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

div]:bg-bg-000/50 [&_pre>div]:border-0.5 [&_pre>div]:border-border-400 [&_.ignore-pre-bg>div]:bg-transparent [&_.standard-markdown_:is(p,blockquote,h1,h2,h3,h4,h5,h6)]:pl-2 [&_.standard-markdown_:is(p,blockquote,ul,ol,h1,h2,h3,h4,h5,h6)]:pr-8 [&_.progressive-markdown_:is(p,blockquote,h1,h2,h3,h4,h5,h6)]:pl-2 [&_.progressive-markdown_:is(p,blockquote,ul,ol,h1,h2,h3,h4,h5,h6)]:pr-8"> _*]:min-w-0 standard-markdown"> 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