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Paper Trails—Roberto Cipriani's Mission to Give Every Student a Fighting Chance
Episode 7121st May 2025 • Designing Successful Startups • Jothy Rosenberg
00:00:00 00:36:33

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Roberto Cipriani

Bio

Summary

Roberto Cipriani, the founder of Paper, elucidates the transformative journey of his educational technology company, which aims to democratize access to tutoring across North America. Launched initially as Grade Slam in early 2014, the company evolved through a rebranding in 2020, recognizing the inadequacies of its original name. Cipriani's commitment to providing affordable educational support stems from his own academic experiences and the desire to offer the same support he received to those in need. Throughout this podcast, I delve into the intricacies of navigating product-market fit, the significance of understanding customer pain points, and the delicate balance between rapid growth and thoughtful decision-making. The discussion ultimately emphasizes the importance of investing in oneself as a leader to foster a thriving organizational culture and to ensure sustained impact in the education sector.

Story

Grade Slam, initially conceived as a fusion of educational passion and sports enthusiasm by its founders, underwent a transformative journey since its inception in early 2014. The name, emblematic of their vision, proved to be a misnomer, as the company evolved to focus on democratizing access to tutoring, ultimately rebranding as Paper in 2020. This shift not only marked a new identity but coincided with the onset of the COVID-19 pandemic, which catalyzed an unprecedented demand for educational support. Throughout this episode, we delve into the intricacies of Paper's mission and the founders' commitment to ensuring that every student, regardless of socioeconomic status, has access to quality tutoring. The narrative unfolds through the lens of Roberto Cipriani, whose journey from a software developer to a tech entrepreneur illustrates the profound impact of technology in transforming educational landscapes. His insights provide valuable lessons on navigating the challenges of startup growth while staying true to one's mission, underscoring the importance of understanding customer needs before devising solutions.

Takeaways

  • The journey of Roberto Cipriani showcases the importance of understanding customer pain points before developing solutions.
  • Roberto's experience reveals that recognizing when to slow down during rapid growth is crucial for making impactful decisions.
  • Investing in personal growth as a founder creates a multiplier effect on organizational success and culture.
  • The evolution of Paper from Grade Slam highlights the significance of branding in aligning with the company's mission and values.
  • Roberto emphasizes the need to reframe budget conversations by demonstrating how solutions can enhance existing financial resources.
  • The success of Paper is rooted in its mission to democratize education and provide accessible tutoring for all students.

Transcripts

Speaker A:

We were called Grade Slam.

Speaker A:

That's how we launched.

Speaker A:

We launched in:

Speaker A:

Sorry in early:

Speaker A:

Started working on it in:

Speaker A:

And the, the company was called Great Slam and it was a concoction of my, the mind of my, my mind and my co founder's mind.

Speaker A:

And we both played sports, we both loved and were in education and it's like, well, Grade and Slam and it came all together and then we operated as Great Slam for the first six years and then realized it's a terrible name because we don't.

Speaker A:

We're not a great book, we're not involved with grades.

Speaker B:

Welcome to Designing Successful startups where we dive deep into the journeys of extraordinary founders.

Speaker B:

Today, I'm thrilled to introduce Roberto Cipriani.

Speaker C:

The visionary founder of Paper, an educational.

Speaker B:

Technology company that's democratizing access to tutoring across North America.

Speaker B:

From his roots as a software developer with a dream of helping students students to raising nearly $400 million and serving over 3 million students, Roberto's journey is a masterclass in finding product, market fit, scaling with purpose and staying true to your mission.

Speaker B:

We'll explore how he transformed a simple idea into a company that's changing education, why he believes investing in yourself as a leader is crucial for scaling and how competitive drive and a desire to give back fuel his entrepreneurial grit.

Speaker B:

Whether you're building your first startup or scaling your next venture, Roberto's insights on navigating the challenges of rapid growth while maintaining your core values will inspire and guide you.

Speaker C:

Let's dive in and hello, Roberto.

Speaker A:

Hello.

Speaker A:

I'm excited to be here.

Speaker B:

Glad you're here.

Speaker C:

You win the best background.

Speaker B:

People who are seeing the video are.

Speaker C:

Going to just, you know, be like.

Speaker C:

And if you, and if you move your head, then they can see that it's Steve Jobs at Bill Gates.

Speaker C:

That's pretty amazing.

Speaker A:

It's a piece called Exchange of Ideas by an Italian artist.

