When Susan Tynan joined LivingSocial in 2011, she was struck by its CEO, Tim O’Shaughnessy. She had known him a little bit back when they worked at another startup; O’Shaughnessy, though quite young then, was rapidly rising through the ranks. But now, as O’Shaughnessy addressed hundreds of employees at the first all-staff meeting Tynan attended at LivingSocial, she was struck by what a forceful and charismatic leader he had become. He communicated the company’s progress and mission with great clarity and precision. The whole staff listened, admiring and rapt.
O’Shaughnessy was, at that time, Tynan’s boss’s boss. He was incredibly busy, and she rarely got much face time with him. Tynan was managing LivingSocial’s daily deals in the home-services category, fielding complaints when customers were unhappy with a deal involving a plumber, electrician, or even custom framer. Even in those monthly audiences with O’Shaughnessy, Tynan was one of several people in the room. Very seldom did the two of them have any direct, one-on-one interaction. “I had a lot of respect for how busy Tim was,” recalls Tynan. Everyone did, in fact; in the D.C. entrepreneurship scene, Tim O’Shaughnessy was a celebrity.
In 2013, Tynan elected to leave LivingSocial, having been offered a position as VP of product at a taxi-booking app called Taxi Magic. She put in her notice, which disappointed her boss. Then, to her surprise, O’Shaughnessy called her into his office. Was there anything he could do to make her stay? Maybe there was another role for her at LivingSocial? Tynan was flattered that O’Shaughnessy thought highly of her, but she explained that she was excited about the Taxi Magic offer. The two parted amicably. “It was a nice meeting,” she recalls. But while he pressed her to stay on, she doesn’t think he exactly lost sleep over the loss: “I was one of thousands of employees,” she says.
What Tynan didn’t tell O’Shaughnessy at the time was that she had near-term ambitions of founding her own startup. While at LivingSocial, she was struck by the custom framing category in particular. What set apart custom framing in the daily-deals universe were two things: First, there was enormous demand. A custom framing deal ran every week, on the site, in one market or another. Second, there was enormous frustration from customers. Each deal seemed to result in an inordinate number of complaints over pricing or service.
Though 2012 and 2013, Tynan began to test some of her theories on friends, acquaintances, anyone who would listen. Did they use custom framing often? Did they have a good experience? “It’s a funny category to talk about ‘horror stories’ in,” she laughs, “but everyone had a horror story.” People were sick of the upselling, the byzantine pricing structures. They couldn’t believe how long they had to wait.
After less than a year at Taxi Magic (later renamed Curb), Tynan decided she was ready to strike out on her own. With a coterie of former colleagues and some new hires, Tynan founded Framebridge, an online custom framing service. And one of the first people she set about contacting in her new role was her old boss, Tim O’Shaughnessy (who today is president of Graham Holdings).
It was January 2014, just a month after she left Taxi Magic, when Tynan sent the email. Her goals for the meeting were genuinely very modest. Tynan had decided to fund Framebridge with venture capital, and she wanted to pick O’Shaughnessy’s brain about the ins and outs of funding rounds. O’Shaughnessy remained extremely busy, she knew, but she was confident he’d give her a few minutes. His assistant wrote back to set up a meeting for coffee at the Sofitel near LivingSocial’s offices.
The first surprise at that coffee meeting was that O’Shaughnessy had already heard about Tynan’s custom-framing startup “through the grapevine,” she says. And the second big surprise: O’Shaughnessy wasn’t only willing to help her navigate investment. O’Shaughnessy wanted to invest himself.
“I was so flattered,” recalls Tynan. “I was shocked. I did not see it going this way.”
Tynan had known that O’Shaughnessy respected her work at LivingSocial, but now she felt validated in about a dozen other ways. He liked her idea enough, and thought enough of her ability to execute, to put his own money on the line. “At that moment, I realized there was mutual respect,” she recalls. “It felt good.”
Mere months prior, Tynan had been one of countless employees to O’Shaughnessy, albeit a notably productive one. Now, she realized, their relationship was changing.
Framebridge has since grown rapidly, with 20% month-over-month growth in sales last year and $11 million of investment to date. And in the two years since that coffee at the Sofitel, O’Shaughnessy and Tynan’s relationship has continued to evolve, says Tynan. He’s still a mentor and investor, and there’s still a sense in which a power differential remains. But as fellow founders and CEOs, they share more in common.
Tynan remembers a tense month over the summer. She had to make a very difficult personnel decision, and the board, which includes O’Shaughnessy, was kept appraised. In the minutes before her subsequent board meeting, Tynan was nervous.
As it happened, O’Shaughnessy walked in first, and the two of them had a quiet moment alone. O’Shaughnessy was still an investor, after all, and Tynan felt a pang of worry: What would O’Shaughnessy think of the decision? Would he lecture her on it? Express mild disapproval?
Instead, he simply leaned in, and said, “Gosh, that must have been hard.”
It was a small, human moment, but another one that underscored how their relationship had changed.
“I remember thinking, ‘This is someone who really gets it, who’s been through all of the highs and lows of entrepreneurship,’” says Tynan. “And I was really glad he’s on my side.”