Work-Life Balance Wins Big: How Melissa Dickerson Contributed to Genstar Capital’s Massive Growth While Raising Three Kids

Anthony Codispoti : Welcome to another edition of the Inspired Stories podcast, where leaders share their experiences so we can learn from their successes and be inspired by how they’ve overcome adversity. My name is Anthony Codispoti and today’s guest is Melissa Dickerson, Chief Financial Officer and Managing Director of Operations at GenStar Capital. They are a private equity firm based in San Francisco that invests in middle market companies providing both financial resources and deep sector expertise. Their mission is to help organizations in areas like financial services, healthcare, industrials and software achieve transformative growth quickly. With the help of Melissa’s leadership, GenStar has seen an impressive increase in assets under management growing from 300 million to 50 billion. Melissa herself has over two decades of experience in middle market private equity, including 21 years at GenStar. She’s been honored as one of the top female deal makers shaping private equity, thanks to her leadership in operations, finance and team development. Before joining GenStar, she held key roles at American industrial partners and Deloitte, giving her a broad perspective of the industry. Now, before we get into all that good stuff, today’s episode is brought to you by my company, Add Back Benefits Agency, where we offer very specific and unique employee benefits that are both great for your team and fiscally optimized for your bottom line. One recent client was able to add over $900 per employee per year in extra cash flow by implementing one of our innovative programs. Results vary for each company and some organizations may not be eligible.

To find out if your company qualifies, contact us today at addbackbenefits.com. All right, back to our guest today, the CFO of GenStar Capital, Melissa Dickerson. I appreciate you making the time to share your story today. Thanks for having me. So, Melissa, I want to set the stage for how you found yourself in the world of venture capital.

So let’s go back before that. You graduated with an economics degree from Vassar and you took a job with Deloitte, very large well-respected consulting firm. What did you learn there at Deloitte that would later become helpful in your roles in the venture space?

Melissa Dickerson : Yeah, that’s a great question. I think Deloitte is obviously still is a very great brand. They invested a lot of time and energy in training me when I got out of a liberal arts school because I did not major in accounting. So I had to go to night classes and study contract law and accounting and all sorts of other topics to be eligible to sit for my CPA exam. But I have to say the one thing that stuck with me from Deloitte, you know, I was on the audit side and that really has helped me over the years in the role that I’m in now. Understanding how to document an audit trail, how to substantiate your reasoning, your thinking, especially because oftentimes people are asking why did you do a certain thing several years later, maybe six months later, 12 months, 18 months, auditors, IRS, SEC.

And so just to understand and get that training and to understand it’s not a personal thing. Like you’re not telling people they’re doing a bad job, you’re just documenting everything and how you thought about it and why you did things. I guess the new AI is doing a little bit of that if you look at certain, you know, applications of AI, they kind of put together all the backlog of how they concluded a certain outcome. And I think that’s important because oftentimes you want to understand why did you make a certain decision six months ago and here you are today and we’re kind of unpacking, you know, why we are here today.

Anthony Codispoti : Being able to document those thought processes and reasonings as you go along because six months, 12 months, 18 months later, you’re not going to remember everything as

Melissa Dickerson : clearly as you would. And then not putting it in any kind of critical or personal way. It’s you’re not critiquing anyone’s decision making necessarily, you’re just understanding the why.

Anthony Codispoti : So how and why did you find yourself drawn into the VC world then? How did that?

Melissa Dickerson : They were a client, American Industrial Partners was a client of Deloitte’s. It was one of my audit experiences when I was young. I think I leaned more into finance being a child of the 70s and the 80s, you know, going through some of the economic ups and downs as a family.

So I was definitely a middle class kid wanting more financial security in my future and I leaned into financial and financial service clients. And this industry was fascinating at the time. I don’t think it was very well understood or well known. It was definitely lucrative, successful. You had definitely lots of smart people attracted to it at the time. So that was all very interesting to me. And then an opportunity came up with AIP and I took it.

Anthony Codispoti : How did the opportunity with GenStar become a building?

Melissa Dickerson : So that was a few years later. I had worked for AIP for several years. They had undergone a bit of a transformation. So about a year into working at AIP, most of the finance department quit. It was pretty interesting transition.

So that gave me an opportunity to really step up from being more of a junior accountant to a CFO or a leader of the finance department at the time. But at that time at AIP, they had a couple partners who were a little bit older. I was pretty young.

I was 26 and I think they were in their 60s. And so I just thought, okay, if I want to do this long run, I’m going to probably want to partner with investors that have a little bit more runway. Because you could see that these folks, these leaders at the time, I think it’s since transitioned.

So there’s new leaders now. But at the time when I was there, I just, you know, they were, I think, focused more on moving on. And so I took my time. I looked around and it was just through a recruiter.

I found GenStar. And at the time again, had younger partners. It was just beginning its investment track record. So it just felt like a good opportunity.

They were very transparent. And I wanted that too. It makes my job a whole lot easier if we can be transparent with investors. So just having that approach to communication, I think was one of the big decision makers for me.

Anthony Codispoti : What was going on at AIP that so many people quit? Was it because there was this sense that the leadership wanted to move on?

Melissa Dickerson : I just think it was like, I think there was one woman who had an illness and another who wanted a little bit less of an intense role. So it wasn’t a big department by any stretch of the imagination. I don’t want to imply that like the whole firm quit. But it just was a small firm and those folks moved on. And it just opened up the door for me to step in and kind of take on more leadership that it was unexpected at the time for me.

