What About Improving Major Donor Fundraising? – Dante Vitagliano (Trailmapper)

Dante Vitagliano:

Not every donor prospect needs to receive every email, and that most especially applies to the major donors.

Eric Wilson:

I'm Eric Wilson, managing Partner of Startup Caucus, the home of campaign tech Innovation on the right. Welcome to the Business of Politics Show. On this podcast, you are joining in on a conversation with entrepreneurs, operatives, and experts who make professional politics happen. Today we are welcoming Dante Vi Tago back to the show. He's the founder of Trail Mapper, whose software helps Republican campaigns upgrade their major donor fundraising program. We last spoke to Dante in November, 2021, and you can listen to that episode via the link in our show notes. In this episode, we're getting caught up on his progress hearing, his lessons learned, and sharing advice for new entrepreneurs. Dante, welcome back. It's been about a year and a half since we last had you on the show. So give our listeners a bit of an update on Trail mapper and and what it is you've been working on.

Dante Vitagliano:

Yeah, it's been a while. It's, it's crazy, I can't believe how fast it went since we last talked. We had our product Prospector Pro in the market for a full election cycle now. So our focus now is on version two, which means we're distilling down the learnings from the dozens of users and hundreds of thousands of data points that we collected in 2022 to continue to build a better product

Eric Wilson:

And remind folks, or, or maybe introduce for the first time what Prospector Pro does.

Dante Vitagliano:

Yeah, prospector Pro is a major donor fundraising operating system, so we call it the SWAs model software with the service. We help connect candidates campaigns, principles of organizations, nonprofits, trade associations, and advocacy groups with the funders, the major givers who are going to be most likely to be receptive to their message. So we have software and data. If you think about sort of a Venn diagram with three circles like software, data and services, we're kind of at that, the intersection of those, those three.

Eric Wilson:

Got it. So just so folks understand, this is not about online fundraising, even though it's a cloud-based application, this is more of your, your donors who you need to build a relationship with that you need to contact and reach out to.

Dante Vitagliano:

The very first thing I tell every new customer when we, we talk to them for the first time and demo the product is the first thing you should know is that this is a major donor fundraising product. We focus on people who give a thousand dollars or more and typically have given, you know, 15,000 at, at a minimum of the past three cycles. So major donor fundraising is obviously very different from a small dollar. There's a different approach, different strategy, different tack you have to take with, with converting major, major donors. So we're, that's, that's the area that we focus on. We found that this was the area of sort of modern campaigning that was most in need of innovation. And so that's where, where we're focused.

Eric Wilson:

Do you have a hard time kind of breaking out of those expectations? You know, I find this as, as someone who worked in digital marketing for a long time for campaigns, when I go to talk to them about, you know, software and other things, they think, oh, this is a, this is a digital thing. It has nothing to do with field or finance or political or comms. Do you have that challenge when you're reaching out to campaigns?

Dante Vitagliano:

I think the biggest challenge is educating them on the distinction between the two. There are tried and true methods that work in the digital space and small dollar space that simply don't work for major donor fundraising. So distinguishing between the two. I I find that our users are often confused. They think one message or strategy or tactic, it, it works for small dollar, so it it, it will work for the major donors. And that's, that's just <laugh>, just not the case. Yeah. You know, it's a, it's a very different audience that we're talking to and we're actually making very different asks, you know, the difference between a $25 ask and, you know, a $2,500 ask is, you know, couple zeros. That's, that's no joke.

Eric Wilson:

We've had a number of conversations on this show about the grassroots small dollar fundraising problems that Republicans are facing. But since you're focused on the other end of that spectrum, what is the outlook there? Are we seeing similar donor fatigue? Are they tired of some of the tactics that are being used?

Dante Vitagliano:

Without a doubt. We collect a lot of data. We have lots of conversations with the funders that our users are, are connecting with and asking for, for contributions. And almost universally donors are tired of the deluge of texts and emails. But as far as solutions go, the many of the digital practitioners, if you will, that you've talked to on this show, they've been, at least from my perspective, spot on in their recommendations, which I think namely is just segmenting your lists. Like, you know, I've heard on your show, not every donor prospect needs to receive every email, and that most especially applies to the major donors with whom you're trying to build meaningful relationships, you know, and getting them to part with, you know, four or five figures of their hard-earned money and, you know, potentially host an event you know, introduce you to their friends and family and bundle some checks together. So I certainly wouldn't want to encourage any of our users to use the same strategy. So major donors are accustomed to giving thousand dollars checks, but they're not going to respond the same way to the same sort of emotionally charged appeals that a small dollar giver might. So I think it comes down to data management.

