April 24, 2025 • 30 mins
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.
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
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:01):
Welcome to CFO Chronicles the secrets behind
success the go-to podcast forfractional CFOs and accounting
firm owners who want to attractmore high-paying clients and
increase their revenue.
Hosted by James Donovan fromNine Two Media, this podcast
dives into marketing strategiesspecifically designed for lead
(00:22):
generation and clientacquisition.
In each episode, you'll hearfrom industry leaders sharing
their success stories, and TodayI am joined by Tom Dillon from
Frack Finance, based in Chicago.
Speaker 2 (00:50):
Tom, I know we were going back and forth a little
bit here before the recording.
I'm super excited to dive intoyour story, hear a little bit
more about you and for thelisteners to learn about you as
well.
So welcome to the show.
Speaker 3 (01:02):
Thank you.
Thank you for having us.
It's a pleasure to be here.
Speaker 2 (01:06):
Awesome.
I want to start off real quickbecause your background it's
showing a picture what lookslike a golf course.
You have a flag from one of thepins.
I would love to hear a littlebit about that golf course.
There must be some significantmeaning if that's hanging up in
your office.
Speaker 3 (01:23):
Yeah, so I couldn't normally blur that out, I
couldn't get the thing to uploadon zoom.
But yeah, that's um Arcadiabluffs Uh, it's where I got my
first hole in one.
Okay, so it's a.
It's a top public course up inMichigan, right on the bluffs on
Lake Michigan, and it's abeautiful course.
I would highly recommend it ifyou can get out there to play
(01:44):
that one for sure.
Speaker 2 (01:45):
Well, congratulations on the hole-in-one.
And you mentioned that waswhere you got your first one.
So how many hole-in-ones do youhave?
Don't have a second, that'sjust the first.
I'm hopeful that's awesome.
(02:06):
Well, hey, hole-in-one.
I'm not a great golfer by anystretch, but every time you get
up to the par three it's like istoday the day?
Is it gonna happen?
Speaker 3 (02:10):
so it's cool that that I know.
Isn't that the best feeling,especially heading to the
masters with everything kickingoff today.
I just get that, you get thatgood feeling.
That first birdie of the seasonyeah, it's coming.
So.
I'm super excited to kick offthe season, that's for sure
that's so.
Speaker 2 (02:25):
So, Tom, tell me a little bit about how you got
into becoming a fractional CFO.
Is this something that you knewgrowing up?
You're like I cannot wait to beolder and get into accounting
and work with numbers, or likemaybe it was.
How did you get to where youare now?
Speaker 3 (02:48):
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 thateveryone has to build towards,
and so everyone has a story, andI guess here's mine.
The original origin story ofhow the numbers and then I'll
get into more of the career wasI had tripped and fell on
success with selling Cutcocutlery and made a bunch of
(03:12):
money as an 18-year-old, and Ihad talked to my dad about what
I should do with it.
And he said maybe I'll try toget you a meeting with my wealth
manager and he'll sit down withyou.
And so I sat down with a guynamed Chris Crawley, who was at
Citibank at the time, and hetaught me the rule of 72.
And that's, if you divide theinterest rate into it, tells you
how long it'll take for yourmoney to double.
(03:33):
And immediately I was hooked,and so I knew I wasn't going to
go down any other profession butfinance.
And so that's what I did.
I up for, uh, for a financedegree, 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
(03:53):
quickly realize that there wasthis 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 thatprocess, it really became
apparent that I was going to godown this path.
But I also, being in finance,you're trained to be risk
(04:17):
adverse, and so I wanted tode-risk this you know, crazy,
jump out of the plane.
This, you know, crazy, jump outof the plane.
And and so, before kind ofdoing that, I wanted to make
sure that I had some experiencein what I called ops chops.
Really, all we did at, you know,the investment banking firm was
you're sitting in the ivorytower, you're pontificating
(04:38):
people's business decisions, butyou're not really making any of
your own.
I wasn't hiring, firing,managing people.
You're not really making any ofyour own.
I wasn't hiring, firing,managing people.
And so I knew I needed to getthat experience if I wanted to
be successful, and I had thisbig idea of you know I wanted to
change the world, and so,before doing that, I went and
got some experience.
I worked at a private equitybacked company as their CFO and
(05:00):
then was promoted to CEO, ranthat for a little bit and then
went back to school to startputting this idea through the
ringer and at the end of it, thenight of graduation, I raised
money for this idea and it was atech company that was going to
disrupt the market for orderingand payment at hospitality.
So this is pre-COVID, and we hada QR code based ordering and
(05:23):
payment system and we had asuccessful pilot and we were
launching to the public the weekCOVID hit.
So now we have a native app,both operating languages, which,
looking back, was a hugeexecution error, realized this
wasn't going to be sustainable,and so I fired myself
(05:44):
financially, not operationallyto keep the team together and
keep operating, which I'm suremany entrepreneurs have done dug
into credit cards just to getpayroll, and so in those moments
I realized man, I got to paythe bills.
How are we going to do this?
So I went back to my roots andstarted moonlighting as a
fractional CFO and so, 11 yearsago, going, we're going on 11
(06:06):
years now.
Um is when that started and atthe, at the, at the point in
time where you come to therealization that you're going to
have to swallow this painful,disgusting tasting pill of
failure, was the real kind of umentrance and commitment into
(06:26):
the fractional CFO space, and soit was born out of necessity
and then turned into a realpassion and love of mine.
Speaker 2 (06:33):
That's so good.
I mean.
Failure only happens when youquit, though, and it doesn't
sound like you've quit.
It sounds like you've just keptgoing and you've adapted and
you found a way to make it work.
So I wouldn't chalk this up asfailure 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 (06:56):
Yeah, that's awesome.
I appreciate that.
Yeah, I think it's only afailure if you don't learn from
it.
And so raising capital and youknow, and being a fiduciary,
having that fiduciary duty toyour shareholders, and and um,
it's tough, you know you're.