Speaker A:

And I think that's as an entrepreneur, you're exchanging ideas with the public.

Speaker A:

So it's an important piece to me.

Speaker A:

That's why I like to have it in the background.

Speaker A:

And it's also very eclectic.

Speaker A:

And I say this is what's inside my brain.

Speaker A:

Just a bunch of random stuff.

Speaker B:

Well, good.

Speaker C:

I'm glad at least your brain is doing stuff three dimensionally.

Speaker A:

Exactly.

Speaker C:

Roberto, start us off with just, just telling us where are you originally from and where do you live now?

Speaker A:

So originally from Montreal, currently still in Montreal, although, you know, I come from an Italian immigrant family, so, you know, Italian was my first language growing up.

Speaker A:

Until I went to school and then learned English and also, also French here in Quebec in Canada.

Speaker C:

Okay, so here you are.

Speaker C:

You know, you.

Speaker C:

You basically grew up in Montreal.

Speaker C:

Somewhere along the way, you got pushed into the entrepreneurial trap.

Speaker C:

And because once you're in it, you can never get out.

Speaker C:

But.

Speaker C:

So tell us your story about becoming an entrepreneur.

Speaker A:

Absolutely.

Speaker A:

And I agree, it is a trap.

Speaker A:

It's very, very hard to.

Speaker A:

I don't think you want to break out.

Speaker A:

So I think it's a good type of trap.

Speaker C:

One person told me that it's because once we're an entrepreneur, we're not employable by anybody.

Speaker A:

That's exactly it.

Speaker A:

I love that.

Speaker A:

It's a very wise words.

Speaker A:

So you know a little bit about me, how I ended up in the entrepreneurial world.

Speaker A:

Like I said, grew up in an Italian immigrant family.

Speaker A:

So school was always a big focus for me.

Speaker A:

My parents taught me that education is the greatest equalizer.

Speaker A:

I had a lot of.

Speaker A:

I felt it was important for me to do well in school and really take away not just academically, like from a performance perspective, but just take a lot away from school.

Speaker A:

So I actually ended up going to grad school here in Montreal at McGill University, studying computational neuroscience.

Speaker A:

I had this dream of becoming an academic.

Speaker A:

The best part of my day was building the software to run the experiments that I was running.

Speaker A:

Then I was running the experiment, and then I would love writing the code to then analyze these humongous data sets.

Speaker A:

So I already discovered this passion for computer science, programming, coding, whatever you want to call it.

Speaker A:

And I actually decided to drop out of grad school and instead pursued this entrepreneurial journey.

Speaker A:

Now that I had started developing what at that time was a very marketable skill.

Speaker A:

So I wanted to develop software for a living.

Speaker A:

Even within academia, it's somewhat entrepreneurial.

Speaker A:

Right?

Speaker A:

You need to apply for your own grants and your own funding.

Speaker A:

You do have someone that oversees the work that you're doing.

Speaker A:

But it's in my mind that's sort of like a board they help govern, but you're sort of making a decision day to day.

Speaker A:

And when I dropped out of the PhD program, I said, you know what?

Speaker A:

I'm going to do this software thing on my own.

Speaker A:

And I don't know it just for me, autonomy was always a really important thing.

Speaker A:

So was a software developer for a few years before I started the company, which I'm sure we'll talk a little bit about, called Paper.

Speaker C:

Yeah, we will.

Speaker A:

My undergrad was in physiology and then did this computational neuroscience.

Speaker A:

So as a hacker I even hacked my way into learning about computer science and how to program.

Speaker A:

So I feel that I was lucky especially to learn in the model of grad school, which again, you're very autonomous.

Speaker A:

You're an independent thinker.

Speaker A:

You do it on your own time.

Speaker A:

I didn't have a class to teach me.

Speaker A:

This is how you need to develop the software.

Speaker A:

It's like you need to build this thing in order to run the experiment.

Speaker A:

Figure it out.

Speaker A:

So I'm actually really grateful that I got to learn in that environment with.

Speaker C:

The life of Roberto those many years ago, who was trying to build the software to run these experiments.

Speaker C:

If that Roberto was.

Speaker C:

Was doing that now, wouldn't his life be a lot easier because you would just turn and tell your favorite AI write a program that does this?

Speaker A:

I believe so.

Speaker A:

And you know what?

Speaker A:

I said the word grateful.

Speaker A:

I'm also grateful that I learned it at the time I did because it was an incredibly marketable skill back then.

Speaker A:

I'm talking about in:

Speaker A:

And I would say it's really not the same anymore.

