Financial management can make or break a business. Any business undertaking attempted without taking cost drivers, growth prospects, and value realization goals, among other critical factors, into account is leaving a big, wide door open to problems.

Jack Boyles, Managing Director at Marcum LLP, understands this perfectly well. With his extensive experience in financial planning and modeling, valuations, and funding strategies, Jack keeps a trained eye on both the micro and macro factors that influence today’s rapidly evolving financial services sector.

In this episode of The Modern CFO, Jack talks with host Andrew Seski about critical factors to consider for growing companies, how he deals with the unexpected, and the valuable lessons he learned over his 25-year-long career as founder, investor, and CFO of several companies.

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Please note that the transcript is AI-generated and may contain errors. The content in the podcast is not intended as investment advice, and is meant for informational and entertainment purposes only.‍

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[00:00:00] Andrew Seski: Hello everyone and welcome back to The Modern CFO podcast. As always, I'm your host, Andrew Seski. Today, we're joined by Jack Boyles. Jack, thank you so much for being here. 

[00:00:19] Jack Boyles: Thank you. I'm looking forward to our conversation. I reviewed a number of your other podcasts. They're all great and I learned something in each one.

[00:00:25] Andrew Seski: So today, Jack serves as CFO at Marcum. Jack's based in Boston and has been a CFO across a number of industries and is insatiable when it comes to learning new things, trying new industries. 

[00:00:38] But one of the things that we've been talking about, maybe ad nauseam, but between us is the idea that maybe there is a certain time and place where CFOs can have their biggest impact at, you know, either a type of financing, an industry, and maybe CFOs shouldn't necessarily grow across all stages and all different types of industries. Maybe they should be specialized and maybe there is a time and place for that CFO who can drive the most value. 

[00:01:05] So this is a topic I really want to dive into and really dig our teeth into because Jack has such a unique vantage point, serving his entire career really honing in on this idea. So Jack, I got to turn it over to you to tease out some of the value and insights here on sort of that topic and whatever else we can foray into across all of the experiences you had as a CFO.

[00:01:26] Jack Boyles: Thanks for the great introduction. Yeah, I'm not CFO of Marcum — number one. Marcum has a group of consulting CFOs and so I now work with roughly a half-dozen small and medium-sized companies as a fractional CFO. Prior to that, I've been CFO of a number of companies in which I was founder, investor, angel, and always had a CFO title in a wide variety of verticals — distribution and logistics, software manufacturing, IT services, natural resources. 

[00:01:57] And right now my portfolio includes a SaaS company — a company working on carbon credits with blockchain — and another marketplace for health services. So, you know, it's a pretty broad spectrum and I've enjoyed it because there has been a number of learning opportunities. 

[00:02:14] But returning to your theme, I found I'm really good at the five million to 50 million-dollar service orientation companies. And I've realized that that's where I can add the most value. I'm not somebody who can take a company public, although I've sold a number of companies to Fortune 500 companies. But it's really recognizing there are different skill sets for those by both vertical and by size of company, if you will, the capital intensity and sort of the economic structure underlying the business.

[00:02:45] So I can break down those and, you know, they're all interesting problems, but it's really a different skill set for each one of them. And you need to manage differently as that, you know, financially-oriented team member. 

[00:02:58] Andrew Seski: In terms of where some of this interest comes from from my end is the fundraising environment over the last few years dramatically changing in the last few months. So what may have been, you know, a company doing five to 10 million then that could have been valued, and maybe in the software land, maybe even at a hundred X multiples at one point, just an absolute crazy valuation and fundraising environment to, you know, a very, very immediate, almost shift in going from, you know, pure growth orientation to conservative cost cutting, you know, headcount reduction. And I think the question there stems not only just from where the CFO can be the most valuable in their niche and their competency, but also how to weather the volatility of different market cycles. 

[00:03:42] And there are a lot of variables to play with here so I really like your answer that the CFO can be really valuable by identifying their impact in a niche due to all of the other market environments and volatility in the markets that could, you know, shift strategy and financial strategies that a company may pursue.

[00:03:58] Jack Boyles: Well, you're shining a spotlight on, you know, certainly what is the most critical thing for growing companies, which is, do they have access to capital? And is it the right capital on the right terms and in the right timing? You know, obviously, you progress from family and friends to seed rounds, to Series A and up. 

