Big Shot

In this special episode of Big Shot, recorded live at the iconic Kennedy Center in Washington, D.C., we’re joined by Uri Levine, the co-founder of Waze. Uri is a visionary entrepreneur whose journey includes building Waze, the world’s largest community-based traffic and navigation app, which Google acquired for over $1 billion. Beyond Waze, Uri has co-founded several impactful startups like Moovit (acquired by Intel), FeeX, and Engie. He’s also the author of Fall in Love with the Problem, Not the Solution, a must-read guide for entrepreneurs. In our conversation today, we cover: • Lessons on failure and prioritization from Uri’s father • A clever hack he used to pitch Waze with an incomplete product • The cultural drive behind the Jewish ambition to create positive change • The story of the many millionaires created by Waze’s acquisition • And so much more! A special thank you to ADL In Concert Against Hate. You can learn more here https://www.adl.org/adl-concert-against-hate-shines-light-heroes — In This Episode We Cover: (00:00) Intro (01:40) How Uri’s father taught him the importance of failure (04:55) A story about prioritization (06:59) Uri’s solution for fundraising with an incomplete product (09:00) The ups and downs of the start-up journey (11:04) Why Jewish people are drawn to entrepreneurship and making a positive impact (12:58) The connection between the kibbutz community and entrepreneurship (13:25) The Google acquisition of Waze (13:58) The importance of keeping the main thing the main thing (15:11) How tikkun olam inspires Uri’s entrepreneurial ventures (16:48) Chutzpah and the Israeli experience (17:40) How Uri continues to be inspired by his father — Where To Find Uri Levine: • Website: https://urilevine.com/ • LinkedIn: https://www.linkedin.com/in/uri-levine/ • X: https://x.com/urilevine1 — Where to Find ADL: • Website: https://www.adl.org/ — Where To Find Big Shot: • Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.bigshot.show/⁠⁠⁠⁠⁠⁠⁠⁠ • YouTube: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@bigshotpodcast⁠⁠⁠⁠⁠⁠⁠⁠⁠ • TikTok: ⁠⁠⁠⁠⁠⁠⁠⁠https://www.tiktok.com/@bigshotshow⁠⁠⁠⁠⁠⁠⁠⁠ • Instagram: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/bigshotshow/⁠⁠⁠⁠⁠⁠⁠⁠⁠ • Harley Finkelstein: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://twitter.com/harleyf⁠⁠⁠⁠⁠⁠⁠⁠⁠ • David Segal: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://twitter.com/tea_maverick⁠⁠⁠⁠⁠⁠⁠⁠⁠ • Production and Marketing: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co⁠

In today’s episode of Big Shot, we’re joined by retail legend Mickey Drexler, whose transformative leadership reshaped some of the biggest names in fashion. Over his 18-year tenure at The Gap, Mickey took the company from $400 million to $14 billion in revenue, revolutionizing casual wear and spotting a new retail opportunity that led to the creation of Old Navy. His influence extends far beyond The Gap—he also founded Madewell, served on Apple’s board for over a decade, and now works alongside his son Alex on the growing success of Alex Mill. In our conversation today, we cover: Mickey’s humble beginnings in a one-bedroom apartment in The Bronx Mickey’s heuristic for hiring and what draws him to people Mickey’s friendship with Steve Jobs and what it was like serving on each other’s boards The importance of urgency and why a bad decision is better than indecision How Mickey does market research, and his process behind both The Gap and Old Navy Mickey’s thoughts on entrepreneurship, his family, and much more! — In This Episode We Cover: (02:53) Welcome Mickey Drexler (03:29) Mickey’s childhood in the Bronx (12:40) The traits Mickey looks for in people he’s hiring (14:56) Why Mickey values kindness and treating others fairly, regardless of their status (16:40) Why the best training is doing the job (18:40) Mickey’s high standards, obsession with data, and the importance of instinct (28:39) How Steve Jobs persuaded Mickey to join Apple’s board (32:33) What Mickey admired about Steve Jobs (34:20) Why