From spite to service: The lessons that built my insurance career
Not everyone starts a career out of spite, but that’s how mine began. Fresh out of college and coming off a successful national sales competition, I sat down with my grandfather at the dinner table to talk about joining his cybersecurity business.
He immediately cut me off with, “Excuse me, what makes you think you’ll be getting paid to do this job?”
My grandpa wasn’t being cruel — he knew his business was struggling and wanted me to find my own path. But I didn’t know that then. His words left me feeling cast aside and dejected. Defiantly, I flipped him off and stormed out of the house – the partnership was over.
Still reeling from the argument and full of spite, I called a friend who worked as a captive insurance agent and accepted an internship at his agency. That will show him.
My grandpa’s’ stern push fueled me to prove myself. After starting as an intern, I was promoted to producer and wound up winning Rookie of the Year. Over the next 14 years, I underwent a transformative journey from captive agent to launching my own independent agency, McDade Insurance Brokerage, in 2020. And yes, I did show him!
I’ve learned a lot along the way. Some lessons came from wins; others came from incompatibility and preventable cancellations. Here are five lessons that changed how I sell, lead, and build an agency that lasts.
Lesson 1: Not all risk is good risk
Early in my career, I was hungry. I’d take any lead I could get because volume felt like the quickest way to prove myself. I’d take late-night calls, work on Saturdays and Sundays, and leave birthday parties just to be available.
One source of leads was used‑car dealerships. There were lots of initial buyers, but also lots of cancellations. People were stretching their budgets to buy a car and insurance on top of it. I was giving them what they wanted without taking the time to learn what they actually needed. In the end, people dropped out the minute money tightened up. Nobody won.
The takeaway: Don’t buy into the mentality that tells you: anything you can sell, you should sell.
The relational part of insurance — taking the time to learn a customer’s priorities and find the best policy for their needs — is where real value lives. When you skip that, it hurts the client, who ends up underinsured or chasing price, and it chips away at your book and your reputation. Instead, prioritize fit and long-term outcomes over short-term sales.
Lesson 2: Ask the questions that matter
One way to find the best fit is to go beyond surface-level insurance questions to get at what really matters to the customer.
For example, in home insurance conversations, I’ll ask, “What matters most to you in this policy — replacement cost on the roof, water damage, replacement for your personal property, or is it just price?”
About half say price, sure. But the other half name things that let me be of genuine service. That one question moves the conversation from a price negotiation to problem solving.
The takeaway: Start with needs, not price. If you start with price, you’re in a race to the bottom. If you start with needs, you can craft coverage that protects the family’s priorities.
That’s what builds loyalty. It’s also why agents will always have value: the ability to dig beneath the numbers and match solutions to real human concerns.
Lesson 3: Authenticity wins
When I first began my career, I felt like I had to tone myself down to make people feel comfortable. I kept my hair short and my face shaved. But the face I put on didn’t feel like me, and it held me back.
Over time, I learned that authenticity is my greatest asset. My clients didn’t care if I had long hair and a beard – they cared that I was consistent and reliable.
The takeaway: People don’t trust what feels rehearsed. People know who is real and who is not. We see it online all the time: slick videos, edited posts, messaging that doesn’t match the person who answers the phone. Trust erodes immediately when the real interaction doesn’t match the stage persona.
On the other hand, if you can show up as the same person people see advertised, then clients know what they’re getting. They come back. They refer. They stick around when things get complicated.
Lesson 4: Show up for the next generation
If authenticity is the strongest advantage in our work, its deeper payoff is in representation.
When I was voted onto the board of the Independent Agents of Houston and learned I was the first African American in its 102-year history, that news hit me in two ways: gratitude and pressure.
I don’t want to be the first, and more importantly, I don’t want to be the last. I want the opportunity to be a door that opens wider for others.
That’s why I do events like Insurance Day at local high schools or lead digital outreach for NAAIA Houston. It’s why I mentor, speak, and make space for younger professionals who don’t see themselves in our industry yet.
The takeaway: Being visible creates a sense of “You belong here” that’s hard to overstate. It’s also good business. Diverse teams bring different perspectives and make better decisions. But mostly, it’s the right thing to do: lifting others while building something that lasts.
Bonus lesson: Technology is a multiplier, not a replacement
There are a lot of people — especially younger agents — who are petrified about where AI will land.
But I can tell you through experience: Change never stops. That’s why I don’t freeze — I learn how to use AI tools so I can do the human work better.
At McDade Insurance, we use automation to speed quotes and follow-ups, AI to transcribe notes, and platforms to compare options quickly. These tools free our time to do higher-value work: coaching, client conversations, and complex problem-solving.
Treat technology as a multiplier of your empathy and expertise, not a substitute for it.
Carrying the lessons forward
I’m grateful for the trust our clients at McDade Insurance Brokerage Group have placed in us. That’s not something we take lightly.
I’m proud of what we’ve built, but to be blunt, I don’t measure progress by milestones. I measure it by the lessons earned in the field: the wins, the misses, and everything in between.
I cherish every opportunity where value springs forth from trust and effort. Those lessons shape how we protect families, how we show up when it matters, and how we help develop the next generation of agents.
While I may have gotten into the insurance industry out of spite, I’ve stayed because I care about protecting people. Me and my team at McDade Insurance take a lot of gratification from building relationships, educating clients on coverages and creating more opportunities for people who don’t always see themselves reflected in this industry. That’s the work worth doing, and the work we plan to keep showing up for.
