Over the past decade, I've built three multimillion-dollar businesses while growing a family and raising four children.

I started with no resources, no connections, and didn’t have access to the playbooks that would have made the journey 10X easier. 

As a kid, I made money garden landscaping for families at church, manufacturing merchandise for private clubs, and then developing websites and running ad campaigns for local companies.

By 21, I was founding companies. In the decade since, I've:

➤ Generated $300M+ in revenue
➤ Built operations in 1,000+ U.S. cities
➤ Served over 3 million customers globally
➤ Helped grow hundreds of small businesses
➤ Raised $30M+ in capital from Angels, VCs, Private Equity, and Family Offices
➤ Successfully navigated both successful and failed multimillion-dollar acquisitions
➤ Been featured in leading publications like Forbes, Bloomberg, Entrepreneur, USA Today and more
➤ Worked with and advised the world's most iconic brands, including Diageo, Mars, Tesco, 7-Eleven, AB-InBev, Molson Coors, and Constellation

BUT, the journey was hard (harder than it needed to be).

I’ve faced many of the things you don't think about when starting a company:

→ Fought off (and won) predatory lawsuits
→ Closed a Seed round days after my wedding
→ Negotiated with demanding government agencies
→ Worked with lobbyists to introduce or change legislation
→ Raised a Series A while in the hospital for my first son's birth
→ Navigated a failed multi-million dollar merger while my daughter was born
→ Survived near-extinction events where we had single-digit weeks or days to save the company

Personal interests: Boxing, strength training, being in the ocean, spending quality time with my wife Danielle and our four little ones.

———

👋 Follow me for daily tips on mindset, systems, lifestyle design, and high-growth habits.

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Chris Vaughn

Fractional CFO for SMBs

If you're here, it's probably because you've recognized a problem with your business finances or you’re looking to scale and grow your operations and seeking solutions.

I hope I can be helpful and have the opportunity to add value to your business.

I believe you don't need to be a big company to benefit from a fractional CFO. Proper guidance is what sets most businesses up for success.

Whether you started from scratch, just acquired a business, have been operating for years, or are still searching, getting expert help for financial consultancy is always the right choice.

It is better to move with certainty than hope when you’re doing business and that's the essence of the fractional finance movement: delivering impact to specific problems business owners face without the long term commitment.

How can I help you? 

I specialize in SMBs, SaaS, and Ecommerce.

Here are my most common services:

-Fractional CFO Advisory
-Bookkeeping
-Accounting & Audit Readiness
-M&A & Valuation
-Human Resources
-Risk Advisory
-Tax Strategy

𝐍𝐞𝐱𝐭 𝐬𝐭𝐞𝐩?

Schedule a Complimentary 15-Minute consultation at www.calendly.com/tom-ihk/intro

Tom Dillon, CFA

The cash leak nobody talks about: timing.

I’ve sat in on too many calls that start the same way:

“We’re profitable… so why does payroll feel tight every other week?”

Because your P&L doesn’t pay bills. Your bank account does. And the calendar decides when that bank account gets funded.

Here’s the pattern I see in real businesses (especially services and agencies):

- You get paid in 45–60 days
- Payroll hits every 14 days
- Vendors want cash in 15–30 days
- Taxes and annual software renewals land on fixed dates

Nothing mystical is happening. Your cash cycle just doesn’t match your payment cycle.

When I diagnose this with a new client, I look for three timing gaps:

1. Collections lag vs payroll cadence
If customers pay monthly but payroll is biweekly, cash pressure shows up even with healthy margins.

2. Payables discipline
Paying suppliers early feels responsible. It can also quietly squeeze working capital.

3. “Lumpy” expenses treated like surprises
Taxes, insurance, annual renewals, equipment, and one-off contractors. Predictable costs that rarely get planned properly.

What fixes it isn’t a motivational speech. It’s mechanics:

- A rolling 13-week cash forecast reviewed weekly (not monthly)
- Invoicing habits that shorten time-to-cash (invoice fast, make payment easy, follow up on a schedule)
- Clear rules for when money leaves the account (due date, not whoever emails the most)
- A payroll + tax buffer you don’t touch

You can be profitable and still feel cash-stressed. That doesn’t mean you need more revenue first. It means your timing is working against you.

If you had to fix one thing this month, what would it be: collections, vendor terms, or surprise expenses?

#cash #finance

Most business owners I talk to are still waiting for interest rates to “go back to normal.”

If by “normal” you mean 0–3%…

That was the anomaly.

Cheap money is not the baseline. It’s the exception.

Here’s the clean version of 70 years of U.S. rates and why it matters to your decisions in 2026:

The 1950s–60s: rates were relatively calm because inflation was calm.

Growth and productivity did the heavy lifting.

