Neil Patel

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Ankit Gupta is a repeat entrepreneur who has not only built and scaled startups but who has been through the full cycle to an exit too. His latest venture, Bicycle Health, has acquired funding from top-tier investors like Questa Capital Management, City Light Capital, Frist Cressey Ventures, and InterAlpen Partners.

In this episode, you will learn:

  • Strategically picking your investors at each fundraising round
  • Why bigger companies acquire startups
  • The vision of Bicycle Health
  • COVID’s silver lining for this startup


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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 Ankit Gupta:

Ankit Gupta is the principal product manager for connected enterprise at LinkedIn, a professional networking site that allows its members to create business connections, search for jobs, and find potential clients. Previously, he served the same company as a senior product manager for Pulse.

Prior to LinkedIn, Gupta co-founded Polls. He holds a bachelor’s degree in computer science from the Indian Institute of Technology Bombay and a master’s degree in computer science from Stanford University.

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Connect with Ankit Gupta:

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty hello everyone and welcome to the deal maker show. So today. We have a repeated founder so someone that has done the full cycle you know and now he is on his next baby a rocket ship so we’re gonna be talking about building scaling financing and of course exiting as well. So without further ado. Let’s welcome our guests today and Keith Gupta welcome to the show.

Ankit Gupta: Um, thanks a lot Alejandro ah, glad to be here.

Alejandro Cremades: So originally born in India ah you know obviously now you’re you’re in the us you’re making a killing here. You know as an entrepreneur but originally born in India so so give us a little of ah walkthrough memory lane. How was life growing up in India i.

Ankit Gupta: Well, ah you know I was born in a town called aj mayor in the state of rajaskan ah I don’t remember much ah from from early childhood because I lived most of my childhood in Mumbai ah, and you know. Ah, my mom worked at a ah nuclear energy company ah in India and so you know we lived in this community with scientists and engineers pretty much everyone was working in the nuclear energy industry. Ah so. I remember growing up ah with obviously a really tightknit community of ah friends and and ah you know my mom’s mom’s friends but also a lot of competition. You know everyone was ah the kid of a scientist kid of an engineer. Everyone wanted to succeed. People used to look across the window and see you know if someone’s still studying at 2 am in the morning and and then you know try to do that the next day ah say yeah, it was you know it. It was a it was a pretty ah unique, ah community to grow up in India.

Alejandro Cremades: Now in your case, you ended up studying computer science. So why out of all things computer science.

Ankit Gupta: I was quite lucky to have the ability to pick what I want to study ah think very few people get that opportunity in India ah I wanted to go to I bombay. And I was really interested in ah physics I was really interested in math. Ah and and so when I was trying to decide sort of what to work on I ended up. Ah you know, just roaming around the campus and and talking to people and and ah knocking on professors doors and. Understanding kind of what what different areas are about and I remember going into this one professor she she was a computer science professor and I asked her sort of what is it mean? do but you know be be be doing computer science and and she basically told me on it if you like math if you like probability. Ah you know if you like. Ah, ah, thinking in in terms of frameworks algorithms ah I think you’ll really enjoy computer science. Um, and I was already biased towards computer science. My dad is ah again, a serial entrepreneur. He ah, one of his companies was actually a coaching center. Ah, for ah learning how to code so she you know he was um, you know, educating running classes on on Java and visual basic and Javascript and Html and I was a kid and I ended up taking ah a bunch of those classes and. Spent a bunch of my time around computers. Um, and so I thought well I already like computers I already know some programming languages I like math you know probably will will like computer science and thankfully that decision has ah has been a great one.

Alejandro Cremades: So in your case you landed in Stanford. So I mean I’d say I’m sure that your your parents were very proud because I know that in India.

Ankit Gupta: Um, yes I did my master’s.

Alejandro Cremades: You know there is a lot of pressure you know in the culture towards you know getting the best degree from the best University you can in the world. So I’m sure you made your parents very proud.

