From Bull Riding to Racing: The High Risk DNA

I asked Chris to give me the origin story.

If you'd asked him in high school and college if he was going to be running a company, he would have been like "how do you do that?" Not even on his radar.

But when he looks at where he's at today and when he was young, there's similarities. Certain things have followed him all the way through.

Bull riding, race car driving, all high adrenaline, high risk. He's always been a super big high risk taker.

"In high school I was a wrestler. I love being able to be on a team but I like being able to have my own outcome by the work I specifically put in. It's a contact sport, not for everybody," Chris said.

In college he was on academic probation, off academic probation, on academic probation. He was more interested in playing the social game, really wasn't committed to school.

He grew up in Indiana farming community. His grandpa was a retired farmer and snowbird in Phoenix, Arizona. When Chris visited at 16, he was like "whenever I get out of school, I'm going there." Once he left college, he went straight to Phoenix.

He didn't know what he wanted to do, floundered around a little bit. He met a guy into bull riding. He was like "cool man, I grew up on a farm and around cows, I should be able to do this. I was a wrestler, I got good balance, I was not afraid to do anything."

He couldn't make a career out of it, but he got a lot of great memories, got in a lot of fights, was broke for a few years.

Racing is something they've done forever. Indiana has two things really important: basketball and race car driving because Indianapolis 500 is the largest single day event in the world. He tried to chase that down, but it's a really expensive sport if you have no sponsorship money.

"I've never been afraid of hard work, digging in and trying to get something. When I want something, to do something in my brain, there's no way I'm going to fail because I'm going to put in the effort. Just like when I wrestled, no matter how my team finished, I could dictate my own outcome," Chris said.

The Winner Mentality From Day One

I asked if he's had that winner mentality since birth, did that come naturally?

Chris thinks he's just always had it. You're not thinking "oh man I'm a winner." It's just "I'm not going to lose."

You can't fail if you don't quit. You just keep going.

His freshman year high school wrestling, he took a whooping the whole year. Not because he wasn't scrappy, but there were kids more technically savvy.

He could either quit or learn. If he's scrappy that's half the game, but if he just could learn the technique then he would be good.

He came back sophomore year and absolutely crushed it. From there it was off to the races. But he put in the work because "I'm going to win, I am not going to lose again." They crushed his ego freshman year.

From Yellow Pages to Building the Foundation

Chris learned he was good at sales. If you're good at sales, you can make some pretty decent money depending on who you're with. He learned that blue collar was kind of his people because he grew up from the country. Plumbers, electricians, air conditioning companies, these are his people. How he grew up.

He was just more comfortable talking to blue collar versus white collar.

His first marketing or sales marketing job was the Yellow Pages. The Yellow Pages phone book, but it was just starting to introduce online Yellow Pages, which is what he really gravitated towards.

When you think about data analysis (really important in our worlds today), when you're racing cars, data analysis is everything. You're studying the data from the car that's giving back to you. Can I brake later going into a turn? Could I have rolled off faster in the middle of the turn? You're trying to pick up speed to figure out where are you slowest and where can you be fast.

In bull riding it's the same way. You study the bull and the bull's patterns and habits, then you create your game plan based on that bull's patterns and habits. The bull's going to come out the gate and go right, you know that, you can position yourself to be ready for it.

It's just studying the data.

"That's what I liked about online advertising: it actually gave you more information to study to feel good that it was actually good for the customer. The last thing I want to do is go look at this plumbing company owner in the face and say yeah keep doing this because it's working great but not really," Chris explained.

He got really good at that. He was early to the game (2002, 2003, 2004). Then he got poached by another Yellow Page company called YellowPages.com at the time, which was just purchased by AT&T. It was to help open the Phoenix market and then also went up to Portland to help open that market.

He focused on home services and home improvement companies. He was just really good at selling them, but he could track it.

At one point what he was selling wasn't happening on the back end. It wasn't that he didn't believe in the product, he just didn't believe in the execution.

