Tom Dillon, CFA
@profithuntercfo
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Following
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Fractional CFO to the SMB community @frakfinance . Built a 7-figure consultancy; Multi-family CRE Investor - $3.3MM AUM
Chicago, IL
Joined March 2012
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Pinned Tweet
Our referral program is up and running.
If you’ve got potential leads within your network that can benefit from CFO, Bookkeeping or accounting.
We’ve got incentives
Let’s talk.
Easy side hustle if you are part of the SMB community:
Join our Referral Program 🤝
Get $$$ in two ways:
🤑 Each successful booked call
🤑 Each successful client
Let's chat if you know business owners within the 1-5M range that can benefit from fractional finance services
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@ShaneAParrish
Our finite amount of time here on earth is so insignificant to the grand timeline of the universe that we should be a lot nicer to one another. Conquering wealth or power are misguided goals. Great empires of the past are dust in wind today. Help others, not just yourself.
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@zebulgar
I am sorry, but as an Al language model, I don’t know what to say. I wasn’t expecting this to happen.
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I need help. We are considering adding a virtual assistant and want to ensure we hit the ground running. What do you utilize your VA for?
#va
#virtualassistant
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@Codie_Sanchez
Both have been valuable to me. It’s the people in the program that come from various business disciplines that open up your eyes and ears to new ways of thinking and approaching various situations. You don’t get that in your microcosm of building a business. It’s more like 4.2X
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Let me tell you about the first time I met
@sweatystartup
I flew out to Georgia and met him and his family at his country club 80% of the way through their round. I think I caught him on 15. It was a par four. And then we rolled into 16 par three.
If you wanna know what my
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@TripleNetInvest
Wild. Watched the rehab. It’s a beautiful building.
Someone’s going to clean up.
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Allow me to reintroduce myself.
For those that are new here, I'm a born and raised Chicagoan with Midwestern values - modest and hardworking.
Previously worked at an investment banking firm. Left to find fulfillment in entrepreneurship. I've found success helping the SMB
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@nickgraynews
I know this is not how you make friends but…
My dad and I both didn’t like the interior when we test drove them.
Everything seemed very cheap.
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How to spot a new entrepreneur:
- Gets logo - website - social media, before landing a single client.
How to spot a seasoned entrepreneur:
-Gets the first paying client asap, then the rest.. eventually.
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Secret Sauce:
Side hustles often lead to your dream job.
What's your side hustle?
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@RobertMSterling
Great analysis. There is chaos at times but fairly structured.
They may hate startup world with all the twists, turns, and uncertainty.
But the right ones would probably thrive beyond belief.
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It's a baby girl!
Today is a big day!
I'm finding out the gender of my firstborn and I couldn't be more excited.
I’m in camp baby girl, and my wife is in camp baby boy. I’m wearing pink, she’s wearing blue.
I’ll have a video of swinging a golf club exploding a ball with the color.
What’s your
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@sweatystartup
$40,000 spent on DoorDash?
That's a cool strategy for longevity.
Just 30 minutes of sun exposure and some grounding, and he's all set.
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@carkerpox
Why did you do this to me.
I was having such a pleasant day.
Will be up all night.
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@LeadershipAcad1
You can’t control the opinions of an employee. Nor should you. Your control is hire or fire…at least in some states with employee at will.
If you fired them for it would you be sued in a non employee at will state? If the answer is yes, then probably focus on their work
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@redwood_ryan_a
@SMB_Attorney
It is but when you look at the affordability vs income data it is actually true.
Incomes haven’t kept up like they need to.
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@MacConwell
What are the best communities for founders?
@MacConwell
solo founder tweet made me realize it is incumbent on me to find the support that’s missing typically built in with having a co-founder. Thanks for the help
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@for_yield
One person looks at this as a job.
Another looks at it as a catapult to leapfrog their peers in a strategic career move.
Massive opportunity to learn.
If I were young and interested in this field I’d jump on it.
You can always go back being a deal junkie at any CRE shop.
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@RealLifeRentals
3 options:
Logical
Payment plan. Financial troubles most likely. Ask for $100 a month.
Vindictive Pettiness
Rent to people he wouldn’t want to be around but respect the home and pay on time if no payments received.
Least Resistance
Hassle ratio probably doesn’t meet
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I think it’s about time I start talking about what I’ve done and what I’m doing. The midwest raised me to be modest. We’re told not to talk about your accomplishments, BUT on platforms like this that doesn’t seem to get you anywhere. So as uncomfortable as it is here we go:
As a
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I'm throwing a rooftop SMB owner & ETA meetup this Thursday.
Join other business owners, operators, and investors for great conversation & connection.
Ever wanted a peer group or just someone to bounce an idea off of before executing… well here you go.
👉 Comment below and
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@sweatystartup
And if they get discouraged by this, you're doing them a favor.
The real ones will use this as fuel just to prove you wrong.
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We’re going bankrupt.
These were the first words from my clients on the very first day of taking over.