Ankit Gupta: Um.

Ankit Gupta: Um, I think so ah, you know I I think my parents were also quite relieved that. Ah, you know I’m I’m ah I’m going to a good place. Ah I think they were a little sad that. You know I’m I’m on the other side of the continent. Ah, but no, they they have always been supportive. Ah you know my mom’s always wanted me to ah to be the best at what I do and and always push me towards entrepreneurship and that’s what. Truly attracted me to Stanford you know hearing stories about Google about ah Apple who had Packard you know Silicon Valley hearing you know Facebook ah and and and the culture that can actually allow you to take an idea into into into reality. Um. Constantly you know I think I think I wanted to do that and and my mom and my dad completely supported that that sort of ambition.

Alejandro Cremades: Did you always knew that you wanted to be an entrepreneur.

Ankit Gupta: Um, feel like I didn’t have a choice. Ah my dad has been an entrepreneur ever since I I have known him and and you know my mom’s been ah, ah, kind of has promoted that too like. Remember in college I ah would talk about business ideas. Ah you know, ah, there was an entrepreneurship sell at Iot Bombay which I was a part of um, you know I was working on I remember the fourth year. So the last year of our undergrad Google came to campus. And basically told us you know we’re looking for um, ah, there’s a competition and they’re looking for sort of product companies to come out of the competition and and they would give a massive price for for sort of the team that won the competition and I was the one that really, ah, you know? ah. Convinced my friends to sort of team up and we created this idea to ah create a service called pos which is kind of like survey monkey like creating polls online or or type form back then and and we we you know, ah apply it and we won the competition. So I feel like it’s always been in my my Dna I think. Like our dinner table conversations at home. We’re around you know, financing and and cash flow and problems with employees and and stuff like that. So I feel like I’ve always been around it that that’s just become how I think ah to to. Ah. Ah, it’s been challenging like if I go to a water park or something or if I go on a hike you know I I start thinking about the business model behind these these activities and it really pisses my wife up. Ah, but yeah, that’s.

Alejandro Cremades: Are. Now now in in your case, you know none company None success. So a polls news so you started a company coming out of Stanford and you know tell us about it because I mean the outcome was unbelievable. So so tell us about it.

Ankit Gupta: Um, thank you? Yeah, ah, it was a fortunate accident. Ah my my friend and I we took a course at the design school at Stanford called Launchpad um, it was pretty unique. Entrepreneurship course. Um. Run by None amazing ah faculty members per leban and and Michael Dering um you know we had to create ready to launch a company in five weeks made it profitable in the next five weeks and so it fast paced. Ah and we basically picked this idea to create an app to read news on the go. Um, because this was in 2010 the ipad had just come out and we were the first ones standing in line the Apple store in polo although we got the ipad we opened it. We played around with it and we realized that this is an amazing consumption device. Ah, and and so we absolutely need a fantastic news readinging experience. Um and they started coding from from the first day. Ah and and so we launched pulse on the app store. Ah it wasn’t great. It crashed a lot. Um, but but there was something there and we didn’t have an office. So we would literally sit in ah this cafe in Palo Alto and I would be writing code and my cofounder would be taking the app and showing it to people and getting feedback from them and bringing that feedback back to me and then we would change it and we would do it multiple times a day constantly till we got it right. And ah I think we just got quite lucky where the app started resonating with people and you know even though the app was a paid app. We had None downloads in the first six months of the app like we literally raise our angel round just by selling the app. Ah. And then and then we raised funding and then we we grew the app and and eventually we got to all platforms. You know, internationally we got to about none downloads of the app and and and was eventually acquired by Linkedin.

Alejandro Cremades: Now Let’s talk about this because did you guys raise how much money did you raise for Polls news.

Ankit Gupta: Um, ah he raised. Ah we think something like 20000000 or so maybe maybe lesser actually maybe around None to 15,000,000

Alejandro Cremades: So 10 to 50000000 and obviously I mean you raise the money you guys are you know making making a killing and at what point does Linkedin come knocking.

