HomeInterviewsDefy.vc, Interview With Partner Brian Rothenberg

Defy.vc, Interview With Partner Brian Rothenberg

Defy.vc Partner Brian Rothenberg
Defy.vc Partner Brian Rothenberg

Founded in 2016, defy.vc is a Woodside, CA-based based early stage venture capital firm focused on helping early stage companies mature and scale, from inception through exit.

To this end, the firm leverages a team with more than 50 years of venture experience, and successful operating backgrounds. Brian Rothenberg, Partner, replied our questions about himself, and the firm, introduced Defy.vc’s overall strategy, and shared with us his thoughts about the future of the tech landscape.

VCWire: Hi Brian, can you please tell us a bit more about you? What’s your background? 

I grew up in the San Francisco Bay Area, and after spending several years in LA and NYC, I returned back to the Bay where I’ve spent my entire career in tech.  I’ve spent the last five years as a General Partner at Defy.vc, investing in early stage companies and even helping to launch a couple new startups. I’m fortunate to work with a number of incredible founders building companies that I believe can positively change the world.  

Before joining Defy.vc, I spent more than 6 years scaling Eventbrite from a startup into the world’s largest event technology platform and marketplace for live experiences. As Eventbrite’s first VP of Growth, CMO and VP/GM of the company’s largest revenue segment, I helped to scale the business from a small startup to millions of users, $300M in revenue, and through our IPO. In parallel I spent years advising and investing in dozens of startups independently and through First Round Capital’s Angel Track & Expert Network, Sequoia Capital’s Scout program, and YC’s Growth Council.

Prior to Eventbrite I co-founded SkillSlate, a VC-backed local services marketplace, building the business through our acquisition by TaskRabbit (later acquired by IKEA). I started my first business from my USC dorm room—an early online ticket brokerage company called EventTicketsNow. At USC, I studied entrepreneurship and marketing and played for USC’s lacrosse team.

As a fourth-generation San Franciscan, I love building our life here with my wife, our four children, and our dog. On nights and weekends, you’ll find me coaching our kids’ sports, enjoying good food and red wine, snowboarding, playing guitar, and/or working out.

VCWire: Can you introduce Defy.vc? 

Defy.vc is a $700M venture capital firm working to fund the future by backing exceptional early-stage entrepreneurs. We’re a tight cohesive team with deep venture roots combined with extensive operating experience at companies including Stripe, Coinbase, Eventbrite, LinkedIn, and more.  We are all former entrepreneurs as well – our partners have founded more than eight startups collectively with multiple positive exits.  We value authenticity, and admire the tenacity it takes to turn a daring idea into an enduring company. We back extraordinary people capable of changing the status quo. We showcase their success, and work hard behind the scenes to amplify it.ì Which is your overall strategy?

Defy.vc takes a focused, artisanal, hands-on approach to investing and company building.  We have a high-conviction model where we most commonly write $2-10M first checks for meaningful ownership and are often a company’s first institutional board member.  Most of our investments are in the United States – many in the SF Bay Area, LA, NYC – but we love and have invested in other areas from Detroit to Louisville, and more.  We do make select investments internationally as well, generally when we have a close tie to the founders.  While many firms are only investing in B2B these days, our investments span across B2B and consumer as well.  From a sector perspective, we are generalists though we have invested extensively in vertical AI, enterprise & vertical SaaS, marketplaces, health IT, defense tech, blockchain/web3, and more.  

VCWire: Beyond capital, how do you support startups?  

Every investor on our team has founded companies as well.  We bring a great deal of entrepreneurial empathy, plus pattern matching from decades of operating across startups and scale stage companies.  From this deep experience, we work hard to earn the trust of our founders such that we become their first call when things are good, or bad.  

More specifically, we bring our hands-on operating help.  We have made numerous customer intros, we have placed dozens of key hires from our networks, and we do whatever it takes to help our founders succeed.  We have even taken on interim leadership roles within our portfolio companies, and we have been the direct source of introduction and helping to close hundreds of millions in follow-on capital for our companies from the most elite firms in the world. 

As founders at our core, we sometimes spot new opportunities that should exist, but don’t yet.  