[00:04:17] But it's really more important, or the starting point for that analysis is really, what's driving the need for cash? Is it building your organization? Is it financing working capital? Is it plant and equipment expansion? Is it building relationships that you need to invest in? So really understanding from a, what I would call a fairly granular level, what are the cost and capital drivers in your business and really internalizing that, that economic, that, you know, the calculus of the business, because that's gonna tell you what kind of capital you need and where to go knocking on the door. It's seldom the case that you're gonna be the first guy knocking on that door, but making sure that they understand your economic model is critical.

[00:04:59] And so to narrow your field down on who you're focusing on and what you're offering and making sure, I mean, whether you look at PitchBook or anything else, it's fairly easy to qualify those people and what their investment criteria are. Most firms are very upfront about what they invest in and there's nothing wrong with reaching. But there's also economy and wisdom and finding people who've done your deal before with like competitors because they understand it. They get it. Whether you consider that investor a bank or a venture capital or a family office, find people who have done it before. They're gonna bring more knowledge to the deal — in the one they do because they are always seeking to be better. Their due diligence will be a lot more efficient and helpful to you.

[00:05:43] Andrew Seski: So I want to dive into something that comes up on most podcasts. When we talk about people's route to CFO roles, there's a very traditional background of accounting courses throughout undergrad and maybe a consulting job or a Big Four role. We've had a mix between a very traditional and maybe some nontraditional of serving in the Navy. And I want to go back in time to Dartmouth undergrad and leaving school. What was your, some of those first roles? Did you have sort of a traditional background? Because I want to then kind of hit on all the successes you've had because you have a pretty incredible track record as well. 

[00:06:19] Jack Boyles: Not at all. I got an MBA at Dartmouth and I was something of a quant jock having a mathematics degree and liking computers, which was kind of a new thing then. And, you know, took all the accounting courses. And when I got close to what the careers looked like with the Big Eight — and there were eight at that time — versus the other things that were out there, I chose consulting. 

[00:06:41] I joined a firm, Temple, Barker & Sloan, in Boston, worked with them for years. And candidly, they liked me because I spoke business and I could write Fortran. Those were the qualifications. And so I ended up doing most of the financial modeling on a broad range of projects and really, you know, got to be known as something of a guru in figuring out the economics in how to simplify them to the important details. I mean, that's an important notion. 

[00:07:07] Getting a level of detail right is sometimes the hardest thing to do right in making a projection. Too detailed — you can't maintain it, change it, and it's not useful as a policymaking tool. Too macro — it's not informing you on what the really important relationships are between the resources and their results in a business.

[00:07:28] I did that for a number of years, worked across telecommunications, oil and gas, resource recovery, some consumer products, and then got tired of working for big companies because, you know, you were kind of siloed. And so when I looked over my years in consulting, the fun companies were all small and growing. That made the choice easy. So I went off on my own and one after another, you know, lived out that dream. 

[00:07:53] Andrew Seski: So you've mentioned early on that you are really passionate about continuous learning. And I think you probably identified consulting as one of those ways to be very, very oriented to try to be a value adder early on in your career but also across a lot of different industries so that you can continue to learn. It's very clear that you maintain that theme by being able to have a similar job title across all of these different types of firms.

[00:08:18] But how are you thinking about that in terms of some of the risk profile of — I think there are a lot of CFOs who have probably fairly, just a pretty well-defined risk adversity — but going from big consulting shop to smaller firms to deploy some of that knowledge, did that phase you at all or were you pretty comfortable in those positions? 

[00:08:37] Jack Boyles: My wife didn't ask a lot of questions about what I was doing. So honestly, I was blessed with somebody who was very supportive and understanding and had confidence that I could make it work, whatever I chose to do. And she's, you know, she's been half-right.

[00:08:52] Andrew Seski: Well, let's start talking about some of the consistent themes across these CFO roles because you do have a lot of experience in successful exits. Like I mentioned, your track record is incredible. So I want to dive into some of the themes and valuable lessons that we can share to the network of CFOs and listeners today.

[00:09:11] And maybe it starts with the kind of continuous learning aspect of always trying to drive forward continuous learning. Maybe it's the definition of what a modern CFO is across being somebody who's really proficient in understanding and measuring the value of technology versus maybe opportunity cost. So were there any things that stood out really early in your career that were cemented later across some of the more successful exits that you've had?

