Roberto Cipriani On Raising Over $380 Million To Bring Personalized Learning Support To Students

In the bustling world of startups, success stories often revolve around rapid growth, agile decision-making, and the ability to adapt to evolving market needs. One such tale that embodies these elements is the journey of Roberto Cipriani, the co-founder of Paper, a pioneering edtech company aiming to bridge the gap between what schools provide and what students need to succeed.

The venture, Paper, has attracted funding from top-tier investors like Sapphire Ventures, SoftBank Vision Fund II, IVP, and Framework Venture Partners.

In this episode, you will learn:

• Embrace the transformative power of education fueled by determination and perseverance.
• From freelancer to entrepreneur, recognize pivotal partnerships and seize opportunities for innovation.
• Navigate challenges with agility, pivoting strategies based on customer feedback and market dynamics.
• COVID-19 catalyzed digital education, underscoring the importance of adaptable solutions like Paper.
• Fundraising demands discipline, storytelling prowess, and strategic networking for startup success.
• Surround yourself with diverse expertise, fostering a culture of continuous learning and growth.
• Paper’s journey exemplifies resilience, innovation, and a commitment to bridging educational equity gaps.

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About Roberto Cipriani:

Roberto Cipriani is currently the Co-Founder, COO & CTO at Paper and has over 10 years of experience in web development and software solutions.

Prior to Paper, Roberto was the President of RobertoDev.com Inc., a web development and software solutions company for small to large businesses.

Roberto has also worked as a web developer for Killersites.com Inc., where he helped students develop marketable web skills quickly.

In addition, Roberto has conducted research on visual motion processing in monkey visual cortex as a Masters Research Student at the Montreal Neurological Institute and Hospital.

Roberto Cipriani obtained his high school diploma from Lasalle Comprehensive High School in the field of physical sciences.

He then completed their bachelor’s degree in physiology from McGill University. Roberto is currently pursuing his Master’s in neuroscience from McGill University.

Connect with Roberto Cipriani:

• LinkedIn
• Crunchbase
• TheOrg
• F6S

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty hello everyone and welcome to the deal maker show. So today. We have ah an amazing guest. You know we have a founder that they has been building scaling financing something very exciting. You know without a doubt covid they gave them a really nice push but we’re gonna be talking about. All of the good stuff that we like to hear you know in this case, how they went ah ahead you know with being able to to manage you know with the fast decisions with crazy scaling. Also they’ve they’ve raised close to 400000000 and they’ve also you know along the way they’ve done a bunch of pivots. You know, basically they listened. And they adjusted themselves you know in order to really give you know folks what they needed. So I think that they we have a very inspiring conversation ahead of us so without further ado. Let’s welcome our guests today Roberto Chi Pririani welcome to the show.

Roberto Cipriani: Thank you very much a hand it very very happy to be here.

Alejandro Cremades: So so originally you obviously had your parents from italy but they they immigrated to Canada and you ended up growing up in Montreal so give us a walkthrough memory lane. How was life growing up.

Roberto Cipriani: And but of course I would say life growing up was was pretty great as you mentioned grew up the son of italian immigrants came came to Canada following the promise of better opportunities as as many immigrants have. Um, and really from a young age. They instilled this importance of education to me and and tommy that I would say education is probably the greatest equalizer. Um, really that my education was a way to take a step forward that you know they didn’t really have um so school was always important to me I was. But a lot of effort I felt it was an honor to have the opportunities that I did to go to um, high school and university um, so went studied at Mcgill University here in Montreal um, originally in physiology and then went. Yeah.

Alejandro Cremades: And quick question and quick quick question there because I think that one thing that is Incredible. You know from your parents is the way that they instill the um education you know in you and the importance of education seeing education as an equalizer. So. Why was education so important for them and what did they see that education could ah look for you.

Roberto Cipriani: I Think you know being immigrants and not speaking the language they felt it was a way for me to like I said take that step up learned Language. Um. A better master The language I would say better than they wish they could were where they could have um and really it was um if I especially with that generation if you put your time and effort in School. You’ll get the most out of it with your career. And don’t think that’s the case Anymore. By the way I need to get that into that as a separate conversation but really at that time the combination of them being immigrants wanting me to to fit in do the best that I can in school to really act as a springboard into my career and would allow me to do anything that I wanted.