Speaker A:

I get a lot of questions about what advice could you give me?

Speaker A:

So I'm thinking about going to computer science and trying to develop an app or a website or web apps, which is what I was doing at the time.

Speaker A:

It's really not the game anymore.

Speaker A:

And I tell them, obviously, which is going to be very easy to understand.

Speaker A:

Just go into AI and learn about AI.

Speaker A:

And also on the data side, I think there's a lot of marketable skills to learn on data.

Speaker C:

Well, let's get into Paper because that is a big thing that, that's taken a lot of your.

Speaker C:

A lot of years and.

Speaker C:

But it's a very interesting company and it seems to be doing very well.

Speaker C:

And you got a great name.

Speaker A:

So a little bit on that actually is we were originally not called Paper.

Speaker A:

We were called Grade Slam.

Speaker A:

That's how we launched.

Speaker A:

We launched in:

Speaker A:

Sorry in early:

Speaker A:

Started working on it in:

Speaker A:

And the.

Speaker A:

The company was called Great Slam.

Speaker A:

And it was a concoction of my.

Speaker A:

The mind of my.

Speaker A:

Of my mind and my Cosandra's mind.

Speaker A:

And we both played sports, we both loved and were in education.

Speaker A:

And it's like, well, Grade and Slam.

Speaker A:

And it came all together and then we operated as Great Slam for the first six years and then realized it's a terrible name because we don't.

Speaker A:

We're not a grade book.

Speaker A:

We're not involved with grades.

Speaker A:

And people would frequently call us a grand Slam.

Speaker A:

ctually decided to rebrand in:

Speaker A:

Happened to be fantastic timing for us.

Speaker A:

And we rebranded to Paper and it was at the time, you know, my co founder was the one that came up with the name at the time.

Speaker A:

Like, how is there no company called Paper?

Speaker A:

This is like, we thought it was like the best possible name and you know, it.

Speaker A:

It grew on us in that moment and you know, and destiny grew with us at the company.

Speaker C:

And I'm also amazed that you could get Paper Co as the URL because, I mean, did you have to buy it from anybody or did you really just go to a domain supplier and there it was.

Speaker C:

You could have it.

Speaker A:

It was so Paper.

Speaker A:

No, we did have to, we did have to buy it through an agent.

Speaker A:

It wasn't what I would think at the time that expensive.

Speaker A:

I don't remember the exact price, but it was in the low thousands of dollars for, you know, domain real estate, which has value, it's an asset.

Speaker A:

So yeah, it was available.

Speaker A:

The company name was available.

Speaker A:

Paper.com Funny story is, was not available because so silly because paper.com just redirects the staples Paper like product page.

Speaker A:

So it's not even like, I don't even know if they care about it.

Speaker A:

We tried to buy it from them, but they said it's not even a price thing.

Speaker A:

It's not like we would almost give it to you for free, but it just, we don't want to sell it.

Speaker A:

So we went with Paper Co, which we felt was as good as we're going to get.

Speaker C:

Well, tell us got you to form it in the first place, of course.

Speaker A:

So, you know, if we pick up where I left off on my story.

Speaker A:

I was a software developer for five, six years.

Speaker A:

And then in:

Speaker A:

We felt if we can provide students with tutoring in an affordable and accessible way using technology, we felt that the market, the majority of the market, the 80 or 90% of the market, was being completely underserved by other tutoring companies.

Speaker A:

Tutoring has always been a very expensive endeavor, paying 50, $60 an hour to have someone come to your house and help your kids with math or science.

Speaker A:

d starting to do it online in:

Speaker A:

But again, it was very much focused on the top 10% of wealthy families.

Speaker A:

So we thought if we can use technology and take that business model but serve the 80 to 90% of families that couldn't afford tutoring on a regular basis.

Speaker A:

Not only that, an amazing opportunity to build a big business, but we could really make an impact on the education and the academic journey of millions and millions of students.

Speaker A:

So we kicked off on this journey.

Speaker A:

We didn't really know exactly what we wanted to build, but we know we wanted to be able to recreate that feeling that a student gets when they're unblocked.

Speaker A:

And a lot of the time, that's a tutor that does that.

Speaker A:

So my co founder had the education background.

Speaker A:

He was a former teacher.

Speaker A:

I had a tech background, and we felt we had the right set of experience to really make a difference in the industry.

Speaker A:

And we kicked off paper and I could dive into what happened after we started the company.

