Shoot the Moon with Revenue Rocket

Revenue Rocket Consulting Group

The Shoot the Moon podcast is for IT business owners and executives. The Revenue Rocket leadership team brings their 25+ years of experience with M&A and growth strategies to IT Services company leaders worldwide.

  1. FEB 24

    The Sell Side Masterclass for Tech Services Founders: Due Diligence

    EPISODE 245.  Key Takeaways: What due diligence is: The buyer’s inspection/audit of the seller’s business to confirm the story, financials, contracts, and assumptions made pre-LOI. The emotional shift for sellers: Post-LOI can feel like “we’re done,” but diligence is often the most challenging phase and can be exhausting and distracting. Why buyers do it: Risk mitigation and validation, plus identifying upside (synergies, growth investment opportunities, consolidation savings). Common seller mistake: Underestimating diligence and showing up unprepared, both emotionally and operationally. Role of an M&A advisor: First point of contact, ensuring data is clean/defensible, fast response cadence, and pushing back where appropriate. “Scope creep” reality: Multiple outside parties (QoE, tax, legal, integration) often ask overlapping questions, creating a “Groundhog Day” effect without strong process management. Top diligence areas buyers focus on: Revenue quality, customer concentration, contracts/renewals, security posture, key person risk, and scalable delivery model. Retrade risk signals: Business performance softening during diligence, messy financials, messy contracts, or major unexpected changes in the business. Keep momentum (they cite ~90 days as a good diligence window) and don’t let diligence distract leadership so much that performance slips. Listen to Shoot the Moon on Apple Podcasts or Spotify. Buy, sell, or grow your tech-enabled services firm with Revenue Rocket.

    26 min
  2. FEB 11

    The Sell Side Masterclass for Tech Services Founders: Deal Structure 101

    In this installment of the Sell Side Master Class, Ryan and Mike break down deal structure, the terms behind the headline enterprise value and why structure can matter as much as (or more than) price. They walk through the most common components of consideration in IT services M&A: cash at close, earnouts, seller notes, and rollover equity, including where each can create upside and where hidden risk lives. Mike explains why earnouts often get an unfair reputation, what “good” earnout design looks like, and why indexing to revenue is typically safer than profit. They also cover how seller notes work (and why they’re subordinated to bank debt), what rollover equity really means in a PE-backed deal, and the “often missed” lever of working capital, including how sellers can accidentally leave money on the table without the right guidance. Tune in as we talk Deal Structures 101. DEAL STRUCTURES WE DISCUSS: Cash at close: The portion of the purchase price you receive when the deal closes. In the episode, this is framed as the most straightforward form of consideration and the “baseline” sellers compare other components against. Earnout: A contingent payment you can earn after closing if the business hits agreed performance targets. Mike explains that earnouts often work best when they’re indexed higher on the P&L (commonly revenue, sometimes gross margin) and structured with a “lane” or prorated payout range instead of an all-or-nothing cliff. Example from the episode’s concept: if revenue lands within a defined band around the forecast, you receive a proportional earnout payout. Seller note: Seller financing where the seller effectively becomes a lender to the buyer for part of the purchase price. The transcript describes this as the seller “acting like the bank,” typically with interest, and notes that it is usually subordinated to senior bank debt. Example conceptually: you receive part of the price over time as principal plus interest rather than all at close. Rollover equity: The seller reinvests a portion of proceeds into the new ownership structure, keeping equity in the business post-transaction. In the episode, this is discussed as the “second bite of the apple,” often seen in PE-backed deals where the seller participates in future upside at a later liquidity event. Working capital adjustment: A structural mechanism that sets a working capital “target” at close and adjusts the seller’s proceeds up or down depending on whether the company delivers more or less working capital than agreed. The transcript emphasizes this as an often-overlooked lever and discusses that many owners are overcapitalized, meaning working capital can meaningfully impact what the seller takes home if negotiated correctly. Mixing structures to optimize EV and share risk: The episode repeatedly frames structure as a way to balance risk between buyer and seller and sometimes increase headline enterprise value. Example concept: a buyer may offer a higher total value if some portion is contingent (earnout) or deferred (seller note) versus paying the entire amount in cash at close.   OTHER EPISODES IN THIS SERIES: Part 1. Knowing When It’s Time to Sell: Listen now >> Part 2. Get Your House in Order: Listen now >> Part 3. Valuation Drivers: Listen now >> Part 4. What is my Take Home? Listen now >> Part 5. It Takes a Village. Listen now >> Part 6. The First 30 Days of a Process. Listen now >> Part 7. Finding the Right Buyer. Listen now >> Listen to Shoot the Moon on Apple Podcasts or Spotify. Buy, sell, or grow your tech-enabled services firm with Revenue Rocket.