Alejandro Cremades: So obviously seeing them as immigrants you know, working hard seeing them going through their journey to I mean I’m an immigrant too in the us. So I really understand you know what? what? it looks like So how do you think that that’s shaped who you are today. You know seeing them going through that journey too.

Roberto Cipriani: Ah, with my career.

Roberto Cipriani: I think that that’s a great question. Um, it really made me understand the value of hard work and perseverance. Um, you know, ah, you’re you’re an immigrant yourself when you’re coming to a new country. Ah lot There’s a lot more than just the day to day that you need to do you need to figure out how to speak the language you need to you know my parents were very young so they went to so they did go to school um part of their schooling in Montreal here in Canada but it’s about fitting in. It’s about understanding the culture. It’s trying to keep hang on to your culture while you’re learning a new culture. Um, so so for me ah there was there’s a lot more that goes on and a lot that they had to take on that I ah fortunately didn’t have to put on my back. Um, so I would say that. For me, it all came down to hard work and perseverance and that’s something that I’ve I’ve I’ve held very closely um and still to this day I think that a lot of the success that I have had um has come down to being persevering through the hard times.

Alejandro Cremades: And you went to eventually to Miguel University you know an amazing university and and they’re ultimately that that’s what gave you the push to really understand that you eventually wanted to pursue a career in technology so walk us through what we’re. Those sequence of events that they kind of like propelled you in in in in that career path.

Roberto Cipriani: Of course so went to Mcgill originally to study physiology um was really interested in academia I feel like I’ve always been a scientist at heart and went to grad school studying competitional neuroscience I was in the ph d program.

Roberto Cipriani: I saw myself as being an academic I would you know finish my ph d go do a postdoc somewhere and then move on to my own line. Um, during my time in grad school I think I would I would say that I really enjoyed the computational part a lot more. Um. What I mean by that was there’s a lot of programming skills that I was developing doing tons of data analysis data science then I started to build the software that we needed to run the experiments and I realized that you know that was where I felt the most fulfilled it was in building the technology it was in solving. Complex problems. Um, but using sort of code to express that. Um, and I realized that you know I could as as I dove into it more and more I felt like academia was um, less and less what I wanted to do and i. Decided to actually drop out of grad school and instead pursue a career in technology.

Alejandro Cremades: So tell us about what that looked like because obviously for you freelancing you know was say part of that journey but eventually you know that freelancing you know, got you in touch with Phil and and all of a sudden you know you become ah an entrepreneur. So um. Wokash. How do you guys initially connect. What were some of the projects that you were doing earlier and and and what were those synergies. How did they come together for paper to be born.

Roberto Cipriani: Of course, um, so as you mentioned I was a freelance software developer so I had a bunch of different clients primarily based on Montreal small to medium size businesses that needed some piece of technology to be built whether it was a web app or something on the backend. Um I was introduced to my co-founder Phil um through a mutual friend. Um Phil had a local in home tutoring company here in Monhel. So as as a parent if you need somebody to come help your son with your daughter with math homework. You call this number and a tutor shows up to your house. And I was introduced then because he wanted to build some technology in order to help so scale the business to a certain extent so we were introduced and we worked on and off together as myself as a freelance software developer and Phil as you know, reming this in-home. Local tutoring company for about I would say a year and a half and then as our relationship started to develop and we were you know both excited with working with each other um Phil approached me with this idea um of bridging the equity gaps. He was seeing in his classroom as ah as a classroom teacher. Um by using technology to provide support to these students who you know students who go home and maybe their parents are both working and their parents can help them with their schoolwork or you know parents that can’t afford a private tutor.

Roberto Cipriani: Show up to your house 2 to three days a week um I knew that I wanted to help others in their educational journey because I felt that I was able to take so much from my educational journey that um I a felt like there was an opportunity there. Um, and b it felt like something something that would fulfill me. Um, if we were successful and. Decided at that point we would start a company together and really again bridge this these equity gaps that exist throughout our education system.

Alejandro Cremades: So Ultimately that was getting the academic support with tutoring and and bringing it online So when you’re seeing stuff that is working or maybe that is not working Offline. What is that the thought process of figuring out how you bring it in a digital. You know, kind of way and in a way that also Scales I mean what were some of the things that you guys were looking at in order to you know make this thing happen.

