In 2015, a Chicago entrepreneur invested $5,000 in a CFO side hustle; years later, it became a seven-figure business with 16 staff

Establishing a business from the ground up often begins with identifying a challenge and finding a practical way to solve it. For some entrepreneurs, that opportunity arrives while they are still working another job. For John Frank, what started as a side project eventually developed into Third Road Management, a professional services firm concentrated on helping small and mid-sized organizations handle their financial operations.

Frank says Third Road Management is currently a multi-seven-figure business and has most recently been developing at 15-20% per month. The company started in 2015, after Frank had already spent many years doing similar work as a side project.

From a side hustle to Third Road Management

Frank started Third Road Management with the aim of changing how small to mid-sized organizations see their financial operations.


The concept evolved, when a family friend who owned a commercial printing business reached out to Frank after the company's CFO abruptly resigned. Frank started helping with the business, and within months, he says, the company had made major progress in areas including profits, business visibility, leverage and its overall risk profile.

That experience resulted in another opportunity. A different friend approached Frank for help functioning a business in another industry. After seeing success there as well, Frank says he had an “epiphany” and recognized many things: the work was rewarding, small and mid-sized organizations had a significant gap in strategic, financial and operational expertise, these companies were widespread, and he was not aware of another business doing what he was doing.

Frank started using the term “Fractional CFO” for the service, saying he had never heard the term before. He wanted to distinguish the providing from businesses he viewed as outsourced accounting providers, as well as from permanent and interim placement firms.

Frank's corporate finance background

Before establishing Third Road Management, Frank spent 13 years working in corporate finance.

His career included mergers and acquisitions that involved quality of earnings analysis at Arthur Andersen and leveraged finance at Antares Capital and Denali Capital. He also worked in fixed income sales and trading, such as distressed structured products trading at Cohen & Company and R.W. Pressprich.

Frank received a BS in Finance from the Gies College of Business at the University of Illinois at Urbana-Champaign.

Third Road Management explains its service as a “re-imagined CFO Suite.” The company hires Fractional CFOs, Controllers and Bookkeepers and offers their expertise to clients for a fee. Clients can use the complete range of services or select individual services regarding their needs.

Starting with $5,000

The business was bootstrapped from the start. Frank started with $5,000, which he used to pay an attorney, a graphic designer and a web developer.

The company was legally organized in October 2015. By January 2017, he was working on Third Road Management full-time.

What worked and what did not

Third Road Management experimented with many methods as it developed.

Frank says some approaches were unsuccessful like an early direct-mail campaign, certain SEO/SEM investments and an email marketing attempt that followed a “spray and pray” approach. He believes the SEO/SEM outcomes may have been impacted by limited awareness of the service and says it could be something the organization revisits in the future.

Other strategies generated better results.

Frank says these included sending quarterly personal updates to his network by email, being relatively active on LinkedIn, consistently taking networking meetings and launching The Drive-By Entrepreneur Podcast, which is available on YouTube, Spotify and Apple.

Aiming to become the industry standard

Frank explains the company's “CFO Suite Revolutionized” offering as a solution for staffing financial offices at over a million organizations in America.

He states, Third Road Management will not serve all of those organizations, but plans to pursue the opportunity. From the company's start, Frank says he has told his team that it wants to be the “Goldman Sachs” of its industry, a brand recognized as the standard.

Currently, that focus means citing, “no” to other ideas in order to concentrate on the CFO suite.

Dealing with uncertainty

Frank says he has encountered some degree of imposter syndrome, especially because he recognizes that situations can change quickly.

At the same time, he says the company's ability to hire talented individuals who believe in and share its vision has given him greater confidence in the direction Third Road Management is taking.

Their commitment to the company's vision, he says, has reinforced his conviction in the journey ahead.

Lessons learned along the way

Frank says there have been several life lessons from entrepreneurship to count and points to many familiar principles, including surrounding yourself with people who are smarter than you, hiring slow and firing fast, knowing that culture can eat strategy for breakfast, remembering that the client is always right, and being committed to a company's vision, mission and values.

Frank emphasizes trusting your instincts. He cites that some of his biggest mistakes happened when he ignored his instincts as a decision was difficult or inconvenient.

Another lesson is risk. Frank says entrepreneurs never necessarily stop feeling as though they are forcing themselves “all-in.” In his view, business owners can restrict their ceiling by becoming too cautious and forgetting the challenges they took when they were building the business.

Why the journey continues

Despite the concerns, Frank says there is nothing else he would rather be doing.

He acknowledges that entrepreneurship can involve challenging periods and says there were several days when quitting and taking a job requiring less mental effort would have been simpler. His approach has been to push through those moments and stay focused on his purpose while working toward success.

From a $5,000 initial investment and a side hustle that began in 2014, Frank's journey resulted in the creation of Third Road Management in 2015 and gradually to a full-time business focused on fractional financial services. His emphasis throughout the story remains consistent: build relationships, maintain a clear vision, develop a strong team and remains working toward the purpose behind the business.

Source: Founder Reports