For nearly 20 years, I worked in the tech industry, primarily with large public companies as a salesperson and sales manager. My role involved leading sales teams tasked with selling software systems that managed voice and data traffic for call centers. While this career was both rewarding and lucrative, it required constant travel and depended heavily on teams and processes beyond my control. Over time, I realized that the only person with true authority in a company is the CEO—an opportunity I wouldn’t have achieved anytime soon in my corporate trajectory. That realization planted the seed: I wanted to run my own business.
As a California native, I developed a deep appreciation for wine culture, frequently exploring wineries and enjoying the education and experiences they offered. My tech career often took me across the country, where I dined with clients and executives over wine. Those experiences, coupled with my entrepreneurial aspirations, led my wife and me to envision a new kind of business: a winery without vineyards. This unconventional concept stood out as a unique opportunity to combine my love of wine with my professional skills.
In 2004, we turned that vision into reality by opening the first winery in Rancho Cucamonga, California. This marked the beginning of my journey from corporate sales to entrepreneurship. Reflecting on my 20 years as the CEO of my own business, I’ve learned that while this transition is incredibly rewarding, it comes with its own set of challenges. Below are insights I wish I had known when I made the leap.
Key Lessons for Transitioning to Entrepreneurship:
- Your Leadership Drives Success: As the backbone of your organization, your ability to strategize and make key decisions directly impacts the growth trajectory of your business. You control the training and set expectations for your employees. Effective leadership sets the tone for your team and shapes the culture and direction of the business. The way you lead will determine how you and your employees overcome challenges and achieve long-term goals.
- Leverage Your Background: It is important to leverage your background when you make the switch to becoming your own boss. Regardless of the industry you started in and where you are headed, rely on your past successes, losses, skills developed and relationships you built throughout your career.
- Seek Constructive Guidance: Avoid relying solely on friends and family for feedback, they are more likely to offer reassurance rather than constructive criticism. Engage with people who understand both business fundamentals and your target market. Challenge them to question the viability of your idea and ask whether they would be willing to invest their own money. This will help you separate genuinely helpful advisors from those echoing your own biases.
- Create a Meaningful Culture: One of the most rewarding aspects of owning your own business is your power to create an environment where employees feel empowered, respected and valued. Whether you want to focus on collaboration, team initiatives or prioritize work-life balance, you will set the tone for how people interact and work together. Draw from your past experiences. What did you love or dislike about the previous companies you worked with? Where were there areas of improvement? Owning your own business gives you the freedom to align your company culture with your personal beliefs, creating a workplace where employees genuinely feel valued and motivated to contribute.
- Own Your Schedule: In the beginning, there will be plenty of long days and late nights, but no one has control over your schedule other than yourself. The freedom to be completely in charge of your own schedule is a perk that very rarely comes with a traditional corporate role.
- Plan for the Long Term: When you first embark on your entrepreneurial journey, creating a strong business model is key. You will need to implement support systems, training programs and operational guidelines to ensure sustainable success. Establishing both short-term and long-term goals is essential for maintaining focus and accountability, allowing you to measure progress over the years.
- Enjoy Job Security in Uncertainty: As the owner of your own business, your company cannot be sold or merge with another entity unless you directly initiate it. By maintaining control, you can guarantee there will be no surprise layoffs, job eliminations or sudden organizational changes that impact your employees.
- Embrace Accountability: Leaving a secure career with no risk is daunting. You are leaving behind a steady paycheck and the stability of a 9-to-5 job. Stepping into entrepreneurship requires you to embrace uncertainty and take ownership of the success and challenges. You need to be resilient, adaptable and willing to make sacrifices to reach your goal.
Today, as the CEO of Waters Edge Wineries, a craft winery franchise system, I’ve seen the rewards of taking that leap into entrepreneurship. By applying the strategies mentioned above, we’ve grown into a national brand, bringing wine culture to communities across the U.S. While the transition from corporate life was intimidating, it ultimately allowed me to create meaningful, impactful business.
Starting your own venture is never without risk, but it’s also the first step toward building a life on your own terms. For those considering this path, remember: with the right mindset, strategy, and support, the rewards far outweigh the challenges.
Contributed by Ken Lineberger, Founder and CEO, Waters Edge Wineries. After spending nearly 20 years in sales and marketing with a large software company, Ken Lineberger co-founded the first micro winery in Rancho Cucamonga along with his wife Angela in 2004. He saw an opportunity to take the best of what he had experienced in the corporate world to a small business model. He envisioned building a template that could be replicated in other venues across the United States, and with the model perfected, Waters Edge Wineries was created as a franchise brand in 2012, selling winery franchises nationwide.