Anthony Codispoti : So let’s talk about what the investment thesis is like at GenStar. What kind of companies are you guys looking for?

Melissa Dickerson : Yeah, you said it in the intro. We have a particular domain interest in industrials, healthcare, software, financial services. We always like to bring capital situations that need change. We like to partner with them. We’re fairly entrepreneurial, so we like management teams that can manage their assets.

We’re not prescriptive. We like strong leaders. So we try and partner with strong leaders, bring capital at moments of change in the life cycle of companies. We also have a wonderful group of strategic advisory board partners. Those are former CEOs, leaders in industry that have been in industry for 20, 30 years that can help diligence companies or sit on boards of companies, be coaches to CEOs and CFOs. So we bring that expertise to the table too. And I think it all makes a big difference. So that’s generally how we approach investment.

Anthony Codispoti : And I’m going to guess you sort of following the typical life cycle, you’re looking for kind of a five to seven year kind of exit on your investments?

Melissa Dickerson : Yeah, yeah. I mean, I think over time I’ve noticed patterns where in certain markets you can exit maybe really more quickly than you ever thought if it’s 18 months or two years. And then certainly as you see like the Great Recession, you see a bit of a slowdown.

It’s organic. And so over time, again, I’ve been in GenStar going on 21 years, and in private equity almost 26 years. So you just, you’re reflecting the market, right? I think over that time, I think it’s something like it used to be 2000 private equity back companies in the year 2000, something like that. And now it’s over 12,000. So it’s grown quite a bit. I mean, relative to the market cap of public, it’s still about 10% of market cap for public companies. So overall value, but it’s a huge amount of companies that are private equity backed today relative to 20 years ago. So I think we’re just trying to manage our assets through the cycles, be as patient of capital as we can. Our investors are signing up for the long run. That’s the nature of private equity. We’re not looking for the next quarter’s returns. We’re looking for that longer on five, seven year profile.

Anthony Codispoti : And why do you think that there’s been such a big increase in companies that are backed by private equity funding?

Melissa Dickerson : Well, I think, I mean, I’m not going to pretend to be an expert, but I think a couple of the reasons are certainly the regulatory environment is challenging if you want to go public.

You need to be of a certain size. So some companies might want to avoid that climate for a time or support their growth in the meantime. I also think you need a lot of capital. I mean, the whole point of going public is to get a lot of capital, hopefully, for again, some sort of investment of that capital back into the business. And I think with the advances we’ve seen in technology over the last 20 years, you can do quite a bit more with less. Like so you don’t need as much capital to see meaningful changes in companies. You can do quite a bit with technology.

So I’m interested to see actually, as we move into the future with AI, that mix. Are we seeing more public companies? Are we seeing more private equity backed companies? I’m not sure what the answer is, but I’m curious to see what the future holds.

Anthony Codispoti : Do you have visibility into your portfolio companies to see if, you know, with the popularity of AI in the last couple of years, are you seeing them able, being able to do more with less, as you said, now, today?

Melissa Dickerson : Again, my role is generally back office focused. So I’m not going to be an expert on all the different nuances of our portfolio investments. We have investment professionals who sit on the boards and manage the assets and have the thesis about the investment, particularly in the industries. Certainly, I think we’ve all been paying attention to AI and I think we all want to run businesses efficiently. I think that’s just how we approach investment and day to day operations. So I mean, again, I don’t know if I’ve necessarily created particular metrics to measure our people being more efficient two years ago versus today.

I just I’m curious to see how we all implement AI and how much more efficient it makes us. I just think there’s quite a bit of potential with that. Yeah.

Anthony Codispoti : Melissa, what are some of the other trends or big changes that you’ve noticed in the 27 years that you’ve been in this space?

Melissa Dickerson : Yeah, I think again, I mean, certainly, the size of private equity has grown significantly. So when I started, it was unknown. It was small. I think we talked about we closed a 500 million funds. These days, there’s so much interest in alternatives. You know, we just closed a 12 billion fund. People are looking to alternatives as an investment space because it yields pretty meaningful returns relative to alternatives, if it’s public markets or other types of investments. So certainly that just growth and interest as an investment class has happened. The growth of the companies that are private equity backed over time has been another big change. I’d say the approach to investing has evolved. So I think in the beginning, it was financial engineering.

You really just did the LBO model and put debt on a company and hopefully paid down the debt and exited. Whereas today, I think people want to bring operational change, partner with folks in industry to change if it’s top line, if it’s bottom line, if it’s approach to sales, investing back in the companies. I think there’s quite a bit more that’s done with portfolio companies than ever before.

More coaching, more oversight discipline. I think we’ve seen certainly that approach to investing change over time. I think that we’ve also seen, again, back when it was smaller, you had an investment professional wear a bunch of different hats.

If it was financing the company, sitting on the board of the company, understanding the CEO and the CFO, maybe searching for new candidates for those roles if you needed to. Whereas today, you have a dedicated capital markets person, a talent management person, and maybe a deal sourcing person. So there’s definitely been more of a- People are more specialized.

Yeah, which is almost intuitive. I think if you think about starting up a company, you initially wear all the hats and then as you grow bigger and bigger, you become a little bit more particular and specialized and disciplined. If you bring in experts, you can make those sections of your business more productive. So those are just a few of the changes I’ve seen over time. It’s been interesting and I’m curious about what the future holds. It’ll be fun.

