For Dale Thomas, entrepreneurship has always been about solving complex problems, staying adaptable, and learning from every new twist in the industry. With over two decades of experience in operations and ad tech, Dale started ActionableOps, a consulting company that initially focused on operational efficiency for businesses. But as the technological landscape shifted, so did his business. Today, ActionableOps is a thriving AI consultancy helping companies navigate the challenges and opportunities of artificial intelligence.
In a recent conversation, Dale shared his journey, the lessons he’s learned, and the challenges he’s facing as a modern entrepreneur in the fast-evolving AI space.
The Pivot to AI Consulting
Dale’s career has always revolved around operations, but it was the growing presence of artificial intelligence (AI) in his projects that prompted him to pivot his business. “I started ActionableOps as an operations consulting company,” Dale explained. “But everything we were doing seemed to incorporate AI. I realized it was a smarter move to focus fully on AI consulting.”
Dale’s new direction has not only been a learning experience but also a chance to push the boundaries of what’s possible with AI. “We’re constantly evaluating new technologies and pivoting slowly, adding new lines of AI agents to our service offerings,” he said. These AI agents help businesses automate complex processes, enhancing their operations.
But Dale is the first to admit that working at the cutting edge of AI is challenging. “It’s definitely like drinking from a fire hose,” he laughed. “There’s so much information coming at you. If you blink, things change. It’s why I don’t call myself an AI expert—I’m more of an AI explorer.”
Navigating the Wild West of AI
As an AI consultant, Dale is at the forefront of an industry that is still figuring itself out. He likens the current AI landscape to the Wild West, where everyone is staking their claim and trying to figure out the best path forward. “We’re all in this land grab right now, learning as we go. Everyone claims to be an AI expert on LinkedIn because they’ve used ChatGPT for six months. But this field is so new, and the depth of knowledge required is immense.”
This influx of so-called “AI experts” has presented unique challenges. “It’s all about positioning yourself well,” Dale said. “That’s one of the reasons we wrote a book and started doing podcasts. We want to position ourselves as knowledgeable, but also be transparent about the learning process.”
Staying Focused Amid Distraction
As an entrepreneur working in a rapidly evolving field, staying focused is a constant struggle. Dale acknowledges that it’s easy to get distracted by every new shiny object in the AI space. “It’s really hard to stay on track, especially when you’re in a field where everything is changing so fast. My advice to other entrepreneurs is to find one or two areas to focus on and go deep into those. Don’t try to become a jack-of-all-trades.”
That focus is what has helped Dale guide his company through its AI transition. Instead of getting bogged down by every new development, he concentrates on what his clients need most. “Operational efficiency doesn’t change that much, which is why we’re really good at it. AI is just the next layer we’re adding to help businesses optimize even further.”
Learning from Experience: Three Key Lessons for Entrepreneurs
As someone who mentors aspiring entrepreneurs at the University of Missouri-Kansas City, Dale often shares the lessons he’s learned from his own journey. When asked about the key things entrepreneurs need to succeed, he pointed to three crucial elements:
- Build a strong operational foundation: “It’s easy to get caught up in generating revenue, but you also need to make sure the basics are in place—your accounting, insurance, and all the other operational aspects of your business,” Dale advised. “I’ve seen so many entrepreneurs overlook these fundamentals, only to realize later that they’re missing key pieces of their foundation.”
- Develop executive presence: “It’s not just about the business opportunity; it’s about how you present yourself and your vision,” Dale said. This is something he’s personally worked on over the years, especially as someone who is neurodiverse. “I’ve had to learn how others perceive me and work on softening my approach in certain situations,” he explained.
- Lead with empathy and trust: One of Dale’s most important leadership principles is trusting his team. “You can either operate from a place of suspicion or trust,” he said. “I choose to trust that my team is doing the right thing, and I see my role as removing roadblocks for them so they can succeed.”
The Importance of Personal Relationships
While Dale enjoys the flexibility of remote work, he’s a strong advocate for in-person connections. “I think being remote is overrated,” he said candidly. “You miss out on the watercooler conversations that can turn into massive opportunities.”
Dale shared a recent experience to highlight this point: “I was at a mentoring event, just having a casual conversation with another business owner, and it turned into a potential opportunity to develop AI agents for large-scale retail stores. That wouldn’t have happened if I wasn’t out in the community.”
Scaling Up: The Challenges Ahead
Like any entrepreneur, Dale has big goals for the future. Over the next six to 12 months, his focus is on scaling ActionableOps and hiring the right talent to build AI agents for clients. But with those goals come challenges. “I need to remind myself that I can’t eat the whole elephant at once,” he joked. “Hiring the right people is key. I still want to understand the technology, but I’ve realized that to scale, I need to bring in experts to help build these agents.”
Dale’s approach to overcoming these challenges is strategic. “For us, it’s about positioning ourselves well across multiple channels—social media, community networking, and workshops. But we’re also focused on being part of a local community. I’d rather build relationships in my own backyard than make millions from clients in Europe and still feel isolated.”
A Leadership Style Rooted in Empathy
As Dale looks to the future, one of the most profound lessons he’s learned is the value of leading with empathy. “As a leader, your job is to enable your team and help them succeed, whether they’re staying with your company or moving on to the next role,” he said. “Gary Vaynerchuk talks about this a lot—leading with kindness and compassion—and that resonates with me.”
Looking back on his previous ventures, including a children’s franchise business, Dale is proudest of the culture he built. “We kept 60% of our staff, even though they were high school and college students where there is typically a high turnover rate. That’s a testament to the environment we created.”
Final Thoughts
Dale Thomas’ entrepreneurial journey is a story of constant adaptation, learning, and leading with empathy. Whether he’s navigating the fast-paced world of AI or mentoring the next generation of entrepreneurs, Dale’s focus on operational excellence and human connection sets him apart.
For anyone looking to follow in his footsteps, his advice is simple: “Stay focused, trust your team, and never stop learning.”
As ActionableOps continues to grow, Dale’s approach to leadership and his dedication to his community will undoubtedly leave a lasting impact on the businesses and people he works with.
Connect with Dale Thomas on LinkedIn
Connect with ActionableOps on LinkedIn
