Team Member Spotlight: Head of Strategy Ryan Del Mastro

published on 14 February 2023

About Ryan...

So I grew up in the small is not the right word, but nothing town called in Milford, Connecticut. It's about 15 minutes north of Danbury. And I mean, there's just nothing there. Right. It's a bedroom town. But we moved there 96, not 97. Beautiful house, great, great education system. But, you know, that's where you know, that's just where I grew up. Spent a ton of time. Family is still there. And there they are tangentially involved in running up there. Tangentially involved in local politics. My mom's the head of the Chamber of Commerce there. So she gets all involved with everything just by accident.

Yeah. So you start off in politics just naturally, then?

I wouldn't say naturally. My first memory or memory, if you will, of politics is the Bush-Gore election year 2000. It was, you know, coming off the Y2K scare, and I didn't follow the run up to the election, but I have a distinct memory of like election night, Florida not being called and just Brian Williams coming out and talking people through it.

And then kind of the mess that the Supreme Court case was, the expedited Supreme Court case was and the hanging chads just the mess that that was you know, that's kind of like my first core memory of politics. And then it wasn't for another five or ten years that I got reengaged. My my grandfather ran unsuccessfully twice for state representative in Bristol, Connecticut.

And, you know, as his as his grandkid, you know, I'd go over in the summertime and I remember just going around in a 100 degree weather door knocking with him. And he's you know, we have these paper walk books and, you know, dragging me. I'm like ten or 11 at this point around talking to different people. And I mean, look, it was a great time with my grandfather, but I do not miss door knocking at all.

 I've done some door knocking and they can get tired and can get long and dour...


That is a good segue into my first question. When did you become interested in politics?

I've always kind of had the bug, but it's kind of had the political bug. I mean, other than volunteering, maybe with the local artsy, you're getting involved in college. My first job was actually field director for a PAC, and I was placed in the first place in Pennsylvania six, which was Ryan Costello's district at the time.

It's 2018 and then after he decided not to seek reelection, I got relocated up to the first, I'm sorry, the second District, Maine. That was Bruce Poliquin's district at the time. I've met both of them. They're both fantastic gentlemen, and I really wish we had their leadership in the House right now.

What would you say is your favorite part about working at Trailmapper?

So I get to experiment a lot here at Trailmapper. You know, having co-founded the company, I've moved into a position where I'm head of strategy. So I get to work with a ton of great candidates, political action committees, nonprofits on fine tuning their approach, fine tuning, their strategy, timing and getting them in front of the right donor with the right message at the right time.

It's super rewarding to have a client come to us and be like, "Hey, I don't know what you guys did differently, but we just crushed our fundraising quarter" and they just want to say thank you about it. The reality is we don't do anything differently quarter to quarter here, but we set a really good foundation at the beginning.

We build their muscles. I say it's like going to the gym. We build up their core muscle, we build up their fundraising muscles so that when it's time to, you know, bring everything home, they're able to carry that load. They're able to do it, you know.

So if you could give one piece of advice to somebody who plans on running for office, what would it be?

First and foremost, start local. A lot of it I hear and talk to a lot of people that are looking to run for office that, you know, they're trying to hit a grand slam or a home run at their first at bat ever. And it's really tough to do. It's not impossible, but it's almost unheard of, you know, a lot, especially on the Republican side, the center right side of this.

You know, you have a lot of very successful people, business owners, community leaders, Right. Coming out of the woodwork where they've been very successful at one very particular thing in their life. Right. And it's made them very wealthy, made them hugely successful and maybe a titan of industry. But that just doesn't necessarily translate. So I would say start local, right?

Not Congress, but run for state rep, right. Get your feet wet on your school board where you can make those mistakes at a very and it won't cost you as much, but the opportunity cost is lower, but your failure cost is lower as well. I would also say talk to everyone, your friends, your family, coworkers, your personal network about thinking about running for office.

They're going to have a lot of very constructive feedback. They're going to try to connect you because they like you. Maybe they love you, right? They're going to try to connect you with people in the community and they'll have ideas of their own. And the last thing I would say is don't be shy or embarrassed about it. You know, again, when we talk to candidates early on in the cycle, you know, they're like, we got to keep this really, really quiet, really, really hush hush. 

Counter intuitive right? 

It really is. Unless you have some very serious skeletons in your closet. I mean, I wouldn't be I wouldn't be super hush hush with your personal network about, hey, I'm thinking about running for office because, again, going back to running for Congress, you know, your first hurdle, your first big splash should be a week in saying I raised $100,000 from individuals.

Well, that doesn't happen overnight. You have to put in maybe six months of work to organize, get all your ducks in a row from getting friends, family donors, personal network donors, people you know that you work with all those sorts of things. It doesn't just turn on a dime.

What's your favorite quote?

So my favorite quote is take your place in history, Inspire, Soar, Excel. I don't I don't know who I can attribute that to. But when I was growing up in high school and the first couple of years of college, I did something called Drum Corps International. And basically it was 100 days where you would get musicians and dancers together into a specific cause you would toward the country.

And this quote was hanging on a banner, and it's the last thing you see. And the entire tour culminates in Indianapolis, Indiana, at Lucas Oil Stadium. And this quote is the last thing you see before you march out under the 50 yard line of Lucas Oil, where like 20,000 people are ready to watch you. Right. And hundreds of thousands of people have watched you for the entire summer perform this show that you bled, sweat, cried tears over.

It's a very inspiring quote to me. It's what gets me out of bed in the morning. And yeah, it just personally means a ton. I like that. 

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