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.
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.
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.
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.
After the interview, shape the founder’s answers into a short story using this outline:
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.
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.
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.
The question brings out honest, specific advice that beginners can use, instead of general tips.
Three to five is a good range. Pick the ones the founder speaks about with the most feeling.
Yes. With the founder’s approval, a short letter to their first-year self is a warm, memorable format.
Written By
Darlene Gagnon is the founder of WeKinnect Global Branding Agency. Guided by the core value of Service before Self, she works with entrepreneurs and family-owned legacy businesses. She focuses especially on restaurants, arts, and travel and tourism. Darlene writes on Branding, Positioning, Marketing Strategy, Public Relations, Storytelling, and Entrepreneurship. WeKinnect serves entrepreneurs and family-owned legacy businesses across restaurants, arts, travel and tourism, banking, home services, nonprofits, and the pet industry, and Darlene brings that same spirit of service to every piece she writes.
