Annotations (16)
“Castronics performs a very humble function, which is they carve into the end of the pipe the threads so that you can bolt together, you can wind together two lengths of pipe and put it down in oil or gas well. That threading needs to have two characteristics. It needs to be highly accurate so when you're at this remote site with a lot of expensive labor around and you're on the clock, those fit together beautifully.”— Royce Yudkoff
The Castronics Case Study · p. 15
Strategy & Decision Making · Economics & Markets
DUR_ENDURING
$45 service on $3000 total: ratio creates moat
“When you buy an enduringly profitable, mature small business at four times EBITDA, you are pulling off a 25% yield on your total purchase price. If you financed about two-thirds of it with debt, senior and seller debt, and that debt is typically at some single-digit interest rate, your return on equity before any growth is somewhere like 60% or 65%. If you actually grow the business, even at a moderate rate, 5%, 6% a year, that's even higher.”— Royce Yudkoff
Perspective on Growth in Small Businesses · p. 19
Economics & Markets · Strategy & Decision Making
DUR_ENDURING
Leverage converts 25% yield to 60% ROE
“We encourage our students to buy businesses that have recurring customer bases. That means customers where they are automatically going to repurchase the service or the product from year to year because it's in their financial interest to do so. That to not do that almost requires a whole new round of work in re-evaluating and selecting. When a local ambulance service contracts with System Design West, they link together their electronic information systems.”— Royce Yudkoff
Desirable Characteristics in Small Businesses · p. 8
Strategy & Decision Making · Economics & Markets · Psychology & Behavior
DUR_ENDURING
Value delivered exceeds price paid by orders of magnitude
“If you're the manager of a 40-story building, that cost is infinitesimal to you. In fact, it's passed through as a common area maintenance charge, you don't even pay it. But you are concerned that on your class-A building, your window washers are on and off the building quick and not disturbing the tenants. More than anything else, that a bucket is not dropped on a convention of trial lawyers. In other words, safety is paramount.”— Royce Yudkoff
Desirable Characteristics in Small Businesses · p. 9
Psychology & Behavior · Economics & Markets · Strategy & Decision Making
DUR_ENDURING
Downside from switching exceeds upside savings
“Growth just creates risk. If you think about looking for businesses that have high recurring revenues, the faster growth, the lower your recurring revenues, almost by definition. New customers, new problems. It's not just new customers, new problems, it's new customers, probably different problems. It may be that with growth, you're adding more high-value add customers but that's not the way it usually works. It's usually you end up like mining.”— Rick Ruback
Perspective on Growth in Small Businesses · p. 19
Strategy & Decision Making · Economics & Markets
DUR_ENDURING
Growth dilutes recurring revenue and margins
“In big businesses, you're pretty almost always looking for what is a pre-insurmountable barrier. The barrier tends to be something real, like a patent, an idea, low-cost position, brand something, license, whatever. In small firms, the barrier is often excellent execution. So people don't switch because you as a small business person do what you do really well. You never give them a reason to get mad at you. That is itself a barrier in the same way a license might be for a larger company.”— Rick Ruback
Desirable Characteristics in Small Businesses · p. 9
Strategy & Decision Making · Operations & Execution
DUR_ENDURING
Execution quality IS the moat in small firms
“I always approach it by asking a different question. I think the question you want to ask is why is this business small? Some businesses are small because they're lousy businesses. But some businesses are small because they're serving a local market in kind of a special way. That's the one you want to buy. Their market is small, they're the best, and everybody wants to use them. But you can only ship bread 50 miles. So you can be the best bakery and have huge profits.”— Rick Ruback
Desirable Characteristics in Small Businesses · p. 11
Strategy & Decision Making · Economics & Markets
DUR_ENDURING
Small from constraint or incompetence?