The 1970s: inflation broke trust.

When inflation expectations reset higher, rates eventually had to follow.

The early 1980s: Volcker forced the reset with extreme policy.

Rates went high enough to crush inflation expectations. Pain was the mechanism.

The 1990s–2000s: every crisis reinforced a pattern.

Trouble shows up → rates come down.

2008–2021: “temporary” zero became a strategy.

Capital got cheap. Asset prices did more of the work than productivity.

2022–2024: the reversal.

Rates repriced fast, and anything built on cheap borrowing felt it first.

Now here’s the part I care about as a CFO:

If your plan only works when money is cheap, it’s not a plan.

It’s a rate bet.

What I’m advising SMB owners to do instead:

1. Treat debt like a core operating input, not a financing afterthought. Know maturities, covenants, and what renewal looks like if it’s 200–300 bps higher.

2. Run the business on cash flow reality, not valuation language. Valuation is optional. Payroll isn’t.

3. Build a “higher-for-longer” base case. You don’t need to predict the Fed. You need a model that survives your least-favorite scenario.

Question for you: where is your business most exposed to rates right now - pricing, payroll growth, customer demand, or refinancing risk?

If you want, send me a note and I’ll tell you the first place I’d stress-test in your numbers.

#finance #taxes

If your close takes 20+ days, you’re running the business on old news.

Not because your team isn’t working hard. Because the process is built to deliver answers late.

A 20+ day close usually means leadership is making decisions using numbers that describe last month’s reality, not this month’s.

What that typically causes in founder-led businesses:

• Margin erosion that gets noticed after it repeats
• Cash surprises that feel “sudden” but were visible in the data
• Pricing and hiring debates driven by opinions instead of trendlines
• A leadership team that spends more time arguing about the numbers than using them

For many SMBs, a reasonable goal is a close measured in single-digit business days, not weeks. Complex, multi-entity companies can take longer  but three weeks is still a signal the system is breaking down.

Why closes drift past 20 days:

1. No cutoffs or owner accountability (coding, approvals, time tracking)

2. Reconciliations happen at month-end instead of routinely

3. Revenue/COGS/inventory requires heavy manual cleanup

4. The close lives in someone’s head, not a calendar and checklist

A practical way to cut “days to close” without burning out your team:

Step 1: Put the close on a calendar with owners + deadlines
Step 2: Reconcile cash + key balance sheet accounts weekly
Step 3: Standardize recurring accruals and automate what repeats
Step 4: Set a “draft P&L” date and review it in 30 minutes every month
Step 5: Track one number: days to close and improve it quarterly

If your close is still taking 20+ days, don’t start with “work harder.” Start with cutoffs, owners, and weekly reconciliations.

What’s your current close time in business days?

#finance #business

Family. Faith. Finance.

Those are the three pillars I try to live by and I keep them in that order on purpose.

Family keeps me clear on what the work is for. A strong business is great, but not if it costs the relationships that matter most.

Faith keeps my standards consistent. It’s the anchor that pushes me to choose integrity over convenience, especially when no one is watching.

Finance is the tool. When managed well, it reduces stress, buys time, and creates options. When ignored, it quietly adds pressure to everything else.

If you’re building a business, here’s a practical takeaway: treat your financial decisions like personal decisions, because they are.

One simple habit that works:

- Protect non-negotiable family time on the calendar
- Set a value-based rule for what we won’t do for revenue
- Review cash flow weekly, not just profit monthly

When those three are aligned, the business runs cleaner and so does life.

What’s one rule or rhythm you’ve put in place that helps you stay aligned?

#life #business

Goldman Sachs is collaborating with Anthropic to develop AI agents that automate trade and transaction accounting, client due diligence, and onboarding.

My opinion: this is the clearest sign yet that “agentic automation” is moving from demos to the parts of finance where controls actually matter.

Not because banks love shiny tools. Because they won’t put anything near regulated workflows unless the control environment can be made defensible.

Here’s what I think changes next.

Finance stops being a monthly sprint and becomes an exception business.

When AI can reliably prepare the evidence layer, the operating cadence shifts:

• Reconciliations trend toward continuous matching with exception queues
• Close becomes a confirmation cycle, not a scavenger hunt
• Working capital visibility improves because support is attached in real time
• Forecast inputs get cleaner because the books aren’t perpetually stale

The mistake most companies will make is treating AI like an assistant and keeping the legacy workflow intact.

If you want real outcomes, redesign the system:

• Map the end-to-end process (what happens, where, and why)
• Separate closed-loop tasks from judgment-heavy decisions
• Put review checkpoints and approval thresholds in writing
• Require audit trails by default (who did what, when, and on what evidence)

The durable model isn’t “AI replaces finance.”

It’s “AI prepares the file. Humans sign the decision.”

