Visiting Dignitaries

Trigger Media Expands InsideHook, a Thrillist for the ‘Established Man’ with Help from Actor Ed Burns

What happens when the Thrillist dude becomes The Man?
6460 inside hook martin sobey Trigger Media Expands InsideHook, a Thrillist for the Established Man with Help from Actor Ed Burns

Mr. Russell, left, and Mr. Keidan (Photo: InsideHook)

In fiction, the experts tell you to write what you know. In founding a company, you’re told to fix the problems you find in your own life. So it makes sense, then that Andy Russell–a leading investor behind email newsletters like Daily Candy, Thrillist, Tasting Table, and PureWow–has decided the world needed InsideHook, another free lifestyle newsletter, but this one targeted to his own demographic: “The discerning, urban, established man who lives a fast-paced and rewarding life,” as the company describes it.

In a visit to Betabeat’s offices last month, Mr. Russell, who helped launch roughly one email property a year for the past eight years as a partner at the powerhouse investment firm Pilot Group, said he recognized the need to cater to the 35-to-55 set by looking at his own life. On date night, he and his wife would end up at the same sushi place around the corner. “My wife looks at me and goes ‘Again? Where’s the guy who climbed Kilimanjaro on our honeymoon?’ Or I used to own a restaurant in the West Village called Moomba. ‘Where’s the guy who started the hottest nightclub/restaurant in New York?'” 

(You don’t have to take Mr. Russell’s word for it. Here’s a 1998 article from Ruth Reichl talking about how hard it was to compete with “the Beautiful People” for a reservation.)

Of course, even the Beautiful People get older. Through its newsletter and website, InsideHook will offer “curated experiences” that cater to the male urban-dweller who is aged out of Thrillist, but too damn successful to waste his time researching something fun to do on a Saturday night. Thrillist cofounder Ben Lerer must not mind any overlap–he’s an advisor to InsideHook’s parent company, Trigger Media.

InsideHook’s tagline is “The Life You’re Meant to Live,” promising, “inspiration for the driven man,” in other words hustlers like, say, Mr. Russell or InsideHook’s CEO and cofounder Jonathan Keidan, a music industry veteran and former COO of the Jack Welch Management Institute, who represents the bachelor perspective. (Paging, The New York Times!)

In an interview with Betabeat, the New York-based company announced a partnership with Ed Burns, one of the many, many celebrity patrons who frequented Moomba in its hey-day–and a paragon of maturing American masculinity in his own right. Along with the partnership, InsideHook is promoting the nationwide expansion beyond New York City that began back in May. In addition to being an equity participant, Mr Burns is curating “his favorite restaurants, travel destinations, outdoor adventures, cultural activities, style finds and products for men,” the company said in a press release. Celebrities who curate in their spare time, now where have we heard that before? Oh, yeah. Categories include recommendations on Food & Drink, Health, Travel, Tech, and Action. Mr. Russell said he knew Mr. Burns through, “Being born and raised in New York City and knowing a ton of people.”

InsideHook is the first startup to come out of Trigger Media, a $22 million seed stage fund and incubator for what Mr. Russell calls “subscription curation services.” It was launched last fall shortly after Pilot Group cofounder Bob Pittman was named CEO of Clear Channel Communications. (You may also remember Mr. Pittman, who founded MTV, from his stints as CEO of AOL and Time Warner Enterprises.) Mr. Russell came into Pilot Group as the firm’s youngest partner, focusing on digital and decided it was time to start something more early-stage outside of Pilot’s portfolio of TV and radio stations. His mentor Mr. Pittman is one of Trigger Media’s biggest investors, but the rest of the investor table is pretty impressive as well, including Conde Nast/Advance Publications, former MySpace president Jason Hirschhorn, former Daily Candy CEO Pete Sheinbaum, who is also an advisor to InsideHook, as well as Michael Kassan, former president of Initiative Media Worldwise, Ken Fox, cofounder of Internet Capital Group, and OneKingsLane founder Ali Pincus. (Ms. Pincus is the wife of Zynga founder Mark Pincus; Mr. Russel was an original investorin Zynga.)

Mr. Russell told Betabeat there’s a “huge void in the digital sphere,” for services catering to older men. “Probably one of the reasons it’s a huge void in the daily email publications is because Bob Pittman and I didn’t do it,” he said. “I wasn’t exactly this demo/psychographic yet.”

But that void might be in part a reflection of how tricky it is to speak to this market. After scrolling around InsideHook, it was hard not to notice the ubiquity of pun-y headlines. There’s a round-up of spas that cater to men called “Spa and Order,” a survival class on the zombie apocalypse called, “Dead Clan Walking,” and luxury outdoor bedroom on a Central Park roof called, “Lady and the Camp.”

Unless they’re all New York Post loyalists, we’re not sure readers will appreciate the humor. Besides, what makes a zombie training class better for a 35-to-55-year-old than Thrillist’s younger demographic?

Mr. Keidan, InsideHook’s CEO, said the guiding principal is making any free time you might have away from your high-powered job more meaningful. “Some of my best friends for the past five years, what have I done with them?” asked Mr. Russell, seconding the notion. “Well we’ve gone out to a great restaurant, we had drinks and we had funny conversation, but there’s no concrete memory in there.”

As for those puns, InsideHook’s three editors try to tailor the voice to someone charming and witty who is a “a little goofier with his friends,” explained Mr. Keidan, emphasizing the editors have to be uber-connected to the top “mixologists” and “cultural tastemakers.” We’re definitely the wrong demo to tell if the recommendations are appealing, but the site seems little sparse in terms of regular updates, at least for now.

Nonetheless, Mr. Russell said it’s the fastest growing subscription service he’s ever been involved in and that’s just through word-of-mouth. InsideHook refused to share any numbers, but Mr. Russell did note that they doubled subscriptions last month.

InsideHook plans on making money solely through advertising. We were very surprised to hear that advertisers actually find the rich white men segment under-served. Mr. Russell said that’s because trying to reach them online via news or sports channels can cut affluence out of the equation. “We’ve walked into meetings with heads of ad sales at some very big luxury brands and we give them our pitch. One smiled and said we’ve been looking to spend money in this area, but we haven’t had anyone to spend it with,” said Mr. Keidan.

Although the Gilt Groupes and Groupons of the world have made the market much more crowded than when Mr. Russell first entered the game with Daily Candy, he argued that “Guess what? Email is a wonderful way of delivering a great message.”

“We did over a year of research into the space,” added Mr. Russell. “You can only imagine how many people over 13 years have pitched me this model. And I’ve only done eight of them.”

Follow Nitasha Tiku on Twitter or via RSS. ntiku@observer.com