Embrace Legacy, Leadership, and Life After the Exit with Bill Davey

In this episode, you’ll hear from Bill Davey, a successful entrepreneur, author, and business automation expert with extensive experience across various industries. Bill, who has founded over 20 companies and achieved multiple multimillion-dollar exits, focuses on empowering businesses through technology and effective marketing. Despite his accomplishments, Bill opens up about the challenges of "founder depression" after significant business exits, a topic that resonates with me.

Bill shares his early entrepreneurial spirit, sparked by his family’s background in sales and his exposure to business from a young age. He discusses formative experiences working at a bank in high school, where he observed high-stakes deals and developed a fascination for deal-making and business ownership. While he enjoyed notable successes, Bill reflects on the valuable lessons learned from his failures, viewing them as essential steps in his journey. He emphasizes the importance of resilience, acknowledging that some of his most important insights came from overcoming setbacks, dishonest partners, and tough financial challenges.


EMBRACE FAILURE AS A LEARNING OPPORTUNITY

Bill highlights that failure is not just an obstacle but a powerful teacher. He likens this process to crafting fine wine, where the difficult times—referred to as the “struggles in the valley”—play a crucial role in producing something exceptional.

Bill recalls a story about launching a product that just didn’t hit the mark with customers. Instead of seeing it as a failure, he used it as a chance to gather feedback, rethink his strategy, and ultimately come up with a better version of the product. This shows us that setbacks are actually a big part of growing, both personally and professionally. When we recognize that nothing in entrepreneurship is a walk in the park, we can build resilience and take a more positive approach to whatever challenges come our way.

CULTIVATE TRUST AND BUILD STRONG RELATIONSHIPS IN BUSINESS

Bill shares some great stories about how the trust he built with his mentors and early employers helped set him up for success down the line. There was a moment when a mentor gave him some crucial advice that not only helped him dodge a costly mistake but also made their professional relationship even stronger.

This just goes to show how vital it is to have a supportive network—whether that’s through partnerships or mentorship. When you have people around you who can offer guidance and encouragement, it makes a world of difference. The best business deals often come from those personal connections and the trust you cultivate, which are key for navigating the ups and downs of entrepreneurship.


ACKNOWLEDGE EMOTIONAL CHALLENGES AFTER BUSINESS EXITS

Bill Davey shares some real talk about the emotional rollercoaster that can come after selling a business. He points out that this transition isn’t always as smooth as it seems. Many entrepreneurs, after reaching what should be a huge milestone, often find themselves feeling a bit lost or empty once they step away from the hustle and bustle of their daily grind. It’s not uncommon for people to go through an identity crisis because their business was such a big part of who they were.

It’s important to recognize and acknowledge these feelings instead of brushing them aside. Celebrating the exit is great, but that doesn’t mean you’re done figuring out what’s next. This is a perfect time to take a step back and really reassess what you want from life moving forward. Instead of just filling your days with leisure activities or distractions, strive for a balance between work and personal life. Finding that balance is key to long-term happiness and fulfillment, as it gives you the chance to redefine your purpose and discover new passions beyond your previous business.


TAKE OWNERSHIP TO DISCOVER TRUE FULFILLMENT IN YOUR BUSINESS

Bill Davey notes that when times get tough, many business leaders might look for alternative investment opportunities, thinking it could help diversify or safeguard their wealth. But he makes a great point—real fulfillment and satisfaction often come from being directly involved in work that resonates with your passions and expertise.

When he was feeling uncertain and tempted to put his money elsewhere. Instead of going that route, he decided to refocus on the core areas of his business where he felt most comfortable and knowledgeable. When faced with challenges, consider diving back into what you know and do best. Active participation in your business can lead to the most rewarding outcomes, reinforcing the idea that ownership is key to both personal and professional satisfaction.


IDENTITY BEYOND BUSINESS

A lot of entrepreneurs invest so much of themselves into their businesses that it can be tough to separate their self-worth from their professional successes. This strong connection can make it challenging when they think about life after selling their companies. Bill shares how lost and disoriented they felt after selling their business—even though they had achieved what many would call the peak of success. They came to realize that they had tied their personal value to their business's performance, leaving them with a deep sense of emptiness once that chapter was over.

To navigate this tricky transition, it’s really important for entrepreneurs to build a sense of self that isn’t solely tied to their business. This means exploring interests, passions, and relationships outside of work that bring them joy and fulfillment. By nurturing these parts of their identity, entrepreneurs can make a smoother transition when it’s time to step away from their companies, helping to minimize those feelings of emptiness or purposelessness that can follow a sale or retirement.


THE TRUE MEANING OF SUCCESS AND WEALTH

The concept of true wealth is often misunderstood. It is not solely about the size of one’s income or the luxuriousness of one’s lifestyle. Instead, real wealth is defined by financial stability and the ability to make money work for you. For instance, Individuals living in multimillion-dollar homes who, despite their lavish surroundings, are grappling with significant debt. Conversely, someone leading a more modest lifestyle may possess true financial security through savings, investments, and a solid understanding of their financial health.


UNDERSTAND BUSINESS MODELS

Bill Davey brings up a really interesting point about business models, especially the benefits of a low-margin, high-volume approach. This strategy is all about building strong relationships with a lot of clients instead of just focusing on high profits from a few customers. Instead of security systems, Bill began offering comprehensive website services for just $49 a month. He understood that while the initial margins were thin, the potential for recurring revenue was significant. Over time, he noted that the average client would spend about $100 monthly on additional services, illustrating how a small initial investment could lead to greater returns in the long run.

But here’s the catch: there isn’t a one-size-fits-all formula for success in entrepreneurship. What really matters is recognizing your strengths and figuring out how they align with different business models. I follow a high-margin, low-volume model, which means I focus on offering premium products or services at a higher price but sell fewer of them. Bill, on the other hand, has a high-volume, low-margin approach. He serves a ton of clients at lower prices, and he shared that if he were to lose a small percentage of those clients, it wouldn’t hit his revenue too hard because he has so many to begin with.

This really highlights that both models can be successful; the trick is finding what works best for you. It’s all about understanding your own talents, skills, and how you execute your business strategies.


THE BALANCE OF PRICE, QUALITY, AND SERVICE IN YOUR BUSINESS MODEL

Bill Davey emphasizes that it’s nearly impossible to excel in all three areas simultaneously. Usually, companies can only hit two out of three, which means you need to make some smart decisions about what matters most for your goals and your audience.

He’s figured out how to blend high-quality service with competitive pricing. He delivers top-notch products and ongoing support to his clients, all while keeping the quality up to their expectations. By honing in on these two aspects—quality and affordability—he’s created an attractive offer that keeps customers coming back.

Entrepreneurs need to identify which two elements of the price, quality, and service triangle they want to focus on in their business strategy. By understanding this balance and adapting their tactics accordingly, you can craft strategies that not only drive success but also ensure long-term growth.


Tune in to this episode of DealQuest to hear Bill Davey’s powerful insights on leadership, resilience, and building a legacy that goes beyond profits and career milestones.

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Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!