Notes from the deal desk on underwriting, market structure, and the diligence questions that actually move a thesis.
A day-by-day plan for venture teams with two weeks before a term sheet decision: verify the metrics, call the right customers, size the market, and write it down.
Deal StructuringHow lower middle-market buyers can use earnouts, seller notes, and rollover equity to price the questions diligence could not answer, without inviting disputes.
Diligence & UnderwritingYou do not need to read code to size technical debt. Six questions non-technical buyers can ask in a software deal, and how to turn the answers into model adjustments.
Buy-and-BuildThe LOI multiple is only part of what an add-on costs. How to screen bolt-ons on integration cost, attrition, bandwidth, and key-person risk using an effective multiple.
Independent SponsorsIndependent sponsors who win proprietary deals treat origination as a system. A practical approach to thesis, target universe, tiering, outreach, and pipeline tracking.
Financial ModelingDeferred revenue can shift the effective price of a software acquisition. How it gets treated, where it moves before close, and what to settle before the LOI.
Diligence & UnderwritingIn many founder-owned vertical software businesses, maintenance revenue is the asset being bought. Five tests for its durability, pricing headroom, and migration risk.
Diligence & UnderwritingThe standard reference call confirms the CIM instead of testing it. Five ways to restructure the calls already happening so they actually reveal renewal friction and vendor risk.
Diligence & UnderwritingThe EBITDA add-backs are the well-covered part of founder-owned diligence. The red flags that surface late have nothing to do with the income statement.
Diligence & UnderwritingEvery vertical market software CIM asserts high switching costs, and almost nobody tests the claim before underwriting it. Five signals that are actually measurable in diligence.
Financial ModelingThe working capital peg looks like boilerplate and is one of the few deal terms that reliably gets renegotiated after signing. Five inputs that actually decide who owes what at true-up.
Sell-Side AdvisoryThe same set of gaps slows down most lower middle-market sale processes. A checklist for what should be ready before a single buyer conversation starts.
Financial ModelingWhen a true comp set has two or three names in it, false precision is worse than an honestly wide range. A method for building a defensible valuation view anyway.
Diligence & UnderwritingA follow-up to our piece on underwriting vertical market software. Net revenue retention was built for horizontal SaaS. Here is what to look at instead in a true vertical market.
Diligence & UnderwritingA follow-up to our piece on underwriting vertical market software. A framework for telling genuine concentration risk apart from concentration that is actually evidence of a durable moat.
Corporate DevelopmentCorporate development teams often screen for strategic fit first and financial discipline second. That ordering is backwards, and it shows up in the deals that get championed but never close.
Independent SponsorsIndependent sponsors need a capital-partner-ready diligence package without the analyst bench a fund has. Here is what actually needs to be ready, and in what order.
Investment CommitteeThe memos that survive an investment committee meeting are the ones that anticipated the hardest question in the room before anyone had to ask it.
Diligence & UnderwritingThe gap between reported and adjusted EBITDA is where a surprising amount of deal risk hides. A framework for telling a legitimate addback from a negotiating position.
Financial ModelingJunior analysts spend the most modeling time on operating assumptions. In most lower middle-market deals, leverage structure and multiple assumptions do more work than the operating case.
Market ResearchTop-down market research reports are built for consumer categories and large horizontal markets. Niche B2B software needs a bottom-up count instead.
Screening & AnalysisA confidential information memorandum is written to be persuasive, not neutral. Here is what to look for in the first pass, and what almost always gets left out.
Deal SourcingMost buyer lists get built backwards, starting from who the banker already knows instead of who actually has a reason to pay up. Here is a better method.
Diligence & UnderwritingWhy the horizontal SaaS playbook misprices growth, customer concentration, switching costs, and market size in vertical market software, and what to underwrite instead.
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