You’re So Fly: Tony Caldwell

We’re thrilled to feature Tony Caldwell, founder of The 2326 Group, as this month’s You’re So Fly member! Owner of The 2326 Group, Tony brings a strong background and genuine authenticity to his growing leadership and professional coaching service. His approachable style, thoughtful insights, and commitment to community make him a standout presence at Flywheel. Keep reading to learn more about Tony’s journey, his mission, and the impact he’s making both in business and here at the Cabarrus Center.

1. Tell us who you are, what you do (and a brief history of your past work experience that got you into your role now).

My name is Tony Caldwell, and I coach people to help increase their impact. I spent over 25 years in the Army, starting at the bottom of the rank structure as a Private First Class and moving up to Lieutenant Colonel when I retired. (In civilian terms, I started in the mailroom and became a Senior Vice President.) That gives me a unique perspective on how leaders can lead up, down, and across a complex organization. All of my assignments gave me the chance to coach others. My best memories of my time in uniform were when I was able to help somebody else be better. I tried a few different jobs after I retired, but none of them gave me the level of fulfillment I was looking for. Over time, I realized that the ability to help other people get better is what was missing. That’s why I decided to leave the corporate world and open my own coaching practice.

2. Your company, The 2326 Group, specializes in leadership and professional coaching. What do you think is the biggest challenge facing your customers, and why they most need a coach?

The biggest challenge I’m seeing these days is the different forms of fatigue. A lot of people call it burnout, but it can manifest differently for each person. It can show up as a disconnection from the purpose of work, return to office issues, the pressure of being successful, having to always “be on” for the company, or people you lead. Coaches can help clients identify the core issues creating those feelings. Then the coach and client can partner to develop actionable plans to overcome them.

3. What would you say is the most rewarding aspect of your work?

I love it when my clients have an “AHA!” moment during a session. It’s in that moment that the client not just understands what they need to do, but realizes they are in control and are able to move forward.

4. Being a veteran entrepreneur is a big part of your life – what advice would you give for veterans entering the entrepreneurial world?

Veterans have a lot of great power skills and soft skills they take for granted. Learn how to translate those into terms non-Veterans can understand. Not only for your resume, but for regular conversations too. Veterans have the adaptability, grit, and drive every entrepreneur needs. Find a mentor or coach to bounce ideas off of and to get feedback on what you’re doing. Network, network, network, and then network some more. Tell everyone who you are and what you’re doing. Your first customers are going to come from your network.

5. A big part of what you help people do is “reframing” their problem. What are some simple ways we can reframe our situations in every day life?

Think about what you’re thinking about, and think about how you can see things differently. Don’t think about things in the context of “yes/no”, ask yourself “what if?” and look for different options.

6. How would you say coworking has impacted your growing business?

As an entrepreneur who’s bootstrapping a new company Flywheel has had a huge Return On Investment for me. It’s expanded my network faster than the other things I’ve been doing in that space. I’ve met people who were willing to share their expertise with me over a cup of coffee. It’s also given me access to seminars that helped me refine my business practices.

7. What is the best way for folks to get in touch with you if they want to learn more about coaching with The 2326 Group?

You can email me at info@the2326group.com or use this link to set up a discovery call.

8. Anything else you want to leave us with?

Professional coaches don’t tell clients what to do or provide the answers for them. Coaches and clients create a partnership that inspires clients to maximize their personal and professional potential. Coaches are curious about their clients, asking open-ended questions to evoke awareness in the client about their issues.