He told his wife: "We can do this on our own. I can sell it, we can build it."

Starting RYNO: The Grind That Built Everything

Chris started learning. He told his wife: "I'm really good at selling this stuff in these major metro markets. Imagine if we just move back to Indiana where I'm from. We'll be way early in the digital marketing game."

He talked her into moving back to the Midwest for two winters. They launched the company then. It was called Brickyard Marketing back in the day. The reason they named it Brickyard: they wanted everyone to know they were local, and the nickname of the Indianapolis 500 is the Brickyard (the Indianapolis Motor Speedway is called the Brickyard).

He literally just picked up the phone and dialed, set appointments, then would go run the appointment, sell them, then come back and they would build the websites, do the search engine optimization (which he learned early on), run the paid ads. Just him and her.

They started there.

It segues into the HVAC world because Carrier Corporation is a major manufacturer of heating and air conditioning units. Their headquarters is in Indianapolis, Indiana, like 15 minutes away from his office.

He was really successful with air conditioning contractors. Here's why: one thing he had learned from those yellow page days was the call tracking numbers. Making sure he didn't rely on them to listen to the tracking numbers, he listened to them himself.

"That way I could hear how is what I'm doing for them specifically actually working, and how did they perform on the opportunity I brought them. So when we have monthly conversations around performance, we weren't guessing, we're talking about the facts. Then you can attribute a number to it," Chris said.

If they spent $10,000 a month with him and he had 100 leads, he knew what his cost per lead was. Then they sold it, they knew what the return on investment was. They knew what their accountability was in it and he had his.

They just took their time building it. He was literally building the campaign, selling it, doing the marketing, listening to all the phone calls, putting it in the spreadsheet.

That was a grind, but it was setting the foundation for everything.

That's when he realized: if I only did HVAC every single day, nobody will be better than me because I'm early to the game, I'm only focused on it, doing no other industries. The occasional HVAC also offered plumbing and electrical but not scale like it does today.

That playbook is scalable all the way across any other vertical in that space. He didn't learn that till later on.

The Critical Error: Not Charging Enough

I asked about nightmare stories in the first few years.

Chris made the critical error of not charging enough for the effort and the work he was putting in. His thought process was: come in as a low cost option to get the business just to start, then he got afraid to raise his own costs when really he probably could have charged four times the amount.

He was doing a lot of work for very little margin. He did that for like a couple of years until he was finally ready to increase prices.

"That's probably the biggest pain point I had out of the gate. With every other business that I've invested in or I'm a part of today, that is always the first thing I think about: let's charge what we're worth, not what we think people think we're worth. Let's charge for the value that we have to offer," Chris said.

I asked if that's a universal problem.

Chris thinks it's been a problem for a long time. It's getting significantly better because people are talking about it on a lot of different platforms. But there's still people who want to come in as a low cost option because that's where their mind's at. The easiest way to sell something is to be the cheapest option. That's not the answer.

First Hires and Early Scaling

Chris's wife loves to tell this story. Their first hire she didn't even know. Their first hire was actually a salesperson. He met with him and hired him without telling her. He didn't really realize he had to fill out all those paperwork and do all this stuff because he didn't know.

He made his first hire because he wasn't able to continue to sell at the pace he was selling and build and get these things done. They would collect half payment up front for a website build, didn't get the other half till he was done. He was starting to outsell what he could actually execute on.

"I was like okay, I just need somebody who can do half as good as me. If they can do half as good as me, I can start executing on this thing. So our very first hire was another salesperson. And then the second hire was somebody to help with SEO. Those are my two hires. Really I was just trying to get time back to be able to do the things that I'm best at," Chris explained.

The $30M Decision: Bringing in Private Equity

Fast forward to a few years ago, they had a big merger. I asked Chris to talk about that.

He launched the business in 2008 (technically 2008, really 2007, but they didn't know they had to register a business name, they learned business by being in business).

