Tony Caldwell of One Agents Alliance: “Start small and test”

Start small and test. Starting big and then failing costs a lot more and wastes a lot more time. I started a new business a few years ago with new partners and we invested a considerable amount of money in an idea that could never work. If we had started small, we would have learned […]

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Start small and test. Starting big and then failing costs a lot more and wastes a lot more time. I started a new business a few years ago with new partners and we invested a considerable amount of money in an idea that could never work. If we had started small, we would have learned the same lesson for much less money and time.

Many successful people reinvented themselves in a later period in their lives. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Kroc was a milkshake-device salesman before starting the McDonalds franchise in his 50’s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Tony Caldwell.

Tony Caldwell, co-founder and chairman of CEO of One Agents Alliance, one of the country’s largest regional insurance distributors, has reinvented himself numerous times. An entrepreneur, pilot, author and former state legislator and US Senate candidate, Tony has mastered “the second act” and has advice for others, who may be looking for what’s next. Over the last 20 years, Tony has partnered with over 250 entrepreneurs to create local independent insurance agencies which today produce in excess of 500 million dollars in premium annually.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I was born and raised in Norman and Oklahoma City, Oklahoma, with the exception of my first-grade year. That year, my mother moved my siblings and me to France just as I was set to begin elementary school. Attending first grade in the French public schools was challenging. I did not speak French and none of my classmates or teachers spoke English. At that time, first graders in France were expected to be able to read, write in cursive and master math that most American students were not introduced to until later. So, I was behind and the language and cultural barriers, for which I was not prepared, did not help. In those days, students who performed poorly were forced to wear a sign that said “idiot” around their necks. These poor children were paraded through every classroom to set an example. Consequently, I was highly motivated to catch up with my classmates and perform well in school. I realize now, this was my first real experience in setting a goal and recognizing the importance of hard work.

Returning to the U.S. was a difficult adjustment as well. I could not have done it without the considerable help I received from teachers and my fellow students. Appreciative of the help I received, I learned early the value of helping others.

I had an entrepreneurial spirit from an early age. My father helped me start my first business subcontracting labor at the age of 10 to do yard work. When I was 14, I bought a key machine on credit from my father and went into the business of cutting keys commercially for newly constructed apartment complexes. I cold called contractors armed with letters of referral from previous customers. By undercutting other’s prices and offering a 100 percent guarantee on my work product, I had all the business I could handle. I moved on, taking jobs as a restaurant cook and later a server. Working in the restaurant industry, I continued to develop and hone sales skills.

The elections of 1968 sparked a new interest for me in politics. I began volunteering in campaigns and continued to do this into my early 30’s when I became a candidate myself. Running for the US Senate in 1994, I fulfilled a lifelong dream for which I’d worked for nearly a quarter century.

Between campaigning and working in sales, I learned how effective cold calling could be. Later, as a candidate for the Oklahoma House of Representatives, I made 14,000 cold calls to voters and knocked on nearly 15,000 doors — a tactic that won me elections. When I began my insurance career, building a book of business through cold calling seemed natural and easy.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My paternal grandmother was fond of the story of “The Little Engine That Could.” When I became frustrated and wanted to quit something, she would recite the story about the little choo choo train that struggles to the top of the mountain by constantly telling itself “I think I can, I think I can”.

That quote, and others like it, has reminded me over and over again that my future is up to me. Faced with frustration or failure, I’m reminded that usually the one who ultimately decides if I can or cannot is me. Perseverance in the face of obstacles has been paramount to whatever success I’ve enjoyed.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

Grit. Success is always a combination of preparation, luck, timing, talent and hard work. But, what binds those things together to create success are courage, determination and will. All of us are faced with seemingly insurmountable challenges. What ultimately leads to the successful conquering of those challenges is grit.

When I was 34, I had the opportunity to run for the U.S. Senate, which I’d set as a goal 24 years earlier. Unfortunately, not long after I entered the race, it became clear I couldn’t win. I was encouraged to keep my seat in the Oklahoma House and run again another time but a friend had started his own campaign to replace me. Because he launched his campaign at my urging, I didn’t want to take that away from him. For the next five months, I worked harder on the campaign trail than I had ever worked in my life. I knew my only chance was a miracle, but that a miracle couldn’t happen without my best effort. I also knew that if I lost, which was more than likely, I’d have to look myself in the mirror the rest of my life. I wanted to be proud of the effort I’d put forth regardless of the outcome. In the end, I lost the race but I won a lifetime of self-respect.

