#TextGen Episode 1 Interview with Will Montgomery

James Martin
Published on | 
February 2, 2021
#TextGen Episode 1 Interview with Will Montgomery


In our first episode, I interview Will Montgomery, the Director of Growth @ Rally.

He shares his story, why he does what he does, and what he has learned along the way (including his biggest failure!)

Text WILL to 24365 to connect with him personally and post in the comments what you learned. Feel free to ask Will anything. He loves answering hard questions. 😊

You can watch the video in the #TextGen Group.


#TextGen Podcast

James (00:12):

Hello there. I'm James with #TextGen, and this is our very first episode, Episode 1, and I am excited to introduce you to Will Montgomery. He's our Director of Growth here at RallyCorp and one of the founding members and team members of #TextGen. I think you'll enjoy getting to know Will. I asked him a handful of questions. We started out with an attempt to do 10 questions in 10 minutes, but that turns out to be the impossible ask. So we get it to 20 minutes, which I'm quite proud of. But we'll go into a little bit of Will's story, his North Star and of his ''where'', his ''why'', where he hails from, where he is, and what got him to do the work he does. We'll then do what a little bit of a deep dive into kind of his career in development role here.

James (01:00):

And what has he learned in talking with countless nonprofits of all sizes, particularly during the pandemic. Will came on the team back in March of 2020. Of course, he and I worked together before so we have years of experience in service together. Will, in his role here, has been the front and center through the pandemic, really helping organizations move to virtual events and look for creative ways to engage donors and volunteers, particularly with all the downward pressures of the market, of the pandemic, of all the challenges we had in 2020 being what it was. So we're going to do a deeper dive with Will. We'll get to know him, spend a little bit of time unpacking his story, what makes him tick, and what he learns most. Let's get started with our first episode here at #TextGen. We'd love to hear your thoughts and your comments, so feel free to post anything. If you'd like to be a member or a guest in our next episode, please reach out and let us know. We'd love to hear from you and meet you as well. All right, let's get started with Will.

James (02:00):

Hey, there. I'm James with #TextGen, and I am excited today to interview Will Montgomery. Hey, Will.

Will (02:08):

Hey, James. How are you doing?

James (02:11):

We'd like to call this series, Will, 10 and 10. But for our audience, I'm not sure if they've ever interviewed anybody in development role, but the fact that we can get 10 questions in 10 minutes, that's to be seen. Between the two of us, we might just run our mouth. What do you think?

Will (02:24):

Yeah, it's a lofty goal. I love how you forgot my last name at the beginning, even though you've known me for years, James.

James (02:31):

I didn't. I said, ''Will Montgomery''.

James (02:32):

You were like, ''Will...'' But that's okay. I loved it. No, it works.

James (02:38):

All right. Well, I do have to copy and paste it all the time because spelling Montgomery's a lot harder than it sounds.

Will (02:44):

It is. It's like...

James (02:45):

Actually, for an old Dallas boy like me, I'm not the sharpest tack in the bunch.

Will (02:50):

Are you already insulting the south, our first minute here?

James (02:51):

[Laughter]. We're going to get rolling. Hey, listen, let's get on here. I want to learn a little bit about you. So why don't you just introduce yourself, tell us your story. Let's let's hear it.

Will (03:04):

Sure. Thanks, James, for having me, and thanks for allowing me to be a part of the group. Obviously, text messaging, but technology as a whole, is something I'm passionate about and have been since an earlier age. It was actually my younger brother, who is smarter than me, and got me into computers and technology and phones. If it was a gadget, we would take it apart, put it back together. We're really interested in it from a young age. Of course, I grew up before cell phones. I was born in Southeastern North Carolina to a wonderful family and grew up there for years, then ended up going to college where I majored in English. Of course, that's why I have my library background there. I've got to use my degree for something, even though I work with non-profits now.