When you're a steward ofpeople's capital, it's a very
tough position to be in and um,and it's.
(07:17):
It sucks when you're, whenthings aren't going your way,
but it's the reality of mostentrepreneurs that do raise
venture capital face.
Speaker 2 (07:29):
Yeah, what do you find is one of the biggest
challenges that you're facing inthis season right now, or
something maybe in the last yearthat you face and you've
overcome where you're like youcan look back and be like, wow,
that was really hard and I'm sohappy I pushed through.
Speaker 3 (07:50):
So I would say it's the J curving of the business
model.
It's hiring ahead of growth.
I think is one of the mostchallenging things to do in
business and before we didn'tface this problem and I'm so
happy to be on here and loveeverything you do for this
community, james and part ofthat is the transition of going
(08:13):
from a one-man band and being atcapacity but cashflow is good,
and then having thatconversation with your wife
realizing I don't have atransferable asset, I'm going to
get burnt out.
I need to build a team.
Honey, we're going to becutting our margins in half.
Well, if they don't know, yoursignificant other doesn't know
what margins are, they're goingto quickly realize it means
(08:35):
you're going to have half thecash flow.
So that's ultimately what wedid here in the past six months
well, seven months, and thenwe're going to continue doing it
for the next five months, whichis J curving the business model
, hiring ahead of growth andcontinuing to look to build out
our pool of talent, our bench,where we are looking to bring
(08:58):
other fractionals on our teamand and develop them as well.
Speaker 2 (09:04):
Yeah, one of the intensives I was just at a
couple of months ago.
One of the speakers therereally successful marketing
company.
He's been doing it for 10 or 15, 15 years and he spoke about
that as well hiring ahead ofgrowth and the point he made
that really stuck with me.
So it's interesting you'rebringing this up.
Is that you're?
Speaker 1 (09:23):
always either overstaffed, or you're
understaffed.
Speaker 2 (09:26):
So you might as well be overstaffed, because if
you're in that sweet spot thatdoesn't really exist, it means
you're not growing.
And if you're in that sweetspot 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 toaccept, hearing that from
someone significantly moresuccessful, but that is the
(09:47):
reality.
And I think I look back at ourteam at times and I'm like, yeah
, I know we've been understaffedand it's tough and it kind of
makes everyone in a morepanicked state all the time
because you feel like you'rechasing your tail.
But on the other end of thespectrum, it's hard as the owner
to be like let's carry morepayroll than we technically need
right now all the time.
(10:07):
So how are you handling thatmentally, knowing like, hey, the
bills are just going to be moreexpensive on payroll.
We technically don't need thisperson right now?
Speaker 3 (10:21):
I have an abundance mindset, not a scarcity mindset,
and so for me, it's keeping thepositivity and knowing that
there's a lot of opportunitiesout there, because, as you know
the success and failure rates ofa lot of entrepreneurs people
need help, and for us, it's thesame thing that we do with our
(10:42):
clients, which is we're seeingkind of those micro traction
metrics of success.
It's those little wins that arebuilding upon each other that
encourage us to keep going, thatwe're heading down the right
direction.
But it's having a roadmap andbuilding a roadmap to do that.
And so for us, we're alwaysthinking about what are the
goals that you want to achieve?
(11:03):
Are you looking to sell yourcompany?
Are you looking to double thesize of your team?
Because that is the point ofcritical mass where you really
start to cover overhead andyou're earning the cashflow as a
business owner that you want indistributions and then reverse
engineering that.
How do we get there?
And where are the KPIs?
And what is our marketing?
James, you know better thananyone what's our marketing
(11:24):
funnel and then our conversionrate and sales, and really
focusing in on those KPIs andmaking sure that we're headed in
the right direction or makingthose tweaks in order to make
sure that we're moving andpulling the levers in the right
way.
Speaker 2 (11:39):
I love what you mentioned about the abundance
mindset, because that is so trueand a mentor of mine in the
past the analogy that was kindof 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 reallyopening up your hand, for that
abundance of more can come inand there's more available,
(12:02):
instead of kind of holding on toevery last dollar.
So, yeah, I really love thatyou're looking at it that way.
The other thing I'll add inhere is I don't know where my
business would be if I didn'tchoose to start working with
accountants and fractional CFOs,because I feel blessed, more
(12:24):
than other marketing companiesin a sense, or other business
owners, that I get to speak tofractional CFOs and accountants
and people who are so smart withmoney and strategic thinking
all the time Like to get thatinsight into the business that I
think a lot of people don'thave access to without hiring a
fractional CFO.
So that's been a massive stepfor me and I think our business
(12:48):
is growth.
What are some of the thingsthat you notice when you jump
into new clients where they'relike you, kind of see that penny
dropping moment or, like their,their brain just break when you
give them some information thatmight seem so basic to you 13
week cashflow is a big one andgiving visibility for a business
(13:12):
owner to feel comfortable thatmoney's going out but it's
coming back in, and havingpredictability around that.
Speaker 3 (13:20):
There's no better peace of mind and clarity.
It's very scary to makedecisions when it comes to your
personal cash in a void, cash ina void.
And so that, I think, is thenumber one aspect where kind of
not, it's not a light that goeson, it's more of well, it is,
(13:41):
it's more of a light goes on andnow I can see.
I can actually look and seewhere we're going, and not in
the dark.
And so those moments ofrealizing that I'm not in this
siloed echo chamber of decisionmaking, that I have a strategic
partner who's the financialadult in the room, who I can
(14:02):
bounce anything off of and getthe strategic insights of yeah,
we've been here before.
We understand this.
Here's a playbook on what'sbeen successful in the past is
super helpful.
The same thing with you whenyou talk to people in our
community, james.
You're like yep, on what's beensuccessful in the past is super
helpful.
The same thing with you whenyou talk to people in our
community, james.
You're like yep, we've beendown this path, I know it works,
let's, let's ride.
And so I think it's verysimilar there, and a lot of
(14:23):
times when you ask too about youknow how do you know if things
are going in the right direction?