Eric Wilson:

Yeah. Well, I I think it also has a lot to do with, you know, your understanding, their motivations. Why are they giving? Is it to, to build these relationships? Is it to go into these fundraisers? Is it to be able to maintain your, your business ties with, with someone who's, who's running you know, that you may know professionally? The other end of it, of course, is from a campaign perspective of looking past the dollar figure for a supporter. You know, we're, we're obviously focused on, on voters, we're focused on donors, we're focused on volunteers. I think a lot of times campaigns don't realize that those can all be the same people. And to your point, you know, yes, someone maxes out, well, they can also bundle, they can host, they can recruit new people, really valuable stuff that if you didn't have software like this to manage those relationships more effectively, you'd be missing out on.

Dante Vitagliano:

I think the, the key here for us and the, especially this cycle, our priority has been that, you know, the meaningful relationships at scale and both an emphasis on the, the meaningful relationships aspect of it. There's I think in the professionalization of campaigning, we've built great products that allow you to scale outreach infinitely. And we want to build meaningful relationships at scale, but not scale at all costs. If there's one thing that we've learned about the major donor population over the past two years collecting all this data is that it's a really unsatisfying insight, which is that every donor's different. I think we get a lot of questions about like, what are what are donors thinking about these days and or what are the, the top issues? But every donor's different. The way they like to be communicated with is different. Their priorities are different, their expectations, their motivations, their attitudes preferences, all of those things, everyone's different.

So being able to construct a, a strategy that is generally applicable across the major donor population that you're prospecting from is important. But then also having the tools and capability to drill down and get more specific for individual donors. And so if, you know, for example you know, this guy's a big texter. You know, he's, he's not trying to take, you know, phone calls. There's plenty of of donors who've never had a conversation with any one of our users on the phone, but they have communicated via text and, and they give, and you know, to me that seems kind of weird. But, you know, to to to, to them, obviously that's just their, that's their preference. And there are, you know, other donors who they, they have completely different motivations. Sometimes they just want to be heard. Sometimes they want to test your, your issue positions and, and see if you're, if they're aligned. But not every, not every donor has the same sort of motivation. So we, we want to craft a strategy that is generally applicable, but then also can be adapted to, to specific sub audiences, and then even more specifically to individual donors, treating them human beings is really what it comes down to as opposed to ATMs.

Eric Wilson:

Dante, I wanna shift gears now and talk more about the, the business and the process of building trail mapper. So, what's been the most surprising challenge that you've encountered while, while scaling, since we talked to you 18 months ago?

Dante Vitagliano:

Well, this isn't really a technical challenge or a business challenge per se, but one thing that we have been focusing a lot a lot lately has been how do we build a product that encourages our users to step outside their comfort zone if left to their own devices? Most candidates are gonna come up with a platform that is generally in a message that's really similar to everybody else out there. And I wouldn't say that major donor fundraising is quite a zero sum game. It's, it's not like that, but it is competitive, and every user on our platform is effectively competing for donations with the other thousands upon thousands of people running for office up and down the ballot. So, you know, breaking through the noise is particularly important. Obviously, you want to capture interest, inspire and, and motivate people, but it needs to be unique.

And so building product around that has been a challenge. What, what can we do on the product side to encourage our users to think differently and not just fall into that same sort of mindset of the, the quote unquote smile and dial, smile and dial is this phrase that has been repeated and political fundraising for ages. And it implies, you know, you have to just put your nose down nose of the grindstone and just call, it's a numbers game only. Well, is it, you know, or, or could we, can we be more efficient? Right. Can we be more effective? Well,

Eric Wilson:

It goes to this problem or this challenge of expanding the pie, right? So that, that, that process works for a certain group of donors, but it's not gonna bring people who necessarily are unique to you like your network or people who are excited about your campaign. The same thing that we deal with on the online grassroots fundraising, which is, you know, if, if you could block off the logo and the paid for on most campaign fundraising emails, it could come from any campaign out there. There's just no unique branch to it,

Dante Vitagliano:

Right? And I don't see how that type of message is going to distinguish you from the other, the other guy also asking the same people for, for money. The major donor population in the US is relatively small,

Eric Wilson:

And so campaigns don't have this unique brand is really hard to stand out.