    37 min
  3. JAN 22

    The Sell Side Masterclass for Tech Services Founders: The First 30 Days of a Process

    What does it really feel like when you decide to sell and the process officially begins? In this Sell-Side Master Class episode, we walk through month zero and the first 30 days of a sell-side process: the pre-market foundation, the time commitment, and the “transfer” that has to happen so an advisor can speak like they’re part of your team. We cover the core information you’ll be asked to assemble (financials, customer data, employee data, forecasting, go-to-market materials), plus the practical reality that founders often need to keep the circle tight to avoid data leakage internally. We also explain the role of the three key documents that drive early-stage buyer movement: Teaser (anonymous, broad interest) Confidential Information Memorandum (CIM) (post-NDA, full story) Financial packet / data room (deeper dive, typically after qualification) Finally, we talk through a critical leadership question that often evolves during the process: are you selling in or selling out? And we close with a simple reminder: preparation equals leverage because speed and clarity protect value.   Other Episodes in this Series Part 1. Knowing When It’s Time to Sell: Listen now >> Part 2. Get Your House in Order: Listen now >> Part 3. Valuation Drivers: Listen now >> Part 4. What is my Take Home? Listen now >> Part 5. It Takes a Village. Listen now >> Listen to Shoot the Moon on Apple Podcasts or Spotify. Buy, sell, or grow your tech-enabled services firm with Revenue Rocket.

    37 min
  4. 12/10/2025

    The Sell Side Masterclass for Tech Services Founders: Get Your House in Order

    In this Seller Master Class episode, the team digs into readiness: the unsexy work that makes or breaks your deal. Last time, they explored the decision to sell. This week is all about getting your house in order so buyers can move quickly and confidently through diligence. We cover why “time kills all deals” and how the vibrancy or cadence of a deal is driven by how fast you can deliver clean, accurate information. Financial readiness basics: Clean P&L with defensible add-backs and clear, normalized EBITDAMoving from cash to accrual accounting and resolving open issuesUnderstanding your revenue mix (recurring vs. one-time vs. resale, deferred revenue)Showing consistency over years, not just monthsPeople & leadership readiness: Reducing over-dependence on the founder across sales, operations, and deliveryDemonstrating a leadership team that can scale and executeSuccession planning — including “who’s in the tent” during a transactionUsing data (e.g., sales leadership forecasting growth from customer intimacy) to prove leadership impactOperational readiness: Tool stack hygiene, systems that actually work, and useful dashboardsPSA/ticketing discipline and clarity on what makes up your gross marginTransferable contracts with clean renewal and termination languageCustomer satisfaction metrics buyers will want to seeCustomer & contract hygiene: Clear target market and GTM strategy (vertical, size, geography, problem-based, etc.)Demonstrating long-term, renewing, high-intimacy customer relationshipsMaking sure contracts and your chart of accounts tell the same story buyers see in the dataLegal and compliance housekeeping: Corporate and regulatory filings (e.g., secretary of state docs, LLC details)Clean cap tableFixing misclassified contractors, missing signatures, and expired MSAs before diligenceIf you only have 90 days to get ready: Prioritize financial readiness and third-party-vetted numbersTighten up contracts and leadership accountability (“who’s who in the zoo”)Start building a data room with financial, contract, and operational data buyers will expect to seeTying it together with strategy: How “selling in” vs. “selling out” ties to your readiness story Showing that your differentiation, GTM, and organization are well thought out — and executable with or without the founder in the seat This episode is perfect for: Founders and leaders of IT services and MSP firms who see an exit on the horizon and want to avoid value-eroding surprises in diligence. Listen to Shoot the Moon on Apple Podcasts or Spotify. Buy, sell, or grow your tech-enabled services firm with Revenue Rocket.

    26 min

Ratings & Reviews

5
out of 5
6 Ratings

About

The Shoot the Moon podcast is for IT business owners and executives. The Revenue Rocket leadership team brings their 25+ years of experience with M&A and growth strategies to IT Services company leaders worldwide.