Why This 28-Year-Old Executive Left Square To Become A Venture Capitalist

Business Insider

Square executive Jared Fliesler confirmed today that he's leaving the payments company and becoming a venture capitalist, as Business Insider first reported last month.

He's joining Matrix Partners as the firm's eighth investment partner—and at 28, the youngest.

He's the third Square executive to leave to become a venture capitalist in eight months—a coincidence, he told Business Insider, but one that might speak to the personality of people attracted to a fast-growing company in its early stages. Megan Quinn, Square's director of product, joined Kleiner Perkins last year.

And Keith Rabois, whom Fliesler worked with closely at Slide before its sale to Google, is joining Khosla Ventures this month.

Fliesler said his departure had no connection with Rabois's; as we reported, Fliesler announced he was leaving before Rabois revealed he was resigning from Square after he'd been threatened with a harassment lawsuit by a Square employee with whom he'd had a personal relationship. (Rabois and the company deny the claims, and no actual lawsuit has been filed.)  

Fliesler shared with Business Insider the text of a blog post about why he's becoming a venture capitalist. In it, he says that he thinks he can replicate the experience of being hands-on at a startup—but with more companies. Here it is:

I think it’s hard for ambitious entrepreneurs to ever really be content. As soon as they hit a milestone or goal, they tend to just move the goal line out and think about what more they could do (a temporal nature my team has always found entertaining about goals we set). It’s important that we pause to celebrate the success of hitting the goal, but then it’s time to get back to work on the next big milestone we can accomplish.

I’m constantly pushing and questioning myself to make sure I’m both on the right path and working towards the highest impact goals. I’ve been unbelievably fortunate and lucky to have the opportunities I have had and people around me that believe in me and help open doors.

As I considered and spoke with people about what might be next over the last few months, I received a number of questions that largely boil down to the following: Square’s an incredible place with wonderful people and they’re truly trying to change the world (which I love), so why would I even think of leaving? And if I did leave, why would I go into venture?

To answer these, I go back to my time at Slide and Google. If I think about what I’ve loved most in my career, it’s working in really small teams towards some audacious goal where we’re all sleeping, eating, bleeding, and breathing what we’re trying to do. I experienced this every day for the first few years at Slide and tried, as much as possible, to maintain that culture when we joined Google. Though I really liked my role as Director of Product at Google, it was hard to truly recreate the start-up vibe within a larger company.

My original plan after Google was to go start a company; either from my own idea or by joining a small founding team. At the time, I was an advisor at Square and could see the company’s explosive growth and potential. So when my former boss came to me with the opportunity to run growth at Square, I had to say yes and I put my plans of starting a company on hold.

I joined Square to figure out the big growth levers, build a team and foundation that would enable Square to scale around the world, and establish the right distribution and marketing channels to make sure that we controlled our destiny. By late-2012, it felt like we were well on our way to accomplishing these goals. We were moving to a scaling and optimizing rhythm and many of the challenges ahead were around continuing to iterate and optimize. We also hit an inflection point where we went from looking for an endless number of new channels to spend capital efficiently for customer acquisition to having an abundance of channels established and optimizing for payback. My team had grown from a small group to more than 70 people and the year ahead was about doubling that team and continuing to operate at a consistent cadence. At that point, I started seriously consider what was next and how to get back to what I enjoy most, working with a small team to solve core challenges at the whiteboard.

I met the Matrix team about a year ago at an event they hosted and casually stayed in touch. Over the last 6 months, the conversation shifted from a casual one to figuring out how we could potentially work together. I don’t think any of us knew in what capacity “working together” would ultimately manifest itself, but it was clear that there was a fit.

Like most entrepreneurs, I had previously given some thought to working in venture, but resolved that it was something I’d do later in life. I continued the thought process around my path forward and, in parallel, spent more time with the Matrix team learning about the firm and what it actually meant to work in venture with them.

One of the biggest realizations I had was that no (successful) company was going to stay in my favorite part of the growth stage: going from “this looks like it’s working in a few tests cases” to “wow, this actually can work at scale.” At some point, successful companies reach scale and then you’re optimizing the curve vs. setting it. In addition to wanting to work in this necessarily finite stage of a company, I’ve been spoiled by massive scale and I was looking for something BIG. The truth is that if I had an idea that I couldn’t stop thinking about, I’d probably give into my builder mentality and start a company. What might be even better though, is finding a way to work with a number of companies that are in this stage.

Investors should work for their portfolio companies. They should partner with them on the hardest problems and help them, against all odds, succeed at astronomical levels. As I learned more about Matrix, it felt like there was a match. They’re hands on and work with a small number of companies to truly change the trajectory of those businesses. I’m not joining Matrix to write checks and walk away. I plan to invest in a small number of companies and to be highly involved during the early stages, effectively working at each of the companies in which I invest. My investment strategy will mainly focus on identifying incredible entrepreneurs that are trying to change the world and specific companies where I’m uniquely suited to help them do that. I’ll start by investing in companies I’d consider going to work for and I hope that people will only take my investment if they would consider hiring me. If both of these aren’t true, I’m not the best investor for that company.

VCs have a unique vantage point. They see both the good and bad decisions that each of their portfolio companies make and can leverage this information to help each succeed (and hopefully make fewer mistakes). I often leveraged our investors for insights as I made growth decisions for my previous companies, but I wish I had one that was in the weeds with me in the earliest stages of building our growth strategy. I want to be that person for the companies in which I invest. Over time, each company will go through their own growth cycle and move from setting to optimizing the curve and I hope I can help them to navigate through these early, and often treacherous, waters of growing their business. If I can play a key role in helping multiple companies grow, scale, and ultimately succeed I’ll be happy.
- Jared



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