Roberto Cipriani: Yeah, so originally you start simple right? We are trying to take the offline in-home experience and bring it online make it more affordable because now tutors don’t have to travel to go see their the students they could do it from the comfort of their home make it accessible. We were building out an online classroom with video conferencing with a collaborative whiteboard with file sharing. Let’s not forget that this wasn’t about ten years ago in 2014 so video conferencing wasn’t um, as popular obviously as it is today. Um, so we just wanted to recreate that en home experience online? Um, but you when you once you build ah an initial version. Ah you quickly learn from listening to your customers. What is best for them and what they’re actually looking for.

Alejandro Cremades: So I guess for the people that are listening what ended up being the business model of paper. How do you guys make money today.

Roberto Cipriani: So we make money today primarily through selling paper or access to our platform directly to public school districts all over the us. Um, the school district pays for it that that way all students. Um. At this public schools or at these public schools have access to a tutor online twenty four seven um so that’s really addressing those equity gaps doesn’t matter how much money a student’s family makes if they are going to this ex public school district then they’re getting access to academic support. Anytime that they need.

Alejandro Cremades: So I know that it was a process to obviously get to this point you know you guys say definitely took a look at the market as you were moving along whether it was 2015 on the way that you pivoted from video to Chat. Or for example, the way that you guys were thinking about monetizing. How do you guys typically go about listening listening to what the market is looking for and adjusting yourselfs to be able to do that because in many instances you see companies failing to be able to do that because they are not able to do so effectively. So. How does that work for you guys. How have you been effective at listening and implementing. You know those saying those insights.

Roberto Cipriani: That’s a great question I Really believe it’s all about time and market and being as close to the customer as possible. Um, originally I mean you you referenced? um, pivoting from video at the chat that’s because we spoke to our tutors and our students. Every single day every time there was a tutoring Session. We would ask the student hey what could have been better speaking to our tutors. What did you? How did you find the session. What could we have done better for you. Um, and it was the same thing and it stills the same thing Today. It’s all about being. Having time and market being close to the customer today. It’s a little bit more complicated for us because our customer is the school district and the superintendent but ultimately the end user is the student but it’s about spending time with the superintendents about spending time with our students but spending time with the teachers who are also. Users of paper and listening make when we say listen it doesn’t mean going there with your presumption of what they want. It’s actually allowing them to share tough feedback and you listening to the feedback and creating that space where they feel comfortable sharing what they actually want. And once you get that information. It’s about going back filtering it and giving that information to your teams then they can build what’s right for your users.

Alejandro Cremades: So Then for example in in in the case of monetizing I mean monetizing I mean the way that you are pivoting perhaps features or experiences I think maybe it’s a little bit less nerve wracking than people Think. Ah. Business model How you’re monetizing I mean initially you guys were going Direct. You know to? for example, like they they they before you know you were going to like the students or maybe like the teachers then you guys thought that it was better to go to institutions and schools which tends to be probably like a longer sales cycle.

Roberto Cipriani: Exactly.

Alejandro Cremades: And it’s probably nervef rocking going from like getting money quicker than all of a sudden you know you’re waiting you know, rolling your thumbs. Oh my God I Hope this thing works out. So how did you guys go about making that adjustment because I’m sure that that was not an easy one for you. All.

Roberto Cipriani: That’s that’s a great question and that part of that is listening to your customer and it’s when you’re talking to schools and the superintendent’s recognizing that for them. 1 of their biggest initiatives is to better support their students and their communities. But part of that is also you know we knew in order for us to succeed in our mission. Um, that we would have to sell directly to public school districts if we really truly wanted to bridge the equity gaps even if we made. Paper and we at one point we were selling at $15 a month for unlimited access to tutoring selling it directly to parents and students. We still knew that that doesn’t address truly address the equity gap because there are still families that even $15 a month is a very hard sell because. Their money is their their money is going elsewhere and to supporting their family. Um, so for us we we felt it was a bit of pull from the market but a little bit of push from us because we knew in order to ultimately address these equity gaps we need to sell to the public schools. There’s. Public education is funded very well throughout all of the us and in Canada and we knew that speaking to the superintendents. There was an opportunity there and we just felt really strongly that our solution was the best way to solve the problem of supporting their students and their communities.