Anthony Codispoti : And you’ve been at GenStar for 21 years. Clearly, you must really enjoy working there. How would you characterize the team that you work with?

Melissa Dickerson : Oh, yeah. I love GenStar. I love the team. As I said in the beginning, I think I was really attracted to it because we were very transparent with investors. We partnered with investors and I think that’s still true today. We call them a lot if we have questions. We report to them at anything we- any kind of question we have, we go back to our investors.

We’re kind of keeping them top of minds. Is that unusual? I don’t know. Again, I’ve been 21 years with the same firm. I think I know other firms again have more dedicated investor relations people and we do have some of that at GenStar too. But I do think we like to have those relationships, those connections with specific people more one-on-one directly without intermediaries. So I know that’s something that we value.

I do think again, I’m really lucky to have a group of partners right now that are my age. We kind of came up in the organization together. They transitioned into leadership. So we’ve been able to kind of go through the same phases in life together, which has been great.

You know, having kids, getting married or getting married, having kids and then sending them to elementary school and high school. I think that’s been great. I mean, again, I can’t underestimate or undersell the talent. I do think our investment professionals are very talented investors. They’re really knowledgeable about their industries, they’re really good relationship builders because I do think there’s a moment initially when you’re an investor, you come out of like an investment bank, you kind of are the Excel jockey and the spreadsheet can do all the modeling. But there is a moment where this becomes more of a relationship building business where you have to connect with your management team, connect with your board and just those are very powerful things. It’s a sales role in a sense.

You have to want, people need to want to work with you. If all things being equal and you’re looking at two private equity funds, you want to hopefully differentiate yourself on the front of we’re going to be good partners for management. So I just think we have a really talented group of people that are really good at building relationships. Not only that, but also obviously picking good platforms and industries that have a lot of potential for growth in the future.

Anthony Codispoti : There might be some people listening who are interested in pursuing a career in this industry. As you look at sort of the folks that you work with, is there sort of a common thread or a track where most people tend to start out with this college degree and then they work at this place and there’s sort of these blocks that they stack up that put them in a good position to enter the private equity space.

Melissa Dickerson : I think the traditional approach has been, you know, you go to a good college, probably major in something like finance, accounting. There’s certainly other majors too. You probably do some time at an investment bank, a big one, JPMorgan, Evercore, Bank of America in a particular domain and then consider an associate, which is a two-year rotation at a private equity firm at that level.

Then consider going back to business school or getting more operating experience and then coming back as an investor. That’s generally the track that we see. I mean, there’s always exceptions. This is another domain where we’ve seen change over the last 20 years where it was pretty rigid historically and I think it’s become less so. So going back to get your business degree isn’t always a requirement anymore.

You can go, for example, maybe to a portfolio company and work in operations there and then maybe come back. I think that gives that candidate some great opportunity to again understand what it’s like to be on the operating side, to be in the boardroom. It really gives them a great perspective that they can bring as an investor. They can bond a little bit more quickly with management teams because they had a role in the management team. The alternative to that is maybe going to business school and that also brings great experience. You oftentimes are graduating with people who also go into investment so you know peers in different operations and firms and can understand how they might approach investing, what they’re doing, where they’re investing. So that’s a network that you can leverage over time. So both alternatives have a great outcome. It’s just they’re different and that’s changed I think over time. It used to be just you’d have to go to business school but now I think you can do either route.

Anthony Codispoti : Multiple paths. You mentioned going kind of through similar phases of life with a lot of your team members. Getting married, having kids, kids in grade school, kids in high school. How do you find that work-life balance working for you with kids and you know a very demanding career?

Melissa Dickerson : Yeah, no it’s definitely been a journey. I have three kids. They’re all teenagers now so I’ve got a junior, a sophomore, and a seventh grader who’s a teenager though so we’ll call it that.

Two boys and a girl. I think when they were smaller it was more of a physical game and so you needed to just take care of yourself. Make sure you were sleeping with the kids and leveraging other people.

I mean it’s never a one-man job. It’s you and your husband and then your extended family or we had a no-pair live with us which was fantastic. We’re still in touch with her and so I also again because we all kind of came up together I think there was a lot of understanding that if you needed to miss a money-morning meeting because you had the first day of kindergarten that that was the right choice.

I think all of us have the same values. We value family and so to put your family first in certain circumstances if you’re having a baby expecting a baby take time off. Enjoy that moment in life. I wouldn’t say it’s been easy because it’s been a challenge but it’s very much worth it on both fronts. I feel obviously my investment in my kids is paying back dividends but my investment in my work is also paid back dividends and I can see my future where the kids maybe are grown and I’m doing more on the work front and I don’t know I feel like keeping a foot in both worlds has been really important to me. I had a mom who worked when I was young she was an RN and so that was the model I had.

I never contemplated not working because I always again came from I wouldn’t say it was precarious financially but it wasn’t 100% easy. She had four daughters so that was a big family. My mom and dad had four daughters so just to make sure that you had an ability to take care of yourself and have a job was important the security of that and then to have the time to devote to your family. And so that’s I think one of the reasons I was attracted to my role as the CFO and managing operations is that I didn’t have to travel a ton like the investment professionals do and I had a little bit more control over my calendar. So that enabled me to be both successful and invest time in work and invest time in family and that’s been a big and very important balance for me.

Anthony Codispoti : Have you ever found it difficult to explain to your kids especially when they’re younger? Mom can’t be there for this thing like there were times maybe where you couldn’t show up for the event that they wanted you at?

