Inside DealMAX: Talking Investment Banking Trends with Ashton Gillespie

For the third episode of our limited series, “Inside DealMAX,” we’re joined by TM Capital’s Ashton Gillespie to discuss the investment banking space, her tactics for getting the most out of DealMAX as an investment banker, how to strategically say no, and more.

Read a transcript of the podcast below.

Middle Market Growth: Welcome to the Middle Market Growth Conversations podcast, an ACG production, I’m Katie Maloney. This is the third episode of our Inside DealMAX series, where we’re going behind the scenes with guests involved in ACG’s flagship conference for the middle market, DealMAX, which takes place April 7-9 at the Aria in Las Vegas. Throughout the series, we’re exploring M&A trends, what you can expect on the ground at DealMAX, and networking tips from dealmakers and experts who will be there when the doors open. Today I’m joined by TM Capital’s Ashton Gillespie to discuss trends in investment banking, what she’s hoping to get out of DealMAX this year, how entrepreneurship changed her dealmaking approach and more. Ashton, welcome to the podcast.

Ashton Gillespie: Thanks for having me, Katie.

MMG: So to start, can you tell us a little bit about your current role at TM Capital and also talk about what your involvement with DealMAX looks like?

AG: Sure. So I’m a vice president on the sponsor coverage team here at TM Capital. We’re a boutique investment bank focused primarily on sell-side advisory for family-founder-owned businesses as well as sponsor portfolio companies. My personal focus is on building relationships with private equity firms that will be suitable buyers for the companies that we’re selling, but also positioning us to hopefully advise them on their portfolio company exits. And this year I’m so excited to be a co-chair of the private equity outreach committee for DealMAX.

MMG: Great. Yeah, and I was hoping you could say more about what your role on that committee involves and you know, what that looks like.

AG: Sure. So I co-chair the committee with Chris Hebble, who’s been fantastic to partner with. He’s a veteran on the committee, so he has definitely taught me lots of the ins and outs. Our goal is to boost private equity engagement and attendance, not just by the number of firms, but also representation across seniority levels at those firms. So to be able to reach those goals, we’ve assembled a team of industry pros on both the banking side and the service provider side who interact with private equity firms on a daily basis. And it’s Chris and my job to inspire and equip those team members to advocate for DealMAX. Ultimately, we want DealMAX to be the premier event private equity professionals just cannot afford to miss.

MMG: And similarly, certainly there’s compelling reasons for private equity firms to come to DealMAX, but I was hoping you could also speak to, for yourself as an investment banker, why you come to DealMAX and what you’re looking to get out of the conference this year.

AG: Sure. I mean, some people joke that DealMAX is a necessary evil because it’s so efficient and productive, you simply can’t not attend. For me it’s about the quality of connections, especially the chance to catch up with senior partners who may only attend one conference a year. For a lot of them that is DealMAX. So this year I’m looking forward to deepening relationships and connecting with people who aren’t on the circuit regularly.

MMG: And we’re recording this in the early days of 2025, so I’m interested to hear what trends you’re seeing in the investment banking sector as we kick off the new year and maybe some of the topics that we’ll be hearing more about at DealMAX.

AG: That’s a very tough question, and I really do consider this the first day of the new year. It’s a Monday, so we’re officially in full swing. As we enter 2025, middle-market M&A activity remains strong, driven by record levels of dry powder and a scarcity of quality recession-resilient assets in sectors like healthcare, specialty manufacturing and tech-enabled services. At my firm, we’re seeing increased pitch activity focused on portfolio company exits. There were very few private equity exits last year, but as valuations are beginning to stabilize, sponsors are feeling a bit more confident in the market and willing to test the market with their assets. Now, creative deal structures like earn-outs and seller financing are bridging some of the valuation gaps in this higher interest rate environment. But buyers still remain focused on operational value creation through synergies and bolt-on acquisitions. Many firms only were able to do add-on acquisitions last year, so that remains top of mind for a lot of private equity firms. But overall, these trends highlight the resilience and adaptability needed in today’s transactions.

MMG: And that’s consistent with a lot of what I’m hearing too, as far as predictions for an uptick in activity this year. Like you said, we’re in the very early innings of the year, but I think that especially in a DealMAX context, I think that will be a very interesting event, as more of these deals come to market and these conversations continue. In that vein, I wonder whether you have any investment banking-specific tips for navigating DealMAX. I’m thinking aspects of the conference that are particularly valuable to you as an investment banker or maybe tips for other investment bankers who are considering attending.