Alejandro Cremades: It sounds like also Covid changed everything. You know it accelerated being able to achieve the ah vision that you guys were hoping or getting closer to to that by a mile and although that could sound very appealing is also. Very dangerous because you got to adjust yourself very quickly. You know to things and sometimes you make decisions without really having all the information that is needed So What happened during Covid What why did things change so rapidly for for paper.

Roberto Cipriani: I would say the biggest reason um, was that overnight um district leaders understood how important it is to properly embed technology in their district. Um, you know, ah pre pandemic. And let’s say March of 2020 about 65% of students in the us had access to a device. Um ah through their school and within three months or four months from March to July or August that number increased the 95% and then by the end of Twenty Twenty about 99% of students had access to a device through their school and and if you want to talk about being equitable. You want need to ensure that all of these students have access to a device so they can then access the technology and the software and the services that are going to. Help them improve throughout ah improve their academics and and make give them a better ah journey throughout their their education as well. Um, so it was really the investment of the technology and the infrastructure that again was a springboard for paper because if a school did not adopt. Technology. Well how paper could not be a success right? We are a technology company selling access to a platform. So if students don’t have access to a device. They’re not going to access paper so we knew that once we saw this like increased investment in the technology infrastructure at the beginning of covid.

Roberto Cipriani: We felt paid. This is going to be a really big opportunity.

Alejandro Cremades: So talk us about the fundraising 2 because obviously you know you guys have raised quite a bit of money close to 400000000 to be precise 380 plus so what was the journey of racing money because I know that especially at the beginning you know going through the a or the b was say. Challenging but walk us through how things you know and also expectations happen in that journey of going from 1 financing cycle to the next.

Roberto Cipriani: Yeah I would say that financing um for paper has always been um, a lot of work and I don’t say that in ah necessarily a negative way. But um, it’s never fundraising has never been easy and and nor do I think it should be easy. Ah, for any company. Um, for an example of that as far as series a we pitched I think 125 different friends and we got 1 term gene um, but that 1 term she meant everything for the continued success of the company. Um, so.

Roberto Cipriani: Fundraising in our a was was was difficult. We needed to to pitch a lot of different finds I think the reason for us it was maybe a little bit more difficult was people always felt that ed tech was less sexy and you know long sales cycles and it’s hard to get into the districts and institutions. Um, but once you start to get more and more proof points that we were able to actually sell into public school districts. Um the fund raisingising started to get a little bit easier. Um, and yeah, but early on our Cd or series air series b it was a lot of work. We had ah a whole crn we were. Ah. You know it took the majority of of my time and and my cofounder Phil’s time in order to really make sure that we’re meeting all the right people having the right conversations and then getting us to a term sheet.

Alejandro Cremades: So now that they you obviously you know like have had your fair amount of lessons Learning. You know when it comes to fundraising. How do you go about? especially for all the folks that are listening now and wondering how they they get this this financings done especially at an early stage. What would you say is the biggest lesson there on making sure that you have a process that is you know super streamlined where you’re very effective and you’re not just throwing stuff on the wall but being very intentional on the way that you’re bringing investors and getting it done.

Roberto Cipriani: Yeah I think you’re you’re alluding to it somewhere. But I mean first of all the story has to be there your storytelling especially in earlier stages. You don’t have you know 2 3 years of historical data to um to show investors. But I would say the second thing is you need to treat this like a very serious process. Um, you need to ensure that you’re following up at the appropriate times you need to be direct and ask hey are you interested or not do you think this will go to a term sheet. Um, one of the. Pieces of advice that I got that was super effective is at the end of every meeting no matter which vc you’re talking to when are we meeting ask what? the next step is and and confirm the next step in that meeting or when are we meeting next is it with all of the partners have a lot of clarity on the process. And think something that’s interesting for you know paper having started in Canada is just a difference in culture between vcs in Canada and us I think in the us um, you, you know you can get a conversation with almost any fund but at least. Some ah principal or a partner at and it was any fun because um vc us go want to miss out on the next opportunity I think in Canada it’s slightly different or there’s not as much opportunity. Um, but making sure that you’re in the right conversations.

