DTC Podcast: Agency Confidential

Episode: Tom Shipley on Buying Growth: Scaling Your Agency Through Acquisitions
Date: January 31, 2026
Host: Jeff Shannon (Pilothouse Digital, Agency)
Guest: Tom Shipley (Investor, M&A Expert, Co-founder Atlantic Coast Brands, Foundry)

Episode Overview

This debut episode of Agency Confidential dives deep into the practicalities, philosophies, and strategies behind agency growth through acquisitions. Host Jeff Shannon speaks with Tom Shipley, a veteran of M&A in the direct-to-consumer and agency world, about how acquisitions can solve core business problems, the mindset and structures required, and practical tactics for minimizing risk and maximizing growth. The episode is packed with candid stories, actionable frameworks, and advice for agency leaders considering acquisitive growth.

Key Discussion Points & Insights

1. The Core Belief: “Any Business Problem Can Be Solved With Acquisition”

• Tom’s Origin Story with Acquisitions:

  • Faced with impending bankruptcy and a lack of resources, Tom was approached by a banker with an opportunity to buy a “cast-off” business from a larger deal—despite having no money.
  • Acquiring the $15M business more than doubled his company’s size, enabling an exit a year later.
  • Quote:

    “If you have a motivated seller, you can come to terms that you can work with.” — Tom Shipley [03:20]

• Solving Capability Gaps & Growth Roadblocks

  • Tom’s personal business reached operational limits—no team, no robust tech, no money. By acquiring a complementary business, they plugged in their brand and scaled from $331K to $100M in three years.
  • Story:
    • Example of an Amazon agency owner (Brian) who acquired another agency with operational excellence, addressing his skill/capacity gap and receiving a $187M offer subsequently.

2. Getting into the “Acquisition Mindset”

• Overcoming Inertia & Intimidation

  • Many agencies hesitate to acquire due to fear of risk, lack of knowledge, or feeling overwhelmed by the process.
  • Tom stresses it’s not about knowing every detail (“the how”) but focusing on “the who” – surrounding yourself with deal-makers and advisors who close knowledge gaps for you.
  • Quote:

    “It is never knowing all the how; it’s knowing the who.” — Tom Shipley [09:05]

• Math of Growth: Organic VS. Acquisitive

  • Growing 10% per year for 5 years = 50% increase in enterprise value.
  • Acquiring one business per year (half your size) = 1,200% increase in enterprise value (compounded).
  • Quote:

    “Dedicate 5% of your resources to acquisition… at the end of five years, you’ll increase your enterprise value by 1200%.” — Tom Shipley [10:33]

3. The Practicality of Financing and Deal Structuring

• Minimizing Risk to Your Core Business

  • Many agency deals use seller financing, earnouts, and low cash at close (as little as 5–10%), with the rest paid via seller notes tied to business performance.
  • Tom gives examples of deals closed at 5–10% cash down, with most of the purchase funded by the cashflow and assets of the acquired business, not the acquirer’s core cash.
  • Quote:

    “We negotiated… one [agency] deal we closed with 5% cash at close, the other 10% cash at close… 90% of the deal on seller notes.” — Tom Shipley [12:21]

• Why Motivated Sellers Matter

  • There’s a large and growing market of agency owners motivated by retirement or burnout—sometimes just wanting their people and legacy taken care of, not necessarily top dollar.

4. Building a Deal Flow Pipeline (“Acquisition Machine”)

• Volume of Conversations Trumps Secret Sauce

  • Success comes from systematically engaging in 100+ seller conversations; motivation and fit emerge from quality and quantity.
  • Use LinkedIn, cold outreach, and even strategic posts to drive deal flow.

• Crafting Your “Buy Box”

  • Define strict criteria (like client ICP) for the kinds of agencies you’re seeking—skills, revenue, geographic, or client focus.

• How to Approach Sellers

  • Be transparent; present yourself as open to acquisition or collaboration—not always a full buyout.
  • Build trust and learn about seller’s motivations, personal and professional aspirations.

