My biggest challenge was letting go.
When I launched ParkWhiz in 2006, I was used to completing tasks on my own and doing things a certain way, from reporting financials to servicing accounts. As the business began to scale and we brought on employees, I quickly realized I had to let go of the notion that everything would be done exactly the way I wanted it, every time. Not only was that inefficient, but it was demoralizing to employees if I couldn't trust and empower them to find their way.
So I made a vow to let go of the tasks I once owned and began mastering delegation while maintaining the high standards I had set. And, yes, I even slept better at night knowing the burden was no longer fully mine to own and execute.
Transitioning from entrepreneur to CEO is a difficult shift. After all, conceiving a company is in an entrepreneur's blood, and not all feel comfortable leaving behind the excitement of launching a company of their own to take on a role that involves more red tape and general process. While many technology startup founders can grow bored after their business goes from dream to reality, I stayed on and continued leading as CEO--but if an entrepreneur can't let go, the business won't grow.
Aside from letting go, I learned a lot along the path from entrepreneur to CEO:
1. When to Pay Yourself and Bring on Staff
I waited four-and-a-half years to give myself a salary. During that time, I worked long hours from home building the company, doing everything from administrative work, sales, marketing and more. In addition to figuring out when it was appropriate to pay myself, I was hesitant about bringing on staff, knowing no matter how exceptional a candidate was, they would never have the same stake in the business as I did. But hiring new talent was imperative, and the natural next step in the company. To that end, entrepreneurs must learn to set expectations with their first employees and be realistic with what they can offer in the early years of the business.
2. Don't Ignore the Little Guys
After launching the company, I started working with smaller parking operators, educating them on the product and explaining how it would make operators money. Once this sector of the market understood the product and saw the benefits, I felt comfortable approaching the mid-sized and larger players. This approach can help build the successful foundation of any venture and gives the necessary "wins" to tackle those higher-level goals.
3. When to Focus on Long-Term Planning
There came a point when I needed to delegate day-to-day tasks in order to focus on scaling the business. As CEO, I needed to step back, develop the strategic roadmap for the company and identify new opportunities that would enable the business to grow toward its goals. This is a pivotal mind shift for any entrepreneur. In 2007, the company was a hardware-sensor-based one, and I was trying to pivot it into the business that it is today. After investing endless hours and years into the business, I got caught up in the tactical day-to-day grind. When I finally looked up, I realized the vision I set out to achieve was unlikely to be realized, and I knew we had to make a difficult choice to push on or pivot. While my heart was in the former business, my brain told me we needed to shift hard to the model we are today. That was a difficult moment for me to reconcile, but knew it had to be done.
4. Look for Support Outside Your Company, Through Your Family
This was the most important lesson for me. I was fortunate enough to have a supportive wife who allowed me to follow my dream - it also helped that she was a lawyer and CPA and could offer pro-bono guidance. Young entrepreneurs should have serious conversations with their families about what their commitment will be. Even if their spouse, parents, siblings or friends don't formally have a position at your company, their support could mean the difference between building a thriving business - or letting a dream fall by the wayside.
Jumping to CEO has been one of the most rewarding experiences, allowing me to push business further than I could ever imagine. However, just remember to let go - it may be difficult at first, but it helps reveal the full potential that any company has in its industry.