a bad decision is better than indecision (36:34) What makes a great website (39:43) Mickey’s process for helping The Gap standout (46:32) Why Mickey calls the fashion business a commodity business (47:20) How Dayton Hudson’s Target stores inspired Mickey to build Old Navy (54:15) How Mickey got the name for Old Navy (57:42) The challenges Mickey faced opening Old Navy (1:00:20) How the meaning of value depends on the individual customer (1:05:29) The call from Steve Jobs that marked an end to Mickey’s time at The Gap (1:11:20) Mickey’s wife, Peggy’s background (1:13:22) Mickey’s experience taking J. Crew private (1:18:17) How Mickey balances work and family (1:20:03) Mickey’s thoughts on Jewish entrepreneurship, especially in the fashion industry (1:21:52) Mickey’s parting advice on learning entrepreneurship thoughts on school (1:23:37) What David learned at school, and Harley’s learnings from Mickey Where To Find Mickey Drexler • X: https://twitter.com/millarddrexler • Instagram: https://www.instagram.com/mickeydrexler • LinkedIn: https://www.linkedin.com/in/millard-mickey-drexler-1b00a9269/ Where To Find Big Shot: • Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.bigshot.show/⁠⁠⁠⁠⁠⁠ • YouTube: ⁠⁠⁠⁠⁠⁠⁠https://www.youtube.com/@bigshotpodcast⁠⁠⁠⁠⁠⁠⁠ • TikTok: ⁠⁠⁠⁠⁠⁠https://www.tiktok.com/@bigshotshow⁠⁠⁠⁠⁠⁠ • Instagram: ⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/bigshotshow/⁠⁠⁠⁠⁠⁠⁠ • Harley Finkelstein: ⁠⁠⁠⁠⁠⁠⁠https://twitter.com/harleyf⁠⁠⁠⁠⁠⁠⁠ • David Segal: ⁠⁠⁠⁠⁠⁠⁠https://twitter.com/tea_maverick⁠⁠⁠⁠⁠⁠⁠ • Production and Marketing: ⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co⁠

Harley Finkelstein and David Segal are back with Season 3 of Big Shot! Today, we chat with beauty industry icon Bobbi Brown. Known for her work as a makeup artist, Bobbi’s expertise has been showcased on the covers of leading magazines, including Cosmopolitan, Allure, Mademoiselle, and Teen. She’s the author of nine beauty books, with five achieving bestseller status. In 1991, Bobbi founded Bobbi Brown Cosmetics, which Estée Lauder acquired for $74.5 million four years later. Bobbi had a 25-year non-compete with Estée Lauder, and as soon as that expired, she launched her latest company, a clean beauty brand called Jones Road. In our conversation, we discuss the following: How chutzpah and optimism landed Bobbi her first Vogue cover How Bobbi developed her first lipstick and the original ten that became the brand’s foundation. How organic networking was a big part of Bobbi’s success The Estée Lauder acquisition of Bobbi Brown Cosmetics and Bobbi’s friendship with Leonard Lauder How Bobbi prioritized motherhood over work Life after the non-compete: Her new partnerships and Jones Road And so much more — In This Episode We Cover: (04:28) How Bobbi got started by cold-calling models and agencies (10:30) How Bobbi learned entrepreneurship skills at Emerson (12:52) Bobbi’s first lipstick and the beginnings of her makeup empire (17:39) The Bergdorf Goodman deal that almost fell apart (21:30) A chance encounter in an elevator that led Bobbi to her second chemist (22:10) Meeting Jeff Zucker’s grandmother and landing a regular spot on The Today Show (26:15) Trailblazing the natural makeup movement (34:10) Bobbi’s meeting with Leonard Lauder of Estée Lauder (35:59) How Bobbi was able to prioritize her kids (39:20) The sale to Estée Lauder (42:54) How Bobbi celebrated and shared her wealth with her family (43:45) The first freestanding store, and how Leonard Lauder supported Bobbi (47:00) The decline of Bobbi’s relationship with Estée Lauder that led to her leaving (51:30) The Just Bobbi curated collection at Lord and Taylor (53:30) How Bobbi moved on from the drama at Estée Lauder (1:00:01) Launching Jones Road (1:08:55) Miracle Balm’s instant popularity (1:10:20) Bobbi’s response to a TikTok influencer trashing her foundation (1:13:43) Bobbi’s thoughts on selling her new company (1:14:45) Bobbi’s partnership with her son, Cody (1:17:03) New learnings at Jones Road (1:18:28) Bobbi’s thoughts