Speaker A:

But I'll just take a break to see if you have any questions on that.

Speaker C:

What I'm interested in understanding, because you were not an experienced startup founder, this was your first go?

Speaker A:

Yeah.

Speaker C:

You know, sort of one of the reasons that I wrote this book and I'm doing these podcasts is to start providing more resources for startup founders like.

Speaker C:

Like you were in:

Speaker C:

Did you make, you know, mistakes?

Speaker C:

You know, obviously none of them were.

Speaker B:

Fatal because it's still going great.

Speaker C:

But how hard was it at the.

Speaker B:

Beginning to know what to do?

Speaker A:

It's a really, really good question.

Speaker A:

Obviously, there's a million mistakes, just like every sounder.

Speaker A:

I mean, if I found or said they didn't make any mistakes, I would definitely not believe it.

Speaker A:

But in terms of knowing what to do, I think that's a really, really good way of framing it.

Speaker A:

I think that the philosophy that we had is deeply understanding the problem of the customer and then figuring out what the solution ends instead of having a solution and then figuring out which problem you're trying to solve.

Speaker A:

For us, that meant we knew we wanted to provide tutoring to students.

Speaker A:

We didn't even know who our customer was.

Speaker A:

Is it the customer?

Speaker A:

The student?

Speaker A:

Is there a customer?

Speaker A:

The parent, the customer?

Speaker A:

The school is our customer, Whoever, A teacher.

Speaker A:

Right.

Speaker A:

But we knew that we wanted to solve a problem, which was that a majority of students weren't getting access to the extra help that they needed.

Speaker A:

But then a small portion of the students did.

Speaker A:

And because our mission from day one was this idea of democratizing education, we were just very mission oriented in solving this problem.

Speaker A:

But it took us four.

Speaker A:

So from:

Speaker A:

Because first we're like, hey, let's solve this problem for students.

Speaker A:

Let's sell it directly to the student or the parent.

Speaker A:

We did that for a year.

Speaker A:

We can make it more affordable.

Speaker A:

We built a bunch of technology at the time using WebRTC, HTML5 in the browser, video conferencing, which nowadays is just standard at the time was sort of new and we realized we're able to make it slightly more affordable, but still not affordable enough at the same time.

Speaker A:

We recognized students hated being on camera and just wanted to get help on their simple math question they had at the end of the day.

Speaker A:

So we started to learn a lot more.

Speaker A:

Well, the student doesn't want to have video.

Speaker A:

The parents can't really afford it.

Speaker A:

Well, how are we going to continue to solve this problem, which is getting the help to the students and ultimately landed on the only way we can get this to be affordable and accessible is to sell it directly to public schools.

Speaker A:

Public schools pay for access to the tutors, we train the tutors and then we help the students at the public schools.

Speaker A:

So there's no cost to the students.

Speaker A:

But we build the technology to sit on the infrastructure of the public schools.

Speaker A:

We make it easy for the public school to work with paper.

Speaker A:

They pay for it, students get it for free, and now they have unlimited help whenever they need.

Speaker A:

So really it's about the understanding what the problem is and spending the time to deeply understand that problem.

Speaker C:

Okay, so that leads to me to two real related questions to what you just described.

Speaker C:

So I don't forget them, I'm going to say them both and then so one is, is the infrastructure at, at all the schools similar enough that you don't have to like redo this a bunch of different times.

Speaker C:

And the other question is, I cannot imagine that a school has a lot of extra money in their budget.

Speaker C:

So you must have figured out a way for some money that they were already spending to be redirected to you.

Speaker C:

So those are the two questions.

Speaker A:

I'll touch on the first one first.

Speaker A:

Just because it's a super easy answer.

Speaker A:

Yes, infrastructure.

Speaker A:

The technological infrastructure was similar enough.

Speaker A:

There was enough interoperability that it was very easy for us to plug into the student information systems and learning management systems at most public schools.

Speaker A:

That's the answer to that.

Speaker A:

Your second question was a really good question.

Speaker A:

The perception that schools or public schools don't have money is, in my mind is not the right way of framing it.

Speaker A:

We're talking about the bigger districts have billion dollar budgets.

Speaker A:

So say that you don't have money.

Speaker A:

It's crazy, right?

Speaker A:

I'm not saying you said that, but generally that's the perception what you're actually doing and you've definitely been an entrepreneur before because you alluded to it, is you're just competing for dollars that already exist.

