The Advantages Of “Hiring Old”

Startups are young, sexy–and therefore sometimes have growing pains. Which is why it can be really smart to bring some been-there gray hairs into the mix.

The Advantages Of “Hiring Old”

When Yahoo announced its flashy hire of 18-year-old Nick D’Aloisio, his age got top billing as onlookers marveled at how a teenager built a multi-million-dollar business that could shake up the mobile offerings of a tech giant. That’s impressive, certainly, but in some ways, D’Alosio’s algorithmic app invention may turn out to be the easy part.


For many cherubic savant entrepreneurs, running and growing a company is a bigger challenge than starting it, especially when expansion requires the untechnical task of hiring and managing a staff that remembers Arnold Schwarzenegger as the Terminator–or even Conan the Barbarian–not just the Governator. And even if the founder has the chops to do it, as Ben Horowitz points out, tapping experience to do it faster is often worth it, if the hiring match is done right.

“The number one question I get is how did you attract older people to hire? Like I had to put up my E Harmony profile and it is attractive to ‘older people,’” says Brian Wong, now 21, who founded Kiip (pronounced ‘keep’) at 19 and earned the label of youngest entrepreneur to get venture capital before D’Aloisio came along.

Kiip delivers rewards in place of ads to smartphone games–like a free song offer or $5 credit when you level up–and it’s proving more effective than banner ads. So his company is growing, and at 40 employees, Wong finds himself hiring and managing people with high school yearbooks older than he is. He’s fine with that.

“Experience and age are not equal,” Wong says, speaking equally of himself and his hires. (And let’s just pause here to remind all the readers who rightfully see their graying hair as a badge of honor earned through life experience, that in this article, “old” really means “older than the founders mentioned,” which is almost all of the workforce.)

Wong knows his company needs the kind of experience that comes with years on the planet, not just hours on a smartphone, so he has a board of advisors to lean on for strategic sagacity. For hiring, though, Wong does two things common of young founders trying to circumvent the age gap booby trap: He looks to people he’s already worked with in some way or another, and then he asks unconventional questions.

“The question I ask when they come into an interview is, ‘what is your superpower?’” Wong says. “You’d be surprised how many people get stumped by that.” His own superpower, he says, is “I get people super excited about shit.”


Those kinds of questions without a right answer weed out the bad matches. It’s always important to hire employees who fit in with a corporate culture, but it’s even more crucial when the founder is barely old enough to drink. Hires shouldn’t feel like they are coming on as adult supervision, according to Rick Webb, who at 40 is 14 years older than his boss, David Karp of Tumblr. Webb also founded his own company, The Barbarian Group, before coming to consult with the microblogging platform.

“Being a founder at that age is very high stress and matures them very fast,” Webb says. “They start to look for people they can see themselves being when they are older.” Webb fits that mold describing himself: “I don’t think digital native is a generational term,” he says of himself. “I still wear rock T-shirts and jeans” but he adds, “I act my age. I learned not to drink all the time.”

Webb was brought in to figure out how to monetize Tumblr’s popularity. He knew Karp and worked with him previously as a consultant. “I’m one of many people that he was routinely talking to for years,” Webb says. “A successful board is always introducing a young CEO to people he should talk to regularly, not just at a critical juncture when he needs to meet a grownup.” That’s like a shotgun wedding, he says.

So his advice to a young founder is take as many meetings as you can to develop as many senior hiring options when the time comes to expand. That, and as the ancient Greeks advised, know thyself–and then hire for your weaknesses.

“They should be very honest with themselves and recognize what they are good at. Even if it is not what they love. And that part is hard. That part is no fun,” Webb says. At Tumblr, Karp knows the user community well, he knows how to build a site, and even how to attract investments. So what he needed was marketing and revenue strategy.

“There are times when a younger engineer needs to get a better engineer because the site got too big,” says Webb, which can be awkward. Like in Tumblr’s case, it’s much easier when the founder is an engineer and brings in someone to head up marketing or another department.


Sometimes, though, the growth of the business means that the staffing needs change, and that changes the roles, even at the top.

Leah Busque of Task Rabbit, 32, founded her company at 28 to build a marketplace for small odd jobs like having a neighbor help with Ikea assembly or pick up dry cleaning. As expansion moved to the highest priority she handed over the CEO reins to former Hotwire CEO Eric Grosse. “We wanted to scale up really quickly. So I wanted to find a partner for myself,” she says. “I wanted to find someone who could be just as passionate about the business side of things as I am about the product and engineering.”

A year or so later, she took back the title of CEO, in what she says was an amicable joint decision based on new company priorities. “We all just got in a room and looked at the strategic plan for 2012 and looked at all the emphasis on product and engineering and all just said it looks best for Leah to run this,” Busque says.

It was an amiable parting, she says, because the initial hire was rooted in personal rapport as much as resume alignment. “I was looking for that chemistry fit, that after a really rough day, after all the challenges that we go through, can we go out and have a beer with each other and talk about it.” She would ask herself of candidates: “Is this someone I can call on a Sunday morning and brainstorm ideas with and not feel bad about?”

She’s back as CEO again–but still calls Grosse for advice sometimes, as he remains an advisor.

[Image: Flickr user Rob Warde]