Roberto Cipriani: Obviously the networking and and and being involved in the startup communities wherever you’re based to make sure that you know the right people and then they’ll introduce you to the other people and the other Vc etc. Um, but ultimately it comes out of the process. The more disciplined you are in the process. Ah, more success you have in raising capital.

Alejandro Cremades: So roberto you go to sleep tonight and you wake up in a world where the vision of paper is fully realized what does that world look like.

Roberto Cipriani: It’s a world where every student feels supported throughout their educational and journey meaning whether they’re stuck on a question that they’re doing um on their homework the night before and needs to be submitted. Or they’re studying for an exam that they have in a week um the idea is that we are supporting students and really bridging the gap between what schools provide and what students need to succeed.

Alejandro Cremades: So obviously here we’re talking about the future but I want to talk about the past with a lens of reflection because I mean you guys have been at it. You know for a while you know we’re talking about a decade right? A decade in in startup compared to corporates like 100 years right I mean is this so it’s unbelievable now. Now let’s say you know I was able to bring you back in time maybe to 17014 where now you were bouncing around with fail. You know the possibility of creating something right and and building something together. Let’s say you were able to. You know, just show up into one of those meetings. Maybe where you guys were like thinking about that future together and maybe at one of those coffee shops there in Montreal and and you were able to just appear there just sit down with those say younger you know selves of you and Phil and you were able to give the 2 of you guys 1 piece of advice. Before launching a business. What would that be ny given what you know now.

Roberto Cipriani: There would be 2 pieces of advice that I’d have to give um the first one is to persevere through every challenge. Um, we have persevered so I would feel like that’s a less important piece of advice that I would want to give to my anger self or. A younger version of Phil but it’s definitely about persevering if you truly believe in what you’re doing then it’s going to be really hard and you don’t want to quit a lot of the time. Um, but if you really believe it don’t I would say the second piece of advice. Um and one that I would more. Honestly, give to my younger self. It’s really important that you surround yourself by people that are better than you and really understand when you’re not good at something. There are people out there that know that thing way better than you do the earlier you bring those people in the quicker. You’ll find success.

Alejandro Cremades: And and just to double click on that you know I think that it’s is very difficult to be able to to get to the point of really understanding that you don’t know what you don’t know to be able to surround yourself by those people. So what does that process look like when you’re like my God I definitely.

Roberto Cipriani: Exactly.

Alejandro Cremades: Don’t know this and I need someone you know to ah to come in and then how do you go about finding that. So and I mean what what have you learned in your in your own journey.

Roberto Cipriani: I Think that um we all and it’s impossible to know but to know what you don’t to not know to know what you don’t know. Sorry um but I feel that as entrepreneurs.

Roberto Cipriani: We all have a bit of an instinct and we know somewhat deep down inside almost subconsciously that this area of the business. It’s not really working out right now but you just don’t pay attention join it and you hope that it’ll just survive through whatever change you’re going through I think it’s. A little bit about listening to that uncomfortable gut feeling a little bit earlier and saying you know what? this probably means that I’m not understanding. What is what needs to go on in this part of the business. Let me bring somebody in and then knows what they’re doing and really help us accelerate in our growth. Um, so it’s not It’s not like there’s a there always is a moment in time when you realize it but for me and you know I’m assuming for most entrepreneurs. It’s always a little bit too late I always had I had that uncomfortable feeling for three to four months but I didn’t feel like needed to address it. Until it’s always just a little bit too late. It’s really about as soon as you get that feeling that probably is taught your butt your you’re subconscious trying to tell you you need to be paying a little bit more attention here and you probably don’t know what you don’t know and you just need to bring somebody in that does know.

Alejandro Cremades: So roberto for the people that are listening that would love to reach out and say hi. What is the best way for them to do so.

Roberto Cipriani: Best way is on Linkedin you can find me my name is ro chipardani and I’m I’m available Linkedin I’m very active or try to be reactive at least.

Alejandro Cremades: You say enough? Well Roberto. Thank you so much for being on the deal maker show today. It has been an honor to have you with us.

Roberto Cipriani: It’s been a pleasure. Really appreciate it and thank you so much for having me a andro.

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