AG: Sure. I mean, of course the goal for anyone attending the conference is connecting with people. And my advice I should take myself, and I’m very bad at taking this advice, [is] say no strategically. Of course it’s important to have a large number of meetings. Like I said, it’s one of the most productive and efficient conferences that anyone can go to. But I try to prioritize meeting with people who aren’t local to my home office or who I don’t see often on the circuit. And those unique, harder-to-access connections make the trip more worthwhile. So as much as I am bad at saying no and often end up having a fully packed schedule, I think it’s very important to leave room in your schedule for spontaneous conversations, which, quite frankly, often lead to the most memorable opportunities.

MMG: I really like that phrasing too: strategically saying no. I think that that’s a variation we’ve heard on a couple of these other episodes that we’ve recorded where everyone seems to be cautioning: Do not pack your schedule to the brim, leave room for some of these more spontaneous encounters. And I think that that makes a lot of sense to look at your schedule that way.

AG: Easier said than done though.

MMG: For sure. So in preparing for this interview, Ashton, our team learned that you have a background as an entrepreneur and that you founded an activewear brand. I wonder how your experience as a founder impacts your approach to deals or your approach to networking?

AG: It’s a great question. So starting a business was an emotional and financial rollercoaster roller. And when I say rollercoaster, I mean it was a rollercoaster. I had the blessing of starting a business with my mom and we started it to meet a personal need of mine. As you can see, I’m very fair skinned and I needed some protective clothes to wear at the beach and horseback riding and just being outside active in Texas. So we were starting the company to meet a personal need, and starting a company with family is also not an easy feat. Emotions can get very heightened, especially when you’re doing something you’ve never done before. But our business was really a story of a mother and daughter reconnecting, and I think that story resonated with a lot of people. We had a blessing of being on a lot of news shows because people just simply couldn’t believe that a mother and daughter could start a business together. I mean, my mom wrote an a letter to Kathy Lee Gifford back when she was on the Today Show, and her appealing to Kathy Lee’s side as a mother is how we got on the Today Show. So even when we went very far in the red financially and we knew it was time to dissolve the business, we kept putting it off because emotionally it was just too hard to say goodbye. And so for most founders, selling their company is not just a financial decision, it’s an emotional decision. And I think it’s very important that as dealmakers, we are aware of this and have compassion above all else. We are partners to these founders as they go through one of the biggest decisions of their entire life. And emotions can often get in the way of logic, but I think that’s the beauty of, you know, being human.

MMG: What year was that that the business was up and running?

AG: So, let’s see, we were ahead of our time. I think we started it today when people are more focused on protecting their skin, we would’ve probably succeeded or at least done better than we did. But we, gosh, we started it in I think 2009 and ultimately dissolved it in 2015. Funnily enough, it was called SunKissed Girl Activewear, like you’re kissed by the sun and Sunkist Growers, the orange company, sent us a cease and desist, which ultimately led to us having to rebrand. And the very funny part of the story is that we were entirely made in America, but because of the cease and desist, we ultimately ended up selling most of our clothes in China, which is irony on all ironies. I mean, I just can’t help but laugh at that. So we sold our clothes for pennies on the dollar in China, but it was a great learning experience and it does give me a lot of compassion for founders who built businesses that have stood the test of time and they went in the red and got out and were able to overcome those hurdles.

MMG: What a trial by fire and yeah, I mean it sounds like an amazing learning experience, but also a highly stressful one. Were you was that in tandem with your investment banking career or did that inspire you to enter investment banking?

AG: No, I will be honest, I thought at the time that that was going to be my career. I was like, I’m going to be one of these founders who sells to private equity, but ultimately I learned that I like having a consistent paycheck and being an entrepreneur means that your paycheck is the least consistent. So no, it was before banking, but I think it does give me a unique appreciation for the types of companies that we advise and allows me to connect with the founders in a unique way.

MMG: Well, and you mentioned being ahead of your time. As a fellow fair-skinned redhead, I think it’s an amazing idea. And so I wish I knew about it back in the 2009 to 2015 era.

AG: Me too. I mean, I really think that if we had started it today…To be clear, I started it without any college education. So I think if I had had an accounting class under my belt, I would’ve probably done a little bit better, but that’s neither here nor there.

MMG: Well, we talked a little bit earlier about networking and facilitating high-value connections, which is certainly the heart of DealMAX. I wonder if you have any tips or strategies for how to approach networking at an event like DealMAX and how you’ve used the conference to build or strengthen existing relationships?

