She Raised $175 Million To Build A Platform That Provides Universal Accessibility To Email, Calendar, And Contacts Providers With A Single Integration

Building a successful company is rarely a linear journey. For Christine Spang, co-founder and CTO of Nylas, the journey has been marked by significant pivots, bold decisions, and relentless perseverance when scaling the business and raising capital.

From an early fascination with open-source software to raising $175M for her startup, Christine’s story offers invaluable lessons to aspiring entrepreneurs on the core principles of culture and navigating the startup ecosystem for over 11 years and counting.

In this engrossing interview, Christine shares insights into being a part of a fantastic startup tool straight out of MIT, which ended up getting acquired by Oracle. And the path leading to building Nylas, her latest venture.

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

The Early Days of Memory Management, Pointers, and Linux

Born in Scarborough, Canada, Christine’s journey took her to upstate New York at the age of three. Though she grew up in the U.S., she still fondly remembers childhood trips back to Canada. Her father, an electrical engineer, moved the family for a job at Welch Allyn, a medical device company.

This upbringing, filled with backyard adventures and a love for science, set the stage for her future in engineering. In high school, Christine discovered open-source software, a turning point that led her deeper into the world of computer science.

Christine was keenly interested in science and math and wanted to be an engineer to build things. Her perception of engineering was super broad and comprised of sitting at a computer and creating things from bytes. She loved to read books on sci-fi and fantasy and craved adventure.

Christine’s interest in programming was sparked by text-based online adventure games known as multi-user dungeons (MUDs). Players had to create a character in the world they wanted to explore.

Since Christine wanted to create her own story, she gravitated towards a game with the fewest constraints possible. She got into the Lord of the Rings MUD and started helping run it. She wanted to customize the gaming experience, which required learning C programming.

At 15, Christine dived into reading the classic book of programming called A Book on C. She recalls reading the pointer section over and over again with the goal of making changes in the game. She also connected with other people, asking questions to refine her understanding.

Christine’s persistence in mastering complex concepts, like memory management and pointers, set the foundation for her technical expertise. She also installed Linux into the family computer since the game only ran on Linux, eventually contributing to the actual Linux operating system.

From Canada to MIT

Christine’s passion for open-source software ultimately led her to MIT, a place she once thought was out of her league. Encouraged by mentors and inspired by the movie Good Will Hunting and Matt Damon’s character, she took a chance and applied. To her surprise, she got in.

At MIT, Christine found her tribe—brilliant, like-minded people who thrived on innovation. But it was also an intense environment where everyone had been the most intelligent person in their high school. The rigorous coursework pushed her to grow both technically and personally.

Christine’s first taste of the startup world came through Ksplice, an MIT-founded company that allowed Linux kernel updates without rebooting. She initially joined as an intern, later accepting a full-time role instead of pursuing a master’s degree.

Ksplice: First Foray into Startups

Ksplice was a bootstrapped company with no venture funding, operating scrappily out of the founders’ house in Cambridge, Massachusetts. The founders–Jeff Arnold, Timothy Abbott, Waseem Daher, and Anders Kaseorg, used their graduate thesis to build the company.

They commercialized it in a security update service for any computer running Linux. Their product-market fit was among web hosts and VPSs who would use this service to keep their machines up-to-date in a timely fashion.

Christine noted they had a patch for most hacking incidents that hadn’t been applied yet. She had been sponsoring software uploads to Debbie Linux for one of the founders, and when he offered her an internship, she jumped at it.

This experience provided Christine with a crash course in running a business. She recalls they had servers running in the basement and cables running to each floor for enough power for the build servers in the basement.

Christine also recalls learning to hire salespeople and understanding the nuances of bootstrapped growth. The founders were confident they could double the current business but were unsure about a 10x or 1000x exit.

The startup’s rapid success led to an acquisition by Oracle within a couple of years. While some viewed it as an early exit, for Christine, it was a transformative experience that exposed her to the full lifecycle of a startup—from inception to acquisition.

Building Nylas: Raising Capital and Pivots

After Ksplice was acquired, its founders offered Christine the opportunity to join their next venture. Instead, at 24, she joined hands with a friend and moved to Boston. It was 2013, and at the time, the Silicon Valley buzz was very intense.

Christine co-founded Nylas, a platform focused on email and communication APIs. As she explains, the idea was to overcome the technical barriers that prevented access to the valuable data locked in emails, minutes of meetings, and internal communication within a workplace.

Christine and her team wanted to connect the written information in the context of a business and work with applications that could refine the information and eliminate vague, hard-to-understand terms.

Christine recalls how they did some PR and released the first version of the API infrastructure they had built as an open-source product.

Initially, they released the product on GitHub and published an article on Hacker News, the website from which many software developers sourced their information. They also got an article on TechCrunch, which garnered immense engagement.

Essentially, the company’s initial idea was a productivity-focused email client, but after realizing the limitations of that market, they pivoted toward building an API developer infrastructure for email.

From Vision to Pivot: Finding What Works

Nylas set out to help developers build great user experiences in their apps by offering seamless integration with communications data. Initially, the company spent four years building its core infrastructure and also developed a desktop app.

However, the app faced high churn rates and proved unsustainable. Recognizing the financial strain, Christine and her team made a tough but necessary decision to shut down the app and pivot toward the API infrastructure that had powered it.

Today, that infrastructure enables developers to integrate email, calendar, and other communications data into their applications, helping them drive engagement and enhance user experiences.

