Neil Patel

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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.

In a recent interview with Roberto, we delved into the captivating narrative of their rise, highlighting the pivotal moments, challenges faced, and lessons learned along the way.

Listen to the full podcast episode and review the transcript here.

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A Journey Rooted in Education and Determination

Roberto Cipriani’s upbringing as the son of Italian immigrants in Canada laid the foundation for his unwavering belief in the transformative power of education.

Instilled with the value of hard work and perseverance by his parents, Roberto embarked on an academic journey that eventually led him to McGill University.

Initially drawn to academia and physiology, his passion for technology began to emerge during his graduate studies in computational neuroscience, where he found fulfillment in solving complex problems through code.

Roberto recalls how his original plan was to complete his Ph.D. and then complete the post-doctorate before starting his own lab.

He quickly found himself developing extensive programming skills and doing tons of data analysis and data science. Instead of grad school, Roberto opted for a career in technology.

Roberto became a freelance software developer and started working with small to medium-sized businesses, primarily based in Montreal. These clients needed technology to build web apps or other software on the backend.

From Freelancer to Entrepreneur: The Genesis of Paper

Roberto’s path intersected with Phil Cutler, his future co-founder, through an introduction facilitated by a mutual friend. Phil had a local in-home tutoring company in Montreal. Their collaboration initially revolved around leveraging technology to scale Phil’s local tutoring business.

Phil’s business model was simple. If a parent needed a tutor for their child, they could call a number and have a tutor show up at their home. Phil contacted Roberto because he needed to build some technology to help scale the business.

However, it was during this partnership that the seeds of a revolutionary idea began to sprout – using technology to bridge the educational inequities that exist throughout the education system.

Recognizing the potential impact of their vision, Roberto and Phil embarked on a journey to establish Paper.

The duo was driven by a mission to make academic support accessible to all students, particularly underrepresented students who did not have access to academic support outside of school.

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Pivots, Persistence, and Listening to Customers

As with any startup, Paper encountered numerous pivots and challenges along the way. Roberto and Phil started out trying to take the offline in-home experience and bring it online to make it scalable.

This was doable since tutors didn’t have to travel to see their students; they could do it from the comfort of their homes, making it more accessible.

Shifting their focus from video to chat-based tutoring to optimize their strategy, each decision was guided by a deep understanding of their customers’ needs.

Sometime in 2014, before video conferencing became popular, Roberto and Phil built an online classroom with video conferencing and a collaborative whiteboard with file sharing. The goal was to recreate that in-home experience online.

Roberto emphasized the importance of listening closely to feedback, iterating rapidly, and remaining resilient in the face of adversity.

When they pivoted from video to chat in 2015. Paper steadily gained traction in the competitive ed-tech landscape through relentless perseverance and a commitment to its mission.

The Paper Business Model

Before the pandemic, Paper was best known as a virtual tutoring company. In the past two years, the company has experienced an extensive period of product growth, transforming Paper into a comprehensive, personalized learning platform used by over three million students across 40 U.S. states and Canada.

Today, Paper is a comprehensive, personalized learning platform that empowers all students, offering on-demand academic support, independent practice tools, 24/7 tutoring, feedback on written work, career and college readiness guidance, and more.

The support is marketed to school districts that directly purchase access for their students.

Roberto and Phil are committed to understanding what their customer wants. With every tutoring session, they ask students questions about their experiences and how the session could have been improved.

As Roberto says, “It’s all about time in market and being as close to the customer as possible.”

However, he also concedes that there are many challenges they face, mainly because the customer is the school district, but ultimately, the end user is the student.

Their unique selling point is listening to users, not with the presumption of what they want, but actually allowing them to share how the company can better support them and their evolving needs.

They keep in mind that as the needs of students continue to change with society, so will the service offerings they provide them with. It’s essential for them to create a space where students feel comfortable about sharing what they actually need.