Dante Vitagliano:

That's absolutely right. And, and one thing that we've been working on is trying to tease out those unique aspects. Every user on our platform is different too. And sometimes we'll learn two, three months into an engagement with a, a user on our platform that they were a game show contestant <laugh>, and they won a bunch of money. Well, I mean, that's interesting. That's unique. That's different, you know we had a, another user who had took us several months before he, he revealed that he was at ground zero digging people out, geez, looking for survivors. And, and nine 11 is like, how did you not mention that yet? You know, this is, this is not something that everyone can say. Everyone can say what their issue positions are. Oh, I, I'm gonna, you know, lower taxes, you know, ex reduce the size and scope of the federal government. Sure. I mean, so do the rest of us. What makes you unique? Put your mind in the major donor's shoes. What can you do to distinguish yourself from the crowd?

Eric Wilson:

You've got a much larger team now, Dante, than when we first spoke. And, and from a mindset shift, how do you take that leap from it just being you and maybe some contractors to help you with the software, to having real employees having to maintain a payroll, because that is one of those zero to one type moments in a startup. I think it's challenging for a lot of people to overcome.

Dante Vitagliano:

Well, we're a fully distributed team, so that presents its own set of challenges. Many of our employees across the country never met. In fact, just a, a few weeks ago in, in DC I got to meet some people who had been working with us for a better part of a year and a half to two years, <laugh> for the first time. It was really cool. I know it's super buzz wordy, but things like creating company culture, distributing knowledge and resources across the company, and then aligning the team around company objectives, those are challenges that we basical every day distributing responsibility. When you grow, or at least in our experience, you go from having tasks to complete, to having teams responsible for tasks. So for, for me, my job is less about getting things done and more focused on just empowering the teams within the organization to get their job done effectively.

Do they have the tools and resources and how can we do things more effectively, make their lives easier? Also, quality control. It has emerged as a, as a new focus. I kind of think about it in, in terms of like Maslow's hierarchy of needs, and I'm not sure that if that's a great analogy, but once you, once your basic needs are met, which for us means is the product working as intended, right? Bare minimum, you know, expectation. And beyond that, it's, once you, once those needs are met, now you can start thinking about optimization, thinking about improvements, iterating, and, and making the product more effective, easier to use, better experience for the customer. So those are some of the main challenges that, that we face as we continue to grow. But,

Eric Wilson:

So it's kind of like you're shifting from being, you know, a performer to being the conductor of the orchestra, right? You're not actually making the music, but you're making sure that everyone else is,

Dante Vitagliano:

It's a challenge for some, for, for, for at least I can, you know, speaking for myself, for folks that have thrived in the performer role mm-hmm. <Affirmative>, right? Like when, when you take full responsibility over your domain and whatever, whatever is under your responsibility to just making sure that the trains run on time and, and everybody has, has the tools that they, that they need. So there's an infrastructure around internal communications that we have to build. We're thinking a lot about, about collaboration, and I know we're treading into the buzzwordy territory here again, but you, you eventually realize that, that there's a reason that these big companies use so many buzzwords is because that these are the challenges that they face. How do we standardize information and documentation across the organization? How do we make sure that everyone's aligned and that we're all rowing in the same direction? I think one thing that we've done really well is instill in our team this core value of collecting, collecting feedback, collecting data and, and collecting data, generally collecting data within our product, collecting data from back, from our, from our customers and listening to our customers. That's something that is pervasive at all levels of, of the company from, you know, our CSRs to our leadership team, even on the development side, the technical team all focused on taking user feedback to help build the better product.

Eric Wilson:

You're listening to the Business of Politics Show. I'm speaking with Dante gli, founder of Trail Mapper. One of the things that trail mapper devotes a lot of time and resources too, is creating content. You've got an active blog, you make videos, you talked about your survey data. Why is that so important to the company?

