CFO Chronicles: The Secrets Behind Success

What Happens When a CFO Thinks Like a CEO - with Tom Dillon

• James Donovan • Season 2 • Episode 34

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What if your biggest bottleneck… was you?

In this episode, James sits down with Tom Dillon of Frak Finance, a former investment banker turned fractional CFO, to unpack the real reason most firm owners stall out- and what it takes to scale beyond the “one-man band” model.

You’ll learn:

  • Why hiring before you're ready is often the smartest move
  • How to remove emotion from high-stakes financial decisions
  • The moment Tom knew he had to fire himself- and what happened next
  • What most fractional CFOs overlook when it comes to client growth
  • How to build a team that operates with calm, confidence, and clarity

👉 If you’re serious about building a sustainable firm with real infrastructure - not just a job you own - this conversation will flip the switch.

Send us a text

Feeling stuck in your growth? Discover how to elevate your marketing, personal brand, and sales approach to attract clients who value your expertise.

Ready to make a shift?

Book your strategy call today at accountingleadsnow.com

Speaker 1:

Welcome to CFO Chronicles the secrets behind success the go-to podcast for fractional CFOs and accounting firm owners who want to attract more high-paying clients and increase their revenue. Hosted by James Donovan from Nine Two Media, this podcast dives into marketing strategies specifically designed for lead generation and client acquisition. In each episode, you'll hear from industry leaders sharing their success stories, and Today I am joined by Tom Dillon from Frack Finance, based in Chicago.

Speaker 2:

Tom, I know we were going back and forth a little bit here before the recording. I'm super excited to dive into your story, hear a little bit more about you and for the listeners to learn about you as well. So welcome to the show.

Speaker 3:

Thank you. Thank you for having us. It's a pleasure to be here.

Speaker 2:

Awesome. I want to start off real quick because your background it's showing a picture what looks like a golf course. You have a flag from one of the pins. I would love to hear a little bit about that golf course. There must be some significant meaning if that's hanging up in your office.

Speaker 3:

Yeah, so I couldn't normally blur that out, I couldn't get the thing to upload on zoom. But yeah, that's um Arcadia bluffs Uh, it's where I got my first hole in one. Okay, so it's a. It's a top public course up in Michigan, right on the bluffs on Lake Michigan, and it's a beautiful course. I would highly recommend it if you can get out there to play that one for sure.

Speaker 2:

Well, congratulations on the hole-in-one. And you mentioned that was where you got your first one. So how many hole-in-ones do you have? Don't have a second, that's just the first. I'm hopeful that's awesome. Well, hey, hole-in-one. I'm not a great golfer by any stretch, but every time you get up to the par three it's like is today the day? Is it gonna happen?

Speaker 3:

so it's cool that that I know. Isn't that the best feeling, especially heading to the masters with everything kicking off today. I just get that, you get that good feeling. That first birdie of the season yeah, it's coming. So. I'm super excited to kick off the season, that's for sure that's so.

Speaker 2:

So, Tom, tell me a little bit about how you got into becoming a fractional CFO. Is this something that you knew growing up? You're like I cannot wait to be older and get into accounting and work with numbers, or like maybe it was. How did you get to where you are now?

Speaker 3:

it was how did you get to where you are now? That is a great question, because no one just starts out as a fractional CFO. It's a leadership position that everyone has to build towards, and so everyone has a story, and I guess here's mine. The original origin story of how the numbers and then I'll get into more of the career was I had tripped and fell on success with selling Cutco cutlery and made a bunch of money as an 18-year-old, and I had talked to my dad about what I should do with it. And he said maybe I'll try to get you a meeting with my wealth manager and he'll sit down with you. And so I sat down with a guy named Chris Crawley, who was at Citibank at the time, and he taught me the rule of 72. And that's, if you divide the interest rate into it, tells you how long it'll take for your money to double. And immediately I was hooked, and so I knew I wasn't going to go down any other profession but finance. And so that's what I did.

Speaker 3:

I up for, uh, for a finance degree, and then after school I went and worked at william blair, which is the investment banking firm here in chicago, and from there, um, I started to quickly realize that there was this entrepreneurial bug that wasn't going to go away. It's a sickness in all of us. I had to do something about it, yeah, you know. And so pretty much in that process, it really became apparent that I was going to go down this path. But I also, being in finance, you're trained to be risk adverse, and so I wanted to de-risk this you know, crazy, jump out of the plane. This, you know, crazy, jump out of the plane. And and so, before kind of doing that, I wanted to make sure that I had some experience in what I called ops chops.

