Neil Patel

I hope you enjoy reading this blog post.

If you want help with your fundraising or acquisition, just book a call click here.

Cherif Habib has been a lifelong entrepreneur. He started his first business at just 16, has taken startups full cycle, and has now raised $100M for his latest healthcare venture. His company, Dialogue, has just raised $100M from top-tier investors like HV Capital, White Star Capital, Walter Capital partners, and Sun Life Financial.

In this episode, you will learn:

  • How Dialogue got started
  • The challenges of fundraising, and mindset you need
  • Raising money in Montreal versus the US
  • Cherif’s top advice for other founders


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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The Ultimate Guide To Pitch Decks

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 Cherif Habib:

Cherif Habib is the Co-Founder and Chief Executive Officer (CEO) of Dialogue, Canada’s leading virtual care company. Launched in 2016 and having raised over $100M in venture funding, Dialogue offers its service to millions of individuals, and provides care to more patients every day than the largest emergency rooms in the country. Dialogue has received several industry accolades, including Deloitte’s Top 50 Companies-to-Watch award.

Before launching Dialogue, Cherif Habib was the CEO of EMcision, a medical device company sold to Boston Scientific, and spent three years at McKinsey as a senior management consultant.

Cherif Habib has an undergrad in Computer Science, a Master of Law and an MBA from Wharton with majors in Marketing and Operations.

Connect with Cherif Habib:


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Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. Today we have a founder that is executing, building, scaling, you name it, out of Canada, out of Montreal, and definitely doing great, great stuff. I think that we’re going to learn quite a bit, and I don’t want to make you wait any longer, so without further ado, Cherif Habib, welcome to the show.

Cherif Habib: Thank you, Alejandro. Thanks for having me.

Alejandro: Originally born in Cairo, and you spent some time there until your parents moved to Montreal when you were ten years old. How was life growing up for you?

Cherif Habib: Life was great. My parents had a great life in Egypt. They moved to Canada because they wanted to give me and my sister better life opportunities. Sometimes, people talk about winning the lottery by being born in a certain country. People often say, “I won the lottery because I was born in the U.S. or born in Canada.” What my parents basically did is that they changed the odds in our favor by moving to Canada, and I really appreciate that. I think that’s why it’s so powerful with immigration. They left behind a very comfortable life to go to something new for us. That was great.

Alejandro: Also, for you, you were already ten years old, you so were quite aware. You already friends that you had made, and it was quite a change for you, so how do you think that has shaped you and especially your personality? And even bigger than that, how do you deal with uncertainty because I’m sure that has taught you quite a bit now that you’re an entrepreneur?

Cherif Habib: Absolutely. Moving away from Egypt was, obviously, very hard on my parents. I think it was much harder for them than it was for my sister and me because, as kids, you adapt in an easier way. But it shaped me because I’m a very adaptable guy. I get along with people very easily. We’ll talk about this later, but I’ve moved several times since then, as an adult, to different places. I think I did a good job both keeping in touch with my old friends and also making new friends in new places. My first friend that I met on the first day of school at four years old is still someone that is very close to me today, and we’ve kept in touch throughout all these years. I’ve, obviously, made many new friends since then, and I would say that this is one of my strengths.

Alejandro: Also, for you, you had your grandparents, also entrepreneurs, so I’m sure you learned quite a bit from them and saw them operating their own business. What lessons did you take out of that?

Cherif Habib: Absolutely. My four grandparents were entrepreneurs, as you mentioned. On my dad’s side, my grandfather was a civil engineer and a real estate developer. My grandmother had a furniture or woodworking factory. They made furniture, but she also supplied many things for my grandfather’s building, so they were clients or suppliers of each other, which was interesting. And on my mother’s side, it is a bit of a similar story, where my grandfather was a grower. He had a farm, and he was growing flowers, fruits, and vegetables. My grandmother had a very successful flower business. So, again, kind of a vertically-integrated business. Growing up, my four grandparents always talked about work at the dinner table, and I grew up with that jargon. What’s really interesting is that all of them were very successful business owners without going to business school without access to venture capital or even traditional sources of financing like bank debt. All of that, 50 to 60 years ago, didn’t exist in Egypt. They all succeeded with a mix of extremely hard work, good judgment, and integrity, doing the right thing for their employees and for their customers. When you think about it, that’s really, basically, all you need to know to succeed in business. The rest is kind of micro-adjustment and optimization, but this is really the foundation of it all. I consider myself extremely lucky to have grown up in that environment with those role models. It was an amazing experience.

