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The CIO's Exit Playbook

How Technology Founders Sell Their Business for What It's Actually Worth

Most exit-planning books are written by consultants who have never bought a company. This one is written by an active buyer who reviews 10 to 15 IT services businesses per month and writes real checks. That is the entire reason it works.

Applied properly over 12 to 24 months, the framework in the Playbook reliably adds $300K to $500K to a $3M IT services business at exit. Not by growing the business, but by making its value visible to the right buyers.

$797 · Lifetime access · Excel + Notion included

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Wolfspire Solutions
David L. Lieske

The

CIO's Exit
Playbook
How Technology Founders Sell Their Business for What It's Actually Worth
Three decades in enterprise tech.
Now buying IT companies.
For a living.

What's inside

The Playbook is organized in four parts, following the natural sequence a founder moves through from "thinking about it" to "life after the sale." Each chapter is self-contained, so you can read straight through or skip to what's relevant right now.

Part 1

What Buyers Actually Pay For

  1. The Four Buyer Types
  2. The IT-Specific Multiples Framework (2.7-3x SBA anchor)
  3. Recurring vs Project Revenue (the multiple-doubler)
  4. The Documentation Premium
Part 2

Preparing Your Business for Sale

  1. Technology Stack Diligence Checklist
  2. IP and Documentation for Buyer Confidence
  3. Customer Concentration and Contract Structure
  4. Financial Hygiene and the Tax Return Trump Card
  5. Team Structure and Owner Dependency
  6. The 30-Day Owner-Dependency Sprint
Part 3

The Sale Process

  1. When to Sell vs When to Wait
  2. Finding the Right Buyer
  3. The IT-Specific CIM
  4. Diligence Survival Guide for Technical Founders
  5. Negotiating Multiples, Earn-outs, and Rollover Equity
Part 4

Post-Sale

  1. Transition Planning
  2. Life After the Sale

Sample: from Chapter 8, the Tax Return Trump Card

Excerpt

Every IT founder I know has been coached by a CPA to minimize taxes. Fair. Nobody wants to pay Uncle Sam more than necessary.

But here's the trap: your tax return is the ONE document SBA lenders and sophisticated buyers trust above all others. Internal P&Ls can be adjusted. Tax returns are IRS-verified. If your tax return shows $200K in reported income because you've aggressively minimized (owner comp through S-corp distributions, all vehicles business-titled, home office deductions, family members on payroll), the bank underwrites your sale at the tax-return number, not your adjusted EBITDA.

The gap between "what my CPA showed the IRS" and "what my business really earned" gets left on the table unless you can DEFEND your tax posture as an intentional strategy.

Important disclosure. Dave Lieske is not a CPA, tax attorney, or licensed financial advisor. The Playbook covers financial and tax strategy considerations from an operator's and active buyer's perspective. Educational content, not professional advice. Any tax, legal, or financial strategy referenced in the Playbook or on this site should be reviewed with a qualified CPA, tax advisor, or attorney before you act on it. Your specific situation may differ from the examples discussed.

What you get for $797

  • 17 chapters, ~50,000 words. Equivalent to $5,000+ of M&A advisor consulting hours packaged as a self-directed framework
  • Written from an active buyer's chair. Someone reviewing 10 to 15 IT services businesses per month
  • Companion Excel: IT-flavored EBITDA add-back tracker. The kind of tool M&A advisors bill $500/hr to build custom
  • Companion Notion workspace: Command Center dashboard plus a working template for every chapter, import-ready
  • Lifetime access, delivered instantly via Gumroad
  • All future updates included

Total value if hired out: roughly $8,000 in packaged expertise. Priced at $797 because the audience matters more than the margin.

The Notion workspace: the tool nobody else includes

The Notion companion turns the Playbook from a book you read into an operating system you work. A Command Center dashboard plus one working template per chapter: Buyer Research Log, Tax Strategy Defense, CIM Draft, Diligence Data Room, Negotiation Tracker, and 12 more. Import to Notion, fill in over 12 to 24 months, arrive at close with buyer-ready documentation already built.

If you're a founder who's been doing this for 20 years and is finally tired of doing it alone, the workspace is the part that changes the equation. You get the framework in the book AND the structured place to actually work it. Without hiring a $50K advisor to build the templates for you.

The 60-day proof-of-work guarantee

Read the Playbook and apply the framework for 60 days. If you complete the work and cannot identify at least $50,000 in legitimate EBITDA add-backs OR a clear multiple-improvement path worth more than the purchase price, email me and I'll refund your $797.

What "complete the work" means. Refund requests need documentation showing you actually worked through the framework:

  1. A filled-in EBITDA Add-Back Tracker with at least 10 entries (screenshot or Excel export)
  2. Either the completed Exit Prep Command Center OR at least 3 Notion chapter templates filled in with your business details
  3. A brief written description (200 words minimum) explaining what you tried, which frameworks you applied, and where the Playbook fell short for your specific business

Timeline. Requests must be submitted within 60 days of purchase. Qualifying refunds are processed within 5 business days.

Sole discretion clause. Wolfspire Solutions reserves sole discretion in determining whether documentation meets the requirements above. Refunds are one per customer across all Wolfspire products (bundle purchase counts as one). Not honored for customers who have publicly reviewed the product prior to requesting refund, or for customers with a documented history of refund requests across multiple digital products.

What this looks like in practice

Case Study

[Case study placeholder: Dave to add one anonymized example when identified. Format: MSP/cyber/ERP founder in [region] applied the [chapter] framework, identified $[X]K in legitimate add-backs OR restructured revenue framing, added $[Y]K to close price [Q] months later. Same business, materially different outcome.]

Get both. Save $297.

Playbook + Sale-Ready Toolkit Bundle

The Playbook ($797). 17 chapters, complete framework, Excel + Notion companions. Read once, apply for 12-24 months.

The Sale-Ready Toolkit ($497). 14 practical templates including EBITDA Add-Back Tracker, Customer Concentration Analyzer, Buyer KPI Dashboard, CIM Quality Narrative Template, and 30-Day Owner-Dependency Sprint plan.

Separately: $1,294. Bundle: $997. Save $297 and get the templates alongside the framework that explains why they matter.

Playbook Only · $797 Get the Bundle · $997

Ready to prepare your exit properly?

Every month you delay exit prep has a specific dollar cost. Six months of delay on a $3M IT services business can leave $100K to $300K on the table at close. Start with the framework.

$797 · Lifetime access · Excel + Notion included

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