When I look back on the best acquisitions I’ve made, one theme shows up again and again: the deal didn’t come from a public listing. It came from a relationship. Brokers and online platforms have their place, but the most attractive opportunities, the ones with strong businesses, fair terms, and willing sellers, are often never advertised. They’re discovered through networks, introductions, and conversations.
In this article, I want to share how I’ve used relationships to uncover off-market businesses for sale, why these opportunities are so valuable, and the lessons I’ve learned about building trust with owners long before they decide to sell.
Why Off-Market Deals Matter
There’s a big difference between a business that’s listed for sale and a business that’s quietly available. Listed businesses attract multiple buyers, which drives up price and competition. Off-market businesses, by contrast, are opportunities where the seller hasn’t formally put the company on the market but is open to conversations.
These deals are valuable because:
- There’s less competition.
- Negotiations are more collaborative than adversarial.
- The seller often prioritizes legacy and cultural fit over maximizing price.
- I can build a relationship before numbers dominate the conversation.
In my experience, the best deals often come from situations where the owner wasn’t planning to sell right away but was open to exploring the idea with someone they trusted.
Building Relationships Before There’s a Deal
One of the biggest mistakes I see buyers make is approaching owners only when they want to buy. By then, it’s often too late. The seller may feel ambushed or suspicious of sudden interest.
Instead, I focus on building relationships long before a deal is on the table. I attend industry events, join local business groups, and stay connected with professionals in sectors I’m interested in. I don’t push for sales conversations. I simply get to know people, listen to their challenges, and share my perspective when asked.
This slow approach pays off. When an owner eventually considers selling, I’m not a stranger—I’m someone they know, trust, and feel comfortable talking to.
The Role of Referrals
Another powerful source of off-market opportunities has been referrals. Accountants, attorneys, bankers, and consultants often know when a business owner is thinking about retirement or exploring options. By building strong relationships with these professionals, I’ve been introduced to owners before the business ever hits the market.
I don’t approach these referral partners with a transactional mindset. I make sure they know who I am, what types of businesses I look for, and why I care about legacy and employees. When they believe I’ll be a good steward, they’re much more willing to connect me with their clients.
Asking the Right Questions
When I meet business owners, I don’t immediately ask if they’re interested in selling. Instead, I ask questions about their goals, their challenges, and what they want for the future. Many owners are thinking about succession but haven’t formalized a plan. By showing genuine curiosity, I open the door for conversations that might later lead to an acquisition.
Questions like:
- “What do you see as the next chapter for your business?”
- “How are you thinking about succession over the next five to ten years?”
- “What would an ideal transition look like for you someday?”
These questions aren’t pushy. They show that I’m thinking long term, which helps owners see me as a potential partner rather than just a buyer.
Why Trust Is the Currency of Off-Market Deals
Every off-market deal I’ve done has been built on trust. Owners don’t want to expose sensitive financials or admit they’re thinking about selling unless they believe the conversation will be confidential and respectful.
I earn that trust by being transparent about who I am and what I’m looking for. I don’t oversell myself. I don’t promise things I can’t deliver. Instead, I make it clear that I’m looking for businesses where I can preserve culture, grow operations, and take care of employees. That message resonates deeply with owners who care about their legacy.
Leveraging My Existing Network
One of the most overlooked strategies for finding off-market businesses has been tapping into my own network. Friends, colleagues, and former business contacts often know owners who are considering a sale. By simply sharing what I do and the types of businesses I’m interested in, I’ve created opportunities I would have never found otherwise.
I’ve learned that you don’t need thousands of connections. You just need to be clear about your intentions and consistent in communicating them. People remember, and when they hear of opportunities, they think of you.
Relationship-Based Negotiations
Another advantage of off-market deals is the way negotiations unfold. In listed deals, the process feels adversarial. Both sides are trying to “win.” In off-market conversations, the foundation is the relationship. Sellers are more open, more flexible, and more willing to consider creative structures when they believe in the buyer.
I’ve been able to negotiate seller financing, extended transitions, and favorable terms in part because the relationship came first. The numbers mattered, but trust was the deciding factor.
Lessons I’ve Learned from Off-Market Deals
Looking back, several lessons stand out:
- Patience pays off. Off-market deals rarely happen overnight. They develop over months or even years.
- Respect confidentiality. If an owner senses you’ll share their intentions publicly, the relationship ends immediately.
- Legacy often outweighs price. Many sellers care deeply about who takes over, not just how much they receive.
- Small conversations matter. A casual lunch or phone call can set the stage for a future deal.
- Always add value. Even if an owner isn’t ready to sell, I try to leave them with an idea, resource, or perspective that benefits them now.
The Power of Long-Term Thinking
Ultimately, finding off-market businesses requires a long-term mindset. I don’t chase instant results. I build relationships consistently, knowing that some may not bear fruit for years. But when they do, the deals are often stronger, smoother, and more rewarding than anything found through a broker listing.
Final Thoughts
The best acquisitions I’ve made didn’t come from flashy listings or competitive bidding wars. They came from quiet conversations, trusted introductions, and relationships built over time. By focusing on people, not just transactions, I’ve been able to uncover opportunities that others never even knew existed.
If you want to find off-market businesses, start by building relationships. Be patient, be genuine, and be consistent. The opportunities are out there, but they reveal themselves only to buyers who are willing to invest in trust long before the deal.
I continue sharing strategies, stories, and lessons from my acquisitions and real estate ventures on DrConnorRobertson.com, where I document what I’ve learned in the world of business buying.