Alejandro: Talking about not having the education or just having the drive itself. Look at you – at 16 years old with your first business. Tell us about this.

Cherif Habib: Yeah. I was an accidental entrepreneur. At 16, I started a business with a very close friend of mine in high school. Essentially, for us, it was a very simple means of gaining financial independence from our parents. It was a very – this is how we got away from having to depend on an allowance from our parents to get nice things and go out. We were both tech nerds, and we started a small IT consultant business configuring networks and solving printers at a dentist’s office, making websites, stuff like that. We were earning way more money than anybody at our age, and we had an amazing time. That was another great formative experience. That’s when I decided that I wanted to be an entrepreneur for the rest of my career. Growing up, the dream was to become a doctor. At 15 or 16, when we started that business, I got hooked. From then on, I had no doubt how I was going to spend the rest of my career.

Alejandro: That’s amazing. In this case, you had that love for computers, and you ended up studying computer science. Do you remember how you started to develop this love for computers?

Cherif Habib: Yes. My dad was one of the first people in Egypt to own a personal computer before they were available for military or commercial uses, and very early-on he believed in it, and we had a computer at a very early age. He really cared about me learning to type and learning to use the computer, and I was hooked from a very young age.

Alejandro: So, then, let me ask you this, because you go to school and study computer science, and you kept at it by being an entrepreneur there. It was your second business, and this one, you would be juggling with college, but then also having crazy amounts of cash around you. So, tell us about this telecom business.

Cherif Habib: Yeah, that was a really interesting story. If you remember, back then, we’re talking about the year 2001. Today, everybody has an iPhone or an Android device. Back then, there were hundreds of different handsets that you could have. A friend of mine and I had seen a cool Ericsson phone. I remember it was a T28. That Ericsson phone was available in Europe, Singapore, etc. We had a friend who was going to Dubai over the holidays. We asked him to get us two of these phones. He got back, we had the phones, and we were the coolest kids in college. We then realized that they were sold on eBay for much more than we had bought them. So, it was a silly kind of business that started from there. We started importing phones from Asia, the Middle East, and Europe and selling them on eBay. Then, we started a wholesale business where we started selling them to cellphone stores across Canada. Then, we started selling them through network operators. So the business really grew very fast. We started from nothing. Again, no cash; no financing, and we grew it into a pretty big operation. Now, don’t forget that we’re full-time computer science students. We were three partners at the time, and we would put all of our classes in one day and run the business for the six other days of the week. It was really fun. We were working nonstop. Again, it was a really fantastic experience because we learned a lot from it. I remember one strange situation where we found a supplier for a model of Nokia phones in the States, and we found a buyer in Singapore for thousands of these phones. Each of these phones cost a few hundred bucks. This was a transaction for several hundred thousand. Of course, we didn’t have that money, so we flew down to the U.S. to that supplier, and we made sure that they had the stock. Then, we got the client in Singapore to wire the money, and we stayed there overnight. Of course, the guys in the U.S., when they took our passports to check our identity, they couldn’t believe that we were 19 years old doing transactions of that size. That big trade put us on the map, and we started trading pretty big quantities of handsets. Over time, we got into the accessories business, which actually turned out to be a better business than handsets. The accessories business had much bigger margins, and it was a very, very fragmented supply chain, so we were able to make a dent. I did this business for about five years with two of my partners, and after five years, they bought me out, so I sold my shares to my two partners because I wanted to go and do something else. That’s when I moved to Switzerland, and I joined McKinsey in their Geneva office.
Alejandro: Being an entrepreneur, being able to build your own dream, why did you decide to go and build the dream of someone else?