They didn’t tell me how bad it was prior to agreeing to come in. Admittedly, they knew this wasn’t the right way to start out on the right foot. But I understood. They thought
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It's crazy how CFOs approve but ...
OGs accountants / CPAs hated it.
ANNOUNCEMENT: I made a website that’s Yelp for accountants:
I am looking for a new accountant. Finding one that’s good + fit my needs is hard and time consuming.
So, I tweeted out asking who has a good accountant.
• +150 people replied w/ an
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The mentor-mentee relationship is a mutual privilege.
One of my mentees shared with me one time:
"Once I started gaining traction, you really started caring."
My response: "No, I always cared. We just have a lot more to talk about now."
As the saying goes:
“When the student
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I feel like using sports to build rapport is like talking about the weather - it can be useful, but it's often just a crutch without much substance.
What other tactics do you use to build rapport?
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Are you intentionally cooking the books?
I just had to fire another bookkeeper on behalf of a client.
This one was earning $2,500 / month.
Claimed to have a masters in forensic accounting and was a CPA. Told me it was accrual accounting. As I continued asking questions, he
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Two types of people in this world.
One that loves eating in bed.
And one that despises a single crumb.
Do these two always marry each other?
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Sharing a concise cheat sheet on calculating crucial cash flow metrics. 💸
This is a useful guide for beginners or those refreshing their knowledge.
Interested in learning more about any of these?
Feel free to ask!
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Hey SMB owners & ETA enthusiasts!
Tomorrow evening, I’m hosting the Chicago SMB Meetup.
Starting at 5pm in the West Loop.
This is your chance to make REAL connections in a casual setting with local business owners, operators, and investors.
👉You must confirm your attendance.
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Most SMBs don't need a CFO.
What they really need is:
- Accurate data on time: a bookkeeper.
- Help with tax compliance: an accountant.
- Decision support based on that data: a Fractional CFO.
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@girdley
I find a lot of SMB owners trying to identify the perfect KPI.
Just start tracking and iterate.
Just don’t tie any comp to them until you’re sure.
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Today is a big day!
I'm finding out the gender of my firstborn and I couldn't be more excited.
I’m in camp baby girl, and my wife is in camp baby boy. I’m wearing pink, she’s wearing blue.
I’ll have a video of swinging a golf club exploding a ball with the color.
What’s your
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Working hard will always pay off.
There is no such thing as losing when you try.
When you take action:
• You get valuable expertise
• You get better at what you do
• You get closer to outcomes, whether right or wrong
The only way to lose is by not taking any action at
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@MarioNawfal
@RobertKennedyJr
@elonmusk
All a ploy to pull votes away from Trump. Smart. Not a political statement.
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Surrounding yourself with a supportive community can offer the encouragement needed to overcome every challenge you encounter.
That’s what I appreciate most about the SMB community.
What we achieve here, beyond all those vanity metrics we pursue, is truly powerful.
Sharing our
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@SMB_Attorney
They said the same thing about him during the dot com boom & bust. He'd do just fine.
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@realestatedude0
DAWGS + Private security once the valuable stuff gets put in until close. Only thing that works in Chicago.
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Don't wait until you hit a "certain level" to start doing things right.
If you are operating a business that has:
✓ Some sales
✓ Some employees
✓ Some clients
You can't afford to skip bookkeeping.
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I don't understand why some people want to retire early.
They seek freedom but often find a void of purpose.
A good day's work brings more than income; it brings a sense of fulfillment and contribution to society.
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Mondays have a whole new meaning for me now
Nothing aligns your priorities quite like expecting your first child.
We go through life's big milestones: marriage, career changes, launching new ventures...
But becoming a parent? It's unparalleled.
It’s like discovering a new
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What is the smartest investment for most SMBs?
-Build a robust cash reserve
You get a safety net that will help you:
1. Seize opportunities
2. Tackle unforeseen events
But most importantly:
-> You avoid unplanned investments.
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@dunkhippo33
Market-product fit is as much about the product function as it is about the problem narrative your selling a solution for. Iterate your sales pitch before iterating the product. It’s faster - about 1 day to do so. Talk to more customers, operative word, talk...don’t sell
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What does resilience mean to you?
I will start:
Persistent optimism and effort against adversity.
Your turn 👇
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@mhp_guy
Why do you wait or care….seems like a you problem. Enjoy the time with the people in front of you
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Just ran into this legend at my small business acquisition conference.
So kind to usher me in for a quick hello and handshake during his livestream promoting his new book - helping people build sales & social media brands.
Made my day
@garyvee
!
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For those wondering:
This is what month 1 of a fractional CFO looks like when fixing all the low hanging fruit in a business that's been doing it wrong for so long.
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If you are an entrepreneur, repeat after me:
- I don't have to do it all by myself.
- I'm not the mastermind of my business.
- I can delegate.
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@stkirsch
Provided your grave concern, I’m assuming you guys started blood bank groups? Find a handful of people who have same blood type and agree to share when needed if storage costs are too high. Is this direct donation in hospitals allowed even? Guess there is a new meaning to blood
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Your
#1
priority as an SMB owner:
Cash flow.