When you work with big players, you start to learn different games. Being around different people, different circles like Tommy, you start to learn different levels of the game you're playing that you didn't know of before. Like private equity.

When he first heard private equity, he didn't know what that meant. It wasn't on his radar on how to use it. Once you get the business to a certain size ($20, $30 million), that's very difficult to say "I'm going to grow to $50 million."

"It was hard to get to 20. It was hard to get to my first million, then the five million number, then the 10 million number, then getting from 10 to 20 million. Very difficult to get there. And then for me I couldn't think: how do I take this thing from 30 to 50? Where am I going to get that?" Chris said.

It was the right time to make a responsible decision. He had learned over time, especially with his partnership with Gary Vaynerchuk, what he needed to be looking at and what actual tools he could use to scale this thing.

At some point you have to bring in people who are smarter than you to take on all these jobs (which they've done). He thought: there's people much smarter than me at how to scale this thing. That's a responsible decision for him and his wife Anna to make because they have an obligation to all these employees to help them continue to have new opportunities to grow, make more money, career advancement.

The responsible decision was: bring on somebody smarter than me to help us scale it. I could still do what I'm best at, but I need somebody to actually run the business.

They brought on a private equity partner in 2023 after 18 months (excuse me, 14 months) of researching and meeting with different opportunities.

The whole plan was to bring on a private equity partner to scale. People think "oh you sell the business, you sell the business and you're out." That wasn't their play. Their play was: bring on private equity who knows how to run the business side of it and then let us do our thing at this scale.

But now that he's learned the game, it's like: oh I can continue to scale and now I know how to go and bring other smaller companies into our mix that makes it successful for them but also successful for us. Either they offer something we don't or maybe they're better at something than we are or maybe they're in a different vertical industry we're not in, so it's an easy add-on to the business.

He has the entire back end to do everything, he just needs the entry into the vertical.

"You learn the game along the way. When I first started this business, that was not even on my radar, buying a company," Chris said.

The Gary Vaynerchuk Handshake Deal

I asked Chris to tell me about the three year partnership with Gary Vaynerchuk.

Chris followed Gary's content. When he just started listening to podcasts, Gary's was the first (back in 2016, 2017). Gary was starting to do some events here and there, so Chris went and watched him at one event.

One thing that's really important is giving back, one of their core values. Every month, one Friday every single month to this day with all these people, they still have four hours a day on a Friday once a month where they go and do community service. Big core value.

That also got them into this relationship with the then Arizona Cardinals football coach Bruce Arians. They got involved with his foundation. Chris was building an app at the time for phones, so he built an app for Bruce's foundation and they just donated to him. That kind of started a relationship.

Then they got in that athlete circle. Once you get in, you have some trust. People refer you to one another.

Gary was just starting to get Vayner Sports going with him and AJ (him and his brother). They were coming out to meet with one of the Cardinals players and also doing a dinner.

Chris was reaching out for months trying to get in contact with Gary. When he heard Gary was coming out, he was like "this is my opportunity."

He was able to get into this dinner with them. He was talking to them and said: "Hey man, I hear you're trying to get this (they called it Vayner Mentors back in the day, they were just getting it off the ground). They were trying to work with other companies. Fortune 500 was kind of their niche at the time, but they were doing nothing with SMBs. This was their attempt.

"I said: hey, why don't you leverage me? You're not working with agencies, why don't you use me as an agency as your guinea pig? Learn how to make this program work. And then I'll leverage you to pull you into the home services space so they can hear what you're talking about, listen to you, get to know you. Let's do this," Chris explained.

They did a handshake deal that night. Chris still has the video from that night where they took his phone and recorded it. He shared it with his team on Monday the next day.

They put together the handshake deal. Two months later they had the contracts laid out. They decided to do a three year deal together.

It was fantastic. Today Chris is still great friends with Gary.

