By: Jay Kt
Growth can expose weaknesses in a business that were easy to overlook when the company was smaller. A founder who once handled everything personally suddenly has employees to manage, expenses to control, and decisions that affect far more than their own workload. The skills that helped launch the company may no longer be enough to sustain it.
Vivienne Reign knows that transition well. A healthcare entrepreneur and business operator, she has built and sold businesses that generated more than $200 million in total revenue before she sold them in 2023, and she partnered with physicians to launch and scale hundreds of medical clinics nationwide. One of her businesses generated more than $200 million in total revenue before she sold it in 2023.
Her understanding of leadership has developed through decades of building companies, learning from experienced entrepreneurs, making expensive mistakes, and occasionally discovering that the best advice comes from people working alongside her.
Through those experiences, Reign has developed a perspective on business mentorship that places considerable value on independent judgment, preparation, and the ability to keep moving when circumstances become difficult.
The Childhood Experience That Shaped Her Ambition
Long before she started building companies, Reign encountered someone whose success changed how she thought about her future.
Her father’s cousin was the first person in their immigrant family to achieve substantial financial success. Her parents had established comfortable careers in aerospace, providing a stable upbringing, but their relative had created a lifestyle that fascinated her.
She remembers his Mercedes, his casual clothes, and the portable cell phone he carried in a small case. She also remembers the restaurant where he took the family to lunch, particularly the peanut shells scattered across the floor.
What stayed with her, though, was the independence his success appeared to provide.
“I decided in that moment that I would work hard enough to buy my freedom: to be who I wanted to be, go where I wanted to go, buy what I wanted to buy, and do what I wanted to do,” Reign recalled.
Her father’s cousin probably never knew the impression he made.
Years later, she still considers that experience an example of how entrepreneurs can influence others without deliberately trying to teach them anything.
Learning When to Trust Her Own Judgment
Reign has worked with accomplished entrepreneurs and observed different approaches to leadership. One quality she consistently recognizes in successful business owners is their willingness to make decisions independently.
“The ones who succeed aren’t imitating anybody. They trust their own judgment and act on it,” she said.
That belief influenced one of her most significant expansion decisions.
Reign wanted to grow a business to 100 offices. After opening eight, she recognized that continuing to expand through the same model would make reaching her goal unnecessarily difficult.
She had already developed intellectual property and operating methods that could be replicated. Instead of continuing to open locations individually, she organized those resources into a licensing system.
Within six months of launching the licensing business, the company reached 100 offices.
The decision came from understanding what she wanted to accomplish and being willing to change her approach.
Reign doesn’t describe her leadership style as something she consciously designed. She identifies an outcome, determines what needs to happen, and takes the necessary steps.
That independence has also influenced how she evaluates advice from others.
A Lunch Meeting That Changed the Direction of Her Business
Early in her career, Vivienne Reign was running a consulting practice that had become difficult to manage alone.
Clients kept coming, her schedule was full, and she was turning away opportunities because she couldn’t accommodate additional work.
She reached out to a business mentor who had already built and exited a company. He suggested meeting at Morton’s, where she could buy him lunch. He always ordered a hamburger.
During their conversation, he gave her advice that seems obvious in retrospect: hire someone.
More specifically, he encouraged her to delegate the simplest responsibilities so she could continue handling the work that required her experience.
Until then, Reign had never employed anyone. She had been operating as a successful independent consultant without fully considering what it would take to build an organization.
That conversation gave her the confidence to make her first hire.
The business eventually grew into a substantial multi-site operation.
Reign also discovered that hiring could create serious problems when the timing was wrong.
At one point, she added employees in anticipation of growth that hadn’t materialized. Payroll doubled, margins deteriorated, and owner distributions became nearly nonexistent for six months.
The experience changed how she approached staffing decisions. She learned to expand when existing demand justified the expense rather than assuming additional employees would automatically produce additional revenue.
What It Took to Build a Business That Didn’t Depend on Her
As her companies expanded, Reign began questioning how much of their success still depended on her personal involvement.
She wanted employees to have the information, authority, and training necessary to operate independently.
Achieving that required extensive documentation. Her teams established organizational structures, written procedures, reporting systems, checklists, and training resources.
Then she tested whether those systems worked.
