What advice do experienced entrepreneurs give beginners? Ask them what they would tell their first-year self, and their answers become practical advice for new founders.

Experienced entrepreneurs often give their best advice when asked one simple question: “What would you tell yourself in your first year?” The answers are honest, specific, and useful. This post gives you interview questions and a story template to draw out that advice from real founders and share it in their own words.

It works for every kind of founder: restaurant owners, artists, travel professionals, bankers, tradespeople, nonprofit leaders, and family business owners looking back across decades.

Below you will find ten questions, a simple five-part template, and ideas for each kind of business.

Why this story matters

Beginners are hungry for advice, but general tips often feel distant. Advice from a real person looking back at their younger self feels personal and trustworthy. It also helps experienced founders reflect on how far they have come.

For family businesses, this story can become a letter to the next generation.

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 first year 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.

• Picture yourself in your first year. What were you worried about?
• What turned out not to matter at all?
• What mattered much more than you expected?
• What is one habit you wish you had started earlier?
• What is one thing you would stop doing sooner?
• Who would you tell your younger self to spend more time with?
• What did you learn about money that you wish you had known?
• What did you learn about people?
• What did you learn about yourself?
• If you could write one sentence to your first-year self, what would it say?

Story template

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

• Then: A picture of the founder in year one.
• The worries: What they feared then.
• The truth: What really mattered.
• The advice: Three to five pieces of advice in their words.
• The letter: One sentence to their first-year self.

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 what they would tell themselves about hiring and hours.
• Artist: Ask what they would say about pricing their work.
• Travel professional: Ask what they would say about busy and slow seasons.
• Banker: Ask what they would say about building relationships.
• Tradesperson: Ask what they would say about saying yes to every job.
• Family business: Ask an elder what they would tell themselves when they first took over.

Where to share the finished story

Once the founder approves the draft, think about where the story about their first year 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

When founders share hard-won advice, they are serving the next generation. That is Service before Self: giving away what they learned so others can avoid the same struggles. Encourage readers to pass the lesson on by writing a note to their own first-year self, or to someone just starting.

Your Next Step This Week

1. Invite a founder to share what they would tell their first-year self.
2. Use the ten questions and capture three to five pieces of advice in their words.
3. With permission, write it as a short letter and share it with new entrepreneurs.

Frequently Asked Questions

Why ask founders about their first-year self?

The question brings out honest, specific advice that beginners can use, instead of general tips.

How many pieces of advice should the story include?

Three to five is a good range. Pick the ones the founder speaks about with the most feeling.

Can this be written as a letter?

Yes. With the founder’s approval, a short letter to their first-year self is a warm, memorable format.