Doug Melville interviews Amman Ahmed, founder of the Youtube channel Music for Pets (Relax My Dog/Relax My Cat). He shares his vision about the confidence needed to believe in your unconventional ideas, and learning through experimentation. Ahmed describes growing up in Armley, Leeds, finding hope through books, studying IT, and realizing corporate life wasn’t for him after reading Tim Ferriss’ The 4-Hour Workweek. He started a YouTube-based relaxation music channel with $1000 and later expanded into pet-focused music and “dog TV” visuals, using insights about instruments, BPMs, frequencies, and color grading to help pets with anxiety and stress. After being pushed out of a VC-backed music discovery startup, he recommitted to bootstrapping, scaled a highly profitable business with multiple revenue streams, and sold it for in 2023 for ten figures after turning down earlier offers. He now stays in music, angel invests, and campaigns a new age album, “Ekta,” for Grammy consideration.

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This week, Doug answers a listener question from Jasmine in Washington, D.C. about breaking into the luxury industry. He explains that luxury has distinct culture and philosophy from fashion and operates within an unwritten hierarchy. He shares five tips for getting your foot in the luxury door, including that the hiring process can take up to a year.

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Everyone is talking about AI—but are you actually getting better at using it?

In this mailbag episode of DM Me with Doug Melville, Doug answers a listener who wants to improve their AI skills but doesn’t know where to start. His answer: create your own AI Fingerprint.

An AI Fingerprint is the unique process you develop for using AI to think, research, create and make decisions. Doug breaks down how to build yours—from defining the problem and choosing the right AI platform, to refining prompts, comparing outputs across different models and adding the one ingredient AI can’t replicate: your own judgment, experience and point of view.

You don’t need to become an AI expert. But in a workplace increasingly shaped by AI, you do need to understand how you work with it.

AI literacy may soon matter as much as knowing how to use email, PowerPoint or Google - and the leaders who develop their own process now could have an advantage later.

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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 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 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 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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