This shift was crucial—it aligned the company with a broader market need and positioned Nylas for significant growth.

The Nylas Business Model: API Infrastructure as a Service

Like Stripe or Plaid, Nylas operates as an API infrastructure company, bridging applications and low-level cloud-based communications data providers.

By offering pre-built integrations and customizable user experience components, Nylas allows developers to focus on differentiating their apps instead of spending time on backend connectivity.

Companies use Nylas to embed scheduling, sync contacts, and access email and calendar data—critical functionalities for CRM and business productivity apps. Companies can go to market quickly thanks to the infrastructure that enables them to build a competitive app.

With the rise of AI-driven applications, Nylas has become even more valuable, providing the necessary contextual data to power intelligent workflows. As Christine explains, Nylas is like a middleware layer that accelerates people’s development so that they have less operational load over time.

The company’s revenue model is usage-based, billing customers monthly based on the number of accounts connected to its platform. Nylas is a self-serve model where users can sign up and start paying $30 a month to get the full power of the platform.

This approach fosters long-term partnerships as customers scale their usage over time, making Nylas an essential part of their application stack. Christine explains that the product is very sticky because people power the core functionality of their applications through Nylas platform.

Users can keep up with the evolving software world and the many demands on application developers, who can connect to different data sources. Nylas adapts to changing expectations and needs as upcoming generations of applications quickly replace older generations.

Nylas provides the Lego blocks to app developers so that they can keep pace and focus on the differentiator and what their core customer base needs.

Raising Funding for Nylas

Fundraising played a significant role in scaling Nylas. Over the years, Christine and her team successfully raised $175M, which required persistence, strategic storytelling, and navigating investor relationships.

Nylas started out with a $2M seed round. Its last series C round was in 2021 when the company raised $115M. Christine reflects on how investor expectations evolve at different stages.

In 2013, during the zero-interest rate period, early-stage investors were more flexible, funding promising ideas without significant traction. Today, however, seed investors expect concrete traction.

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By the time a company reaches Series A, it must demonstrate product demand and a capable team. At later stages, the focus shifts to financial metrics, growth rate, and capital deployment strategy. Christine quickly learned how to customize the pitch according to the investor audience.

One crucial lesson Christine learned is that maximizing valuation isn’t always the best path. Instead, founders should focus on raising the right amount of capital to execute their vision while maintaining flexibility.

In the past, startups often raised funds just to reach the next round, but today, the goal is increasingly to achieve self-sustainability, making future fundraising optional rather than necessary.

One of the key lessons she learned was the importance of picking investors who align with the company’s vision and long-term goals.

The Art of Fundraising: Strategy and Execution

Christine likens fundraising to a sales process. Every round required meticulous preparation, tracking potential investors in a CRM-like spreadsheet.

The team categorized investors into different tranches, first pitching to those they felt comfortable with to refine their messaging before approaching top-tier investors. Creating a sense of competition among investors helped maximize outcomes.

Another key takeaway is that fundraising is not just about technology; it’s a business pitch. While early-stage investors may focus on product potential, later-stage investors prioritize revenue growth, scalability, and operational efficiency.

Founders must tailor their pitch accordingly, ensuring they clearly communicate the business opportunity.

Building for the Future: The Vision Behind Nylas

At its core, Nylas aims to enhance productivity by modernizing business workflows. Early on, the company enabled CRM platforms to integrate email data seamlessly, replacing outdated manual processes like BCC’ing special addresses.

Today, Nylas continues to drive innovation by ensuring business applications are intelligent, automated, and efficient. The company’s mission extends beyond software—it’s about giving people more time to focus on meaningful work rather than manual data entry.

By providing robust API infrastructure, Nylas empowers developers to build the next generation of applications that meet ever-changing user expectations.

Advice to Founders: Trust Yourself and Take Risks

Reflecting on her journey, Christine shares an essential piece of advice: trust yourself. As a founder, you have more agency and influence than you might realize. People join startups because they believe in the vision and the team behind it.

Instead of constantly doubting yourself, embrace the learning process, take risks, and confidently make decisions. Mistakes are inevitable but are also part of the journey toward building something truly impactful.

Final Thoughts

Christine Spang’s story is about curiosity, ambition, and perseverance, from her teenage obsession with MUDs to leading a high-growth startup. Her experiences highlight the realities of startup life—the highs, the pivots, and the strategic decisions that drive success.

Nylas’ journey—from product pivots to strategic fundraising—highlights the resilience and adaptability required to build a lasting business. Her journey offers a roadmap filled with insights and inspiration for anyone looking to build and scale a company.

Listen to the full podcast episode to know more, including:

• Christine’s journey shows that mastering complex concepts early on, like memory management and open-source software, laid the foundation for her technical expertise and entrepreneurial success.
• Nylas started as a productivity-focused email client but pivoted to an API infrastructure model, demonstrating the importance of adapting to market needs.
• Raising $175M required not just a great product but also strategic storytelling, investor alignment, and treating fundraising like a sales pipeline.
• Christine emphasizes that raising the right amount of capital for sustainable growth is more important than chasing the highest valuation.
• Early startup experiences at Ksplice gave Christine firsthand insights into bootstrapping, hiring, and navigating acquisitions—knowledge she applied when building Nylas.
• Nylas’ business model highlights how API infrastructure enables developers to build faster, integrate more efficiently, and scale their applications seamlessly.
• Christine’s advice to founders is to embrace uncertainty, take risks, and recognize their own agency in shaping the startup’s vision and success.

 

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