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

After selling Reddit to Conde Nast in 2006, he's now rejoined the company full-time with his long-time friend, Co-founder 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.

In this exclusive interview, he leverages what he learned on his long stint away from Reddit to advise other early founders, who — much like 2005's Ohanian — have found themselves trying to make a dent on the industry against long odds. So, without further ado, here are the 12 vital don'ts he says changed his company and career.

1. Don’t lose your perspective.

This sounds squishy and basic (and Ohanian knows it), but he puts a different spin on it. “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. You end up paralyzed or playing small ball, worried about what everyone else will think or how it'll look if things don’t work out.

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.

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.”

While he certainly doesn’t prescribe this level of personal hardship for staying grounded in this industry, Ohanian does say this:

For the last 10 years, nothing that ever happened to me felt like an actual crisis. Everything was manageable. I had been through the worst and nothing else in the tech world could compare.

This feeling — that the worst that could happen to him or his business just wasn’t that bad comparatively — afforded him a degree of freedom. It gave him permission to take bigger risks, to have fun in his work, and to not feel beholden to people’s judgments or opinions. It can be hard to maintain this type of perspective when you’ve taken millions of dollars in funding, and you’ve quit your job — but disconnecting from what your company means in the broad scheme of being a human will only work against you.

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.’”

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. There’s no time for that.

When you’re a founder, every moment you’re not writing code or getting users, you need to be making a conscious choice. Is whatever you’re doing worth your time?

That mantra was seared into his memory by YC, “And I still went on so many fool’s errands because I thought maybe being out there mingling would help,” he says. “Over time, I realized that there was no security or vulnerability in those environments. Out at a bar or a restaurant, everyone’s always killing it, no one’s ever saying, ‘Actually, I have a problem.’” If you’re lucky enough to find venues where people do have those conversations, that’s where you should be. It’s something he’s trying to recreate in private dinners he regularly hosts with his Initialized co-founder, Garry Tan.

3. Don’t pretend at 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.

“We’re all overwhelmed by how much content we take in — not just media, but content in our lives. Conversations we have, things we learn, actions we take,” he says. “And if we look at the vast majority of this content, so much of it isn’t authentic. And the sheer volume of it means that the things that we remember and the people that make a real impact on us, are the ones we feel are true. Increasingly, this will change what we buy and where we work. For leaders, being a real, whole, relatable human being, is a core strength and a competitive advantage.”

His advice amounts to this: Don’t be perfect, just keep getting better.

Admit the ways you’re not perfect knowing that no one is. Explain how you plan to improve based on what you’ve learned knowing that’s all you can do. Make sure you remind the people you work with often that this is all they have to try to do. They’ll be judged against this ethic, not what perfection may have looked like. That’s how Ohanian strives to foster vulnerability every day.

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. Choose mentors, investors, advisors, who have broad vantage points and long histories of watching companies rise and fall. You want folks who have seen enough to know they’ve seen too much, and who will talk you into pushing yourself as a result.

For Ohanian, one of these people was YC Co-founder Jessica Livingston. “I really value all the advice she gave me because she knew how to get me to be true to myself while also going out there and getting as many early users as possible,” he says.

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.”

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.”

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.

“Jessica was extremely helpful, continually saying, ‘Don’t overthink this. You don’t have to go into every conversation with an agenda or expectations that they’ll write about it. Just be yourself and tell them what you’re thinking about and how things are going. Just do it.’ And here I thought I was going to need to call them up and pretend to be my own publicist or something...”

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.’”

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.”

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.

“I’ve really thought about that chain of events,” Ohanian says. “I remember really wanting an article to come out of those days in New York, but I didn’t try to force it to happen. I was open to just having a good conversation and a good pastry — and being that open made a material impact on my career.”

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.’”

7. 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. This is an important phase because almost everything you get offered or any opportunities that come your way will come through another person who has met you somewhere along the line and thought you were alright, says Ohanian.

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.”