Speaker 3:

Really, all we did at, you know, the investment banking firm was you're sitting in the ivory tower, you're pontificating people's business decisions, but you're not really making any of your own. I wasn't hiring, firing, managing people. You're not really making any of your own. I wasn't hiring, firing, managing people. And so I knew I needed to get that experience if I wanted to be successful, and I had this big idea of you know I wanted to change the world, and so, before doing that, I went and got some experience.

Speaker 3:

I worked at a private equity backed company as their CFO and then was promoted to CEO, ran that for a little bit and then went back to school to start putting this idea through the ringer and at the end of it, the night of graduation, I raised money for this idea and it was a tech company that was going to disrupt the market for ordering and payment at hospitality.

Speaker 3:

So this is pre-COVID, and we had a QR code based ordering and payment system and we had a successful pilot and we were launching to the public the week COVID hit.

Speaker 3:

So now we have a native app, both operating languages, which, looking back, was a huge execution error, realized this wasn't going to be sustainable, and so I fired myself financially, not operationally to keep the team together and keep operating, which I'm sure many entrepreneurs have done dug into credit cards just to get payroll, and so in those moments I realized man, I got to pay the bills. How are we going to do this? So I went back to my roots and started moonlighting as a fractional CFO and so, 11 years ago, going, we're going on 11 years now. Um is when that started and at the, at the, at the point in time where you come to the realization that you're going to have to swallow this painful, disgusting tasting pill of failure, was the real kind of um entrance and commitment into the fractional CFO space, and so it was born out of necessity and then turned into a real passion and love of mine.

Speaker 2:

That's so good. I mean. Failure only happens when you quit, though, and it doesn't sound like you've quit. It sounds like you've just kept going and you've adapted and you found a way to make it work. So I wouldn't chalk this up as failure at all. Or maybe I'm missing something, but it seems like things are in a much like things are moving. Things are in a good spot, things are great.

Speaker 3:

Yeah, that's awesome. I appreciate that. Yeah, I think it's only a failure if you don't learn from it. And so raising capital and you know, and being a fiduciary, having that fiduciary duty to your shareholders, and and um, it's tough, you know you're. When you're a steward of people's capital, it's a very tough position to be in and um, and it's. It sucks when you're, when things aren't going your way, but it's the reality of most entrepreneurs that do raise venture capital face.

Speaker 2:

Yeah, what do you find is one of the biggest challenges that you're facing in this season right now, or something maybe in the last year that you face and you've overcome where you're like you can look back and be like, wow, that was really hard and I'm so happy I pushed through.

Speaker 3:

So I would say it's the J curving of the business model.

Speaker 3:

It's hiring ahead of growth. I think is one of the most challenging things to do in business and before we didn't face this problem and I'm so happy to be on here and love everything you do for this community, james and part of that is the transition of going from a one-man band and being at capacity but cashflow is good, and then having that conversation with your wife realizing I don't have a transferable asset, I'm going to get burnt out. I need to build a team. Honey, we're going to be cutting our margins in half. Well, if they don't know, your significant other doesn't know what margins are, they're going to quickly realize it means you're going to have half the cash flow. So that's ultimately what we did here in the past six months well, seven months, and then we're going to continue doing it for the next five months, which is J curving the business model, hiring ahead of growth and continuing to look to build out our pool of talent, our bench, where we are looking to bring other fractionals on our team and and develop them as well.

Speaker 2:

Yeah, one of the intensives I was just at a couple of months ago. One of the speakers there really successful marketing company. He's been doing it for 10 or 15, 15 years and he spoke about that as well hiring ahead of growth and the point he made that really stuck with me. So it's interesting you're bringing this up. Is that you're?

Speaker 1:

always either overstaffed, or you're understaffed.

Speaker 2:

So you might as well be overstaffed, because if you're in that sweet spot that doesn't really exist, it means you're not growing. And if you're in that sweet spot that doesn't really exist, it means you're not growing. And if you're understaffed, you're putting too much strain on your team and your resources. It was a hard reality for me to accept, hearing that from someone significantly more successful, but that is the reality. And I think I look back at our team at times and I'm like, yeah, I know we've been understaffed and it's tough and it kind of makes everyone in a more panicked state all the time because you feel like you're chasing your tail. But on the other end of the spectrum, it's hard as the owner to be like let's carry more payroll than we technically need right now all the time. So how are you handling that mentally, knowing like, hey, the bills are just going to be more expensive on payroll. We technically don't need this person right now?

Speaker 3:

I have an abundance mindset, not a scarcity mindset, and so for me, it's keeping the positivity and knowing that there's a lot of opportunities out there, because, as you know the success and failure rates of a lot of entrepreneurs people need help, and for us, it's the same thing that we do with our clients, which is we're seeing kind of those micro traction metrics of success.

