Bill Powers has built companies, ridden them through to exits, and most recently raised half a billion dollars for a minority stake in his own startup.
In our interview on the DealMakers podcast, Bill Powers shared his formative experiences, what he has learned about sales that led to a $500k pilot customer, the benefits of not raising money, and the foundation he is passionate about.
Bill Powers was born and raised in Boston, Massachusetts. He describes it as a blue-collar upbringing, in a part of town where people were hardworking and meant well.
It was before kids spent their childhood glued to mobile devices. You got outside and did stuff. In the fall you played football. In the winter you went ice skating on ponds and played basketball. In the summer you rode your bike and boxed with other kids in the neighborhood.
Bill’s father was at Pearl Harbor on the morning it was attacked during WWII. From his dad, he learned how to treat others with respect, and never recalls hearing him have a bad word to say about anyone.
At 17 years old his father passed away. During the following years, he learned the advantage of having some emergency capital for the unexpected. Even if that was just a $20 bill hidden in his shoe. It was a time that he had to learn to get comfortable with uncertainty. A talent that certainly helps in entrepreneurship.
If that wasn’t enough Bill and his wife lost their first child during delivery. It was completely unexpected. He describes a painful month, with his son in the morgue and his wife in a coma in the hospital, and seven serious surgeries. It turns out that there were six documented and preventable errors that occurred. A fact that drove them to create the Luke Vincent Powers Foundation. It is a way he continues to give back and tries to help others, after a lot of therapy and prayer himself. Fortunately, today he is a proud parent of a 17-year-old son, Lorenzo, who is the joy and light of his life.
Discovering & Mastering Sales
So much of entrepreneurship is sales. From fundraising, recruiting, and gaining customers, it is all sales. He had friends in the NBA. He got into sports marketing. He got them shoe deals and contracts. He ended up starting his own basketball school for kids.
Then Bill fell into nightclub promotions and ended up running some pretty large clubs before starting his own.
Radio was the next stop in his career. That included working sales for Westwood One and American Radio Sports. Along the way, he has picked up a lot of valuable sales skills, which have certainly been instrumental in the processes at Cambridge Mobile Telematics.
He learned to listen more than you talk. To find out what others need, versus trying to sell what you have. To keep learning, work hard, and be respectful while being fearless in communicating.
One of his big takeaways in sales has been to be sure you are strategic and are connecting with the real decision-makers at the top first. If you aren’t, more often than not you are going to be talking to people who can only say no.
Instead of just calling people out of the blue and spamming them, he recommends finding those you can create meaningful partnerships with and helping them solve a problem.
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