The Ladder

My Best Advice

Don’t follow your passion and don’t start a business—go work for a struggling company instead.

Adam Epstein of AdMarketplace
Adam Epstein of AdMarketplace.

Courtesy of Adam Epstein

Occasionally, the Ladder will take a break from solving readers’ workplace problems to ask successful people about career advice: good advice they’ve gotten, bad advice they’ve gotten, advice they’d give their younger selves, and more. This week, I talked to Adam Epstein, the president and chief operating officer of the search advertising firm AdMarketplace. Epstein, a graduate of the University of Michigan Law School, worked as an attorney and clerked for a federal judge, launched an early podcasting business, and joined AdMarketplace as general counsel shortly before it came close to bankruptcy. He helped nurse the company back to profitability and saw it grow from eight employees to about 125 today.

Anderson: How did you end up in search advertising?

Epstein: That’s a long story. I always wanted to be an entrepreneur, and my parents were attorneys. They said, “Go to law school, but don’t be a lawyer.”

That’s very unconventional advice.

It’s the great debate in our family whether that was good advice or not. I think at different points we’ve all taken different positions. Probably for where I was and my level of maturity, it was good advice—I went right out of college. They paid for most of it, but it did leave me with some debt that I otherwise wouldn’t have had.

Not being a lawyer is great advice. Don’t go into tremendous debt if that’s what it means for you to go to law school. But if you can go to law school and not take on debt—I have friends who got scholarships, or the family could afford it, or whatever the case may be—going to law school is an amazing education. It’s just if you have to pay for that education by spending the next 20 years of your life as an attorney, then it’s probably not a good deal. 

What did you learn in law school that you wouldn’t have learned otherwise?

It was the ability to get comfortable with ambiguity, to see both sides of an argument. Another thing you do is you think on different levels of abstraction. When you’re making a legal argument, you have to zoom out to public policy all the way down to the individual fact pattern of a case. In business, your ability to go far in an organization is determined by how many different levels of abstraction you can get comfortable with. If you can go from “How does this impact the industry?” to “What am I going to do about this particular client and this email they sent me about this particular issue?” and navigate everything in between within the course of a day, you’re going to be pretty successful.

You launched a podcasting startup that failed after a few years. When do you recommend that other people should start their own business?

I think it’s similar to becoming a comedian or a writer or an actor. If you’re just kind of talking about doing it and you’re not really doing it, then maybe you shouldn’t do it. I’d never advise anybody to do it unless they said, “No, I have to do it,” in which case I’d say, “Yeah, you totally have to do it.” So it might be one of those ideas that everybody kicks around, but you’ve got to have a real passion for it, or else you’ll just get chewed up. Your ego’s going to get very bruised very quickly. And really the only thing you can do is learn from that, get better, and try again, repeatedly. 

You stuck with AdMarketplace during a tough phase, when it was facing bankruptcy. Why didn’t you jump ship?

I’d gotten some advice long ago from my step-grandfather, of all people. He told me about when he walked into the bank that he ended up being vice chairman of. And his sense was that the bank had a lot of very broken processes. Most of his classmates from business school would have walked out and said, “Oh, who would want to work at that place?” And his response was, “Wow, if I can fix a bunch of the stuff here, I can probably move up pretty quickly.”

I walked into sort of a similar situation in the advertising-technology space. I think a lot of my classmates gravitated toward brand-name organizations, but it’s a little more difficult to distinguish yourself if things are already humming along. Whereas if you go into an organization that has a fundamentally good business model but maybe has some problems with execution, and you can fix those problems, you can rise more quickly. So walking into an organization or a division that isn’t doing well could be seen as a huge opportunity. Because if you can turn it around, you will catapult your career.

If you could go back in time and give one piece of advice to your younger self, what would it be?

Results matter way more than trying. I think in school especially, effort is rewarded and applauded, and in the real world nobody cares about effort. It’s just flat out: Did you get it done, or did you not get it done? Nobody should just feel good about, “Well, I gave it my best shot.” You can throw that justification up for whatever result you get.

Does bad luck happen? Yeah, of course bad luck happens. I get that. Good luck happens. So it’s a matter of: Don’t put all your eggs in one basket. Work a bunch of deals, have a bunch of things that you’ve got going on. If a few of them work out, fantastic. If all of them work out, amazing. And if none of them work out? Might be on you. 

What advice do you give people looking to climb the career ladder?

Underpromise and overdeliver. So many people talk the talk and don’t walk the walk. It’s really a distinguishing characteristic, when you play a little bit low-key, you listen more than you talk, and then you give them more than they expect.

The other advice I give is: Learn how to sell. True selling is listening, understanding needs, figuring out how you can meet those needs, committing to meet those needs, asking for the commitment for them to pay you for your product, and then delivering. Just like everybody should probably be a waiter and work in the service industry, everybody should sell a little.

I have two other little platitudes: Revenue solves all problems. And everybody wants to be big time and nobody wants to do the work.

Do you have any advice for getting that revenue?

Hard work. And hard work really means failing and getting back up. So many people are so scared of failing that they don’t even try. And then when they do fail, and everybody does, they take it as a sign that they should give up. If my career is anything, it’s a case study in not giving up, just refusing to give up until they literally turned off the lights and kicked us out of the office space, and staying in business, and trying to keep it alive for one more day. Hard work is having the tough conversations, it’s hearing the bad news, it’s moving on to the next task after you have the tough conversation and get the bad news. And I think a lot of people have to find the motivation to do that.

Lightning round! Tell me what you think about the following advice: You should network all the time.

Going to a bunch of parties and giving out business cards is a total waste of time. Real networking is based on having a real relationship with somebody.

What about the advice that if you want a certain career, you should email someone who has that job and ask them out for coffee.

I actually do think that’s a good idea. If you’re interested in something, you should go find the person who’s like the greatest at it and try to hang out with them, or try to do something for them for free, if you can afford to, or somehow try to connect with them.

Young people are often told to change jobs frequently to get pay raises commensurate with their increasing market value. What do you think?

I disagree with that. I think that people leave jobs before they should in a lot of cases. You don’t always get recognized when you think you should get recognized, and you don’t always get the raise when you think you should get the raise. Obviously, you think about your contribution, you think about your value, probably a heck of a lot more than your manager or your boss’ boss does. But eventually, if it’s a decent organization, you’re going to get a time to shine, or you’re going to be exposed for being very effective. When that happens, a lot of good things are going to happen for you if you’re at a good organization.

Last one: You should be the first person to show up in the morning and the last person to leave at night.

I think that’s good advice, too. A lot of internal networking happens at those times. If you’re there when something is needed or there’s an emergency or there’s an opportunity for a conversation, good things will happen. But you have to physically be there for those serendipitous opportunities to present themselves.

What is some bad advice that no one should follow?

“Follow your passion.” Most people think that means “Don’t do anything unless you’re passionate about it.” If you really have a passion, absolutely, go follow it. But don’t feel like every job you ever take has to be your passion. Whatever you’re doing, just do a good job at it and find something about it that you’re really into or that you can be really good at. “Find something you’re good at” is way better advice than “Follow your passion.” You can get passionate about being good at whatever you’re good at.

This interview has been edited and condensed for clarity.

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