They take that information, filter it, and give it back to the teams so they can build what’s suitable for the users.

Roberto talks about how they realized early on that to succeed in their mission; they would have to sell directly to public school districts if they truly wanted to bridge the equity gaps.

Seizing Opportunities Amidst Adversity: The Impact of COVID-19

Even before the pandemic started, district leaders had understood how important it is to embed technology in their district properly. By March 2020,

65% of students in the US had access to a device through their school.

The onset of the COVID-19 pandemic brought unforeseen challenges but also catalyzed opportunities for Paper. As schools rapidly adopted technology to facilitate remote learning, the demand for digital educational solutions soared.

To continue supporting students through this immense change to their learning structure, schools needed to ensure that all of their students had access to a device.

In the first three months of the pandemic, the number of students using devices soared to 95%. By the end of 2020, about 99% of students had access to a device through their school.

That’s how they could then access the technology, software, and services that were going to support their academic journey. This investment in technology and infrastructure became an integral springboard for Paper’s success.

Paper’s platform, designed to provide academic support seamlessly online, became increasingly indispensable. Leveraging this momentum, Paper expanded its reach, ultimately aligning with over 99% of students across various school districts in the U.S.

Navigating the Fundraising Landscape: Lessons Learned

Roberto reflected on Paper’s fundraising journey, acknowledging the arduous process of securing investment, particularly in the early stages. Facing skepticism about the viability of ed-tech ventures, Roberto and Phil persisted, pitching to numerous investors until finding the right fit.

He emphasized the importance of storytelling, discipline, and networking in navigating the fundraising landscape effectively.

Moreover, Roberto underscored the value of surrounding oneself with individuals who complement one’s strengths but share the core values, enabling accelerated growth and innovation.

Eventually, Roberto and Phil raised more than $380M for the company. He remembers pitching the venture to 125 different friends and getting support from one friend who contributed significantly to the company’s continued success.

Storytelling is everything, which is something that Roberto Cipriani was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend Peter Thiel (see it here), where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

The long sales cycle, aligned with the academic calendar, made getting into the districts and institutions challenging. But, once they started to get more and more proof points, selling to public school districts became easier. As a result, fundraising became easier.

Roberto talks about an effective strategy they adopted. Regardless of the VC, they were talking to, they would confirm the next steps at the end of every meeting. This process gave them a lot of clarity on aligning expectations.

Networking and being involved in the startup communities wherever you’re based to make sure that you know the right people is also crucial. These people can introduce you to the other people and the other VCs. Ultimately, the key is to get the process right and be disciplined in your approach.

With its combination of human support and scalable technology, Paper has become a valuable tool that helps equip students with personalized learning support to maximize their outcomes.

Whether they are struggling with a question to complete their homework the night before it needs to be submitted. Or writing their college application. The mission is to support students and really bridge the gap between what schools provide and what students need to succeed.

Words of Wisdom: Perseverance and Continuous Learning

In closing, Roberto shared invaluable insights gleaned from Paper’s journey. He emphasized the significance of perseverance in overcoming obstacles and the necessity of embracing continuous learning.

Roberto’s advice should resonate deeply with aspiring entrepreneurs, highlighting the importance of listening to one’s intuition, recognizing areas of improvement, and fostering a culture of adaptability within organizations.

Conclusion: A Testament to Resilience and Innovation

The story of Paper serves as a testament to the resilience and innovation inherent in the startup ecosystem.

Through unwavering determination, a commitment to their mission, and a relentless pursuit of excellence, Roberto Cipriani and his team have not only transformed educational access but also inspired countless individuals to dream big and make a difference.

As Paper continues to chart new territories in the realm of ed-tech, its journey stands as a beacon of potential in a world craving equitable educational opportunities.

  • 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.



For a winning deck, see the commentary on a pitch deck from an Uber competitor that has raised over $400M (see it here). 

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Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.


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Neil Patel

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

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