[00:09:40] Jack Boyles: I think one of the most important things to do is not overestimate your team's understanding of what the CFO is really supposed to do. And I think it's really helpful when engaging, you know, with a new team to lay out, you know, your assessment of what the roadmap is and what the principle projects are, the priorities, timing, and resource required for them. 

[00:10:02] Above all, we have to be good project managers. Yes, we have to have the financial disciplines and understand how to put financial statements together and make intelligent decisions about IT, infrastructure, and risk mitigation, and so forth. But really laying out that roadmap for your team members and really saying, "These are the things I own," "These are the things I need your support with." And don't assume that they really understand what the role is and how integrating it needs to be in how the business develops. 

[00:10:33] You know, the CFO should really take responsibility for building the infrastructure to support the vision of the people who are creating the products and services and the technologists in this day and age that are driving it forward. But to really confirm their understanding of your role, the need for detail, the need to measure what they're doing and provide regular feedback in particular that monitors their progress against their objectives. So to me, that's a lesson I learned over and over again and every time I skip it, it's like, how did I miss that? It's just, I thought I had learned that lesson the last time. And that's critical whether it's, you know, regardless of what industry you're in. 

[00:11:12] You mentioned the other thing about the thing that keeps me motivated. You know, one of the things that happens at business school and when you're a math major is you acquire all these analytical techniques and tools. You know, I'm really in the business of, you know, old tools for new problems. And so when somebody talks to me about security policy — huge issue for most companies today in the security, you know, whether it's compliance with GDPR or SOX to any of those issues — you know, you don't hear anybody talking about applying Bayesian analysis to that, which is, we all know the technique, but use that framework to structure the decision, to add quantitative data and substance where you can, but also understand, you know, what you're not gonna know and is undiscoverable and be able to make decisions. 

[00:11:59] You know, the role of a CFO if they're effective with not only the preparation of financials but can adapt that data to the decision making that's in front of them — that's critical. That's a valuable, valuable partner in your decision-making process. Not that they don't get a vote — they do and should have a vote — but the reality is making sure we've chosen the right analytical framework and context for the problem, understand what we know, what we don't know, what's worth researching, and how much time and resources are we willing to spend to improve the decision. Critical thing. And it cuts through a lot of the maxims you hear from one CFEO or, you know, one entrepreneur or the other, speed is everything in one case, fail fast. You hear all these things, but putting it in structure and putting numbers to it really helps you apply those lessons in a very focused and constructive way.

[00:12:54] Andrew Seski: I want to continue to talk about this just for a moment because we've had now the pandemic. It looks like we already have a looming recession. When we talk about constructing sort of traditional models with a little bit of leeway and communicating out, you know, exactly what the role of the CFO is, how do you create and think, or how do you personally think about how to create some sort of, you know, configurability around circumstances changing and some sort of flexibility in terms of, you know, creating the models that would be able to handle, you know, some of the maybe more unforeseen types of events that we've had in the last few years?

[00:13:29] Jack Boyles: Oh. 

[00:13:30] Andrew Seski: It's a complex question. 

[00:13:32] Jack Boyles: Well, I mean, you know, there's great literature on that over the past 10 years, starting with The Black Swan and the work of The Undoing Project, which is about people, you know, two psychologists won the Nobel Prize in economy and economics for really undoing capital markets theory, is what they did, and sort of challenge some of the basics of, you know, thinking fast and thinking slow, which is Daniel Kahneman's famous book. 

[00:13:59] Andrew Seski: Is Undoing, is that a Michael Lewis? 

[00:14:01] Jack Boyles: Yes. The Undoing Project is the story of Kahneman and his partner that led to the Nobel Prize. Kahneman, you know, his partner died in this research, but Kahneman continues to write and is still very influential about thinking about how decisions are made and what we, what we just assume and make decisions on every day, which needs to be tested, which is sort of at the root of these unforeseen things that nobody saw coming. 

[00:14:29] I'll segue back to something I raised earlier: security issues today. You know, when you ask Amazon and you've moved all your stuff to their cloud services, you know, what are you gonna do to make sure we never fail? And they say, you're making an assumption that we're not gonna fail sometime. Assume that the network's gonna go down at some point. That's a real risk. How are you gonna handle it? We can't provide that guarantee. I think about risk in that way, which is I really do carefully consider obsolescence risk of products and services. That's particularly relevant today given the pace of technological innovation and disruption going on. 

