Neil Patel

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Bill Powers is the co-founder and CEO of Cambridge Mobile Telematics which develops DriveWell, a complete telematics, and behavioral analytics solution to improve safety. The company has raised over $500 million from top tier investors like Softbank Vision Fund.

In this episode you will learn:

  • Cambridge Mobile Telematics’ business model
  • Their $500M funding round
  • What Bill loves about Softbank as an investor
  • The problem with autonomous driving 
  • His one piece of business advice for aspiring entrepreneurs


For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

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Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400 million (see it here).

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

About Bill Powers:

Bill Powers has played a vital role in building and managing a number of successful organizations at companies like Swoop and Bill Powers is recognized as a leader in emerging media and technology.

Bill Powers established the Luke Vincent Powers Foundation in memory of his son, Luke.

Bill Powers serves as the Foundation’s President, which supports disadvantaged children.

Connect with Bill Powers:

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Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. Today, we have an exciting founder. We’re going to be learning about how to create a company that has a business model that is very, very strong, where you’re able to control your own destiny. I think his journey, personally and professionally, really made him who he is today, and I think you’re going to find him remarkable. Without further ado, Bill Powers, welcome to the DealMakers show today.

Bill Powers: Thank you so much, Alejandro. How are you?

Alejandro: Very well. So, born and raised in Boston. How was life growing up there?

Bill Powers: It was great. I grew up in a blue-collar part of town and learned some valuable lessons from hardworking, well-intended people. I wouldn’t change it. It was an interesting upbringing.

Alejandro: I know that when you were 17, a very impactful event happened in your life, and that is that your father passed away, and a sequence of events happened there that made you learn a lot of lessons in life. Can you tell us what happened there?

Bill Powers: My dad was an older guy. He was in WWII. He was actually at Pearl Harbor the morning they were attacked, so I got a front-row seat on watching how the greatest generation performed, behaved, and treated people with respect. He was a really good dude. He was a good man, and he taught a lot of life lessons. Although it’s traumatic for any young person to lose a parent, it had a profound effect on me; I suppose positive and negative. But I’m not the only one that’s been through tragedies. I try to look at it as the glass half-full.

Alejandro: Absolutely. What were those big lessons that you took away from your father growing up? I’m sure when you have that type of accountability and responsibility after you serve in events like WWII. I’m sure it’s remarkable what you were able to learn from him as well.

Bill Powers: I’m a dad now. My son is 17, and I think about my dad a lot because of that. But a couple of things that I noticed and I talk about it today, particularly when we live in such divisive times, unfortunately, polarized community. I never heard him say a bad word about anybody. He was always measured, a traditional Irish Catholic growing up in Boston. He had a lot of dear friends from his war experience, and he’s just one of those guys that was polite, was a gentleman, was very fastidious in how he dressed, and how he spoke to people. I think he was a model of real dignity, and he conducted himself with such grace. Those are some of the lessons I remember.

Alejandro: How did you get into basketball? 

Bill Powers: What else were you going to do? You just start playing. 

Alejandro: Right.

Bill Powers: I grew up in a time where there wasn’t other stuff to do, so you got on your bike, you went to the park, and depending on the season is the sport you played. In the fall, you played football. In the winter, you played basketball indoors or grabbed some skates, and skate outside. It used to be cold back then. The ponds would freeze over, and you’d find a place to skate. Then in the spring, you’d play baseball. In between, you’d just box. Whoever you could hit, you’d just box somebody.


Alejandro: That sounds dangerous, Bill. I’d like to also ask you because after your dad passed away, there was a sequence of events, for example, losing your home. I’m sure that has also made you who you are today, and also dealing with uncertainty because I think that also being an entrepreneur is being able to deal with uncertainty. What happened during the sequence of events, and how would you say that it has made you what you are today?

Bill Powers: I would say that uncertainty is a good way to describe it. When you’re a child, and a parent passes, it’s obviously shocking to anybody. Unfortunately, my parents didn’t prepare for what I would describe as life events, so we ended up in a challenging situation in terms of where we were going to live or where we would find a place to live. That was traumatic for me. I think it caused me to grow up quickly. I remember, as a kid, I always had $20 hidden in my shoe or hidden in my bag or hidden in my wallet just in case. Twenty dollars to me, back then, was a ton of money. But it always was, “What if something happens? What do we do?” Those lessons really stayed with me.