For me personally, we we focuseda lot on our depth and
experience and we really leaninto that, and lean into it in a
heavy way, where we can'tservice clients in the right way
(14:44):
without having that experience.
And so continuing to grow ourbench and grow our experience
with new team members is reallyhow we continue to grow.
So having that abundancemindset, hiring added growth,
allows us to do just that, andso for the clients, it's kind of
the same thing.
It's really bringing that extralevel of experience that they
(15:07):
also they otherwise would nothave had on their team.
And those moments are wonderful, that they feel like they're
making the right decisions andthey've got someone in the room
who is checking to make surethat, financially, this is the
best and sound decision that's,I mean, one of the biggest
things I've noticed with withyour industry and the clients
(15:30):
we've worked with, theconversations we've had other
guests.
Speaker 2 (15:33):
You guys do such a good job at removing the emotion
from all the decision-makingand then it just makes it so
clear this is what the datatells us to do.
There's no emotion that goesbehind it, and emotional
decisions generally don't leadto good outcomes for the most
part, especially in business.
(15:54):
But yeah, you guys do such anamazing job at just like here's
the math.
Here's the numbers.
This is telling us what weshould do, but not every
business owner knows how to lookat the numbers in that way, so
it's pretty cool.
Speaker 3 (16:06):
We're not completely callous.
We do have emotions, but it's avery, very good point.
Removing them takes a lot ofeffort.
I think you have your physicalhealth and your financial health
, and if you look and talk witha lot of doctors, they're
trained to remove the emotionfrom the decisions of giving
that bad news or putting a pathin place to rectify the issues
(16:31):
and problems that someone hasfrom a health perspective.
I think it's the same thingthat somehow, along the way, is
ingrained in us and you do comea little, become a little
callous, but the emotions arestill there.
You just learn to move pastthem quicker, that's cool.
Speaker 2 (16:45):
Is your team all all in house or like sorry, in your
office, or do you have someremote workers as well?
What's the structure of yourteam look like?
Speaker 3 (16:56):
Yeah, so we're mostly remote.
We have three people here inChicago which is incredible
Bringing on a new CFO this week,which was just a wonderful yeah
, the best feeling you know.
Helping the clients, growingthe team those are the most
wonderful feelings you can haveas an entrepreneur.
And so what we really have inthree core services we do if
(17:22):
you're buying a business,growing a business or selling a
business.
So we really look at the lifecycle of growing a business or
selling a business.
So we really look at the lifecycle of the entirety of an SMB
owner, and so from thatperspective, our team is a
little diverse.
So we do have the bookkeeping,we do have the forensic
accountants that are doingquality of earnings, and then we
have our fractional CFOs thatare looking at growth and then,
(17:44):
obviously, m&a from a sell sideperspective, if companies are
looking to sell their company.
So our team's a little diverse.
It's not just fractionals.
Speaker 2 (17:52):
Yeah, that's cool.
What's been kind of yoursuccess recipe when it comes to
hiring talent or where do yousource talent?
Do you have any insight you'reable to share there?
Because I know a lot of otherfirms out there are also growing
and hiring and finding goodtalent is tough.
(18:12):
So what's been working well foryou?
Speaker 3 (18:16):
We look for people that have been kind of battle
tested, in the sense that haveeither worked with companies
that may have been distressed orin hyper growth mode that they
have been.
That cash has been a huge focusof theirs and it's been the
success of managing that cashappropriately for capital
(18:37):
allocation, resource allocation,that they have a proven track
record there and I think, justin terms of talking about it and
recruiting in that way, it'sled to an extremely strong team,
because if they understand thatyou get it, and if they've done
it before, they want to workwith a team that is equally as
(18:59):
strong and that's going to alsohelp add perspective.
Or, if there's an issue interms of different aspects,
someone might have not done anM&A deal before, but they've got
a client that wants to growthrough acquisition for
inorganic growth Great, you know, let's tap so-and-so, you know,
and so whatever that looks likein this scenario, you know
(19:21):
that's.
That's where I think kind ofyou are able to recruit.
The talent that you want is byoffering more resources to
people who are already highcaliber.
That's cool, that's awesome Tom.
Speaker 2 (19:34):
what are you guys doing at your firm to get new
clients interested in workingwith you or to get on the radar
of potential new clients?
How do you guys market?
Speaker 3 (19:47):
Yeah, so it's a great question.
So just two years ago is whenwe really branded ourselves and
it was just me as the one manband, and now we're shifting our
entire mindset to growing as ateam and focusing on the leads
and our marketing funnel andthen the sales conversion funnel
(20:08):
.
And I'm thrilled to have foundyou, james, because we're in the
process of going through thatas a firm of how can we improve
in this aspect, becauseoriginally it was just hey, I'm
at capacity, I get clients.
Now we're here and making greatcash flow and you don't really
(20:29):
have a concern because a lot ofthose easy wins are just from
referrals and going to a handfulof networking events.
But then it goes beyond thatonce you have a team and you
have to start feeding themachine consistently.
We're in the process oflearning a lot of that and we're
trying to expand and learn.
And so I was listening to allthese incredible guests that
you've had the past two days andit's just super impressive, all
(20:53):
the talent that's out there,and it's super impressive all
the people who are out thereassisting and helping this
community of fractionals andaccountants from that exact
angle.
For us, what's been working istrying to be an authority
getting on podcasts, gettinginto speaking engagements and
(21:15):
putting yourself out there.
And I think the only way toreally do that is, if you're
starting out and you're lookingto transition to becoming a
fractional CFO or an independentaccountant, and hang your own
shingle.
I think those, the early daysare maybe go work for another
firm, go learn best practices,get some clients, get some
(21:36):
experience, get battle tested.
Once you're going to bestepping out and going and
hanging your own shingle andworrying about you know that
business development aspect, youknow that's where you really
lean into those experiences andyou know terrible word but case
study.