[00:15:05] I think, you know, we have to think very carefully in most businesses. The current clients that I have are not really geared in doing flexible planning regarding the likely wage expectations of, you know, anybody they're hiring. You know, it's not just the commission you pay a recruiter. It's the fact that the basic wages are gonna be 10% higher. So really working through at a fairly, you know, a mid-granular level, which is wages, resources, regulation can change and fundamentally alter the nature of competition in your vertical competitors themselves as well as new products and services. And I think you just have to be structured about that and really be honest. 

[00:15:47] People wave a hand at it by saying we've got very strong customer relationships. Well, yeah, maybe you do. I can look back and see what the recurring revenue is per customer and I'm not sure what that tells me, you know, given the threats to their business, the threats of competitors, you know, this is a free market capital society. They're gonna earn money for their shareholders and do what they think is right for them. You really have to be very circumspect about placing too much reliance on those strong customer relationships that you've had forever and even the legal contracts underneath them. I tend to be a skeptic when it comes to that.

[00:16:26] Andrew Seski: Right. Having a really, really specific understanding of stakeholders, you know, not just your stakeholders but their stakeholders and, you know, whether that's their investors, the shareholders, employee owners, you know, the things that affect their businesses and your clients' businesses as well.

[00:16:40] Jack Boyles: Everybody at the table.

[00:16:42] Andrew Seski: Everyone at the table.

[00:16:43] Jack Boyles: Everybody at the table has alternatives and it's important to understand that you can't, you know, neglect any of them and because whether it's your circumstances or their circumstances that changes dramatically, you both have to re-examine the relationship and be prepared for it.

[00:16:59] Andrew Seski: One of the things we were talking about just before we started recording were some big shifts that have taken place in terms of where financial data is stored, maybe the, like sort of the future of the CFO role. And I want to touch on some of that because I think it'll reframe some of the conversation into what we can think about in terms of strategic planning in the next three to five years or even zooming out further with more innovative technologies. You mentioned you had a blockchain company that you're working with doing carbon credit so you're hitting two major themes that, even in the news right now around climate change and government funding, some new climate initiatives.

[00:17:35] So I want to zoom out a little bit and talk about some of the macro things that have happened in terms of where technology and financial services have intersected, especially in the role of the CFO. 

[00:17:45] Jack Boyles: My perspective is if you look back over 50 years, there have been three or four major events that wholly changed the way finance was supported within companies, starting with the creation of ADP. When Frank Wattenberg created that company back in the sixties, nobody dreamed that you'd ever have the confidence to outsource the most confidential data you had, which is the compensation of your employees. You know, 10 years later, you were considered inefficient and backwards if you weren't using an outsourcer to manage the payroll processing problem. They did it better. They did it more competently. They were well-equipped to keep pace with a compliance requirements that constantly changed. Looking back, it was like, why didn't we do that earlier? 

[00:18:29] A couple years later, we moved from big, secure IBM mainframes to running our financials on little local area networks everywhere that rolled up. It was a revolution from having to have a mini computer, a mainframe to process your financial data or, worse yet, do a lot of it manually. That happened, you know, overnight. We all changed again with the year 2000 worries and upgraded all of our technology. 

[00:18:58] The last thing that happened was the move to the cloud. In 2015, I remember talking to financial partners about, you know, was anybody else contemplating moving their accounting onto these crazy platforms, NetSuite and Intacct? Not a one. I talked to a dozen companies. Not a one. Three years later, they were behind the eight ball if they weren't in that project. And now you have to have a very stable, very small business if you haven't moved your financials to the cloud, whether it's on Oracle or SAP or Intacct or NetSuite or QuickBooks Online. 

[00:19:34] And I predict the next, you know, role to change is the CFO. I think that the reality is the breadth of skills that a CFO had to bring 20 years ago is irrelevant today, largely. You know, the person you want in that role has great familiarity with the vertical, has great familiarity and comfort with the size of company — how many people, what's the size of the management team. You work entirely different if you're in a C-suite of a Fortune 500 than if you're one of three people running a 50-million-dollar company and you have very intimate and intense relationships with the other members of that C-suite. 