Speaker A:

And instead it becomes a conversation about prioritizing paper in their budget over other items and not whether do they have enough money to pay for paper.

Speaker A:

And it's like just that simple reframing.

Speaker A:

I find for us at a big impact.

Speaker A:

We weren't trying to say do you have money to pay for paper?

Speaker A:

It's how is paper going to make your district run more effectively and efficiently?

Speaker A:

And I need to prove that to you.

Speaker A:

So for us it was about so that we were replace, in some cases we were replacing more traditional models of tutoring which might have been a few college students coming to public school that high school for six hours, three hours on a Tuesday, three hours on a Thursday.

Speaker A:

And we would come in and be not necessarily priced similarly.

Speaker A:

We were a pretty high ticket item.

Speaker A:

But we'd be like, well you're going to invest a little more, but you're getting 24,7 unlimited access to tutors and tutoring for your students.

Speaker A:

Plus we're going to train your teachers and we're going to build on our infrastructure, et cetera, et cetera.

Speaker A:

And the all of these districts had this problem where there was this huge disparity again between some students that would go home and mommy and daddy would pay for tutoring for them, private tutoring.

Speaker A:

And then they felt that they were failing the other students that couldn't afford that.

Speaker A:

So we were solving a huge problem for that district and they saw the value in investing a little more and getting an infinite amount more value from that dollar that they're spending.

Speaker A:

So it became a question about budget prioritization.

Speaker A:

And just like you alluded to, it's not about whether they do or don't have money.

Speaker C:

The market for this is going to be somewhat limited in Canada just because of the size of Canada.

Speaker C:

So have you found that your biggest market is in your southern neighbor?

Speaker A:

Absolutely.

Speaker A:

I mean it's very common for Canadian technology companies to quickly look south just because the market is more than 10 times bigger.

Speaker A:

I would say there's one in education which is generally in Canada.

Speaker A:

In the US and most of western world is very pretty risk averse industry.

Speaker A:

It's always slightly less risk averse in the US So we thought the combination of the market being much bigger plus a little bit less aversion to risk, we thought we could have really had an impact, and we did.

Speaker A:

So it's not like we avoided Canada.

Speaker A:

We've tried selling everywhere in Canada and the U.S.

Speaker A:

at the same time, which probably wasn't one of the mistakes that we made.

Speaker A:

We weren't focused enough.

Speaker A:

But we quickly started to get the momentum in Southern California, which in Irvine county and Laguna beach county, which were more affluent counties, which, from that mission perspective, we didn't feel like this was the best fit.

Speaker A:

But it really kickstarted us to understand how to sell districts.

Speaker A:

How do you run customer success?

Speaker A:

How do you make, deploy and make paper a success in a public school district?

Speaker A:

And then from there, you know, we quickly exploded elsewhere in California and then we started to get to other big markets like Florida, Nevada, Texas, New York, and sort of went very coastal just because those are where the bigger populations are.

Speaker A:

So, you know, us was a very big market for us and still is 99% of our market today.

Speaker B:

Hi.

Speaker B:

The podcast you are listening to is.

Speaker C:

A companion to my recent book, Tech Startup Toolkit how to Launch Strong and Exit Big.

Speaker B:

This is the book I wish I'd had as I was founding and running eight startups over 35 years.

Speaker B:

I tell the unvarnished truth about what.

Speaker C:

Went right and especially about what went wrong.

Speaker B:

You could get it from all the usual booksellers.

Speaker C:

I hope you like it.

Speaker C:

It's a true labor of love.

Speaker B:

Now back to the show.

Speaker C:

I imagine that you're, for a lot of reasons, you're going to focus on very large school districts.

Speaker C:

They have a bigger budget.

Speaker C:

It means that you're.

Speaker C:

You're having to worry about a smaller number of variations in the infrastructure.

Speaker C:

But to truly democratize, you really have to get to even some of the smaller, poor school districts.

Speaker C:

Is your model set up such that you can really see yourselves servicing those smaller school districts over time?

Speaker A:

Yeah, absolutely.

Speaker A:

I think our wheelhouse at the beginning wasn't the biggest districts.

Speaker A:

You're not going to go into, you know, Los Angeles Unified School District and say, hey, do you want to buy paper?

Speaker A:

You can't even get a meeting with any of the assistant superintendents.

Speaker A:

Forget about the superintendent.

Speaker A:

So our wheelhouse was in this range of districts which had about a thousand to fifty thousand students.

Speaker A:

And it was about 75% of the market of the public school districts in the US Are in this range.

