Articles by Tony Caldwell

Caldwell is an author, speaker and CEO of One Agents Alliance, an alliance of 185 independent insurance agents in Oklahoma, Arkansas, Kansas and California.

6 Steps to Breathe New Life Into the Agency’s Growth Strategy

Nothing works forever. Or at least it will not work as well as it may have in the past. This is especially true when it comes to a business’s strategy for growth. The economic environment fluctuates and these shifts require …

Reflections and Observations: 5 Takeaways from 2024 to Build a Better 2025 and Beyond

Last year seems like ancient history. Most people seem to have adjusted to the daily whirlwind of information, activity, and change peppering our businesses and lives. But, with all that activity, it has become difficult for many to find the …

Missteps and Mistakes: 5 of the Scariest Moments of My Insurance Career

I remember 1994 when I was running for the United States Senate. My campaign consultants thought I should publish my tax returns and challenge my opponent to do the same. He had a very checkered business career. I was unenthusiastic …

A Fresh Take on Commission: Envisioning a System That Supports the Agent, Carrier and Consumer

I confess that for a guy who has made his living largely on commissions for decades, I don’t like the concept. It’s not that I don’t like getting paid — I do — but I find the commission system in …

Upskilling: Three Skills to Sharpen as a Seasoned Agent Who Wants More

Whether they own their own agency or not, an insurance producer is essentially an independent businessperson. Why? Because a producer’s income, as someone whose primary income is based on commissions, is largely up to the producer. This may be obvious, …

Spring Cleaning: Getting Your Agency in Order for Sale

Rising interest rates have clipped the bloom from the rose in terms of sky-high sales multiples for many agency sales transactions. Despite continued strong demand for acquisitions, buyers are simply constrained by prime rates above 8%. Unfortunately, after two decades …

Exploring AI: Fascination with AI, Not Fear Will Drive Success for Independent Agents

I remember watching Michael Crighton’s “Westworld” in 1973. Two vivid impressions from that experience remain. The first was my date breaking my glasses when she screamed and threw her arms open during a startling scene. The second was the completely …

Revising the New Normal: Exploring the Future of Work for the Insurance Agent

Senator Bernie Sanders of Vermont, socialist and one-time presidential candidate, has been making headlines recently suggesting that government should mandate 32-hour work weeks for the same pay as the traditional 40-hour week. Naturally, this has been roundly criticized by many, …

Relationship Refresher: 5 Ways to Keep Your Professional Relationships Fresh

With technology relentlessly simplifying many parts of our business, and consolidations changing the competitive landscape as well, personal service businesses will continue to be challenged to rethink their business models in the coming years. Typically, when an industry sees change …

Tomorrow’s Insurance Agent: Leveraging New Skill Sets Next Gens Bring to the Table

For the last decade and a half, business leaders have struggled to comprehend, motivate and manage the millennial generation. Recently, I read an online article where business owners discussed the “new” generation of workers and it was both amusing and …