But when you're speaking andyou're able to pull from those
(21:57):
experiences whether you're on apodcast, webinar or getting on
stage at a conference and youknow and being a value add
speaker to the audience, I thinkthat's really where you're able
to draw from.
And so, in terms of cadence ofhow do you get there and how do
you become an authority, if youfeel like you have imposter
syndrome, you're not alone.
(22:18):
Everyone that started had that.
You have to break through itwith getting experience.
One of the best ways is juststart doing and now you can draw
from those experiences, you canbe the authority of wait a
minute.
I remember when we did this fora client and that was super
successful.
Maybe this could help otherpeople.
Speaker 2 (22:38):
Tom is getting on podcasts, getting on stage.
Is that something that comesnatural to you, or did you have
to develop and level up intothis version of who you are
right now?
That something that comesnatural to you, or did you have
to develop and level up intothis version of who you are
right now?
Speaker 3 (22:57):
So I grew up with three brothers, so four boys in
the family.
We were pretty rambunctiousgroup of boys, so I think there
was some level ofcompetitiveness in there that's
constantly driving me andpushing me into probably the
uncomfortable.
I was the third in my familyand so you've got two older
brothers.
You're always trying to keep upwith where things were probably
(23:19):
always uncomfortable, where youreally just are pushing
yourself and trying to compete.
So innately there's, there'ssomething there inside that's
driving.
But from a perspective of youknow, do I love public speaking?
No, I don't think everyoneloves public speaking.
Have I gotten to the pointwhere the nervousness goes away?
(23:41):
Yeah, but that's all inpreparation and reps.
When I was thinking of coming onhere last night driving home
from Milwaukee at a networkingevent, um, I was thinking of
some amazing people that I metthere.
Um, I was also thinking aboutwhat I was going to say.
There was a little nervousnessthat pops in here.
You know, james has had theseamazing guests on.
(24:04):
How am I going to add value tohis community and his audience?
Um, I don't think that evergoes away, and so it's with
preparation and reps that youjust 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 thatit's helpful and it gives you a
(24:28):
clear picture of what you'retrying to convey to your
audience.
And there's still a ton of workto do.
I was listening to one of yourguests, ken, and I thought he
was just such an incrediblespeaker.
Speaker 2 (24:39):
Yeah, yeah, he's good Very well, and that's
motivating.
Speaker 3 (24:42):
It's like, okay, let's, let's get polished.
Like I was telling my wife, I'mlike man, one guest was
incredible, super well-spokenand so and there was tons of
them.
Just first one that came tomind.
It was one of the most morerecent ones.
So you know, I know that was along-winded answer to your
question.
That's great.
That's great.
Be helpful to those that are alittle bit more nervous, um, um,
(25:06):
that don't want to putthemselves out there.
Speaker 2 (25:09):
You're extremely well spoken.
So that's why I had to ask,because it seems like it just
comes off super natural andthat's why I was wondering if
this has always been like hey, Ican just jump in front of the
camera and speak, or if you'vekind of morphed into that
version.
And so that's a great answer.
I was the best man at afriend's wedding two summers ago
(25:29):
and I was so nervous to speakand give a presentation and my
friend told me he's like it'snot, and the way he presented it
to me really erased so much ofthe nerves that I'm going to try
to carry in to any talk and butit's not.
It's not about you.
People aren't looking for youto fail.
They want to hear what you haveto say and you can leave a
(25:52):
lasting impact.
So it's not about you.
People aren't looking for youto fail.
They want to hear what you haveto say and you can leave a
lasting impact.
So it's kind of that mindsetshift of what can I give to the
audience instead of where arethey looking at me?
What if I trip on a word?
Like it's not about you as thespeaker, it's about who you're
delivering the message to.
So that's helped a lot andyou've provided a ton of value
and awesome insight, so thankyou so much for that.
My last question for you,because I know we're running
(26:13):
probably a little bit over time.
I hope you're good for likeanother minute or two.
Speaker 3 (26:18):
Yes, I'll be a couple minutes late to this call, not
a problem.
Speaker 2 (26:22):
Okay.
So last question, real quickwhat advice would you give to
any other entrepreneur out therelistening?
Speaker 3 (26:39):
Failure is a good thing.
The most monumental change inmy perspective of being an
entrepreneur was failing.
I failed.
Okay, that was horrible.
It feels terrible.
That's it.
I can keep going and keepmoving forward.
(27:01):
Yep, yes, you can.
And so just fail quickly andmove past it and keep going,
just keep going, just keep going.
Speaker 2 (27:10):
I love it.
That's so valuable, so powerful.
Tom, thank you so much forcoming on, for hanging around a
little bit late.
This was an amazingconversation.
Speaker 3 (27:24):
Where can people get in touch with you if they want
to continue this conversationwith you?
Frackfinancecom, that'sF-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 onLinkedIn at Tom Dillon, CFA.
Speaker 2 (27:35):
Perfect, We'll put all of those links in the show
notes so people can get in touchAgain.
Tom, really appreciate youcoming on.
Thank you so much.
Speaker 3 (27:42):
Thank you for having me and thanks for everything you
do for this community.
Speaker 2 (27:44):
Thanks for tuning into this episode of CFO
Chronicles the secrets behindsuccess.
I hope you found value intoday's conversation.
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(28:08):
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We've got exciting topicscoming up, so stay tuned for the
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Speaker 1 (28:36):
Until then, keep pushing forward.
Your growth is just onestrategic move away.
Thanks for listening to CFOChronicles the secrets behind
success.
We hope today's episodeprovided valuable strategies to
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(28:56):
Your feedback helps us bringyou the best insights in finance
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Until next time, keep strivingfor success and unlocking your
business's potential.
Welcome to CFO Chronicles the secrets behind
success the go-to podcast forfractional CFOs and accounting
firm owners who want to attractmore high-paying clients and
increase their revenue.
Hosted by James Donovan fromNine Two Media, this podcast
dives into marketing strategiesspecifically designed for lead
(00:22):
generation and clientacquisition.
