The Heart of the Problem: Alumni Feature on Jessica Murphy ’00, Co-Founder and Chief Customer Officer of True Fit

The Heart of the Problem: Alumni Feature on Jessica Murphy ’00, Co-Founder and Chief Customer Officer of True Fit

Image courtesy of True Fit

Jessica Murphy ’00, co-founder and chief customer officer of True Fit, discusses pitfalls and pure entrepreneurial joy with B-Lab 2019 cohort

Jessica Murphy ’00 spends most of her time racing from airport to airport on her way to solve problems on a global scale for True Fit Corporation. Understandable, considering the company boasts offices from Boston to London to Mumbai. 

True Fit began as an idea during Murphy’s time as an MBA candidate at Babson College, prior to which she studied international commerce at Brown and spent a few years’ stint as a buyer for Filene’s (the department store later succeeded by Macy’s). After enough time on the work force and in business school, Murphy was ready to go “all-in” with True Fit. She threw everything she had at the idea — including $5,000 in repurposed student loans — and chose to forgo the typical post-MBA route. 

It paid off. True Fit came into its own as one of the first data platforms for enhancing style and comfort in the retail clothing experience. Most recently, it secured a Series C round of funding for $60 million, no doubt due to Murphy’s combination of business acumen and pure grit. 

Murphy visited the Nelson Center’s new Thayer Street building last week to deliver the keynote presentation to this summer’s Breakthrough Lab cohort on the opening day of the program. 

Her extensive technical knowledge was evident as she fielded questions encompassing everything from the viability of startups in nascent markets, to evolving your solution through countless iterations. Yet the key takeaway of Murphy’s presentation was what appears to be the secret to her success: a seemingly innate understanding of the emotional workings of both consumer and employee. 

“What is that pain point you’ll be focusing on?” she asked the audience of young venture founders. The pain point. The issue that ruins your customer’s whole day. The heart of the consumer’s problem that you can’t lose sight of. 

The pain point at the center of True Fit after all these years? To “help people find clothes and shoes they’ll love and keep.” It’s a broad stroke mission statement that speaks to how shoppers’ self-image is affected by the struggle to fit into inconsistent, unrealistic sizing. Perhaps it’s this human desire for affirmation, granted by True Fit, that has enabled it to grow to its current user base of over 100 million worldwide. 

Jessica Murphy ’00 with our 2019 Breakthrough Lab cohort

“I’m here to be transparent with you,” assured Murphy. And that she was. Moving on from her self-described “brag slides” that list the impressive numbers behind True Fit, Murphy described both joyous accomplishments and dark days as a leader responsible for the livelihoods of hundreds of employees. “It had to work,” she stated. “I had no choice.” From forgoing a salary for years to the challenges of attracting early investors for survival, there was no hardship of the entrepreneurial lifestyle that could not be broached. As a result, Murphy’s audience hung onto every word, eager for more of her candor. 

In response to one B-Lab founder’s question, Murphy transitioned to personal challenges. She discussed the culture shock of arriving at Brown, feeling unprepared coming from a single-parent household, often moving from apartment to apartment while growing up in a blue-collar Massachusetts town. Today, these difficulties serve as reminders of where her family came from — something deeply embedded in the fabric of True Fit. Murphy shared, for instance, that her sales presentations to retailers often begin with a photograph of her grandfather who migrated from Colombia to Central Falls, Rhode Island, to work as a loom repairman. Her anecdote illustrates a lineage of builders adept at piecing solutions together — whether that solution is a piece of machinery or a way of reimagining the modern fitting room experience. 

Murphy also keeps her immediate family close amidst the ever-present puzzle of work-life balance, another hurdle for entrepreneurs she touched upon. She lovingly refers to her husband (then-boyfriend) as her “first angel investor,” and jokes, “True Fit is my first baby. And then I had three real ones.” When asked what will come after her first brain child, Murphy said, “After True Fit’s eventual end… I will never not be an entrepreneur. It’s just too fun.”

2019 MAY SAN FRANCISCO SYNAPSE TRIP RECAP: From Slack to Robinhood to Learning from Alumni Entrepreneurial Leaders

2019 MAY SAN FRANCISCO SYNAPSE TRIP RECAP: From Slack to Robinhood to Learning from Alumni Entrepreneurial Leaders

This past May, the Nelson Center for Entrepreneurship and Brown Entrepreneurship Program (EP) took 9 students on an immersive Synapse trip to explore the startup culture in San Francisco, CA. The five-day, all-expenses-paid trip was made possible through the generosity of Brown alumni. The trip provided students with the opportunity to visit companies that encompass a wide spectrum of entrepreneurial activity, as well as time to explore the city and its rich history.