[00:20:13] So I think that's going to change and you're going to find, you know, CFOs, particularly for growing companies, change more often. Somebody who's really good from startup to 10 million. Somebody else has a different skillset from 10 to a hundred million, and you need somebody else for the IPO. They're different skillsets. You know, the lower you go, the broader range of skills you have to marshal and more hats you have to wear as you go up the chain, you become more of a manager and in public relations role. 

[00:20:46] So within the sectors that I serve, I find that it's as important for me to be able to source critical services, whether it's in IT, professional services, legal accounting, insurance, or other specialty services, whether it's R&D tax credits, 401(k) advisory work, issues of that nature. So I'm, you know, a third sourcing agent for all the professional services, a third, you know, controller, whatever accounting hat I have to wear. And third really business planner partner to the other executives. 

[00:21:20] Andrew Seski: So that's really helpful in terms of contextualizing all of the dynamic requirements of the CFO today. And I think it's really helpful to look backwards before looking forward. One of the things I want to segue slightly into — maybe it's more consistent or maybe it's even changing now because of everything that is more standardized and in the cloud — but I want to talk about liquidity and exits and relationship with CEOs. 

[00:21:45] You've had a number of exits and I'm trying to decide if I have an opinion whether or not transactions will always be complicated. You're always gonna need to bring all of the stakeholders we've mentioned into the same room to hash through details and figure out what's best for buyers and sellers. And while there might be some standardization, there's still a ton of human-level emotion behind, you know, exits. 

[00:22:09] So I want to know if there's been any sort of intersection between the efficiency of due diligence and exit planning. Has technology influenced all of that or is it still highly manual? A little emotional as always in building great companies and maybe having an exit, but it'd be a fun thing to think through and talk about because it's been a hard few years. I think the number of transactions that happened in the last few years have probably been off the charts. In the early 2020, I think 2020, there was record number of IPOs, first half of the year. So just thinking through that, I would love to hear either stories or lessons learned or, you know, your perspective on whether or not you think technology's gonna impact liquidity and exits. 

[00:22:50] Jack Boyles: Well, I think two things. In terms of the mechanics of it, you know, the progress in deal rooms and standard terms and analytical tools to look and value companies is extraordinary today. The tools at our disposal to do financial analysis have never been better. I think the hidden value of the technology isn't just the deal room and the ability to communicate better. I think you also find that people who've done a number of transactions are starting to put more and more emphasis on what are the fundamental infrastructure systems that are in place. 

[00:23:25] If I'm buying a company that's using the same systems I do, hallelujah. My transaction implementation cost have been cut by two-thirds. I'm not retraining their staff. I'm not reinventing the wheel. I'm doing some data cleanup at consolidation. So if you're a small company or mid-size company with a view towards being bought or buying others, choosing an industry standard platform for your ERP is critical, you know, that's not customized. It greatly simplifies and ensures the success of a transaction because it means you spend, you know, two months integrating operations rather than a year. Time is of the essence in these transactions. 

[00:24:07] And I think we're gonna go into a phase, particularly with, if we are in fact in recession and are likely to see a number of quarters and the capital pools are gonna dry up or be constraints fundamental, I think you're gonna see a wave of consolidations among these companies and that's gonna be their choice, either sell their IP and their customer lists if they're just technologists or go out of business because I don't think the subsequent rounds that were readily available two years ago are gonna be coming as quick or be as favorable in terms of valuations. 

[00:24:40] So when you look at the, you know, how the worm's turning, I would urge mid-size companies, who are revenue, you know, have profitability, positive cash flow, to really think about who are the comparable and natural acquirers for them. Chances are those companies, if they need to exit or thinking about it, they probably know who their acquirer is. And I would in some cases that, you know, urge them to have those conversations before they engage in investment banker because we're all looking at the same two-year outlook, which is highly uncertain in terms of both economic environment, as well as the availability of capital. And I'd plan for that. 

[00:25:20] In most cases, you know, companies that are consolidating in some form, they already know who the players are. And they know, and they're very thoughtful and intentional about what they're gonna look like to facilitate that and remove obstacles to combinations. 