Speaker A:

So what we felt was like the middle layer.

Speaker A:

Then there was a bunch of much smaller districts and then a few much larger districts.

Speaker A:

But for us, our wheelhouse at the start was this middle range where we felt we can not only make the biggest impact, but also fund and make enough money to fund the business.

Speaker A:

And that was our philosophy for the first few years once we were in market.

Speaker A:

So again,:

Speaker A:

2019, we started to grow pretty quickly.

Speaker A:

And then:

Speaker A:

And now everybody needed access to remote products and remote services in education because students were at home.

Speaker A:

So up until then, that middle layer was where that mid market is where we spent most of our time.

Speaker A:

But then obviously, as the pandemic comes in now, you know, we had the big districts coming to knock on our door and say, hey, I know you're working with the neighboring community and the neighboring school district.

Speaker A:

Can you help us?

Speaker A:

So then it started, you know, it, it, it sort of called us in a direction instead of us saying, hey, we're going to go after the big whale, primarily because it's, it's, it's hard to sell to the big whales.

Speaker A:

And especially when it's public money, public school district, very long sales cycles.

Speaker C:

I'm assuming this is a relationship selling kind of situation where you've, somebody's gotta call them.

Speaker C:

They're not gonna pick you out of a catalog or anything like that.

Speaker C:

So how can you scale?

Speaker B:

How, how have you managed to scale?

Speaker C:

Cause you have scaled quite a bit and in fact you've raised a lot of money.

Speaker A:

Yeah, right.

Speaker C:

Haven't you raised like 400 million?

Speaker A:

Yeah, we've raised close to 400 million.

Speaker A:

We did.

Speaker A:

So once the pandemic hit, we sort of, I guess, I don't know where it blew up.

Speaker A:

We, in the best way possible, not in a bad way.

Speaker A:

And we went some of just.

Speaker A:

And ideally we went from about 50,000 students on the platform at the beginning of the pandemic, and within two years we were above 3 million students and grew through thousands of employees, raised a ton of money.

Speaker A:

And obviously, how do you scale?

Speaker A:

It depends on what you're asking.

Speaker A:

Which part of the business had to scale?

Speaker A:

All of it had to scale, to be honest.

Speaker A:

And there is a lot of challenges along the way.

Speaker A:

And you know, there's challenges in every business.

Speaker A:

And post pandemic, there were challenges, but I think during that really rapid scaling phase, for those entrepreneurs that are listening to this, that are about to go through this or going through this, it's a bit hypothetical what I'm going to say, but the biggest challenge was knowing when to go fast versus when to go slow.

Speaker A:

So you end these high, high growth, high scale, fast moving Environments, you feel like you're making a million decisions a day and that's normal.

Speaker A:

Every entrepreneur does that.

Speaker A:

But there's going to be three or four of those decisions that you're going to make that are going to fundamentally change the course of the business.

Speaker A:

And maybe not every day, but it happens often enough.

Speaker A:

And what's important is for you to recognize which of those decisions need time because the return on investment on that decision is going to be 10x multiple.

Speaker A:

So it's knowing what decisions are the important ones and really giving yourself the time, which again, in a high scale environment is just all.

Speaker A:

Feels almost impossible.

Speaker A:

And I would say that, you know, I've made, I have tons of examples of mistakes that I've made in that, with, with that respect.

Speaker A:

But there were times when I knew we need to slow down here.

Speaker A:

This might take us a couple of weeks to come to a decision, but it's important that we take the time and it's really hard to do in a, you know, venture backed, high growth environment.

Speaker C:

Okay, so that was one message to entrepreneurs.

Speaker C:

Do you have any other messages that you feel like you just have to get out to entrepreneurs listening?

Speaker A:

Yeah, I think a really important message that I like to put out there the way companies, any company scales is when the people scale and your leaders, your employees, the people side of all of this is what I would consider the most important investment that you need to make.

Speaker A:

And frequently.

Speaker A:

And maybe people don't like to talk about it as much, but people do talk about it.

Speaker A:

I'm not saying I'm the first person here.

Speaker A:

We forget to invest as leaders and founders in yourself.

Speaker A:

We forget to.

Speaker A:

Or we quickly feel this Russian ego as you start to scale.

Speaker A:

But it's really, really important to invest in yourself because founders have a multiplier effect.

Speaker A:

They're cultural meters.

