Tony Alessandra‘s journey from a door-to-door cookware salesman to a leader in the SaaS industry is a story of evolution, resilience, and a relentless pursuit of excellence. As a professional speaker who transitioned into becoming a technology entrepreneur, Tony has not only redefined his career multiple times but has also built a thriving business that serves thousands of coaches, consultants, and businesses worldwide.
In our recent conversation, Tony shared the pivotal moments that shaped his entrepreneurial path, the lessons he’s learned, and his advice for others looking to succeed in business.
Discovering a Knack for Sales
Tony’s first taste of entrepreneurship came during his college years, selling cookware door-to-door. “I worked my way through college selling cookware for three summers. It was during that time I realized I had a knack for selling,” Tony recalls. This early experience not only paid for his education but also laid the foundation for his future endeavors.
After earning his MBA and PhD, Tony began his career in academia, teaching sales at Georgia State University. It was here that he encountered the concept of social styles, a behavioral model that would become a cornerstone of his work. “I really liked the concept of social styles, and I started adapting it in my speeches and consulting work. That eventually led to what I called ‘The Platinum Rule’—treating others the way they want to be treated,” he explains.
From Academia to the Hall of Fame
In 1979, Tony took a bold step, leaving academia to become a full-time professional speaker. The decision paid off quickly—within six years, he was inducted into the Speakers Hall of Fame. “It was quick,” Tony acknowledges, but his success was no accident. His ability to connect with audiences and provide practical, actionable insights made him a sought-after speaker worldwide.
During his time on the speaking circuit, Tony continued to refine his approach to social styles, which eventually led to the development of his online assessment platform, assessments24x7.com. “In the summer of 1996, I put the Platinum Rule assessment online, and it won several awards. It took me a little while to realize this could be a business,” Tony says.
Building a Business That Works for You
By 2000, Tony was feeling the strain of constant travel. “I was burning out on the travel,” he admits. This realization prompted him to shift his focus from speaking to building his assessment business. “I wanted to build something I could manage online and sell, unlike the speaking business, which is hard to sell because it’s so tied to you as an individual.”
This strategic pivot allowed Tony to gradually transition from being a speaker to becoming a full-time entrepreneur, growing his business while reducing his travel. “As the business grew, I spoke less and less. In April 2022, I gave my final speech—my ‘mic drop’ moment. I wanted to leave when people still thought I was at the top of my game,” he reflects.
The Keys to Scaling a Business
Throughout his entrepreneurial journey, Tony has made several key decisions that have been instrumental in scaling his business. One of the most important lessons he’s learned is the power of focus. “Early on, almost any opportunity that comes along, you want to jump on it. But as your business grows, you have to learn to say no,” Tony advises. This focus has allowed his company to concentrate on high-potential, high-usage clients, ensuring that resources are used effectively.
Another critical insight Tony shares is the importance of understanding that “expense always precedes additional revenue.” This concept is particularly relevant for businesses that are scaling and need to invest in new people, technology, or infrastructure before seeing a return on that investment. “A lot of people freeze at the thought of spending money because it affects profitability. But you have to be willing to invest in growth,” he says.
Embracing Technology and Systems
Tony’s transition into the tech world didn’t stop at putting his assessments online. Over the years, he has evolved his business into what he describes as a “truly customized assessment technology platform.” This platform not only supports his own products but also hosts dozens of other companies’ assessments, creating a SaaS model that generates ongoing revenue.
A key factor in the success of this platform has been the implementation of robust systems and processes. “When we started bringing on more employees, we realized we needed to have systems in place to manage growth effectively,” Tony explains. This led to the hiring of key personnel, including a Chief Operating Officer (COO) and a Chief Revenue Officer (CRO), who have been instrumental in driving the company’s growth.
Tony is a strong advocate for systems thinking, which he credits with helping his business scale efficiently. “We have an incredible amount of charts, graphs, and exhibits that monitor everything we’re doing. My COO meets with every department head every week to go through their goals and progress. It’s truly amazing,” he says.
Knowing When to Bring in the Right People
One of the more complex decisions for any growing business is knowing when to invest in C-suite executives. For Tony, the decision to hire a COO and a CRO was driven by his desire to ensure the long-term sustainability of his business. “I’m 77 years old, and as I started thinking about retirement or selling the business, I realized that having a strong management structure in place was crucial,” he shares.
His very first and best decision when it came to hiring was when he brought on Brandon Parker to program the assessment site. At the time, early 2000, he was 22 years old. Although he was a communications major in college, he also learned programming. Not only did he do a great programming job, but over the years, Tony saw his potential as a great people manager and nurtured him to grow into his current position as CEO.
Tony’s advice for other entrepreneurs considering this step is to weigh the benefits carefully. “If you’re thinking about selling your business, having the right people in the C-suite is essential. But even if you’re not selling, these roles can add significant value by bringing in expertise that you might not have,” he notes.
For those not ready to commit to full-time C-suite hires, Tony suggests considering fractional executives. “We hired a fractional CMO and a fractional CFO. They bring incredible value without the full-time cost, which can be a great solution for smaller companies,” he says.
The Importance of Profit Margins and Cash Flow
As Tony’s business has grown, maintaining a healthy profit margin and cash flow has been a top priority. “We have an incredible profit margin—currently at 45%—but I’m always looking to improve it,” he says. To achieve this, Tony’s team focuses on one expense category per month, analyzing it for potential savings or efficiency improvements.
“At the same time, we’re constantly looking at revenue—how many leads are coming in, how many are converting, how quickly invoices are being paid. It’s a detailed process, but it helps us stay on top of our numbers and ensures we’re always moving in the right direction,” Tony explains.
The Power of Numbers
Tony Alessandra’s entrepreneurial journey is a testament to the power of adaptability, focus, and a deep understanding of the numbers that drive a business. From his early days as a door-to-door salesman to building a SaaS platform that serves clients worldwide, Tony has continuously evolved, always with an eye on the next challenge.
For entrepreneurs looking to scale their businesses, Tony’s advice is clear: focus on what you’re good at, be willing to invest in growth, and always keep an eye on your numbers. “I learned early on in business not to take my eyes off the money,” Tony says. And with a profit margin of 45% and a thriving business, it’s advice worth heeding.
