10 Questions: Marcus Nelson, co-founder and CEO, Addvocate

FORTUNE — If there’s one thing you can say about Marcus Nelson, it’s that he’s adventurous. He once spent two and a half months smuggling 90,000 bibles into the former Soviet Union. He is a former J. Crew catalog model. He legendarily felled 400 men in a single charge in the Battle of San Jacinto. (Okay, that last one isn’t true.)

In all seriousness, though, Nelson spent his youth working non-traditional jobs. He made three different attempts to go to college, where he studied theology, English, and communications. Somewhere along the way, it hit him: With a knack for starting new things and a flair for marketing, he should probably be an entrepreneur. So he dropped out.

Since then, Nelson co-founded a non-profit called Rockwater, founded a website development company at Superstarch.com, and co-founded UserVoice, a customer feedback company. Eventually, he found his way to Salesforce (CRM), where he built up the enterprise technology company’s social media program.

At Salesforce, Nelson found that employees were eager to share news about the company they work for, but there was no standard way to make sure social media posts were in line with company branding. Which is where he got the idea for his current company, Addvocate. Addvocate helps employees post social media content that has been pre-approved by their company. Employees see a feed of ready-to-go posts that they can share across sites like Twitter and Facebook. The employees, therefore, can advertise and advocate (get it?) for their company without worrying whether their posts are going to get them in trouble with their supervisors.

Nelson, 42, is based in Silicon Valley. He spoke with Fortune.

1. Who in technology do you admire most? Why?

Two people: I like Elon Musk as a visionary. I think he’s our modern-day equivalent of any number of industrial revolution-type of characters in that some people back then would have said, “You can’t do this. It’s too hard,” or whatever. Elon never seems to give a care to those thoughts. He looks at things that are broken or aren’t working the way that they should, and he just finds his own way. I respect that. I wish there were more people like that. And then the other person I would say I really respect is Dave McClure. He is also one of the PayPal Mafioso who just works his ass off. He’s in the spirit of go, go, go. He makes a lot of little bets on people who may or may not deserve them, and he continues to believe. The industry needs those kinds of people.

2. Which companies do you admire? Why?

Nest. They take things that are seemingly mundane and make them into something more significant. There’s something to be said for taking things that we all use every day, ripping them apart, and starting over.

3. Which area of technology excites you most?

The convergence of software and hardware. We’re seeing things that have always been dismissed as archaic having a renewed sense of purpose because of technology. Things like light bulbs, outlets, thermostats. The fact that we’ve seen something as utilitarian as a cell phone go from a glorified pager and communication device to today a more powerful piece of technology than what took people to the moon. And it’s sitting in our pocket, and it knows who we are, where we are and everything about us. That software and hardware is serving a greater purpose than merely showing a website or playing Flappy Bird — that’s what excites me most.

4. What advice would you give to someone who wants to do what you do?

Things are not like they are on tech blogs. Most startup experiences are going to get worse before they ever get better. But they always will get better if you don’t quit. That’s the key thing. Your world will be rocked. Your confidence will be broken. Your sense of direction will seem directionless at times. Your sense of purpose will be challenged. But that’s okay. You have to surround yourself with people who will help you through those things because you won’t be able to do it by yourself. You need to reach out when you know that things are dark. The worst thing to do is to do nothing. If you do that, you will be nothing. It goes back to a Jewish proverb, “You have not because you ask not.” That’s what it boils down to. If you need help, ask. If you need confidence, ask. If you need to be built up, ask. If you need money, ask.

5. What is the best advice you ever received?

Go where you’re celebrated, not tolerated. Don’t waste time trying to be significant where you are not appreciated. Either someone will appreciate you, and enable you to do better and more, or they won’t, and you’ll just wind up being frustrated. Flowers stand out in a pigpen, but likely won’t last long enough to bloom.

6. What challenges are facing your business right now?

Customers. How do we help customers do what they need to do better? What is it that they need that we’re not doing? Customers are always a challenge with enterprise software. In the consumer world, you’re given a bit of leeway in that people either like it or hate it, but you’ll know right away. In enterprise software, it’s not that cut-and-dry.

7. If you could have done anything differently in your career, what would it have been?

Not sure there’s really anything I would do differently as the scars and failures of my past are what make me so focused and driven today. I do wish at times I had been more patient and didn’t try to force things to happen. In my younger years, people wouldn’t understand the ideas or direction I could see us going. Instead of stepping back, I would get frustrated and draw back. The real issue was I hadn’t sat down and figured out the best way to articulate my story or rationale. That’s not their fault; it was my fault. And things might have gone much smoother had I just relaxed and taken the time to overly communicate.

8. What was the most important thing you learned in school?

When I was in college, my brother and I were working on a startup. I pulled aside a professor of mine and showed her our marketing strategy and creative ideas, and she said, “We don’t teach you how to do this. You either figure it out or you don’t, and you figured it out. No piece of paper is going to say that you can do this.” And that became my last semester of college.

9. What was the last book you read?

This is going to sound like I’m being a total kiss-up since he’s an investor, but the last book I read cover-to-cover was Youtility by Jay Baer. But another book I’m reading right now is The Checklist Manifesto [by Atul Gawande]. This is the book that Jack Dorsey makes everybody read. It says that the reason why there are failures in anything is because you haven’t gone through the checklist. Meaning someone hasn’t thought all the way through something before starting it.

So if you think about any event you’ve gone to, you know that someone has gone through the checklist and asked, “Do we have enough chairs? Do we have our speakers? Who’s doing the sound system?” All the quality assurance things. If any of those things don’t go right, something bad can happen. And if something bad does happen, it’s because someone didn’t go through the list. The core of the book from what I can tell so far is about being deliberate. You can be patient if you’ve gone through the list and you know what you’re going to do. There is a calm that comes over you when all you’re doing is executing the plan. There’s a confidence in checking off the boxes.

10. What is one unique or quirky habit that you have?

I can’t sit down when I start to get excited. It’s something that’s affected me since grade school. When it happens in meetings, I usually have to let everyone know that this is what I do and to not be alarmed.

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