In this episode: Jon Peyton walks through his own entrepreneurial journey, from selling hats in middle school to building an ecosystem of firms for business owners. He’s candid that his hardest struggles were personal rather than professional, and he explains how reordering his priorities changed both his life and the way he leads his team.
Key insights
- Every entrepreneur fails. How you respond to failure decides whether you become a statistic or a success.
- More than 80% of business owners close their businesses rather than sell them. Building to sell (“scale to sale”) starts long before the exit.
- Providing financially isn’t the same as providing emotionally. Long hours at work can cost you at home.
- Jon changed his priorities from work, family, friends, community, self to self, family, friends, community, work. You can’t give your best to others until you’re at your best.
- Delegation is how you keep growing without carrying all the weight yourself.
Episode timeline
- 0:00 Where the journey starts, and where it ends
- 2:34 Jon’s journey, from middle school hats onward
- 3:44 Learning to market yourself, and accepting failure
- 5:48 Scale to sale: why most owners never sell
- 7:13 Understanding the market before you build
- 9:00 The struggle: personal and professional
- 10:34 Providing financially but not emotionally
- 12:09 From cracking the whip to building culture
- 14:33 Reordering priorities: me, family, friends, community, work
- 17:13 What actually starts an entrepreneur’s journey
- 18:24 Keep growing or someone else will
- 19:39 Delegation as a growth strategy
- 22:58 Entrepreneurship isn’t hard. It’s a journey.
The episode in brief
It started small. Jon has tried his hand at business since middle school, when he sold hats his classmates loved. He later chased ideas in the wedding industry and construction. Each time, he saw a problem, enjoyed solving it and wanted to share it. His biggest weakness was marketing himself. As someone who leans introverted, putting himself out there meant risking failure. Every entrepreneur fails, though, and what matters is whether failure weighs you down or fuels what comes next.
One problem leads to the next business. Jon’s planning and investment work kept raising the same question: what happens to the business when the owner is ready to move on? With more than 80% of owners closing rather than selling, he built a consultancy around helping owners “scale to sale.” That means working on the business instead of in it, so that one day they can pass it on or sell it on their own terms. Getting there meant studying the market first: what owners struggle with when they hire consultants, work with them and outgrow them.
The hardest struggles were at home. Jon believed 12-hour days were how he provided for his family. Looking back, he provided financially but not emotionally. When the people around you don’t share your vision, the weight gets heavy, and missed moments add up. Recognizing that imbalance changed how he sees everything.
The lesson carried into the business. Cracking the whip hadn’t helped his family, and it wasn’t helping his employees either. When he focused on inspiring and motivating his team, the culture improved. People invested more in customers and vendors, and he got more time back for the people he cared about.
Put yourself first, and don’t mistake it for selfishness. Jon once ranked his priorities as work, family, friends, community and himself last, expecting that success at work would make everything else fall into place. It didn’t. When he reversed the order to himself, family, friends, community and then work, everything changed. If you aren’t healthy and steady mentally, physically, emotionally and financially, you can’t give your best to anyone else.
Keep growing, and delegate. Entrepreneurs who stop learning stagnate, and competitors notice. The way to keep growing without carrying all the weight is delegation: a trainer, a dietitian, a business coach, help at home, a virtual assistant. When you’re stuck, find someone who has faced the same struggle and learn from them.
It’s a journey, not a sprint. “A long time” can mean months, years or decades. You’ll fail along the way. Embrace it, learn from it and fail upward.
Key action items
- Rank your priorities honestly. List self, family, friends, community and work in the order your calendar shows, then in the order you want.
- Ask what happens to your business when you step away. Write down whether you’d pass it on, sell it or close it, and what would need to change to make that possible.
- Delegate one thing this month. Pick a task at work or at home that drains time you’d rather spend elsewhere, and hand it off.
- Check how your leadership feels to others. Ask your team what would make them want to invest more in the business.
Listen next: Episode 5: Are You Working Hard or Smart?
Value Creation Consultancy™ has since merged into Founder’s Accounting™. References in this episode to the consultancy reflect the firm at the time of recording.
This episode is educational and isn’t legal, tax or financial advice. Speak with your own attorney and advisers about your situation.