In each episode, you'll hearfrom industry leaders sharing
their success stories, and TodayI am joined by Tom Dillon from
Frack Finance, based in Chicago.
Speaker 2 (00:50):
Tom, I know we were going back and forth a little
bit here before the recording.
I'm super excited to dive intoyour story, hear a little bit
more about you and for thelisteners to learn about you as
well.
So welcome to the show.
Speaker 3 (01:02):
Thank you.
Thank you for having us.
It's a pleasure to be here.
Speaker 2 (01:06):
Awesome.
I want to start off real quickbecause your background it's
showing a picture what lookslike a golf course.
You have a flag from one of thepins.
I would love to hear a littlebit about that golf course.
There must be some significantmeaning if that's hanging up in
your office.
Speaker 3 (01:23):
Yeah, so I couldn't normally blur that out, I
couldn't get the thing to uploadon zoom.
But yeah, that's um Arcadiabluffs Uh, it's where I got my
first hole in one.
Okay, so it's a.
It's a top public course up inMichigan, right on the bluffs on
Lake Michigan, and it's abeautiful course.
I would highly recommend it ifyou can get out there to play
(01:44):
that one for sure.
Speaker 2 (01:45):
Well, congratulations on the hole-in-one.
And you mentioned that waswhere you got your first one.
So how many hole-in-ones do youhave?
Don't have a second, that'sjust the first.
I'm hopeful that's awesome.
(02:06):
Well, hey, hole-in-one.
I'm not a great golfer by anystretch, but every time you get
up to the par three it's like istoday the day?
Is it gonna happen?
Speaker 3 (02:10):
so it's cool that that I know.
Isn't that the best feeling,especially heading to the
masters with everything kickingoff today.
I just get that, you get thatgood feeling.
That first birdie of the seasonyeah, it's coming.
So.
I'm super excited to kick offthe season, that's for sure
that's so.
Speaker 2 (02:25):
So, Tom, tell me a little bit about how you got
into becoming a fractional CFO.
Is this something that you knewgrowing up?
You're like I cannot wait to beolder and get into accounting
and work with numbers, or likemaybe it was.
How did you get to where youare now?
Speaker 3 (02:48):
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 thateveryone has to build towards,
and so everyone has a story, andI guess here's mine.
The original origin story ofhow the numbers and then I'll
get into more of the career wasI had tripped and fell on
success with selling Cutcocutlery and made a bunch of
(03:12):
money as an 18-year-old, and Ihad talked to my dad about what
I should do with it.
And he said maybe I'll try toget you a meeting with my wealth
manager and he'll sit down withyou.
And so I sat down with a guynamed Chris Crawley, who was at
Citibank at the time, and hetaught me the rule of 72.
And that's, if you divide theinterest rate into it, tells you
how long it'll take for yourmoney to double.
(03:33):
And immediately I was hooked,and so I knew I wasn't going to
go down any other profession butfinance.
And so that's what I did.
I up for, uh, for a financedegree, 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
(03:53):
quickly realize that there wasthis 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 thatprocess, it really became
apparent that I was going to godown this path.
But I also, being in finance,you're trained to be risk
(04:17):
adverse, and so I wanted tode-risk this you know, crazy,
jump out of the plane.
This, you know, crazy, jump outof the plane.
And and so, before kind ofdoing that, I wanted to make
sure that I had some experiencein what I called ops chops.
Really, all we did at, you know,the investment banking firm was
you're sitting in the ivorytower, you're pontificating
(04:38):
people's business decisions, butyou're not really making any of
your own.
I wasn't hiring, firing,managing people.
You're not really making any ofyour own.
I wasn't hiring, firing,managing people.
And so I knew I needed to getthat experience if I wanted to
be successful, and I had thisbig idea of you know I wanted to
change the world, and so,before doing that, I went and
got some experience.
I worked at a private equitybacked company as their CFO and
(05:00):
then was promoted to CEO, ranthat for a little bit and then
went back to school to startputting this idea through the
ringer and at the end of it, thenight of graduation, I raised
money for this idea and it was atech company that was going to
disrupt the market for orderingand payment at hospitality.
So this is pre-COVID, and we hada QR code based ordering and
(05:23):
payment system and we had asuccessful pilot and we were
launching to the public the weekCOVID hit.
So now we have a native app,both operating languages, which,
looking back, was a hugeexecution error, realized this
wasn't going to be sustainable,and so I fired myself
(05:44):
financially, not operationallyto keep the team together and
keep operating, which I'm suremany entrepreneurs have done dug
into credit cards just to getpayroll, and so in those moments
I realized man, I got to paythe bills.
How are we going to do this?
So I went back to my roots andstarted moonlighting as a
fractional CFO and so, 11 yearsago, going, we're going on 11
(06:06):
years now.
Um is when that started and atthe, at the, at the point in
time where you come to therealization that you're going to
have to swallow this painful,disgusting tasting pill of
failure, was the real kind of umentrance and commitment into
(06:26):
the fractional CFO space, and soit was born out of necessity
and then turned into a realpassion and love of mine.
Speaker 2 (06:33):
That's so good.
I mean.
Failure only happens when youquit, though, and it doesn't
sound like you've quit.
It sounds like you've just keptgoing and you've adapted and
you found a way to make it work.
So I wouldn't chalk this up asfailure 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 (06:56):
Yeah, that's awesome.
I appreciate that.
Yeah, I think it's only afailure if you don't learn from
it.
And so raising capital and youknow, and being a fiduciary,
having that fiduciary duty toyour shareholders, and and um,
it's tough, you know you're.
When you're a steward ofpeople's capital, it's a very
tough position to be in and um,and it's.
(07:17):
It sucks when you're, whenthings aren't going your way,
but it's the reality of mostentrepreneurs that do raise
venture capital face.
Speaker 2 (07:29):
Yeah, what do you find is one of the biggest
challenges that you're facing inthis season right now, or
something maybe in the last yearthat you face and you've
overcome where you're like youcan look back and be like, wow,
that was really hard and I'm sohappy I pushed through.
