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

5 min readNov 4, 2021

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Image courtesy Inzmam Khan via Pexels

“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.

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Aaron Dinin, PhD
Aaron Dinin, PhD

Written by Aaron Dinin, PhD

I teach entrepreneurship at Duke. Software Engineer. PhD in English. I write about the mistakes entrepreneurs make since I’ve made plenty. More @ aarondinin.com