AG: Absolutely. I think that the most important thing is to approach every conversation with a people-first mindset. You can really tell when someone is just checking boxes versus genuinely engaging with you. And so I focus on building authentic relationships because at the end of the day, many firms have similar capabilities and beyond the brand names and taglines we’re just people, and ultimately people share deals with those they like and trust. And I think that that comes into, one, how do you request meetings, how do you accept meetings and then again, allowing time in your schedule to have those genuine conversations with people. And of course, that’s very hard in an event where people are running around like crazy and just trying to get things done and make it through the day. But I think if you have that intentionality about how you want to approach your day, that it’ll be far more valuable.

MMG: And is there a relationship that stands out that originated at DealMAX through a meeting you had at the conference or a conversation that you had there?

AG: It’s so hard to pick just one relationship, but one that sticks with me is I was actually in the bathroom at DealMAX, or I guess it was Intergrowth back in the day, and a button had fallen off my shirt. And there was a lovely woman who was very well equipped. She had a sewing kit with safety pins and all kinds of things, and she lent me a safety pin to help pin my shirt. And she’s no longer in the industry, but that’s a very bonding moment, when you’re in the bathroom and you just need someone to help you figure out your outfit to get through the day. And we’ve maintained our friendship, and even though she’s no longer in the industry, she’s still a mentor to me and also ended up giving me Band-Aids later in the day when I realized my shoe choice was not a smart shoe choice and I had the worst blisters. So she really came in handy in more ways than one.

MMG: I love that story, and I think also speaks to the women’s connection within DealMAX. I mean, I feel like within the finance industry overall, it’s known for being very male-dominated, but I feel like through, whether it’s just dedicated women’s events within the conference or just the one-on-one connections that you make, there really is a strong community within women dealmakers that that comes through at the event. And I think that’s the perfect example.

AG: Exactly.

MMG: So I wonder, Ashton, if you’ve changed or grown in your professional life in any way as a result of your experiences, either with DealMAX or Intergrowth previously or even within ACG more generally?

AG: I mean, absolutely. Early in my career, ACG events were really one of the few spaces where I could network with senior women in banking and private equity. My firm did not have anyone senior and there was a woman that I could look up to and get advice from. So being able to go to ACG events, DealMAX, Intergrowth, whatever we want to call them, being able to get advice and stories from these senior women has been invaluable and it’s inspired me to mentor and support others in the industry. And I think DealMAX in particular, just because of the huge scale of the event, has really helped me grow my confidence in reaching out to those women and expanded my perspective on dealmaking.

MMG: And for our last segment, I have a list of questions that we’re asking all of our guests in this series. It’s been really fun to hear everyone’s answers, so I’m looking forward to hearing yours as well. So I’ll take [us] through these; feel free to just answer with whatever comes to mind first. The first question is a is an easy one. When and where was your first DealMAX or Intergrowth, if it was prior to the rebrand?

AG: My first Intergrowth was in Orlando, and I have no idea how many years ago that was, but it was a while ago.

MMG: And then do you have a favorite DealMAX memory?

AG: At a firm-hosted cocktail reception. I was going over to introduce myself to someone who was sitting on a couch, and when I walked over, I realized they were asleep, and it was hilarious, but also so relatable because I think we were all just as exhausted as this person, and they were obviously overcome by their exhaustion, but I think everyone at that reception probably wished they were also taking a nap. So I’ll never forget that. It was very endearing too, for this person.

MMG: I feel like we talk about maximizing efficiency at DealMAX, and that is that embodied. If that’s a power nap during a cocktail reception, that’s probably a great use of one’s time.

AG: Maybe we should bring nap pods to DealMAX, just a suggestion.

MMG: There we go. A new sponsor opportunity.

AG: Exactly.

MMG: What’s one opportunity at DealMAX that you would say is maybe underrated, underutilized, something that people don’t take enough advantage of, in your opinion?

AG: Well, without spoiling the surprise, this year we’re adding some new ways to stay active and engaged while also having productive conversations. So certainly be on the lookout for that. But the speakers that we have are amazing, and I think that, you know, of course we’re all trying to get in our meetings, like I’ve said several times before, but take advantage of the speakers. Those are people that we fight to get to attend this conference and to have the opportunity to listen to them and get their insights and advice is something that is invaluable.

MMG: So I saw that you’re wearing a smartwatch. I don’t know how long you’ve had that and if you’ve been tracking your steps since you’ve been coming to DealMAX in Orlando, but I wonder if you have kind of a best estimate of distance traveled over the course of one of these events. What’s your record?