Speaker 3 (07:50):
So I would say it's the J curving of the business
model.
It's hiring ahead of growth.
I think is one of the mostchallenging things to do in
business and before we didn'tface this problem and I'm so
happy to be on here and loveeverything you do for this
community, james and part ofthat is the transition of going
(08:13):
from a one-man band and being atcapacity but cashflow is good,
and then having thatconversation with your wife
realizing I don't have atransferable asset, I'm going to
get burnt out.
I need to build a team.
Honey, we're going to becutting our margins in half.
Well, if they don't know, yoursignificant other doesn't know
what margins are, they're goingto quickly realize it means
(08:35):
you're going to have half thecash flow.
So that's ultimately what wedid here in the past six months
well, seven months, and thenwe're going to continue doing it
for the next five months, whichis J curving the business model
, hiring ahead of growth andcontinuing to look to build out
our pool of talent, our bench,where we are looking to bring
(08:58):
other fractionals on our teamand and develop them as well.
Speaker 2 (09:04):
Yeah, one of the intensives I was just at a
couple of months ago.
One of the speakers therereally successful marketing
company.
He's been doing it for 10 or 15, 15 years and he spoke about
that as well hiring ahead ofgrowth and the point he made
that really stuck with me.
So it's interesting you'rebringing this up.
Is that you're?
Speaker 1 (09:23):
always either overstaffed, or you're
understaffed.
Speaker 2 (09:26):
So you might as well be overstaffed, because if
you're in that sweet spot thatdoesn't really exist, it means
you're not growing.
And if you're in that sweetspot 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 toaccept, hearing that from
someone significantly moresuccessful, but that is the
(09:47):
reality.
And I think I look back at ourteam at times and I'm like, yeah
, I know we've been understaffedand it's tough and it kind of
makes everyone in a morepanicked state all the time
because you feel like you'rechasing your tail.
But on the other end of thespectrum, it's hard as the owner
to be like let's carry morepayroll than we technically need
right now all the time.
(10:07):
So how are you handling thatmentally, knowing like, hey, the
bills are just going to be moreexpensive on payroll.
We technically don't need thisperson right now?
Speaker 3 (10:21):
I have an abundance mindset, not a scarcity mindset,
and so for me, it's keeping thepositivity and knowing that
there's a lot of opportunitiesout there, because, as you know
the success and failure rates ofa lot of entrepreneurs people
need help, and for us, it's thesame thing that we do with our
(10:42):
clients, which is we're seeingkind of those micro traction
metrics of success.
It's those little wins that arebuilding upon each other that
encourage us to keep going, thatwe're heading down the right
direction.
But it's having a roadmap andbuilding a roadmap to do that.
And so for us, we're alwaysthinking about what are the
goals that you want to achieve?
(11:03):
Are you looking to sell yourcompany?
Are you looking to double thesize of your team?
Because that is the point ofcritical mass where you really
start to cover overhead andyou're earning the cashflow as a
business owner that you want indistributions and then reverse
engineering that.
How do we get there?
And where are the KPIs?
And what is our marketing?
James, you know better thananyone what's our marketing
(11:24):
funnel and then our conversionrate and sales, and really
focusing in on those KPIs andmaking sure that we're headed in
the right direction or makingthose tweaks in order to make
sure that we're moving andpulling the levers in the right
way.
Speaker 2 (11:39):
I love what you mentioned about the abundance
mindset, because that is so trueand a mentor of mine in the
past the analogy that was kindof 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 reallyopening up your hand, for that
abundance of more can come inand there's more available,
(12:02):
instead of kind of holding on toevery last dollar.
So, yeah, I really love thatyou're looking at it that way.
The other thing I'll add inhere is I don't know where my
business would be if I didn'tchoose to start working with
accountants and fractional CFOs,because I feel blessed, more
(12:24):
than other marketing companiesin a sense, or other business
owners, that I get to speak tofractional CFOs and accountants
and people who are so smart withmoney and strategic thinking
all the time Like to get thatinsight into the business that I
think a lot of people don'thave access to without hiring a
fractional CFO.
So that's been a massive stepfor me and I think our business
(12:48):
is growth.
What are some of the thingsthat you notice when you jump
into new clients where they'relike you, kind of see that penny
dropping moment or, like their,their brain just break when you
give them some information thatmight seem so basic to you 13
week cashflow is a big one andgiving visibility for a business
(13:12):
owner to feel comfortable thatmoney's going out but it's
coming back in, and havingpredictability around that.
Speaker 3 (13:20):
There's no better peace of mind and clarity.
It's very scary to makedecisions when it comes to your
personal cash in a void, cash ina void.
And so that, I think, is thenumber one aspect where kind of
not, it's not a light that goeson, it's more of well, it is,
(13:41):
it's more of a light goes on andnow I can see.
I can actually look and seewhere we're going, and not in
the dark.
And so those moments ofrealizing that I'm not in this
siloed echo chamber of decisionmaking, that I have a strategic
partner who's the financialadult in the room, who I can
(14:02):
bounce anything off of and getthe strategic insights of yeah,
we've been here before.
We understand this.
Here's a playbook on what'sbeen successful in the past is
super helpful.
The same thing with you whenyou talk to people in our
community, james.
You're like yep, on what's beensuccessful in the past is super
helpful.
The same thing with you whenyou talk to people in our
community, james.
You're like yep, we've beendown this path, I know it works,
let's, let's ride.
And so I think it's verysimilar there, and a lot of
(14:23):
times when you ask too about youknow how do you know if things
are going in the right direction?
For me personally, we we focuseda lot on our depth and
experience and we really leaninto that, and lean into it in a
heavy way, where we can'tservice clients in the right way
(14:44):
without having that experience.
And so continuing to grow ourbench and grow our experience
with new team members is reallyhow we continue to grow.
So having that abundancemindset, hiring added growth,
allows us to do just that, andso for the clients, it's kind of
the same thing.
It's really bringing that extralevel of experience that they
(15:07):
also they otherwise would nothave had on their team.
