What’s One Unexpected Thing You Learned From Successfully Selling Your Business?

“What’s one unexpected thing you learned from successfully selling your business?”

Here’s what business leaders had to say:

1. Be Organized

“It’s hard to overstate how important it is to be organized and prepared when selling your business. Prospective buyers are going to want to know specific details about things like your operations and finances. If you don’t have this information readily available, you could come off as unprepared, which will drive prospects away from your business. So, put simply, my lesson is a little organization can go a long way. ” ~ Chris Christoff, MonsterInsights

2. Develop Strong Negotiation Skills

“I would say going through the sales process with my old business taught me the importance of developing strong negotiation skills. Understanding your true value, knowing when to compromise, and being confident in your decisions is crucial for selling your company and getting what you deserve. If you don’t know how to negotiate and highlight the value of your brand, you will lose out on a lot of money. This was all a surprise to me because I thought selling a business would be very cut and dry. I didn’t expect such nuance, and now that’s something I don’t think I’ll ever forget. ” ~ Daman Jeet Singh, FunnelKit

3. Discovering Identity Beyond Titles

“Selling one of my businesses was one of the most challenging yet rewarding experiences of my career. After building the company from the ground up, letting go was difficult but also clarifying. Through the process, I learned that my identity and self-worth were far more than just being a VP or CEO.

Although those roles were important to me, I am so much more as a human being. The business was an expression of my talents and hard work, but not the totality of who I am. Letting go allowed me to see myself more fully, beyond just my professional accomplishments.

I realized that success comes in many forms and that my worth is inherent. Selling the business opened up space for personal growth and new beginnings that I didn’t even know I needed. It was a surprising gift that I will always cherish.” ~ Scott Williamson, VP of Sales and Engineering, R. Williamson & Associates

4. Emotional Journey and Control Surrender

“Selling one of my businesses was the culmination of years of hard work, but it also taught me some unexpected lessons. The most surprising thing I learned was how emotional the process can be. Logically, I knew the business was just an asset to be bought and sold. But in reality, it was hard to separate it from my sense of self-worth and identity. I had nurtured that business from the ground up, and letting go was harder than I ever could have imagined.

The second surprise was realizing how little control I had once the process was in motion. There were so many external factors, like market conditions and regulatory issues, that could derail things at any moment. I had to surrender to the process and have faith that things would work out.

Finally, I was caught off guard by how much I missed being in the driver’s seat, even though running a business is demanding. There’s something addictive about being your own boss that’s hard to give up. Selling my business was absolutely the right move, but I learned firsthand that logic and emotions don’t always align.” ~ Adam Roach, CEO, Uppercut Tactical

5. Valuing Relationships Beyond Transactions

“One unexpected thing I learned from successfully selling my finance advisory business was the significant impact it had on my relationships with clients and employees. Throughout the sale process, I realized the level of trust and loyalty that had been built over the years and the importance of transparent communication in maintaining those relationships.

Witnessing the reactions of clients and employees to the news of the sale showed me how important the relationships we had built were and reminded me that our business was more than just a service provider.

It made me realize the importance of caring about people and being understanding in business, leaving me with a newfound appreciation for the human side of entrepreneurship.” ~ Michael Ashley, Founder and Business Expert, Ashley Insights

6. Preparing for Emotional Business Transition

“I was surprised by the emotional complexity involved in letting go of something I’d built from the ground up. Beyond the financial and logistical aspects, there was a significant emotional transition.

The process taught me the importance of preparing not just the business for sale but also myself for the personal shift. This experience also highlighted the value of building a strong, independent team that could thrive without my daily involvement, which facilitated a smoother transition for both the new owners and myself.” ~ Inge Von Aulock, CEO, Top Apps

7. Support Often Comes from Strangers

“One unexpected lesson I learned from successfully selling my business is that your biggest supporters often turn out to be strangers. It’s a tough pill to swallow, but sometimes your friends and family are the ones who doubt you the most.

