98point6 CEO & Co-Founder: Robbie Cape


Robbie was born & raised in Montreal, Canada and had an early fascination with the idea of being an open-heart surgeon.  His interests would then shift to computer programming after receiving a gift from "Uncle Ronnie." Robbie's father ran a family business, and throughout Robbie's childhood, he would listen to his father openly discuss business ordeals and ideas at the dinner table. Robbie would go on to attend Princeton University and get a degree in engineering & management systems before beginning his career at Microsoft. He would work for Microsoft for 12 years and in the podcast, he discusses his biggest career failure that resulted in humiliation followed by a strong bounce-back. After a 12-year-run with Microsoft, Robbie decided to make the leap and start his own business, something he always dreamed of doing. The sense of urgency was sprouted from the sickness and death of an old friend that he discusses in the podcast as well; A truly emotionally intense time for him. After starting Cozi Group, Inc. and selling it, he went on to start 98point6; a technology company that facilitates on-demand primary care through an application on a mobile phone. It's sort of like the "Uber" of doctors, so if you need a doctor, you just open the app! Today, 98point6 has raised almost $90M and is revolutionizing the way primary care is handled.

Podcast Transcript

Note:  There may be errors to this transcript (some funny, some confusing - we used an automated transcription software!)

00:00:00 Robbie Cape: David Cole called me into his office and basically fired me from the position. I crashed and burned in this position as publicly as anyone can crash and burn.


00:00:21 Ash Faraj: Hey! Welcome to the ExecuTalks Podcast. It’s the show that gives you insight to the personal stories of today’s top executives.  In this episode, you will hear from Robbie Cape, current CEO and Co-founder of 98point6, a technology company that facilitates on-demand primary care through your phone. It’s like the ‘Uber’ of doctors, so if you need a doctor you just open up your app. 98point6 has raised almost $90 million and is truly shaking up the way primary care is done. You want to stick around until the end to hear about Robbie’s big failure that he shared only on this podcast.


00:01:03 Ash Faraj: Hey guys, so real quick, we originally ran this episode last year. If you haven’t listened to it yet, this is one of my favorite because Robbie dives deep into one of his biggest failures during his time at Microsoft. He dives deep into the stories of what shaped him as a child. He shares a defining moment in his life when a friend of his got sick with cancer and passed away. It would ultimately change his life and his direction forever.


00:01:41 Ash Faraj: If you think back to when you were five, six, seven years old, do you remember what you wanted to be when you grew up? I remember for me, I really wanted to be an engineer at that age. For Robbie it was one experience that made him believe that he wanted to be an open heart surgeon for the rest of his life. Then, when he was 13, Robbie’s uncle gave him a gift that would shift his interest into computer programming.

00:02:10 Robbie Cape: There were three experiences that I had as a child that had a phenomenal impact on me. The first was -- actually you won’t remember this because you’re too young. But in the late seventies, it must have been in 1977, ‘78, ’79 -- I watched an episode of That’s Incredible.” I literally still remember. I have a picture in my mind of watching the episode where they showed open heart surgery on That’s Incredible. They would do all these vignettes of these things that were incredible on That’s Incredible; it was an hour-long show. I saw this episode where they showed open heart surgery, and I was amazed. I decided I wanted to be an open heart surgeon.

00:03:05 Male Voice 1: How old were you at the time?

00:03:06 Robbie Cape: I was seven, eight, nine. So the next five years after that, when anyone would ask me -- can you imagine as a 10-year old someone would ask me -- “What do you want to be when you grow up?” I’d be like, “I want to be an open heart surgeon.” It was like the first time I really associated with a profession. That first association was certainly in the medical space. The next experience that I had was for my bar mitzvah.

00:03:39 Ash Faraj: So, 13?

00:03:40 Robbie Cape: Yeah, 13, exactly. For my bar mitzvah, and I still remember him showing up. Uncle Ronnie showed up at this dinner club in Montreal the Friday night before my bar mitzvah on Saturday morning with a Commodore VIC-20.

00:03:55 Ash Faraj: What is that?

