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Pat CostelloPat Costello is the Co-founder and Principal of Evolve MGA, a company specializing in cyber insurance that does the underwriting for one of the most comprehensive cyber insurance policies a business can buy. Pat co-founded Evolve MGA with his brother Mike because they knew they could provide retail insurance brokers with far more value than anyone else in the marketplace. He is a veteran of the insurance industry and is the fourth generation of his family to be a leader in the insurance field. Pat is also hosts The Evolved Broker Podcast.

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Here’s a glimpse of what you’ll learn:

  • Pat Costello shares his entrepreneurial journey and how it led to co-founding Evolve MGA
  • How real-world feedback is key to the path to success
  • The growing importance of having cyber insurance to protect your business and keep it from being compromised
  • What cyber insurance is, what it covers, and the increased potential of being hacked as more enterprises become internet-connected
  • Why small to midsize businesses are targeted more often than larger businesses
  • Pat reflects on the early days of getting Evolve MGA off the ground and the dedication it took to secure business

In this episode…

How do you respond to real-world feedback regarding your entrepreneurial ideas? Sometimes you can see what’s needed, but you must have the tools, background, and determination to get your ideas off the ground. What can you bring to the table besides pure hard work to grow your ideas into a viable business?

As the world becomes ever more connected to the internet, the risk of being hacked increases. Pat Costello co-founded Evolve MGA with his brother Mike in 2015 to help protect people and businesses from cyber threats. Pat stresses the importance of cyber insurance to all businesses, especially small and midsize businesses since they are involved in 43% of all data breaches.

In this episode of the Rising Entrepreneurs Podcast, John Corcoran welcomes Pat Costello to the show. As Co-founder and Principal of Evolve MGA, Pat shares the story of his early entrepreneurial journey and how it taught him the value of real-world feedback. He also shares the story of founding Evolve MGA and the dedication and thriftiness required to build it to where it is today. Pat discusses the value and protection cyber insurance can add to your business and the growing importance of having cyber coverage.

Resources mentioned in this episode

Sponsor for this episode…

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Episode Transcript

Intro 0:02

Welcome to the Rising Entrepreneurs podcast where we feature top founders and entrepreneurs and their journey. Now, let’s get started with the show.

John Corcoran  0:11  

Hi welcome everyone, John Corcoran here. I am the co host of this show. Check out our archives if you’re new to this show, we’ve got lots of great interviews with entrepreneurs, CEOs and founders, talking about some of the challenges that they’re through. And I’m also the co founder of Rise25, where we help connect b2b business owners to the ideal prospects and I have been a EO San Francisco member for a few years now. And this episode is brought to you by EO San Francisco now, EO are the Entrepreneurs Organization is a global peer to peer network of more than 16,000 now influential business owners with 198 chapters in 61 countries and if you’re a founder, co founder owner or controlling shareholder of a company generating seven figures or more in revenues, then we want to tell you about EO. So EO is a member led organization and enables leading entrepreneurs in the Bay Area to learn, grow and achieve greater success. The EOSF chapter was founded in 1991. Today, we have about 100 members in industries ranging from marketing, agriculture, tech and professional services. And to learn more about how it works, or to come to a test drive. Come join us at

And alright, my guests here today is Pat Costello. He’s a veteran of the insurance industry. And what’s really interesting is he started a cyber insurance specialist firm, which does the underwriting for one of the most comprehensive cyber insurance policies that a business can buy. And so if your business is doing anything online, and you had any curiosity around what your liability could be with online with cyber attacks, things like that, which is just becoming so much more common, then you will want to listen to this interview. We’re gonna talk about that. And he actually co founded this firm with his brother, Mike, in 2015. So we’ll talk about that. And he’s actually a fourth generation in insurance, which I didn’t even know that going back that many generations, we even had insurance. I mean, that’s like wheel and buggy days. So that’s impressive that, you know, your great grandfather was doing this. He’s also the host of the Evolvement Broker podcast, which he’s been doing since about 2020.