Will (03:56):

However, it's good to know some grammar I've found, but please don't judge me the rest of this, if I do. I moved around. I ended up going to different places and searching for a career that I was interested in, something I believed in, but also something that would make an impact. We hear that saying, a lot of those phrase. But truly, I wanted to go beyond that and accomplish it. I ended up moving different places, met a lot of different people -- some in Silicon valley, some in San Diego, L.A., New York, different places and ended up, throughout my twenties and thirties, searching for a career identity, if you will, and a purpose. I ended up meeting James at another company that he had helped create, and he was an incredible mentor for me.

Will (05:04):

We only worked together for a little bit there.

James (05:07):

Not very long. Yeah.

Will (05:08):

Yeah. But I learned a lot in that time. James had been in that space for years - technology - and working with non-profits, churches, charities, causes, and all the above. When I had heard what James was doing with Rally and with text messaging in general, it really intrigued me. With the pandemic coming on, when it did, it just seemed like the perfect timing. It seemed like people are going to be using their phones and, specifically, texting each other more than ever. It was what really appealed to me. I've been with James now for a year in Rally. On a personal level, I'm married. I have three wonderful children and a beautiful wife who lets me pretend like I'm an avid reader here and back here. I'll mention the background 10 times, I'm sorry. I think it's so cool.

James (06:19):

I'm just surprised you figured it out, frankly.

Will (06:21):

Yeah. In this day and age, I help James and the rest of our team here. I'm the director of growth here at Rally. My job is to make sure non-profits succeed ultimately through some various ways. See, this is the rambling, James. You have to cut me off.

James (06:43):

No, you did good. You kind of hit on this already, Will, but I want to make sure we just dialed in just real quick. What is your North Star? What's your purpose? We're all about purpose. I'm a purpose-driven guy. What is your ''why'' and your purpose?

Will (06:57):

Yeah. That's a fantastic question. I feel as if the older I've gotten, maybe the more complicated it's become.

James (07:08):

Welcome to the club.

Will (07:08):

Yeah. However, we'll keep it simple. I think growing up, ambition was something that I focused on. I wanted to take over the world in my 20's. Then when I got to my 30's, I started realizing that perhaps there were worthy things out there that may not have led to the financial gain. But I've never really been about that. I've wanted to do something that mattered and something that meant something.

James (07:46):

Got it. Makes sense.

Will (07:46):

Yeah. With what I do now, I'm able to help non-profits raise money, and I know that money is going to something good.

James (07:57):

Will, I often get to the ''why'' question. I'll ask people like, ''Okay, if I gave you a million dollars, what would you do with it?'' I'm going to ask you that question. But given inflation and the strength of the dollar right now, I'm going to say $10 million, because I'm afraid if I say a million, you're going to say, ''Well, I got some debt, and get a house and the family.'' Let's say somebody gives you $10 million or even a billion dollars, what do you do on a global scale? What do you do nationally, in your community? What does Will do with that much money?

Will (08:25):

Wow. Is it all right if I give my mom like a thousand dollars of it? Is that fine?

James (08:35):

It's your money. You could do...

Will (08:35):


James (08:37):

Yeah. Uncle Sam is going to take his piece, to be clear.

Will (08:40):

That's true. From a dream perspective, I think one thing that I've been touched by personally -- and I love to hear stories from all of the clients we work with, of course, and they're all admirable causes -- but something that hits home to me is homelessness in our country. I feel as if I've had some really powerful interactions with the homeless community throughout some volunteer work I've done and in just coincidence. Honestly, I'd probably -- I'm just going to keep it real here, James -- I'd give them $9 million. I'd give homeless foundation $9 million. Of course, I know several so maybe we'd split it up. Then I'd have to use the million to kind of lock away my future.

James (09:32):

Exactly. That's why I said 10 (million).

Will (09:32):

I needed my kids to go to college. They're smarter than me already.

James (09:37):

All right. Will, this question is designed to get out of all the layers of pretense to get straight to the heart. I'm going to ask you a harder question here, right? You ready for this one?

Will (09:47):


James (09:47):

You're sitting down, right?

Will (09:49):

I am, in my library.

James (09:52):

In your career, what's your biggest failure? What's something you look back on and you think, ''Man, had I been able to avoid that, that would have maybe prevented a lot of pain in my own life,'' what would that be? You could use your development role, your roles in churches, whatever aspect of your career you want to pick up on.