“One of the big risks you face is you buy a great business for seven, eight, 10 times EBITDA and then there's multiple compression. The whole space re-rates and suddenly, these businesses trade for seven times, not nine times. It's really hard for re-rating to take place when a business is bought at four times EBITDA. It's just there's an almost irreducible minimum here.”— Royce Yudkoff
The Risk from the Investor's Standpoint · p. 7
Economics & Markets · Strategy & Decision Making
DUR_ENDURING
Floor valuation plus low leverage equals resilience
“Across North America there are hundreds of thousands of small businesses with anywhere from $750,000 to $2 million of EBITDA. These businesses often have founders who need to retire. The businesses are enduringly profitable, successful small firms but there's no natural successor. That population is much smaller than the population of people reaching the end of their careers in these small firms.”— Royce Yudkoff
An Overview of Search Funds · p. 1
Economics & Markets · Strategy & Decision Making · Business & Entrepreneurship
DUR_ENDURING
Valuation inefficiency from succession gap
“Because these markets are relatively small markets, the idea of building a new pipe threading facility to split that market in half it's just not that appealing as a proposition. It could happen if you're totally undisciplined and raising the price. But if you're reasonably thoughtful about it, you're not going to invite in competition. Castronics was in Kimball, Nebraska. I think there was not another pipe threader for 500 miles. So what are you going to do?”
The Castronics Case Study · p. 15
Strategy & Decision Making · Economics & Markets
DUR_ENDURING
Small market plus geography equals natural moat
“I don't like technology companies. Anything that has this stroke of pen risk. For example, there was a time when autism clinics were like the best investment ever. I guess it was the time before that, MRIs were the best investment ever. The problem with all of those is that they have all this reimbursement risk. Somebody can just change the reimbursement rates and what are you going to do then? If reimbursement rates dropped by 20%, it doesn't change your cost of providing the service at 20%.”— Rick Ruback
Red Flags when Searching for a Small Business · p. 17
Economics & Markets · Strategy & Decision Making
DUR_ENDURING
Revenue changes hit margins disproportionately
“If the business is priced at four times there's one business not growing priced at four times and there's a similar business that's growing at 25% a year, you're not going to buy that business at four times, that might be six times. So you're paying for it upfront as if you've been able to realize it and then you have to go realize it. That said, I think every business does better if it can grow a little. But I really like growing a little, as opposed to growing a lot.”— Rick Ruback
Perspective on Growth in Small Businesses · p. 20
Economics & Markets · Strategy & Decision Making
DUR_ENDURING
Paying for growth upfront eliminates advantage
“The biggest challenge of being an investor in the private equity world is that an enormous amount of capital has flowed into private equity. Private equity, like any inefficient space, there's just a huge dispersion between the results good managers get from what bad managers get. It's sort of the opposite of the bond universe where there might be a half-point difference between best and worst. There's a 15-point difference, 15 points IRR between the best managers and the worst managers.”— Royce Yudkoff
Challenges in the Private Equity World · p. 23
Economics & Markets · Strategy & Decision Making
DUR_CONTEXTUAL
15-point IRR spread in PE vs. 0.5 in bonds
“These businesses are hard to find because it's a very inefficient mechanism by which these businesses are traded. So what search fund LPs do is they will form a group and each pitch in a little bit of money to fund a searcher going out to look for a business to buy, vet it, negotiate it. If they like the business, they have a right to put in a piece of the capital like a private equity investment.”— Royce Yudkoff
An Overview of Search Funds · p. 2
Business & Entrepreneurship · Strategy & Decision Making · Economics & Markets
DUR_ENDURING
Staged capital deployment reduces risk
“We pull into these small towns. There are these absolutely nondescript, unknown businesses where the owners are pulling out $1, $2, $3, $4 million a year and no one has a sense of that. But the margins in these businesses that we've been describing to you typically run 20% to 30% of sales. Would be kind of at the normal range we expect to see. Some higher, rarely lower.”— Royce Yudkoff
The Best Example of a Student Acquisition · p. 27
Economics & Markets · Business & Entrepreneurship
DUR_ENDURING
Hidden prosperity in nondescript locations
“The soldiers particularly go on and explain when we're in combat, we're in combat for just a little bit of time. We'll spend years training for those few minutes of combat. When we do this, the kind of stress is permanent. We're responsible for other employees all the time and we don't really train for it. Except in the courses that Royce and I teach. So it's sort of this really interesting juxtaposition of rules that I find really fascinating.”— Rick Ruback
Most Memorable Day · p. 28
Psychology & Behavior · Leadership & Management
DUR_ENDURING
Permanent vs. acute stress: different courage
Frameworks (2)
Search Fund Option Structure
Staged Capital Deployment for Business Acquisition
A three-stage capital deployment framework that provides asymmetric optionality: fund discovery, evaluate opportunity, optional investment in acquisition. Minimizes risk through staged commitment while maintaining upside participation.