In several of these cases we have done the hard work to further ideate, research, test, and even prototype new products – ultimately spinning up new companies and helping to match them with the best founders for those startups.  From there we provide capital to “hatch” these early startups into full-fledged companies and teams.

VCWire: What do you like to see in founders?….And what don’t you like to see in them? I mean, is there something which impresses you at a first glance?    

We have backed a diverse set of founders from both traditional and non-traditional backgrounds, so there’s a wide range of people which we think is important.  That said, we do tend to look for some combination of the following.  Authenticity – we love founders who bring novel insights from their real-life experiences that lead them to the problem area they’re working to solve, and a uniquely authentic approach to doing so.  Ambitious – we want to back founders with ridiculously large ambitions, who also have shown the tenacity to reach beyond where others think is possible.  Diverse – our firm doesn’t look like every other firm out there, and we take pride in attracting and backing people from many different backgrounds.  Commercial – we seek out IP-driven software businesses and love when there is deep technology in a company, but we balance that in seeking founders who also have a strong commercial sense (innovate on both product and distribution/GTM).  While we love moonshots, we do also like to see founders building “real” businesses with demonstrated pain points that they solve, ideally with evidence of paying customers who couldn’t live without the product.  

VCWire: Please, tell us a bit more about the portfolio. You can list five startups whose paths have made you particularly proud of.         

Our portfolio consists of roughly 70-80% B2B startups, and 20-30% consumer startups.  We have backed startups across many sectors, ranging from AI and deep tech, to consumer, to enterprise/vertical SaaS, cypto/blockchain, and more.  Our portfolio spans industries such as healthcare IT, business productivity, data and commerce infrastructure, fintech, education tech, logistics, gaming, marketplaces, among others.  We’re proud of all of our startups for different reasons, but will highlight the following as example Defy.vc companies:

  • Airspace – AI-powered logistics software for time-critical shipments.  Defy.vc was the first institutional investor, and the company has grown revenue several hundred times since then powering critical shipments around the globe.
  • Novi – Supply chain transparency software + B2B marketplace for procuring clean and sustainable ingredients that create the consumer products we all use everyday.  Defy.vc was the first investment into the company, which now works with retailers such as Sephora, ULTA Beauty, Target, and helps more than 3,500 consumer brands create and deliver healthier, more sustainable products.   
  • Apploi – All-in-one workforce management platform for healthcare.  Defy.vc led Apploi’s series A, and the company has grown dramatically since then, helping our critical healthcare facilities better find and manage their workforces.  
  • Safara – The next-gen online travel site for millennials and gen-Z.  Defy.vc led Safara’s seed round with Sequoia Capital, and the company is growing quickly.
  • Arena Club – The ultimate online marketplace for buyers & sellers for sports and entertainment cards, authenticity guaranteed. Co-Founded by MLB Hall of Famer, Derek Jeter, and serial entrepreneur Brian Lee (LegalZoom, The Honest Company), Defy.vc led the company’s series A and the business is on its way to becoming a market leader.

VCWire: Which sector/s would you bet 2 cents on in the next five years?

We believe in backing amazing entrepreneurs who spot opportunities through their lived experiences across many different sectors.  We want to talk to those founders regardless of industry, however, I’m particularly interested in the following areas:

Vertical AI – Defy.vc has invested in vertical AI for the past five plus years, and believe there will continue to be huge opportunity for the next five as well.  In particular, we’re fans of founders with deep experience in a specific industry (often old or opaque markets) who build vertical-specific software that solves key workflows, and in doing so, generates proprietary industry data that fuels deeper AI solutions.
Blockchain/Web3, specifically DeFi or Decentralized Finance – Personally I’ve been a long-time crypto HODL’r and enthusiast, but my eyes opened wider as DeFi gained steam in 2020.  The app and infrastructure layers have evolved greatly, and I’m a believer in the shift toward more decentralized solutions that democratize access and increase financial inclusion for more people around the world.  We are still in the early innings of adoption, but gaining steam.  I’m actively investing in and even incubating multiple new startups in the space after building our first one through the depths of this past crypto winter.  We’re long-term believers through the up and down cycles.