Melissa Dickerson : I don’t know. I haven’t really struggled with that. There have definitely been times when I haven’t been like today will be a time we’ve got our investor meeting and I’ve got to go to that and my son has a recital. I think we’re there enough so that they don’t feel like we’re not we’re not there enough. That might change when they’re 35 and in therapy and saying mom you were never something but I don’t get the sense that they are feeling neglected. I suppose I make a big effort to try and connect with each of my kids as a human being and as a person and really see them for who they are and try and meet them there so that they know I see them and I’m paying attention and it might always might not be that I’m showing up for a soccer game.

It might simply be just you know checking in at the end of the day and saying you know how is your friend doing you were talking about or how are you feeling about the math test for tomorrow but just making sure I’m staying current in their lives and understanding what they’re going through and respecting them and their decisions and and trying to facilitate and help them in their choices. I’m in the teenage zone now so it’s a little different game than when they were small. It’s more you know guiding versus directing I suppose when you’re when they’re small.

Anthony Codispoti : I selfishly asked that question because I was dealing this this with my eight-year-old son the other day where he forgot to tell us until yesterday two days ago that he had a speaking part in upcoming school mass and you know could we be there and I looked at my calendar and I’m you know booked solid during that time and it you know I was able to change my schedule the last time something like this came up and he was very happy that I could be there and he couldn’t understand why I couldn’t make that happen again and it was just sobbing just tears coming out so I thought maybe you would have a little golden nugget there for me that you could pull on from your experience so I could put into

Melissa Dickerson : play yeah sorry I’m not yeah

Anthony Codispoti : that’s all right I’m not having a nugget. Let’s see you guys have grown quite a bit in the 21 years that you’ve been there. When you first got there roughly 300 million in assets under management now 21 years later you’re at 50 billion with the B what what do you think are some of the biggest levers that you guys have pulled over there at GenStar that have allowed for this kind of growth?

Melissa Dickerson : Right so I think one of the biggest ones is outsourcing so I know and it was not my idea I’m going to give credit to Tony Sileski is one of our partners he was interested in the domain more for an investment idea but you know we tried it on and I think it was the right choice especially facing the growth that was coming so partnering with a good outsourcer right now we partner with Apex Fund Services they help us with all of our fund administration our ESG portfolio company data collection producing everything that we need for financial reporting they’re they’re global so and then certainly have a great perspective and this is true of a lot of outsourcers right that work in the space is they work with a multitude of different general partners investors different types of asset managers so can tell you here’s generally what we’re seeing people do on this question on that question can give you that perspective so that you can hopefully conform or make good choices relative to peers certainly have access to great software solutions and probably get more responsive support because they have a big footprint with those software providers so outsourcing has been I think one of the main elements of leverage we’ve used to grow the back office for sure

Anthony Codispoti : so when you say the outsourcing you are talking specifically about the back office and not so much sort of pushing the outsourcing model on your portfolio

Melissa Dickerson : that’s right no so I’m specifically talking about the back office because if you think about it we want to have the investment teams focus on what they want to focus on what they do best which is investment and connecting with those CEOs and you know being in the room there for board meetings and so we don’t want to build a huge back office that someone needs to take a decent chunk of their day out of managing and in addition to me it would probably be some sort of president or CEO so outsourcing has allowed us to partner with the front office in a way that gives them the free time to just focus on investing and being good investors so again it’s been just a wonderful way for us to obtain leverage over over the years one of the biggest ways

Anthony Codispoti : when did you start to embrace that

Melissa Dickerson : probably around 2016 2017 so that was about the time we partnered with apex we already partnered with an outsourced law firm that does a lot of our our legal work and a big accounting firm to do taxes that’s been kind of the case since I started but really partnered with a fund administrator in that 2017 timeframe and that I think since then we’ve grown in AUM pretty materially meaningfully

Anthony Codispoti : was there something I don’t know uh it’s sort of the broader macro environment that sort of nudged you in that direction or was it just sort of like hey we’re seeing some other folks do this this seems like a good idea

Melissa Dickerson : let’s go more down this I would say in my experience that investors again after probably the great recession I think you saw investors do quite a bit more diligence on the back office that’s probably for a number of reasons both macro and micro and so what it’s called operational due diligence. The investors will come in and they’ll grill me. They’ll want to understand how we do everything on the back end to assess risk management. And I think the feedback we got as we grew in AUM, especially as we kind of raised that first billion dollar fund, was that generally with the AUM size this big, we’d expect you to partner with a fund administrator.

There is an inflection point. I think when you’re a smaller, like if you’re raising a couple hundred million and you’re starting out as a private equity partner, you can probably figure that out. I’d still encourage you to outsource because I think that’s a great way to just get everything off the shelf.

But if you did and it’s not the end of the world, and I think people would still support you. But I think as you grow in AUM, investors want to see that partnership with a fund administrator because they want to manage their risk. And I think a fund administrator gives them a nice, clean way to do that. Fund administrators generally.

Anthony Codispoti : Is it because it’s sort of like almost like a neutral third party that’s sort of keeping an eye on things as well? Is that part of the reason why investors want to see that? It’s

Melissa Dickerson : absolutely that. It’s generally the fund administrators, again, have good software. They typically do that. It’s called a SOC report statement. I think it’s of controls. A big accounting firm will come in and assess their internal controls. So again, it gives some comfort to investors that, OK, they’re partnering with a firm that understands accounting, that it’s using the right tools that’s getting itself a third party to check it on controls. So again, it just gives them that much more comfort that something isn’t going to go sideways.

