Welcome to Creator Capitalist Conversations, a series spotlighting Category Designers who have rejected traditional career paths and built lives around what makes them different. Our new book, Creator Capitalist, launches March 17th. Join the waitlist.
Dear Friend, Subscriber, and Category Pirate,
Jeff Klimkowski is a different kind of CFO.
Yes he has the pedigree as a high flyer at Deutsche Bank.
Yes DUDE Wipes is massively successful, crossing $300MM in revenue last year.
But more importantly, he had a ton of skin in the game as a co-founder and as the OG line of credit for DUDE Wipes.
He’s an in the Arena CFO that would make Milton Friedman proud.
When your money and the company’s money are the same pile, you think differently about every dollar.
Jeff didn’t just become CFO. He redesigned what the role means.
At DUDE Wipes, four verticals roll up to the CFO:
Finance and accounting
FP&A
Sales strategy
Supply chain.
The problem with how the industry defines the job is that most people think it’s just the first one.
Jeff sits in every major Walmart and Target line review alongside Sean. He hears from the buyer’s mouth what their long-term strategy is—so his forecasts aren’t built on salespeople’s optimism alone. He goes to co-manufacturer meetings so he can look at the whites of the buyer’s eyes before he commits working capital to inventory.
This is not how most CFOs operate.
Most CFOs sit in a skybox. Jeff is on the field.
Zero free cash flow growth. That’s the goal.
Not because DUDE Wipes isn’t profitable. Because every dollar of EBITDA gets reinvested—into working capital, CapEx, and marketing—until free cash flow hits zero at year’s end.
Zero means Jeff is deploying capital at the exact speed the category demands.
Too much free cash flow? You’re not investing enough. You lack conviction. The category will outgrow you while you sit on cash.
Negative free cash flow? You’re over your skis. You’ll need to raise money, dilute equity, and lose control.
Zero is the surfer sitting in the pocket of the wave.
Jeff knows the max growth rate they can sustain in a given year because of this discipline. Right now: 50% per annum at zero free cash flow. When numbers get big, 50% is a big number.
And it’s not set-it-and-forget-it. They’re tweaking the plan constantly—rolling 12 months on the finance side, rolling 24 months on supply chain. New data in, new adjustments out.
The make-free-cash-flow button.
Eddie asked Jeff: when you need to push the free cash flow number, what do you press?
The first answer was boring and brilliant: cash collections from retailers.
Nobody was quarterbacking receivables. Invoices were getting lost in EDI transmissions. POs weren’t registering correctly between systems. Charge-backs went uncontested. It’s the kind of work nobody glamorizes—but hiring one person to own it improved cash collection by 40%.
Now they’re layering in AI agents to match invoices, flag errors, and automate the back-and-forth with retailer portals. The person quarterbacks. The agents do the grunt work.
Second answer: SKU-level demand planning. DUDE Wipes knows how much they’ll sell. The problem is the mix—selling the right product at the right time to the right channel. When a new innovation outperforms expectations, there’s a 90–120 day lead time before they can adjust production. AI that ingests retailer data and optimizes assortment by channel compresses that gap.
Real example: DUDE Wipes was running promotions at food retailers and only seeing 10–15% lift versus competitors. Why? They were selling out by Wednesday. Empty shelves for the rest of the week. High-growth category problems that only show up when you look at the data with precision.
Meet Diesel Dan.
Greg Brown, DUDE Wipes’ SVP of Ops and Technology, built an AI agent called Diesel Dan.
Here’s what Diesel Dan does: when the manufacturer finishes a production run, an automated report gets sent over. Diesel Dan reads the report, books trucks across three counterparties, maximizes weight and volume per load, and notifies the operations team. Fully automated.
Before Diesel Dan, inventory piled up at the manufacturer because trucks weren’t getting booked fast enough. That meant less production capacity. That meant slower growth. That meant working capital sitting in the wrong place at the wrong time.
Dan fixed the bottleneck. Stockouts dropped. Freight costs stabilized. And the operations floor went from reactive to predictive.
As Jeff put it: “Dan never sleeps, never guesses, and never forgets.”
This episode isn’t about spreadsheets.
Or accounting.
Or even AI.
It’s about what happens when the CFO stops being the department of no and starts designing the financial system that powers category creation.
Jeff’s approach works because the conditions force it. Skin in the game. A new category that didn’t exist. And a bootstrap discipline that makes every dollar earn its spot—or get cut.
That’s the Agentic CFO.
Here’s how to navigate this conversation:
00:00 – From Deutsche Bank to DUDE Wipes: Jeff’s origin story—the Wall Street Journal in the passenger seat, the dream job, and the childhood friends who derailed everything.
01:59 – The four verticals of a real CFO: Finance & accounting, FP&A, sales strategy, and supply chain. Why most people only know about the first one.
09:06 – Investing 18 months ahead of demand: Writing checks for CapEx three years out. Why Jeff sits in every Walmart and Target line review. And why he’s been wrong on the downside of every forecast.
16:54 – The VC rejection that saved DUDE Wipes: 20–30 meetings after Shark Tank. Every one said no. “You’ll never get guys to use wipes.” So they got profitable instead.
18:48 – “EBITDA is the most overrated metric on the face of the planet.” Jeff’s financial North Star: free cash flow equals zero. What that means, why it works, and how it sets the pace for growth.
26:35 – The make-free-cash-flow button: Cash collections, AI-powered invoice matching, and a 40% improvement from one hire.
31:23 – SKU-level demand planning with AI: The working capital problem nobody talks about—selling the right mix at the right time.
34:50 – Selling out by Wednesday: Why DUDE Wipes’ promotions were underperforming and what they found when they looked closer.
36:30 – Diesel Dan: The AI agent that books trucks, maximizes loads, and turned DUDE Wipes’ supply chain from reactive to predictive.
41:53 – Jeff’s AI wish list: Sales strategy, demand planning, and why legal is about to get 70–80% automated.
44:59 – Why Jeff said yes: Credibility, alignment with strategy, and the only pitch that works—”here’s how many thousands of hours this saves.”
This conversation is the case study. The Agentic CFO is the system.
In the mini-book, we break down Milton Friedman’s four ways to spend money, the four CFO archetypes (Arena, Dividend, Enabler, and Government), why free cash flow—not EBITDA—is the strategic metric of belief, and the five-step playbook for designing an Agentic finance system with AI agents.
Jeff is the Arena CFO. Which quadrant are you in?
To connect with Jeff:
Arrrrrr,
Category Pirates 🏴☠️
P.S.—Remember Friedman’s matrix?
The Arena CFO wins because they have skin in the game AND a new category to build.
That’s not just true for CFOs. It’s true for careers.
The knowledge workers who thrive in the next decade won’t be the ones with the best resumes. They’ll be the ones who stop renting out their expertise and start owning what they create.
Our new book, Creator Capitalist, launches March 17th. We’re opening the Founding 50—exclusive early access for Academy alumni and founding subscribers.
Founding Subscribers can join the Founding 50 here.
You can become a Founding Subscriber here.
Or join the waitlist to get the book on March 17th here.