Cherif Habib: It’s a great question, and it’s because I wanted to do something even bigger. Back in the day, I had never heard of McKinsey, actually. I read in the newspaper – there was an article that was doing an analysis of the background of entrepreneurs. It said that many of them had gone to great schools, Ivy League Schools, and it showed the backgrounds of many successful entrepreneurs. I remember the article basically said, the number one place these people come from is McKinsey, #2 is Goldman Sachs, #3 is Bain, Morgan Stanley, etc. I had never heard of any of these things. I said, “I’m going to apply to each of these in order. I’m going to apply to McKinsey first, and if I don’t get it, I’ll apply to Goldman, and so on, and so forth.” I said, “Before I apply to McKinsey, let me send some questions to one of their offices so I can get my answers, and then when I understand what this is all about, I’ll apply to McKinsey in Montreal.” I picked Switzerland randomly, and I started emailing them all sorts of silly questions. After a while, they said, “You’re asking a lot of questions, so why don’t you, next Monday at 9:00 am, speak to the senior partner, and he’ll answer all your questions.” I said, “Great.” We had this conversation, and after the phone call, I got an email from their recruiters who said, “Congratulations. You passed the first phone interview. We’d like to invite you to a full day of interviews.” I took a plane, and I went to Zurich, and I did the typical eight interviews in one day. What’s really interesting with that is because I didn’t really know how big of a deal this was, and because I didn’t torture myself with the preparation – I bought a book that says how to prepare for a consulting interview. I read it on the plane and train ride. I think because I didn’t know, I was not intimidated because I had no idea what this whole McKinsey thing was about. That was another lucky break in my career.

Alejandro: It’s interesting how all these people that end up going to McKinsey or Bain or consulting-type of operations, they end up being very good at dissecting a problem and coming up with a solution. Like dissecting a big problem into multiple small problems and then tackling each one of those. So, what did you get from that?

Cherif Habib: Yeah. That is one of the very nice skills that we got is breaking something complicated down to more simple things. But I think, really, what I got the most out of that experience is the confidence in myself that I can learn a new industry or a new problem with a beginner’s mindset. And just by asking basic questions, understand the big forces in that industry. I remember, at some point, I was staffed on a project in Egypt, and it was for the Ministry of Transport, and it was for a huge project. Every weekend, I would go have dinner at my grandparents. My grandmother asked me a question. You know, grandmothers sometimes get to the core of something very fast. She said, “What the **** do you know about transportation, and how is a 24-year-old advising the Minister of Transport on a strategy? What do you know about it?” That was an amazing question because she was absolutely right. We were a bunch of kids advising the minister of transport on a strategy. Essentially, that experience taught me that I could learn any industry and any situation and understand the basic things, but it also made me realize that I actually didn’t know anything, and her question was totally fair: who am I to advise on strategy? So that was a nice dose of humility.

Alejandro: I hear you. Then, you go to Wharton, and Wharton is an amazing community that amazing entrepreneurs have come out of. This was a really nice segue to perhaps reshift or redirect your career, and I think this got you into the world of building and scaling and hypergrowth. And eventually, you end up in your uncle’s company. How did this happen? Tell us about it.

Cherif Habib: Maybe just a quick word on McKinsey and Wharton because I think it was a really important lesson for me. In that stage of my life, in my early 20s and my mid-20s, because I didn’t go to any fancy college or any of that, I was still in the mindset of attaching myself to “prestigious” brands. I was still in that mindset of having a chip on my shoulder and showing the world that I could do it – that I could work for McKinsey, that I could go to a top-rated Ivy League school despite my background and total lack of connections, etc. There was, unfortunately, this insecurity of attaching myself to a brand. Having said that, it was an amazing experience, and I’m really glad I did it. At Wharton – at that point, Wharton was shifting from being known exclusively as a finance school to being one of the good places where entrepreneurs come out. I went there as that shift was happening, and many amazing entrepreneurs came out of the school later on, which was great. In the few months between McKinsey and Wharton, I was unemployed, and I was helping my uncle, who is a world-renowned liver surgeon. He had a small company called EMcision. That company had a few patents coming out of his experience operating in liver surgery. I spent some time trying to organize the strategy thinking about how we make products out of his patents, what did the solutions look like, etc. During business school days, I stayed in touch with him and helping him informally. When I graduated, I decided to join forces with him full-time. I started as the COO of the company dealing with everything that was not medical or scientific. After about a year, the board and he made me CEO, and he was CMO, Chief Medical Officer. We had a really good partnership because we really trusted each other. He’s my uncle, and we have a really, really good relationship. We were very complementary. The division of labor was really clear. He was going to take care of the medicine and science, and I was going to take care of everything else, or “the business” side of it. That was a really successful partnership. I learned a lot from that. That’s what got me hooked to the business of healthcare. I got passionate about healthcare during my time at EMcision. I knew that I was going to spend most of if not all of my career in healthcare because I really loved it.