[00:25:35] Andrew Seski: So just thinking from an investor's standpoint and from a founder's standpoint, I think in the next three to five years, there's kind of a double-edged sword here. I think on one hand, there's some excitement around if there is a downturn and money is being spent more strategically and maybe a little less out of fear of missing out on opportunities than there is that shakeup where really there could be some market dominators, if they can survive a downturn and really capture a big part of the market share in their industries.

[00:26:07] So I think that is somewhat exciting to see the shakeup. It's probably nerve-racking as well for both investors and founders in the same vein. But I was gonna ask if you were really excited about anything on that kind of time horizon. I know we just mentioned the next two years feel very uncertain. But just from all these different perspectives, I was thinking it might be unique to hear what you might be excited about in the next three to five.

[00:26:30] Jack Boyles: Personally, I think, you know, the whole promise of blockchain technology, in particular smart contracts, is really going to change finance in very fundamental ways that most people don't grasp yet. When I consider simple things that we had, you know, trade finance, importing goods from another country where it used to be a long, drawn-out procedure with very strict guidelines for the documentation and a very globally revered process for clearing payments and managing the transport of goods. That's a blockchain transaction. That's a smart contract today and it's collapsing.

[00:27:05] Well, you know, that's, those same technologies are gonna influence lots of things in the finance world. And so I honestly see financial organizations changing dramatically. So individually as somebody who's working with small companies as a finance guy, I find that very exciting to anticipate those changes because it'll be as important as outsourcing payroll and moving your financials to the cloud and fractionalizing your CFO. It's really gonna change the way things work. 

[00:27:34] And the, to me, the biggest question is, it's not "if," it's "when." Is it, it could be two years. It could be five years. It could be seven. I'm not smart enough to know what the obstacles to adoption are. Oh, maybe I do. Yeah, I'm guessing it'll be government.

[00:27:48] Andrew Seski: Well, I think there are a ton of regulatory pushes being made like, as we speak, basically. But I'm glad to see that a lot of the blockchain applications that are catching some traction are around decentralized finance. It's a really hard problem to solve. But there are a lot of people trying to put certain blockchain applications out there where it's sort of a square peg in a round hole. It's a more natural fit, I think, in a lot of the legalese of smart contracts being digitized. So I'm also looking forward to that. 

[00:28:17] I always ask whether or not you feel something is, you know, maybe undervalued or underestimated in the world from your vantage point. I know we've touched on a lot of big themes across innovative technology, across the changing role of the CFO. But just wanted to give you the opportunity if you wanted to take the conversation in really any direction where you just feel that people may not fully appreciate something that's more clear to you given all of your industry experience. 

[00:28:45] Jack Boyles: This is hard for somebody who's a numbers guy to say, but the proper functioning of teams is more important than I ever wanted to admit, you know, as I chose to be a math major and then went, you know, focused on quantitative things in my consulting career. And I think COVID and virtualization of so many organizations, I think there'll be another library filled with the books consultants write in three to five years about what separates those companies that did that well and knew how to bring back and re-engage their workforce. 

[00:29:18] The successful company that, you know, that we write about five years from now is not the one that said, well, you know, starting 2023, you've gotta spend two days a week in the office. They're gonna be a lot more sensitive to it. They're gonna be a lot more, they'll learn a lot more from how the teams functioned during COVID and immediately thereafter and they'll figure it out. And that's gonna separate the real winners and the teams that have, you know, long-term, excess profitability, and market valuations, and all of those other good things from the rest. Because once you can do that, you're accessing a global workforce, which means you can, you know, do a much better job optimizing, you know, targeted recruiting at the best cost. You'll find centers of excellence and be able to tap into them much more rapidly than a firm that's constrained and tied into some old HR, you know, notions of how this should work. 

[00:30:11] So I can't predict who those companies are, but that's what I'm watching very carefully. What are the innovative companies doing when it comes to how they manage their workforce, how they reward their workforce now that we've broken the model that says you show up in the same place every day. 

[00:30:27] And you know, certain industries are, certain companies, those that process medical claims, for example, have led in sort of, well, we don't have to do this in New York City; we can do it in Upstate New York. Or, you know, there are lots of examples of people that have taken a function and done it well, but it tends to be a very routine function and it tends to be easily supported remotely.

[00:30:50] You know, the last two years gave us an opportunity to blow everything up and try new models. As somebody who's enjoyed a business career and continues to enjoy seeing what's coming, I'm really looking forward to seeing who the winners are in that race. 

