My Student Had to Raise $50 Million So I Could Teach Him the Hardest Lesson in Entrepreneurship

“Congratulations!” I said as I sat down across from a former student. He’d been in my first entrepreneurship class nearly a decade earlier, but I hadn’t spoken with him in years. However, he’d recently reached out to let me know he’d be in town, wanted some advice, and asked if I’d be willing to meet for coffee.

“I’ve been LinkedIn-stalking you for a while now,” I continued while we made ourselves comfortable. “Seems like things have been going really well with the company. I knew you had it in you, but I also have to admit I’m a bit surprised.”

He raised an eyebrow. “Surprised?” he asked.

“In a good way,” I quickly assured him. “Success in the entrepreneurial world is so challenging, it’s unusual to see someone get where they’ve gotten as quickly as you.”

“Doesn’t feel that quick,” he laughed.

“No, I guess not,” I agreed, realizing I hadn’t seen him in at least five years. However, in that time, he’d taken his startup from a quirky little idea between him and his co-founder to a company with a couple hundred employees and over $50 million in funding.

In other words, from where I was sitting, he was “crushing it,” and I was impressed. He’d certainly far outshined anything I’d built during my entrepreneurial career.

“But that’s besides the point,” I continued. “What’s going on? You mentioned wanting some advice. I’m happy you reached out, but I’m not sure I’ve got any useful advice. At this point, it seems like you should be giving me advice.”

The way he sighed revealed the kind of melancholy you wouldn’t expect of a 20-something entrepreneur who was “living the dream.” I suddenly realized how haggard he looked. Sad, too. He wasn’t someone who was “crushing it.” He was someone who was clearly struggling.

“Well, Dr. Dinin,” he began, and then he paused as if searching for the right words.

“I think you’re OK calling me Aaron,” I suggested, trying to soften the tension. “I’m not your teacher anymore. We can be peers.”

“If I’m being honest,” he continued, “I think I’d prefer you to be my teacher. This is something I can’t talk about with most of the people in my current orbit. But my old professor… that seems safe.”

“Yeah?” I said, curious about where the conversation was heading. “Well, whatever I can do to help, just let me know.”

“I need to admit something,” he said, then paused to take a long, tension-building sip of coffee. “I need to tell someone that I hate my job.”

“You hate your job?” I repeated. I hadn’t been expecting him to say that. I was actually relieved. For a moment, I’d thought he was going to share something much worse.

“Yes,” he confirmed. “I hate my job. Running my company is terrible. I don’t want to do it anymore.”

“Of course you hate your job,” I said with a smile and a chuckle. “I’m not surprised.”

“Why is that funny?” he asked. “And why is it so obvious?”

“It’s not so much that it’s obvious,” I explained. “More like it’s expected. It’s something that happens to lots of successful startup founders. Most of them, actually. And, when you stop to think about it, it makes sense. Every startup founder should expect it to happen.”

“Why does it make sense?” he asked. “Why should I have expected this? I thought I was doing everything right. It’s like somehow I’ve managed to accomplish everything I’m supposed to want to accomplish as an entrepreneur, but nobody told me how much it would suck.”

“That’s because you’re confusing yourself and what’s best for you with your company and what’s best for it,” I told him. “But those things aren’t the same.”

“How so?” he asked.

“Building a startup and running a company require two completely different types of work,” I explained. “Building a startup is about being a founder and grinding away at all the nitty gritty details necessary for constructing the foundations of a great company. But running a company is something else entirely. Running a company means being a manager, being a figurehead, and, often, being everyone’s ultimate scapegoat. Rather than building, you spend most of your time listening to reports of what other people are building and doing whatever you can to keep everyone aligned toward the same vision. It’s not necessarily better or worse work, but it’s certainly different than the kind of work you were doing in the early days as a founder.”

“It’s definitely different,” he agreed. I sipped my drink as I let him sit silently and think through my words. In that silence, he seemed to have an entire conversation with himself as he processed my point. “You’re right,” he eventually said. “I’m not doing what’s best for me. And maybe it’s time for me to do that. But how do I get myself out of my company without destroying it?”

“You have to learn the hardest lesson in entrepreneurship,” I told him.

“What’s that?” he asked.

“You have to learn that you aren’t your company,” I said. “In the earliest days of any startup, what’s best for your company and what’s best for you are largely aligned. However, as the company matures, what’s best for it and what’s best for you are going to diverge. To build something truly great, you have to learn how to prioritize those two things differently, and that’s what you’re struggling with. You’ve led your company for so long that you can’t imagine not being in charge. But it sounds like being in charge is no longer what’s best for you. Because it’s not best for you, I’m guessing it’s not best for your company, either. The sooner you admit that, the sooner you can solve the problem.”

He nodded appreciatively. To be honest, I don’t know if I really helped him. As of this writing, he’s still running his company, so our conversation didn’t significantly change anything. But maybe that’s OK, too. I like to think, by simply giving him some perspective, our conversation allowed him to better appreciate his role as founder and his relationship with his company. It’s a relationship most entrepreneurs struggle with as their companies mature.

Entrepreneurs, from first-time founders to seasoned veterans, tend to wrap themselves so deeply in their companies that they have trouble separating themselves from what they’re building. This passion is great for motivation, but it can also cripple founders, companies, or both.

Don’t let it cripple your company. And definitely don’t let it cripple you. If you want to build something truly great and truly impactful, you need to figure out how it can exist beyond you. In fact, you have to, because you’re not an endless source of energy. At some point, you’re going to burn out. And, at some point, you’re going to want to leave. But, if your company can’t exist without you, then you’ll be trapped. That won’t be good for anyone.

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Aaron Dinin teaches entrepreneurship at Duke University. A version of this article originally appeared on Medium, where he frequently posts about startups, sales, and marketing. For more from Aaron, you can also follow him on Twitter or subscribe to Web Masters, his podcast exploring digital entrepreneurship.