Alejandro: So, how was this journey with EMcision?

Cherif Habib: It was fantastic. We had very little means. We had only raised a little bit of money from friends and family and angels. No institutional investors. We had to deal with a lot of constraints. As you probably know, building a medical device company is a very capital-intensive journey, and we didn’t have capital. So, we did a lot with very little. We put out the products. We passed through the regulatory hurdles, whether it’s the FDA or Health Canada or in Europe. We sold our devices all over the world. The U.S., Germany, and China were our largest markets. We made a real dent. These were surgical devices that helped in the treatment of liver cancer and pancreatic cancer and cancer of the bile duct. We really made a dent by having a huge impact on these patients, increasing their lifespan and improving their quality of life. It was a very, very impactful and motivating business. But it was hard because we were competing with a company where the CEO’s salary was higher than our whole annual revenue of the whole company. In the medical device world, it takes a lot of money. It takes, usually, tens of millions to get to market and to be commercially viable, and we did it with an order of magnitude less. When the opportunity came to exit to Boston Scientific, we knew that was the right exit for us because it would allow us to take our products and multiply by 100 the salesforce and the commercial efforts, and therefore, get so many more patients to benefit from it. So we came to a deal with Boston Scientific. That was a really good outcome for us, personally, a really great outcome for all of the investors and shareholders. But, most importantly, it was a great outcome for the patients that needed this product because so many more now could benefit from it.

Alejandro: Obviously, this allowed you to see the full cycle of a business. Right?

Cherif Habib: Exactly.

Alejandro: All the way until the finish line, and I’m sure that gave you a lot of visibility and perspective, too. If you had to take one lesson from this experience, what would you say that was?

Cherif Habib: We had some really tough times building EMcision. We ran out of money several times. I remember, sometimes, passing the payroll on my personal credit card. So, these were really tough times. But I feel like when you’re working on something so impactful, it really makes those tough times much easier because now, you’re working for a cause, and you’re not just running a business. I think that if we weren’t in that field or doing something with such an important mission and knowing the patients that we were helping, it would have made it almost unbearable psychologically to go through the tough times.

Alejandro: Let’s shift gears here because, after EMcision, you started your baby, Dialogue. Let’s talk about Dialogue. How do you come up with this problem, and how did you go about addressing it with a solution that has become Dialogue today?

Cherif Habib: Yeah. There was actually a bit of an overlap between the two because the deal with Boston Scientific, at the beginning, fell through because of a regulatory issue, and it took us 15 or 16 months to fix it and consummate the deal. So there was a little bit of an overlap between the two businesses, but essentially, with EMcision, with my medical device company, I was traveling all over the world to sell our devices. I got an amazing education of how healthcare is delivered and structured and how the systems work in different countries. I was really inspired by the healthcare systems of Scandinavian countries in Switzerland, and I felt like we could take a lot of these best practices and bring them back to Canada. At the same time, I met the folks out of an incubator here in Montreal called Diagram. Diagram, at the time, was more of a fintech incubator, and they wanted to start a vertically integrated health insurance company, kind of like what Oscar was. I decided to join forces with an early team and to start that business. Very quickly, we realized just the telemedicine portion of that was really interesting. In the first few weeks or maybe months of running this, we thought that we would build a B2C company. The vision was anyone on their phone could see a doctor and not have to wait days or weeks to get an appointment with their primary care provider. Now, maybe just open a small parenthesis. People in the U.S. sometimes feel that the Canadian healthcare system is the nirvana, and if you listen to Bernie Sanders or others, they talk about the Canadian healthcare system as if it was the best thing in the world. Living here, we recognize there are a lot of great things about our system, but was also recognize that there are many shortcomings. Actually, many people think that the U.S. healthcare system is better. The reality is somewhere in-between. I think if you pick and choose some elements of both, you get to the right system. All this is to say that we started working on this idea of allowing you to see a doctor faster on your smartphone at any time. Within the first months are so, we quickly pivoted to a B2B play, which is what we’re operating now. So we basically figured out that Canadian employers, even if the healthcare system here is universal and free, Canadian employers were, in fact, paying a lot of money indirectly because their employees were missing work, and their employees were not as productive as they can be because it takes weeks to deal with an issue. So, we decided to build a B2B-focused telemedicine company, and we would sell subscriptions to businesses where they would pay us a small amount for employee-per-month to give all of their employees access to our service. This is the first couple of years of the business, this is how it was, and that value proposition resonated really well in the market, and we grew it into what become a very sizable business. In the last couple of years, essentially, what we realized is that employers deal with many suppliers in the health and wellness space, and there’s a fatigue with dealing with all these different point solutions, and that nobody had really succeeded in creating an integrated platform for these health and wellness services. So, Dialogue has evolved, in the beginning – we started with this idea of building a vertically integrated health insurance company, and then we decided to focus on telemedicine. We thought it was going to be B2C. Rapidly, we pivoted into B2B. We saw a lot of traction there. That was clearly the product/market fit. We see ourselves not just as a pure-play telemedicine company, but as an integrated health platform that included telemedicine for primary care, but also for mental health, for employee assisted programs. And we’re going to continue building spokes in the hub. It’s really interesting how the idea has evolved over time with market feedback.

