The first time I was told to find and interview an entrepreneur, I was sitting in a Fundamentals of Entrepreneurship course at University of Southern California (USC). The assignment sounded simple. It was not. I had to find a founder, ask for their time, and come back with something worth reporting.
I struggled. I did not know anyone. I did not know how to ask. I was convinced the person on the other end would say no, or worse, say yes and then resent me for wasting their time.
None of that happened. What happened instead is that I got my first interview. Then a second. Then a third. Each one opened a door to another. Over the years, those conversations became a habit. That habit became a way of learning the world.
There are things you cannot get from a book, a podcast, or a well-written blog post. The shape of a decision made at 2 AM. The cost of a first hire who did not work out. The moment someone realized their idea was wrong and had to start again. These are the things that show up in a real conversation — if you know how to listen for them.
A web search gives you the polished story. An interview gives you the texture underneath.
The myth is that successful entrepreneurs share a common story. They do not. Some start young, some start late. Some raise millions, some never take a dollar of outside money. Some quit their jobs, some build on the side for years. Some love what they do. Some admit they are tired.
You will hear ten different answers to the same question, from ten different people, and they will all be right — for their context, their market, their moment in time.
There is no one right path. There are many right paths. Your job is to learn enough of them to find yours.
After a few interviews, patterns will appear.
Some people have a story that is entirely unique — the break that changed everything, the accidental pivot, the chance meeting. Other times you will notice that ten founders from ten different industries say the same thing about customers, or team, or cash. Those patterns are worth more than any textbook chapter, because you found them yourself.
Some stories will stay with you for years. I can still remember specific conversations from my USC classroom, verbatim, a decade later. You will not know which story will stay with you. Just take good notes.
The most common fear is that entrepreneurs are too busy to talk. I understand why you think this. They run companies. They have investors. They look busy on LinkedIn.
Here is what I have learned, having spent years now on both sides of this conversation: entrepreneurs love talking about their path. It reminds them of something they sometimes forget — that they built something out of nothing, and that someone still cares enough to ask how. For many of them, it is a quiet form of refreshment.
Today I still talk with many of the founders I interviewed years ago. Some became mentors. Some became investors. Some are now my students. The ones who refuse are rare. The ones who say yes often say yes quickly.
Keep your first message short. State who you are, what you are studying, and why you are asking them specifically. Do not send a generic request to twenty people. Send a real one to three.
Most students start by listing the famous founders they want to reach. Start somewhere else. Tell your friends, your parents, your neighbors, the uncles and aunties you have not spoken to in years. Tell your professors, your classmates, your part-time boss. The first introduction usually does not come from LinkedIn. It comes from someone who already knows you and remembers that someone they know is a founder. This is what sociologists call the strength of weak ties — the connections you have that are loose, casual, almost forgotten, are statistically the most likely to deliver the introduction you actually need.
This assignment is not designed to be done online. It is designed to be done in person. Meet at their office, their café, their factory, their farm, their warehouse. See where they actually work. Take a selfie together at the end and send it with your thank-you note. The selfie matters less than what it represents — proof to yourself that you walked into the room.
Offer to keep the meeting to thirty minutes. Most entrepreneurs will give you more if the conversation is going well, but start by asking for little.
If they say no, thank them and move on. If they do not reply, wait a week, then send one short follow-up. If they still do not reply, let it go.
Most of the time, someone will say yes. When they do, prepare.
Read about them before the meeting. Know their company. Know at least one thing they have built or said publicly. If they wrote an article, read it. If they gave an interview, watch it. Show up knowing them — not knowing of them.
Write five to seven real questions. Not "what advice do you have for young entrepreneurs." Real ones. Start with how they got here — the actual story, not the LinkedIn version. Ask something specific that signals you did your homework: a decision they made, a moment they have spoken about publicly, a turning point in their company. This is the moment they realize you are not just another student crossing off an assignment.
Then, enjoy the conversation. The line I keep coming back to: be overly prepared, but let the conversation take you. A prepared founder does not stick to a script. A prepared founder has done enough thinking that they can follow the thread wherever it leads, because they understand the territory. That is the goal.
Leave room for the conversation to go somewhere unexpected. The best answers usually show up in a place you did not plan to visit.
Before you end the meeting, ask this: "Is there one person you think I should also talk to?"
Most entrepreneurs will give you a name. Some will introduce you directly. This is how networks build — one honest conversation at a time.
During the meeting itself, share something specific you are learning. Not a polished pitch. A real reflection — something they said that landed, a question that changed how you were thinking about your own venture. This is what turns the meeting from an interview into a conversation. They will remember it.
Thank them in the room. Then within 24 hours, send a written thank-you — text message or email, whichever feels more natural for that person. Tell them what you learned. Tell them what you will take forward. Be specific. A generic "thanks for your time" is forgotten by lunch. A note that says "what you said about hiring your first employee changed how I am thinking about my co-founder conversation next week" is remembered for years.
Then comes the part most students miss. Keep them posted on your journey. Send an update in three months. Tell them what you tried, what worked, what did not, and how something they said helped make that real. Most founders never hear from the students who interviewed them again. The ones who do reach back become a different category in that founder's mind — not a student, but someone who is actually building.
By the time you finish the assignment, you will likely know more entrepreneurs than most people in your age group. You will also have proved to yourself that you can walk into a conversation with a stranger and come out with something valuable.
That skill will matter more in your life than any framework in this course.
Personal interviews are more valuable than any web search. You cannot Google the thing that actually happened.
Entrepreneurs are an unusual group of people. They make peace with uncertainty that would break most people. They hold conviction long after reasonable people would have given up. They find ways forward in situations that look closed from the outside.
Talking to them changes you. Not because they teach you tactics — though they will — but because you start to understand, through sheer exposure, that the kind of life they lead is possible. That someone with less than you started with built something more than you thought possible. That the gap between where you are and where they are is mostly made of conversations, decisions, and time.
Start having those conversations now, while you are still a student and it is still the expected thing to do. It only gets easier.
📘 A Note for GVP Students
Your Entrepreneur Interview Assignment
You must complete at least three in-person structured interview with a working entrepreneur — not a corporate executive, not a consultant, not someone who is thinking about starting. Someone who has built.
Before the interview: research them, write your questions, confirm the time and place.
During the interview: listen more than you talk. Take notes. Ask follow-ups. Share something specific you are learning — make it a conversation, not a checklist. Take a selfie at the end.
After the interview: send a thank-you message within 24 hours, with something specific you took from the conversation. Write a short reflection — what surprised you, what pattern did you notice, what stayed with you.
Then keep them posted. Three months from now, send them an update. Tell them what you built and how their lessons or connections made it real. The relationship is the assignment, not the conversation.
You are not here to validate your idea. You are here to learn how someone built theirs.
Kasper-Tanakrit Sermsuksan is the Founder of SEA Bridge, Dean of SEA Bridge Institute of Entrepreneurship, and a Visiting Lecturer at Chulalongkorn University, Faculty of Engineering (Computer Engineering). Learn more →
