The 20 Year-Old Who Built Seven Businesses (And Made Forbes 30 Under 30) | Dylan Capshaw

Most people wait until they feel qualified to start.

Dylan Capshaw started before the world had any reason to think he was qualified at all.

At 11 years old, he launched his first venture, a wildlife rescue that taught him the fundamentals of running a business. By 16, he opened Stemistry, a brick and mortar flower bar and coffee shop, becoming one of the youngest retail owners in the country. Today, at 20 years old, he has built or acquired seven ventures across retail, hospitality, nonprofits, and software, and was named to the Forbes 30 under 30 list.

But what makes Dylan's story remarkable is not just how young he started. It's that he did it without waiting for permission.

While most of us spend years convincing ourselves the timing is not right, Dylan was already building. While others wait for approval, Dylan was learning through failure. While the rest of us overthink the first step, Dylan was already ten steps ahead.

In this conversation, Dylan walks through what it actually takes to start before you are ready, how he leads people twice his age, why he hires people smarter than him, and what happens when your back is against the wall and you have no choice but to figure it out.

He also gets honest about the cost of building multiple businesses at once, the voices that still try to sabotage him, why discipline matters more than motivation, and what he learned from losing control of one of his own stores.

This is not a conversation about hustle culture or grinding yourself into the ground. This is about clarity, persistence, and the willingness to take the first step even when no one is watching.

In this episode:

How Dylan started his first business at 11 years old

Why his parents let him raise exotic animals in their backyard

What a wildlife rescue taught him about running a real business