The goal of the trip is to help students expand their professional networks and learn nuanced perspectives from founders throughout the Bay Area and Silicon Valley. Jonathan Speed ‘84 welcomed the cohort over dinner before their immersion days to provide them a unique perspective on the startup scene in San Francisco. Speed’s career spans decades of innovation in the tech and startup space, from founding a SaaS company to leading companies as a CFO, and of course, advising dozens of startups. He is currently the CFO and VP of Operations at Versal Group, an eLearning technology company. His stories and their discussion helped the cohort gain a better understanding of the day-to-day life of the global center for high technology, innovation, and social media. The students felt prepared to embark the next day, to meet impressive alumni and industry leaders making changes in the SF ecosystem.

On Monday, May 20, students sat down for an intimate discussion on how the world can manage identity and access with Greg Kidd ’81, co-founder and CEO of globaliD and a generous donor for the trip. After, the cohort walked over to Y Combinator and had a conversation with Kat Manalac, a partner at YC, about the support structure they provide for each YC cohort, and learned that 70% of startups that go through Y Combinator succeed! By lunchtime they were riding an elevator with the CEO of Slack on their way to chat with Fareed Mosavat ’01, Director of Product Lifecycle, and Zindzi McCormick ‘09, Group Product Manager, about Slack’s growth and the company’s next steps in this time of rapid growth. The last stop on Monday was Yerdle, co-founded by Adam Werbach ‘95, where they sat down with co-founder Andy Ruben to chat about how Yerdle is redefining the future of retail and how brands can best serve their customers as well as the environment. His story of grit and resilience was not only inspiring but also a truly authentic look into the life of a founder.

They ended the jam-packed day with a lively alumni dinner, filled with stories, laughter, and new friendships. The night served as a powerful reminder of the incredible network of Brown alumni who have used everything they learned on College Hill and beyond to make impactful change in the world.

On Tuesday, the students headed to Palo Alto, where they started the day with Lauren Kolodny ‘08, partner at Aspect Ventures, a venture capital firm started by Theresia Gouw ‘90. Lauren brought along two other colleagues at the firm to discuss venture capital as a career path and provide examples of the type of experience VC firms look for when hiring. The cohort then made its way to Robinhood, a financial services company, where students first met with Alvin Hui, who leads university recruiting and programs. He provided a grand tour of the space and then introduced Nili Moghaddam ‘99, Associate General Counsel and Head of Litigation and Investigations at the company who explained her dynamic career path before Robinhood, and the reasons she was drawn to working at a startup. The group also chatted with her about the recent acquisition of MarketSnacks (now called Robinhood Snacks), co-founded by Nick Martell ’11. Nili was the lawyer who helped launch Robinhood Snacks.

The students ended the trip with a visit to Stanford University, where they discussed identity, social innovation, and representation in the field of entrepreneurship with Fern Mandelbaum ‘84, Lecturer in Management at Stanford’s school of business and Managing Partner at Vista Venture Partners. It was a whirlwind of a trip, but one that the students and alumni will never forget. Our immersive, educational, and life-changing Synapse trips from Barcelona, to London, to SF, are possible due to the generosity of alumni donors. We thank them for continuing to support entrepreneurial endeavors that take students off of College Hill and transport them to new cities and startup ecosystems.

If you are interested in getting involved please email us at Continue reading to learn more from the cohort and their own reflections on the trip.



Karina Bao ‘21, Applied Mathematics/Computer Science

The spirit of Brown alumni in San Francisco is incredible. They don’t accept the status quo. They think about the big picture; the whole system.

Through our conversations, I realized it was more important to build innovatively towards an ideal world than to agonize through every social problem. The conversations with students also helped and encouraged me to believe that sustainable and realistic solutions are possible; it just takes our willpower and teamwork.

At our first meeting with Greg Kidd ‘81, he shared the serendipity of the early days of his startups, Twitter, and his exciting vision for the future through globaliD. It was completely outside the realm of anything I’d ever thought about. And as we continued discussing, although it might seem futuristic, it was completely possible at a large scale. Consequently, my biggest takeaway was his message about solving problems. He said that if you’re solving a big enough problem, there’s no way it won’t be profitable. In other words, don’t necessarily worry about profitability, but focus on understanding the problem, building the solution, and profit will reveal itself.

That afternoon, we visited Yerdle, a clothing recycling company. Andy was extremely open about sharing how the company had 2 major reorganizations while holding the same principles. Now, they had stumbled upon the future for retail and could tell they were ahead of the curve in the service they were providing. It was great to hear about their highs and lows and visit the warehouse to see the inner workings.