Speaker 3:

It's those little wins that are building upon each other that encourage us to keep going, that we're heading down the right direction. But it's having a roadmap and building a roadmap to do that. And so for us, we're always thinking about what are the goals that you want to achieve? Are you looking to sell your company? Are you looking to double the size of your team? Because that is the point of critical mass where you really start to cover overhead and you're earning the cashflow as a business owner that you want in distributions and then reverse engineering that. How do we get there? And where are the KPIs? And what is our marketing? James, you know better than anyone what's our marketing funnel and then our conversion rate and sales, and really focusing in on those KPIs and making sure that we're headed in the right direction or making those tweaks in order to make sure that we're moving and pulling the levers in the right way.

Speaker 2:

I love what you mentioned about the abundance mindset, because that is so true and a mentor of mine in the past the analogy that was kind of burned into my brain was like the hand and when it's closed, like you can't grab anything more when your hand is closed, but when you open it up and it sounds so obvious but really opening up your hand, for that abundance of more can come in and there's more available, instead of kind of holding on to every last dollar.

Speaker 2:

So, yeah, I really love that you're looking at it that way. The other thing I'll add in here is I don't know where my business would be if I didn't choose to start working with accountants and fractional CFOs, because I feel blessed, more than other marketing companies in a sense, or other business owners, that I get to speak to fractional CFOs and accountants and people who are so smart with money and strategic thinking all the time Like to get that insight into the business that I think a lot of people don't have access to without hiring a fractional CFO. So that's been a massive step for me and I think our business is growth. What are some of the things that you notice when you jump into new clients where they're like you, kind of see that penny dropping moment or, like their, their brain just break when you give them some information that might seem so basic to you 13 week cashflow is a big one and giving visibility for a business owner to feel comfortable that money's going out but it's coming back in, and having predictability around that.

Speaker 3:

There's no better peace of mind and clarity. It's very scary to make decisions when it comes to your personal cash in a void, cash in a void. And so that, I think, is the number one aspect where kind of not, it's not a light that goes on, it's more of well, it is, it's more of a light goes on and now I can see. I can actually look and see where we're going, and not in the dark. And so those moments of realizing that I'm not in this siloed echo chamber of decision making, that I have a strategic partner who's the financial adult in the room, who I can bounce anything off of and get the strategic insights of yeah, we've been here before. We understand this. Here's a playbook on what's been successful in the past is super helpful. The same thing with you when you talk to people in our community, james. You're like yep, on what's been successful in the past is super helpful. The same thing with you when you talk to people in our community, james. You're like yep, we've been down this path, I know it works, let's, let's ride. And so I think it's very similar there, and a lot of times when you ask too about you know how do you know if things are going in the right direction?

Speaker 3:

For me personally, we we focused a lot on our depth and experience and we really lean into that, and lean into it in a heavy way, where we can't service clients in the right way without having that experience. And so continuing to grow our bench and grow our experience with new team members is really how we continue to grow. So having that abundance mindset, hiring added growth, allows us to do just that, and so for the clients, it's kind of the same thing. It's really bringing that extra level of experience that they also they otherwise would not have had on their team. And those moments are wonderful, that they feel like they're making the right decisions and they've got someone in the room who is checking to make sure that, financially, this is the best and sound decision that's, I mean, one of the biggest things I've noticed with with your industry and the clients we've worked with, the conversations we've had other guests.

Speaker 2:

You guys do such a good job at removing the emotion from all the decision-making and then it just makes it so clear this is what the data tells us to do. There's no emotion that goes behind it, and emotional decisions generally don't lead to good outcomes for the most part, especially in business. But yeah, you guys do such an amazing job at just like here's the math. Here's the numbers. This is telling us what we should do, but not every business owner knows how to look at the numbers in that way, so it's pretty cool.

Speaker 3:

We're not completely callous. We do have emotions, but it's a very, very good point. Removing them takes a lot of effort. I think you have your physical health and your financial health, and if you look and talk with a lot of doctors, they're trained to remove the emotion from the decisions of giving that bad news or putting a path in place to rectify the issues and problems that someone has from a health perspective. I think it's the same thing that somehow, along the way, is ingrained in us and you do come a little, become a little callous, but the emotions are still there. You just learn to move past them quicker, that's cool.

Speaker 2:

Is your team all all in house or like sorry, in your office, or do you have some remote workers as well? What's the structure of your team look like?