There’s a definite curve that happens, he says. And it’s a devious one, because going to lots of things with no clear benefit and being generally ‘in demand’ is also a sign that you’re doing well. And doing well feels awesome. “What founders don’t often realize when they hit this point is that they don’t get more strength from continuing to say ‘yes,’ they get more strength out of starting to say ‘no.’”

That creeping feeling that you’re wasting your time is a lagging indicator, which means by the time you sense it, you’ve already sacrificed a lot. So stay vigilant.

“It’s hard to shake yourself out of this mode of thinking, that no one gives a fuck about who you are or your company and you need to be out there constantly trying to get anyone to care,” says Ohanian. “I really wish I would have known earlier that I didn’t have to be doing the rounds like that, and I could have spent all that time on building the business.”

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’re out there talking about and looking at your competition all the time. You start benchmarking yourself against how other companies that aren’t even in your sector are operating. 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 — it hasn’t done most of the things even an early startup would do today — and yet it’s continued to grow into the ninth most trafficked site on the internet.

“I’m the one responsible for how ugly Reddit looks,” says Ohanian. “It’s only in the last two years that we’ve even thought about design. We didn’t even have a data team before. It’s amazing to think what we could have done over the last six or seven years.”

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, or chasing after what other successful communities like Facebook or MySpace were doing, it retained its character and the loyalty of millions.

9. Don’t underestimate the power of your community.

Of course Reddit is inextricable from the concept of community. But having marinated for years on what makes community work and grow and succeed, Ohanian strongly believes that its a pillar for nearly all companies being built today. It’s also the number one topic he gets asked about.

“Community continues to be this mystery for folks, especially when it’s scaled as big as it is on Reddit. People assume something of that size inevitably breaks,” he says. “Then they look at the smaller Facebook groups they’re trying to build that get limited traction and they decide community just isn’t for them, and they stop trying.”

This is a mistake. And it doesn’t have to go this way.

“For brands, creating a sense of community is quickly becoming everything,” he says. “People are going to choose everything they buy or do — the shoes they wear, the music they listen to — based on how connected they feel to the brand in question. And the tools to build this connection are storytelling and community. Every consumer-facing company these days needs to hire storytellers and community organizers to help them crack this code. Even in B2B, it’s increasingly the best way to get competitive — your customers might be companies, but the people who actually buy your product are still humans who want to connect.”

Once you’ve prioritized community, how do you get it to work?

“I remember when President Obama was getting all this criticism for being a community organizer,” says Ohanian. “In the future, that type of community organizing work is going to create or destroy companies. It’s going to either make them or not.”

According to him, the best communities have a full-time dedicated resource acting, essentially, like the host of a never-ending party. This is the role he cast himself in early on at Reddit, exerting relentless effort keeping conversations going, keeping topics fresh, responding to people’s concerns. “It’s actually a lot of unglamorous work. Imagine what it would be like to talk to everyone at your party, while serving the drinks and apps, while bouncing the riff-raff, while DJing, while making sure everyone’s having a good time,” he says. “If you’re not putting that degree of effort into running your community, it’s not going to take.”

Critically, once you have traction in a community, it’s still easy to blow it. A lot of companies fail by changing up what they’re doing, trying to introduce a bunch of new features or mechanics. That’s not what people want, Ohanian says.

The most impressive communities grow by delivering more people the content they already love faster. That’s how you win.

10. Don’t create values without examples to back them up.

A lot of startups create ‘values’ or ‘principles’ that they suggest their employees adhere to in order to create the culture they want. (This has become such common advice that we don’t even like covering it on The Review anymore.) That’s all well and good, but you better be able to not just say but show exactly why they’re so important. If you can demonstrate a user having a better experience as the result of a company value, they’re 100x more likely to stick and actually make a positive difference in how you operate, says Ohanian.

At the end of the day, the purpose of values is to help people who aren’t you make good decisions for the company, he says. One of their most important applications is guiding what new products or features get built and shipped. Resources are always scarce, and there are always many competing priorities. So, to get a new product built, you should show how it aligns with values that are already generating amazing customer stories.

This is how Reddit decided to build its new user profiles.

For years, the site has elevated content based on its quality and relevance to the community. But it hasn’t given users tools to proactively build and share content with their own audiences.