on chutzpah (1:19:25) Bobbi’s perspective on health and longevity (1:20:36) What being Jewish means to Bobbi (1:23:15) The secret to Bobbi’s successful marriage and partnership — Where to find Bobbi Brown: X: https://x.com/justbobbibrown Instagram: https://www.instagram.com/justbobbidotcom Facebook: https://www.facebook.com/JustBobbiDotCom TikTok: https://www.tiktok.com/@justbobbibrown Where To Find Big Shot: Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.bigshot.show/⁠⁠⁠⁠ YouTube: ⁠⁠⁠⁠⁠https://www.youtube.com/@bigshotpodcast⁠⁠⁠⁠⁠ TikTok: ⁠⁠⁠⁠https://www.tiktok.com/@bigshotshow⁠⁠⁠⁠ Instagram: ⁠⁠⁠⁠⁠https://www.instagram.com/bigshotshow/⁠⁠⁠⁠⁠ Harley Finkelstein: ⁠⁠⁠⁠⁠https://twitter.com/harleyf⁠⁠⁠⁠⁠ David Segal: ⁠⁠⁠⁠⁠https://twitter.com/tea_maverick⁠⁠⁠⁠⁠ Production and Marketing: ⁠⁠⁠⁠⁠⁠https://penname.co⁠

When you think about a "convenience store manager," you probably don't imagine a future billionaire. But that's exactly the path Ron Shaich took from humble beginners selling Tollhouse cookies to a $7.5 billion restaurant empire. In this episode of Big Shot, Harley Finkelstein and David Segal welcome Shaich, the founder of Panera Bread, who shares his incredible journey from a nonprofit convenience store to his pivotal decision to create Panera Bread. Ron is a master at finding the trends others can't see before becoming popular. He shares the challenges and successes that defined his path, highlighting the power of adaptability and innovation. And breaks down the difference between risk-taking and risk-avoidance, and how leaning into one over the other can lead to incredible success. The episode is filled with incredible takeaways, including: How Ron has the best-performing restaurant stock of all time (44x return compared to the S&P 500) Why his first store in college was a spite store What he learned from his IPO with Au Bon Pain How he created an entirely new category, “Fast Casual” And so much more — In This Episode We Cover: (02:35) Ron’s early years growing up in New Jersey in a family of left-wing political activists (07:50) Ron’s gap year working for a congressman (09:45) How a false accusation of shoplifting prompted Ron to open a convenience store (14:50) How Ron fell in love with business and his time at Harvard Business School (19:28) The rewards of entrepreneurship (20:40) What business has in common with politics (23:22) How Ron made money selling flea collars in college (26:00) Why Ron got his inheritance early (27:35) Ron’s work in DC as President of Targeting Systems (29:08) How Ron opened The Cookie Jar in Boston (31:43) Ron’s partnership with Au Bon Pain’s founder, Louis Kane (39:44) Ron and Louis’s exceptional friendship and partnership (42:25) The importance of empathy and the insights that it brought Ron (48:35) How Ron created a brand new category, bakery cafe (51:50) How Ron felt right before Au Bon Pain’s IPO (53:00) The downsides of going public (54:50) Ron’s means, ends, and by-products framework (57:20) What Ron learned from watching his parents face death (1:00:13) How Ron organized his life (1:03:35) Ron’s purchase of the St. Louis Bread Company (1:07:28) How Ron’s trend studying led him to fast casual dining (1:13:52) The transformation of St. Louis Bread into Panera (1:15:33) Why Ron decided to sell Au Bon Pain to focus on Panera (1:20:25) The rapid growth stage of Panera (1:22:51) Ron’s philanthropy with No Labels and Panera Cares (1:25:14) The painful journey of transforming Panera (1:32:09) Thoughts on success, chutzpah, and the Jewish entrepreneurial spirit (1:34:28) Why entrepreneurs are risk avoiders (1:35:34) Why Ron sees building organizations as a way to impact the world positively (1:37:44) Ron’s investment company, Act 3, and the problem with short-termism — Where to find Ron Shaich: Website: ⁠https://www.ronshaich.com/⁠ LinkedIn: https://www.linkedin.com/in/ronshaich/ X: https://x.com/shaich Facebook: https://www.facebook.com/shaich Where To Find Big Shot: Website: ⁠⁠⁠⁠⁠⁠⁠https://www.bigshot.show/⁠⁠ YouTube: ⁠⁠⁠https://www.youtube.com/@bigshotpodcast⁠⁠⁠ TikTok: ⁠⁠https://www.tiktok.com/@bigshotshow⁠⁠ Instagram: ⁠⁠⁠https://www.instagram.com/bigshotshow/⁠⁠⁠ Harley Finkelstein: ⁠⁠⁠https://twitter.com/harleyf⁠⁠⁠ David Segal: ⁠⁠⁠https://twitter.com/tea_maverick⁠⁠⁠ Production and Marketing: ⁠⁠⁠⁠https://penname.co⁠

