing mistakes revolutionized WD-40's culture and encouraged innovation without fear. The ego-empathy balance - Discover why letting "empathy eat your ego" instead of the reverse is crucial for effective leadership. The power of authentic humility - Gary shares his mother's wisdom: "Even the Queen sits down to pee" and how staying grounded shaped his leadership style. Why "coach" should replace "manager" - Understand the fundamental difference between managing and coaching that transformed WD-40's organizational structure. The "Maniac Pledge" for accountability - Learn about Gary's antidote to the "Na-Na-Na Disease" of finger-pointing that builds true responsibility. Not ignoring your "alarm bells" - A personal story illustrates the importance of paying attention to warning signs in both business and life. 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.

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..

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: Why breaking free from "default programming" is essential for creating a life you won't regret How to identify your unique "superpowers" and leverage them for greater career fulfillment The critical transition from an achievement mindset to a contentment mindset without losing your ambition Why making counterintuitive life choices—like moving next door to your best friends—can lead to deeper happiness than following the traditional script

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: How to Listen Beyond Words - Discover techniques to understand the emotions and unspoken needs hiding beneath surface-level conversation. When to Switch Listening Modes - Learn to identify your default listening style and how to adapt it based on what others actually need from you. Turning Any Topic Into an Engaging Conversation - Find out how to remain genuinely curious about subjects that don't naturally interest you by focusing on the person sharing them. Setting Healthy Boundaries While Listening - Master the balance between empathetic listening and protecting yourself from carrying others' emotional burdens. The Power of Being Fully Present - Understand how mindfulness, reduced note-taking, and self-awareness create the foundation for meaningful connections. -- email questions to omaid@omaid.me

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: How focusing on the only two things you can truly control—attitude and effort—can transform your approach to challenges in both work and life. Why consistent leadership creates trust, and how showing up the same way every day (like Pete Carroll did) makes it easier for people to follow you. The importance of not letting external achievements define your worth, and how Jeff's career-threatening injuries helped him realize "football doesn't define me, I define me." When to prioritize mission over money, demonstrated by Jeff's decision to pull a profitable product that didn't meet his company's standards. Why embracing personal evolution is essential, and how giving yourself permission to reinvent yourself every 6-12 months creates space for growth..and more -- email questions to omaid@omaid.me