Speaker 3:

Yeah, so we're mostly remote. We have three people here in Chicago which is incredible Bringing on a new CFO this week, which was just a wonderful yeah, the best feeling you know. Helping the clients, growing the team those are the most wonderful feelings you can have as an entrepreneur. And so what we really have in three core services we do if you're buying a business, growing a business or selling a business. So we really look at the life cycle of growing a business or selling a business. So we really look at the life cycle of the entirety of an SMB owner, and so from that perspective, our team is a little diverse. So we do have the bookkeeping, we do have the forensic accountants that are doing quality of earnings, and then we have our fractional CFOs that are looking at growth and then, obviously, m&a from a sell side perspective, if companies are looking to sell their company. So our team's a little diverse. It's not just fractionals.

Speaker 2:

Yeah, that's cool. What's been kind of your success recipe when it comes to hiring talent or where do you source talent? Do you have any insight you're able to share there? Because I know a lot of other firms out there are also growing and hiring and finding good talent is tough. So what's been working well for you?

Speaker 3:

We look for people that have been kind of battle tested, in the sense that have either worked with companies that may have been distressed or in hyper growth mode that they have been.

Speaker 3:

That cash has been a huge focus of theirs and it's been the success of managing that cash appropriately for capital allocation, resource allocation, that they have a proven track record there and I think, just in terms of talking about it and recruiting in that way, it's led to an extremely strong team, because if they understand that you get it, and if they've done it before, they want to work with a team that is equally as strong and that's going to also help add perspective. Or, if there's an issue in terms of different aspects, someone might have not done an M&A deal before, but they've got a client that wants to grow through acquisition for inorganic growth Great, you know, let's tap so-and-so, you know, and so whatever that looks like in this scenario, you know that's. That's where I think kind of you are able to recruit. The talent that you want is by offering more resources to people who are already high caliber. That's cool, that's awesome Tom.

Speaker 2:

what are you guys doing at your firm to get new clients interested in working with you or to get on the radar of potential new clients? How do you guys market?

Speaker 3:

Yeah, so it's a great question. So just two years ago is when we really branded ourselves and it was just me as the one man band, and now we're shifting our entire mindset to growing as a team and focusing on the leads and our marketing funnel and then the sales conversion funnel. And I'm thrilled to have found you, james, because we're in the process of going through that as a firm of how can we improve in this aspect, because originally it was just hey, I'm at capacity, I get clients. Now we're here and making great cash flow and you don't really have a concern because a lot of those easy wins are just from referrals and going to a handful of networking events. But then it goes beyond that once you have a team and you have to start feeding the machine consistently. We're in the process of learning a lot of that and we're trying to expand and learn. And so I was listening to all these incredible guests that you've had the past two days and it's just super impressive, all the talent that's out there, and it's super impressive all the people who are out there assisting and helping this community of fractionals and accountants from that exact angle.

Speaker 3:

For us, what's been working is trying to be an authority getting on podcasts, getting into speaking engagements and putting yourself out there. And I think the only way to really do that is, if you're starting out and you're looking to transition to becoming a fractional CFO or an independent accountant, and hang your own shingle. I think those, the early days are maybe go work for another firm, go learn best practices, get some clients, get some experience, get battle tested. Once you're going to be stepping out and going and hanging your own shingle and worrying about you know that business development aspect, you know that's where you really lean into those experiences and you know terrible word but case study.

Speaker 3:

But when you're speaking and you're able to pull from those experiences whether you're on a podcast, webinar or getting on stage at a conference and you know and being a value add speaker to the audience, I think that's really where you're able to draw from. And so, in terms of cadence of how do you get there and how do you become an authority, if you feel like you have imposter syndrome, you're not alone. Everyone that started had that. You have to break through it with getting experience. One of the best ways is just start doing and now you can draw from those experiences, you can be the authority of wait a minute. I remember when we did this for a client and that was super successful. Maybe this could help other people.

Speaker 2:

Tom is getting on podcasts, getting on stage. Is that something that comes natural to you, or did you have to develop and level up into this version of who you are right now? That something that comes natural to you, or did you have to develop and level up into this version of who you are right now?

Speaker 3:

So I grew up with three brothers, so four boys in the family. We were pretty rambunctious group of boys, so I think there was some level of competitiveness in there that's constantly driving me and pushing me into probably the uncomfortable. I was the third in my family and so you've got two older brothers. You're always trying to keep up with where things were probably always uncomfortable, where you really just are pushing yourself and trying to compete. So innately there's, there's something there inside that's driving. But from a perspective of you know, do I love public speaking? No, I don't think everyone loves public speaking. Have I gotten to the point where the nervousness goes away? Yeah, but that's all in preparation and reps.

