Joining Defy Partners: The Path To My New Home

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May 22 · 6 min read

We are so excited to have Brian Rothenberg join the Defy team, here is his journey in his own words…

Ten years ago I went to business school with the aspiration of shifting from product management into venture capital. I earned a VC internship where I learned a great deal about what had previously been an opaque world to me, including how great a job it is and confirming that I definitely wanted to be VC, someday. My most important realization was that I believed that I would someday become the best VC I could be through building my own lived experiences as a startup founder and scaler.

So I did what any rational MBA would do. I left my coveted VC role and I went to the other end of the spectrum co-founding my startup, SkillSlate. While my MBA classmates were recruiting with big firms and traveling the world, my co-founder and I were scooting around Manhattan on a used knock-off Vespa pitching any angel or VC who would speak with us.

Raising funding during the Great Recession in NYC we received 40+ “no’s” before our first big “yes.” I learned invaluable lessons around not only fundraising, but also what “good” and “bad” behavior with entrepreneurs looks like throughout this process. After closing our round, we spent the next couple of years building our team, iterating toward product-market fit, grinding out growth, and ultimately finding a good home for SkillSlate in our acquirer, TaskRabbit. The journey was rarely as glamorous as entrepreneurship is often portrayed, yet building a team and business from nothing is among the most gratifying experiences of my career. Being a founder myself has cemented my deep empathy and passion for all that founders do.

Wanting to continue to build out my experience in scaling businesses through every startup stage, I led customer acquisition for TaskRabbit through its series B and C rounds before joining Eventbrite in its relatively early days as the company’s first VP of Growth. There, I spent more than six years helping Eventbrite grow 10x into the world’s largest event technology platform and live experiences marketplace, generating $300M in revenues and culminating in our IPO (NYSE: EB) with a nearly $3B market capitalization.

Valley lore would have you believe that you get on a rocketship startup, and it’s all up and to the right. The reality is of course quite different: there are too many ups and downs to count. There are common patterns that I have observed at different stages or inflections within a company. Having eaten, slept (or not), and breathed this for over a decade, I have built better judgement from these critical experiences. Furthermore, sustained growth requires a deep understanding of all possible growth levers, combined with a systematic approach to driving ongoing growth within a company — fortunately my deep experience and passion here can be a great asset to founders and their teams. I believe that all of this will enable me to be the best partner that I can be to an entrepreneur as they inevitably drive through their own startup’s ups and downs on the long-term journey up and to the right.

But it’s not just about what I can add. I didn’t want to join a firm where I’d be a lone wolf searching for my own investments and being the only partner helping the founders that I work with. I wanted a team — an exceptional team, and one with shared values that I truly enjoyed being around every day. As cliche as it may sound, there’s one truism I’ve found to hold time and again: it’s all about the people. Ultimately for me, Defy was the perfect fit. Why?

Defy is an amazing, small but mighty team. And that’s by design (see next bullet). Every day I get to work beside my partners Neil and Trae who are incredible veteran VCs from top firms (not to mention both are former entrepreneurs and company creators). Plus I get to work with our Defy “Sages” in Brian Lee (founder of LegalZoom, ShoeDazzle, The Honest Company & more) and Sujal Patel (founder of Isilon which IPO’d and sold to EMC for $2.5B), as well as the rest of our truly phenomenal Defy team. Lastly on this point, Defy has some of the best limited partners in the business, which matters greatly in terms of founders increasingly caring where the money comes from, and it matters to everyone in that future success will benefit incredible universities, nonprofits, and other institutions that are positive forces in the world.

It’s a “right size” firm. Same for startups, being lean can be an advantage. The team is nimble & able to operate at the speed of entrepreneurship. For example, there is no Monday “partnership meeting” — our partnership will come to founders and make a quick decision. Additionally, with the trend of the big firms getting bigger and managing more and more money, the nature of this business is that they need to put that money to work (see next bullet), and will often try to consume a whole round even if it’s in the founder’s best interest to put together a consortium of strategic investors. At our size, Defy can lead rounds, or we will gladly make room for other investors to form the best investment syndicate for the company. Related, we won’t try to overcapitalize early-stage companies. The large funds often want to put $10-$25M to work in a single company. At the series A, I’ve seen that this can be destructive — more money rarely increases the speed of learning faster than the additional complexity of managing a larger team and having higher burn. That said, with more than $400M in capital across Defy’s first two funds, the firm has plenty of capital to lead full rounds and/or to heavily support companies with follow-on capital along the way.

Focused on the series A. We see a gap in the market. With a proliferation of seed funds and angel money, many interesting seed-stage companies are being formed. With the big firms getting bigger and needing to write larger checks, there’s a gap at the traditional $3–10M series A stage. Defy is focused on these true series A investments. We are active partners during this critical time as companies are honing product-market fit and starting to scale. From a personal fit perspective, I personally believe I’ll add the most value at this stage given my founder experience/empathy, and as a growth person the series A is the point when you start to see early signal around the company’s nascent growth levers that I can help to dial in.

Cultural fit + aligned values. In my interview process, Trae’s third question was around team and culture — “how I define it, what’s important to me, what kind of culture would I hope to build?” This theme continued with Neil and as a group discussion with the whole firm. It quickly became clear that we have many shared values: hustle, drive, respect, collaboration, family, authenticity, and passion for entrepreneurship. Relatively early in our process, the team invited my entire family to their family offsite in Carmel where we all spent time socializing, and working together. It felt like a true two-way culture fit almost from the get go.

Building the firm with the founding team. I like building with small teams. Joining Defy just two years in, there’s still a lot that I can help to build, including shaping our evolving culture and building the future of the firm with Neil, Trae, and team. This was a rare opportunity that doesn’t come along often.

For all of these reasons and more, I am truly honored to be part of this special Defy team.

Brian Rothenberg

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Early stage venture capital