• Quote:

  “My goal is just to get on a phone call. Five conversations a week over a year—250 seller conversations… If you have 100 conversations, you will end up closing the ideal acquisition.” — Tom Shipley [17:24]

5. Due Diligence & Integration: De-risking Deals

• Layered Due Diligence

  • First call is “get to know you”; if good fit, request basic info for a deeper business deep dive; no LOI or major info until both feel potential.
  • After LOI, do full due diligence: validate what’s been told, identify red/yellow/green flags, plan for “Day One” post-close.

• Integration: The “Do No Harm” Principle

  • Culture/people first: town halls, small group meetings for Q&A, focus on employees and clients on Day One.
  • Legal/structural integration can be staged; sometimes operate two agencies in parallel to reduce risks.
  • Quote:

    “The only thing I want to do is making sure on day one that I’m taking care of the clients, cash, and employees.” — Tom Shipley [27:45]

6. Contrasting Deal Structures for Alignment and Risk Mitigation

• Earnouts and Seller Notes

  • If performance drops, either payout amount decreases or the payout period extends—aligns incentives and protects both buyer and seller.

• Mitigating Client Concentration Risks

  • Structure deal so payout is linked to client retention and revenue performance.

• Key Question for Tough Situations

  • Quote:

    “What would have to be true to make this deal possible?” — Tom Shipley [31:15]

7. The State of the Industry & Why Now Is a Unique Acquisition Opportunity

• AI & Market Change
  • Agencies must be AI-forward or acquire AI-driven skills/culture. AI-resistant agencies face existential risk.
  • 2026: high anxiety and burnout among agency owners means more motivated, realistic sellers, and flexible deal terms.
  • Quote:

    “2026 in my opinion is the year for acquisitions. There are so many owners… scared to death their business is not going to be relevant. They’re afraid, and they’re going to put their business on the market.” — Tom Shipley [32:25]

Notable Quotes & Memorable Moments

• On why acquisition is the ultimate growth lever:

  “Whatever challenge you have… for example, you have an Amazon agency… the hottest thing is TikTok Shops. You can either build it on your own, or you can buy a TikTok Shop agency.” — Tom Shipley [07:12]

• On the importance of trust during dealmaking:

  “Remember, you have two sets of advisors telling you not to trust the other side. Everything’s about trust. If something’s bothering you at 10 pm, text me; let’s talk it through.” — Tom Shipley [27:00]

• On how to approach seller conversations:

  “It’s not about collecting competitive info. It’s about genuine interest in investment or collaboration. You’ll learn so much that will make your own agency stronger.” — Tom Shipley [19:04]

• On avoiding integration disaster:

  “If you rush and ignore people and clients, you will have wheelchair outages.” — Tom Shipley [29:22]

• On using deal terms creatively:

  “Nothing says don’t do a deal, the question is: what would have to be true to make this possible?” — Tom Shipley [31:15]

Timestamps for Key Segments

• Origin Stories and Philosophy of Acquisitions: 03:20–08:37
• Mental Models & Agency Growth Math: 09:05–11:31
• Deal Structure & Minimizing Risk: 11:54–15:23
• Seller Outreach, Buy Box, and Deal Flow: 16:47–20:12
• Due Diligence Process: 22:21–26:08
• Integration & Culture Post-Acquisition: 26:19–29:43
• Mitigating Risk with Deal Terms: 29:57–31:26
• AI & 2026 as the Year of Acquisitions: 32:02–34:55
• DealCon Event Details: 34:55–37:05

The Event: DealCon

• DealCon is Tom Shipley's flagship event diving deep into acquisition strategies for agencies.
• Three days: M&A tactics, networking, capital introductions, AI implementation in agencies—and a third day focused on exits and AI.
• Quote:

  “I want people to say the quality of the content and the character of the people in the room is the highest of any event they’ve ever been to.” — Tom Shipley [36:22]

Useful For…

• Agency owners and leaders interested in M&A as a growth strategy
• Anyone looking to understand the mindset and mechanics behind lower-risk deals
• Operators seeking practical frameworks for sourcing, structuring, and integrating agency acquisitions

Tone & Feel

Candid, energetic, direct, and strategy-focused—with a spirit of abundance and community. Both host and guest are practical, anecdotal, and keen to demystify M&A for founders and operators in the agency world.