The most valuable commercial deals rarely appear on listing platforms. By the time the market sees them, the upside is already priced in. The real opportunities — the ones that generate steady yield and long-term upside — are found weeks or months earlier, while a property is still moving quietly through private conversations and relationship-driven channels. That’s where disciplined investors thrive.
In today’s Commercial Real Estate Finance landscape, the mid-market segment has become especially attractive. Assets too small for institutional giants and too large for individual operators create a perfect window for investors who know how to move quickly, negotiate privately, and understand the seller’s motivations before anyone else is even aware of the deal. The ability to secure these opportunities consistently is a skill — and it’s one I’ve spent years refining through development work, REIT Investment Strategy, and years navigating the Experience Economy expansion.
This article breaks down three practical elements of mastering off-market or pre-market deal flow:
- How to identify sellers before they raise their hand?
- How to structure negotiations that align interests long before a deal turns competitive
- How to build relationships that make you the first — or only — call
These insights reflect the approach Randall Starr believes will define the next wave of mid-market acquisition success.
1. The Best Deals Come from Understanding Motivation, Not Price
Negotiation begins long before numbers are discussed
Mid-market commercial deals don’t materialize by accident. They come from understanding the pressures facing an owner – financial, strategic, operational, or personal. The investors who win these deals are the ones who invest time into knowing what the seller truly needs.
Every owner falls into one of a few categories:
- The operator who’s ready to exit but doesn’t want public attention
This owner values speed, certainty, and discretion. They want a straightforward process. - The investor who senses the market peaking and wants to lock in gains quietly
They don’t want to test the market. They want a clean, predictable buyer. - The group facing refinancing pressure
Higher rates are creating quiet distress. Not bankruptcy-level distress — timing distress. - The parent company streamlining non-core assets
These deals move quickly because they’re strategic, not sentimental.
The most effective negotiators identify these motivations before the owner ever talks about selling.
A lesson from experiential expansion
During a multi-unit rollout I worked on, one of the strongest sites came from identifying an owner facing a quiet operational challenge. Their revenue was steady, but a key partnership behind the scenes was unraveling. The property wasn’t distressed — the ownership structure was. Recognizing that early allowed us to negotiate in a window when the owner wanted certainty more than price maximization.
That experience shaped the way Randall Starr approaches off-market conversations:
Find the pressure point early, and the negotiation becomes a solution, not a battle.
2. Mid-Market Acquisitions Are Won by Being the Buyer with the Clearest Path
Certainty, clarity, and speed outperform the highest price
Mid-market owners care deeply about who they are selling to. A competitive bidding environment can be draining and expensive for them. Many prefer a clean path with a buyer who understands:
- Local entitlements
- Asset condition
- Financing timelines
- The operational reality of the property
- The personality of the submarket
In several deals I’ve observed, an offer that wasn’t the highest still won because the buyer demonstrated they could close faster and with fewer variables.
What strong buyers provide in early conversations?
- A clear capital stack
No ambiguity. No “subject to investors.” Certainty builds confidence. - A clean due diligence process
Sellers respond to buyers who outline exactly what they will review and how quickly. - A willingness to take on minor issues without renegotiation
This signals respect for the seller’s timeline. - The experience to evaluate the real risk quickly
Overly cautious buyers often kill their own momentum.
A buyer who communicates clearly often gets exclusivity before a property ever hits the market — simply because they make the process easier on the seller.
3. Relationships Create Deal Flow – Expertise Closes the Deal
Being the first call requires long-term trust
Many off-market opportunities are born from years of consistent, low-pressure relationship building:
- Property managers
- Attorneys
- Lenders
- Appraisers
- Tenant reps
- Local political contacts
- Developers who lack capital but have visibility
These people sit closer to transactions than listing brokers. They see the early signals: a property struggling with tenant turnover, an owner in conflict with partners, a building facing upcoming renewal risk.
The investors who gain early access are the ones who treat relationships as part of the job, not an afterthought.
Expertise matters once the door opens
Early awareness is useless if you can’t evaluate quickly. This is where understanding tenant behavior, operating statements, submarket trends, and real-time capital markets comes into play.
During a period of heavy site evaluation for experiential development, my team often toured buildings that looked promising on paper but failed the in-person test. One deal, in particular, taught us the importance of walking on a property at different times of day. The daytime foot traffic was excellent, but the evening environment was unusually quiet for the trade area. That small behavioral insight prevented us from pursuing a deal that would’ve underperformed.
This same instinct is essential when navigating off-market mid-market acquisitions. Expertise doesn’t just validate opportunities – it eliminates bad ones quickly.
4. Negotiating Before the Market Sees the Deal Requires Precision
The structure of the offer matters as much as the price
In pre-market negotiations, the goal is not to “win the deal.” The goal is to convince the seller that the transaction will be smooth, predictable, and aligned with their objectives.
Buyers who excel in this space use:
- Pre-agreed timelines
Clear milestones for due diligence, financing, and closing. - Earnest money structures that signal confidence
Sometimes a small hard-deposit early earns trust faster than price increases. - Creative structuressuch as:
- Partial leasebacks
- Deferred closings
- Short-term management agreements
- Carve-outs that let the seller retain a small interest
- Respect for confidentiality
Sellers want discretion. The more a buyer respects that, the faster the deal progresses.
The mid-market is the perfect environment for these structures — big enough for sophisticated strategies to matter, but small enough that relationships and reputation still carry weight.
A negotiation insight from real experience
In one negotiation early in my career, a seller wasn’t ready to let go, but they needed relief from operational pressure. They didn’t want a full sale. They didn’t want a long process. They wanted breathing room.
The solution was a short-term management transition paired with a structured closing timeline. It wasn’t a standard deal, but it solved the seller’s problem and secured a high-performing asset without any public bidding.
That deal reinforced a principle I still follow today:
If you understand what the seller truly needs, you can create a structure no one else even thinks to propose.
Conclusion
In a market where information moves fast but true opportunities move quietly, the ability to secure mid-market commercial acquisitions before they go public is one of the strongest competitive advantages an investor can have. It requires discipline, timing, relationship depth, and a negotiation strategy built around clarity and alignment.
The investors who master this art aren’t chasing deals — they’re creating them. They’re reading signals early, moving decisively, and earning trust long before an LOI is drafted.
This is the heart of successful off-market acquisition strategy, and it’s a discipline Randall Starr believes will define the next cycle of mid-market investment leadership.
