Goodbye, Carta.
Creating things is fun. And I’ve had a ton of fun creating things with Carta.
I was Carta’s first product management hire in June 2016. And for the last 5.5+ years, I’ve joyously solved problems with incredible teammates across every part of our business. Today is my last full working day with this special company. While it’s sad to be walking away from one life chapter, I look ahead to the next set of horizons with excitement. But before getting to those horizons, I wanted to reflect and look back for a moment on the incredible journey it has been.
Building software solutions for cap table management, compliance services, and portfolio organization might not sound like the recipe for something special, but I assure you it is. Carta’s network touches on diverse user groups — employees, founders, investors, board members, lawyers — each with their unique needs and aspirations. From the outside, Carta received attention as tech unicorn whose rise and growth has surprised and captivated our industry. From the inside, it was even more special.
Finding Carta
People often ask me how I found eShares before it became “a thing.” The answer is simple: I found an interesting problem and just kept asking questions. In fact, my Carta journey began before I’d even heard of eShares.
Prior to business school I worked at two very different companies that highlighted a similar problem: Goldman Sachs and Klout. At Goldman–a multinational, multi-billion dollar investment bank–I had access to the most complete data sets in the world about public companies. There were few questions about a company or sector that couldn’t be answered without a little effort. At Klout–a private Series C startup who was first into the influencer marketing space–there was very little information available. Despite a valuation in the hundreds of millions, it was hard to understand how much my option grant was worth relative to the other securities the company had issued: common shares for founders, preferred shares to investors, a convertible note to Microsoft, and other equity grants to employees.
This disparity came to a head in March 2014 when Klout was acquired by another private company Lithium Technologies. Suddenly I found myself in a position trying to reconstruct the company’s cap table in excel by piecing together incomplete information. This led to my first attempt at building a “waterfall” analysis to understand how the company’s value was distributed to its many owners. Because I love designing things in excel (something our design team loves to give me a hard time about 🙃), I made my model so that anyone could input details about their own option grants, exercise history, and tax information. The result was a personalized breakdown of whether I should exercise, a range of what I could expect to make from the transaction, and what I could expect my tax bill to be.
Several coworkers asked if they use my model for their own holdings. At one point a small queue formed at my desk as people waited to input their information. As a product person who regularly analyzes human behavior, I was intrigued. Over the next several months–including a move to Boston to attend Harvard Business School–this moment stuck with me. And it led to a series of other questions: Why are public markets so transparent compared to private markets? Could private markets be made more liquid? Why don’t companies share information with employees regarding the company’s capitalization structure if it would help employees make judicious economic decisions? Could startup options be collateral for loans?
Over my two years at business school, I kept returning to these questions. I started using class time to investigate the space: how big was the market and was there really a pain point here? I presented on this problem to my Online Economy class. I also started to experiment with user testing and divergent thinking in my design thinking class led by Srikant Datar (now the HBS dean).
This led to work with two friends where we began to casually prototype website ideas for helping employees understand their equity and gain access to loan products to help them exercise options. Employees seemed eager for help, and there was a hypothesis that a site could connect employees with each other and help them collectively reconstruct a company’s cap table. We believed that company’s wouldn’t share this information as no employee I interviewed had received even basic cap table information like fully diluted share counts. Here’s one of the screenshots from the (very short lived) site:
It was over the course of investigating this problem that I started to hear about a company called eShares. The Palo Alto based company was helping founders move their cap table online–saving them tremendous amounts on legal fees and accessing cap table information in real-time. As I talked to numerous founder friends who’d moved to eShares, I was greatly impressed by three things: (1) eShares was generating a tremendous amount of user delight, (2) companies paid eShares for their service in a very SaaS-like way, and (3) companies were uploading their entire cap table data set.
The combination of these things — but especially (3) — made me reassess my mental model of the space. Whereas I had assumed that companies would never share cap table information, it turned out they had a massive source-of-truth data management problem of their own. Note: product people get used to questioning everything and being wrong a lot–and I had been pretty wrong on this one. A greater thing about product people is they’re flexible enough to change their mind when presented with better information.
Choosing Adventure
These discoveries occurred during my last semester at HBS. And while I had been investigating this private marketplace problem intermittently, I had not really considered it a viable path post-business school. The market for cap table software felt bounded by the number of startups who could pay for a service like eShares. With student loan debt piling up and days to graduation counting down, it was time to think seriously about what was next.
Despite talking with many innovative and exciting companies in San Francisco who were offering solid compensation packages (very important given my financial situation), I couldn’t shake this feeling that eShares might just be on to something. Finally one of my closest friends convinced me to “stop being an idiot” and at least reach out to learn more (Thanks, Shan!). He connected me with a friend who knew someone at eShares:
This cold email led to introductions with Josh Merrill, Sean Moran, and Eric Hurkman (three amazing people!). They told me about what eShares was building — and it was much bigger than just cap table management. I was impressed. The company was starting to explore an investor product that would bring venture funds and general partners into Carta’s networked product suite. I eventually came in for an onsite where I met this trio in person as well as product designer Andrew Young and finally the company’s founder and CEO Henry Ward.
