How do successful founders get through the hardest times? Their real stories show it: ask the right questions about their lowest point and what kept them going.

Founders get through hard times in many different ways, and the best way to learn how is to hear it from a real founder, in their own words. This post gives you a simple interview guide and story template to capture a founder’s hardest season: the day they almost quit, what they felt, who helped, and what made them keep going.

Use it for a restaurant owner, a gallery founder, a travel business owner, a bank founder, a plumber, a nonprofit leader, or the third generation running a family business. Every founder has a hard season. Their honest story can help someone else hold on.

Why this story matters

Most business stories skip the hard parts. We see the grand opening and the success, not the nights of doubt. That leaves new entrepreneurs thinking they are alone when things get tough.

A real story about almost quitting does three things. It tells struggling owners that hard seasons are normal. It shows practical ways people got through. And it honors the founder’s courage. These stories are often the ones readers remember most.

Before the interview: permission and honesty

This post is a template and interview guide, not a finished story. Use it only with a real founder who agrees to share. Explain how the story about their hardest season will be used and where it will appear. Get their permission in writing before you publish.

Use only their real words and facts. Do not fill gaps with guesses, made-up quotes, or numbers you cannot check. If a detail is unclear, ask again or leave it out. Let the founder read the final draft before it goes live, and remove anything they are not comfortable sharing.

Interview questions

Ask these questions in a relaxed setting. Let silence do some of the work. Follow up with “Tell me more about that” whenever an answer feels important.

• What was happening in your business when you came closest to quitting?
• What did a normal day look like during that season?
• What thoughts kept you up at night?
• Who knew how hard it was? Who did you hide it from?
• What was the moment you decided to keep going? What happened that day?
• Who helped you, and how?
• What did you change after that moment?
• What did you have to let go of?
• How did that season change the way you lead today?
• What would you say to someone sitting where you sat back then?
• Is there anything you are still learning from that time?

Story template

After the interview, shape the founder’s answers into a short story using this outline:

• The setting: What the business looked like before the hard season.
• The low point: One specific moment, in the founder’s words.
• The turn: What happened that made them keep going.
• The change: What they did differently afterward.
• The lesson: One practical takeaway for readers.

How to turn answers into a story people remember

Pick one moment, not the whole life story. Look for the answer where the founder’s voice changed, slowed down, or got quiet. That is usually the heart of the story. Use short paragraphs and plain words. Quote the founder exactly, and only with permission. End with a lesson another business owner can use this week.

Record the interview only if the founder agrees, and take notes either way. A recording helps you quote exactly. Afterward, send a thank-you note, whether or not the story is published. Sharing a story is a gift.

What this looks like in different businesses

• Restaurant owner: Ask about the slowest season and what kept the doors open.
• Artist or studio founder: Ask about the time they doubted their work would ever support them.
• Travel business owner: Ask about a season when travel stopped or plans fell apart.
• Banker or financial founder: Ask about a hard decision during an uncertain time.
• Home services owner: Ask about losing a key crew member or a big job.
• Family business leader: Ask how the family held together during a hard stretch.

Where to share the finished story

Once the founder approves the draft, think about where the story about their hardest season will help most. It might fit a blog post, a short video, a newsletter, a staff training session, or a framed page in the lobby. You can also pull one short, approved line for social media. Ask the founder before using the story anywhere new. Keep a copy of their written permission with the final version, so anyone on your team knows what is allowed.

Service before Self in every story

Hard seasons often reveal a founder’s deepest values. Many founders keep going because people depend on them: employees, customers, and family. Listen for moments when they chose to serve others even when it cost them. Those moments show Service before Self in its truest form, and they are the heart of a story worth sharing.

Your Next Step This Week

1. Choose one founder you admire and ask if they would share their hardest-season story.
2. Get written permission and agree on where the story will appear.
3. Use the eleven questions, then shape the answers with the five-part template.

Frequently Asked Questions

Is it okay to share a founder’s struggles publicly?

Only with their clear permission. Let them decide what to share, review the draft, and remove anything they are not comfortable with.

What if the founder gets emotional during the interview?

Slow down, offer a break, and remind them they can skip any question. Their comfort matters more than the story.

Can I add details to make the story more dramatic?

No. Use only the founder’s real words and facts. Honest stories are more powerful than polished ones.