She started by taking trips lasting one or two weeks without participating in daily operations. When she returned, she examined what had gone wrong and where employees had needed her involvement.
Each problem revealed something that required attention, whether it was an incomplete procedure, missing training, or unclear responsibility.
She made adjustments and tried again, gradually extending the time she spent away.
Eventually, Reign was able to leave the business for more than a year while daily operations continued successfully.
Still, the experience exposed an important weakness. Employees could manage existing responsibilities, but long-term planning and strategic development suffered without her involvement.
She worked with her executive team to establish quarterly and annual strategy meetings tied to clearly defined business goals.
The process helped her understand that delegating operations and delegating strategic responsibility require different kinds of preparation.
How Bad Advice Changed Her Approach to Mentorship
Some of Reign’s strongest opinions about mentorship developed through disappointing experiences.
At a conference, she watched a prominent speaker publicly criticize a woman who had come seeking guidance. The encounter left her questioning leadership methods that relied on humiliation rather than helping people develop their abilities.
She decided that her own approach would emphasize practical information, training, and constructive support.
Another experience carried a substantial financial cost.
Reign hired a business coach through a referral and ultimately spent a significant amount on his services. She later concluded that his sales abilities far exceeded the value of his advice.
While waiting for promised improvements, she watched her business performance decline.
The experience reinforced the importance of evaluating advisors carefully.
Today, Reign considers both character and measurable accomplishments before deciding whose guidance deserves her attention.
She wants to understand what someone has actually built, the role they played in achieving those results, and whether their approach to working with others reflects values she respects.
As she puts it, “Nobody will ever know your business better than you do.”
Resilience When Business Decisions Become Difficult
Reign frequently encourages entrepreneurs to develop the mental strength required to make decisions under pressure.
She has seen business owners delay necessary action because they’re afraid of making the wrong choice.
“Most of the time, people know what they need to do. They’re just afraid to do it,” she explained.
One particularly difficult experience tested that philosophy.
Reign discovered that a group of employees was planning a competing business while allegedly diverting leads and undermining sales within her company.
Resolving the situation required reducing her workforce by approximately one-third. The disruption resulted in a 30% decline in revenue.
She spent nights and weekends rebuilding the team and says the business recovered within 30 days.
The experience shaped how she discusses entrepreneurial resilience with other founders.
“If the first solution doesn’t work, you keep going, change the decision you made, and act again,” she said. “It isn’t about being perfect. It’s about solving it quickly and never giving up.”
Her emphasis is on confronting the actual problem, making a decision with the information available, and adjusting when the results indicate a different approach is necessary.
The Lessons She Continues to Learn From Her Teams
Although Reign has become a mentor to other entrepreneurs, she still seeks guidance herself.
Some of her most valuable insights have come from executives within her own companies.
She recalls a conversation with a company president who encouraged her to stop looking backward and concentrate on opportunities that had yet to be created.
The advice helped clarify how her responsibilities needed to change as the organization matured.
Her executive teams also challenge her when she becomes involved in decisions that belong to other leaders. Reign recognizes that bypassing established responsibilities can weaken the organizational structure she worked to create.
Watching those executives succeed has become one of the most rewarding parts of her career.
She now sees mentorship as an ongoing exchange of experience rather than a formal relationship between someone who has all the answers and someone who needs them.
Helping the Next Generation of Founders Make Better Decisions
Reign’s current work reflects many of the operational lessons she learned while scaling businesses.
She believes entrepreneurs need immediate access to reliable information about revenue, expenses, production, sales, and other performance indicators.
Earlier in her career, incomplete financial reporting contributed to decisions that placed one of her businesses in serious financial difficulty. Correcting the information helped her team identify problems, reduce expenses, and restore stability.
That experience has influenced the development of Frost, a business management platform designed to connect operations from initial customer contact through payment while keeping key performance indicators accessible.
The platform is initially focused on medicine, the industry Reign knows best.
She also continues to make time for entrepreneurs who approach her with thoughtful questions and a willingness to act on what they learn.
“There is no award for how difficult it was for you to succeed,” she said.
Her hope is that sharing what worked, what failed, and what she would do differently will help other founders avoid some of the costly lessons she encountered.
“The greatest thing you can do for an entrepreneur is help them believe in themselves.”
