To The Top: Inspirational Career Advice

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

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 mea

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 vi

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 a

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 pr

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

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 skil

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:  How to spot and execute on a market gap: See how they identified the need for affordable premium knives and built a business around it Why opposing skills can create perfect partnerships: Discover how a philosophy major and a business graduate complemented each other to build a national brand How to disrupt a traditional industry: Learn their strategies for challenging established norms and introducing innovative designs that competitors now copy The power of patient networking: Understand how they built retail partnerships over years, not months, expanding from a garage to 10,000+ stores How to scale while staying lean: See how they grew t

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 y

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.

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

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

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

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

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

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

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

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