Question for operators and finance leaders: if you had to cut your close time in half this quarter, what breaks first in your process?

#finance #news

If you’re thinking you can buy a business without putting any skin in the game, you’re setting yourself up with false expectations and probably killing the deal before it even has a chance. 

And this is about showing commitment, taking responsibility, and proving that you’re serious about running the business. 

Ben breaks down why this matters and why so many deals stumble at this stage. 

Watch the video to hear his valuable advice.

One birthday, my nephew didn’t get a gift.

He got a deposit.

Instead of more gifts, I put $100 into an account for my nephew every birthday and Christmas. And once he was old enough, we talked through what that money was doing and why it mattered.

That’s the part most people skip.

People get weird about trust funds.

But the issue isn’t kids having money.

It’s kids getting money with zero understanding.

If you put away $200/month for a kid (or even $100), over time it becomes meaningful.

Not “never work again” money.

But real, life-opening options.

The difference-maker is the conversation that runs alongside the capital:

• Why the money exists

• What compounding actually means

• Where it’s invested (and why)

• What responsibility comes with it

Because capital without context is where things go sideways.

With my nephew, the conversation got personal fast:

He liked sports → we looked at Nike and Under Armour.
He liked video games → we talked about gaming companies. And yes he 
loved the meme stock craze with Game Stop. Where my diamond hands at! 

Money stopped being mysterious. It became specific.

Now he’s in trade school, and our conversations sound like:

• Will AI replace parts of your job?

• What infrastructure still has to exist no matter what?

• Where does opportunity move next?

That doesn’t happen if money stays taboo.

The goal isn’t raising rich kids.

It’s raising kids who understand money before they’re forced to learn the hard way.

If you could teach one concept first: budgeting, saving, investing, or earning, what would it be?

Follow Tom Dillon, CFA for more content on finance.

#finance

Too many founders still use their bank balance as a proxy for financial health. I understand the instinct. You open the app, see cash in the account, and feel a brief sense of relief.

But that number can be dangerously reassuring.

Your bank balance tells you what is there today. It does not tell you what has already been claimed by payroll, rent, taxes, supplier payments, loan obligations, or delayed expenses that have not cleared yet.

That is the difference between seeing cash and understanding cash.

Over the years, I have seen businesses with strong sales, healthy margins, and impressive growth still operate under constant financial pressure. Not because the business was weak, but because the timing of cash was poorly understood.

That is where many good businesses get caught.

Revenue can look strong while liquidity is under strain. Profit can look healthy while the company is still one delayed payment away from stress. 

Receivables may look like assets on paper, but until they are collected, they are assumptions.

This is why cash flow discipline matters far more than most founders want to admit.

It forces a more honest view of the business.

Not:
“How much money is in the bank?”

But:
“What is already committed?”
“What is uncertain?”
“What happens if a major customer pays late?”
“What breaks first if revenue softens for 60 days?”

Those are the questions that separate financial confidence from financial hope.

In my experience, businesses rarely run into trouble because the owner was not working hard enough or selling enough.

They run into trouble because cash and timing stop lining up.

And when that happens, decisions become reactive. Pressure rises. 

Optionality disappears.

That is why I often say this: growth does not solve poor cash timing. Better sequencing does.

Tighter invoicing.
Better payment terms.
Clearer visibility on committed outflows.
A realistic view of receivables.
A forward cash flow model that shows pressure before it arrives.

That is not just better finance. It is better leadership.

A bank balance can make you feel safe for a moment.

A real cash position tells you whether you actually are.

How often do you think founders confuse cash in the bank with real financial control?

#finance #cash

I’ve been thinking a lot about how we talk to our kids about money. Or more accurately… how most of us don’t talk about it at all. 

Growing up, money was either there or it wasn’t. “We can’t afford that” was the end of the conversation. 

No context. No why. No trade-offs. 

What if instead of hiding money, we brought kids into it early? 

Nothing fancy. Even a grocery store run works: “Here’s the budget. If we go over, something has to go back.” Then let them decide. 

That one moment teaches more than a lecture ever could: Money is finite. Trade-offs are real. Choices matter. 

Same thing with saving: Instead of “maybe next time,” it becomes: “We’re saving for this trip.” 

Now everyone’s part of it. Delayed gratification isn’t abstract anymore. It’s lived. 

P.S - What’s one money habit you’re trying to teach your kids early? 

Follow Tom Dillon, CFA for more content on finance.  

#money #kids

Everyone talks about money, strategy, and deals, but here’s the truth no one admits…

If you can’t master relationships, you’ll fail in business. 

Skills and capital matter, but the people you connect with ultimately decide whether you win or lose.

Ben dives into this from his own experience in the video, listen to him to know why relationships really make or break success.

#money #finance

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