Dante Vitagliano:

Yeah, well, first of all, thanks for appreciating that cuz it's, it's not, not a lo it's a good amount of work. You know, it's, it requires attention and which, you know, is

Eric Wilson:

Well, yeah, I mean resource, you don't have to tell me. I, we, I've got the podcast of the newsletter

Dante Vitagliano:

And all that. I don't envy you. And that's, and that's one of the reasons why I haven't committed myself to a to a proper podcast. Although we do try to, to host podcast style conversations to have, you know, interesting back and forth with, with people. But but content marketing really just kind of aligns with our core values. One of them being transparency, you know, as a lifelong campaigner, the majority of my professional career has been on the other side of the desk as it were, right? And one thing that always sort of irritated me about the industry is how cagey everyone is,

Eric Wilson:

Right?

Dante Vitagliano:

<Laugh>, everyone just seems to play really close to the vest. And we, we don't take that position. We try and, and do the opposite. We try and share our learning, share our experience and our insight. Ultimately it helps our customers and frankly, as a new company, we know that it's our job to build trust with the community that we serve. So producing content that users and potential users hopefully find valuable. It just sort of makes sense.

Eric Wilson:

And it has to help you with customer discovery, right? Like people will find you from that.

Dante Vitagliano:

Absolutely. I think there's also the novelty aspect, how our offering offering is differentiated from, you know, existing alternatives in long form content. It's really kind of hard to explain to somebody. That's why I, you know, I always kind of bristle when someone says, give me your elevator pitch, <laugh>. It's like, yeah, well, I mean, it's major donor fundraising, but just less miserable, right? And that's, that's not super satisfying, that's not super informative, but the long form content allows us to better explain what differentiates our product from the existing alternatives. So it, it's, it's been fantastic strategy from a user acquisition perspective for sure.

Eric Wilson:

Well, I mean, that's one of the pieces of advice that I give to people who are coming into this market, where you've got people who are, are, are decision makers who are very busy. They're, you're, you're right, there's not a lot of content out there about our profession. And so it really is, if, if you're trying to build something and you wanna make it past the inbox, you know, filters the gatekeepers, creating content that's valuable and interesting to your target audience is, is the way to go. What, what are some other piece of advice? What's some other advice that you would share to, to other, you know, perspective entrepreneurs or people who are early on their journey about maybe a mistake that you, you should have seen or wish you'd have seen and, and avoided?

Dante Vitagliano:

Everyone always has talk to customers, but I'll, I'll, I would take it a step further and say, don't make excuses when it comes to user feedback. Mm. Okay. So when you're, when, when every piece of feedback, whether you, you, you have to take the emotion out of it, you are not the product, right? As a, as a, as a team member on a, in a startup, you, the product is, you know, in some ways it is a reflection of your work. But you have to divorce those two things because the, the feedback, regardless of whether you feel on an emotional level that it's warranted or valid, it has to come from somewhere. So, you know, look past the, the words which may offend you or, you know, irritate you and, and think about what is the problem that they're trying to solve, but they don't feel like is being solved. And how do we, how do you improve the product to, to make that better? So not not making excuses, prioritizing user feedback is, you know, sort of a, it's trite at this point. Every, everyone knows that you have to do that. You have to listen to customers. Well,

Eric Wilson:

They, they know that you've gotta do it, but it's, it's hard to do. And honestly, one of the challenges that, that we face in our industry is you don't get that many bites at the Apple reputationally for getting user feedback. You know, they're, they're probably only a handful of people that you and I work with who if we screwed up royally would give us a second chance. And so I, I do think there's a little bit of tension and reputational risk there, but that's really the only way you're gonna break through.

Dante Vitagliano:

I think you have to be a, a little bit more resilient when, when taking on reputational risk, because you're never going to learn if you're not putting the product in user's hands to to start getting feedback. And a customer churning is not the end of the world. Mm-Hmm. <affirmative>, as long as you're go directionally correct, as long as you're moving in the right direction, as long as you're, you've learned something from that experience and you're making the product better so that you can reduce your increase retention, reduce your overall churn, and serve customers better so that the better experience they get, the more likely they're, they're going to stay.

