Wolfspire Solutions
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The CIO's Exit Playbook

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

17 chapters. Roughly 50,000 words. Written from the specific vantage point of an active buyer. Everything an IT founder needs to prepare for exit in the next 12 to 24 months.

$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, roughly 50,000 words, four-part 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 with real category examples
  • Companion Notion workspace: full exit-prep operating system you can drop into your existing setup
  • Lifetime access, delivered instantly via Gumroad
  • All future updates included

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

Get the Playbook →

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