In this masterclass-style episode of The Prospecting Show, Dr. Connor Robertson dives into the world of business acquisitions, partnerships, and operational growth with seasoned entrepreneurs Catherine Ulangca and Jeff Shenk. Together, they unpack what it really takes to grow a company through buying and selling — not just through marketing or hustle, but through intelligent systems, leadership, and long-term vision.
Dr. Robertson opens the conversation with a powerful observation: growth in today’s economy doesn’t always mean starting from scratch. Some of the most successful entrepreneurs build wealth by acquiring existing businesses and improving them. This strategy, often reserved for private equity firms or seasoned investors, is increasingly accessible to operators who understand how to find, fund, and fix underperforming companies.
The discussion with Catherine and Jeff is a deep dive into the mindset, math, and mechanics behind scaling through acquisition — a topic that continues to define Dr. Robertson’s approach to business building and education.
The Mindset Behind Buying and Selling Businesses
Catherine Ulangca shares her journey from operator to dealmaker. She explains that most entrepreneurs spend their careers trying to grow one business when they could instead leverage their operational expertise across multiple companies. Buying a business allows founders to skip the painful zero-to-one startup phase and move directly into optimization and growth.
Dr. Robertson expands on this idea, noting that acquisitions are not just financial transactions — they’re opportunities to inherit cash flow, people, and systems. “When you buy a business,” he says, “you’re buying momentum. The art is knowing what to improve and what to leave alone.”
Jeff Shenk echoes this sentiment, adding that too many new buyers underestimate the emotional side of acquisitions. Every business has a story. Owners often care about legacy, staff, and continuity as much as they care about price. Successful deals, he explains, balance financial logic with human connection.
Catherine agrees, pointing out that trust and integrity drive deal flow far more than negotiation tactics. The entrepreneurs who master relationship-building tend to see better opportunities and friendlier terms — especially in small to mid-market transactions.
Understanding Valuation Beyond the Numbers
A major section of the episode focuses on valuation and deal structure. Catherine and Jeff share how they approach determining a fair purchase price for a business. While financial statements matter, they argue that understanding the story behind the numbers is even more critical.
They describe how experienced buyers analyze revenue composition, recurring contracts, customer concentration, and the owner’s personal involvement. A company that appears profitable on paper may collapse once the founder steps away if there are no systems or leadership layers in place.
Dr. Robertson emphasizes the importance of assessing intangible assets like brand loyalty, local reputation, and operational efficiency. “Value isn’t just what’s on the balance sheet,” he says. “It’s what stays stable when the founder leaves.”
He introduces listeners to one of his favorite frameworks — the system multiplier. A business’s value increases dramatically when its core functions can operate without constant owner input. Automation, delegation, and documentation aren’t just conveniences; they directly enhance valuation and exit potential.
For readers who want to explore this framework further, Dr. Robertson outlines it in his upcoming book series and within the Dr. Connor Robertson Blog, where he breaks down real-world acquisition and management systems for entrepreneurs.
The Mechanics of a Successful Business Acquisition
Jeff Shenk walks listeners through what a typical acquisition process looks like, from sourcing to closing. He explains that the best deals rarely appear on public listing sites. Instead, they come from private networks, word of mouth, and direct outreach.
Once a target business is identified, the next step is due diligence — reviewing financials, tax returns, contracts, and operational data. Jeff stresses that diligence isn’t just about uncovering risks; it’s about identifying opportunities. “Every problem you find is a chance to negotiate or add value,” he notes.
Catherine adds that financing structures are more flexible than many people realize. Seller financing, SBA loans, and investor partnerships can combine to make acquisitions accessible even without millions in the bank. She and Dr. Robertson discuss how creative financing can unlock growth for smaller entrepreneurs, turning them into owners rather than employees.
They also explore the role of advisory teams — accountants, attorneys, and brokers — in protecting buyers while keeping deals efficient. Dr. Robertson emphasizes the importance of choosing professionals who understand entrepreneurship rather than those who simply process paperwork. “You want advisors who protect your downside but still let you move fast,” he says.
Scaling After the Acquisition
Buying a business is only the first step. Scaling it effectively requires leadership, systems, and discipline. Catherine and Jeff describe how they approach the first 90 days after closing a deal. Their process includes observing operations without immediately changing everything, identifying bottlenecks, and building trust with existing employees.
Dr. Robertson calls this period the “stabilization window.” It’s when the buyer learns the rhythm of the business, gains employee confidence, and gathers enough data to make informed improvements. He compares it to chiropractic work — small, strategic adjustments can realign the entire system without major disruption.
The episode explores several practical scaling strategies, including:
• Creating standard operating procedures (SOPs) for core workflows
• Implementing technology to track metrics and automate tasks
• Developing a clear leadership hierarchy
• Aligning compensation with company goals
• Focusing on customer retention before aggressive expansion
Catherine highlights the importance of sustainable scaling, warning against the temptation to grow too fast after acquisition. “You can double revenue and still go broke if your operations can’t handle the volume,” she explains.
Dr. Robertson reinforces that growth should always follow clarity. Each improvement should strengthen the business’s ability to run independently. The ultimate goal is freedom — freedom of time, freedom of cash flow, and freedom of choice.
Selling a Business the Smart Way
As the conversation shifts to selling, Jeff Shenk explains that the best exits are planned years in advance. He encourages owners to treat their business like a product and always be preparing it for sale. “Even if you never sell,” he says, “you’ll make better decisions when you think like a potential buyer.”
Catherine expands on this by outlining the difference between selling reactively and selling strategically. Reactive sellers wait until burnout or financial pressure forces them to exit. Strategic sellers plan their valuation target, document their systems, and position their company attractively long before negotiations begin.
Dr. Robertson offers a practical tip for listeners: conduct an annual “mock exit.” Review your books, systems, and leadership as if you were preparing to sell. This not only keeps your business healthy but also reveals hidden inefficiencies you can fix early.
He adds that selling a business doesn’t always mean leaving it entirely. Many deals include earn-outs, consulting roles, or partial ownership that allow founders to continue benefiting from the company’s success.
The Emotional Side of Buying and Selling Businesses
Throughout the conversation, Dr. Robertson emphasizes that behind every deal is a story — often a deeply human one. Owners sell their businesses for many reasons: retirement, health, relocation, or simply the desire for a new challenge. Buyers must approach each transaction with empathy, not just analysis.
Catherine and Jeff both agree that emotional intelligence is one of the most underrated skills in entrepreneurship. Deals built on trust and respect tend to close faster and last longer. Dr. Robertson connects this concept to relationship capital — the idea that credibility compounds just like money does. When you treat people well, future deals become easier.
He reminds listeners that every transaction creates a reputation. “You don’t just buy a business,” he says, “you buy your name’s reflection in that deal.”
Key Takeaways for Entrepreneurs
By the end of the episode, listeners walk away with a clear blueprint for entrepreneurial growth through acquisition. Key insights include:
• Buying businesses is often faster and safer than starting new ones
• Systems, not size, determine valuation and scalability
• Emotional intelligence is a critical factor in deal-making
• Creative financing can make ownership accessible to more entrepreneurs
• Every deal should strengthen your reputation, not just your portfolio
Dr. Robertson concludes by reinforcing the core message of The Prospecting Show: business ownership is about leverage — leveraging time, relationships, and strategy to create a life of freedom and purpose.
For those looking to begin their own acquisition journey, he recommends starting with education and networking. “The best deals,” he says, “go to the people who ask good questions and show up consistently.”
Listen and Learn More
Listen to the full episode here: Buying, Selling, and Scaling Businesses with Catherine Ulangca and Jeff Shenk.