00:03:56 Robbie Cape: This is an early-day personal computer. It was one of the first personal computers that people started to learn to program in Basic on. I got this computer for my bar mitzvah and was incredibly excited about that. The week after the bar mitzvah, I found someone to teach me how to program, and I learned how to program a computer in Basic. That was certainly, clearly, by virtue of where my life would eventually go, clearly that was a pivotal moment. Getting that Commodore VIC-20. Getting excited about computers. Learning how to program and just starting to understand the depth, the potential, that existed in what computers could do. The third event, which is sort of not really a single event but more of an arc, is really the entrepreneurialism in my family which also had a very dramatic effect on my eventual sort of transition from wanting to be a doctor to deciding that what I really wanted to do is build businesses. My father was obviously a critical role model in my life. He was running our family business. My uncle left Montreal, and he left my father with this family business that at the time was this really small family business. My father --

00:05:44 Ash Faraj: -- What kind of business was that?

00:05:45 Robbie Cape: It was a skin care and cosmetics business. My father built this business and it was a medium-size business. My father didn’t have any investors and he didn’t have a Board. Yeah, he had executives who were around him, but he was really running the show. It was a family business that grew significantly, but it was really my father’s business. He didn’t have any peers at work. It wasn’t like here where I have this executive team and we’re building this company together and they help. We all do everything together as a team. Like this was my father’s company, right? But everyone needs a community. Everyone needs someone who they can bounce stuff off of, right? Everyone needs partners. My father… our dinner table was sort of like his boardroom. He would bring issues home. I remember -- now I know they’re HR issues -- but he’d bring home challenges he was having with people at the company. Decisions he had to make. I remember there were companies that would approach him to try to purchase the business. We would talk about that at the dinner table. Usually, you have those kinds of conversations in a boardroom. If you really look at my excitement with building a business, and a lot of the core values that I’ve developed around building a business, you really have to -- if we could go back and unravel all of those conversations that happened at those dinner tables -- I’m sure it all goes back to there. It was just ingrained in me and it wasn’t like my father and mother weren’t… It wasn’t active. It wasn’t like they were trying to ingrain business in me, it was just natural. It was organic. It was just happening. The business was incredibly interesting. My father had several hundred employees. He had a union that he was dealing with. I remember all those challenges; negotiating with the union, and the strike, and the lockout, and having to decide, “Do we allow them to strike? What do we do?” It was all just part of my childhood. I think that, probably as I made my way through high school, I started to get really excited about going to work. Because that’s another thing -- by virtue of my father’s work being something he loved -- he only ever went to work because he loved it, period. Why didn’t he sell the business? He could have made all this money. You think, oh, money solves everything. Money makes the world go round. No, no! Great work and connections with people who you’re working with, and the impact that you’re having on their lives and on your life, that is what has impact. My father turned down all those offers. Why? Because his line to me was always, “What will I do tomorrow?” That was his passion.

00:09:09 Ash Faraj: I’ve been hearing this a lot lately. I’m not sure that it is accurate. People have been saying that being successful doesn’t necessarily correlate with attending a good school. And the numbers don’t lie. Attending a good school with a great network can actually propel your career to the top and help you in many ways as it did for Robbie. He attended Princeton University and got his degree in Engineering and Management Systems before going on to work for Microsoft. Robbie would stay at Microsoft for twelve years. During his time there, he shares getting the best promotion in his life only to find out two months later that he was fired from that position.

