#112 Sara Sugarman: Empathy is Your Competitive Advantage
To The Top: Inspirational Career Advice
Release Date: 05/22/2025
To The Top: Inspirational Career Advice
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...
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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...
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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....
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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...
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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"...
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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...
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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
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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
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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...
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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...
info_outlineSara 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.