Alejandro: Got it. Absolutely. Then fast-forwarding, tell us about your experience as a pro basketball player.

Bill Powers: I was never a pro basketball player. I played in high school and college. I had a chance to play overseas. I did not do that. I ended up getting into — I would describe it as sports marketing. A few of my friends played in a league. They played in the NBA, so they asked me to do some shoe deals for them in marketing. That was an interesting time, so I did a couple of contracts for some players and made some money doing that. I started my own basketball school for children with a friend of mine, and continued to grow and sharpen my skills of communications and dealing with hiring and staffing and people and personalities and employees. It was remarkable. When I look back at it, the same stuff we’re all doing today, I was doing then. I just didn’t know it. I didn’t know that I was managing or leading or financing or things of that nature.

Alejandro: Quite a change from that to night clubs. Why night clubs?

Bill Powers: I don’t know. It just kind of happened. I was in school. I started doing nightclub promotions and working the doors to nightclubs. When I finished my schooling, I had an opportunity to work at and run some large nightclubs, and I also had the opportunity to have my own. When you’re young, and silly, and single, you’re just making cash, and you don’t really think things through. I didn’t have the opportunity to come from a childhood with a plan and two stable parents to say, “You’re going to do well in school. Then you’re going to go to this college. Then you’re going to get an advanced degree.” To me, it was, “How are we going to pay the rent?” I think that’s probably how I ended up in that situation. And I say that with a big smile on my face because it wasn’t a bad thing. It was just all I knew. 

Alejandro: I hear you. Then after this is when you started working for American Radio Sports and Westwood One. What was one lesson that you got from working at American Radio Sports and then one lesson that you got from working at Westwood One?

Bill Powers: I think the lessons are the same. Those were both sales positions. I learned that it’s better to listen more than talk, and don’t sell what you have. Try to find out what somebody needs. I think those two scenarios allowed me to grow quickly in terms of being a revenue producer or a salesperson. I had no intention of being a manager or growing or doing anything like that. I was just trying to make a living, but I would say the lessons to learn are to study, to be fearless, be respectful, to work hard, which enabled me to start to develop a really strong sales career.

Alejandro: Very cool. That’s something that people typically don’t get, especially, I’m sure that there are a lot of people that are thinking about fundraising too or selling their product or the experience or whatever that is, but when you’re able to do what you just mentioned, which is to a certain degree fulfilling concerns is where you’re able to take the closing rate to the next level. I love that you touched on that. 

Bill Powers: When you talk about closing rate, Alejandro, I think it’s important that there are salespeople and sales programs that talk about volume, and certainly, I think that has value, but as a salesperson, if you do your research and you’re targeting the appropriate customers, and not being afraid to get to the decision-makers, it doesn’t end up about being about closing rate, it’s actually communicating with people where you can develop meaningful partnerships to help solve a problem. I find it much more rewarding to spend time there than just calling people out of the blue.

Alejandro: And it’s typically like when you were talking about finding what people need. Is there a typical process that you’ve seen that works when you’re engaging with someone and communicating with them, especially for the folks that are listening?

Bill Powers: Yeah. I think it’s different now. It would be very easy for me to say what you should do. I’m now an older guy, which I’ve been through some things, so I think there are two answers to that question. One would be as a young salesperson, don’t waste your time dealing with people who can only say no. In other words, if somebody’s the middle manager of some division of a company, they don’t have the ability to say yes to whatever program you’re representing. Don’t waste time there in thinking that you’re going to do a good job. I would highly recommend a book called Strategic Selling, by Miller and Heiman. I think what’s more important is getting to a decision-maker out of the gate and ask them to direct you to the right people. So, when I was coming up, I used to get on the phone early or late at night because typically CEOs or Chairmen of companies or real decision-makers would end up being in their office early without distractions or in their office late without distractions, and you could get to the right people and have a conversation. What I found was, as a young person, those senior executives would give me the time of day more often than not because they realize that I was hustling and understood their schedule. In terms of what I do now, I would say that we have definitely a recipe at Cambridge Mobile Telematics that everybody follows. It’s more a team selling, strategic-selling approach. We don’t want to talk about an account if we’re talking to people who can only say no and can’t say yes. I think, also, when you have people who are able to collaborate and share in a team environment, everybody wins.