Anthony Codispoti : Now, that makes sense. You’ve been recognized among top female dealmakers. I’m curious if there’s any specific ways that you’ve been able to mentor or guide other women aspiring to leadership roles, whether it be in the funding space or finance and operations and other industries?

Melissa Dickerson : I mean, I think for women or men, I just think of my kids. And I think of people that I’ve helped over the years. I’m always open to helping. And so certainly over the years, I’ve had people ask about this or that, if it’s or wanting, for example, a reference, leveraging my network to get them introductions if they want a job opportunity.

I’ve done all sorts of things. Spoken at my kids’ high school, spoken at my alma mater for business school, had folks come and ask about it. I think you originally asked the question of what is the profile of how do you get into private equity, given them coaching on that front. I’d also, again, now that we’re talking about it, just highlight to anyone who’s interested in private equity is to consider roles in portfolio companies that are private equity backed, because I do think those are great opportunities, much more frequent, much more. There’s just many more of them. And those would be great ways to get introduced to private equity working with private equity.

Anthony Codispoti : Plus, you’re getting that perspective from inside so that if you do flip around and now you’re part of the investment fund that you understand what’s being asked.

Melissa Dickerson : Yeah, those positions are going to be lucrative. Hopefully, they’ll be a combination of salary and equity. And then lots of different skill sets apply. You could be good at just sales and become a salesperson at a portfolio company that’s backed by PE.

You could be an accountant. There’s just lots of different profiles there. So there’s just so much more opportunity on the portfolio company side that I think people should take advantage of. But yeah, mentoring, I think, is, for me, it’s been just being open to if anyone needs help, that I’m willing to invest time.

Just the other day, somebody was saying to me, they’d love me to look at XYZ that they want to propose as a product for private equity. And I’m happy to give them my two cents. And if I can be helpful or if I can think of another introduction that might be helpful for their endeavor, I’m happy to make those introductions. So it’s just having that generosity, I suppose, to others. That’s been my strategy around mentoring.

Anthony Codispoti : Is that something you learned from one of your parents? Is it just sort of innate in you? Was there a mentor early on that kind of said, hey, embrace life in this way?

Melissa Dickerson : Yeah, I think my father was very generous. And we learned that pretty quickly. He was always the guy who’s going to give a giant tip to the waitress or help out a friend move. So we definitely had it in the family to be generous, to be overly generous. And I think that’s something I’m teaching my kids too. I think it’s important. It’s being part of a community. It’s understanding that you’re, certainly, your family’s important, but you’re part of a bigger community. And so having that generosity of spirit and having an ability to give back, I think, is important.

Anthony Codispoti : How do you teach that to your kids? So I think it’s an amazing, wonderful trait to be able to try to instill in ourselves and then teach to our kids as well. You have any suggestions for the rest of us?

Melissa Dickerson : I think the most powerful thing you can do as a parent is model. Right? It’s the choices that you make. It’s the way you’re carrying yourself day to day and all the big and little things. Certainly, at least with the teenagers now, we’ll do charitable work and bring them with me. Kicking and screaming sometimes, but they get there.

So I think both Rodger and I, I think have made an effort on that front. I know the boys just went to Cuba for a baseball holiday. And the idea there was more of a charitable endeavor.

You’re bringing baseball equipment to a country that needs that and they enjoyed themselves and on the baseball front and then got to feel good about providing for others. So I mean, those are just, those are the examples.

Anthony Codispoti : That’s one thing I can’t keep track of it. You know, are we allowed in Cuba or are we not?

Melissa Dickerson : I know, I can’t either. We’re allowed in Cuba now. This was a spring break. I’m sure it’s changing. I don’t, yeah, I don’t know.

Anthony Codispoti : Yeah. But at the time, they were allowed to go. It was a great experience and something that they got to put into practice from what you and your husband had been teaching them.

Melissa Dickerson : And I mean, the idea came from, again, just the larger community. We have a connection to someone who’s from Cuba, who had family there. And that’s kind of how we made all of it happen. My husband was in charge of all of it. So that was a great example. And he brought the boys, which was nice.

Anthony Codispoti : You know, speaking of being generous and, you know, helping folks, I understand that you put on a CFO summit. Can you tell me more about that? Sure.

Melissa Dickerson : We’re having one here in the fall. We gather all of our CFOs at our portfolio companies together. We try and keep it small. I think the idea for me was way back when I started in private equity, I reached out to pretty much cold emails to a couple other CFOs that sat in my seat. And I think we all found it pretty invaluable that we had these connections. So we would, at that time, just have occasional lunches together.

And then it got bigger and bigger. You know, so it’s at this point, you know, I know, across the country, lots of other CFOs, but that that was so useful. You know, you could call particular people up, ask a specific question. You had a problem.

You wanted to use a new software. You could get some perspective. And so that was the origin story of why I wanted to do something similar for our CFOs, saying, OK, all of you are in similar positions, maybe different industries, maybe different sized companies, but have definitely things in common, being private equity backed and giving them an opportunity to meet each other, to network with each other, hopefully to get to know and feel comfortable with each other so that if they do have a question, they can pick up the phone and call each other and get some good coaching because you learn quite a bit from other people, right?

