The Wine Fest: How I Followed My Passion To Create A Legacy

Crystal Newsom
Book Bites
Published in
4 min readSep 30, 2021

The following is an excerpt from Freedom Street by Scott Danner.

Making an impact and creating a legacy is easy and much more fun if it’s based on whatever you’re passionate about. I know what makes me happy: serving people, planning and throwing events, and wine. When I tied them all together, the wine festival was born.

That first year, I was a sponsor too — figured I had to be if I was going to get other people onboard. I was young and wasn’t exactly rolling in the dough, but I was willing to invest $1,000 of my own money in the event. In that way, by “putting my money where my mouth was,” I could talk to people without feeling like I was asking for a handout — I was inviting them to join me in an event that had the potential to make a real difference in our community.

I still make a financial contribution every year by sponsoring the tickets. Our business is on the back of every ticket sold for the event, so in addition to combining all my other passions, I’ve squeezed my work into the festival too. I will tell you, when you can combine everything you love about your life — the work, the people, and the passions — you’ve hit your sweet spot.

Ask These Questions of Yourself

Think about that for yourself. What do you love about your work? What are you passionate about? Whom do you care about and want to help? How can you tie those together to make an impact that gets you excited and means something? If you can figure that out, you’ve found your purpose in life, and you can make an impact right now and in the future.

You can create a living legacy. As you’re building this legacy, your platform grows. The larger your stage gets, the more room there is to invite others to join you. Then, not only does your impact grow exponentially, but the people who choose to join you will also experience what you’re feeling — the joy of making a positive difference in the world.

For the wine festival, we set up “corporate chalets” which are large tents that companies sponsor so their people have a place to gather. Between 80–90% of the sponsors return every year, and we get new sponsors to reserve the remaining chalets. Inviting people from other businesses makes it easy and fun for them to share in the impact you’re making.

With the wine fest, the majority of our sponsors are businesses. Since people are there with their families and coworkers, there’s accountability and sheer ownership for the success of the event. Everyone has a good time together while making an impact for the community. It’s a terrific opportunity to meet people and build relationships that continue after the event ends.

What I’ve Learned from the Wine Fest

Giving without expectation is one of many lessons the wine festival taught me. I also learned a lot of business lessons, because I was rubbing shoulders with some very successful people in the community. I had to learn how to respectfully navigate the room so to speak, giving people roles without making them feel diminished, backing down at times to empower others to make decisions, and stepping in to call the shots when necessary.

I learned how to deal with the adversity that comes with working with many people, and with more obvious adversity — like weather. Twice we held the festival on the day of a hurricane, and twice a nor’easter threatened to take down the event. When Hurricane Sandy created a state of emergency, we opened the gates at noon, just as the wind picked up and the rain began. We were lucky — the gusts weren’t strong enough to tear down our tents or shut down the event.

Hurricane Matthew was worse. Even though it wasn’t supposed to hit our area, I spent the week prior putting together a contingency plan, and I almost canceled it. The wine festival is a rain or shine event, meaning the money for the tickets has been collected and there are no refunds.

Then the weather report changed, and it looked like we might get a taste of the storm in the late afternoon. I moved the event up an hour to 11 a.m. and held my breath. Well, Matthew hit right on schedule from the south, colliding with a nor’easter from the north, and delivering a much worse storm than anyone expected. We lasted until 4 pm, when lightning shut us down.

We got everyone out, and I remember standing in three feet of water and hurricane wind gusts, trying to salvage the tents that were getting torn apart. Special Events, our tent partners lost forty tents in the storm, but we netted $100,000 for charity. You will deal with hurricanes in business, in your personal life, and when you’re trying to make an impact too.

But if you have the right people around you, processes in place, and a contingency plan, you will weather a lot of storms and still manage to find a lot of success.

For more advice on building a legacy, you can find Freedom Street on Amazon.

Scott Danner is the CEO of Freedom Street Partners, a practice that supports financial advisors in their next career step and helps them explore all available paths to secure a fulfilling future. After fifteen years practicing on an employee platform, Scott founded Freedom Street and took it from $0 to $2 billion in assets under management in just five years. Scott is the co-founder of the Chesapeake Virginia Wine Festival and enjoys traveling the country with his wife to watch their two sons play soccer.

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