Speaker A:

So the more that you invest in yourself, the more you understand who you are as a leader and as a person, the more centered you are, the faster your business will grow because you will then be an example for all of your leaders of this type of leadership that we want at paper or whatever company.

Speaker A:

And then they become these cultural leaders.

Speaker A:

And as companies scale and everyone knows the culture which is so ingrained in the founders starts to dissipate because you just, your, your tentacles can't reach out that far into the org.

Speaker A:

So it's really important for you to under.

Speaker A:

Culture is, it's, it's just, it's there.

Speaker A:

You don't choose what your culture is.

Speaker A:

It just, it is what it is.

Speaker A:

But it's really important is for.

Speaker A:

To define that culture, for everybody to understand.

Speaker A:

And the culture is from the founders.

Speaker A:

And again, the more you understand yourself as a leader, the clearer that culture becomes to everybody.

Speaker A:

So really my message is don't be shy, to invest in yourself.

Speaker A:

Take the time you need to learn about yourself and who you are as leader.

Speaker A:

It's fundamental.

Speaker A:

It's where all the breakthroughs happen and give your team and your leaders the same space to do that as well.

Speaker C:

You, like every other startup founder, is full of grit.

Speaker C:

The good kind of grit.

Speaker C:

Good grit.

Speaker C:

Where does yours come from?

Speaker C:

Where do you think it came from?

Speaker A:

Wow, that's an incredible question that I've never been asked before.

Speaker A:

I love this.

Speaker A:

I love this question.

Speaker A:

Where does it come from?

Speaker A:

I can tell you that I.

Speaker A:

I know that I'm very competitive.

Speaker A:

There's no doubt, but I can't tell you exactly why I'm so competitive.

Speaker A:

It's.

Speaker A:

I don't feel like I have a chip on my shoulder.

Speaker A:

So it's.

Speaker A:

The grip doesn't come from there.

Speaker A:

I don't feel like I need to prove anything to anybody.

Speaker A:

I think for me, what just really matters is, especially with paper, this might be like a cheesy answer, but it's very sincere.

Speaker A:

I really cared about the impact we were having on students, but I felt like I was fighting for them.

Speaker A:

That grit came from me not wanting to back down and fight for those students.

Speaker A:

If I look back at my own education and when I was a student, I did okay.

Speaker A:

I didn't struggle, but I wasn't a plus student.

Speaker A:

But I always felt supported.

Speaker A:

I felt supported by my parents, by my teachers, and I felt that because I felt that support.

Speaker A:

That support.

Speaker A:

My parents didn't sit down with me, do my homework.

Speaker A:

You know, they.

Speaker A:

I had to figure it out for myself.

Speaker A:

But just on the fact that I know that I was supported, I think that it was really.

Speaker A:

It really benefited me during school.

Speaker A:

And I think when I started paper, I saw, like, if I can give that back to students, that even if that support came from the form of a tutor or a coach or a mentor, then I felt I just owed it.

Speaker A:

I owed it to other people because I was so lucky to have that.

Speaker A:

So that's for me, where the grit came from, especially with regards to paper when competitive.

Speaker A:

When I'm playing my amateur soccer game on a Friday night, I can't tell you I would have to dig into that one.

Speaker A:

But I'm competitive across the board.

Speaker A:

But I know the grit with.

Speaker A:

With specific web paper came from this idea that I just wanted to give back this, this feeling of, of support that I had.

Speaker C:

I wouldn't be surprised if it comes out of your deep in your background as well when you say, I don't know why I'm competitive, that, that probably is an indication that it's in there very deep.

Speaker C:

How big is paper now?

Speaker C:

How many employees is it?

Speaker A:

So we're obviously, our tutors are still our employees and have always been employees of the company.

Speaker A:

So we're probably around a thousand employees or something like that coming out of the pandemic.

Speaker A:

Like a lot of technology companies, there's a bit of a mark to reset.

Speaker A:

So, you know, we unfortunately did go through a couple of layoffs and those are never fun, specifically for the people that are impacted.

Speaker A:

But I didn't talk much about what specifically we do.

Speaker A:

We offer tutoring.

Speaker A:

For the majority of tabor's existence, we provided what we call on demand tutoring, which was just through chat.

Speaker A:

A student comes online, they're stuck with their math homework, they pop it in the chat, they go back and forth.

Speaker A:

But what we recognized was over the last, throughout the pandemic, it still didn't help serve the students that needed it most because they were just discouraged.

Speaker A:

They didn't even care to go onto paper.

Speaker A:

Like, why am I going to Wechel?

