How to Build a Multimillion Dollar Business: Stories from Entrepreneurs Who’ve Done It

Relatively few companies ever make it to the $10 million mark. 

The reasons are varied — they’re happy being smaller, they sell before they get there, they struggle to transition from small to big. 

What does it take to cross that golden line? 

We sat down with three long-time Trajectify clients to talk about how they became multimillion dollar businesses and what other entrepreneurs can learn from their success. 

Lisa Robinson, Founder and CEO, My Independence at Home

Lisa Robinson didn’t start out with a number in mind. In fact, she didn’t want to think about the numbers. 

After spending eight years in the Army and twelve years in the finance industry, Lisa’s entry into homecare was something of a coincidence. She’d transitioned to freelance writing, and during this time was asked if she’d be interested in working in homecare. 

Lisa ran a division of the agency for over a year. She loved the work, but she was frustrated by their approach — focused too much on money and not enough on client care. 

Lisa worked diligently on her home care application and in November 2013 received her home care license, quit her job in December and had her first Participant in January 2014.

“In the beginning, my focus was just on providing quality care to low and middle income individuals,” says Lisa. Her agency primarily served minority populations, and she wasn’t really thinking about growth. 

So how did that happen?

“I give all the credit to my team and our caregivers who are providing care in the homes,” Lisa says. Much of their early growth was the result of word of mouth marketing. 

Though Lisa downplays her own strategic focus, she has taken specific actions to achieve her growth goals — especially around marketing and company culture. 

One of their big milestones was reaching 100 participants. They had a big thermometer on the chalkboard in their conference room, and they were filling it in as they got closer to their goal. The closer they got, the more Lisa realized she’d have to invest in marketing. My Independence at Home now has billboards throughout the city and ads on the radio. Lisa also started doing more speaking engagements. 

With close to 300 employees, Lisa put a lot of energy into creating a family oriented company culture.

Lisa’s case managers and schedulers regularly communicate with Participants, and Lisa often writes handwritten thank you notes to those who have done a good job. My Independence at Home hosts lunch and learns, volunteers in the community and gives gift cards for those who have gone above and beyond.

Lisa believes her leadership style is firm but approachable, something coaching helped her develop. “Mike was able to help me focus on being a CEO and to learn how to lead better — not letting passion drive the business,” says Lisa. “I had to better understand how to harness my emotions, learn to hold my team accountable, and to be comfortable with disciplining or terminating when necessary.”

Lisa also needed help with her finances. One of her biggest challenges — one that’s faced by many minority-owned companies — is access to capital. Lisa was at the mercy of non-traditional lenders who had exorbitant repayment terms. 

She was just using debt to pay debt. 

“We were just bleeding money,” she says. “I was worried that we wouldn’t be able to turn the tide.” 

She started working with an outsourced CFO that connected her with PIDC Philadelphia. PIDC helped her eliminate the company’s debt.  

My Independence at Home did almost $7 million in revenue last year and will be close to $8 million this year, but the financial success feels a bit like a bonus for Lisa. “I always tell my team, we don’t focus on money, we focus on quality compassionate care.” 

See: Build for Sale or Build for Growth

Jim Lockwood, Co-founder, COO, and VP, The Lockwood Group 

Jim and his father James started The Lockwood Group as a consulting outfit for companies wanting to break into different aspects of the Department of Defense. James had military background and contacts. Jim had business acumen. 

Today, The Lockwood Group delivers global professional services to the Department of Defense to improve the mission readiness of their customers with a core competency and functional expertise in the area of logistics, engineering, and program management.

Back then, in the late 90s, they knew it would take about 18 months to win their first professional services contract, so they used that time to figure out how to get started and brand themselves. It’s one of the things Jim thinks they did really well in the beginning. 

“We thought strongly about the brand, about what problem we were trying to solve,” Jim says, “and then we tied our brand directly to improving mission readiness.” That has remained their central focus as they’ve grown to a global professional services firm with a team of about 75, two core locations, and team members at more than a dozen sites alongside military clients.  

“That first contract validated that we could be a player in what I would call a micro market of the macro market,” says Jim. “We did that several times — built a profile in a micro market.” Each time they took success in one micro market and generated it in a new market, they built on that proof of concept. 

They’ve had to evolve along the way, and they continue to do so.They began outsourcing and building out the organization early on. Up to about $5 million, they mainly outsourced. Between $5 and $10 million, they started to build a team.  

About five years in, they created a vision of what the organization would grow into, with a two-sided organizational chart — an operational side and a service delivery side. They hired at senior levels in conjunction with that org chart. 

What’s Jim’s hiring philosophy? 

“Hire good people and put them in the seat where they’re best equipped,” says Jim. “Then retool the organization at the level below macro to surround that person with the areas they’re good at and give them accountability.”

Now, says Jim, they’re starting to bring even more team members inside the organization. 

They have a strong culture and core values at this point, but Jim wishes they’d focused more on that in the beginning. 

