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10 Leadership Lessons From Alexis Ohanian

What Reddit’s cofounder learned the hard way as an entrepreneur.

10 Leadership Lessons From Alexis Ohanian
[Photo: Diarmuid Greene/ Collision/Sportsfile]

Alexis Ohanian has an unprecedented gift: He’s able to use 20/20 hindsight in the present.

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After selling Reddit to Condé Nast in 2006, he’s now rejoined the company full time with his long-time friend, cofounder and CEO Steve Huffman. Today, he helps run it–bringing 11 years of reflection and experience working, writing, and building to the role. During his and Huffman’s absence, very little at Reddit changed, giving them the chance to essentially pick up where they left off as older, more seasoned entrepreneurs.

This makes Ohanian a useful case study. He’s simultaneously a very archetypal founder and very much so not. As one of Y Combinator‘s earliest investments, he was put through the gospel paces of building a company–launching an MVP, testing with users, finding product-market fit, iterating, etc. But after the sale, he went his own way–volunteering abroad, pitching in to launch travel site Hipmunk, and investing at both YC and his own fund, Initialized Capital. In the process he saw and advised a lot of companies–sharpening his abilities to pattern match and spot success.

Here are the 10 vital “don’t”s that Alexis Ohanian says changed his company and career:

1. Don’t Lose Your Perspective

“Stay humble” has become an unsettlingly empty catchphrase in Silicon Valley, and many founders are encouraged to think they’re immune to failure. But none of this is helpful, he says. It only serves to raise expectations for oneself and one’s company until any misstep feels like a disaster.

Early on, he had this mindset shifted for him. Within the first six months of founding the company, his girlfriend fell out of an apartment window and into a coma, his dog died, his mother was diagnosed with terminal cancer, and he sunk into a depression (which he’s since talked about openly to help others who might be grappling with the same). He went from spending hours perfecting Reddit’s business card design (a definite ‘don’t’ he’d like to highlight), to flying home often to spend time with his parents.


Related: When A Founder Boomerangs Back: Alexis Ohanian On Returning To Reddit 

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This gave him a lot of time to juxtapose his work on Reddit with his mom’s experience. Yes, he cared about the company. Yes, it was the central pillar of his young life, and he wanted to make his investors proud. But he found himself more often fueled by his mom, who arrived in the U.S. as a young, undocumented immigrant from Germany. “She skirted the laws to do the right thing for her family, sacrificing whatever life she might have had back home for something bigger for us,” he says. “The best phone call I ever made in my life was telling my mom that Reddit had sold–in a real, tangible way, that seemed like the perfect capstone to her 23 years of unflagging support and sacrifice for me.”

Alexis Ohanian [Photo: Ståle Grut/NRKbeta]

2. Don’t Get Sucked Into “Startup Society”

Even in 2005 in Boston, being a startup founder meant being part of a distinct social set. Months into starting the company, Ohanian and Huffman already received an onslaught of invites to meetups, conferences, dinners, and events. It seemed like he almost had two jobs: building Reddit and maintaining a demanding semi-professional network of friends and colleagues.

“There’s even more pressure now, and it’s very tempting to go to every single thing,” says Ohanian. “You’re guaranteed to find some helpful people out there who will make a difference for you, but for the most part you’re having the same conversations over and over. I went to so many things that were just opportunities for people to talk about how they were ‘crushing it’ or ‘killing it.'”


Related: How To Use Values To Build A World-Class Culture For Your Startup


There’s a happy balance somewhere between being a hermit and a party circuit favorite–and it tilts toward the hermit end of the spectrum, he says. Be judicious about what merits your time:

  • Will there be people there who are valuable for you to meet for precise reasons?
  • Will there be people there who you feel a real connection with or who you want to support?

If you can’t answer yes to either of these questions, don’t go. If you go and realize you’re having a series of cookie-cutter conversations, leave.

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3. Don’t Fake Vulnerability

Much like “humility,” the word “vulnerability” is in the process of being gutted. Many CEOs say that it’s important while only highlighting vanity metrics or ignoring errors. And employees throughout the startup ranks shirk away from admitting fault or mistake in case it impacts performance reviews. But this leaves a lot of people who could do better work (and feel better about it) if only they felt comfortable sharing their true feelings with someone.

Making vulnerability a cultural reality at your company has to start with the founders. If they don’t have tolerance for being vulnerable as individuals, it won’t become an operating principle for others. That’s why Ohanian’s made such a strong push to talk about his past and his emotional experience of leadership with the whole company at Reddit. His advice amounts to this: Don’t be perfect, just keep getting better.


Related: This Startup CEO’s Email To His Team Is A Masterclass In Vulnerability


4. Don’t Choose Risk-Averse Mentors

Ideally, you want to surround yourself with people who will push you past your appetite for risk if that’s what needs to happen.

For Ohanian, one of these people was YC cofounder Jessica Livingston. One scheme she both suggested and supported was faking a press tour in New York. “I was 22, didn’t know anything, and had just mentioned offhand that I had started talking to a few journalists through incidental social connections,” he says. “And she was immediately like, ‘Why don’t you go up to New York and organize a press tour?’ Of course, I had no idea what that meant.”