AG: Well, a few years ago in Vegas, I think my record was 17,800, somewhere around there. And thankfully that year I had brought flip flops to switch into while walking. Otherwise that would’ve been a very painful day.

MMG: I was going to ask you if that was the year that you borrowed the Band-Aids.

AG: No, I learned my lesson the hard way that first year. And I tell everyone, if there’s a new woman in the industry, my first thing that I will tell her is bring flip flops to DealMAX. Because no matter what shoes you wear, even if they’re comfortable flats, they’re still not as comfortable as flip flops. So bring some flip flops, you’re going to get your steps in, don’t bother going to the gym. It’s not needed.

MMG: It’s a great point. I feel like a lot of people’s strategy, including my own, is just to like rotate shoes, but I feel like flip flops problem solved, you don’t even need to rotate.

AG: I mean, men are wearing those, you know, business-y sneakers now. I really would love to see some version of that for women that I could wear with my work attire. I feel like we don’t have any options that are dressy enough, but maybe one day soon. I’m hopeful.

MMG: New business opportunity.

AG: There we go.

MMG: Ashton, what is your favorite thing to do when you’re in Las Vegas?

AG: Well, I’m not a huge Vegas person, so I might venture to say get in my bed and go to sleep, but if Celine Dion or Andrea Bocelli were playing, I would most certainly plan around everything I was doing to be able to go see one of them. So I guess shows. I did see Celine Dion in Vegas a few years ago, which was a great opportunity. So maybe we’ll have someone overlapping with our time there this year.

MMG: Yeah. She doesn’t still have her residency there?

AG: No, I think Carrie Underwood might have a residency, I’m not quite sure, but there’s always somebody interesting, and I feel like I never overlap with them, but maybe this year.

MMG: What is your best travel hack when you’re flying for business?

AG: Oh, great question. And these are definitely female-specific, but I always keep a dedicated travel makeup bag with separate things in it, so I never forget anything. I feel like it’s so important to have one that’s separate because inevitably when I did not, I would always forget one thing, whether it was eyeliner or a makeup brush or something. So definitely a separate makeup bag. And I also pack a monochromatic wardrobe so everything matches and you can save space and wear the same shoes over and over again.

MMG: I like that a lot. And on the makeup bag, yeah, the packing and unpacking and repacking, there’s like too much room for error. That’s a really great suggestion. If you could sit next to anyone in the world on the flight to Las Vegas, who would it be and what would you talk to them about?

AG: Gosh, great question. I would probably say my late grandfather, Pat. He was the ultimate connector and taught me so much about relationship building and dealmaking because he just had so many friends that ultimately also overlapped in business. And he’s been gone for five years, but I would love to have one more opportunity to soak up his advice and encouragement.

MMG: Did he work in the finance sector or was he a business owner?

AG: He worked in every sector. He was an entrepreneur. He bought businesses, sold businesses, he did everything imaginable. And he always had, when he’d have people in his phone, he had a whole sentence to describe who they were. So for me it was like Ashton, horseback rider, active wear, Deloitte Global girl. Like he had all these different words, if you remember people and I don’t have them in the titles of the contacts, but I keep the notes just like he did because it’s so important to remember all the different aspects of who someone is. And we have a lot more to us than our current title at our firms.

MMG: Oh, what a cool person to learn from. He sounds like a really cool guy.

AG: He was, for sure.

MMG: So for my last question: For someone who’s on the fence about attending DealMAX this April, they’re not sure if they’re going to come, if they should sign up or not, what would you tell them to convince them?

AG: You have nothing to lose and everything to gain. So register now while you can get early bird pricing and I mean, DealMAX is where the middle market comes alive. So I think everybody should be there and the more people there, the more opportunity for new connections. You have nothing to lose. Just go ahead and register.

MMG: Great advice. Ashton, thank you so much for your time today and for joining me on the podcast.

AG: Absolutely.

MMG: So before we sign off, just a reminder to listeners to be sure to visit DealMAX.org where you can register for the conference and see the full schedule. Ashton mentioned a really important upcoming milestone, which is January 21. That is the date that early bird pricing ends, so be sure to register before then to save. Thanks again to my guest, Ashton Gillespie, and on behalf of ACG, we hope to see everyone listening to this in Las Vegas in early April.

AG: Thanks, Katie.

This transcript was prepared by a transcription service. This version may not be in its final form and may be updated.

The Middle Market Growth Conversations podcast is produced by the Association for Corporate Growth. To hear more interviews with middle-market influencers, subscribe to the Middle Market Growth Conversations podcast on Apple Podcasts, Spotify and Soundcloud.