My conversation with Henry was fascinating. I don’t think anyone has ever outlined a more exciting and challenging vision in a single meeting. eShares didn’t aspire to be just a workflow solution for cap table management, it was exploring the deeper concepts of ownership and marketplaces in fundamentally new ways. This meant understanding user experiences and businesses across founders, law firms, investors, LPs, board members, regulators, and more. The product problem was going to be crazy challenging, but one with generational impact potential. Mind blown. 🤯
The company also had some quirks worth considering. Until then eShares had never hired a product manager. I’d be the first PM and endeavor to bring this DNA into a company who skeptically viewed PMs as potential friction between development teams and business partners. I’d also have to spend my first several months commuting to Palo Alto for a strict 8:30am start time. This meant waking up by 6:00am each day to catch the southbound Caltrain. Lastly, since eShares was a Series B company, they wouldn’t be able to compensate me as highly as more established software companies — a big consideration considering I had a total of $1,300 in the bank + tens of thousands of dollars in student loan debt.
There was excitement on both sides after my conversations, and the following week I received an offer:
For seven days, I talked through the pros and cons with a number of business school professors. They thought the cap table market was too small to reach breakthrough status. The market surely had a near-term ceiling for the number of startups who could pay for a service like eShares. Using TAM as a guidepost, the other offers provided a clearer path to growth and viability as well as better compensation. They seemed like the clear better options. Why not pay down some debt and then take a shot at something earlier after that?
But the conversations I’d had with the eShares team stuck with me. There was an energy and excitement there that I hadn’t gotten from the other four offers I had received. The more I reread Henry’s blogs, the more eShares felt right. I chose the “adventure” option.
The Carta Experience
Looking back, it’s hard to not think that Carta was a no-brainer. But at the time, it didn’t feel that way. The company had Series B funding, but hadn’t yet expanded beyond the product market fit of its core cap table product. There were two big bets underway: building 409A valuation software and figuring out a product for investors. I was the product trifecta lead (modeled on Dave McClure’s “startup trifecta”) for the latter. One of our main product offerings for this group when I joined was taking custody of physical stock certificates on behalf of funds. We were still in the humble beginnings stage.
These humble beginnings with the Investor Services were hugely valuable for me. They challenged me to re-appreciate the role of product in the development process and adapt my style to the problems of the day. I developed a voracious appetite for talking with customers and users. I struck deeper relationships with our business teams to understand user opportunities and problems. I became more hands-on than I had ever been in my product career, which even included writing code from time to time (a few contributions I’m told have stood the test of time 😄). I found a passion for both getting into the weeds of problems and connecting it with the bigger picture of what we were trying to accomplish.
While putting together this blog, I uncovered a presentation I gave on what working on product was like for a new hire cohort in October 2016. Much of that joy and excitement I was experiencing shines through in how I described what PMs do:
- Curiosity (Sherlock Holmes and Dr. Watson): We investigate the world and its problems. We uncover user pain points and opportunities for software to delight. We use data to make testable hypotheses and question everything without ego as we learn more. We identify the right problems first and then their solutions.
- Adventure (Indiana Jones): We adventure with our development and business partners into the unknown. We outline exciting and compelling narratives that inspire our cross-functional progress and constantly unearth new treasures.
- Energy (Beyonce): We bring confidence and energy to whatever we do. Whether it’s shipping something that’s not perfect (but will help us learn more) or engaging with an unhappy user, we PM with style and set an example. We set the beat for shipping new things.
- Empathy (ET): We constantly strive to put ourselves in the place of the user. We don’t just solve problems, but we look to solve them in a way that brings delight and trust. Software can’t be soulless. When we see someone struggle, we naturally want to help. We empathize deeply.
The subsequent 5.5 years offered me the ability to learn and grow alongside an amazing group of talented people with the mentorship and support of Henry and others. Looking back, I’m proud of everything we’ve learned, the incredible experiences we’ve built, and the enduring relationships I’ve developed along the way. I’ve been fortunate to lead development teams across all parts of Carta’s businesses — investor services, private markets, valuations, employee experience, law firms, liquidity, and more. It’s hard to capture all the fun and energy that being on a rocket ship has been like so I’ve tried to focus on 10 of my favorite memories in separate post.
Thank You
This blog has afforded me the opportunity to reminisce and celebrate the people and memories that made Carta so special. It’s also provided a medium to lean into the life transition that comes with the bittersweet feeling of stepping away from a wealth of experiences that has been so good to me.
I am so sincerely proud to have joined Carta as its first PM. And in 5.5 years I’ve been fortunate to watch us grow from ~50 people to ~1,600 people and our valuation 100x from ~$75 million in our Series B to ~7.5 billion in our last Carta Cross transaction (which didn’t even exist as a thing when I joined).
I am in awe of the people I’ve had the privilege to work with here. I hope I have contributed back to them in turn with my energy, optimism, and passions for team-building and problem-solving. I am also fortunate to have worked with a visionary leader like Henry who gave me the opportunity and space to grow so much personally and professionally. Perhaps this is why, even after many years, I still volunteered to welcome each new cohort of hires with our “Get Amped about Carta R&D” introductory session.
The problem of ownership and private asset management is still in its early innings. I’m excited for the opportunity ahead for the Carta team, and I’ve never felt better about the position of the company and its people. I leave as an owner in a company who has done more to advance that mission than anyone else. That’s pretty cool. 😎
I’m also excited and hopeful that my next “product deep dive” will be as much fun. But that’s part of the adventure of stepping once again into the unknown and unfamiliar. Onward! 🚀