Will (10:10):

Well, I have too many to really talk about, and that's bad. But I also believe that failure is one of the greatest teachers. While at the time failing it, whether you know it at the time or after the fact, after the dust settles and you get months, years, you can look back and say, ''Okay, this has taught me a great deal more than what I lost.'' For me, I'd say that it's not a particular failure. I've occasionally let customers down. I've said the wrong things. I'm human, right? I may sell it to this price or it's that term, and occasionally that gets confusing. But for the most part, just learning to put myself in the client's perspective, I think a lot of empathy is something that I've tried to learn that I didn't have necessarily in the beginning of my career. I'm kind of dodging that question without embarrassing myself .

James (11:25):

No, you're doing good. You and I are reading a book together right now because, as you mentioned earlier, we're both avid lifelong learners and readers. The title of the book, ''Sell the Way You Buy'', is that what you had a chance to meet that author or even some coaching group that we're part of? It just really hits on empathy. I think in any development role, whether you're selling products, services or helping a non-profit develop funds, fundraising, it really is about empathy, right?

Will (11:50):


James (11:51):

Understanding and treating people the way you want to be treated. Do you find that that's true even with the use of technology? Do you feel like people want to use technology the way...? Is that pretty universal truth, ''Do unto others as you have them doing to you?''

Will (12:06):

Yeah. I think you have to use technology at this point. If you have to use it, let's use it for good and do it. That's why I love this group so much. I'm excited to hear about the ideas that come about and the conversations that we get to have with the other leaders that that will be a part of it.

James (12:30):

All right, Will. Well, we're down to the last two minutes, and we're going to probably stretch it by a minute, but I'm proud of you. You're doing really good. We're actually pretty succinct.

Will (12:38):

Yeah, I'm surprised.

James (12:38):

That's nice. You'd mentioned you talked to a lot of (people) every day, all day long. The previous company we worked in together was serving nonprofits and churches, right? We have, between our entire team, 20 something years of experience working. What is something that you hear most often in talking to these organizations? What challenges, opportunities, pains, fears? What do you often hear and kind of unpack a little bit for us.

Will (13:06):

That's a great question. Shameless plug for a blog post I'm writing.

James (13:13):

I didn't know. That's great.

Will (13:13):

There you go. I know. I haven't talked to them yet.

James (13:15):

Okay. That's a surprise.

Will (13:15):

I'm on the phone with some of the smallest to the largest non-profit organizations every day. I hear most often about their challenges throughout this pandemic, not only from a professional level, but from a personal standpoint, coronavirus has affected all of us in some way. Hearing from them on how to pivot from, ''We're shutting everything down'', ''We're having to work from home'', and turning it to more of a virtual space -- and I think that's what we're seeing a lot. We're hearing about virtual galas, we're hearing virtual events, virtual fundraisers, and some of our clients are getting extremely creative.

Will (14:08):

But everyone, it seems, is at home and has been for the last several months. I also hear things about, ''If we're shut down, how do I build engagement? How do I acquire more donors? How do I stay in touch with the people that have donated in the past?'' It's through technology. Social media, email marketing and, of course, text messaging. But I would say those are the two main things I've heard just talking about their donors and staying touch with the people that care about their organization. That's important in this time.

James (14:57):

I love it. You know, Will, one of our mantras here at Rally is "it is people and process than product", right? Technology, tactics, all that comes last. It's about being human, being relational, treating people the way you'd want to be treated, having empathy, and raising awareness, I mean, connecting with people where they are. It would be unloving and unkind for me as a leader if I engaged an audience in such a fashion that they wouldn't want me to engage them on, or that's not an effective means to raise attention, particularly if my job is to get attention and to keep attention. I have to explore those things. But before we get into technology -- and this will be my last question, and we're probably right out of time here, but as we look at #TextGen, the future for us working together on this new group, from my vantage point, really what sparked this excitement for me is the thought that we can talk about mobilizing people really well beyond just technology and tactics, but get into the heart of what that means to get people to move towards action, right?

