#367 How Mid-Sized Companies Can Beat the Giants with AI artwork

#367 How Mid-Sized Companies Can Beat the Giants with AI

Embracing Digital Transformation

July 14, 2026

Check out my new book AI Augmented Teams on Amazon or on my website paidar.ai/books. AI can feel like a race, but the smartest leaders are asking a much simpler question: where is the real business friction? Host Dr.
Speakers: Dr. Darren Pulsipher, Matt Strippelhoff
**Dr. Darren Pulsipher** (0:00)
Welcome to Embracing Digital Transformation. Before we dive in, I wanted to personally thank you for listening. Many of the ideas we discuss on this show inspired my new book, AI Augmented Teams. If you're looking for practical ways to combine human expertise and AI to achieve better outcomes, I think you'll find it valuable. Learn more at paidar.ai/books. That is paidar.ai/books.
Now, let's get started with the show.

**Matt Strippelhoff** (0:30)
The big companies, they just are. You look at the big four consultancies, how are they going to continue to compete at the same level when smaller consultancies are, to your point, much more agile, very quick to innovate and adopt and transform in their business.

**Dr. Darren Pulsipher** (0:51)
Why this matters to you. AI is moving from experimentation to operating model, and that changes the questions leaders have to ask. The real risk is not missing a tool, it is automating the wrong process, at the wrong cost, with the wrong data. Mid-sized companies have a real opening here because they can move faster than large enterprises, but only if they start with business friction and not vendor hype. In the next few minutes, you will hear a practical way to think about where AI can actually create value.
Welcome to Embracing Digital Transformation. This is Dr. Darren.
On this episode, why AI projects fail when leaders skip data and workflow readiness with Matt Strippelhoff, founder and CEO of Red Hawk Technologies. Matt, welcome to the show.

**Matt Strippelhoff** (1:44)
Thanks, Darren. Glad to be here.

**Dr. Darren Pulsipher** (1:47)
I'm really interested in talking about the topic today, which is AI. Oh my goodness. Is it about AI? Everything's about AI today.
But specifically, how to get started, especially those mid tiers. I think that would be an interesting topic. But before we do, everyone that listens to my show knows that I only have superheroes on the show, and every superhero has a background story. So Matt, what's your background story?

**Matt Strippelhoff** (2:13)
My background story? Wow. Entrepreneurism is, you know, it's always been fascinating to me. My grandfather traveled here from Germany with when he was 15, his best friend was 16, they could not speak any English, and they landed on Ellis Island on Black Tuesday.

**Dr. Darren Pulsipher** (2:33)
Oh my God.

**Matt Strippelhoff** (2:33)
And my grandfather went on to be a very successful business owner in the tool and die industry, which is the trade that he came over as a journeyman. And watching his journey as a growing up and seeing what he was able to accomplish was inspirational for me. And I think that there's a lot of entrepreneurs in our family in general. And so, I don't know, it was really kind of cool to just watch all of that. And he's passed many, many years ago. And I like to think that he's probably very proud of what we've been able to accomplish as a family and kind of carrying on the tradition and all of that good stuff.

**Dr. Darren Pulsipher** (3:09)
So yeah, that's really interesting because I've talked to several entrepreneurs, and it is generational. It's almost like it's in your DNA or you see your grandparents and parents go through it and you're like, I want to be part of that. But it's not all, it's all not all fun.

**Matt Strippelhoff** (3:31)
It's not. I mean, it is the hills and valleys are very real. I'm sure everybody listening is probably seen the iceberg, the tip of the iceberg above the water and then all of that stuff below, or maybe the journey where there's a stick figure walking across and you can kind of see the hilltop, but you don't see any of the traps along the way. And it's every bit the grind that you read about if you're going to read about entrepreneurism for sure, but it's a journey. I don't think I could have chosen any other way.

**Dr. Darren Pulsipher** (3:59)
Any other way.
Isn't that crazy though? Yeah. So I think this is really cool because you actually help mid-sized companies. That's what you guys primarily do, which are probably run by entrepreneurs.

**Matt Strippelhoff** (4:15)
Oh, absolutely. They're all privately owned. There's probably some, certainly many are multi-generational family-owned businesses that we're working with. And a lot are entrepreneurs who started and just have the grit to really grow and start to scale and have these different breakthroughs along the way.
And they're transforming digitally as a result of that, trying to get to that next level.

**Dr. Darren Pulsipher** (4:38)
Yeah.
That's awesome. So let's talk about that. That's a unique, it's actually one of the largest economic engines in the United States is midsize and small business. We always think of the big boys, Tesla, Intel, Google, Meta, right? But they don't employ nearly as many people as mid-tier and small businesses.

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