The paper of record,
for people who build.
Our specialty: providing strategic counsel to stakeholders and partnering with outstanding teams in building world-class businesses, creating new revenue streams, and generating meaningful returns & long-term value.
Jennings Cooksey is a principal, counsel, and builder of businesses. The order changes by the day; the standard does not. For a decade he has built, capitalized, and papered more than $1 billion in projects from the principal's chair. Before that, he sold his own family's company. JMTD Group exists for the engagements where that matters: founders at the start of the build, founders at the point of sale, sponsors at the point of capitalization, and builders pushing us to the new frontiers of energy and infrastructure. Not counsel across the table. Counsel from your side of it — he has signed the guaranty himself.
The deal & the build.
A practice reveals itself in what it takes on next. The forward calendar runs two books. In the first, companies change hands: middle-market M&A from either side of the table, run like a campaign. In the second, buildings leave the ground: formation through exit, governed by land, steel, capital stacks, and construction risk. Both are drawn below. Both end at the same gilt mark — the announcement. And one engagement runs through both books at once: the subscription, standing counsel between editions (Article VI). If your lawyer has never negotiated a GMP contract, a JV waterfall, or a founder's sell-side, start the conversation below. He speaks promote, peg, and critical path.
Sell-Side M&A
The exit is the last structure you build — and the one you only build once. He has led founder sell-sides at ~15–19× EBITDA: running the process, controlling diligence, and negotiating like the proceeds are his. Because once, they were. That includes the day a strategic comes for your platform.
Buy-Side & Board
Corporate development from the seat where the vote happens. He built and ran an acquisition program end to end — sourcing, screening, structuring, closing — and has served as director, corporate secretary, and board member. Buy-side counsel that thinks in integration plans, not just purchase agreements.
Capital Formation
JV structures, waterfalls and promotes, and guaranty frameworks across institutional capital classes — REIT, private equity, and family office.
Construction Risk
GMP contract architecture, subcontractor risk allocation, and draw mechanics for projects where schedule is the product.
Ground & Grid
Site acquisition, entitlements, special districts, and the regulatory sequencing that decides whether a project breaks ground on time.
General note: force majeure does not cover optimism. Draft accordingly.
One counsel. Deal-team throughput.
Practice areas: mergers and acquisitions, real estate development, outside general counsel and strategy.
Cooksey runs the practice on an AI-assisted apparatus with a decade of his own deal work as its training ground. The machines draft, cross-reference, and pressure-test. He reviews, judges, and signs. These are methods of practice, not software for sale. A generation of AI-native firms now moves standardized paper at remarkable speed; this practice exists for the matters where judgment, not volume, is the product — run at the tempo those firms taught the market to expect.
Mergers & Acquisitions
Founder exits run end to end: data room staged, disclosure schedules built, and the negotiation war-gamed before the first call. On the buy side, acquisitions underwritten the way a board needs them — the model and the industry study delivered with the purchase agreement, not instead of it, through the first hundred days.
Real Estate Development
From raw dirt to record title on a multi-state program: the PSA cycle, entitlements and permit successions, joint-venture waterfalls negotiated sponsor-side, and construction facilities papered with the GMP as one system — by counsel who has signed the guaranty himself.
Outside General Counsel & Strategy
A standing seat between the principal and the specialists: regulatory calendars, board materials, capital strategy, and the judgment call at the moment it is needed — scoped to the seat, not the clock. The full offer is Article VI, The Subscription.
Building with the End in Mind
Every venture formed the way it will someday be sold: clean structure, clean records, waterfall math that survives diligence, and a cap table that can take a buyer's review cold. The tombstone is designed before the foundation is poured.
Client files are segregated by client inside the apparatus; one client’s material is never used in another client’s work. No client material trains any model. Counsel reviews and signs every output before it leaves the practice. The engagement letter states the data terms in writing.
Intake
Documents in. Standardized summary, risk flags, and gap list out.
Desk Work
The matter routes through playbooks built on his own precedent.
Adversarial Audit
A second system attacks the first draft. Weak reasoning dies here.
Counsel Signs
He reviews everything, decides everything, and signs every page.
Claims about method are cheap, so what follows is evidence. First, the operating tempo — with the basis for each figure stated. Folded beneath it, for those who want the detail: a live sample of the practice's intake output on a fictional matter, and the Matter Router — open it, bring your deal type, and watch the apparatus engage.
Exhibit A · Deal Intake · Synthetic Matter● Folded — open to render
The Matter Router · select a matter · watch the practice engageEvery route ends the same place: counsel signs
General note: Nothing on this page is legal advice or an engagement.
Chapters & counterparties
Platforms built, buyers closed against, boards served on: the register of chapters.
