Today we talk to Cindy Gallop, a big-wheeling ad exec from Manhattan that’s worked with the world’s largest brands. Business Insider named her one of the 15 Most Important Marketing Strategists, alongside Malcolm Gladwell and Seth Godin, and #1 on their list of Top 30 People In Advertising. She’s basically Don Draper from MadMen.
Cindy is known for blowing shit up, and her latest target? Sex. As an older woman who loves dating younger men, she was tired of teaching men that had grown up watching porn how real sex works. She launched Make Love Not Porn as a safe place where you can go to see real people having real sex ,in all its silly, messy, beautiful humanness. I’ve done my research and yes - it’s sweaty, saggy, awkward and it feels, well..doable. But it hasn’t been easy. She talks about the structural, cultural and financial obstacles she’s had to overcome, and how she’s used people’s skepticism to fuel her mantra - “I’ll fucking well show you.”
I was also dying to talk to Cindy about her life before MLNP because the things she’s done are exactly the things I struggle with every day. Cindy talks to us about our personal brand, and how to control what people are saying about us when we’re not in the room. She talks about the cure for ageism, and how we can build the confidence we need to do and say whatever we want, without worrying what anyone thinks.
Maybe you’re struggling to figure out your superpower. Maybe you’re concerned about your kids having a healthier relationship with sex. Or maybe you’re just tired of men asking if they can come on your face. Whatever it is, this episode is for you.
Please enjoy Cindy Gallop.
Key Takeaways
The “Michael Bay of Business”: Cindy’s tagline came from a spontaneous moment, but it stuck because it perfectly captured how she helps people and brands radically reinvent themselves by blowing up the status quo.
Finding Your Tagline: We all have a “default throwaway descriptor” — how others describe us when we’re not in the room. Cindy shares how to take ownership of that narrative to build a personal brand that truly reflects who you are.
Confidence Through Values: The key to confidence isn’t “finding your purpose,” it’s identifying your values and making sure you’re living in alignment with them — every day.
Curiosity Over Crisis: When you’re unsure about your next move in life or career, don’t chase a big purpose. Start by doing interesting things, following your curiosity, and letting the path unfold from there.
Say Your Age: Cindy is on a mission to combat ageism by loudly and proudly saying her age (65) — and encouraging others to do the same. Your age is the sum total of your wisdom, experience, and value.
Revolutionizing Sex Ed: Through Make Love Not Porn, Cindy is offering an alternative to porn-as-sex-ed by showcasing real-world, loving, consensual sex — and she’s now building MakeLoveNotPorn.academy to become the Khan Academy of sex education.
Why Men Are Crying (in a Good Way): Many men have written to Cindy saying they cried after watching their first Make Love Not Porn video. It’s a space where men can see vulnerability, intimacy, and emotional connection modeled in a way they’ve never seen before.
The Opposite of Andrew Tate: With Make Love Not Porn, Cindy is quietly dismantling toxic masculinity — showing young men a new model built on empathy, love, and real connection.
The Power of Doing What Everyone Else Says You Can’t: After 16 years of roadblocks from banks, tech platforms, and investors, Cindy is still here. Why? Because she’s fueled by a mission to prove them wrong — and to build a world that’s better for all of us.
Connect with Cindy
Connect with Bob Mathers