Close in ~30 Days: How Andrew Wilkinson & Tiny Streamline Diligence Without Cutting Corners

Close in ~30 Days: How Andrew Wilkinson & Tiny Streamline Diligence Without Cutting Corners is my plain-English playbook for moving from first call to funds flow fast.
I’ll show you how I compress diligence without skipping what matters.
I’ll lay out the exact docs, cadence, owners, and timelines I use.
I’ll keep every sentence on its own line and give you copy-paste checklists you can use today.

The 30-Day Mindset: Speed Plus Certainty

I never trade certainty for speed.
I trade noise for signal.
The trick is to verify the few things that drive cash and risk, and kill everything else.
For ruthless focus while you run this, see our blog post: Delete 95% of Your Email.

What “Streamline Diligence” Actually Means

Streamlining is sequencing and scope control, not skipping.
I front-load the Vital 20% and time-box everything else.
I set owners, SLAs, and one communication thread so nothing drifts.
For clean, decisive writing, read: I Don’t Respond to Long Emails.

Pre-LOI vs Post-LOI: Draw the Line Early

Pre-LOI, I ask for a tight teaser and the Vital 20% data pack.
Post-LOI, I run focused sprints across finance, legal/IP, tax, tech, HR, and commercial.
I calendarize deliverables on day one with dates and names next to each item.

The Vital 20% Data Room (Upload First)

Financials.
TTM P&L tied to bank, last 3 fiscal years, cash→accrual bridge, labeled add-backs.
Customers.
Top-20 by month (36 months), cohorts with GRR/NRR, pricing history.
Working Capital.
AR/AP aging, inventory or deferred-revenue schedules.
Legal/IP.
Key contracts with change-of-control, IP assignments, cap table.
Ops/People/Tech.
Org chart, top 10 SOPs, access hygiene/SSO, backups, RTO/RPO, incident log.

Financial Tie-Outs in 48 Hours

I reconcile revenue to bank deposits.
I map the cash→accrual bridge on one page.
I evidence every add-back with a receipt and a one-sentence rationale.
Quality beats volume.
For a sanity check on simplicity, skim: Are You Insane.

Unit Economics, Cohorts, and Price Power

I underwrite contribution margin, CAC, payback, and LTV by channel.
I read 12–36 month cohort curves and look for dips with fixes.
If you raised price and NRR stayed ≥100%, I stretch cash at close.
For narrative that lands without fluff, read: Never Tell, Always Storytell.

Working-Capital Peg Without Drama

We price cash-free, debt-free with a normalized NWC peg from 12 monthly snapshots.
We define inclusions and exclusions in one paragraph.
We agree to a dollar-for-dollar true-up at close.
It’s the quiet paragraph that moves six figures.

Legal & IP: Make It Boring

I want clean IP assignments, a current cap table, and change-of-control items listed early.
I cap indemnities, set a modest escrow, and keep survival periods reasonable.
Boring legal is fast legal.

Tax & Compliance: No Skeletons

I scan sales tax/GST/VAT, payroll, and privacy posture.
I list jurisdictions and filings with any clean-up plan in two bullets.
Surprises here stall otherwise perfect deals.

Tech & Security One-Pager I Actually Read

Give me architecture, key vendors, access hygiene/SSO, backups and RTO/RPO, incident history, and single-point-of-failure risks.
If one engineer is central, we design a paid transition to spread keys and document the stack.

Customer Calls: Small, Scripted, Credible

I do a handful of short calls post-LOI.
I focus on stickiness, switching costs, and price headroom.
I brief customers with a one-page continuity note so the call builds confidence, not drama.

Vendor & Platform Risk: Map It, Don’t Hand-Wave It

I list tier-1 vendors, contract terms, and backup paths.
If you depend on one platform, I want mitigations and a 90-day action plan.
Name the risk and show the fix.

Inventory and Deferred Revenue: The Two Quiet Gotchas

In product businesses, I want lower of cost or NRV, obsolescence reserves, and turns by SKU.
In SaaS/services, I treat deferred revenue as a real liability with clean recognition.
I price truth, not optimism.

Structure for Speed: Cash First, Clean Terms

I bias to more cash at close and a small, short escrow.
I avoid long, murky earnouts.
If we use one, it’s ≤18 months, ≤20–25%, one metric, with locked governance.