In this episode of Big Shot, we sit down with another legendary real estate developer, Larry Silverstein. Best known for the 99-year lease he signed for the World Trade Center, just six weeks before 9/11, Larry’s story is one of persistence and strategic partnerships—and a whole lot of chutzpah. He shares with us today how he leveraged partnerships, refurbished properties on a shoestring budget and built a business that today is valued at over $10 billion. As with many successful Jewish entrepreneurs, family is at the center of it all, and Larry speaks with extreme gratitude about his children and wife Klara. You won’t want to miss hearing about how Larry very narrowly missed being at ground zero during 9/11, and how his wife supported his efforts in rebuilding the World Trade Center. If you'd like to apply to be an executive producer, please complete the form here https://shorturl.at/xLQUW In This Episode We Cover: (03:19) How Larry got established in real estate with no money (09:59) Why Larry turned down a 100k profit on his first contract (12:51) How Larry leveraged investors to land million-dollar properties (14:22) The low-budget, resourceful way Larry’s team refurbished buildings (16:31) How Larry collaborated with competitors in purchasing 711 Fifth Avenue (24:42) Coca-Cola’s purchase of 711 Fifth Avenue (26:43) Why Larry worked with partners (27:33) The beginning of Larry’s journey toward buying the World Trade Center (35:22) How Silverstein Properties built their own electric plant (45:28) The drama of signing Salomon Brothers (52:44) Larry’s accident and acquiring the World Trade Center (58:45) Why Larry was absent from the building on 9/11 (1:00:20) How Larry decided to rebuild the World Trade Center (1:04:21) When Larry knew he made it (1:06:28) Larry’s philanthropic efforts paying the tuition of medical school students — Referenced: Harry Helmsley: https://en.wikipedia.org/wiki/Harry_Helmsley 711 Fifth Avenue Purchased from Columbia Pictures: https://www.nytimes.com/1978/04/23/archives/realty-news-fifth-avenue-third-avenue-executives-named.html George Kaufman’s obituary: https://www.nytimes.com/2018/02/26/obituaries/george-s-kaufman-who-revived-astoria-studios-dies-at-89.html Peter Feinberg obituary: https://www.nytimes.com/1990/03/15/obituaries/peter-i-feinberg-79-real-estate-developer.html Port Authority to lease World Trade Center to Silverstein Properties: https://www.panynj.gov/port-authority/en/press-room/press-release-archives/2001_press_releases/port_authority_toleaseworldtradecentertosilversteinpropertiesinc.html World Trade Center history: https://www.911memorial.org/learn/resources/digital-exhibitions/world-trade-center-history Ed Koch: https://en.wikipedia.org/wiki/Ed_Koch Salomon Brothers: https://en.wikipedia.org/wiki/Salomon_Brothers Mortimer Zuckerman: https://en.wikipedia.org/wiki/Mortimer_Zuckerman Salomon Will Move to the World Trade Center: https://www.nytimes.com/1988/11/29/nyregion/salomon-will-move-to-trade-center.html The Collapse of Drexel Burnham Lambert: https://www.nytimes.com/1990/02/14/business/the-collapse-of-drexel-burnham-lambert-key-events-for-drexel-burnham-lambert.html NYU School of Medicine Offers Full-Tuition Scholarships to All New & Current Medical Students: https://nyulangone.org/news/nyu-school-medicine-offers-full-tuition-scholarships-all-new-current-medical-students — Where to find Larry Silverstein: Silverstein Properties: https://www.silversteinproperties.com/ The Rising: The Twenty-Year Battle to Rebuild the World Trade Center: https://www.amazon.com/Rising-Twenty-Year-Battle-Rebuild-Center/dp/0525658963 Where To Find Big Shot: Website: ⁠https://www.bigshot.show/ YouTube: ⁠https://www.youtube.com/@bigshotpodcast⁠ TikTok: https://www.tiktok.com/@bigshotshow⁠ Instagram: ⁠https://www.instagram.com/bigshotshow/⁠ Harley Finkelstein: ⁠https://twitter.com/harleyf⁠ David Segal: ⁠https://twitter.com/tea_maverick⁠ Production and Marketing: ⁠⁠https://penname.co

