Brad Jacobs’ Quadrant: How to Evaluate Big, Messy, Worthwhile Bets

Stop chasing clean deals. Start underwriting solvable complexity.

Entrepreneurship through acquisition (ETA) tends to reward caution. The playbook is familiar: find a simple, profitable business with recurring revenue, a loyal customer base, and a retiring founder. The underlying premise is one of de-risking—preserving stability and protecting downside. But there is another school of thought.

In How to Make a Few Billion Dollars, Brad Jacobs—a serial entrepreneur who built multi-billion-dollar companies across trucking, logistics, and chemicals—offers a different lens. Rather than minimize complexity, Jacobs seeks it out. He looks for large, broken businesses with solvable problems. His quadrant-based approach reframes ETA strategy, urging entrepreneurs to evaluate not just risk, but the scale-adjusted nature of opportunity. In doing so, he challenges the conventional wisdom that clean businesses are always better bets.

The ETA model, particularly in its traditional form, is structurally biased toward small, clean, and easily understood businesses. Searchers often face compressed timelines, modest acquisition budgets, and limited operating experience. Investors, for their part, tend to favor predictable cash flow over volatility, and judge success by IRR multiples more than long-term reinvestment potential.

As a result, many first-time CEOs are incentivized to pursue targets that present minimal surface-level risk—contracted revenues, simple operations, low customer concentration. These businesses are easier to diligence, easier to close, and easier to pitch to investors. And to be clear: that model works. It’s well-designed for optimizing continuity and incremental growth through light operational improvement.

But if you’re an ETA entrepreneur seeking the opportunity to truly transform a business—to rewire its systems, reallocate its capital, or scale its platform—Jacobs’ approach may be closer to your fit. His framework starts with a different premise: the best outcomes are often hidden inside fixable complexity.

Brad Jacobs evaluates opportunities along two critical axes: deal size and operational complexity. These two variables form the foundation of his investment philosophy—not because they’re novel, but because of how he interprets them through a systems lens.

Deal size refers to the total revenue base or the scope of economic opportunity a business presents. It answers a central question: If we get this right, how big can this become? Size matters not because it guarantees success, but because it creates room for professional management, margin expansion, and reinvestment. Larger businesses allow for deeper leadership benches, more meaningful systems, and a structurally higher ceiling on growth. A $5 million revenue business with 20% EBITDA may look appealing, but a $50 million revenue business at break-even—if fixable—offers a much more scalable platform.

The second axis is mess, which Jacobs uses as shorthand for deal risk—the operational, cultural, and structural issues that make a company difficult to run. This includes everything from founder-dependence and outdated systems to poor financial visibility, inconsistent service quality, or missing leadership layers. Mess, in this context, isn’t a disqualifier—it’s a constraint. And like all constraints, it can either block growth or become the raw material for transformation. Jacobs’ insight is that not all mess is fatal. Some of it is cosmetic. Some of it is solvable. The key is distinguishing between the two.

Together, these two axes—deal size and operational mess—form what I call The Jacobs Quadrant. Most searchers live in the bottom-left: small, simple, and safe. These businesses are easier to diligence, easier to close, and easier to explain to investors. But they’re often structurally capped. Jacobs, by contrast, seeks out the top-right: big businesses with solvable problems. His goal isn’t to avoid mess. It’s to underwrite solvable complexity at scale.

To make this mental model stick, I reimagined the quadrant through the lens of food—partly because I’m a systems thinker, but also because I’m a foodie. Framing deals as meals helped solidify the risk-reward profiles in my mind. Every deal feeds your ambition differently—and some are worth the prep more than others.

The Grilled Cheese is small and simple. Warm, familiar, and easy to digest—but rarely enough to fuel long-term growth.

The A5 Wagyu Steak is big and simple. Highly coveted, carefully sourced, and often priced to perfection.

The Gas Station Burrito is small and messy. Chaotic, inconsistent, and more likely to backfire than satisfy.

The BBQ Brisket is big and messy. Intimidating at first, but with patience, heat, and the right tools—it becomes a meal worth remembering.

Jacobs doesn’t chase perfection. He brings process. The brisket quadrant is where few look—and where his biggest outcomes live.

Most searchers never seriously consider BBQ Brisket deals. The complexity is too visible, the diligence feels ambiguous, and the post-close operating lift can seem overwhelming—especially for first-time CEOs.

But what Jacobs recognizes, and what many in ETA miss, is that mess often creates mispricing. While others walk away at the sight of inefficiency, unscalable processes, or founder-reliant teams, he underwrites whether the problems are temporary and solvable. This distinction matters. A business that’s poorly run is not necessarily a bad business. It may simply be one that has outgrown its structure—or never had one to begin with. In these situations, mess isn’t a red flag. It’s a discount.

The key, then, is not to avoid complexity, but to filter it through a systems lens.

Can the issues be addressed through better people, better process, or better data?

Is the mess cosmetic, or is it structural?

Are you stepping into dysfunction—or into a business that’s never been properly managed?

The difference determines whether you’re taking on unbounded risk—or unlocking hidden leverage.

Jacobs doesn’t build companies by finding perfect businesses. He builds by spotting imperfect ones with fixable constraints.

His approach isn’t about chasing risk for its own sake. It’s about reframing risk as a function of structure, ambition, and capability. Not everyone is wired for BBQ Brisket deals—and not every ETA journey should be.

But if you’re someone who finds yourself drawn to scale, transformation, and complex systems, it may be worth asking:

What kind of business are you actually optimizing for? Something safe, proven, and quiet? Or something messy, ambitious, and worth rebuilding?

The traditional ETA model is optimized for continuity. Jacobs’ model is optimized for inflection. Both approaches can work. But they demand different filters, different frameworks, and perhaps most importantly—different kinds of CEOs.