Will (15:59):


James (16:00):

And we have a different titles for this group. I think at one point, we had non-profit leaders moving people to action, technology for good. We played with all those ideas. But the notion of mobilizing people really, I think, resonates with you and I. So as you think about it and frame it in that context, what does the future hold for you, for this group, for us? What do you see that looking like in the next 2, 3, 4, 5 years?

Will (16:25):

I think we need to prepare more zoom virtual meeting backgrounds. That's what I think is going to happen. But on a serious note, that's a really, really good question. I feel as if the future for now is going to stay online. And we've seen things with technology that can be negative. They can have bad implications or whatnot. But we also, coming from our standpoint, being people first, we know that technology can be used for good. We know that it is going to be more effective than ever, whether I'm on my phone or I'm checking a social media account, or I'm getting that latest email. I would just say prepare for more of the same and prepare now, because again, we may not return to what we used to think as normal. This may be the new normal or parts of it may last, and that's not bad. We can take it and use that for good.

James (17:40):

Yeah. I love it, Will. It's a great. I'd be a great closing reminder, and this is what I heard you say, is that it's really about using our pain as talked about your failures earlier and learning from that. Never waste pain. I mean, the only way to level up in leadership level as an organization, to level up personally, is to confront pain head on, to honor it, to respect it, to recognize that it serves a purpose. That's not, obviously, in the driving seat for long. But but to honor and have some empathy for yourself and compassion for yourself and compassion for others. Then as you look at technology or tactics or methodologies or strategies and all these other buzz words that we can talk about, I think at the end of the day, it's about leveling up our leadership, leveling up our organization, leveling up our strategy to really put people at the center and to engage them in a meaningful way, and then we engage in conversation, right? Will, you've done well. My information is up on the screen here, this side. Text ''James'' at ''24-365''; 24 hours a day, 365 days a year to get my V card, which dropped me into your phone, my personal cell phone, if anybody has any questions. But how do people get ahold of you? Do you have a fancy little number like that? I got to figure out which side.

Will (18:51):

Carrier pigeon. No, carrier pigeon only.

James (18:54):

Okay. Just wrap it on the little leg.

Will (18:54):

You have three to four month delivery time. No, I'm kidding. They can text ''Will'' to 24-365 as well. And that's two LLs. Text ''Will'' to 24365. That's the best way to get ahold of me. Of course, all I do is work and change diapers right now. So it works out. I will respond immediately.

James (19:20):

I love it. Well, we may have bitten off more than we can chew, Will. I'll close with this. We're both on LinkedIn and Facebook with this group. So we'll see which one does better and probably end up focusing on one or the other. But you can also text #TextGen 24365 for a link to both groups. If you have any questions we'd love to love to hear from you. But post in the comments below. If you have any takeaways from this time or if anything resonated with you, if you're interested in jumping on a podcast or a vodcast -- is that still a work? Can we still say "vodcast"? It is, right?

Will (19:51):


James (19:51):

I feel my age a little bit.

Will (19:53):

I don't know what's cool anymore.

James (19:53):

I don't either. So if you want to get on Twitch TV -- I'm just kidding. If you want to get on with us and talk and share your story, we'd love to meet you. If you're in a non-profit leadership role or in a development role, we want to hear about your cause, put you front and center. You may not be a client to Rally. In fact, you can even be a competitor because we just want to be in service and help those that are serving those that serve. All right. Well, Will, I think that's it. Any closing thoughts before we close this out and roll the credits?

Will (20:24):

No, I think we're good. I'm just going to pick a book back here, if you can see and get to -- no, I'm kidding.

James (20:31):

You know what? I will say that I'm surprised you figured -- you're not a very technical guy. So the fact that you figured out the 3D background or the whatever they call it, virtual background, I guess I'm not taking it.

Will (20:40):

Yeah. Texting, easy; zoom, hard. That's the way I think of it.

James (20:46):

That's right. All right, Will. Always a pleasure. I will talk to you in a few minutes because well, we work together.

Will (20:51):

All right. Thanks, James.

James (20:51):

See you. Bye.

Will (20:52):

All right. Thanks, James. Bye.


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