Podcast Interview Questions for Entrepreneurs: 30+ Questions to Ask

Any podcast host can prepare questions for their next episode within an hour. But only a few can come up with the right podcast interview questions for entrepreneurs that are actually worth listening to.

Most founders get interviewed a lot. They've been asked about their "why," their morning routine, and their “biggest failure" so many times they can answer on autopilot. You will just get the same, PR-friendly version, and your listeners lose interest halfway through the episode.

Your podcast needs good entrepreneur interview questions that catch founders mid-thought and pull out the story behind the story. And when that happens, your listeners feel it.

In this blog, we will explain the top 30 questions to ask entrepreneurs and how to prepare for a podcast interview.

30+ Podcast Interview Questions for Entrepreneurs

Check out these things to talk about on a podcast to make guests remember specific moments, explain their decision-making process and tell stories that your audience can relate to.

Questions To Ask A Founder on the Entrepreneurial Journey

The early journey often includes the stories founders rarely tell in their glossy interviews. So, you can ask podcast questions about what happened before the success became obvious.

1. When you decided to build a business, what was going on in your life?

This question provides the founder room to explain the personal, financial, career, or market event that really pushed them to entrepreneurship.

2. What did you believe about entrepreneurship when you started that you no longer believe?

Founders learn differently. This question can reveal lessons learned over years and challenge some of the assumptions your audience may have about building a business.

3. What was the first decision that made your business feel “real”?

It might have been registering the company, or hiring someone, or getting the first customer, or quitting a stable job. You can get an authentic story as an answer.

4. Who was the first person to take your business idea seriously?

This can reveal an early criticism, disagreement, or doubt. More importantly, it shows how the founder reacted when someone challenged their idea.

5. Looking back, is there anything about your early journey that seems completely different?

This is a nice way to get a founder talking about hindsight bias. What seemed like a bad decision then, creating an opportunity unforeseen later.

Startup Interview Questions About Their Business

Your audience wants to know how the founder found the problem, validated the idea, signed up customers, and built something that people actually wanted.

6. What customer problem did you see as a business opportunity?

Good businesses usually start with a problem that’s worth solving. Let the founder tell the story of what they saw, who experienced the problem, and why existing solutions didn’t cut it.

7. How did you get your first paying client?

Such podcast guest questions can elicit a surprisingly elaborate story. Cold outreach? Personal contact? Social media post? Referral? Plain old luck? Early customer acquisition speaks volumes about a startup.

8. What lessons did your first 10 customers teach you that your research could not?

Market research can tell you what people say they want. Real customers tell you what they will actually use and pay for. This question is connected to that difference.

9. What was a business assumption you were dead wrong about?

All startups are based on assumptions about customers, pricing, distribution, demand, or product features. The assumption that failed can show how the company responded.

10. What aspect of business building took you far longer than you expected?

Founders often underestimate hiring, product development, sales cycles, legal work or customer support. This question gives listeners a more realistic view of what it takes to build a company.

11. What are you looking for in an opportunity?

Successful founders have lots of opportunities. The interesting thing is how they answer no. Ask entrepreneur interview questions about revenue potential, strategic fit, customer demand, timing, and opportunity cost.

12. What metric tells you your business is really healthy?

That adds some useful technical detail to the conversation. Depending on the business, the answer could be revenue growth, gross margin, churn, retention, customer acquisition cost, lifetime value, or cash flow.

Podcast Interview Questions for Entrepreneurs on Failure and Difficult Decisions

"What's your biggest failure?" is one of the most over-asked questions to entrepreneurs. Generally, the more specific you are, the better the answer you will usually get.

13. What decision cost your company the most money or time?

The value is in the decision-making process. What knowledge did the founder have? What were they missing? How much did the mistake cost you? What happened after?

14. When did you really think about quitting?

Do not rush this question. Let the guest explain what was going on at the time, how close they were to quitting, and what made them decide to stay.

15. What red flag did you ignore for too long?

Such podcast talking points can uncover issues with customers, cash flow, hiring, product demand, or company culture. It also provides an extremely practical warning sign for listeners to watch for in their own businesses.

16. Describe a time when you had to make a decision without all the information.

Entrepreneurs rarely have perfect data. This question shows how the founder deals with uncertainty, thinks about risk, and decides when they have enough information to move forward.