During our final stop, Fern Mandelbaum emphasized the importance of bringing people from different backgrounds to the team. She highlighted how every new team member added should be different from the previous members. “If the first 3 people on your team are Brown students, the next should be someone not from Brown or not a student.” Her advice was concrete and straightforward to implement. She pressed that team members should have complementary skill sets instead of similar ones. She also shared stories about her friends who had guest lectured at Stanford like Haben Girma who have taught so much to her students.

Some of my other highlights were saying hello to Michael Seibel in the YCombinator lobby and sharing with him some of the progress I had made since meeting him at HackMIT last fall. Zindzi and Fareed at Slack shared how, “communication is only over when you are heard, not when you are done talking”. And Aerin Lim, an amazing role model from Silicon Valley Bank, shared how excited she was about new tech. Again, I feel enormously optimistic after this trip. The alumni were so warm, welcoming, and eager to share their advice and time. It really makes me excited to become an alum and give back.


Emily Wanderer AM ‘19, Entrepreneurship, Organizations and Social Justice

As a recent master’s graduate of an integrative studies program focused on Entrepreneurship, Organizations and Social Justice, my objective was to understand how I fit into the tech ecosystem in the Bay Area. The stark inequalities amongst San Francisco blocks were palpable. During the trip, I consistently asked about the social impact that the business’ considered. This provided us insight into the city and its inner workings but also how I could position my career to support social equity through tech companies.

A highlight for me was visiting Yerdle Recommerce, who is expanding quickly in their Palo Alto location now employing more than 70 individuals. Meeting the founder gave us a window into the evolution of the business both past and future, from a direct-to-customer reseller to a white label platform. Yerdle has succeeded by using the lean startup approach to find product/market fit before scaling an idea. Now that they’ve validated their idea, they will quickly scale their team and partnerships with brands. It was amazing to see how a small startup could influence an entire industry to shift their assumptions about what creates revenue.

Moving to a new city can be intimidating. I have now moved from Rhode Island to the Bay Area to pursue a career in for-profit social enterprise. As a direct result of the Synapse trip, I already have 7+ meetings set up including with Robinhood, Yerdle, and alumni.

Just this small start in building relationships and networks in a new place eases my fears tremendously. This trip catalyzed so much for my career. I can’t wait to connect all the dots in 6 months-I will keep you updated!


Briana Das ‘21, Psychology

Brown’s San Francisco Synapse trip was a unique opportunity to explore the place I call home. I felt incredibly grateful to have the opportunity to learn about a variety of perspectives from different companies in the area in the realm of entrepreneurship and tech. As someone interested in the intersection of human-centered design, design ethics, and entrepreneurship, there were valuable insights everywhere we went.

Some highlights of the trip included our discussion with Kat at YC, who gave us a look into how YC works to support startups and entrepreneurship networks, particularly seeking ways to scale while maintaining the value of carefully guided mentorship. At Slack, we spoke with Brown graduates and Slack product managers Fareed and Zindzi who gave us insight not just into what it meant to be a product manager at a high growth company like Slack, but also what it means to go out into the world with a Brown degree and how that impacted their path. One of the most impactful people for me was Stanford Business School professor, Fern Mandelbaum. She covered what she teaches, but also discussed identity, social innovation, and the vital importance of representation in the field of entrepreneurship.

Ultimately, the SF Synapse trip left me with this: Every one of us will leave Brown with a unique set of skills and mindsets that we can use wherever we end up. We learned to seek cultures of rapid growth and inclusivity. We learned the value of the relationships we keep, inside and outside of Brown. And the conversations we started along the trip will continue long after we’ve graduated.


Chuck Isgar ‘21, Business, Entrepreneurship and Organizations

While I gained many practical learnings, the clear highlight of the trip for me was the opportunity to connect with and learn from classmates, Brown alumni, and other entrepreneurial figures. Other students and I would discuss our biggest takeaways from each company visit; these conversations allowed me to form relationships with the other entrepreneurial-minded Brown students on the trip.

Various conversations and pieces of practical advice made the trip such an insightful experience. For example, Kat at Y Combinator helped me understand how accelerators and entrepreneurs can balance the many tasks that come up on a daily basis. Our visit to Slack allowed me to realize the importance of continuing to refine my writing skills. At our student-alumni dinner, it was a special opportunity to have a roughly equal number of students and Brown alumni who are working in various entrepreneurial-related roles in the Bay Area.

I found my conversations with Aerin Lim (Silicon Valley Bank) and Olivia Rodriguez (Instacart) to be particularly impactful, especially when hearing their stories of how they ultimately wound up in entrepreneurship-related roles.

The key takeaway was that you should have no fear in pursuing an entrepreneurial-related career from day one, even if that isn’t what many of your classmates are doing.

As well, it was very insightful to hear Lauren Kolodny’s explanation that there are many different paths to VC and to glean other lessons that she has learned in her journey of building Aspect Ventures. These are just a few of the many lessons I learned during the trip. To best put it into perspective, I began the tour with an empty notebook and by the end of our trip it was half-full.


