Operator essays.
Notes on revenue operations, GTM strategy, capital allocation for searchers and seed founders, and the diligence behind operator-led acquisitions.
April 20, 2026
3 min read
CapitalWhy I Don't Compete With The Searchers I Back
When a deal a backed searcher brings me fits my own buy-box, I co-invest with them rather than compete for it. Here is why that policy is structural, not generous.
April 10, 2026
3 min read
AcquireThe Post-Close 100-Day Plan For An SMB Acquisition
The first hundred days after close determine the next two years. Here is the operating plan I run, designed to land trust before changing anything.
April 1, 2026
2 min read
ConsultingBuilding A Pipeline Review That Surfaces Decisions
Most pipeline reviews are status meetings. Rebuild them around the deals where leadership intervention changes the outcome.
March 20, 2026
3 min read
CapitalRoll-Up Backing: What Makes A Platform Investable
Most roll-up pitches sound the same. The platforms that actually work share specific structural traits that get under-discussed in the pitch.
March 10, 2026
3 min read
AcquireCustomer Concentration Risk In Commercial Services
Commercial services businesses often have heavy customer concentration. Here is how I evaluate whether the concentration is a risk or a feature.
March 1, 2026
2 min read
ConsultingPricing Strategy Without Market Data
New products, new categories, and early-stage companies cannot benchmark pricing. Here is a value-based method that works without comparable data.
February 20, 2026
3 min read
CapitalHow To Evaluate A Search Fund Principal Before You Commit
The aggregate returns of the search fund asset class do not protect you on a single bet. Here is the diligence I do on the principal before committing capital.
February 10, 2026
3 min read
AcquireEarn-Out Structures That Actually Work
Earn-outs solve real valuation gaps when designed well, and create resentment on both sides when designed poorly. Here is what I have learned about getting them right.
February 1, 2026
2 min read
ConsultingNDR vs GDR: What The Difference Actually Tells You
Net revenue retention is the headline. Gross revenue retention is the diagnostic. The gap between the two is the most useful number on your customer dashboard.
January 20, 2026
3 min read
CapitalHealthcare Technology: A Capital Allocator's Framework
Healthcare technology is one of the most demanding categories for an early-stage investor. Here is the framework I use to separate real opportunities from category-risk traps.
January 10, 2026
3 min read
AcquireFinancing An Acquisition Without A Search Fund
There are more ways to finance an SMB acquisition than the traditional search fund route. Here is how I think about the capital stack on a self-funded deal.
January 1, 2026
2 min read
ConsultingA CRO's First 90 Days: An Operating Cadence Playbook
The first ninety days of a chief revenue officer's tenure determine the next two years. Here is what the operating cadence should look like, week by week.
December 20, 2025
3 min read
CapitalRevOps Tooling As A Venture Category
Revenue operations tooling is one of the most under-appreciated venture categories of the next five years. Here is what makes it interesting and what I look for in deals.
December 10, 2025
3 min read
AcquireDistressed SMB Acquisitions: When The Discount Is Real
Distressed acquisitions look like bargains until they are not. Here is how I separate the discounts that come from operating fixability from the ones that do not.
December 1, 2025
2 min read
ConsultingCapacity Modeling For Sales: The Real Math
Sales capacity is not headcount times quota. It is a four-input model that determines what a team can credibly produce, and where the binding constraint lives.
November 20, 2025
3 min read
CapitalThe ETA Capital Stack: Equity, Mezzanine, SBA, Seller Financing
Most ETA acquisitions use a multi-source capital stack. Here is how each layer works, what the trade-offs are, and how I think about which mix fits which deal.
November 10, 2025
3 min read
AcquireHealthcare Services Acquisition: Regulatory Diligence In Plain English
Healthcare services acquisitions have regulatory complexity most acquirers underestimate. Here is the plain-English version of what to look for, and why it matters before close.
November 1, 2025
2 min read
ConsultingThe Unit Economics Of A B2B SaaS Sales Motion
CAC, LTV, payback, magic number. The four ratios most B2B SaaS companies misread. Here is the math and what each one actually tells you.
October 20, 2025
3 min read
CapitalSearch Fund Economics From The LP Side
Most search fund pitches are written for searchers and institutional LPs. Here is the LP-side math, including the parts that often get glossed over in the pitch.
October 10, 2025
3 min read
AcquireThe Case For Keeping The GM Post-Close
Most acquirers replace the existing operator within a year of close. I think that is usually the wrong move. Here is when keeping the GM is the right answer.
October 1, 2025
2 min read
ConsultingWhy Most QBRs Are Theater (And How To Rebuild Them)
Quarterly business reviews are usually recap meetings dressed as decision meetings. Rebuild them around the questions data could not answer.
September 20, 2025
3 min read
CapitalVertical SaaS: The Next Operator-Led Wave
Horizontal SaaS won the last decade. The next decade is being built by operators who pick a single vertical and own it end-to-end. Here is what that looks like.
September 10, 2025
3 min read
AcquireWorking Capital Traps In SMB Acquisitions
Most first-time SMB acquirers miss working capital in the deal structure. The post-close cash flow problem that follows is avoidable, and expensive.
September 1, 2025
2 min read
ConsultingFrom Founder-Led Selling To Repeatable Execution
Every Series A company eventually has to move past founder-led selling. Most rebuild the wrong things first. Here is the right sequence.