That’s like one of the biggest ways you learn is from other people. And so the opportunity also was was kind of it came out of when we partnered with one of our former CFOs, Gary Michael. He’s a strategic advisory board member now for us.

So he had a great perspective because he had walked a mile in that role. He was a CFO of a successful platform, exited, had also had a pretty deep career as a CFO with other types of companies prior to working with GenStar. So just between Gary and myself, we can plan a couple days for the CFOs that hopefully is a productive and helpful one. So it’s a little networking, but then it’s also talking about particular things if they have questions.

I think we’ll probably focus a little on AI this time. How are we using it? What are the use cases? What are particular maybe consultants or partners that you can consider using? But those are it’s just a great way we found to connect the CFOs together. And hopefully it’s a good tool for them to learn and bring it back to their platforms.

Anthony Codispoti : You know, I get to talk with a number of CFOs, whether through my other line of work or that I interview here on the podcast. And one of the things that I hear again and again is, and I really want to learn how to better leverage AI. Like I’m just sort of dipping my toe in the water and they’ve been having trouble finding the expertise or the person to sort of train them to kind of take what they’re doing at this level and move it on up. So yeah, I hear you talk about being able to put on a session like that for your poor CFOs and I’m like, oh, I think they’re going to be pretty excited to see that.

Melissa Dickerson : Well, and that’s learning, right? I just, I guess that’s the other thing I with my kids. I, you know, because they’ll come in and they’ll complain and this is too hard.

But I mean, that is learning, right? When you’re in the deep end, you drop yourself in, you feel a little overwhelmed. You don’t know if you can figure this out. You just kind of keep looking around, figuring it. You just keep keep on keeping on. You just keep tackling it. And then you eventually kind of get through that and go, oh, now I understand this particular question, this subject, this use case. You know, you just have to keep at it and learn.

Anthony Codispoti : Yeah, I think the other great thing about what you’re doing is that peer support. You know, when you’re the CEO or the CFO, you know, you are the top person in that department at your company. And sometimes you can feel like you’re a little bit alone, like you’re on an island, like everybody looks to you for the answers. You know, where can you go when, you know, you need a bit of advice or a sounding board? And, you know, with, you know, GenStar, you’ve kind of got that baked in, especially, you know, with the extra effort that you’re going to put on these summits where everybody can come together and they can meet each other.

They can exchange notes. You’ve got that networking so that, you know, three months down the road, it’s like, you know, you hit this roadblock. You’re like, I’ve never seen this before. What do I do? You know what? I’m going to call Sally that I met at that conference. I bet she’s done this.

Melissa Dickerson : And that’s, that’s another change I think I’ve seen over the years too, is that when we started, it was pre-internet, you really did feel isolated. You felt like you were the only firm doing this, that or the other.

You were the only person trying to solve this problem. And then the internet age happened. And I think we all discovered that, wow, there’s so much we have in common with each other. So many of us are trying to solve the same problems and then having the ability to research it and come to kind of some conclusions that are pretty common, I think is powerful over the years for sure.

Anthony Codispoti : Melissa, what’s your superpower?

Melissa Dickerson : I think all of that, well, I think what you see is what you get. I am, I’m a very calm person. I suppose it’s my mother who is an RN and, you know, she lived through some emergencies, but she kind of taught us that having a cool head in stressful times is the only way to to get through it. So I do think that I’ve lived through lots of things, you know, the Great Recession 9-11, all the different big macro challenges to the markets over the last 20 plus years and kept a cool head through all of it and understood that, you know, that’s the only way to succeed in times of stress is to, to keep your eye on the finish line, to keep your eye on the ball, to triage, you know, to get through it. But there is another side, you know, you will get to the other side. So I do think that’s one of my superpowers. And then honestly, it’s love of learning and curiosity.

Just over the years, we’ve evolved and changed so much. I didn’t need to change jobs to get that. I got that just staying at the same job. But I really needed to be open and comfortable with change, comfortable with trying new things on, iterating. And that’s just my love of learning.

Anthony Codispoti : So we’re recording this episode late May of 2025. I’m curious to hear if current economic political conditions remind you of any other periods of time that you’ve been through, whether from a positive perspective or this is something we’re concerned about?

Melissa Dickerson : I think honestly, I am not experiencing a ton of angst. I think, again, we’ve lived through the Great Recession. Certainly the registration with the SEC for the private equity industry was a big change.

I would say the focus of the SEC, it depends on the administration, but we’ve always had somewhat of a lens put on alternatives and privates because of the growth, I think, and people wanting to understand that market. So I’ve been pretty comfortable because I guess I’ve been living that life now for a while. Being ready to, again, that audit background, just if someone comes in the door, I can answer questions. If some risk is out there, I can assess it.

I’m not going to get worked up about it because, again, people generally come in with a certain theory in mind and I just need to understand what that is and sit down and we can talk, we can go through the facts and the data and either agree or disagree. But I think, again, I feel very lucky that I have got really talented investors and really wonderful good people that I work with that make good choices. So yeah, it helps quite a bit. So yeah, I wouldn’t say that. I mean, you keep your eye on the news. So for me, it’s more of like making sure I don’t go overboard. But but yeah, I’m not I’m not massively stressed this this time versus just, you know, a year ago.

Anthony Codispoti : Do you feel like you’re just sort of a naturally calm person? Like that’s sort of how you’re wired? OK, I was going to ask if there’s anything you do like meditation or exercise or particular dietary choices that sort of help.

