Kevin Gillespie

Co-Founder of Headline Solar

Kevin Gillespie is the co-founder of Headline Solar. The 33-year old Chicago native got his start in entrepreneurship in 2012 after bringing his drum invention to market. After that, he started Wax & Wick, a high-end candle company, in 2015. In early 2019 he helped launch Headline Solar in Illinois. Illinois is a great market for solar energy, not only are the residents able to help the environment but the cost to go solar has been greatly reduced by the Solar Renewable Energy Credits available.

Kevin is an active member of his community and continuously advocating for clean energy throughout Chicagoland. Kevin is currently working with a local school district to create a solar education program for students to learn about the benefits of clean technology with a goal to implement the program throughout Illinois and beyond.

Where did the idea for Headline Solar come from?

Jared and I had been talking about how generating leads for companies was a great business but was very unsatisfying. We never got the chance to meet happy customers or see the process completed. Once we had that desire to build something bigger, the fire was lit. We started thinking about how to make a bigger impact and serve others. Headline started in California and moved to Chicago two months after that.

What does your typical day look like and how do you make it productive?

I start the day with our install crews at the warehouse, going over the job and getting materials loaded up. After that is a mixed bag of project management oversight. This includes scrubbing site visits, designs, design follow ups, scheduling, and managing supply chain. I have an amazing team that supports the vision of the company, so we chat throughout the day and fill gaps where we have room. Throughout the day I check in on the crews and support them when needed.

How do you bring ideas to life?

Ideas start with finding a problem and then solving that problem. Whiteboarding the steps to find bottlenecks is the first step. After that it’s a process of testing solutions and simulating their outcomes until we can implement action across our teams.

What’s one trend that excites you?

Automation. I love having the ability to use tech in our business to reduce time wasted on project updates. We can automate virtually any step of the process while building teams of people that really care about the quality of the projects we take on. Automation doesn’t have to completely remove the human element from processes. Automation should be used to support a framework that is already in place.

What is one habit of yours that makes you more productive as an entrepreneur?

Using punch lists to map out my day. If I don’t use a punch list I feel like I accomplish nothing.

What advice would you give your younger self?

Focus on yourself and forget what everyone else is doing. Be the leader. I tell my son to “be the leader” every day. My dad told me the same thing when I was a kid. I just needed a reminder as I got older.

Tell us something that’s true that almost nobody agrees with you on.

Finding balance between family and entrepreneurship doesn’t exist. Those two things blend together and become one big conglomeration. The key to success with this is having support in place. My wife and kids support me, my parents support me, and my business partner supports me.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Delegate the right task to the right person. It’s important to recognize that you need help to achieve your goals.

What is one strategy that has helped you grow your business?

We started Headline Solar with marketing first. If we started with trucks and employees we would have struggled to grow quickly. Starting with marketing first helped us realize that if we had a signed contract we could find someone to install it. Which eventually pivoted to doing all of the Engineering and Procurement ourselves. After that we added installation crews and became a full stack Solar Development Organization.

What is one failure you had as an entrepreneur, and how did you overcome it?

In 2012 I invented and brought a drum product to market with the help of another company. The product was a total failure in terms of sales but I got my name in top industry publications, which satisfied a goal I had as a kid. I pressed on and started an e-commerce brand in 2015 which has done well. And then started Headline Solar in 2018. I overcame that initial failure by continuously looking for new ventures and networking with the right people.

What is one business idea that you’re willing to give away to our readers?

E-commerce. Find a product, read the 1-star and 2-star reviews on Amazon, improve upon that product, and launch it on Amazon.

What is the best $100 you recently spent? What and why?

Apple AirPods, they made it possible to multi-task while talking on the phone.

What is one piece of software or a web service that helps you be productive?

Podio has been amazing for project management. It really helps with transparency during our sale-install process.

What is the one book that you recommend our community should read and why?

Traction by Geno Wickman, the book really lays out great structure for team-building and accountability.

What is your favorite quote?

“When the going gets weird, the weird turn pro.” – Hunter S. Thompson

Key Learnings:

  • Find a way to make a bigger difference in the world and the money will follow.
  • Use punch lists to accomplish your daily goals.
  • There is no balance between work and family life when starting a business.
  • Surround yourself with people who support you.