August 20, 2025
3 min read
CapitalWhen To Write A Small Check Versus No Check
Most of the founders I meet do not get a check from me. The decision rule between a small yes and a polite no is more specific than most founders expect.
August 10, 2025
2 min read
AcquireWhat Owner-Operator Sellers Actually Want
Most acquirers diligence the business and pitch the price. The sellers I have closed with were paying attention to something else entirely.
August 1, 2025
2 min read
ConsultingRenewals As An Operating Motion, Not A Finance Event
Most companies treat renewals as a back-office event. Treat them as an operating motion with named ownership and an instrumented cadence.
July 20, 2025
3 min read
CapitalAI-Native Operator Tools: Where I Am Deploying Seed Capital
AI-native tools are reshaping how operators run companies. Here is the specific category I am investing in and the questions I ask before writing a check.
July 10, 2025
2 min read
AcquireSearch Funds vs Operator-Led Acquisition: The Structural Differences
Both models acquire small businesses, but they make different promises to the seller and behave differently after close. Here is what the difference actually looks like.
July 1, 2025
2 min read
ConsultingThe MEDDICC Trap: When Qualification Becomes Theater
MEDDICC works as a qualification framework when reps actually use it. It collapses into theater when leadership treats it as a forecasting input.
June 20, 2025
3 min read
CapitalThe Case For Backing Operators Over Funds
Most LP capital flows to fund managers. The operator-direct model produces a different return profile and a different relationship. Here is what I have learned by writing checks both ways.
June 10, 2025
3 min read
AcquireThe MSP Buy-Box: What Recurring Revenue Actually Tells You
Managed service providers look great on the surface because of recurring revenue. The diligence questions that matter live underneath the MRR number.
June 1, 2025
2 min read
ConsultingPipeline Coverage: A Math-First Framework
Pipeline coverage ratios are usually theater. Replace them with a math-first model that accounts for stage conversion, deal size, and time-to-close.
May 20, 2025
3 min read
CapitalCo-Investing With Searchers: Structures That Align Incentives
When I co-invest with a searcher, the deal structure matters as much as the underlying business. Here is what I have learned about getting it right.
May 10, 2025
2 min read
AcquireNEMT Acquisition: What Brokers Won't Always Tell You
Non-emergency medical transportation is one of the strongest verticals for operator-led acquisition, but the diligence has unique traps. Here is what to look for.
May 1, 2025
2 min read
ConsultingWhat Deal Desk Should Actually Do
Most deal desks slow good deals while waving through bad ones. The right design governs the plan, not every transaction.
April 20, 2025
3 min read
CapitalSearch Fund LP Investing For Non-Institutional LPs
Search fund LP investing is one of the more interesting asset classes for individual LPs. Here is how I think about it from both sides of the table.
April 10, 2025
2 min read
AcquireHow To Evaluate A Multi-Unit Restaurant Chain Before You Buy
Multi-unit independent restaurants are a different acquisition than a single-unit operator. Here is the diligence framework I use, and the traps I avoid.
April 1, 2025
2 min read
ConsultingHow To Set Quotas Without Historical Data
New segments, new products, and Series B teams have no historical attainment to anchor on. Build quota from capacity instead. Here is the method I use.
March 20, 2025
3 min read
CapitalWhat I Look For In A B2B SaaS Founder's First Deck
Most pitch deck advice is generic. Here is the specific signal I look for, the slides that change my mind in either direction, and the words that always show up in the decks I fund.
March 10, 2025
2 min read
AcquireDiligence Questions That Actually Matter For Residential Services
Most residential services diligence is a financial review with a CRM appendix. The questions that decide whether the deal works live somewhere else entirely.
March 1, 2025
2 min read
ConsultingDesigning Sales Compensation That Aligns With Strategic Priorities
Most comp plans pay the field for behaviors leadership did not intend. The redesign starts with what you actually want, then builds backward into the math.
February 20, 2025
2 min read
CapitalWhy Operator-Led Capital Matters For Early-Stage SaaS
The operating decisions that determine whether a SaaS company makes it to Series B happen before the funds are deployed. Here is what operator-led capital actually changes.
February 10, 2025
2 min read
AcquireThe Case For Ten-Year Holds In SMB Acquisition
Most search funds run a five-year clock. I think that math is wrong for the kind of small businesses worth buying. Here is why I commit to ten.
February 1, 2025
2 min read
ConsultingWhy Forecast Accuracy Stalls Below 60%
Sales forecasts plateau in the low fifties for predictable structural reasons. The fix is bottom-up unit modeling and an evidence-based stage rule.
January 20, 2025
2 min read
CapitalThe Small-Check Strategy: Why $25k Actually Matters
A small check can do real work for a founder when it comes from someone who has built the systems they are trying to build. Here is how I think about sizing seed checks.
January 10, 2025
2 min read
AcquireWhy I Won't Buy A Business Below $750k EBITDA
The $750k EBITDA floor is the firmest line in our buy-box. Here is the operating math behind why I will not move it, no matter how good the asking price looks.
January 1, 2025
2 min read
ConsultingThe RevOps Operating System: A Five-Layer Framework
Pipeline hygiene, compensation, pricing, renewals, and operating cadence. The five sequential layers of a working revenue operations system.