Ankit Gupta: Um, ah I remember we were in the process of raising our series b um and we were talking to a bunch of investors. Ah, one of my mentors was the head of product at Linkedin. At that time. Ah, and so I think we just are reconnected. You know we we were having a conversation and um, we didn’t know but Linkedin was actively working on building a news team and investing heavily in news at that time. Ah. So you know I think just organically we ended up having a conversation with with the corp dev team and with the head of product for the news division. Ah, and turns out the synergies are massive. You know, ah what we were doing around creating. A news experience for power users people who are commuting people people who want industry news at their fingertips. That’s exactly what Linkedin was trying to build and so I think the question in our mind was hey do we want to? I mean we had had acquisition multiple acquisition offers along the way. We had. We had never accepted them because we always wanted to build a company further to further our mission. Um here. We had an opportunity where you know through Linkedin we could still achieve our mission but we don’t have to worry about revenue we don’t have to worry about building a sales team. Making this business a profitable business like all of those things which I love now but ten years ago I really wanted to build build the product I want to build the best user experience. Um, and and that was the opportunity Linkedin gave us. So um, yeah, we you know we we decided to go with it. But. But I think acquisition offers come constantly ah because you know you’re either ah a competitor to an existing incumbent um or or you’re disrupting your your drawing so quickly that you could add a new line of business to to. A company. So um, you know it’s always a tradeoff between whether you want to raise more funding and and go at it by yourself or or whether you want to get acquired. Um I think I think the ultimate ah sort of notstar is how are you going to achieve the mission. That you set out to achieve.

Alejandro Cremades: And how how long did it take the process from beginning to end with Linkedin.

Ankit Gupta: Um, oh my god ah it was crazy fast. We yeah so we had the None meeting with cor dev on on like a Thursday we met the head of product on Friday ah I remember my cofounder and I had.

Alejandro Cremades: So really.

Ankit Gupta: Separate hiking camping trips plan that we can in in in the bay area I was in bigxar he was in Monterey he had more self service than me. Ah, somehow he called he got a hold of me and we drove up. All the way from Andre and had a meeting with Jeff Wiener the Ceo of Linkedin at that time on a Sunday morning. We both drove back to Montre ah Monday morning we had a term sheet and Tuesday we signed the term sheet. Yeah, it was insane.

Alejandro Cremades: My God So that’s like no time.

Ankit Gupta: I mean it just it was just the perfect match and it’s worked out.

Alejandro Cremades: Wow. So I mean you you you sign you sign this thing. The deal gets done $90,000,000 I mean that’s a lot of None

Ankit Gupta: Um, that is I mean that was diligence after the deal so that wasn’t you know money wired the bank after four days but but you know we we pop we pass the diligence we type the knot and yeah here we are.

Alejandro Cremades: Yeah.

Alejandro Cremades: I Mean that’s from Bo you I mean and anything that you do that You did to splurge you know a little bit or know.

Ankit Gupta: Um I did I did I was really nervous about this but I actually bought a red convertible Audi as 5 Yeah yeah, the best for spending a lot of money for yeah, very quickly. Yeah, yeah.

Alejandro Cremades: I love it. Wow! Well the german cars are the best. So good choice. Ah yeah, and okaydding no kidding. So so then so then obviously in this case, you know like you joined you ended up joining Linkedin and you were with Linkedin for about 3 years

Ankit Gupta: Um, meeting.

Alejandro Cremades: And then Linkedin gets acquired by Microsoft and you know that kind of like gives you some perspective what happened after.