Speaker 3:

When I was thinking of coming on here last night driving home from Milwaukee at a networking event, um, I was thinking of some amazing people that I met there. Um, I was also thinking about what I was going to say. There was a little nervousness that pops in here. You know, james has had these amazing guests on. How am I going to add value to his community and his audience? Um, I don't think that ever goes away, and so it's with preparation and reps that you just kind of move past it and you learn to kind of, I guess, love it. But yeah, so do I like it now? Yes, absolutely. I enjoy it because I find that it's helpful and it gives you a clear picture of what you're trying to convey to your audience. And there's still a ton of work to do. I was listening to one of your guests, ken, and I thought he was just such an incredible speaker.

Speaker 2:

Yeah, yeah, he's good Very well, and that's motivating.

Speaker 3:

It's like, okay, let's, let's get polished. Like I was telling my wife, I'm like man, one guest was incredible, super well-spoken and so and there was tons of them. Just first one that came to mind. It was one of the most more recent ones. So you know, I know that was a long-winded answer to your question. That's great. That's great. Be helpful to those that are a little bit more nervous, um, um, that don't want to put themselves out there.

Speaker 2:

You're extremely well spoken. So that's why I had to ask, because it seems like it just comes off super natural and that's why I was wondering if this has always been like hey, I can just jump in front of the camera and speak, or if you've kind of morphed into that version. And so that's a great answer. I was the best man at a friend's wedding two summers ago and I was so nervous to speak and give a presentation and my friend told me he's like it's not, and the way he presented it to me really erased so much of the nerves that I'm going to try to carry in to any talk and but it's not.

Speaker 2:

It's not about you. People aren't looking for you to fail. They want to hear what you have to say and you can leave a lasting impact. So it's not about you. People aren't looking for you to fail. They want to hear what you have to say and you can leave a lasting impact. So it's kind of that mindset shift of what can I give to the audience instead of where are they looking at me? What if I trip on a word? Like it's not about you as the speaker, it's about who you're delivering the message to. So that's helped a lot and you've provided a ton of value and awesome insight, so thank you so much for that. My last question for you, because I know we're running probably a little bit over time. I hope you're good for like another minute or two.

Speaker 3:

Yes, I'll be a couple minutes late to this call, not a problem.

Speaker 2:

Okay. So last question, real quick what advice would you give to any other entrepreneur out there listening?

Speaker 3:

Failure is a good thing. The most monumental change in my perspective of being an entrepreneur was failing. I failed. Okay, that was horrible. It feels terrible. That's it. I can keep going and keep moving forward. Yep, yes, you can. And so just fail quickly and move past it and keep going, just keep going, just keep going.

Speaker 2:

I love it. That's so valuable, so powerful. Tom, thank you so much for coming on, for hanging around a little bit late. This was an amazing conversation.

Speaker 3:

Where can people get in touch with you if they want to continue this conversation with you? Frackfinancecom, that's F-R-A-K-financecom, or Tom at frackfinancecom that's F-R-A-K. Financecom. Or Tom at frackfinancecom. And then you could follow me on LinkedIn at Tom Dillon, CFA.

Speaker 2:

Perfect, We'll put all of those links in the show notes so people can get in touch Again. Tom, really appreciate you coming on. Thank you so much.

Speaker 3:

Thank you for having me and thanks for everything you do for this community.

Speaker 2:

Thanks for tuning into this episode of CFO Chronicles the secrets behind success. I hope you found value in today's conversation. As we wrap up, I'd love for you to do two things. First, make sure to subscribe to this podcast so you don't miss any future episodes. If you enjoyed today's discussion, please rate and review the show. It helps others discover the insights we share here. Second, if you're ready to take your business to the next level and attract the high-end clients you deserve, head over to accountingleadsnowcom or click the link in the show notes to book your strategy. Call it's time to position yourself as the advisor your clients need. And don't forget you can connect with me on LinkedIn to stay up to date on what's happening in the world of accounting and financial growth. We've got exciting topics coming up, so stay tuned for the next episode of CFO Chronicles.

Speaker 1:

Until then, keep pushing forward. Your growth is just one strategic move away. Thanks for listening to CFO Chronicles the secrets behind success. We hope today's episode provided valuable strategies to help you attract more high-paying clients. Be sure to subscribe to help you attract more high paying clients. Be sure to subscribe, follow and share with fellow professionals. Connect with us on LinkedIn and leave a review or comment to join the conversation. Your feedback helps us bring you the best insights in finance and marketing. Until next time, keep striving for success and unlocking your business's potential.