And those moments are wonderful, that they feel like they're
making the right decisions andthey've got someone in the room
who is checking to make surethat, financially, this is the
best and sound decision that's,I mean, one of the biggest
things I've noticed with withyour industry and the clients
(15:30):
we've worked with, theconversations we've had other
guests.
Speaker 2 (15:33):
You guys do such a good job at removing the emotion
from all the decision-makingand then it just makes it so
clear this is what the datatells us to do.
There's no emotion that goesbehind it, and emotional
decisions generally don't leadto good outcomes for the most
part, especially in business.
(15:54):
But yeah, you guys do such anamazing job at just like here's
the math.
Here's the numbers.
This is telling us what weshould do, but not every
business owner knows how to lookat the numbers in that way, so
it's pretty cool.
Speaker 3 (16:06):
We're not completely callous.
We do have emotions, but it's avery, very good point.
Removing them takes a lot ofeffort.
I think you have your physicalhealth and your financial health
, and if you look and talk witha lot of doctors, they're
trained to remove the emotionfrom the decisions of giving
that bad news or putting a pathin place to rectify the issues
(16:31):
and problems that someone hasfrom a health perspective.
I think it's the same thingthat somehow, along the way, is
ingrained in us and you do comea little, become a little
callous, but the emotions arestill there.
You just learn to move pastthem quicker, that's cool.
Speaker 2 (16:45):
Is your team all all in house or like sorry, in your
office, or do you have someremote workers as well?
What's the structure of yourteam look like?
Speaker 3 (16:56):
Yeah, so we're mostly remote.
We have three people here inChicago which is incredible
Bringing on a new CFO this week,which was just a wonderful yeah
, the best feeling you know.
Helping the clients, growingthe team those are the most
wonderful feelings you can haveas an entrepreneur.
And so what we really have inthree core services we do if
(17:22):
you're buying a business,growing a business or selling a
business.
So we really look at the lifecycle of growing a business or
selling a business.
So we really look at the lifecycle of the entirety of an SMB
owner, and so from thatperspective, our team is a
little diverse.
So we do have the bookkeeping,we do have the forensic
accountants that are doingquality of earnings, and then we
have our fractional CFOs thatare looking at growth and then,
(17:44):
obviously, m&a from a sell sideperspective, if companies are
looking to sell their company.
So our team's a little diverse.
It's not just fractionals.
Speaker 2 (17:52):
Yeah, that's cool.
What's been kind of yoursuccess recipe when it comes to
hiring talent or where do yousource talent?
Do you have any insight you'reable to share there?
Because I know a lot of otherfirms out there are also growing
and hiring and finding goodtalent is tough.
(18:12):
So what's been working well foryou?
Speaker 3 (18:16):
We look for people that have been kind of battle
tested, in the sense that haveeither worked with companies
that may have been distressed orin hyper growth mode that they
have been.
That cash has been a huge focusof theirs and it's been the
success of managing that cashappropriately for capital
(18:37):
allocation, resource allocation,that they have a proven track
record there and I think, justin terms of talking about it and
recruiting in that way, it'sled to an extremely strong team,
because if they understand thatyou get it, and if they've done
it before, they want to workwith a team that is equally as
(18:59):
strong and that's going to alsohelp add perspective.
Or, if there's an issue interms of different aspects,
someone might have not done anM&A deal before, but they've got
a client that wants to growthrough acquisition for
inorganic growth Great, you know, let's tap so-and-so, you know,
and so whatever that looks likein this scenario, you know
(19:21):
that's.
That's where I think kind ofyou are able to recruit.
The talent that you want is byoffering more resources to
people who are already highcaliber.
That's cool, that's awesome Tom.
Speaker 2 (19:34):
what are you guys doing at your firm to get new
clients interested in workingwith you or to get on the radar
of potential new clients?
How do you guys market?
Speaker 3 (19:47):
Yeah, so it's a great question.
So just two years ago is whenwe really branded ourselves and
it was just me as the one manband, and now we're shifting our
entire mindset to growing as ateam and focusing on the leads
and our marketing funnel andthen the sales conversion funnel
(20:08):
.
And I'm thrilled to have foundyou, james, because we're in the
process of going through thatas a firm of how can we improve
in this aspect, becauseoriginally it was just hey, I'm
at capacity, I get clients.
Now we're here and making greatcash flow and you don't really
(20:29):
have a concern because a lot ofthose easy wins are just from
referrals and going to a handfulof networking events.
But then it goes beyond thatonce you have a team and you
have to start feeding themachine consistently.
We're in the process oflearning a lot of that and we're
trying to expand and learn.
And so I was listening to allthese incredible guests that
you've had the past two days andit's just super impressive, all
(20:53):
the talent that's out there,and it's super impressive all
the people who are out thereassisting and helping this
community of fractionals andaccountants from that exact
angle.
For us, what's been working istrying to be an authority
getting on podcasts, gettinginto speaking engagements and
(21:15):
putting yourself out there.
And I think the only way toreally do that is, if you're
starting out and you're lookingto transition to becoming a
fractional CFO or an independentaccountant, and hang your own
shingle.
I think those, the early daysare maybe go work for another
firm, go learn best practices,get some clients, get some
(21:36):
experience, get battle tested.
Once you're going to bestepping out and going and
hanging your own shingle andworrying about you know that
business development aspect, youknow that's where you really
lean into those experiences andyou know terrible word but case
study.
But when you're speaking andyou're able to pull from those
(21:57):
experiences whether you're on apodcast, webinar or getting on
stage at a conference and youknow and being a value add
speaker to the audience, I thinkthat's really where you're able
to draw from.
And so, in terms of cadence ofhow do you get there and how do
you become an authority, if youfeel like you have imposter
syndrome, you're not alone.
(22:18):
Everyone that started had that.
You have to break through itwith getting experience.
One of the best ways is juststart doing and now you can draw
from those experiences, you canbe the authority of wait a
minute.