YC Co-founder Jessica Livingston

It sounded intimidating, and like it would require a lot of planning, so he balked. But Livingston brought it up again, “It doesn’t have to be a big deal,” she said. “Just send out a few emails telling people you’re in town for a few days and if they want to get on your schedule, they should let you know asap. Then just go sit at a cafe and chat with the people who show up.”

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If she hadn’t have nudged him, he might not have gone. And what happened next wouldn’t have happened at all.

5. Don’t Define Success Too Narrowly

“I was shocked how simple this ‘press tour’ thing was when it came down to it,” says Ohanian. It’s easy to overthink actions like this, even when you’re not guaranteed to get anything out of it at all. If your chances of success are slim, you might as well put yourself out there and not invest too much time. So he dashed off a couple sentences to a handful of reporters explaining who he was, linking to Reddit, and saying he’d be around the city and open to meet whenever, wherever. No one knew he was taking the Fung Wah Bus down from Boston, staying on friends’ sofas in New York.

To his surprise, a few reporters took him up on the offer, though no one ended up writing. If that’s how he would have measured his success, the trip would have been an abject failure. And he probably would have cut conversations off early. It’s a good thing he didn’t.

“The best conversation I had was with a reporter, Rachel Metz, who right away said she was thinking of writing about us but decided not to while talking to me,” he says. “We kept on just chatting and eating cannoli together for over an hour. When she left I shrugged and thought, ‘Okay, cool, whatever.'”


Related: Six Reasons To Say Yes When You Really Want To Say No


Little did he know that she’d been freelancing a piece for an editor at Wired, and Reddit came up in conversation. She told the editor she’d met the co-founder and they seemed to be getting some decent traction. The editor promptly went to her husband, who happened to be the head of business development at Conde Nast. Suddenly, an email appeared in Ohanian’s inbox: “Hey, I heard you’re working on some cool stuff. Let’s talk.”

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He called the guy back the same day, which led to Reddit’s first licensing deal–a precursor to the acquisition that soon followed, and ultimately to that miraculous phone call with his mom.

6. Don’t Say “No” When You’re On Your Way Up . . .

“When you’re a nobody, you generally want to say ‘yes’ to everything because it maximizes opportunity at the top of the funnel,” says Ohanian. “When in doubt and when it’s not clear that something will be a waste of your time, default to ‘yes.'”

Alexis Ohanian [Photo: Diarmuid Greene/ Collision/Sportsfile]

7. . . . But Don’t Wait Too Long To Start Saying “No”

This sounds like conflicting advice, but there should be an arc. Saying “yes” more often than “no” makes sense when you don’t know a lot of people and you’re carving out mindshare for yourself. But, echoing his advice about not getting too sucked into the scene, you have to know when you’ve reached a saturation point, and you need to re-center and focus.

“Your ratio of yes to no should shift when you come away from more things thinking, ‘Why did I do that?'” he says. “You become aware that there are many higher value things that you could have been doing for your business, or spending time with your cat or someone you love.”

8. Don’t Chase After The Joneses

One of the most damaging byproducts of saying yes for too long is the oppressive sense you should be doing better. You get gripped with the need to grow as fast or faster, to hire more or better, to build features your users may not need or want–just because someone else is.

Reddit is a perfect example of why this doesn’t matter and isn’t a good strategy. The site has 300 million users, some of whom love it so much they’ve tattooed the logo on their bodies. And yet, it didn’t have a native mobile app until 2016. Internally, it’s staffed like a three-year-old company–and yet it’s continued to grow into the ninth most trafficked site on the internet.

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At the same time, not expanding huge teams and building in all kinds of new bells and whistles didn’t take Reddit off track. By not trying to be something else in the early days, it retained its character and the loyalty of millions.

9. Don’t Let Friendships Get In The Way Of Being An Effective Communicator

“Whenever you’re choosing a cofounder or hiring people to lead big parts of your company or your vision, you have to make sure you can have hard conversations. You’re inevitably going to have a bunch of conversations that you would never ever have with a friend–and I think that a lot of new entrepreneurs don’t anticipate that,” Ohanian says.

To lay the right groundwork, tell the person upfront that you’re guaranteed to get into fights. Ask them how they’d respond to that during the interview phase. How would they constructively approach a problem if you happened to disagree with them? How have they handled strong disagreements in the past? Were they able to see the other side’s point of view at all?

Once you start working together, set the expectation that you will still respect and like them as a person regardless of how assertively you counter them down the road. It’s good to have this touchstone, and it helps to pump the brakes a bit before taking something personally, or allowing it to create a serious rift.

10. Don’t Forget You’re Building Muscles

This goes hand in hand with not being perfect and striving to do better. So many of the skills and traits you need to succeed as a founder can and will naturally be strengthened with time, practice and experience. Whenever possible, Ohanian says, don’t let yourself be discouraged by failure–be encouraged that you’re already better at something.


A version of this article originally appeared at First Round Review and is adapted with permission.