Ankit Gupta: Um, yeah yeah I mean I think Linkedin when I joined ah you know was a much smaller company than when I left I left right around when the Microsoft acquisition happened. Um. And you know I’ve always enjoyed building products and services that people love to use. Um and and I feel like I wanted to keep doing more of that whereas at a bigger company. A lot of it ends up being sort of. Management and and rising the corporate hierarchy which is a completely different skill set which I totally suck at so ah I didn’t want to keep doing that and I actually wanted to work on something. That’s hopefully much bigger much more impactful at least personally much more meaningful to me. And and something that again I can take from 0 to to 1 or at least 0 to an exit. Um, and so I started searching for that I mean it was a scary thought ah of of just sort of leaving and and figuring it out. Um, but I remember meeting. Ah, ah. Ah, one of my other mentors. Ah and and he ah ah you know David from from ide and he basically told me un it like your life has been sort of complete pre-planned for you till now like people told you to go to undergraard you went to undergrad go to college you went to college. Get a job. You know do do stuff now you’re actually trying to create a new muscle where you have to actually figure out what to do for yourself, right? Actually figure out how to how to pick something to do and and it’s scary. It’s hard, but but you know you’ll figure it out so it took me about None ars to to figure out what to do next. But. It was a beautiful beautiful time

Alejandro Cremades: Now you’re talking about this a lot. You know you have pretty amazing mentors. So how how do you meet those mentors and then how do you? How do you really set up the expectation for them to be a mentor I Mean how do you go about that broadly a lot of people that are listening are wondering.

Ankit Gupta: Um.

Alejandro Cremades: How they hell us Andki get this insane mentors. So.

Ankit Gupta: Ah, ah I think I’m just very transparent about the help I need like I I ah feel like I I sort of ask you know? ah and and I.

Alejandro Cremades: Ah.

Ankit Gupta: Like I also listen and and execute on the the guidance so that gives the mentor more confidence in in me. Ah I Also love networking actually like I you know I genuinely like meeting people and I genuinely like hearing their stories and I. Like I can identify something in the person I’m meeting. That’s interesting and that I can learn from or if I can contribute and they can learn from so I don’t know I like I like building connections. Um and just asking when when I need help.

Alejandro Cremades: Now one one important connection that you made was obviously the most important important connection in your life is with your wife and and she’s had a tremendous impact you know obviously in your life but obviously on what we’re talking about you know on your career and and she’s a physician.

Ankit Gupta: Um.

Ankit Gupta: He says.

Alejandro Cremades: So you know out of the conversations with her that got you thinking and into the discovery phase that you were alluding to So I guess that it ended up coming the push from your own wife.

Ankit Gupta: Um, yeah.

Ankit Gupta: Um, I know I know it’s so funny. Ah I after I left Linkedin I I ended up getting married and you know like you said my wife is a physician. She’s an internal medicine physician and ah you know. I had never known much about the healthcare space. Um, and and it’s funny how these things happen. But yeah through through our dinner table conversation through just sort of learning more about what she’s doing I realized that you know there’s a bunch of patients with substance use disorder that are showing up at the hospital. Um, and and I started learning more about it and started talking to patients and I started learning about how opioid use disorder specifically is is a massive problem and how there are treatments that are quite efficacious but but are not available. Um and just started learning more. Ah, about the clinical model about the space talking to more people in recovery and the more people I talk to the more I um felt personally connected because you know opioid addiction can happen to anyone. It starts from a pill that gets prescribed in a regular medical setting. Ah, and and you know when I heard their journeys into recovery There were so many barriers that that came up um and and I started but bicycle because I felt like those barriers we could easily overcome and we could massively improve access to to treatment. Um, but yeah, you know it’s my my wife definitely had a pretty big role to play and even I mean she continues. She’s my she’s my emotional co-founder you know through this journey.

Alejandro Cremades: I Love it now Now in this case, you know for the people that are listening to really get it. What ended up being the business model of Bicycle health. How do you guys make money.