Ensure consistent liquidity and stability; this will help you solve any problem later.
Make the cash flow, learn to manage it, watch your business grow.
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Don't work smart until you're ready.
Some people get obsessed with working smart and end up complicating everything.
Always thinking about ways to get shortcuts instead of doing the actual work.
Embrace the grind, especially at the start of your journey.
Yes, you must work
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I’ve always had a hatred towards our education structure. I think it’s broken.
I’ve always been a proponent of pivoting to a new career, even if you are at the pinnacle of a great one.
I’m not saying every Michael Jordan should go play baseball, but I am saying a lot of Barry
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@dklineii
When I first saw the picture, I thought it was a story about Elon Musk 😆 Happy birthday, Dave!
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If you're serious about buying a business...
STOP just "reading" and "learning" about it.
• Another podcast won't make the difference
• Another webinar won't move you forward
You keep doing that just to feel better about your inaction.
True learning comes from doing, either
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March 2024, and yet:
Most old-school SMBs are still running on touch and feel.
They're not tracking any KPIs.
Not even the financial ones.
Why am I bringing this up? As a Fractional CFO, the impact of my work thrives on data.
This is a reminder for you: don't get trapped in
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@AmandaMGoetz
Totally agree with this. This is why I prefer doing activities like going fishing/hiking or others to meet people.
Meeting new people is beneficial in many ways, but the quality of the experience makes all the difference.
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Weekends are harsh for some entrepreneurs.
Those who think they didn't do well enough this week, month or that other day.
I have a message for you:
Stop undervaluing your progress.
Acknowledge your current achievements (even if it means just surviving the season)
Every step
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@RobertMSterling
Let's create a poll on X regarding whether you should keep it or not, and make your wife accept the results.
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@Twenty7Trades
@collin_ruth89
I wouldn’t say it’s beneath anyone but it’s certainly not a good use a time when someone competent can do it and therefore Collin can focus on more value creation activities.
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One of the best parts of being a fractional CFO is rescuing SMB owners from difficult situations and helping them get their businesses back on track.
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I'd like to remind you:
You don’t have to know it all from the beginning.
You just need steady baby steps in the right direction.
Just be consistent and it will soon lead you to your goal.
Success is a game you have to figure out.
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@pitdesi
All schools have to grade on a curve otherwise it crushes its students job prospects. Provided college degrees are more commonplace students compete on GPA to even get an interview.
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Chicago SMB owners & ETA enthusiasts: Today’s the day for revenge!
Tired of Zoom calls and Calendly links to meet people? This is your revenge for a day.
Join us for a rooftop meetup with fellow business owners, operators, and investors.
Whether you're looking to buy a
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@sweatystartup
Well a cost seg referral is coming your way. So tip the scale +1 for the nice side.
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I keep people in my life who I genuinely think are good people.
Everyone else has to go
It doesn’t matter what they can offer you.
Just cut ’em.
Implement this is your personal and professional life.
It will save you a lot of headache.
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Asking business owners... do you know your customer acquisition cost? your best traction channel? Have a plan if you lose your biggest client?
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It is very common to feel STUCK as a business owner.
And that, my friend, is entirely your fault.
Your reluctance to let go of certain tasks is costing you much more than you realize.
You're doing everything.
Managing multiple jobs is burning you out.
It seems like a good
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@lolitataub
It depends, like all things. My gut reaction is, run. My thoughtful reaction is, why are they asking for that and can they add value if the fund won’t invest. I’ve gotten this a lot at the Angel level but first im hearing of it at VC level.
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How to spot new entrepreneurs:
They treat their business as if it's going to last forever.
How to spot a seasoned entrepreneur:
They build their business as if they were to sell it from the beginning.
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Small wins are also wins.
Just hit the 1K mark on X, and my wonderful wife surprised me with this cupcake. It may be a small treat, but it shows I'm going in the right direction. She promised a bigger one for each new milestone.
To some, a goal like this might not seem worth
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If you're in Chicagoland and dealing with something similar, feel free to DM me. Let's grab a drink and talk!
Seeing many responses like this is breaking my heart and indicating that we have a serious problem.
You're not the only one. Shoot me a DM if this is you and you're in my area. I would love to connect!
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I don’t think this applies to just football but any team sport.
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Delegation is a key component for growth in SMBs.
Before considering delegation, it’s important to understand:
- The phase you’re in (Yes, you need a plan)
-How, when, and what to hire and delegate
Most say, "You'll know when you get there"
That's partially true; intuition
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@benkellyone
I’d throw each through the headache / profit ratio test.
Example: I would never want to build or buy a property management company unless I owned the underlying assets being managed.
It’s a horrific business to run - so many fire drills. The team turnover is high bc of this
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@ErnieBrownII
Bring up a Deconversion proposal during a condo building HOA meeting. Step back and watch the fireworks fly
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How you find out if you really like what you're doing?
Quite simple 👇
Tomorrow is Monday; you should have a plan to start and be excited about it.
How you feel about Mondays can reveal a lot about your relationship with your work.
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