GoKawiilThis 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.”
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