Alejandro: For the folks that are listening, what ended up being the business model? How do you guys make money in Dialogue?

Cherif Habib: We make money by charging businesses a monthly recurring fee. It’s a per employee per month fee. And depending on how many services you sign up for, it could be $6, $7, $8 per employee per month if you’re a primary care-only client. It could double if you subscribe to our other services. Today, we have about 25,000 different businesses that are clients of ours. A thousand of them, we acquired directly, and the rest, 24,000, we acquired by working with distribution partners such as insurance carriers, benefits consultants, etc.

Alejandro: Cherif, what I want to ask you, too, is, for a business like this, obviously, it requires capital. So how much capital have you guys raised to date?

Cherif Habib: We have raised just over 100 million dollars.

Alejandro: Got it. The tech scene, the hypergrowth company scene is booming in Montreal. What do you think has triggered that?

Cherif Habib: Montreal is an incredible place to start a tech company. We have one of the highest concentrations of universities and students per capita in the world. We have many great technical universities here. The cost of living is quite cheap. Our quality of life is amazing, and the government has put in place several incentives for R&D and technical work. So all of these reasons together have created a very vibrant scene, and I would say that in the last ten years, this scene has exploded. I graduated from Wharton in 2011. Going into Wharton, I thought that I would move to Silicon Valley afterward. That was kind of my dream. I saw what was going on back home and how the tech scene was starting here in Montreal. I decided to come back home – some, for personal reasons being with friends and family, but some because I saw this emergence of a scene. I think that Montreal is probably one of the best places in the world to build a tech company.

Alejandro: Let me ask you this because I know that going back to what you were saying on the fundraising. For you guys, it has not been a thing of roses and beautiful. Obviously, at some points, it has been cloudy, specifically on your Series B. What happened?

Cherif Habib: I don’t know the exact percentage, but I think that the vast majority of venture capital in the world is concentrated in the U.S. We had a very hard time raising from American investors because invariably, the feedback we received was, “Your growth is unbelievable. Your metrics are fantastic. You really topped this. We rarely see those numbers. But we just don’t understand the Canadian healthcare system enough to make an investment there. It was always kind of a different version of “This is outside of our circle of competence, or we don’t understand this well enough. So when you exclude the biggest source of capital in the world from your fundraising process, it, of course, makes it much more difficult. There are now many great investors in Canada, and it’s easier to raise money here, but it’s still a much more limited environment than in the U.S. or even Europe. So our universe of potential investors was limited, and our Series B took a little bit longer than we would have liked it to take. We were getting dangerously close or closer than I would like from running out of money, so it was a pretty stressful time. But the nice thing is that we ended up raising money from the investor that we had put as our number one. It was our dream investor for his business at CDPQ. It’s the pension fund of our province. We wanted to partner with them because they have a very long-term orientation. This is really patient capital. Because we were building something in the healthcare field, we felt that having an investor that also had this pension fund, or public orientation would help us. Again, it was difficult, but at the end, we ended up closing with our number one favorite investor. So it worked out really well, but I would tell you that for a few weeks, I was sweating really hard.

