
8 Characteristics of Durable SMBs
by Highland Legacy Capital
Author(s): James Jackson
Introduction: Defining “Durability” in the Lower Middle Market
Durability in small and medium-sized businesses (SMBs) isn’t about surviving downturns; it’s about compounding strengths over decades. We don’t just look for businesses with momentum—we look for structural staying power. Informed by hours spent evaluating companies, speaking with owners, and studying what works, we believe durability can be decoded.
While no business is perfectly future-proof, the most compelling companies tend to exhibit a distinct set of characteristics that create not only resilience, but also a platform for compounding value across market cycles.
The 8 Characteristics of Durable SMBs
This article codifies our perspective on the eight most critical characteristics of durable SMBs, drawing from empirical studies (notably Stanford GSB's Search Fund Studies), our own diligence frameworks, and the principles that have guided our own journey building Highland Legacy Capital.
1. Recurring revenue with high retention
Durable businesses begin with stable top-line visibility. As noted in the Stanford Search Fund Primer (2021), 73% of successful search fund acquisitions featured some form of recurring or reoccurring revenue. Whether contractual (e.g., software subscriptions), behavioral (e.g., dental practices), or embedded (e.g., regulated inspection services), recurring revenue provides the foundation for planning, investing, and weathering volatility.
But revenue quality isn’t about recurrence alone—it’s about retention. High customer retention (>90% annually) suggests not only product-market fit but switching friction and economic loyalty. We assess this through cohort analysis, revenue concentration, and customer interviews.
2. Embedded in mission-critical workflows
In B2B settings, durable businesses are not “nice to have”—they are operationally essential. We look for products and services that are woven into customer workflows, such that removing them would disrupt output, compliance, or customer satisfaction.
Examples include specialized manufacturing inputs, back-office SaaS for regulated sectors, or outsourced services tied to health, safety, or uptime. Durable businesses become "infrastructure" in their category.
3. Market niche leadership with barriers to entry
A study from the Harvard Business School (Bhide, 2000) notes that most successful entrepreneurial firms don’t dominate massive markets—they dominate small ones. We like companies that are #1 or #2 in a narrowly defined niche, especially where geography, reputation, or specialized know-how serve as structural moats.
We score industries using our own in-house evaluation matrix to weigh entry barriers, competitive intensity, customer power, supplier dynamics, and the availability and desirability of substitute products or services. Durable SMBs often occupy asymmetric terrain even within the context of a healthy industry or sub-industry.
4. Favorable unit economics and operating leverage
Durable companies demonstrate consistent unit-level profitability and evidence of scale advantage. We look for gross margins above 40%, low working capital intensity, and contribution margins that improve with scale.
Companies with these traits have the luxury of being able to reinvest in growth without constant capital injections. The Outsiders (Thorndike, 2012) underscores capital discipline as a common trait among companies with exceptional long-term performance.
5. Long tenure of customers, employees, and ownership
Durability often lives in the stories behind the spreadsheet. Companies with long-standing customer relationships, multi-decade employees, and owner-operators who have run the business for 15+ years often reflect a deeply embedded trust in the business ecosystem and an ability to drive value for all stakeholders year over year.
This tenure creates continuity of culture (which we define as measurable and codifiable “working norms” — but more on that in another article), institutional knowledge, and relational equity. During diligence, we explore org charts, tenure stats, and turnover patterns—as well as interview owners for insights into leadership philosophy.
6. Conservative balance sheet and limited external dependencies
As the 2020 Stanford Search Fund Study observed, post-acquisition performance is often derailed not by margin compression but by liquidity stress. Durable businesses don’t chase growth with leverage or capital intensity—they grow from cash flow.
We favor companies with minimal capex (<5% of revenue), low customer concentration (<15% per account), and limited regulatory risk. Asset-light, internally funded models compound over time with fewer shocks.
7. Clear levers for value creation, without heroics
A durable business should not require brilliance to improve. Instead, we look for firms where a capable team applying best practices in pricing, sales management, or technology adoption can drive meaningful gains.
To understand value creation levers, we assess pricing power, under-optimized workflows, and digital maturity. As one investor put it, "We want to buy a machine that works, not a turnaround that might."
8. Cultural integrity and aligned stewardship
Finally, durability rests on intangibles. Is the culture resilient or brittle? Is the seller a steward or a speculator? Will employees stay after a change in ownership?
We spend a lot of time thinking about long-term stewardship, and often ask sellers: "If you were staying another 10 years, what would you do?" Durable businesses tend to have leaders with pride, not just exit intent.
A closing reflection: durability is not static over time
These characteristics aren’t a checklist—they’re a lens. Businesses can evolve from fragile to durable or vice versa depending on leadership, market shifts, and decisions made under pressure. Our job as investors and operators is to recognize the patterns early, ask the hard questions, and bring playbooks that reinforce what’s working while addressing what isn't. To be thoughtful about protecting durability — and to consciously double down on virtuous, durability reinforcing characteristics as waves of expansion and evolution are planned and executed.
Durability creates the space for compounding; the luxury of thoughtful reinvestment in the pursuit of sustainable growth. For us, that means finding businesses we can bet on and build with for a decade, not just a quick flip.
Still, open questions remain:
What specific leading indicators best predict durability pre-acquisition?
Can certain industries sustain durability across multiple ownership transitions?
How can we best measure culture pre-close?
We’re continuing to study these questions, and in future articles, we’ll share deeper dives on our evaluation frameworks, portfolio learnings, and owner psychology. If you’re an operator, advisor, or seller with a view—we’d love to hear from you.
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Highland Legacy Capital is a search fund focused on acquiring and operating one exceptional business. We believe in operational excellence, disciplined investing, and enduring partnerships. We also believe everyone has something to teach us — so don’t hesitate to get in touch.