[00:31:04] Andrew Seski: Yeah, absolutely. I was curious if you, I know you've been somebody over the course of your career who's continuously pushing the envelope on trying to find whatever is on the horizon. I'm curious as to if there are any unique sources that you look to. I mean, I've mentioned on other podcasts, I still get a physical Wall Street Journal. I'm very careful on how I curate social media and how I get news. And it's, you can just so easily be bombarded. I'm curious as to how you curate what you receive or if there are any kind of unique ways that you go seek out information or book recommendations. 

[00:31:38] And I only ask because Nth Round just launched a newsfeed because we are the same way. Everyone on our team has such unique access to really different types of news and we consolidate it and try to, you know, just showcase what we're thinking about that we think is interesting. It's always kind of a really unique niche between finance, technology, regulation, but it's important to us. And it's just a really interesting mix of news. So I'm just kind of curious as to, you know, as you look to your next revolution of Web3 and blockchain and everything that's happening in the world of technology and finance and regulation, kind of how you're sifting through, you know, the huge amount of content.

[00:32:16] Jack Boyles: You know, honestly, we're drinking from a fire hydrant right now.

[00:32:20] Andrew Seski: Absolutely. 

[00:32:21] Jack Boyles: I mean, just, you know, there's so much new technology and I've never prided myself as someone who can create technology. But I've always thought I was pretty good at seeing its applications and where I could really have a role. So having said that, you know, I do scan, I love to listen to a16z podcast. They always seem to be ahead of the curve in terms of identifying a technology and sort of what the fundamental economics are that are gonna, you know, lead to mass adoption. So I find that to be a great source of ideas in thinking about what's coming next. 

[00:32:54] Myself, I tend to go to raw data. Who is the ex-CEO of Microsoft, not Bill Gates' successor. Who's created a, you know, an American facts database. So I'll open the phone book, essentially, of facts — the Census Bureau, the tax rolls, you know, Bureau of Labor and Statistics — and look at something that may, you know, based on the idea that there's a new technology, say, well, if this applies to plumbers, how many plumbers are there in the world? You know, where are they, what do they do? Really understanding, sort of not trying to solve a global, you know, moonshot problem, but is there a problem everybody has in their household every day that this widget, this service might address? 

[00:33:37] To me, I am a low-hanging fruit guy. So if there's a problem that says, you know, there was really a better mouse trap, I'd be all over it because I can estimate how many mice there are and think about the problems of addressing that problem. So that's kind of how I think about things. 

[00:33:54] I do have an example. I ran into a company that was doing field service in electronic repairs. I looked at it and said, well, there's 300 or 400 companies you have to maintain relationships with for warranties. And there's four to 5,000 of you guys across the nation. And there's only one national player? That doesn't seem right. There's an arbitrage. There's a roll up here. 

[00:34:14] So to me, that was an interesting problem. I worked on it. We merged a couple companies, interesting things. But I'll look at the existing situation in an industry. I think I'm pretty good at looking at the macro forces of how an industry works, how a business works, see where there's a real arbitrage and next opportunity to exploit, you know, not trying to reinvent the wheel, but make it work better, consolidate where possible. 

[00:34:40] Andrew Seski: Well, stay on after the recording. I've got a very funny story. I'll have to confirm, but I believe it's told on the podcast, it's a Steve Ballmer story about early Microsoft days. But one of our podcast guests had to report to Ballmer and got some very implicit advice in his early career about efficiency and modeling, you know, assumptions after data. So we'll talk about that as we wrap up. 

[00:35:03] But how would you recommend people get in touch if they'd like to talk to you about any of these concepts that we've covered today or get in touch with Marcum about maybe utilizing some of the services that you're currently serving? 

[00:35:16] Jack Boyles: The easiest thing. I'm on LinkedIn and very visible, Jack Boyles. There aren't that many of them. So you should be able to find me. There's also a jack.boyles@marcumllp and msn.com as well. So, happy to take all calls and look forward to chatting with anybody who found this an interesting conversation. 

[00:35:34] Andrew Seski: Excellent. Well, thank you so much for joining The Modern CFO podcast. And I hope to talk again soon.

[00:35:38] Jack Boyles: Great. Thanks, Andrew. Take care.

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