Navigating Changing Fundraising Environment and Finding the Right Capital

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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Show Links

• Check out Marcum LLP
• Connect with Jack Boyles on LinkedIn or via email
• Check out Nth Round
• Connect with Andrew Seski on LinkedIn

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Transcript

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...