Components
- Fund Search Phase
- Evaluate Opportunity
- Optional Acquisition Investment
Prerequisites
- Network of potential LPs
- MBA or equivalent training
- 6-24 months operating capital
- Industry search focus defined
Success Indicators
- 100+ businesses reviewed
- 3-5 LOIs submitted
- Clear thesis articulation
- LP interest validated
Failure Modes
- Search fatigue after 18+ months
- Insufficient LP network
- Unclear target profile
- Forced selection from limited pipeline
Recurring Revenue Business Assessment
Four-Part Test for Defensible Small Business Moats
A diagnostic framework for evaluating whether a small business has durable competitive advantages through recurring customer relationships. Focuses on automatic repurchase behavior, switching costs, value-not-price dynamics, and performance metric focus.
Components
- Test for Automatic Repurchase
- Quantify Switching Costs
- Assess Value-Not-Price Dynamics
- Identify Performance Metric Focus
Prerequisites
- Customer list access
- Historical renewal rates
- Ability to interview customers
- Understanding of customer operations
Success Indicators
- 90%+ annual customer retention
- Customers can articulate value metrics
- Switching discussion reveals high costs
- Price as tertiary consideration
Failure Modes
- Mistaking repeat for recurring
- Customer focus on price indicates commodity
- High churn despite high satisfaction
- Contractual lock-in masking weak value
Mental Models (11)
EBITDA Multiple Valuation
EconomicsValuation methodology expressing enterprise value as multiple of earnings before interest, taxes, depreciation, and amortization. Lower multiples indicate better value if business quality is constant. Small enduringly profitable businesses trade around 4x EBITDA due to market inefficiency from succession crisis and lack of institutional interest.
In Practice: Core valuation framework for search fund businesses
Demonstrated by Leg-ry-001
Price Insensitivity from Asymmetric Stakes
EconomicsWhen service cost is tiny fraction of total cost and service failure consequences are catastrophic, price becomes tertiary consideration. Customers optimize on reliability and outcomes rather than price. Creates durable pricing power for service providers.
In Practice: Explanation of why window washing and pipe threading businesses have pricing power
Demonstrated by Leg-ry-001
Downside Protection Through Entry Price
EconomicsPurchasing assets at or near valuation floor eliminates multiple compression risk and creates margin of safety. When combined with conservative leverage, creates highly resilient capital structure. Protection comes from entry discipline rather than asset growth.
In Practice: Comparison of search fund risk profile vs. traditional private equity
Demonstrated by Leg-ry-001
Natural Monopoly from Geography Plus Small Market
EconomicsWhen market size is too small to support multiple competitors and geographic constraints make competition impractical, natural monopoly emerges. Key insight: monopolist must maintain pricing discipline to avoid inviting competition. Geographic constraint plus market size creates self-enforcing moat.
In Practice: Castronics pipe threading business in remote Nebraska
Demonstrated by Leg-ry-001
Diminishing Returns on Customer Acquisition
EconomicsFirst customers acquired have best economics: highest willingness to pay, lowest acquisition cost, longest tenure. Each subsequent customer cohort has worse economics. Growth therefore dilutes average customer quality and reduces recurring revenue percentage. Fastest growth often produces worst marginal economics.