He learned a lot from Gary. Not just on how to go after social, but how to go after voice search (the voice search game was coming up, so they learned those tactics from him). They learned the operational side of the business: if we're going to get to $40 million, what does the scale need to look like? What do the bodies need to look like?

Gary's the one that talked Chris into launching the podcast. That's why he did it in the first place. Gary helped and came on multiple times. Chris went on Gary's podcast.

"It was great man. I was like a sponge soaking up everything from him. At the end of the day when it was over, it didn't make sense for them to buy the business (at least not to us because we thought we could do more), and we just parted ways and we've been friends," Chris said.

It was just one of those deals where he made it happen. Same thing with wrestling: you can be on a team but you gotta put in the work to go make it happen. Bull riding: you go and study the bulls to make it happen. Racing: you study the data to make it happen. He was never afraid to do the work to win.

The $92M Empire: Four Companies Combined

I asked Chris how it feels going from that startup agency to now being a massive empire.

Going from two people or even 10 people to now 300 plus, yeah it's a different beast. The game changes even when you're over 100 people because now firefighting is a constant position.

When you're a bigger company, you're certainly a target. You have delegation, leadership, management, different layers of leadership. You're no longer the one.

Today Chris asked his wife (she's still in this business, runs all of home services, runs all the operations): "Hey I have a question, who do I go to?" He didn't even know who to go to. She told him the person and he didn't know the person.

"I feel bad about that because the way I came up was we're very personal, very close, great culture here. But you can't know everybody. When we had 100 people I knew the 100 people. 300, that's very difficult. So the business changes," Chris said.

My Main Takeaway

The biggest lesson from talking to Chris is that building a $92 million agency empire isn't about tactics or marketing genius. It's about being willing to do the hard work nobody else wants to do, studying the data like a race car driver, and never being afraid to admit someone else is smarter than you.

Chris's winner mentality transfers across everything. His freshman year high school wrestling, he took a whooping the whole year. He came back sophomore year and absolutely crushed it because "I'm going to win, I am not going to lose again."

The foundation that built everything was the grind: literally building the campaign, selling it, doing the marketing, listening to all the phone calls himself, putting it in the spreadsheet. That set the foundation for everything. If I only did HVAC every single day, nobody will be better than me because I'm early to the game, I'm only focused on it.

The critical error almost everyone makes: not charging enough. Chris's thought process was come in as a low cost option, then he got afraid to raise costs when really he probably could have charged four times the amount. That's the biggest pain point. With every other business he's part of today, that is always the first thing: let's charge what we're worth, not what we think people think we're worth.

The Gary Vaynerchuk handshake deal happened because luck is when preparation meets opportunity. Chris scratched, clawed, phone calls, emails for months to connect with Gary. When the opportunity came up that Gary was coming to Phoenix, he got himself in that room. They did a handshake deal that night (he still has the video). Two months later they had contracts, decided to do a three year deal. Gary's the one that talked Chris into launching the podcast.

The private equity decision at $30 million was the responsible choice: bring on somebody smarter than me to help us scale it. They have an obligation to employees to help them have new opportunities to grow, make more money, career advancement. After 14 months of researching, they brought on a private equity partner in 2023. Now they're a $92 million organization (includes four companies through merger).

The vulnerability lesson is most important: it's okay if you don't know something, it's okay if someone does something better than you. Pride is the enemy. If you can let it go, you'll move so much further faster. Anyone who needs to be right for the sake of being right is the wrong person. I don't know everything, I need to allow people who are smarter than me to do the things they're better at. That vulnerability is an absolute strength.

Want to learn more from Chris? Follow him on LinkedIn, Facebook, and Instagram. Listen to the To The Point Home Services podcast. Visit Rhino Strategic Solutions online. Chris is pretty easy to get in touch with and lives his life on the record.

Listen to the full episode to hear more of Chris's insights on scaling from cold calls to $92M, the Gary Vee partnership that changed everything, why charging enough matters most, and the winner mentality that transfers from bull riding to building empire-level agencies.