How are successful buyers finding businesses that never hit the market?

In this episode of Acquisitions Academy, host Mike Abramowitz sits down with Ayelet Shipley, M&A strategist and co-founder of Liquidity Studio, to unpack how off-market deals are actually sourced, structured, and closed in the lower middle market.

Ayelet explains how the M&A landscape has shifted from traditional auction processes toward more relationship-driven, bilateral deal making. Instead of waiting for businesses to appear on marketplaces, buyers can proactively identify companies that fit their buy box, build targeted lists, and reach out directly to potential sellers through LinkedIn, data platforms, industry communities, and trusted relationships.

The result? Buyers can discover business owners who may not have been actively planning to sell but could be open to the right conversation.

Ayelet walks Mike through her programmatic M&A outreach strategy, including how she builds targeted prospect lists, uses data tools such as SourceScrub and Clay, creates personalized LinkedIn messaging, and moves qualified prospects into short 15–30 minute alignment calls. She also explains why LinkedIn can outperform cold email in an environment where inboxes are increasingly saturated with unsolicited outreach.

But sourcing is only part of the equation. Ayelet emphasizes that trust and founder psychology can determine whether an off-market opportunity turns into a real transaction. Business owners often view their companies as deeply personal creations, so buyers need to build rapport, manage expectations, and understand the seller's motivations before jumping into negotiations.

The conversation also explores one of the most important M&A lessons: structure can matter more than headline enterprise value. Ayelet explains how buyers and sellers should think about risk allocation, incentives, walkaway points, and deal terms rather than focusing exclusively on the purchase price.

You'll discover:
• How M&A is shifting from auctions toward bilateral transactions
• Why many off-market sellers weren't originally planning to sell
• How to build a targeted acquisition pipeline

Featured Guest: Ayelet Shipley

Ayelet Shipley is an M&A strategist and co-founder of Liquidity Studio, helping buyers and sellers navigate lower-middle-market transactions through targeted sourcing, relationship-driven outreach, and thoughtful deal structuring.

Quotes from Ayelet:

“What’s happened in the most recent 24 months is the shift from the auction processes to a lot more majority bilateral deal-making.”

“The seller is actually not necessarily on the market.”

“I have been running programmatic M&A direct cold outreach strategies for the last five years.”

“It’s all about risk allocation… Structure over enterprise value every day, every day, every day.”

Episode Timeline:

00:00 Welcome & Introduction to Ayelet Shipley
02:40 The Shift From Auctions to Bilateral M&A
04:30 Programmatic Outreach for Off-Market Deals
06:30 LinkedIn, Data Tools & Deal Flow
14:45 Building Trust & Courting Potential Sellers
18:10 Buy Boxes, Screening & Deal Fit
20:40 When a Business Isn't Ready to Sell
23:40 Buy-Side vs. Sell-Side Psychology
28:56 Why Structure Beats Enterprise Value
30:45 The Barbecue Test & Successful Exits
32:10 Finding Ayelet & Liquidity Studio
34:13 Advice for the Next Generation of Dealmakers

Connect with Ayelet Shipley:

🌐 Liquidity Studio: liquiditystudio.com
📧 Email: ayelet.shipley@liquiditystudio.com
💼 LinkedIn: linkedin.com/in/ayelet-shipley-b16330149/
📱 Instagram: instagram.com/ayelet_shipley/

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