Meanwhile, strangers are the ones putting their trust in you. And you know what? That’s okay. Business is business, and at the end of the day, it’s the support that matters, not where it comes from.” ~ Luke Beerman, Owner of Freedom Fence

8. Automated Solutions Boost Business Value

“One unexpected thing I learned from successfully selling a business is the transformative effect of leveraging automated solutions to enhance operational efficiency and attractiveness for potential buyers. At Notice Ninja, our SaaS platform’s ability to automate tax and compliance notice workflows was a game-changer for both our clients and our business valuation.

For example, when we integrated advanced automation technology into our platform, not only did we significantly reduce the manual data-entry workload for our users, but we also showcased how scalable and efficient our operations could be. This operational improvement was backed by concrete data: clients who fully adopted our automated workflows saw up to a 40% decrease in processing time and a 30% reduction in errors. These metrics were highly appealing to potential buyers, as they indicated a robust, future-proof system.

Moreover, my experience co-founding ANTS highlighted the importance of having streamlined operations. We concentrated on maintaining detailed documentation of processes and ensured that our team was aligned toward common goals. This alignment and systematic approach made the transition during the sale much smoother and reassured buyers of the business’s long-term viability and consistency. The unexpected lesson here was how much value potential buyers place on well-documented and efficiently run operations, as it mitigates perceived risks and enhances overall business value.” ~ Amanda Reineke, CEO and Co-Founder, NoticeNinja

9. Empowerment and Trust Drive Growth

“One unexpected thing I learned from successfully revitalizing and leading Five Guys Roofing was the profound impact of trusting and empowering your team. When I transitioned from a founding member to CEO, one of my initial challenges was scaling our operations without compromising our core values. Early on, we realized that our growth hinged not just on innovative marketing strategies but also on fostering a culture of trust and delegation.

We restructured the company to allow managers more autonomy, placing a significant amount of trust in their decisions. By doing so, we quadrupled our revenue from $3.3 million in 2015 to over $14.5 million in 2019. A specific example is how Brent, my father, trusted his sons, and in turn, we trusted our managers. This culture of trust and empowerment streamlined decision-making processes and fueled our rapid expansion.

Additionally, integrating customer feedback through platforms like Podium and PulseM played a crucial role. By actively engaging with our customers and addressing their concerns in real time, we significantly boosted customer satisfaction and built long-term relationships. This not only retained customers but also made our business more attractive and defensible in a competitive market. Our innovative approach to customer engagement and marketing was pivotal in solidifying our reputation as Arizona’s premier roofing specialist, ultimately making the company more valuable.” ~ Jonathan Stowell, CEO, Five Guys Roofing

10. AI Integration Increases Market Attractiveness

“One unexpected thing I learned from successfully selling a business was the intrinsic value of integrating AI-driven solutions to streamline operations and increase market attractiveness. For instance, with one of my ventures, Profit Leap, we developed an AI business advisor chatbot, HUXLEY, which helped small businesses navigate complex decisions effortlessly. This innovation not only improved our clients’ operational efficiency but also demonstrated the scalability and technological robustness of our business to potential buyers.

A concrete example of this impact was seen when we implemented the “8 Gears of Success” framework across multiple small law firms, boosting their revenues by over 50% year-over-year. This data-driven methodology showed potential acquirers tangible proof of consistent, scalable growth. During due diligence, these documented outcomes served as a compelling argument for the business’s long-term viability and growth potential, enhancing its market value significantly.

Moreover, my experience in onboarding technologies and automating financial management processes played a crucial role. By integrating advanced sales tracking and financial planning systems, we ensured complete transparency and operational efficiency. This level of precision and documentation reassured buyers, highlighting the business’s resilience and ease of transition, ultimately smoothing the sale process. These unexpected learnings underscored the importance of leveraging technology for operational excellence and making the business irresistibly attractive to potential buyers.” ~ Victor Santoro, Founder and CEO of Profit Leap

11. Cultural Alignment Enhances Transition Success

“As an entrepreneur who successfully sold a thriving tech startup, one unexpected yet invaluable lesson I learned was the profound importance of cultural alignment between the buyer and the seller.