00:09:51 Robbie Cape: It was eight years in. I had worked for two years on Visual Basic and then I worked for six years on Microsoft Money. Things were going really well. I was sort of finishing up on my Microsoft Money time. I’d been on Microsoft Money for six years and that was a lot of fun and great learning. Had amazing people. I needed to figure out what I was going to do next at Microsoft. This truly phenomenal opportunity -- I actually just had a walk a couple of days ago with the leader of Microsoft. His name is Bob Muglia who I had met with as I was thinking about this career move, this next move -- and Bob sort of recruited me into this role on his team. It was this incredibly strategic… Like it was one of the most new, strategic, sort of under the microscope, bright lights shining on it, center strategy, Microsoft effort. This was the big leagues. The project was called HailStorm. This position became available, and they were talking to me about the position which in and of itself was kind of crazy. I remember -- and this is nuts on April 1st and this must have been 2011 -- on April 1, 2011, David Cole let me know that I’d got the position to be the general manager of HailStorm. I was going to build this team called HailStorm that is literally the most important project for the next five years for all of Microsoft, based on what they were telling me in terms of how it was to Steve and to Bill. This was like the big leagues. I’d really been sort of growing up through Microsoft Money. It was kind of like… I was in the farm leagues and I just got this position in the big leagues. I still remember when I learned that David was going to offer me the position, and you could say it was the highest day, like most exciting day, of my career. Two months later, two almost to the day, a day before -- so the whole time I had planned to take my one-month paternity leave for the birth of our second son in the month of July. The night before, the Friday afternoon at 5:00 o’clock the night before -- I was going to be leaving for a month, David Cole called me into his office and basically fired me from the position. Like I crashed and burned in this position as publicly as anyone can crash and burn. Now remember, this was under the microscope, everyone was watching, like everyone cared about this, like hundreds and hundreds, thousands of people, and I basically crashed and burned in the position.

00:13:40 Ash Faraj: Wow, how did you feel at that time?

00:13:44 Robbie Cape: That Friday afternoon, I still remember sitting in my… Noah wouldn’t remember. Noah was less than one years old, but Benjamin was three. Benjamin asked me what had happened. I remember. I think it is the last and maybe the only time that I’ve cried in front of Benjamin. This is like 15 years ago now, right? I remember telling him that I got taken out of this position in full sight view. It’d be one thing if I’d failed off in a corner somewhere. Like that’s one thing. But I literally I had to send an email to hundreds and hundreds and hundreds of people from France. Remember, I was gone. Basically, letting everyone know that I was no longer in this position. It was horrible. It was horrible.

00:14:47 Ash Faraj: At the time it happened did you feel that your career was finished? Were the negative emotions overwhelming enough to make you feel like, oh, my God, I’m done, or did you see a positive light?

00:15:05 Robbie Cape: At that exact moment, no. I think I was shell-shocked. All I felt was, oh my God, how can this be happening? I did not even think about getting up. All I could thing about is that I basically had done a face-plant smack. It is absolutely true that what doesn’t kill you, what almost kills you, will make you stronger. And it is absolutely true that I learned more. That experience was so traumatic and so negative. It left me severely scarred. There’s no getting around that. You learn. Like scar tissue is what you need. You need it because you can look down and you see it, you feel it, and so it’s a reminder.


00:16:24 Ash Faraj: When was the last time you thought about death? Not to be negative, but I’m sure you know someone, or you may have even gone through this.  I’m sure you’re aware of just how much of an impact the passing of a friend or a family member can have on someone. For Robbie there was a close friend of his that got cancer and would eventually pass away. This would be an ignition to Robbie’s flame that would cause him to rethink everything and change his life direction completely.

00:16:59 Robbie Cape: The childhood friend who passed away her name is Orit. I met her when I was 15 in Israel. I was visiting a kibbutz and met her there. We became good friends. We lost touch. Literally, when I was 15. It was a long, long time ago. We lost touch. We stayed in very close touch for several years. Then we made contact again just before I was supposed to travel to Israel with my family. It was around that time when I learned that Orit was sick. Orit got cancer. She told me since we were in touch because we were going to visit Israel. I got back in touch with her. We were going to meet up with her and whatever. A few months after that, after we got in touch, she told me she was sick with cancer. And I went to see her. I decided that this is a very dear old friend, it’s my first old friend who’s gotten sick with cancer. I’m just going to get on a plane and I’m going to go see her. And I did. It was really as she got more and more sick, I recognized that she was likely going to pass away which she ultimately did. That was really when -- so it was very kind of gradual, over the course of about twelve months -- It was then that I realized how fragile life was. And the realization actually, interestingly, it wasn’t so much that I was thinking that I needed to move on from Microsoft. The realization was, oh, my God, I need to go do what I want to be doing for the rest of my life. Like tomorrow! I could find out tomorrow that I have cancer. You know, God forbid. I could have a year left to live, right? I would then look back and say that there was this thing that I wanted to do for the past twelve years, or even longer for the past twenty years, that I had just been planning to do but I had never done? That’s kind of crazy, right? You should do today what you want to be doing for the rest of your life. It was really that recognition that -- you know, a lot of people as they get a little older, they recognize -- life is short. When you’re young, you don’t think life is short.  You think you have unlimited time, right? As you get older and things start happening; like good friends get sick, good friends die, maybe you lose a sibling. My wife lost her sister a couple of years ago. These are all things that begin to happen to you as you grow older. It just reminds you that you have a limited amount of time on this earth, productive, and you should make the most of it.