“Reddit can be daunting,” Ohanian says. “When you open r/ramen, it’s like you’re walking into an auditorium with hundreds of thousands of other people (many of whom are taking photos of, or intensely discussing, their ramen). What are the chances you’ll get the entire room's attention with one booth? You won’t, but you might draw an audience. We want to give people the chance to form better connections and eventually their own following with that type of audience across subreddits.”

This was a controversial concept when it first came up. To argue that it was consistent with some of the best user experiences on Reddit, he pointed to u/shittywatercolour.

He might navigate the real world as the mostly unknown Hector Janse van Rensburg, but on Reddit, the name shittywatercolour carries celebrity status. He’s built an identity — albeit a self-deprecating one — as a terrible amateur artist, who over the years, has gotten quite accomplished at watercolor. Occasionally taking requests, constantly helpful and engaging and making people laugh, he’s become the focal point of an ad hoc community that loves and supports him. He would have never dreamed of making art anyone would care about, much less buy. This is the type of dream Ohanian wants to make possible for more users with Reddit's new profiles.

“I had to really convince the product team to think about this with me,” he says. “I was running around saying, ‘Please, please, please I only need these few resources to do it.’ What got them excited was talking about users like shittywatercolour and how we could build something that would make more stories like that one a reality. They had to visualize how this new feature was going to be consistent with our values, and the example made it tangible.

Ohanian went a step further and flew van Rensburg to San Francisco to spend time with the team both in the office, as well as socially. “You really only know someone once you’ve karaoked with them, and I took Hector out the last time I was in London, when this idea really crystalized. I wanted the team to understand just how much Reddit has affected his life and how much this feature would help him and countless others like him find their voice on Reddit. We held an internal AMA with him and the company; brought him to meetings; walked him through the vision; solicited his feedback; and even got him to illustrate one of our meeting rooms. Talking to your users — empathizing with them — is something you should never outgrow.

He readily admits the “23-year-old Alexis would have scoffed at the idea of ‘company values,’” but now he sees exactly how critical they are as the 250-person company gear up for growth. “At a fast growing company, values become a shorthand for why decisions are getting made — especially when founders or execs aren’t in the room,” he says. “But in order for that to happen, everyone needs to really know and internalize the values that will scale our original vision. I wish I hadn’t been so dismissive of that in the past.”

11. Don’t let friendships get in the way of being an effective communicator.

Ohanian and Huffman have been partners for a long time. They met on their first day of college, and their prior collaborations were mostly in World of Warcraft. By the time they started the company, they were fast friends — which, in the startup world, can be dangerous. While they remain close colleagues and friends, Ohanian wishes he would have thought through how their communication would evolve beforehand.

“Whenever you’re choosing a co-founder 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,” he 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. “Coming back together in 2015 started thanks to Steve’s therapist, who encouraged him to reach out and repair our broken relationship. Now I’m encouraging every founding team I meet to seek an executive coach or some kind of outside mediator to help have the hard conversations sooner rather than later," Ohanian says.

12. 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. You’ve already failed if you expect yourself to be good at everything you’ll need to do right away. Whenever possible, Ohanian says, don’t let yourself be discouraged by failure — be encouraged that you’re already better at something.

Cultivating constructive relationships with your co-founder and others is one of those muscles.

I see a lot of young founders get so deflated by conflicts or disagreements, when they should see that as early, free exercise for muscles that will make them great at relating down the line.

The best way to evolve faster as a leader is to be systematic about identifying your strengths and areas for growth, and then thinking about how to proactively work out those muscles.

One of the muscles he’s building lately is organized productivity. He just adopted what he calls the “Meek Method” (Joel Meek is VP Operations at Reddit) of using his inbox as his task list, and relentlessly going after inbox zero. Now, if he has something to do, he emails himself immediately. And then he works hard to remain focused long enough to power through the other items that need to get done that day.

“That discipline is just another muscle, like anything else,” he says. “You just have to fucking do it and trust that change will happen over time. And if it hurts, enjoy it, because that’s what growth feels like.”

Photography by Michael George.