“The foundation of the organization is people,” says Jim. “That should be where you start.” 

Jim and his dad spent about a year working on their core values, going a little deeper and iterating many times. They came up with six that continue to be their guideposts. 

“I’m a big believer in mindset and bringing the right attitude. One of our core values is positivity,” says Jim. “We try to build our culture around that environment. It’s about building people up.”

The company starts off their monthly meetings with kudos moments — and not just from the top. They pass the microphone around the room so everyone can share a “thank you” or a “well done.”  

The organization is fluid and evolving, and they’re gearing up for the changes that come after hitting the $10 million mark. “Even today, the proof of concept’s evolving,” Jim says. “As you get to different sizes, you have a whole different space of competition, and you’ve got a new proof of concept to develop.”

Jim’s main challenges are time management and prioritization. Sales is his best skillset, so he tries to focus on that and stay in his lane. 

Coaching helps. “If I’m not getting leadership or coaching or something above me, I’m not growing,” he says. “Then how can I grow the people below me? I really don’t see how someone at a leadership level does not have coaching. If you’re a leader, then you’re coaching below you.” 

See: Developing Your Employer Brand: How to Attract High Performers

Mike Risich, Founder and CEO, BOLT ON Technology 

In the mid to late 90s, Mike Risich was teaching a Microsoft Excel class for a community education program. An auto shop owner took the course to help with organization at the shop. “From that point on,” says Mike, “I was infatuated with trying to help auto repair shops solve their problems.” 

He was building software for auto repair shops as a side hustle until 2005, when he quit his day job. At that point, around 150 shops were running one of his earliest programs, and he was making enough subscription revenue to replace his day job salary. 

Mike was plugging along, building his client base, until the recession hit in 2008. There was a serious contraction in the marketplace, and it was a scary time. Fortunately, Mike connected with two business partners who owned and operated about a dozen tire shops in the Philly market. 

“Now I had somebody who was supporting me and saying, ‘I want you to put everything you dream up into my stores,’” he says. That confidence from someone else provided Mike a lot of reassurance about what he was doing. 

Then in 2009, one of the business partners had a catastrophic loss. His store burned to the ground. Mike became the general manager of 12 tire stores overnight. 

“I got a world-class education in how the operation of repair shops and tire shops really works,” Mike says. “I got to see all the flaws. Then I started introducing some of these tech solutions as a way of bridging the gap so that we could have better service for the customers coming into those tire stores. And before long things really started to mature and exceed even the expectations that I had.”

Their customer retention improved, and their customer acquisition costs dropped. They were onto something. 

In June 2012, Mike connected with two big name brands in the industry — Mitchell1 and NAPA — who put their stamp of approval on BOLT ON’s technology and started selling it themselves. That was the tipping point that propelled their success, “almost overnight,” says Mike. 

By the end of that year, BOLT ON’s technology was in 1400 shops, and the company had grown to seven team members. They doubled in size almost every year after. 

“I kind of embraced it,” says Mike. “I was getting leadership coaching from Krupit, who challenged me. He said, ‘Did you build this business to just be you? No? Then hire people.’” 

“Those initial hires were pretty crucial,” he says. Hire number one and number two are still with the company, which is really exciting.” 

Mike had to quickly learn how to be a leader. In addition to getting a coach, he started reading books and listening to podcasts on leadership. Getting explicitly clear in his communication and setting appropriate expectations have remained two of the most important lessons. 

Mike had been doing everything himself for so long that he thought he could do it better than anyone. A conversation at a CEO peer group meeting helped him understand that he was setting expectations too low for new hires. Instead of seeing them as half as effective as him, he should see them as 3000 times as effective as him. After all, they would be focused on a single task whereas he had been wearing multiple hats. 

Now, over 2 million inspections a year go through BOLT ON’s system. 

“There were some moments along the journey where you're literally pinching yourself, like, is this happening?” says Mike. “And it's fun to celebrate. It's fun to be rewarded with a great team who is equally passionate about solving this challenge.”

BOLT ON was acquired by a private equity firm at the beginning of October. It was an acquisition as well as a merger, and Mike was asked to lead the combined entity. He’s now one month into leading a team more than 150 strong accountable for significantly higher revenues. 

See: How Does the Acquisition Process Work?

Final thoughts

Talking with these entrepreneurs, there are a few clear through-lines. 

Entrepreneurs that build multimillion dollar businesses focus on their people — hiring well and creating atmospheres where employees want to work.

They build a brand within their markets. The question “why would I want to buy from you” has been answered. There is a focus on consistent communications.

They change direction or tactics when they need to. They’re willing to incorporate something new that they didn’t expect. They see their business and the way they operate it as something fluid and dynamic, not static. 

Entrepreneurs who succeed ask for and accept help. They work with coaches and advisors. They seek partnerships. They outsource tasks. They don’t go it alone. 

We’ve been proud to support these entrepreneurs on their journeys. Contact Trajectify if you’d like to discuss your vision for multimillion dollar success.