Eric Wilson:

Yeah. Another thing that another area in startups and, and particularly this industry that involves a lot of learning is pricing. It's a big question that entrepreneurs are always asking me, and my advice is, put something down on paper, get customers to respond to it. You know, if they say, Hey, look, I I really wanna use your software, but this is a problem for us on the pricing front, then they've now just tell you how to price your product. So that's, that's where you wanna get to. What was your product pricing journey like getting to, to something that that really worked for, for users, for trail mapper?

Dante Vitagliano:

Yeah. it, it, it is has been a journey. Absolutely. and you could, you know, throw something down on paper and, and then adapt from there. And that's, that's essentially what we did. When we first rolled out Prospector Pro, we threw down what we thought was a no-brainer pricing model, <laugh>, and I suppose it was similar to like a cost plus strategy in terms of it is basically the lowest cost that we could financially stomach, because frankly, we needed the new users, right? So that we could start getting feedback and we quickly transitioned to, you know, something more like a hybrid between competitive pricing model and a value-based pricing model with, you know, competitive pricing, meaning tailoring your price versus ex existing alternatives, right? And then the value based pricing being how well the solution at its current, current price meets the needs of our users. So for our users, the priority is cash on hand, at least for our product. The priority, what they're looking to get out of it is, is cash on hand and not just total dollars raised. If, if your goal is just the raw number in terms of what you get to report at the end of the quarter, then there are other solutions like digital that could potentially be a better fit if you don't care about how much cash you actually have, right?

Eric Wilson:

You're, you, you don't care about net. Yeah.

Dante Vitagliano:

So with that priority that, that's, that has been, that's what has made our pricing model, you know, what, what it is today. We, we do offer custom pricing, but we have a, a tier pricing model that can accommodate the needs of each different type of user. So sort of scaling down down ballot, you know, mid-tier races. And then of course, our most popular plan, you know, 80% of our users are on our, our top tier plan, which means that they need to raise as much money as, as humanly possible in the short period of time that they have for election day. But I will say one of my favorite parts of this job is the four times a year we get to send out emails to each one of our users with their quarterly ROI numbers. Yeah. So it's something like, congratulations, you received an 850% return on your <laugh> investment in Prospector Pro, right? And I think communicating that value is important. Cause it, it, it, it can be hard to understand the connection between the activity and the, the outcomes, but that's, that's kind of how we approached our, our pricing journey.

Eric Wilson:

One more thing before we wrap up the conversation. I'm always curious about the software apps and systems that people use to stay organized and on track and, and I think other folks could learn from this as well. What do you and your team rely on to, to run Trail Mapper today?

Dante Vitagliano:

It, it mostly the, the same, I I would assume the same sort of products that those companies that at our stage are using. So Slack is, is big. All of our communication, internal communication lives there. Obviously we're a fully distributed team, so that's, you know, kind of like the, the, that is the office in, in Slack. And we use Notion for our wiki or everything Wiki, the houses, our Knowledge bank all of, all of our, our, our data and resources. We actually also use an another app, SaaS product called Super, which turns notion pages into webpages, which is how we, we publish our knowledge bank, both the internal and the external Knowledge bank. So Notion is, is <laugh> mission critical for us, and there's actually sort of a dependency there. So hopefully Notion doesn't go down anytime soon. We use Loom.

Loom is a, a video recording software. And that's primarily used for recording tutorials, knowledge bank resources occasionally that it's used on the customer support side but primarily used internally, Zapier retool or, you know, app connectors. We use between different services and, you know, just like everyone else we're playing around with chat j p t internally anyway for various tasks. You know, Dolly too on the, you know, the, the marketing side, but it's not currently built into the user facing app yet, but we are actively exploring opportunities to utilize, you know, so-called generative AI for different services within the app. But stay tuned on that. Well,

Eric Wilson:

That definitely endorse notion and Loom is great too. So if you haven't checked those out be be sure you can give them a look. My thanks to Dante for another great conversation. As always, you can learn more about him and, and trail mapper with the link in our show notes and go back and listen to the, the first episode and kind of compare and contrast his journey thus far. If this episode made you a little bit smarter, gave you something to think about, all we ask is that you share it with a friend because onus, you look smart in the process as well. That's a great way for people to get to know our podcast, which thanks to your help is growing every week. Remember to subscribe to The Business of Politics Show wherever you get your podcast. That way you will never miss an episode. You can also sign up for email updates at business of politics podcast.com. With that, I'll say thanks for listening. We'll see you next time.

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