Ankit Gupta: Yeah, so we provide treatment for Opioid use disorder through telemedicine and so we have a comprehensive care model that combines medication Management Psychotherapy Peer support recovery coaching at home drug testing case management care coordination and a lot more. And this comprehensive care model is delivered by our team. So We have a full time team of medical providers licensed clinical social workers certified recovery coaches, clinical support specialists and so we have the largest medical group. Um for addiction medicine in the Country. Um. And we make money through through two ways. Ah we contract with health plans um through a value-based care model and so we ah you know build health plans for the services we provide their patients. Their members. Ah and then for patients whose health plans or Health Insurance. We don’t Accept. We also have a self- pay Mode. So Our patients pay us a monthly subscription fee of 199 a month. Um for all of the services that we provide them.

Alejandro Cremades: And and and for you guys you know here it sounds like covid was very productive. So what happened what happened what happened in covid because I mean it it was just like 4 of you and then all of a sudden everything explodes in a very nice way.

Ankit Gupta: Um, but that.

Ankit Gupta: Um, it was a silver lining. Um so you know there was a pretty big regulatory change during covid ah, there’s an opt that I and hate at which mandates that an in-person examination has to be provided to the patient. Before prescribing controlled substances over telemedicine. It’s a federal app. Ah, and since the medication we provide buprenorphine naloxone is a controlled medication we we are beholden to Ryan Haup ah this act was actually waived during covid so during the covid public health emergency the Ryan hate act is waived and so that ah allowed us to provide our model fully over telemedicine versus a hybrid model. So it obviously made the model more scalable now for the first couple of months into the pandemic ah we were just learning about the impact of this change. Ah, and so before the pandemic bicycle health was a clinic in Redwood City it was not a venture backed company. It was a small business. Ah. And there were 3 or 4 of us in Boston which is the headquarters team and then there was a clinic in Redwood City and we were seeing patients in person at the clinic and then continuing treatment over telemedicine if that was appropriate but as soon as the covid public health emergency happened. Everyone started working from home. Our clinications are our administrative team. And so we moved all of our patients to the telemedicine model and then we started monitoring outcomes and we realized that the outcomes were actually getting better. We were more responsive to our patients we were more engaging retention and treatment was getting better the median time for enrolling a patient into our program came down significantly. And and so we thought that you know this is actually a really good opportunity to expand the service. Ah, and so that’s when I raised our sea drown. Ah um, and now we have raised a couple more rounds subsequently where we essentially went from one city to the entire state of California overnight. Ah, we were blown away by the demand. That’s what led me to raise around and and and grow this as a venture back business. Ah, and then now we’ve scaled bicycle into several more states we’re in 26 states now and and we’re continuing to be ah you know the largest ah national provider.

Alejandro Cremades: Nice now. How much capital have you guys raised today.

Ankit Gupta: Um, we’ve raised about just over 80,000,000 so far.

Alejandro Cremades: I mean obviously this is the None time around that you are going at it so you probably learn quite a bit from the good the bad and the uglygli of investors. So why did you choose the money you know from these investors versus other investors.

Ankit Gupta: Um, yeah.

Ankit Gupta: Um, so ah, I’ve always so so this time around you know I’ve always raised from investors to solve a specific problem. Um. So there’s ah, they’re solving a problem and then there’s also bringing the right type of investor on board. Ah so our seed round releases from signal fire where we were pretty much a direct-toconsumer service at that point signal fire has a ton of experience in tech-enabled services. Um, and they really help us scale. Quite a bit you know 10 to 15 x in revenue the first year. Ah really helped us grow the business and unblock us in in in a lot ofba. Our series a I realized that you know we we’re a great consumer business but we actually are a pretty ah ah, pretty specialized healthcare service and so we need. Bring investors on board that understand healthcare that can help us get connected to payers providers that can help us scale a healthcare service in a high quality and a safe way for our patients in a regulatory compliant way and so I brought on Questa Capital first chrisy ventures city like capital. You know investors with a lot of healthcare experience. Ah and then in our Cdb we’re we’re much further along ah I think we’re a core service in the health care industry now where we’ve seen you know over None patients. We’ve contracted with all the major commercial health plans where. Continue to go broke quickly where we have ah ah the best care model and and and fantastic outcomes to support the care model in a peer-reviewed publication. So you know we have the basics of the business in place now it’s time to actually scale this to realize our mission where None people misuse opioids every year. And so we need to for us to make a significant impact in the opioid epidemic we need to reach thousands hundreds of none of patients and and scale this as a sustainable business and that’s why I ended up ah raising money from internet and partners because they have seen this story before. Ah, taking them piece from series a seriesdb all the way to being public. Ah and and that’s the kind of expertise I need so you know I feel like I have the the luxury of being powerfulful. Um now. But also why bringing investors on I always talk about this tradeoff between. Growth and safety right? There’s always going to be times when we have to ah think about you know, do we want to grow more quickly or do we want to invest in clinical quality, patient safety, etc. And how do we trade these things off and I think we’ve seen some of those examples recently with ah with.