In this episode of Big Shot, we're thrilled to welcome the incredible David Rubenstein! As a co-founder of The Carlyle Group, one of the globe's top private equity firms, David's journey from a Baltimore kid with big dreams to a presidential advisor and business mogul is truly inspiring. Join us, as David reveals how he overcame rejection after President Carter lost his re-election and pivoted into private equity. Learn why he's dedicated to giving back through initiatives like the Giving Pledge, and get ready for some thought-provoking insights, including why hiring geniuses might not be the best idea and tips on avoiding spoiling your kids. In This Episode We Cover: (03:40) Welcome David Rubenstein (04:50) Why David and Harley both maintain their bar memberships (05:37) Why education is important to the Jewish people (07:30) David’s upbringing in Baltimore (10:00) The difficulties that come with raising children when you’re wealthy (11:30) David’s relatively laid-back parents (13:34) The Jewish youth group that fueled David’s drive for more (14:15) David’s first job out of law school (15:25) How David became an advisor to President Jimmy Carter (16:42) The years of struggle after Jimmy Carter failed to get re-elected (20:41) How the Carlyle Group got their start (24:36) Carlyle’s “bear hug” on Chichi’s (27:22) David’s growth strategy for Carlyle focusing on diversification and globalization (31:30) David’s mom’s philanthropy (34:14) What the Giving Pledge is (36:43) David’s philosophy on philanthropy (39:33) An explanation of the Magna Carta, its failure, and the anti-semitism of the day (42:22) David’s focus on patriotic philanthropy (46:47) How David became the fundraiser for Carlyle (47:56) How Carlyle was able to build a lasting company (49:27) Why reasonably intelligent people make better employees than geniuses (50:04) The cultural values that make Jewish people successful and want to give back (54:10) Antisemitism in the US and Europe (54:28) Why David still doesn’t think he’s made it (55:33) Tips on raising kids and the three ways to influence people as a leader — Referenced: David Rubenstein on Patriotic Philanthropy: https://www.whitehousehistory.org/the-white-house-1600-sessions/david-rubenstein-on-patriotic-philanthropy Shelley v. Kraemer: https://en.wikipedia.org/wiki/Shelley_v._Kraemer Virtual Jewish World: Baltimore, Maryland: https://www.jewishvirtuallibrary.org/baltimore-jewish-history-tour#google_vignette Paul, Weiss, Rifkind, Wharton & Garrison LLP: https://www.paulweiss.com/ Ted Sorensen: https://en.wikipedia.org/wiki/Ted_Sorensen William Simon: https://www.philanthropyroundtable.org/hall-of-fame/william-simon/ G. William Miller: https://home.treasury.gov/about/history/prior-secretaries/g-william-miller-1979-1981 Edward J. Mathias: https://www.carlyle.com/corporate-overview/operating-executives-advisors/edward-j-mathias T. Rowe Price: https://www.troweprice.com/ The Mellon family: https://www.forbes.com/profile/mellon/?sh=21c04b3f6c8b Greenmailing: https://www.investopedia.com/terms/g/greenmail. Mike Milken: https://milkeninstitute.org/staff/mike-milken Frank Carlucci: https://en.wikipedia.org/wiki/Frank_Carlucci John Major: https://www.britannica.com/biography/John-Major Why are there so many Jewish Nobel winners?: https://www.thejc.com/lets-talk/why-are-there-so-many-jewish-nobel-winners-ctycke48# — Where to find David Rubenstein X: https://twitter.com/DM_Rubenstein Website: https://davidrubenstein.com/ Where To Find Big Shot: Website: ⁠https://www.bigshot.show/ YouTube: ⁠https://www.youtube.com/@bigshotpodcast⁠ TikTok: https://www.tiktok.com/@bigshotshow⁠ Instagram: ⁠https://www.instagram.com/bigshotshow/⁠ Harley Finkelstein: ⁠https://twitter.com/harleyf⁠ David Segal: ⁠https://twitter.com/tea_maverick⁠ Production and Marketing: ⁠⁠https://penname.co