Alejandro: Absolutely. Then after your experience with Westwood One, then you started at had quite an impact for you and in your professional career as well, and you were there for quite a bit for almost eight years. What were you guys doing at, and what was exactly your role?

Bill Powers: One of my mentors — this was interesting. I was doing quite well at Westwood One, and one of my mentors, a gentleman named Al McGowan, reached out to me and said, “I need you to meet me at this venture capital office in Boston.” It was actually Bessemer, in their old office building. It was an old house. It was an unbelievable pitch. He said, “I can’t tell you what we’re doing. We only have funding for six months, and you need to take a 50% cut in pay.” I didn’t have any children at the time, so I said, “Okay. That sounds good,” because I knew I wanted to get into a high-risk, high-reward environment. At that point, I thought venture capital was the coolest thing in the world. So, I signed up for that. I was employee number five at We really grew. The business was the largest private, public partnership. It was with the United Stated DOT, and we would give traffic information and sell advertising units against that on radio, television, and one of the first mobile phone platforms. Ironically, we survived the first bubble, but then post-9/11, it became under the Department of Homeland Defense to help cities with evacuations and things of that nature. We ended up going public and selling it to Navteq, the mapping company. Then Navteq subsequently sold to Nokia, the phone maker. 

Alejandro: I’m sure that this, for you as well, was super helpful to see what the full cycle of a company looks like.

Bill Powers: It was very helpful. It was rewarding. It was humbling. I learned a lot of really good lessons and really bad lessons. I learned a lot.

Alejandro: What is the top good lesson and the top bad lesson that you took away with you?

Bill Powers: I think the top good lesson was strong leadership and having a measured approach and communicating fearlessly but respectfully. We had a wonderful CEO. I talked to him recently, a couple of weeks ago — a wonderful guy, very measured, very balanced, smart, smart guy. The worst lesson was the inverse of that. There were people that were duplicitous, and backbiting, and the more money that gets involved, the more you see the negative spots of some people. 

Alejandro: Understood. Then during this time, as well, a very important event happened, which led to starting the Luke Vincent Powers Foundation. Can you touch on this?

Bill Powers: Yeah. It’s very kind of you to bring that up, Alejandro. In 2000, my wife and I lost our first son, Luke. We had a very normal pregnancy and went in to deliver Luke at a Boston teaching hospital. Luke died during delivery, and later, it became clear through various publications, there were six documented preventable errors that occurred, which led to his death. Unfortunately, my wife, at the time also nearly died. She became very ill, and she had, I think probably seven life-saving surgeries. She was in a coma for well over a month. It was a very interesting time for me because I spend a month, literally, in the hospital with my son in the morgue and my wife in a coma. That definitely shapes perspective.

Alejandro: 100%. How would you say that shaped your perspective and also the way that you look at life because, obviously, when these types of events happen, everything is altered?

Bill Powers: I will say that it’s not like a Hallmark movie. When somebody comes up from a coma, they don’t just wake up, and there are choirs of angels singing, and everybody cries, and then they drive home. It’s very painful to watch. For me, I would also like to say that I wish I came out of it quickly, but for a fair amount of time, I struggled with and still struggle with PTSD. I was very angry at the time and very confused because on one hand, our son had died, and on the other hand, I literally had to help my wife with the most basic of human tasks. So, it was a really hard time. I would say that I came out of that through a lot of therapy and a lot of prayer, and then that’s when I turned the corner and started to feel really empowered about giving back and helping and making a difference. So, we started the foundation. We worked with the teaching hospital in Boston for an annual lecture series. I’ve done a lot of public speaking for healthcare improvement in terms of what residents and doctors and others should be going through. The old standard of hospital is, if you’re not awake for 25 hours, and it’s not us against the world, you’re weak. When delivering children and delivering a life, you should probably be more measured than that. That feels reckless to me. So, that’s the type of stuff we try to do. I say this quite often, “I’m not okay with what happened, but I wouldn’t change anything. We have a beautiful son, Lorenzo, who’s now 17, who is absolutely the joy and light of my life. He is just a wonderful kid.