17. What is one mistake you would make again? Why?

Some errors are not useless. Sometimes a painful experience gives knowledge that could never have been acquired otherwise.

18. How did you know your first strategy was not working?

What’s interesting is not that the strategy failed. Ask what convinced the founder, how long they waited, and what they changed based on that.

Podcast Interview Questions for Entrepreneurs About Growth and Leadership

As a company grows, it can change quite a bit. What worked for the founder managing five people may have to change radically when the team is 50 or 500 strong.

19. What got harder as your business started growing?

The answer to all startup problems is Growth. No. More customers can mean more support issues. More employees can mean more management complexity. And more revenue can mean more operational pressure.

20. Which role did you find hardest to take off your plate?

Founders are often used to doing everything and become bottlenecks. This question shows how they learned to delegate and to trust others.

21. How has your philosophy on hiring changed?

Ask the founder startup interview questions about what has changed in their hiring criteria.

22. What do you check before giving someone an important decision?

Listen to how the founder rates judgement, ownership, communication, technical ability, and reliability.

23. How do you handle someone on your leadership team with whom you disagree?

Good disagreement can lead to better decisions. This question can reveal whether the founder relies on data, debate, hierarchy, experimentation, or simply their own gut.

24. What hard-learned leadership lesson did you learn?

One thing that experience teaches you is that it usually beats generic leadership advice. Ask the guest to tell you what the situation was that taught the lesson to him or her.

Podcast Interview Questions for Entrepreneurs About the Future

Finish with podcast questions looking forward. These can create strong closing segments and give listeners something to discuss after the episode.

25. What change in your industry are most businesses underestimating?

This can show change in technology, customer behaviour, regulation, competition, or pricing.

26. What is an emerging trend you wish was getting more attention today?

Ask the founder why they think the trend matters. A prediction is much more interesting if the guest explains the basis for it.

27. What would you build if you started from scratch today?

This is one of the best business podcast questions because it takes away the advantage of the guest’s current company, team, customers, and brand.

28. What is one opportunity your company has not tapped into yet?

The answer could reveal where the founder sees future growth. It may also show new products, new markets, partnerships, or customer segments.

29. How would you define success for the next five years?

Revenue is one answer, but not the only one. The founder may care about market share, impact, team size, profitability, independence, or solving a particular customer problem.

30. What advice would you never give to a new entrepreneur?

Instead of another list of motivational tips, you might get a strong opinion about popular advice the founder believes is misleading.

31. One question you wish interviewers would ask you?

Keep this one for last. It allows the guest to steer the conversation and can bring up a subject you never thought to ask about.

How to Prepare for a Podcast Interview?

Good podcast prep means knowing your guest well enough to ask better questions and to follow interesting answers. All you need is a structure to work with, and room for the conversation to breathe.

• Check their website, LinkedIn profile, past interviews, and recent work.
• Know their product, target market, business model, and current events.
• Listen to previous interviews. Make a note of questions they have already answered so that you do not ask them again.
• Choose topics that are relevant to what your listeners really care about.
• Create brief follow-up question prompts such as “Why?”, “What happened next?,” and “What would you do differently?”
• Spot career transitions, failures, launches, controversies, or odd decisions worth asking.

Frequently Asked Questions (FAQs)

1. What are some good questions to ask a podcast entrepreneur?

The good entrepreneur interview questions are about decisions, mistakes, customers’ problems, turning points, leadership challenges, and plans for the future.

2. How to develop better podcast interview questions for entrepreneurs?

Do some research on the guest's background and past interviews first. Then, ask questions based on their specific experiences, recent developments, opinions, and stories they haven't already told at length.

3. What are the best topics for a podcast?

Discuss the guest’s journey, business decisions, failures, lessons, changes in the industry, and experiences that can help the audience. Try to focus on specific stories.

Conclusion

Do your homework on the guest, pick the podcast interview questions for entrepreneurs that work, and allow space for the conversation to evolve naturally.

That approach can help foster the kind of thoughtful and engaging conversations like Chris Herman’s podcast.

Because sometimes the best answer doesn't come from your list of questions. It’s in the follow-up you almost forgot to ask.

Think you'd make a great guest? Apply here and share your story on On Deck

‍