Indemnities, Caps, and Survival Periods

I keep general reps short, fundamental reps longer, and fraud uncapped.
I use a basket or deductible to avoid nickel-and-diming.
I match escrow size and term to actual risk.

Communication Hygiene That Halves the Timeline

One owner per domain.
One live checklist.
One weekly summary.
One email thread.
Short, numbered messages win.
For tone and cadence, re-read: I Don’t Respond to Long Emails.

The 30-Day Diligence Calendar (Day-by-Day)

Days 1–3.
Kickoff, calendar, Vital 20% live, cash→accrual bridge delivered.
Days 4–10.
Financial and legal/IP sprints, customer call list locked.
Days 11–20.
Tech/security review, WC peg agreement, customer references, draft SPA.
Days 21–30.
Final markups, funds-flow, Day-1 comms, and KPI cadence kickoff.
For rhythm, see: 02: Journaling With AI.

Red Flags I Fix Fast (Or Walk)

Trust-me add-backs.
Hidden liabilities.
Vague EBITDA or revenue recognition.
Off-platform payments and promo-propped demand.
If it’s fixable, show the fix now and I’ll price it fairly.

Templates and Tools You Can Copy

Four-line intro email.
What you are, TTM revenue/EBITDA, retention/concentration, preferred terms + 30-day close.
Plain-English LOI.
Guardrails binding, economics non-binding, tight peg paragraph, modest escrow.
Vital 20% checklist.
Financials, customers/cohorts, WC, legal/IP, ops/tech on one page.
For taste in capital allocation and simplicity, skim: A $3,600 Keyboard and a $66 Million Dollar Investment.

Post-Close Day-1 and 90-Day Transition

I keep teams intact, set weekly KPIs, and remove distractions.
I publish a Day-1 memo for staff and customers.
I make the first 90 days boring on purpose.
Learn more about how I think on the About page, the Newsletter, and the Podcast.

Copy-Paste: Diligence “Vital 20%” Checklist

• TTM P&L tied to bank and 3-year history.
  
  
• Cash→accrual bridge with one-sentence add-backs and receipts.
  
  
• Top-20 customers by month (36 months) plus GRR/NRR cohorts.
  
  
• AR/AP aging and inventory or deferred-revenue schedules.
  
  
• Key contracts with change-of-control, IP assignments, cap table.
  
  
• Org chart, top 10 SOPs, access hygiene/SSO, backups, RTO/RPO, incident log.
  
  

FAQs

Can we truly close in ~30 days without cutting corners.
Yes if your Vital 20% is ready, owners are assigned, and communication is tight.

Do I need audited financials to get an LOI.
No.
I need reconciled statements tied to bank and a clean cash→accrual bridge.

What’s the single fastest way to speed diligence.
Publish the Vital 20% on day one and answer in one email thread with named owners.

How do you handle working-capital fights.
We set the peg from 12 monthly snapshots, define inclusions/exclusions, and true-up dollar-for-dollar.

Will you accept an earnout if I want a higher headline.
Only if it’s short, small, one metric, and governance is locked.
Cash plus a modest escrow is usually better.

How many customer calls do you make.
As few as needed to confirm stickiness and price headroom.
Quality beats quantity.

What kills deals late.
Hidden liabilities, vague recognition policies, trust-me add-backs, and platform risk with no plan.

How big is a typical escrow.
Often 5–15% for ~12 months with a cap and a small basket.

What if my founder role is still central.
We price the risk and write a short, paid transition with clear deliverables.

How should I structure my teaser deck.
Eight slides: snapshot, 3-year + TTM financials, unit economics, cohorts/retention, customer mix, moat, org, risks + your ask.

How do I keep my team calm during diligence.
Use a Day-1 memo, clear roles, weekly KPIs, and minimal disruption to routines.

Conclusion

Close in ~30 Days: How Andrew Wilkinson & Tiny Streamline Diligence Without Cutting Corners is about sequencing the right checks, locking a clean peg, and keeping communication painfully clear.
Run the Vital 20%, verify cash and unit economics, keep legal boring, and you can trade complexity for cash at close while moving fast.
Get Your Copy of Never Enough at https://www.neverenough.com/

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