Q&A with Scott Lingle: Planting the seeds to succeed

As a kid, Scott Lingle had several side hustles: delivering newspapers, mowing grass, and flipping used bicycles. But it wasn’t until his mid-40s that Lingle jumped into entrepreneurship in a big way, launching the insurance-technology firm Remodel Health with a co-founder in 2015.

Lingle, now 56, has stepped away from day-to-day operations at that company and has turned his attention to a passion project: building a nonprofit, High School Hustle, that helps teens start their first business. The organization is now active in 13 local schools and operates as an after-school activity, set to reach about 1,000 students this year. Teens who earn at least $400 from their hustles receive a $500 investment.

Lingle spoke to IBJ recently about the project and its growth ambitions. This conversation has been edited for length and clarity.

How did High School Hustle begin?

We started with a partnership with Shepherd Community Center, which is a nonprofit on the near-east side. I’ve worked with them for many, many years. And Jay Height, the director, asked me if I could put together an entrepreneurship program for underserved high school students. We then also partnered with another nonprofit called Elevate Indianapolis. In year one, they fed us the kids, and we had 15 students. And the win for us is, can we help a kid build their first hustle and get it to $400 [in revenue]? That’s kind of the north star.

In year one, out of 15 kids, 12 hit the goal. [Last year], a friend of mine came and joined—a gentleman by the name of Peter SerVaas. He’s also an entrepreneur that had an exit and was kind of trying to find his purpose. … And he came along and said, “Hey, I would love to join you, and let’s see if we can 10X this.” So Peter joined, and we then made our first hire, an Orr Fellow, Hunter Beale.

How does it work?

We start in the second semester of the school year, and we run it through May. We meet with the kids six times, teach them the playbook, and then we have a competition for all the Indy-area schools. We call it the $100K Award, and all the kids compete. They have to hit at least $400 [in revenue] for one hustle. That qualifies them for the summer competition. In the summer competition, we give away $100K. How that works is, the top 10 kids in sales get 10 grand each.

Is the $100K Award new this year?

Yep.

What’s a hustle?

A definition of a hustle, in our world, is a business where you can buy all your supplies for $500 or less. You can watch a bunch of YouTubes and figure out how to learn the skills, and then you can start this weekend. So, think car detailing, pressure washing, lawn mowing, babysitting.

What’s the most creative hustle a student has come up with so far?

Couch flipping.

With only two co-founders and one employee, how do you manage all this?

It’s all volunteer based. The model for how we created that is, step one, we said, “OK, we need funders.” We call them chairmen. The chairman is a business titan in Indy that’s built something. They’re probably at my stage of life, and they’ve done really well. … We threw a big party at [Indianapolis venture studio] High Alpha, and we hit up 100 different business owners. We gathered in that room, we cast the vision, and we ended up recruiting about 40 different chairmen, which are the funders for the different high schools. Every high school needs about $10,000 to get it out of the gate.

The next thing we look for is a head mentor. We also call them campus presidents. And head mentor is a business owner, but probably in their 20s, 30s. … And what they want is, they want to be around and learn from the chairmen. And so we recruit them then, and we say, “OK, you’re going to help us launch a new school. … But what we’re going to do is, every month we’re going to have meetups.” … We put on one of those every single month. In addition, we have quarterly meetups that are kind of fun events.

So an incentive for the volunteers is that they get to connect with the other volunteers?

Exactly. … They’re doing good, but they’re also getting a little bit of value.

What’s next?

We want to go national next year. We’re talking about a potential partnership with [the nonprofit group DECA Inc.]. DECA is in most all high schools in Indiana and around the country. … And so next year, likely we’ll expand into Cincinnati, other markets around Indiana, potentially Chicago. … Next year, the goal is, over the summer, we’re going to prove what kind of impact we had on the city with youth, and we’re going to tell that story to a lot of institutions, foundations, endowments—you know, state, local grants. So next year is all about, can we raise money from institutions and governments and endowments and foundations?

You said that the top student last year earned $25,000 from his hustle. How did he do that?

His name is David Arellano. He was an Arsenal Tech High School student. He was a junior last year. He graduated midyear as a senior. He picked pressure washing. [High School Hustle Executive Director] Hunter Beale made one introduction, a guy named Kenny Hall [owner and CEO of local property management company LIV Indy]. Kenny Hall gave [David] gutter cleaning for [all of LIV Indy’s properties], and that’s how he made $25,000. So we think a huge part of this is, kids really don’t understand the value of networks and social capital, and so not only are we teaching them the playbook, we’re surrounding them with mentors. And we’re helping them make those kind of connections, which may be the most important thing.

What’s your best advice about networking?

Always go into that thinking long-term relationships and thinking, “How can I add value?” It’s never extracting value—it’s always adding value.

Is High School Hustle only for kids who want to be full-time entrepreneurs? Or can other students benefit, too?

We see three outcomes. We think the David Arellanos might be 2%, 3%. David is going to go on straight out of high school and become a full-time pressure washer. We think he can make up to $100,000 a year right out of high school. That’s very, very rare. We think a big percentage will say, “Hey, I want to go to college. I want to get a career.” And we think this will help them level up to get into a better school, get a better job. … And then we think a lot of them, maybe a third, are going to be like me, where I had side hustles in high school … then I went to corporate America and stayed there for 20 years. … This won’t be their path straight out of high school, but it’ll plant enough seeds that they’ll come back to it someday. And we’re just trying to plant those seeds.

Are entrepreneurs born, or can they also be made?

I think primarily born. … But what holds them back is fear. And what we’re trying to do is, one of our core values is overcoming fear. We call it faith over fear. And it’s getting these reps in early where they’re doing stuff in real life, knocking on doors, trying to do hustles, make money.

Reps, like repetitions in a workout routine?

Yes. Just practice, you know? Hustle is the antidote to fear. The more you practice and build this muscle of trying things, failing, learning, iterating, the more you’re going to overcome fears.

Why are you doing this?

I believe entrepreneurship is the great equalizer. What I mean by that: I think it rewards grit and hustle and risk-taking even more than IQ and privilege. My heart breaks for underserved kids, and what I want to teach them is, you know, when I grew up, it took me a while to get to this place where I had a growth mindset. My [original] mindset was like, “You’ve got to be really smart if you want to be very successful and grow a large business.” But the more time went on, I realized that, you know, if you have a growth mindset and you’re willing to put in the work and learn, learning is key. It doesn’t matter what your IQ is or what kind of privilege you were growing up with. You know, you see it over and over and over again. The kids bust out of these systems by putting in hard work, hustle and learning. So that’s what we’re trying to bring.•