This week on How Success Happens, I sat down with longtime writing partners Dan Gregor and Doug Mand, the duo behind How I Met Your Mother, Crazy Ex-Girlfriend, Rescue Rangers, and, most recently, the hit The Naked Gun reboot starring Liam Neeson and Pamela Anderson. They’ve gone from scraping together sketch shows at NYU to crafting a movie that crossed $100 million at the box office. “That guy Liam Neeson really needed a break,” jokes Gregor. “We put him on the map.”
During our chat, the duo discussed risk-taking, partnership, pitching, and getting over the inevitable bombs that come with pushing the limits. Watch above or listen below, and read on for some insights that’ll help you pen your own script for success in three*, two, one!
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Three Key Insights
1. Treat Your Career Like a Scrappy Startup
Dan and Doug didn’t wait for anyone to “pick” them—they built their own stage. They started with the Hammerkatz sketch group at NYU, then hustled their way into the legendary Upright Citizens Brigade. The first time they remember getting paid to be funny, they earned a bunch of Chipotle gift cards and some Rolling Rocks. “We felt like we were rich,” laughs Dan. Doug says he thought he’d be an actor first, and only started writing because it was “a means to give myself parts.” Dan frames it as pure entrepreneurship: “You really quickly realize that nobody’s going to care as much as you about your project and your career,” so you become “the lighting guy, the prop master, the costumer, hair and makeup, wardrobe, camera,” on top of acting, writing, and directing. And also, returning all of the props you bought at Walmart with the price tags still attached to get your money back.
Takeaway: Stop waiting for perfect conditions and create your own platform, even if that means doing every job yourself at the beginning.
2. Pitch Like a Performer, Prepare Like a Strategist
Their performance background at UCB became a secret weapon in pitch meetings. Dan told me it massively improved their ability to sell ideas because they could “perform the concepts” in an entertaining way. Also, he says, it taught them to “modulate based on the room and the tone,” even pivoting mid-pitch if things felt off. Doug talked about going in with a game plan: if they know an idea is likely to get some pushback, they’ll decide in advance how far they’re willing to bend. And they’ll stack concepts “from most conservative to most aggressive” so they can escalate only if the room is vibing. While they’ve had a ton of success, they admit there have been some “brutal” failures along the way. Dan says he still breaks into a cold sweat remembering a Zoom where they sang “Ants Marching” mid-pitch and got, as he puts it, “ripped new assholes” by “very, very big people.”
Takeaway: Treat every pitch like a live performance: rehearse, read the room, have built‑in pivots—and accept that occasionally bombing is just part of the job.
3. Embrace Partner Friction
Their writing process is aggressively unglamorous, starting with breaking the story together and then writing what Doug calls a “vomit draft,” where you’re “just writing everything out, not precious at all.” From there, they separately rewrite, then “turn the key together at the end,” going line by line and punching up jokes. Along the way, differences of opinion will pop up, but Dan says friction becomes fuel: “Creativity does not necessarily happen in agreement,” and arguments often lead to “a third new thing” that’s better than either of their original ideas. Doug adds that he still just wants to make Dan laugh, and if a joke isn’t landing with his partner, “a lot of times I’ll be like, well, that’s the answer.”
Takeaway: Build a process that welcomes messy first drafts, embraces honest conflict, and actively seeks feedback from people who’ve already done what you’re trying to do.
*3.5 Inside Naked Gun with Liam Neeson
It’s no surprise that Dan says, “It definitely takes some nerves of steel to go pitch a dumb idea to Liam Neeson.” But once Neeson heard the crew laughing, he relaxed into the craziness. Doug described the magic of Neeson’s dead seriousness applied to nonsense: “It’s the intensity of Taken about something completely absurd,” and that contrast is what makes the movie feel like a true heir to Leslie Nielsen’s Naked Gun legacy. They also credit director Akiva Schaffer as the first line of trust—Liam trusted Akiva, and that opened the door for him to trust “the idiot writers coming in with different jokes for him.”
Takeaway: Whatever your superpower is—gravitas, technical rigor, discipline— find ways to put it in an unexpected context to create something fresh.
Subscribe to the free How Success Happens Newsletter for weekly inspiration.
Two Free Resources to Learn More
- Check out The Naked Gun reboot and Rescue Rangers, and keep an eye out for their just- announced Disney film Stepsisters and the ABC pilot, Do You Want Kids?, that Dan is co-creating with his wife Rachel Bloom.
- Learn this 10-step process to nail your next pitch.
One Question to Ponder
Dan and Doug turned some of their most embarrassing moments—like bombing in front of “the most powerful” people they’d ever pitched to—into stories that now fuel their careers. So here’s your question:
What is one moment in your life or career that felt humiliating at the time, but turned out to be an invaluable learning experience?
Email your answer to [email protected]—and mention this episode with Dan Gregor and Doug Mand. Your answer just might be read on a future episode.
About How Success Happens
Each episode of How Success Happens shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.
This week on How Success Happens, I sat down with longtime writing partners Dan Gregor and Doug Mand, the duo behind How I Met Your Mother, Crazy Ex-Girlfriend, Rescue Rangers, and, most recently, the hit The Naked Gun reboot starring Liam Neeson and Pamela Anderson. They’ve gone from scraping together sketch shows at NYU to crafting a movie that crossed $100 million at the box office. “That guy Liam Neeson really needed a break,” jokes Gregor. “We put him on the map.”
During our chat, the duo discussed risk-taking, partnership, pitching, and getting over the inevitable bombs that come with pushing the limits. Watch above or listen below, and read on for some insights that’ll help you pen your own script for success in three*, two, one!
Listen Here
Subscribe now: Apple | Spotify | YouTube
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