A desire to help others. I’ve always believed my purpose in life is to help others and I have long worked toward discovering the best way to do so. As a political volunteer, candidate, office holder, seminarian, Boy Scout leader, board member and business leader, I have cherished every opportunity to serve others. Our business’s goal is to be a “Dream Factory” where we work to help those associated with us achieve their personal and professional dreams. I’ve strived to build a business that serves as a means to help others.

To me, integrity means doing what you say you will do. That, in turn, is related to commitment. Coming from a home broken many times, I have always been determined to build a strong and close family with my wife. It is a preeminent purpose in my life. I had an experience on a family vacation many years ago where I stopped in an internet café to check email. Later, I realized I had no idea where we were. While my body had been on vacation, my mind was at the office. At that moment, I decided I had to completely separate my work and family life in terms of time. I eliminated email, cell phones and other things related to work when I was with my family. That commitment has led to strong personal relationships with my family, treasured memories of time together and, not surprisingly, continued business growth as I focused more clearly on work at the appropriate times.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

After leaving the seminary, I went to work in the computer business for several years. It was a terrific learning experience gaining the know-how to market and sell products, manage a business and manage people. But after trying to buy my employer, I was fired by my boss who didn’t want to give up his job. It was one of the best things that ever happened to me as it freed me up for an entrepreneurial career.

I went into the property management business with my father. He had a small company at first, which in just a few years of working together, we built into one with about 130 employees and 3,500 apartment units. There, I had the opportunity to work on my sales skills, as well as financial and other business skills. Ultimately, I sold my interest in that business to run for the Senate.

Having lost the Senate race and without a job, I asked people I respected for advice. “What would you do if you were me?” One of those people suggested I join him in the ownership of his independent insurance agency. Accepting that opportunity, my goal became to build a large, and respected sales organization. I had no idea how to do that and I had no capital to embark on such an endeavor. But we began building the agency and making headway. One day, I learned about an organization called Strategic Insurance Agents Alliance (SIAA) that helped agencies solve intractable problems like carrier representation and high-quality compensation through a partnership model. Though my partner wasn’t really interested in this business, he agreed to try it and we launched Oklahoma Agents Alliance in late 2000.

Though OAA was successful, it became increasingly clear to me that my partner and I didn’t share the same vision. I believed we could be much more than we were. It took me quite a while to summon the courage to break away by buying his interest in the company, but I ultimately did so in 2012.

And how did you “reinvent yourself” in your Second Chapter?

I never felt I was the same person at work that I was in the rest of my life. Primarily for this reason, I wanted my business independence. Outside of work, I was involved in leadership in one way or another. Often, those roles allowed me to make positive contributions in the lives of others. I wanted to unify my life and it just didn’t seem possible in my business and with my colleagues at the time.

After buying the company, I had a conversation with a valued employee alongside a prospective employee. Listening to my colleague detail our business, I realized I hated the description. As I thought about it, I realized I didn’t like the culture we’d created and that the only person who could change it was me.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

As I thought about the type of organization I wanted to represent, I spent considerable time thinking about my personal values. I realized my company didn’t embody them. So, I made a presentation to our team about who I wanted us to be. Met with eye rolling, heavy sighs and strong resistance, I was discouraged. I asked my business coach, Dan Sullivan of The Strategic Coach Program, what to do with people who fought me on values and culture. His response was transformative for me: “those people aren’t on my team.”

I had many good people on our team. Some had been with the company for years. That said, I came to see agreement on values as the foundation of a strong culture, and a strong culture as the key to long-term success. So, I addressed my team, saying “this is who we seek to be. If it excites you, you are in the right place. But, if it doesn’t, please go away. Don’t go away mad. Just go away. And let me help you find a culture you are excited about.”