00:20:34 Ash Faraj: You may, or may not, have had an experience like Robbie did. But the chances are you probably had a life experience that made you question your life direction. When extremely intense, emotional experiences like this happen to us, they are meant to make our passions more clear to us. For Robbie it was very clear that his passion was building businesses because he felt this extreme sense of urgency. Also, if you’re someone that wants to build a business, Robbie shares the dramatic difference of working as a leader within an organization versus starting a business. It’s a big difference and it would be a mistake to assume that they are the same.

00:21:18 Robbie Cape: I made the decision during that year that I really needed to go do what I wanted to be doing for the rest of my life. I was very planful about it. Okay, I’m in this job now. What I’m going to do, I’m going to sort of finish up this job that I’m in. It was the job that I took after HailStorm. I’m going to finish up this job that I was in. It was actually on the sales team. Like I’ve said, I was going to move into the sales organization. I went and did that for 1½ to 2 years and it was during that time that I decided I was going to do a start-up. But I was like, okay, maybe I should do a start-up within Microsoft first. This would be good learning. It’ll be my last job. I’m making the decision. I’m going to start a new group or a new effort at the company. I’m going to learn some of the skills necessary to do that and really proof to myself that I know what I need to know to build something from nothing because I’d never done that at Microsoft before. I thought I was learning all this stuff. But the truth of the matter is that, now looking back on it when I left to co-found Cozi with Jan Miksovsky, the gentleman who I’d met during my time on Microsoft Money, I thought I knew what it took to build a business. But I had no idea. I probably knew about 30%, maybe 20%. Maybe I had learned 2% or 3% of that in that last two years. But the truth is I knew almost nothing. And the thing is you never know what you don’t know. That’s kind of what it is. I went and co-founded Cozi thinking that with the stuff that was flowing in my blood from growing up around entrepreneurs along with the experience I’d developed at Microsoft that I had what it took to build a business, and I had no clue. I had no clue. Thankfully, we succeeded across a variety of different dimensions at Cozi, and we failed along many as well. I also have lots of scar tissue. None of it is as big and prominent. It’s more like a thousand cuts of scar tissue versus the big, huge gash that I have from HailStorm. But I learned in aggregates. Certainly, in the nine years at Cozi I learned dramatically more than what I learned even in my twelve years at Microsoft, including the HailStorm experience of it. There’s nothing more powerful. Doing it, and stumbling, and getting up, and stumbling, and getting up, and doing it, and doing it, and doing it; that’s how you learn and grow. Like an athlete who goes out and trains. They can’t do it the first time and they try again. That was like nine years at Cozi, just training. It was like training and building the muscle and making the mistakes. We made carloads of mistakes. We had a few successes that were meaningful.

00:24:47 Male Voice 1: We want to switch gears just a little bit here. We want to play a quick game of “Finish the Sentence.” In my opinion, what is the most important life skill…?

00:25:00 Robbie Cape: Collaboration.

00:25:01 Male Voice 1: I’m 24 years old and I’m struggling to find my purpose. I should…?

00:25:05 Robbie Cape: Follow my passion.

00:25:06 Male Voice 1: Being an entrepreneur means…?

00:25:09 Robbie Cape: Willing to fail. Being willing to fail.

00:25:13 Male Voice 1: If I were to meet the 24-year old Robbie, I would advise him to…?

00:25:18 Robbie Cape: Listen more, talk less.

00:25:20 Male Voice 1: I’m stranded on an island and have access to one meal. My meal of choice is…?

00:25:26 Robbie Cape: Buffalo chicken wings. [laughter]


00:25:33 Ash Faraj: Thank you for tuning into this episode. If you enjoyed listening, please subscribe on Spotify or Apple Podcasts. Please leave a review so we that we can better serve you. Take care, dream big, and we’ll see you next Monday.

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