In the world of holding companies, “normal” is often overrated. When you’re starting, acquiring, and building businesses by investing capital, time, talent, and technology (holding company), the financial picture you get isn’t always the neat and tidy stream of revenue most corporate textbooks talk about. Instead, you often find yourself staring at the unpredictable, sometimes lumpy, occasionally baffling reality of what we like to call “weird cash flow.”
This isn’t chaos for chaos’ sake. Weird cash flow can be a sign of opportunity, innovation, and long-term growth hiding behind numbers that don’t behave themselves. And for those who know how to read the signals, it’s more exciting than unnaturally symmetrical spreadsheets.
Weird cash flow is money movement that doesn’t follow the typical smooth, predictable patterns most corporate accountants dream about. It might be highly seasonal, spiking dramatically during certain months. It might come in lumpy bursts after long dry spells. It might be influenced by quirks in payment cycles, odd customer behavior, or unique business models that defy the “monthly recurring revenue” ideal.
The term “weird” isn’t meant to imply that it’s bad. In fact, weird cash flow often means a business has a distinctive position in its market. Maybe it sells something people only need once every few years but are willing to pay a premium for. Or maybe it’s tied to industries where timing is everything and big payouts come all at once.
Weird cash flow simply means it takes a bit more imagination, patience, and strategic thinking to manage—and that’s where the real fun begins.
Traditional thinking says predictable cash flow equals a healthy business. But while predictability makes bookkeeping easier, it can also limit your opportunities. Predictable streams tend to attract more competition, which pushes margins down. Everyone wants the easy-to-model, low-volatility business, which means prices get driven up and returns get squeezed.
Weird cash flow, on the other hand, scares off a lot of buyers and operators. They see the irregularity and assume it’s risky or unmanageable. For those willing to dig deeper, that “risk” is often just the natural rhythm of the business—and it can come with better margins, less competition, and stronger long-term value.
In other words, weird cash flow is like finding a hiking trail nobody else wants to take because it looks steep from the trailhead. Sure, it’s a bit more work, but the view is usually much better at the top.
When you operate in a market with irregular cash flow, you often face fewer competitors. With less competition, you can maintain healthier margins and enjoy greater control over pricing. Your customers may not care that your revenue is seasonal—they care that you deliver something they can’t easily get elsewhere.
Weird cash flow often means customers interact with you in bursts rather than through constant, repetitive transactions. These infrequent but significant interactions can lead to deeper relationships. The customer might think of you more like a trusted specialist than just another vendor.
Irregular inflows force you to think differently about reserves, investments, and timing. Instead of relying on constant inflows to cover expenses, you get creative—using surplus cash from good months to fuel growth, or structuring deals with suppliers to better match your cash cycles. This flexibility can make you a stronger operator over time.
Liking weird cash flow is as much about mindset as it is about financial skill. If you’re used to the comfort of monthly stability, it can be nerve-wracking to see big swings in your bank balance. You need to replace that craving for uniformity with an appreciation for patterns, even if those patterns are unconventional.
It’s a bit like gardening. Some plants bloom year-round. Others give you one massive, breathtaking bloom in the spring and nothing else for months. Both have their beauty, but the second one makes you more attuned to cycles, timing, and anticipation.
With unpredictable timing, a healthy cash reserve isn’t optional—it’s survival. This buffer helps you cover fixed costs during slow periods without scrambling for short-term loans or cutting essential expenses.
Instead of trying to nail down one “perfect” forecast, create multiple scenarios—best case, worst case, and likely case. This way you’re prepared for both lean months and surprise windfalls.
If your cash flow has a particular cycle, negotiate payment terms, supplier contracts, and debt schedules to align with your peak months. A lender who understands your cycles can be an invaluable partner.
The leaner your fixed cost structure, the more freedom you have to ride out the dips. It’s easier to handle the “weird” when you’re not weighed down by unnecessary overhead.
For some of us, unpredictability is part of the thrill. It keeps the work interesting. When you’re working with steady, predictable income, the main challenge is efficiency. When you’re working with irregular flows, the challenge is creativity—how to capture value when it appears, how to prepare for the next cycle, how to turn volatility into advantage.
It’s a bit like fishing in a lake that doesn’t always have fish at the same spots. You learn to read the signs, know when to cast, and when to wait. That process builds skill, patience, and intuition—qualities that serve you well in all aspects of business.
There’s also a certain satisfaction that comes from taming the “wild horse” of irregular cash flow. Anyone can ride a horse that walks in a straight line at the same pace all day. But mastering the bucking, unpredictable one? That’s a different level of accomplishment.
And when those big payouts land, they feel more rewarding. You’ve weathered the quiet stretches, planned for the lean moments, and now you get to enjoy the harvest. It’s not just income—it’s proof that your patience and strategy paid off.
Of course, liking weird cash flow doesn’t mean ignoring its risks. Some businesses with irregular patterns truly are unstable or unsustainable. The trick is to distinguish between volatility that’s natural to the business model and volatility caused by deeper problems.
Watch for signs of declining demand, rising customer churn, or dependence on a single client. Weird cash flow is only attractive when it’s driven by timing, seasonality, or niche characteristics—not when it’s a symptom of trouble.
Over time, weird cash flow can be just as dependable as steady cash flow—once you understand its pattern. If you track enough data, the irregularity often reveals its own rhythm. You begin to see that the spikes and valleys are not random at all, just different from the tidy monthly graph most people expect.
For holding companies and multi-business owners, weird cash flow from one business can complement the patterns of another. A seasonal spike in one portfolio company might align perfectly with a slower period in another, smoothing out the overall financial picture.
In the end, weird cash flow rewards the operators and investors who are willing to think differently. It requires a mix of patience, preparation, and a dash of nerve. But those who embrace it often find better opportunities, healthier margins, and more freedom to operate without the crush of constant competition.
If you’re the type who enjoys a bit of unpredictability, who doesn’t mind swapping the smooth and simple for the challenging and rewarding, then weird cash flow might be your hidden advantage.
Weird cash flow isn’t for everyone, and that’s exactly why it can be so valuable. It requires skill to manage and a willingness to see patterns where others see chaos. But for those who master its quirks, it can unlock opportunities that predictable businesses rarely offer. It keeps you sharp, keeps you creative, and—most importantly—keeps your business from blending into the crowd.
Ryan Schwab serves as Chief Revenue Officer at HOLD.co, where he leads all revenue generation, business development, and growth strategy efforts. With a proven track record in scaling technology, media, and services businesses, Ryan focuses on driving top-line performance across HOLD.co’s portfolio through disciplined sales systems, strategic partnerships, and AI-driven marketing automation. Prior to joining HOLD.co, Ryan held senior leadership roles in high-growth companies, where he built and led revenue teams, developed go-to-market strategies, and spearheaded digital transformation initiatives. His approach blends data-driven decision-making with deep market insight to fuel sustainable, scalable growth.