At the same time, coming into this sale, I was mostly worried about the financials, valuation, and strategic fit with the acquiring entity. But as discussions proceeded, I realized that facilitating a seamless transition and a successful future necessitated more than an agreement on business goals; it required a thorough knowledge of and compatibility with the corporate culture of the buyer. This was most evident during the due diligence stage, where variations in their decision-making process, style of communication, and company culture began to come to the forefront.

My startup, which espoused a start-up moniker, thrived on a nimble and forward-thinking culture that embraced the philosophy of “move fast and break things.” The acquirer, although successful, was more silo-based and hierarchical. So, with this in mind, I ran a number of integration workshops and informal team events.

The work successfully bridged the gap in cultural misunderstanding and provided the foundation for great mutual respect. The latter was particularly important in terms of preserving team morale, customer satisfaction, and hitting the business goals post-acquisition.” ~ Adam Bogle, Senior Marketing Coordinator, Richards-Wilcox Canada

12. Timing Influences Sale Value

“I would like to share an unexpected lesson that I learned from selling my previous company. The first thing that hit me from the sale was just how much of a role timing plays. I found that the timing of a sale can dramatically affect both the value of the business and the ease of the transaction.

It’s true; timing isn’t everything, but it relates to just about everything—comedy or business sale. Understanding the dynamics of your market could turn a good sale into a great one. For instance, selling during a peak demand period for outdoor fitness equipment resulted in a higher valuation and more interested buyers.

I found this quite an eye-opener because it emphasized to me that market conditions and seasonal trends are critical and go a long way beyond financials and business health.” ~ Lucas Riphagen, Co-owner, TriActiveUSA

13. Professional Network Amplifies Sale Price

“One unexpected lesson I learned from successfully selling my business was the immense value embedded in our professional network, which I had initially underestimated. This realization not only boosted the sale price but also underscored the importance of strategic relationships in business growth and valuation.

Our extensive network of industry contacts, built over years of consistent engagement and trust-building, proved to be a critical asset. Potential buyers were particularly interested in the established relationships we had with key market players and influencers, which they saw as a gateway to future opportunities and collaborations.

This highlighted to me that a robust professional network can significantly enhance a company’s attractiveness and overall value during acquisition negotiations.” ~ Lucas Botzen, Founder, Rivermate

14. Client Trust Bolsters Business Marketability

“One unexpected thing I learned from successfully selling my business, Intrabuild, was the paramount importance of trust and transparent communication in fostering long-term client relationships. At Intrabuild, our client-centric approach meant that we personalized every design and meticulously planned each detail, which strengthened trust with our clients. This trust translated into rave reviews and strong word-of-mouth recommendations, which significantly enhanced the business’s marketability.

A concrete example that highlights this is our renovation project for a first-time homeowner’s co-op unit. The project involved a gut renovation of the kitchen and bathroom, relocating doors, and redoing walls. Despite numerous design changes and detailed queries, we maintained clear and consistent communication throughout. This hands-on approach not only resulted in a top-notch renovation but also garnered glowing testimonials that boosted our credibility. Building this level of trust made our business much more attractive to potential buyers, who saw a reliable client base and high customer satisfaction.

Another critical lesson was the importance of adaptability and problem-solving skills in overcoming unexpected challenges, particularly during the pandemic. Our ability to navigate stringent new requirements—like ensuring PPE for the crew and adhering to capacity restrictions—demonstrated our capability to handle crises efficiently. This adaptability was a key selling point, as potential buyers valued our proven ability to maintain project timelines and budgets despite external disruptions. These qualities showcased the resilience and robustness of Intrabuild, making it an attractive acquisition.” ~ Nick Chatzigeorgakis, CEO, Intrabuild

Image: Envato