In Practice: Explanation of why growth creates risk in small businesses
Demonstrated by Leg-ry-001
Operating Leverage and Revenue Sensitivity
EconomicsWhen costs are largely fixed, revenue changes flow disproportionately to profit. A 20% revenue decline may eliminate 90-100% of profit if cost structure cannot flex. Creates concentrated risk in businesses with regulatory or technological disruption exposure. Inverse of the principle that drives high margins in good times.
In Practice: Warning about healthcare reimbursement risk
Demonstrated by Leg-ry-001
Real Options and Staged Investment
Strategic ThinkingStructuring investments in stages creates option value: pay small amount for right to make large inv
In Practice: Search fund LP investment structure
Demonstrated by Leg-ry-001
Inversion: Why Is This Business Small?
Decision MakingRather than asking 'why is this business good?', invert to 'why is this business small?'. Answer reveals whether size is from market constraint (good) or business weakness (bad). Diagnostic question separates attractive constrained markets from unattractive constrained businesses.
In Practice: Framework for evaluating small business quality
Demonstrated by Leg-ry-001
Loss Aversion in Career Risk
PsychologyCareer risk from visible failure outweighs potential gains from cost savings.
In Practice: Window washing business switching costs
Demonstrated by Leg-ry-001
Chronic vs. Acute Stress Tolerance
PsychologyTwo fundamentally different stress profiles: acute high-intensity stress for brief periods vs. chronic moderate stress indefinitely.
In Practice: Military students discussing entrepreneurial fear
Demonstrated by Leg-ry-001
Leverage Amplification of Returns
MathematicsWhen return on assets exceeds cost of debt, leverage amplifies equity returns. F
In Practice: Mathematics of search fund returns
Demonstrated by Leg-ry-001
Connective Tissue (2)
Mining ore grades and customer acquisition economics
Rick Ruback draws explicit parallel between mining economics and customer acquisition: 'You get your most valued customers first, that's like the coal near the top of the ground. With each increase in volume, you're digging deeper into that mine and your costs are going up and you're less valuable.' In mining, richest ore deposits are extracted first; as miners go deeper, ore grades decline and extraction costs rise. In business growth, easiest and highest-value customers are acquired first. Later customers require more effort, accept lower margins, or generate less lifetime value. The parallel reveals why growth can destroy value: each marginal customer has worse economics than the last.
Discussion of why growth creates risk in small businesses
Combat stress duration vs. entrepreneurial stress permanence
Former military students explain that combat stress, while intense, is brief and preceded by years of training for those specific minutes. Entrepreneurial stress of employee responsibility is permanent and largely untrainable. The parallel reveals two types of courage: acute physical courage for brief high-intensity situations vs. chronic psychological courage for sustained responsibility. Military trains for acute; business requires chronic. The insight challenges conventional hierarchies of courage and suggests entrepreneurship demands a fundamentally different stress tolerance profile than physical danger professions.
Discussion of what students find scary about entrepreneurship
Key Figures (1)
Jennifer Braus
6 mentionsSearch Fund Entrepreneur, CEO of Systems Design West
Engineer from American Midwest who attended Harvard Business School and became search fund entrepreneur.
- Began outreach to approximately 3,000 small business brokers
Glossary (1)
enduringly profitable
VOCABULARYConsistently generating profits year after year over decades
“These businesses are enduringly profitable, successful small firms but there's no natural successor.”
Key People (1)
Patrick O'Shaughnessy
Host of Invest Like The Best podcast
Concepts (2)
EBITDA
CL_FINANCIALEarnings before interest, taxes, depreciation, and amortization; a measure of operating profitability
Senior Debt
CL_FINANCIALLoans with first priority claim on assets in bankruptcy; typically secured by collateral
Synthesis
Synthesis
Migrated from Scholia