I remember when we did this fora client and that was super
successful.
Maybe this could help otherpeople.
Speaker 2 (22:38):
Tom is getting on podcasts, getting on stage.
Is that something that comesnatural to you, or did you have
to develop and level up intothis version of who you are
right now?
That something that comesnatural to you, or did you have
to develop and level up intothis version of who you are
right now?
Speaker 3 (22:57):
So I grew up with three brothers, so four boys in
the family.
We were pretty rambunctiousgroup of boys, so I think there
was some level ofcompetitiveness in there that's
constantly driving me andpushing me into probably the
uncomfortable.
I was the third in my familyand so you've got two older
brothers.
You're always trying to keep upwith where things were probably
(23:19):
always uncomfortable, where youreally just are pushing
yourself and trying to compete.
So innately there's, there'ssomething there inside that's
driving.
But from a perspective of youknow, do I love public speaking?
No, I don't think everyoneloves public speaking.
Have I gotten to the pointwhere the nervousness goes away?
(23:41):
Yeah, but that's all inpreparation and reps.
When I was thinking of coming onhere last night driving home
from Milwaukee at a networkingevent, um, I was thinking of
some amazing people that I metthere.
Um, I was also thinking aboutwhat I was going to say.
There was a little nervousnessthat pops in here.
You know, james has had theseamazing guests on.
(24:04):
How am I going to add value tohis community and his audience?
Um, I don't think that evergoes away, and so it's with
preparation and reps that youjust 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 thatit's helpful and it gives you a
(24:28):
clear picture of what you'retrying to convey to your
audience.
And there's still a ton of workto do.
I was listening to one of yourguests, ken, and I thought he
was just such an incrediblespeaker.
Speaker 2 (24:39):
Yeah, yeah, he's good Very well, and that's
motivating.
Speaker 3 (24:42):
It's like, okay, let's, let's get polished.
Like I was telling my wife, I'mlike man, one guest was
incredible, super well-spokenand so and there was tons of
them.
Just first one that came tomind.
It was one of the most morerecent ones.
So you know, I know that was along-winded answer to your
question.
That's great.
That's great.
Be helpful to those that are alittle bit more nervous, um, um,
(25:06):
that don't want to putthemselves out there.
Speaker 2 (25:09):
You're extremely well spoken.
So that's why I had to ask,because it seems like it just
comes off super natural andthat's why I was wondering if
this has always been like hey, Ican just jump in front of the
camera and speak, or if you'vekind of morphed into that
version.
And so that's a great answer.
I was the best man at afriend's wedding two summers ago
(25:29):
and I was so nervous to speakand give a presentation and my
friend told me he's like it'snot, and the way he presented it
to me really erased so much ofthe nerves that I'm going to try
to carry in to any talk and butit's not.
It's not about you.
People aren't looking for youto fail.
They want to hear what you haveto say and you can leave a
(25:52):
lasting impact.
So it's not about you.
People aren't looking for youto fail.
They want to hear what you haveto say and you can leave a
lasting impact.
So it's kind of that mindsetshift of what can I give to the
audience instead of where arethey looking at me?
What if I trip on a word?
Like it's not about you as thespeaker, it's about who you're
delivering the message to.
So that's helped a lot andyou've provided a ton of value
and awesome insight, so thankyou so much for that.
My last question for you,because I know we're running
(26:13):
probably a little bit over time.
I hope you're good for likeanother minute or two.
Speaker 3 (26:18):
Yes, I'll be a couple minutes late to this call, not
a problem.
Speaker 2 (26:22):
Okay.
So last question, real quickwhat advice would you give to
any other entrepreneur out therelistening?
Speaker 3 (26:39):
Failure is a good thing.
The most monumental change inmy perspective of being an
entrepreneur was failing.
I failed.
Okay, that was horrible.
It feels terrible.
That's it.
I can keep going and keepmoving forward.
(27:01):
Yep, yes, you can.
And so just fail quickly andmove past it and keep going,
just keep going, just keep going.
Speaker 2 (27:10):
I love it.
That's so valuable, so powerful.
Tom, thank you so much forcoming on, for hanging around a
little bit late.
This was an amazingconversation.
Speaker 3 (27:24):
Where can people get in touch with you if they want
to continue this conversationwith you?
Frackfinancecom, that'sF-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 onLinkedIn at Tom Dillon, CFA.
Speaker 2 (27:35):
Perfect, We'll put all of those links in the show
notes so people can get in touchAgain.
Tom, really appreciate youcoming on.
Thank you so much.
Speaker 3 (27:42):
Thank you for having me and thanks for everything you
do for this community.
Speaker 2 (27:44):
Thanks for tuning into this episode of CFO
Chronicles the secrets behindsuccess.
I hope you found value intoday's conversation.
As we wrap up, I'd love for youto do two things.
First, make sure to subscribeto this podcast so you don't
miss any future episodes.
If you enjoyed today'sdiscussion, please rate and
review the show.
It helps others discover theinsights we share here.
Second, if you're ready to takeyour business to the next level
(28:08):
and attract the high-endclients you deserve, head over
to accountingleadsnowcom orclick the link in the show notes
to book your strategy.
Call it's time to positionyourself as the advisor your
clients need.
And don't forget you canconnect with me on LinkedIn to
stay up to date on what'shappening in the world of
accounting and financial growth.
We've got exciting topicscoming up, so stay tuned for the
next episode of CFO Chronicles.
Speaker 1 (28:36):
Until then, keep pushing forward.
Your growth is just onestrategic move away.
Thanks for listening to CFOChronicles the secrets behind
success.
We hope today's episodeprovided valuable strategies to
help you attract morehigh-paying clients.
Be sure to subscribe to helpyou attract more high paying
clients.
Be sure to subscribe, followand share with fellow
professionals.
Connect with us on LinkedIn andleave a review or comment to
join the conversation.
(28:56):
Your feedback helps us bringyou the best insights in finance
and marketing.
Until next time, keep strivingfor success and unlocking your
business's potential.
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