Melissa Dickerson : Oh, yeah, I love running. I love weightlifting. I’m definitely a movement person to manage stress and frankly, just for fun. But I also do default to calm. And and, you know, again, I would say also this is going to be funny, but I have teenagers, right?

So I’ve been living a little bit on the edge, you know, for years now. So the macro, whatever is not throwing me at all, because my my teenage son does better at that. You know, if it’s he’s made a bad choice and now I’m going into the school to figure out. So I don’t know. I am. Yeah, but I do think

Anthony Codispoti : that’s that’s built up a little bit.

Melissa Dickerson : Yeah, for sure. Yeah. Yeah.

Anthony Codispoti : That’s that’s kind of on that path. Anyways, curious to hear about maybe a serious challenge, Melissa, that you’ve gone through, whether it’s personal or professional. Was that like, how do you get through it? What do you learn?

Melissa Dickerson : Yeah, I think we talked a little bit about this in the lead up, but I want to both of my sons have ADHD. And it was for my oldest diagnosed right before COVID. And that was a challenge. And I mean, again, I want to be sensitive to his situation because it’s his story too. But it was it was a challenge for me to understand it, because I am the opposite. I’m I can be very organized and focused and think five years out. And the ADHD temperament is I only want to focus on what I want to focus on. I’m not interested in other things. I’m interested in this thing. And so it’s a it’s a different approach.

He’s a very smart person, but it’s tough for a kid with ADHD to go into a traditional educational environment and succeed, because that requires a level of like focus and discipline and organization that I’m not sure that profile is inclined to. In fact, it’s kind of the opposite. They just again want to focus on if it’s math or history, let everything else go. So that’s been a challenge for me to understand where he’s coming from and how he’s going to do what he’s doing and how best I can help him and support him. It’s been a challenge navigating the public school systems. I know we had to hire a lawyer to get him on an IEP.

It was struggle, which was difficult. I have a fantastic lawyer. She’s wonderful.

It was hysterical. The first time I called her, I was practically in tears because he was struggling in school and I didn’t know how to help him. And I felt like I had done all the things, but I wasn’t having success. And she was just wonderful because she came and said, you’re doing all the right things. And, you know, she is still a great help to us day to day with just that perspective on the temperament, the profile. I do think and hope in the future that the public schools will acknowledge this type of approach to thinking and learning and kind of meet the moment with a teaching style that’s a little bit more attuned to that. I don’t, there’s a ton of great teachers in his high school. And then there are some that probably need a little bit more education on the temperament and the profile. And then, you know, to be fair to them, you know, he’s an independent guy.

And so it was this combo of like how he approaches things and him being pretty fiercely independent. But that definitely just because your kids are obviously your most treasured asset or however you want to say it in life. And it’s tough to see them suffer. And you definitely want to see them succeed.

And you obviously worry about them pretty much your whole life. But, you know, navigating that has been a challenge. And I don’t know, it’s, it’s, we’re on it. We’re in a good spot now. And I think he’s, he’s teaching me a little bit more to lean back and let him do his thing. And he’s, he’s figured himself out, which is what you want to see as a mom of a teenager. But it’s, it was a journey. It was a struggle.

Anthony Codispoti : You know, I’ve got a young son who we identified pretty early on that he needed some help with speech, with comprehension. We got him some services there. My wife is actually a speech therapist. So that certainly helped in kind of being able to notice that early on. There were some questions about, you know, as we’re getting in those services, like would he qualify for an autism diagnosis? And that smacked her across the head in a way that’s sort of hard for me to put words to.

Ultimately, he does not. But at the time, like there was, there’s sort of already this sense of, did we do something wrong? You know, like, is this on us?

Should we have made a different choice here or there? And then, you know, when that came in a little bit later on, like, oh, you know, maybe we should get him looked at for autism. She had a really hard time because it was like, this is her area of expertise.

And she had not spotted that. And she, you know, put even extra guilt, pressure, shame, whatever negative emotion you want to sort of attach with that. I’m curious if you kind of went through any of those emotions of like pointing the finger back at yourself and like blaming or wondering, like, I don’t know, this is somehow.

Melissa Dickerson : Oh, of course. Yeah. You wonder even, even like, honestly, did I eat the wrong things in pregnancy? Did I do the wrong nurturing when he was tiny? You know, just you can really go down a rabbit hole with all of those things. And I was saying, I read a book one time that talked about, I think parenting as either being constructing, you know, houses, being a builder or being a gardener. And I think the idea was there was that, you know, you have a ton of control over, like, building a house. And as a gardener, you kind of have a little bit of control because you can weed and water, but it’s really organic and whatever happens in your garden happens. And it’s beautiful at the end of the day, but it isn’t necessarily something like building a house. And so I do think as we go through that with parenting, we kind of always want to lean into, it’s a house, but I think it’s more like a garden and that you’re just doing what you can.

The watering, the sunshine, the feeding, but you’re going to get what you’re going to get. And it’s not, not everything is in your control. It’s not everything is your fault. And sometimes that’s not even a useful frame of mind or approach. So it’s, yeah, I mean, you have to, it’s those are day to day conversations you have with yourself.

Can I, even just the other day, I want to say, Charlie was telling me, you know, why are you so concerned about? This is my life and he’s right. It’s like, that’s not your choice. I’m confused why you’re thinking it’s somehow your thing. And when it’s not your thing, it’s my thing. And again, he’s right, but it’s apparent.

