Exit planning

In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome business intermediary Tom Gottlieb of Berkshire Hathaway. Tom brings decades of experience in buying, selling, and valuing businesses across the Midwest. The conversation dives deep into what truly drives the value of a company—and how sales leaders and business owners alike can prepare their organizations for a future transition. Whether you’re a business owner considering a sale or a sales executive interested in how sales performance impacts company valuation, this episode delivers invaluable guidance. It’s part education, part strategy session, and all high-value insight.

Key Topics Discussed

The Three Core Approaches to Business Valuation – Asset, income, and comparative market methods explained simply and practically. (04:22)
Preparing a Business for Sale: Lessons from Real Estate – Why “curb appeal” matters for companies and how to improve it over time. (07:36)
What Buyers Want: Sales Growth, Consistency, and Processes – How prospective buyers assess the health of a business beyond profit margins. (09:00)
The Hidden Red Flag: When the Owner Is the Only Salesperson – Risks for buyers and strategies for mitigating dependency on the founder. (13:31)
Leveraging AI to Gain Competitive Market Intelligence – How technology is transforming buyer and seller knowledge in M&A. (11:32)

Key Quotes

Tom Gottlieb: “Every buyer wants the same thing: a business that works without the owner. That means strong processes, steady sales growth, and predictable profitability.” (09:01)
Sean O’Shaughnessey: “So if you don’t want to stick around after the sale, then train your sales team now—and watch the value of your company go up.” (14:16)
Kevin Lawson: “Tom, every time we talk, I walk away with something new. This episode is no exception.” (11:31)
Tom Gottlieb: “Buyers rarely show up with a bag of cash. There’s a timeline. A deal doesn’t close in a weekend—it’s often a year-long journey.” (07:00)

Additional Resources

Connect with Tom Gottlieb on LinkedIn
Tom’s Email: tgottlieb@bhhspro.com
Direct Contact: (562) 225-4567
Berkshire Hathaway HomeServices Professional Realty – Business Brokerage Services

A Significant Actionable Item from this Podcast

Start documenting your sales process today.
If you are a business owner—or advise one—and the majority of revenue hinges on a single salesperson (often the owner themselves), that’s a red flag for any future buyer. Begin formalizing your sales process, distribute responsibilities among team members, and track sales metrics consistently. This improves operational resilience and significantly enhances company value in a potential sale.

Why You Should Listen to This Episode

Selling a business isn’t just about profit, perception, process, and preparedness. In this episode, Kevin and Sean extract wisdom from Tom Gottlieb that applies to any B2B organization considering an exit in the next 3 to 10 years. It’s packed with strategic takeaways, sales insights, and behind-the-scenes truths about what makes a business attractive to buyers. Whether you’re a founder, an investor, or a sales leader, this episode will reshape how you think about long-term value creation. Tune in and learn how to make your business sell-ready—starting now.

To understand if your company is doing a great job in sales, take this quick and easy assessment: https://newsales.expert/b2b-sales-capability-assessment/

A common question that I receive is about the value of adding fractional sales leadership to their company. I typically answer their concern with a story about one of my clients who had a fantastic experience and increased the company’s value by 167% in about 12 months.

The true benefit of the efforts of fractional sales leadership is that revenue and pipeline will increase your company’s value.

Several years ago, I was hired by a fantastic software startup company in the artificial intelligence industry. Their technology had roots in original research by one of the founders at MIT. I was connected to one of the founders, and he approached me to be his Fractional Vice President of Sales as they felt that their technology had progressed to the point that they needed to find early adopter customers.

It was a young company with a small client base and very little revenue, but it clearly understood its offering and the value it could deliver to new clients. I started the engagement with my standard discovery process to identify what value they were providing to their clients or prospective clients. We developed a target persona, and I helped them identify potential clients that fit their use cases.

As I worked with them, I learned more about their backstory. A significant chip manufacturer had wanted to buy the company just a few months earlier. The founders were eager to sell, but the parties couldn’t agree on a price and parted ways. The large chip manufacturer valued the company at about 75% of the valuation that the founders wanted. This offer reminded me of the popular TV show Shark Tank, where entrepreneurs try to arrange investments from 5 individual investors. They rarely agree at the beginning of the segment on the startup’s value; sometimes, they compromise, and sometimes they do not. In this case, the giant chip manufacturer didn’t see the value, just like the Sharks didn’t see the value of Ring.

The owners of my client did what any sound company executives would do. They pushed harder on their business to build its value. They realized that nothing drives the company’s value like revenue and pipeline, so they brought me in to help them.

Fast forward ten months after hiring me, and our pipeline, messaging, sales team, partnerships, and methodologies have improved dramatically. At this point, another chip manufacturer enters the picture and wants to acquire the company and its technology. But now everything in the company is more proven, and the risk is less for the acquiring company. The owners and the new acquiring company agreed quickly on the company’s value. The company was now worth 200% of what the founders initially thought just the previous year. The deal closed quickly and efficiently, with most employees finding great jobs at the new owner while some continued with new and exciting adventures.

New customers, pipeline growth, and team growth caused a dramatic increase in the company’s value. Undoubtedly, the software improved during that year, but much of that improvement was because of customer and prospect feedback. The new chip manufacturer thought the company was worth 267% compared to the previous suitor.

According to the Exit Planning Institute, 76 percent of business owners who sold their businesses profoundly regretted selling within a year. I contend that this is because they agreed to a Shark Tank deal which devalued their company. I think most feel they didn’t get the value out of the company they spent years, decades, or maybe a lifetime building. The solution is to have such a great sales engine that the buyer is begging you to take the offer. Small business owners need to build a sales engine that is so strong that multiple offers are coming in to buy the company. For a while in the US after COVID-19, selling a home commanded over-asking-price offers all over the nation. This seller’s market is the environment you need to create for your company if you want to exit the company in the next 3-5 years.

I help company owners realize the maximum value of their company by improving their revenue generation capability. I help owners enhance their sales management, methodologies, processes, teams, and messaging to accomplish this. Reach out to me so that I can help you maximize your company’s value the way I helped my former client.