The result of this was that we had 100 percent turnover during the next three years. During the same period, we also grew 326 percent. More importantly, I began to feel at home in my own business and no longer conflicted by who I was at work compared to who I was outside the office. And even better, we attracted a stronger, more cohesive team of people who regularly vote us as one of the best places to work in our state and industry.

Our new culture has led to a great deal of success for our team, company and all the agency partners with whom we work. I’m constantly excited to hear about new millionaires in our organization, but especially about kids going to college, team members starting their own businesses or those pursuing deeply meaningful personal goals. We’ve become a dream factory. And, increasingly, I’m able to spend my work time doing those things for which I have passion and purpose because of the strength of our team.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

When I first became a client of Strategic Coach in 2008, we spent a lot of time on an exercise they call “Unique Ability.” It’s a discovery process where you drill down to the one, two or three things you do best. With that knowledge, you can increasingly fine tune your work to focus on those things. This exercise confirmed things for me but more importantly helped me to commit to getting rid of those things that weren’t in my best skill set by giving them to people who were better at it than me.

I look at my work activities every 90 days and ask what I should no longer be doing. After more than a decade, thankfully, there are fewer things to remove from this list. However, a couple of years ago during a coaching session with a marvelously talented and insightful woman named Julia Waller, I realized 80 percent of my time was still devoted to things I could forego in favor of those few things I do really well. She helped me build a plan to focus on my best work. Today, three years later, I am able to spend 90–95 percent of my time doing those things at which I excel and love the most.

What’s been interesting and motivating is that the more I give up, the more progress my team and I achieve together. I’m as busy as I have ever been but I’m doing much more rewarding work more frequently and am increasingly excited about working as long as I possibly can.

How are things going with this new initiative? We would love to hear some specific examples or stories.

I planned to write a book for years but couldn’t find the time. Last year I not only wrote one book, I wrote six “mini books” and coauthored another one. I also started a podcast and began writing regular articles for several publications in my industry. These projects have been fun for me to do. They’ve also been really helpful to our business. This new freedom of time has allowed me to become more involved as a leader in other business organizations and industries. But what I find most rewarding is the opportunity to provide coaching to other entrepreneurs as they work to build their own dreams.

I became chairman of the board of a local community bank a year ago. As I started in that role we brought our team together to discuss values and culture. The conversation has led to some turnover but also a more cohesive team. It has also led to dramatically improved performance.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

The person who I am most grateful for is my wife Sharon. I couldn’t have started in my current business or industry without her help. More importantly, I couldn’t have made it this far without her support and advice.

I’m grateful to my former business partner Ken Anderson who gave me the opportunity to become a partner in an insurance agency and who mentored me on technical matters for years.

I’m especially grateful for my team at One Agents Alliance. They individually and collectively give me the opportunity to be able to focus on my talents because they are themselves so talented. The values they cherish and we share have served as our guide to collective success.

Can you share the most interesting story that happened to you since you started in this new direction?

Focusing my work on only those things I do really well and foregoing other tasks to folks more talented in that space than I is much easier to say than do. I had a tendency to let myself go in the wrong direction and reassume a task when I saw the other person approaching it differently than I would have. Since then, I’ve learned that instead of taking over the tasks of others, I can serve the employee and the company better by coaching them to improve. Coaches make such a difference in performance, in sports, life and business, not only because they hold us to a higher standard of performance but also because they have a perspective that is unique and different from our own. That perspective allows them to see opportunity as well as talent or room for improvement that we often miss in ourselves.

Because my company is a business development organization, I decided to hire a highly qualified adult education expert to improve our efforts in this regard. As I look at all that she has accomplished in the last few years, I recognize that most of her accomplishments resulted from teamwork with my COO and Agency Development Director, not just from my ideas. Seeing others do new and unexpected things, along with improving traditional processes has become increasingly exciting and I’ve learned that truly letting go of activities and focusing strictly on results is increasingly motivating, satisfying and inspirational.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

Frequently. I think the most important quality to overcome self-doubt is courage. And I think courage is like a muscle that grows with use.