Alejandro: And Lorenzo, what a wonderful name. I’m biased because I’m Spanish but good choice.

Bill Powers: I’m Italian, Irish, Spanish, and German. My middle name is actually Vincent, Vincenzo. We were going to go with Lorenzo Vincenzo, but my last name is Powers, so it kind of fell flat. He’s Lorenzo William.

Alejandro: I know that now, fast-forwarding to your latest chapter, obviously, here’s the time where you brought your own business to life. I know there was a time where you were approached, in 2010, by a private equity friend. That led to certain events that got you where you are today, so what happened there?

Bill Powers: I had left the combined entity of, Navteq, and Nokia. I really was starting with a new company and doing well and onto the next journey. I was approached by a gentleman who was a partner to a private equity firm here in Boston, and he said, “I’d like to introduce you to somebody.” I met my two business partners, Dr. Hari Balakrishnan and Dr. Sam Madden, both tenured professors at MIT. Hari is one of the world’s living experts in mobile sensing, and Sam is one of the world’s leading experts in artificial intelligence and big data processing. We really hit it off, and they asked me to join as their partner and be the CEO. I often chuckle when I hear that because it was the CEO of nothing. It was literally a couple of grad students working with the university, developing code. They had done a research project at MIT called Car Tel, which was Car Tell Maddox. This was back pre-2010, Motorola razors and smartphones were not as omnipresent as they are today. That’s for sure. They had this interesting idea, and I really enjoyed them. They’re really nice, wonderful people, and it felt like a good fit.

Alejandro: Then, what happened next? What were the next steps to really bring this to life, and what has been that journey so far?

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Bill Powers: They asked me to join as their CEO. We had laptops and people sitting on milk crates, and nobody making any money, and just developing code, and having conversations with people. Early on, we decided not to raise any venture funding for a variety of reasons, probably the biggest, which is we weren’t sure where the business was going, and to raise money just based on our team and giving up control probably didn’t make sense at the time. So, we felt really good about where we were going, but not sure where the journey was taking us if that makes any sense. So, we raised a National Science Foundation Grant, which was brilliant. I would encourage all young entrepreneurs to look into that. I put up a personal credit facility, and off to the races we went. Probably seven to ten months after that, we negotiated a $500,000 pilot with one of the largest auto insurance companies in the world to help them solve this notion or this problem of insurance-based telematics on the smartphone. 

Alejandro: At that point, what ended up being the business model, so that the people listening get it for Cambridge Mobile Telematics?

Bill Powers: It’s a SaaS model, so we record driving behavior on smartphones. It is an opt-in model. We do rewards for good driving, and we receive a fee from our insurance partners or automotive partners or our wireless partners, which is a monthly recurring-revenue service fee. We’re currently operating in 25 countries around the world, with close to 40 customers.

Alejandro: And everything started with a $500,000 contract. Is that right?

Bill Powers: It actually started before that, but yeah, that was the first.

Alejandro: Of course. I mean, the first good validation. Not bad.

Bill Powers: To be fair, that was a pilot, so that could have gone south in a hurry. We’ve been very lucky and fortunate along the way. I always feel uncomfortable talking about this because you say the words, and it sounds easy, but there was and continues to be many sleepless evenings.

Alejandro: Got it. Maybe like one sleepless evening that you ended up making a decision, and that ended up being a good choice that maybe you could share with us?

Bill Powers: Yeah. I think along the way, Hari and I, in particular, really focused on “keep getting to the next milestone and keep maintaining control.” I think the biggest thing we’ve always done is we’re really customer-centric, and we communicate a lot with our customers. That trust has been built over the last decade, which is really remarkable to witness, and continues today. If you fast-forward to what’s happening, today, with these uncertain times, our business is thriving, and our relationship with our customers has gotten even deeper.

Alejandro: If you could describe, especially to the listeners, what does it look like when you remove the “who is right” and you really embrace the human relationships, and you do that with big customers. What does that look like?