Angela Wang ‘21, Computer Science and Economics

Words like “entrepreneurship” or “startup” excite with their glamorous promise of success and riches. What the Synapse Program did was to help me properly conceptualize the immense amount of work and adaptability that’s required to even come close to making good on that promise.

In this sense, the Synapse Program has been a great learning experience. In the space of a few days we were exposed to every aspect of the entrepreneurship process. Listening and engaging with alums in different stages of their startup journey was incredibly instructive, as it gave us an intimate glimpse into the challenges of succeeding within the startup industry in real-time. The alums were very generous in embracing us into their community, sharing their life stories, and very sincerely opening up about both the adversity as well as the technical struggles they had to confront. Their example demonstrated to me in a tangible and productive way how I should begin to model my career path.

Perhaps the biggest takeaway from the program was that it changed my entire attitude about what it means to be an entrepreneur. I had always thought of the entrepreneur as someone who strikes gold with a get-rich idea and then works on honing that idea into a company. What I’ve discovered – and this was the most exciting and freeing thing about the program – is that entrepreneurship is much more of a social and fluid process. I will never forget the eureka moment when Greg Kidd of globaliD completely exploded the horizons of my thinking on the entire entrepreneurship concept. His words have inspired me to overhaul and revamp my thinking on what it means to succeed in the world of entrepreneurship. Now, that world feels not only much more expansive but also more promising than ever before.

Tanzina Chowdhury ‘21, Computer Science and Economics

San Francisco Synapse was my first opportunity to experience the Silicon Valley tech ecosystem of startups and meet people full of entrepreneurial spirit. The insights from the alumni dinners and the startup visits were so important for me as a rising junior to think deeply about my ideas and possible ventures, as ideas alone are not effective until we can implement and execute them. The opportunity to conversate with the alumni and tech leaders have given me both motivation and connection to think more critically about my ideas and how to build a roadmap to execute them.

Mostly, it was a great team to travel with and I truly gained a lot of motivation from the ideas and ventures of my fellow peers.

The trip started with the meeting with Greg Kidd in the Digital Garage and I think that was a great introduction for the rest of the trip. Greg not only talked about globaliD and his experience with other ventures such as Twitter and Coinbase, but also discussed the future of the industry by giving us a Silicon Valley cultural overview. I have gained valuable insight from that talk about the future of keeping an electronic identity which seemed really interesting to me to research further into it to explore how it can solve other problems such as corruption. Also, I loved the alumni dinners as I could connect and learn a lot from their stories. Overall, I am really motivated by the Synapse trip and really grateful to be a part of the team of highly motivated individuals to build friendship and mentorship.


Rohan Gupta ‘22, Computer Science

The San Francisco Synapse trip was an amazing experience! The many Brown alumni that we met were all inviting and generous with their advice. It was interesting to learn about all of their various experiences and perspectives, some of which opened my eyes to fundamental changes in our world that I had not previously paid much attention to. Seeing their passion and dedication to their projects and businesses motivated me to follow in their footsteps.

My biggest takeaways from SF Synapse were the importance of relationships, communication, and generosity. Ultimately, business is all about the people – when employees are respected and treated well, companies flourish. Further, just as important as having great ideas is being able to express them clearly to others in both oral and written forms.

And finally, one can’t expect to just keep taking from others without giving in return, so generosity towards others is key.

Overall, I am extremely grateful that I was able to attend this trip because of all the awesome people I met and the helpful advice I received.


Chase McKee ‘21, Business, Entrepreneurship and Organizations

I had heard about the plethora of startups with investors clamoring to find the next greatest company, but I had never been able to experience it firsthand. Through speaking with and visiting both early stage and later stage companies of Brown alumni, I was able to have a truly eye-opening trip in SF. I learned about the hardships of being an entrepreneur, the brilliant moments of success that result from years of hard work and perseverance and developed invaluable alumni connections in the area to allow my learning to continue after the trip.

Additionally, I had the opportunity to learn more about the world of venture capital. Through our visit to Aspect Ventures, I was able to ask many of my most pressing questions about the industry. I appreciated the candid advice that venture capital is a tough business to gain employment in, especially right out of college.  While noting the challenge of entering the space, additional advice was given on how to succeed if given the opportunity to get involved.

One thing I will always remember about the trip is the stimulating interaction with the other students which was a valuable learning experience in and of itself.

Each student had an impressively unique background that allowed for differing perspectives. The other students encouraged voicing differing opinions on various matters which led to many fascinating and intellectually probing conversations. Learning from each other was a theme that grew throughout the trip and ultimately provided a pathway for deeper exploration of the entrepreneurial ecosystem.