Doug answers a mailbag question from Janelle, a New York City professional who lost her corporate job and is struggling to find a new full-time role in this brutal job market. Sharing five practical tips drawn from his Stanford GSB reputation management teaching, Doug emphasizes that reputation precedes you, urging a Google first-page audit, and considering private social media settings. He notes that “ghost jobs” are on the rise, and with them, the rising importance of referrals. Doug advises proactively activating your network and understanding whether you’re in the “tennis” or “golf” phase of a career.

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This week, Doug Melville interviews Nancy Reyes, president and CEO of BBDO Worldwide about creativity in a corporate environment, leadership in an age of AI, and the evolving role of the C-suite. Reyes argues creativity isn’t an output, but a way of thinking and problem-solving that must be “zoned upstream” to address the biggest business problems, not just pushed into transactional work. They discuss the increased visibility of entrepreneurs and influencers, hiring for hustle and curiosity, and defining influence as opinion that carries weight.

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Doug talks with longtime friend Andrew “Andy” Hilfiger about building culture at the intersection of fashion and music, from early retail lessons with his older brother Tommy Hilfiger, to creating Tommy Jeans, and his own brand, Andrew Charles. Andy recounts key moments in his career, including styling hip-hop and R&B artists, launching iconic campaigns with Aaliyah, and how Snoop Dogg ended up wearing his designs on Saturday Night Live. He tells Doug about launching J.Lo by Jennifer Lopez, and remembers where he first met Doug... on Britney Spears' Baby One More Time tour. Andy shares advice on how to start your career in the fashion industry and reflects on changes driven by e-commerce and fast fashion in recent decades.

For more of Andy Hilfiger:

Andy's Instagram

www.AndrewCharles.com

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Original Publish May 26, 2026

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Today on DM Me, Doug interviews Artis Stevens, CEO of Big Brothers Big Sisters of America, about scaling mentorship through group and workplace programs...including momentum supported by a $122.5 million MacKenzie Scott donation! Artis describes the act of mentorship as a practice coded in human DNA that should be intentional and reciprocal. He explains BBBS’s 120-year origins as an alternative to the juvenile justice system and its reach across over 5,000 communities. They get into misconceptions about the time commitment for "Bigs", and explains how the matches are made, and why early interactions can feel rocky, but often become long-term. The conversation even touches on corporate mentorship, and how that can make a true difference for someone who may not have a way to advance the corporate ladder otherwise.

More of Artis:

Instagram

Artis on the Daily Show with Josh Johnson

BBBS Website

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Doug welcomes freelance journalist Alyson Krueger, who has written thousands of pieces for outlets including The New York Times, and recently launched the widely acclaimed Substack The Great Conversation. They discuss what modern journalism has become, how freelancing works through pitching and editor assignments, and how voice and objectivity differ across publications, and versus Substack’s unfiltered, direct-to-reader model. Alyson shares her path from international relations and events in London to NYU journalism school, and selling her early Times pieces through networking, coachability, and charisma.

More of Alyson:

New York Times

The Great Conversation on Substack

Instagram

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Doug hosts a mailbag episode explaining how to pivot from a corporate career to becoming a published author, answering listener questions about his path to writing Invisible Generals with Simon & Schuster. He stresses understanding the marketplace and your niche category, avoiding memoirs without name recognition, choosing a story you’re uniquely positioned to tell, and constructing a realistic marketing plan focused on selling tens of thousands of copies. He outlines using AI for research and editing but not to write the book or proposal and recommends hiring a book proposal writer and securing a literary agent to pitch the "Big Five" publishers.

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Doug interviews Emmanuel Waters, CEO and co-founder of Durham, North Carolina-based Old Hillside Bourbon Company. Launched in 2020 and expanding across the U.S., Emmanuel shares his pivot from a Department of Defense and contracting career to entrepreneurship after a COVID-era “aha moment”. He talks about breaking a state sales record at launch, but not before planning his career exit with his wife by reviewing finances, relying on benefits, and reviewing the spirits industry’s regulation and low margins. Old Hillside’s differentiation is storytelling, using nontraditional packaging and on-bottle narratives to honor Black American history, including early Kentucky Derby Black jockeys and the Trifecta women of horse racing. Emmanuel and Doug discuss product persistence in the spirit market, capital access challenges, celebrity liquor brands, being lumped with other Black-owned labels, and advice on chasing purpose over money.

More of Emmanuel:

Old Hillside Website

Forbes Article

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@DougMelville

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Doug interviews Allison Kluger, a Stanford Graduate School of Business professor who teaches courses on reputation management, strategic communication, personal branding, and strategic pivoting. Kluger shares her AIM framework (audience, intent, message), discusses how Google and LinkedIn shape first impressions, and distinguishes visibility from credibility by emphasizing trust and front facing acts of service. She highlights the outsized impact of first impressions and outlines the “trust radar” for crisis recovery, using Will Smith’s 2022 Oscars incident as an example. Allison and Doug also discuss career pivots through transferable skills, the risks of AI-amplified misinformation, and using personal "feedback surveys" to identify the traits people most associate with you.

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@DougMelville

www.DougMelville.com

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