Speaker A:

Who cares?

Speaker A:

Nobody cares about me.

Speaker A:

So we launched a new product called Growth.

Speaker A:

And I'm not here to push the new product, I feel like, but it's just as important to the story of where we are today, which is this.

Speaker A:

It's a slight impact tutoring where students can get one on one support from the same tutor through a video multiple times a week.

Speaker A:

And we have a pre assessment, a post assessment.

Speaker A:

We can see their growth.

Speaker A:

And I just feel we're really going, in my opinion, even further into the mission of supporting the students that need it most.

Speaker A:

So it's something that I've been really excited about and yeah, I'm looking forward to seeing what, what the company does over the next, over the next few years as we launch into this new secondary product, or not secondary, the second big product, I should say, for the company.

Speaker C:

A lot of your people are, I'm assuming, like distributed far and wide.

Speaker C:

So the core group, do you have them working remotely or do you have an office or how's that work?

Speaker A:

Yeah, so we grew up during the pandemic.

Speaker A:

Uh, so what did that mean?

Speaker A:

employees when in March:

Speaker A:

And then we had a satellite office in Los Angeles.

Speaker A:

Because we had again, customers, a lot of customers in Southern California.

Speaker A:

Um, and then once it started to grow very quickly, we just decided we're going to be a distributed remote company that employs people in the US Or Canada.

Speaker A:

And that's sort of what we are.

Speaker A:

So we're a remote company.

Speaker A:

I say we are because paper is so close to my heart.

Speaker A:

But I do want to just clarify that over the last six months I've also taken a little bit of a step back with a company and we do have a fantastic new CEO in role over the last few months.

Speaker A:

And so I feel a bit, I don't want to use the word uncomfortable, but it's, it's we meaning my company and the company that I founded.

Speaker A:

But it's no longer just mine.

Speaker A:

It's like my, my kid is old enough now that they moved out and they, they take care of themselves.

Speaker A:

So.

Speaker A:

Yeah.

Speaker C:

Have you kept a board seat?

Speaker C:

Are you on the board?

Speaker A:

Yeah, on the board seat.

Speaker A:

I'm still very involved, you know, advisor as well and help them out.

Speaker A:

It's like the idea of, you know, my kids no longer home, like I said, and they, they need help moving and they'll call me.

Speaker A:

I'm like, yep, I'm there.

Speaker A:

When do you need me?

Speaker A:

So it's been a nice transition for me and I felt it was a good opportunity to get fresh eyes in over the last few months.

Speaker A:

So I feel a little bit irresponsible saying we, although it is still we and us and me.

Speaker A:

But it's, it's a lot of other people involved.

Speaker A:

So I just want to be sure that I'm giving other people their credit.

Speaker C:

Listen, thank you very much for this enlightening exposition on your company and your journey and also telling us a little bit about your grit.

Speaker B:

Appreciate all of it.

Speaker A:

Appreciate it very much.

Speaker A:

And thanks for having me.

Speaker A:

This is a lot of fun.

Speaker B:

And here's your founder's toolkit from today's conversation with Roberto Chase the problem, not the olution.

Speaker B:

Roberto spent four years deeply understanding the.

Speaker C:

Education access problem before finding product market fit.

Speaker B:

Focus on truly understanding your customers pain points before locking in your solution.

Speaker B:

Know when to slow down during scaling in high growth environments.

Speaker B:

Identify the three to four decisions that will fundamentally change your business trajectory and give yourself time to make them thoughtfully.

Speaker B:

Even when everything else feels urgent.

Speaker B:

Invest in yourself to multiply your impact as a founder.

Speaker B:

Your personal growth has a multiplier effect on your entire organization.

Speaker B:

Take time to understand your leadership style and who you are.

Speaker B:

It directly shapes your company's culture and success.

Speaker B:

Reframe Budget Conversations Instead of asking if customers have money, show how your solution makes their existing budget work harder.

Speaker B:

Roberto succeeded by demonstrating how paper could deliver infinite value compared to traditional tutoring alternatives.

Speaker B:

Remember, true grit comes from having a mission that matters to you personally.

Speaker B:

Find what fuels your competitive drive and let it power you through the inevitable challenges of building something extraordinary.

Speaker B:

The show notes contain useful resources and links.

Speaker B:

Please follow and rate us@podchaser.com designing successful startups.

Speaker B:

Also, please share and like us on your social media channels.

Speaker C:

This is Jothi Rosenberg saying TTFN Tata for now.

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