Ankit Gupta: With companies in the telemedicine space and and so I think when Investors Share. There’s no,, There’s no right Around. It’s its it’s nuanced and when investors share a way of thinking a framework a nuance but feels right? and and that’s something that I learned from ah that’s when I. Knowing that this person is the right person to to join our board.

Alejandro Cremades: Now if for you I mean imagine that you go to sleep tonight and you wake up in a world where the mission or let’s say the division of Bicycle Health is fully realized what does that world look like.

Ankit Gupta: Um, wow I would be that would be magical but ah is there a pale for that I take the blue pill. ah ah I think that world looks like 1 where.

Alejandro Cremades: I.

Ankit Gupta: Addiction is understood as a medical and a behavioral health condition just like diabetes Hypertension. Ah Asthma. It’s a condition to be assessed and. Ah, but treatment for the condition is quite widely available. Um and and at a high quality. You know if you get assessed with addiction. You can start treatment right Away. Ah and the treatment is high quality and will actually help you overcome your addiction. Or or at least be quite functional while maintaining maintaining treatment. Um, and it’s something that actually allows anyone with addiction to live a ah successful life A happy life. You know achieve Independence achieve wellness achieve help achieve ah their their social goals. Um, you know it doesn’t become a albatross around your neck. Ah it. It actually becomes just another medical and Behavioral health condition to be. Managed and improved upon and and prevented.

Alejandro Cremades: Now imagine if I let’s say I put you into a time machine and I bring you back in time I bring you back in time you know to Stanford you know when you were like there you know, ah you know having a chat with with classmates and.

Ankit Gupta: Um, okay.

Ankit Gupta: Um. Um, yeah, yeah, yeah.

Alejandro Cremades: And figuring out what you were gonna do and and and and maybe starting a business if you were able to to sit down that that younger self and tell that younger and kid 1 piece of advice before launching a business. What would that be and why give me what you know now.

Ankit Gupta: Um, oh my God I know exactly the answer to this question. What I would say is un it start doing the work right? like don’t overthink it. Don’t think you have to read a lot or talk to a lot of people or you know sit in your room and write the code and rewrite the code multiple times like just start doing the work like put it out there. You know start putting posts online start shipping your code start showing your work. People start asking for help right? like start doing the work and and like the bias towards action I think I’ve become better at holding back my nervousness and my you know ah, kind of insecurities and and and just. Going out and and and doing the work and I think that’s making me making me better up the like leading at at raising at at Producing. Ah.

Alejandro Cremades: So I love it now for the people that are listening that want to reach out and say hi. What is the best way to do so.

Ankit Gupta: Um, yeah I’m open to connecting on Linkedin ah, you know my Twitter is at gunki. Ah, my email is unkipped at Bicyclehealth Dot Com ah you know feel free to reach out.

Alejandro Cremades: Amazing! Well hey and Keith thank you so much for being on the deal maker show today. It has been an honor earth to have you with us.

Ankit Gupta: Um, thanks a lot. It’s been great.

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