Bill Powers: I think I can only speak through my lens, but what it looks like is, the person that you’re talking with or trying to solve a problem for or negotiating with, that person is typically dealing with the same issues you are, whether it’s in the middle of a global pandemic, or a sick child, or a problem with an employee at work. So, as opposed to negotiating, I think we’ve done very well with just collaborating. Collaborating, communicating with each other to find out who has what needs, and how can we create long-term, meaningful partnerships that result in everybody sharing the risk and everyone sharing the reward? We’re in a position as an organization because we’ve maintained financial and physical control of our organization that we can be creative in any deal we strike.

Alejandro: Very cool. I know that you guys have raised also quite a bit of money. You guys were in very good shape, controlling your own destiny, but SoftBank came knocking.

Bill Powers: Yeah. I expected this topic to come up, Alejandro, so let me say that I want to make sure that everyone who hears this understands that in spite of what you might read, SoftBank is a fantastic business partner. We were not raising money. We did not have a banker. We’ve never had any debt. We’ve never had any concern like, “Oh, my goodness. We need to go raise money.” We were just growing organically and quite frankly, happy to do so. Because our profile was increasing, many large private equity firms or growth equity firms came knocking and wanted to talk, and I’m very proud to say, we talked to all of them and met with some of them, whether it was a small VC or even an investment banker, we talked to everybody because it was an opportunity for me to feel my intellectual curiosity and learn along the way. When we learned, we got better for the next conversation. So we were introduced to our partners at SoftBank through a mutual connection, a professor friend of one of my business partners, and the process went very quickly. We had received three term sheets throughout the process. But term sheets is probably not the right word. What a deal would look like, indication of interest type thing throughout the process, and SoftBank was depending on how you look at discounted things. The second or the third-highest valuation we received. They were not the highest. What I try to stress to people is that everybody sees the headline of 500 million, which was really just a result of the growth, and the stability, and the revenue our company had at the time. SoftBank is a true minority investor. They are a fantastic business partner, and for those who aren’t familiar with SoftBank with the vision fund beyond the headlines, they have a group called the Operating Group. The Operating Group’s sole purpose is to support companies and entrepreneurs and founders. They connect you with other folks within the SoftBank ecosystem or even outside the SoftBank ecosystem. So, it could be government affairs. It could be countries. It could be rideshare. It could be shipping companies. There are so many things that we’ve used them that they’ve been so helpful for. You can probably hear in my voice. I tend to get a little bit protective of that because I’m sure if you asked our partners at SoftBank, do they have some things they’d like to do over. Yeah, probably, but that’s their answer to give. I can just tell you my experience has been really unbelievably collaborative.

Alejandro: Got it, and let me ask you this. If you were going to sleep tonight, Bill, and it’s an unbelievable snooze. You wake up in five years, and you wake up in a world where the vision of Cambridge Mobile Telematics is completely realized. What does that look like?

Bill Powers: I think one of the reasons that we started our company, and why SoftBank had an interest in us, and what our vision has always been was to somehow power the future of mobility. If you look at what’s happening today, two years ago, three years ago, or five years from now, I think you need to look at it very holistically as a continuum. More people are going to be transported in different ways. More people are going to be moving around themselves, or product, or services differently than they do now, whether it’s autonomous driving. We’re agnostic to the data source, so it could be a phone. It could be one of our IoT devices. It could be the information from the vehicle. Quite frankly, it could be something that we haven’t thought about yet in autonomous driving. The thing about autonomous driving is, those intelligent vehicles are perfectly capable of communicating and driving. The problem with autonomous driving is there are other human beings on the road, and human beings are flawed and unpredictable. So, we believe that our intelligence five years from now will be at the center of that future or reality of mobility.

Alejandro: Very interesting. Now, it’s been a remarkable journey with the business, and I’m sure there are always lessons. If you had the opportunity to go back in time and have a chat with your younger self, with that younger Bill that is thinking about launching a business, what would be that one piece of business advice that you would give to yourself before launching a business and why knowing what you know now?

Bill Powers: That’s a great question. I would say, “Don’t be as angry. Shut up and listen more.”

Alejandro: Got it. Wow. I love that. Bill, for the folks that are listening, what is the best way for them to reach out and say hi?

Bill Powers: They could email me. That sounds great. My email is [email protected] – Website:

Alejandro: Amazing. Well, Bill, thank you so much for being on the DealMakers show today.

Bill Powers: Thank you, Alejandro. It was great to meet you.


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