Alright, Pat, such a pleasure to have you here. And I want to journey into your background in entrepreneurship. And you had this experience of going to, I believe it was a baseball game, and you went to go get food from the food stand in a foul ball landed at your seat, and you missed it. And this is about 2010. And you said, you know, wouldn’t it be great if there was an app that could you could just order food from your seat. Now, I think that kind of thing exists, but they didn’t at the time. But here’s the crazy thing. You were actually taking entrepreneurship classes at the time you brought it up with a professor and they said, “That’s a horrible idea and never work.”

Pat Costello  2:55  

Yeah, that’s true, John, I got absolutely trashed. And to this day, I don’t think someone has really cracked that code, the way that it should be cracked. I’m a big San Francisco Giants fan. That’s where that foul ball incident happens. And you know, I’ve been to a lot of giants games this season already. Been to some Golden State Warriors playoff games, big shout out to the Warriors for just winning the championship. But you know, it’s a lose lose when you get up from your seat. Right? You have to wait in line. Nobody likes waiting in line. And, you know, it’s not like the stadium is not equipped to bring food and drinks to your seats. Generally, a lot of times it only happens in the lower level.

John Corcoran  3:36  

A certain luxury level or a certain level. Yeah, yeah.

Pat Costello  3:40  

I don’t know why that’s not the norm across the whole stadium. But like you said, there have been a few apps that have come out. And I think there may even be an app for that lower level. But, you know, just like there was a MySpace? Yeah, yeah. Facebook, right.

John Corcoran  3:55  

So she brought this up, you’re taking classes in entrepreneurship. And you bring it up with your professor, what does this professor say?

Pat Costello  4:02  

I sent it to him via email, because I was just kind of inspired by the idea and the experience that I had. And he just absolutely shot down, said it was a terrible idea. And, you know, didn’t make me feel great about it. And I was so frustrated and resonant about the concept that I you know, fire back and then you kind of back down a little bit, and then we kind of went back and forth. And anyways, I didn’t end up using it as our idea for the class just because it seemed like that class was focused on pushing, like a sustainable, environmentally friendly entrepreneurship concept, whether it was said or whether it wasn’t but anyways, it was a very interesting experience and not the most pleasant one to kind of start my entrepreneurial journey off of. But I was definitely appreciative to even have the experience of having an entrepreneurship class, because I know that that class wasn’t even a thing just a couple years prior.

John Corcoran  5:00  

I have a BA in English, so I certainly wasn’t taking that kind of stuff could have used it. So you go and you know, you’re fourth generation in insurance. Did you grow up like, you know, looking up to your dad and thinking like, I want to go into this? Because it’s funny that I had a very different experience. Like my dad used to make fun of insurance like as a job like it was boring, uninteresting. In adulthood, I’ve come to the conclusion that it is the most brilliant business model as of all of them. And I wish that I’d grown up in a situation where we it had been revered, because now I look at people that had been doing insurance for a while they sell they get paid. You know, it’s just seems like an amazing business model.

Pat Costello  5:42  

I appreciate you saying that, John, because it’s still have a little bit of that reputation. I think it’s primarily just because people think of a product they don’t necessarily want to buy, but they have to buy with their car insurance, with their homeowners insurance, with their renter’s insurance, etc. But I grew up with a dad, who I can literally remember when I was learning to spell words like insurance is one of the one of the words that he tested me on to spell. He’d always say the phrase, no one has endurance like the man who sells insurance. He was and is a great insurance salesman, and he has the book of business to prove it. But that’s how I got integrated into the insurance industry. And my brother and I both started working for our dad’s Insurance Agency in Marion County, in San Rafael, California, when we were in high school, and then in college, and the duties that we had shifted from everything being the receptionist, to doing direct bill to, you know, random tasks around the office to cleaning the office, to getting our insurance licenses and selling and setting up meetings for him. So it ranged but that’s how I got a taste of it. And then coming out of school, I still didn’t know I wanted to be in the insurance industry, it was tough to get a job coming out of college in 2012. And, you know, I was literally working at Sports Authority in Marion County. Sports Authority Elite, if anyone’s been there in town center, no longer there. But I was working there selling shoes while applying to jobs. And I’m I must have applied to three to 400 jobs. And the first one that took me was this insurance company called ACE that worked in that had an office in downtown San Francisco. And frankly, I was hyped up. Because I know I the ability to move into San Francisco, you know, live with my buddies and get a job that was training me within the insurance industry. So that was my first foray into this world.