Skip to main content

M.R. Asks 3 Questions: James Harold Webb, Chairman and CEO of Paradigm Development Holdings

By March 14, 2024Article

James Webb says the difference between success and failure often comes down to whether the person thinks big in the early stage of the business.

Author of Redneck Resilience: A Country Boy’s Journey To Prosperity, James is an investor, philanthropist and successful multi-business owner. He began his entrepreneurial journey in the health industry as the owner of several companies focused on outpatient medical imaging, pain management and laboratory services.

Following successful exits from those companies, James shifted his focus to the franchise world and developed, owned and oversaw the management of 33 Orangetheory Fitness® gyms, which he sold in 2019. Not one to stop, he currently has two additional franchise companies in various stages of growth.

His insights as a life-long entrepreneur offers great insights for those looking to branch out with building businesses they own, and connecting it with their big-picture plan.

M.R. Rangaswami: What are the top two most common missteps a young entrepreneur makes in their first two years of business?

James Harold Webb: There are many mistakes an entrepreneur can make during the start-up stage of their business. Taking money “off the table” too quickly can lead to an assortment of problems, including holding back building your infrastructure, expansion, and cash shortage. Other than my “salary” (if needed), I tend to leave all the money back in the business for several years. The only exception to that is determining any income tax consequences and taking what I call a “tax distribution.” Solely for the purpose of paying the prior year’s income taxes or quarterly income tax payments.

I see too many 8to5ers who are not putting in the time or effort it takes to get a business off the ground and profitable. When you are ready to stop for the day, make one more phone call or send out one more email. Solve one more problem. Unbox one more package. Whatever it takes, just work harder than anyone else.

M.R.: How important is a leadership team in the early stages of building a business? What (if any!) budget should people allocate to that leadership team? 

James: Leadership is one of the key elements of a successful business. Creating a corporate culture from the beginning is crucial. Establishing relationships is also extremely high on the leadership list, whether it be with fellow corporate staff, employees, vendors, banking, or even competitors. Listen to people. Invest in people. Take the time to recognize people and to hold yourself accountable to them. Relationships will define your success.

M.R.: How can someone who is just starting their business beat the odds and not fail in the first five years? 

James: Work harder than anyone else.

Hope for the upside, but always plan for the downside. Stay focused on your upside and driving your business to success, but have a contingency plan for the “what ifs.”

Build a solid infrastructure before you reap the benefits of your venture. Find the right people who are dedicated to helping you reach your dream of success.

With employees, be clear in your expectations, hold them accountable, and be available to assist and direct as needed. Contrary to popular belief, you can be a boss and a “friend.” If they can’t get it done and you’ve done the previous, then it’s time to let them go.

M.R. Rangaswami is the Co-Founder of