Alejandro: I’m sure that there are a lot of people right now that are listening, that are also maybe sweating really hard right now because, obviously, COVID has really complicated a lot: the opportunity to interface with investors, the opportunity – people literally have to work harder, even though, if you take a look at data, it seems that it has been booming – the total number of financings. But when you’re at that point, and you’re sweating hard, as you said, and you’re starting to hear those voices of what-if, what-if that, what kind of piece of advice would you have for the folks that are listening? How can they go about quieting those voices?

Cherif Habib: Alejandro, that’s a really, really good question. I think the founder or the CEO psychology is so important, and I think that I’m probably not the only one who hasn’t taken care of it over time. I think we work so hard, and we’re so into the action that we don’t take care of our own psychology, and I would say that this is really important. Then when you look at so many now iconic and successful companies and you read their origin stories, you’ll see how much they struggle to raise money. Look at Peloton. Peloton is now a breakout success. You read about their first couple of years, and they couldn’t raise money from anybody. Everybody thought, “The hardware is impossible. The margins were not good enough. There’s no mold, etc.” You read about companies like Cisco, how many noes they got before they got a yes, and it was one of the best investments ever. You realize that you just have to set yourself up that you’re not going to get a yes in the first 10, 20, 30 meetings, and that you may have to do 100 meetings to get a term sheet. If you go in with that mindset, and if you end up performing better, hey, fantastic! But, at least, you’re going in with that expectation that it’s going to be hard, that it’s going to be long, and you’re going to get a lot of noes. The other thing that I would mention is that during this time, when I was raising the Series B, I was going to the gym every morning, and I was listening to an audiobook. It was the Nike founder’s book, Shoe Dog. I was listening to it in the morning. Nike is, obviously, in a very different industry, a very different time. There was no venture capital involved, but Nike, in their first 10 or 15 years, was so close to the brink of disaster or bankruptcy or worse. It makes you realize that even if I was in a different era raising money for a health tech company, that the experience was actually very similar. I think that every entrepreneur, every business goes through these difficult valleys, and you just have to keep the faith; you have to believe in yourself and your team. If you have something good, then eventually it works out.

Alejandro: Absolutely. Cherif, for the folks that are listening to get an understanding of the size of Dialogue today, anything that you can share on numbers of employees or anything?

Cherif Habib: Yes. We employ about 800 people. Six hundred of them are healthcare providers, and 200 of them are in our other functions. I remember when I started the company, one of our investors said that the best companies in the world triple, double-double, or the other way around. I don’t remember. I remember saying, “This guy’s nuts.” Essentially, we ended up doing better than that, which looking back at it, it’s hard to believe, but it’s really amazing.

Alejandro: One of the questions that I typically ask guests that come on the show, and I think it will be very appropriate here to ask you, is if you had the opportunity to go back in time and go back to that point, perhaps even before starting Dialogue, maybe your younger self in 2016, and you were able to give yourself one piece of business advice before launching a business, what would that be and why knowing what you know now?

Cherif Habib: I would say, probably that one piece of advice is to trust my instincts more. Almost every single time where I made a decision that didn’t listen to that inner voice or that gut feeling, over time, it ended up being the wrong one. Even if I made the decision with what I thought was the right data or trying to be logical about it, or trying to apply things I learned in business school, at the end of the day, I learned that my instincts and my gut are often right, and if I don’t listen to that little voice, and I make decisions based on other things, I often regret it. So, I would say, listen to my instincts more.

Alejandro: Very profound, Cherif. For the folks that are listening, what is the best way for them to reach out and say hi?

Cherif Habib: I am on Twitter. I don’t have many followers, but I’m getting used to the medium. I really enjoy it. So, I am @cherif or you can email me [email protected] – I always love hearing from folks.

Alejandro: Amazing, Cherif. Thank you so much for being on the DealMakers show today.

Cherif Habib: Thanks for having me, Alejandro. Have a great day.

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