In 1990, I participated in a community leader training program. At the end of the year, we were asked what we were going to do in the next two years to contribute to the future progress of our community. I said I’d run for the legislature. A year later, there was an unexpected opening and it seemed like now or never. I was terrified. I’d have to raise money. I’d have to do a lot of other things I had no idea how to do. Most of all, I was afraid of a public, humiliating failure. I made a list of all the things I’d need to do and all the things I didn’t have that I’d need to find. Then, I gave myself no exit. I filed to have my name on the ballot.

I won that race, but I lost a bigger one later in my political career. What I learned was failure isn’t fatal. As I now like to say, “failure that you learn from is just tuition for something else”. I’ve learned that putting ideas into motion is often the hardest thing to do, but its critical. If you don’t get in motion, you are guaranteed to fail.

I’m still constantly plagued by self-doubt about my abilities or the likelihood of being able to succeed in certain endeavors. But I’ve learned if I just have courage, I can turn ideas into action and then I’ll be on the way. It makes life and work an adventure.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

Before I ran for the legislature, I attended a “ropes” course. One challenge was to walk across a beam suspended by two cables. I couldn’t do it. The woman running the challenge said “why aren’t you using the help freely offered by the two people standing next to you? When you begin to lose your balance all you have to do is reach out to them for help. You can’t be successful in this challenge or in life without being willing to accept the help of others.”

That hit me like a sledgehammer and I’ve tried to remember it since. When I decided to buy my partner out it was a huge financial commitment and risk. I asked my banker for back up help, sharing my fears and concerns with him and benefitting from his encouragement. I asked my wife for her help and support and she gave it. I reached out to friends for moral support and received their reassurance. I asked my employees to help me. I turned to my former partner for advice on many occasions. I like the word “encourage” because it means to put courage in another. I have greatly benefited from the encouragement of others.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

During my business career, I’d always had a partner(s). I liked having a partner because their talents, combined with mine, helped keep me from trouble. It always felt safer. And when you’re in business with a partner, you have them to share in your successes and disappointments.

Being the leader of a business on my own felt like walking a tightrope without a net. Despite the success of the business, it was scary. I worried I might be exposed as some sort of fraud. For some reason, that I’d not experienced before with partners, I felt alone and emotionally naked. I was way outside my comfort zone. But what’s interesting now is how comfortable I feel in this same role. In fact, I can’t imagine ever going back to the place where I have to seek permission or consensus. I’ve learned to want, like a star athlete, to have the ball in my hands. I’ve grown comfortable with fear.

What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

While I dislike dwelling on the negative, there are people for whom jealousy and envy are their prime motivators. They will hurt you if they can. These people must be discovered and rooted out of your organization and life as quickly as possible. I’ve had former employees who didn’t like changes I believed were necessary. I learned everyone has to row the same direction on your team. If someone is rowing against the current, let them go.

Start small and test. Starting big and then failing costs a lot more and wastes a lot more time. I started a new business a few years ago with new partners and we invested a considerable amount of money in an idea that could never work. If we had started small, we would have learned the same lesson for much less money and time.

Culture is everything. If you aren’t intentional about the culture it will change with every new hire. You and your team will never accomplish what you could with a successful company culture. I’m convinced that getting this right has been the main key to our success as a great workplace but also as a company with a CAGR of more than 30 percent for more than 20 years.

Work on yourself first. As a former athlete, I understood the value of coaching to improve performance. But as a businessperson and entrepreneur, I didn’t discover how important it is in this context for many years. I now know the person who most needs to grow in capability in my organization is me.

Everyone’s watching you. As the leader, you set the example and being human is important. But, when you have a bad day, react poorly, lose your temper, get frustrated, act frightened or otherwise behave badly, everyone sees it. By the same token, everyone notices your work habits whether they are good or bad. Early in my stewardship of my company when I was frustrated with our culture, I made it harder to correct by failing to control how my frustration was manifested. I learned through experience what I wish I had learned from others which is that you need to always remember to be intentional about everything you say and do.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

To help people learn to put others first. A great deal of the problems in our society are the result of selfishness in one form or another. If we could learn to ask a simple question of ourselves and others every day “how can I help?” I believe the results would be simply unbelievable.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. 🙂

Adam Grant

How can our readers further follow your work online?

My podcast is here:


My blog can be found here:

Mini books here:

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Thank you so much for sharing these important insights. We wish you continued success and good health!

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