Anthony Codispoti : But I think when, yeah, when you’re, you’ve been so successful in your career path and you’re very good at what you do, you tend to put things. Tell me if this applies to you. This is how sort of my brain works. It’s like, oh, I’m very good at this. I’m very successful at this. I can pull these levers. I can generally make a lot of these things kind of move in the direction that I want. And why can’t I do that with my kid? Like I should be able to have the same level, you know, right, I should be able to put the fertilizer in the water and the sunshine. And I should get out what I’m expecting and what, you know, the output should somehow equate to my input. And boy, sometimes that is.

Melissa Dickerson : I always joke that kids are like employees, you can’t fire, right? So like you have to figure this out. Because at work, you can, you can manage people. And then you either accept sometimes limitations or maybe you solve for a different person.

But that’s not what you’ve got going on at home because you can’t exactly, you’ve got to work with the kids and, and you’re, you know, you’re not in control of everything. And that’s okay. And they teach you a lot. And that’s one of the big lessons, right?

Is that they are their own people. And they’re going to be different than you. And, and they’re going to teach you things. These days, my kids teach me so much. It’s amazing from the small things to the big things.

Anthony Codispoti : What’s a big thing they’ve taught you recently?

Melissa Dickerson : I think this, this conversation I had with my oldest around where I end and he begins because I think for a long time I’ve been his partner in school. And especially with the ADHD profile, you think, okay, I’ve got to be his executive function. I’ve got to think ahead. I’ve got to, and, and I have to let go a little because I’m not going to college with him. You know, so I have to let him fail a little. I have to back off a little. He’s got to choose to do this. And it’s hard, right?

Because as a parent, again, from the get go, you’re involved, you’re there, you’re doing the watering and the weeding and. It’s really hard to just stop, but you have to. And I think that’s definitely the memo that I got earlier, which is good. I raised a kid who’s going to talk to me like that, which is also good. So yeah, that that’s, that was

Anthony Codispoti : probably a memo that they’ve been trying to get you to read for sure. And now it’s finally starting to sink in for a little bit. Yeah. How about a favorite book or a podcast, maybe a course that been super helpful or instructive for you, whether it’s on the personal or the professional side?

Melissa Dickerson : Yeah, yeah, a couple come to mind there. I love Phil Tetlock’s book, Super Forecasting. And Annie Duke is another one. She wrote How to Decide. She’s a poker player. And both are very similar in that if you think about investing, it’s a lot about predicting the future. And making decisions. And I think what both books tend to focus on is a little bit figuring out what is knowable and what is not and figuring out how to think in a disciplined way, in an informed way. You want to again do your diligence, figure out some knowns, create some bookends over a question.

Be real. You know, you’re not going to be able to predict 12 years from now who’s going to be the president of the United States, but you could probably make some reasonable guesses in the next, you know, three weeks, three months or so. Both of those books, I think, speak to that type of decision making. And I think it’s very helpful to think about it, to read about it, to get some of that education. Because I think a lot of folks maybe think they either they I was guilty of this. Like you just want to get to an answer. So maybe you skip over some diligence and then you learn, oh no, if I’d just asked or gotten a little bit more educated. I would have figured out some of these problems and gone a different direction. So I think that’s super helpful, both personally and professionally.

Anthony Codispoti : And these books kind of give you some guidance on how you might do some of the additional diligence or think about approaching it.

Melissa Dickerson : So if you want to, I mean, Annie Duke’s book is a little bit an easier read. It’s well done. And it’s, it’s she again was a poker player. So you can imagine is very poker examples. But that is decision making and informed decision making. And then Phil Tetlock’s book did experiments with cohorts of people.

So it’s very fascinating. That was super forecasting. So I’d recommend both books to folks who want to learn more about decision making and have some some clarity around some of some good best practices.

Anthony Codispoti : Melissa, I’ve just got one more question for you. But before I ask it, I want to do two things first. First of all, I’m going to invite everyone listening to go ahead and hit the follow button on your favorite podcast app. We’ve had a great interview today with Melissa Dickerson of GenStar Capital. You want to get more great content like this. I also want to let people know the best way to either get in touch with you or follow your story. Melissa, what would that be?

Melissa Dickerson : Oh, you know, GenStar has a website, GenCap, G-E-N-C-A-P dot com. And that’s probably the best place to see any news or announcements about our firm.

Anthony Codispoti : GenCap.com will include that link in the show notes. So last question I have for you, Melissa, let’s say you and I reconnect a year from now and you’re celebrating one thing. What’s that one thing?

Melissa Dickerson : I’ve got two graduations. So I’ve got an eighth grader next year and I’ve got a senior in high school next year. So we’re hopefully celebrating graduation this time next year.

Anthony Codispoti : Are we looking at colleges?

Melissa Dickerson : We are definitely looking at colleges. Yes. So we’ll see where we land with that too, which is going to be a journey. But I’m excited.

Anthony Codispoti : Is it a local net that you’re casting? Regional nets?

Melissa Dickerson : He’s going across the US. We’ll see where he lands. But I’m excited to actually see what the next chapter holds.

Anthony Codispoti : No. Melissa, I want to be the first one to thank you for sharing both your time and your story with us today.

Melissa Dickerson : I really appreciate it. Thanks for having me. This was fun.

Anthony Codispoti : Folks, that’s a wrap on another episode of the Inspired Stories Podcast. Thanks for learning with us today.