Platforms built, buyers closed against, benches served on, and uniforms worn. Every plate below is a chapter, not a client list.
Watermark CompaniesPlatform · MP & GC
Canvas® CommunitiesBTR Brand · 6 States
Rhino ResidentialBuilder · Co-Owner
Rollins, Inc.Exit Buyer · NYSE: ROL
TerminixCopesan Buyer · 2018
U.S. Dist. Ct. · M.D. Fla.Federal Clerkship
CSXLaw Clerk · Rail
J.B. HuntManager · Intermodal
Finer Days HealthcareHealthcare · Board
UF Levin College of LawJ.D. · Business Law
U.S. House of RepresentativesCongressional Asst. · '10
Rockies Venture ClubAngel · 2022–25Names and marks shown to identify chapters of the record; all marks remain their owners' property. The McCall Service plate is set in the heritage style of the pre-2021 family company — not the successor brand.
The tombstones
Closed transactions: founder exits, JV formations, construction facilities.
Bankers frame theirs in lucite. These hold the wall. Closed matters and standing structures — confidential terms omitted, nothing invented.
and acted as counsel to the seller — as EVP & General Counsel
Jennings Cooksey
Jennings Cooksey
Representative matters from public or client-published outcomes. Confidential counterparties and terms omitted. Prior results do not guarantee a similar outcome. Certain strategy and advisory services described herein are business services, not legal services; engagement letters state which is which.
Jennings Cooksey represented us when we sold McCall Service in 2020. He is a highly skilled, very detailed attorney, familiar with all aspects of acquisitions. He was instrumental in ensuring we received the greatest return on our investment.
Jennings was outside general counsel for us for a couple years and is now a partner in and co-owner of our business. That speaks for itself.
During the sale of our family business, Jennings Cooksey provided great insight and a wealth of knowledge. He was responsive and well surpassed my expectations in his representation.
If you can do what you do best and be happy, you're further along in life than most folks.
How the career carries
Army officer, federal clerk, private practice, EVP and GC of a founder-owned company through its sale, build-to-rent developer.
Each stage carries into the next. Logistics taught systems. The clerkship taught rigor. Private practice taught the documents. The principal seat taught what the documents cost.
U.S. Army Officer · J.B. Hunt
Commissioned officer, Transportation Corps; then managed $3–10M logistics accounts across the Southwest, Mexico, and Canada. Systems under pressure, at scale.
Federal Clerkship · M.D. Fla.
Law clerk to the Hon. Paul G. Byron. Drafted judicial orders on dispositive motions. UF Levin College of Law, J.D., business law focus.
Private Practice
Broad and Cassel, then Hopping Green & Sams — corporate, real estate development and financing, affordable housing and tax credits, infrastructure and project finance, special districts.
McCall Service · EVP & GC
GC, then EVP of Strategy and corporate development for the family services company. Built the M&A function, ran the process, and closed the exit to Rollins.
Watermark · JMTD Group
Managing Partner & GC of the Watermark / Canvas® / Rhino build-to-rent platform; co-owner of Rhino Residential. Selective principal-side practice through JMTD Group. Board member, Finer Days Healthcare. Former angel investor, Rockies Venture Club and Denver Angels.
By the matter, or by the month.
Engagement models: fixed-fee transactions, monthly outside general counsel, board and capital advisory.
Most of this paper records editions: a sale run, a venture formed, a facility closed. Some clients take the subscription instead — JMTD as standing outside general counsel to founders and sponsors, on call across everything the calendar carries. And because the principal's chair taught more than law, the subscription reads wider than a legal retainer.
Outside General Counsel
The first call, every time: contracts, negotiations, the dispute headed off before it files — a general counsel's judgment without a general counsel's headcount.
Board & Corporate Development
Director and corporate-secretary service, acquisition programs run board-side, and the vote prepared before it is called.
Capital & Strategy
Stack design, underwriting models, industry studies, the deck the money actually reads. Business advisory, plainly labeled — not every deliverable is legal work, and the engagement letter says which is which.
The Standing Brief
The practice’s intelligence engine, pointed at your market: a continuing intelligence brief on the capital, policy, and industry moves that change your next decision.
The next announcement is yours.
A thirty-minute working session on your actual transaction — no pitch deck, no associate. If he's not the right counsel for it, he'll tell you who is.
- Email · PracticeJennings@jmtdgroup.com
- LinkedIn/in/jenningscooksey
- SpecialtyM&A · Real estate development · Building with the end in mind
- FitFounders · Sponsors · Frontier builders
- ModeSelective · Principal-to-principal · No billable-hour theater
- PricingPriced like a principal: to the outcome, not the input, and certainly not my clock
- BaseDenver, Colorado · MSL 5,280'
as a matter of record only.
with counsel from its own side of the table.