For almost two decades, I worked in the tech industry, mainly dealing with large public companies as a salesperson and sales manager. My job involved leading teams that sold software systems to manage voice and data traffic for call centers. Although the career was both rewarding and well-paying, it demanded constant travel and relied heavily on teams and processes outside my control. Over time, I realized that real power in a company lies with the CEO—a position I wouldn’t reach soon in my corporate path. That got me thinking: I wanted to run my own business.
As a native Californian, I developed a great love for wine culture, often visiting wineries and enjoying the learnings they offered. My tech career took me all over the country, dining with clients and executives over wine. These experiences, paired with my entrepreneurial dreams, led my wife and me to imagine a different type of business: a winery without vineyards. This unique idea was a chance to blend my passion for wine with my professional skills.
In 2004, we brought this vision to life by opening the first winery in Rancho Cucamonga, California, marking my shift from corporate sales to entrepreneurship. Reflecting on my 20 years as the CEO of my own business, I’ve learned that while this journey is extremely fulfilling, it comes with its challenges. Here are insights I wish I had known before making the leap:
Your Leadership Drives Success: As a leader, your ability to strategize and make critical decisions directly influences your business’s growth. You set expectations for your employees and control their training. Effective leadership not only shapes the company’s culture and direction but sets the tone for overcoming challenges and achieving long-term goals.
Leverage Your Background: When transitioning to being your own boss, draw on your background. No matter the industry you started in or are moving into, tap into your past successes, failures, skills acquired, and relationships developed throughout your career.
Seek Constructive Guidance: Don’t just rely on friends and family for feedback, as they might just provide reassurance instead of constructive critique. Engage with individuals who understand business basics and your target market. Challenge them to assess the viability of your idea and ask if they would invest their own money in it. This will help you differentiate genuinely helpful advisors from those who just echo your own views.
Create a Meaningful Culture: Owning your business allows you to create a work environment where employees feel valued, respected, and empowered. Whether you emphasize collaboration, team initiatives, or work-life balance, you set the tone for how people interact and work together. Reflect on your past experiences—what did you like or dislike about previous workplaces? What needed improvement? Owning a business gives you the freedom to align company culture with your beliefs, making the workplace a space where employees are truly motivated and valued.
Own Your Schedule: Initially, expect long hours and late nights, but remember that you control your schedule. The freedom to manage your own time is a rare perk in traditional corporate roles.
Plan for the Long Term: Starting your entrepreneurial journey requires a solid business plan. Implement support systems, training programs, and operational guidelines for sustainable success. By establishing both short-term and long-term goals, you can maintain focus and accountability, enabling you to track progress over the years.
Enjoy Job Security: As a business owner, your company cannot be sold or merge with another entity unless you decide so. By maintaining control, you can prevent surprise layoffs, job eliminations, or sudden organizational changes that affect your employees.
Embrace Accountability: Leaving a secure career and a steady paycheck is daunting. Stepping into entrepreneurship requires embracing uncertainty and taking responsibility for both successes and challenges. You’ll need to be resilient, adaptable, and ready to make sacrifices to achieve your goals.
Now, as the CEO of Waters Edge Wineries, a craft winery franchise system, I’ve experienced the rewards of this entrepreneurial leap. By applying these strategies, we’ve become a national brand, bringing wine culture to communities across the U.S. Although the shift from corporate life was intimidating, it ultimately allowed me to create a meaningful and impactful business.
Starting your own venture involves risks, but it’s the first step toward building a life on your terms. For those considering this path, remember: with the right mindset, strategy, and support, the rewards far exceed the challenges.
Contributed by Ken Lineberger, Founder and CEO, Waters Edge Wineries. After almost 20 years in sales and marketing with a large software company, Ken co-founded the first micro winery in Rancho Cucamonga with his wife Angela in 2004. He aimed to bring the best of what he experienced in the corporate world to a small business model. His vision was to develop a template that could be replicated elsewhere in the U.S., and with that model perfected, Waters Edge Wineries became a franchise brand in 2012, selling winery franchises across the nation.
