Jenny Friedman: The Cardi B of VC

Venture capital can seem like a drab world sometimes.

Though far from the sobriety of investment banking, consulting, or private equity, it can suffer from the same uniformities of background, appearance, and thought. There’s a reason why being considered a “contrarian” was once a prized accolade, even if that term has been bludgeoned into meaninglessness of late.

If the asset class is a blur of monochromatism, all blacks and whites and dull grays, Jenny Friedman is a stripe of color thrown across the canvas. Extroverted, opinionated, and always entertaining, Jenny combines a love of deep research with a flair that has given her the nickname “the Cardi B of VC.”

In the middle of lockdown, we had a chance to catch up. I hope you enjoy learning about Jenny’s upbringing in New York, her escape from Goldman Sachs, and the audio erotica startup she wishes she’d backed.

Origins

Dreaming of dynasties

That changed a few years later: I remember my parents telling me about the book The Prodigal Daughter by Jeffrey Archer. It’s about a woman who takes over her father’s business, among other things. It’s funny how those kinds of stories can stick with us. For a long time, I thought that’s what I was supposed to do.

Great expectations

My dad works in finance and my mom used to too before she moved to the non-profit sector. Both of them have serious, successful careers and that was definitely the expectation growing up. They set a high bar for us to achieve big things academically and professionally. There was always pressure for us to hustle and do well.

All of my siblings ended up going to top tier schools and working in finance. In that sense, I think we were brought up with a traditional sense of what success means. Even working in early-stage venture capital feels like a bit of a rebellion.

Disillusionment in banking

My first job out of college was at Goldman Sachs. In some way, my upbringing felt like it predetermined me to start my career at a traditional bank — it was what I knew best. I think it was an incredible place to start my career and learn how to become a professional.

Breaking in

Interest in tech

It didn’t take me long to realize I didn’t want to spend my life in portfolio management. I found myself increasingly interested in technology. This was still early days for the NYC ecosystem, a time when you could Google “best startups in NYC” and find like ten or fifteen companies. Businesses like Minibar were just getting off the ground.

I realized that what I really was excited about was this new ecosystem, and venture capital in particular, which would allow me to build and manage a portfolio of insanely fascinating startups. Despite the fact that I grew up around my dad and uncle who both had an intense focus on PE, this new asset class of early-stage tech investing and VC seemed so different from the work they did on the growth side.

Negative signals

For a while, I was worried I wouldn’t be able to break into the tech scene — coming from a bulge bracket bank was almost a turn off to tech people. There was this stigma that finance people were too buttoned-up, didn’t understand the tech culture, came with some sort of arrogance. Plus, the channels to make that jump were far from established.

I remember talking to a headhunter that was looking to place me at other financial institutions. When I talked to him about a move to venture capital, he leveled with me. In so many words, he said, “Look, we don’t get hired to place you at a VC firm. That just doesn’t happen.”

I'm an impatient person, so that was frustrating. But I realized I couldn’t just jump from A to B and suddenly have a career in VC. I needed time to build experience.

Getting exposure

I targeted using the two years of business school plus the seven months or so between when I left GS before starting CBS to put myself in a different position. I got involved in as much as I could. Before school started, I interned at Minibar to get startup and operating experience and learned about e-commerce, logistics, and marketplaces. At school, I focused on building relevant skills, learning from professor VCs like Stuart Ellman from RRE. And I honestly just hustled as much as I could.

I was lucky to have a network, too. Adam Rothenberg from Box Group is one of my brother’s best friends, so he advised me a bit early on, and Liz Wessel, CEO of WayUp, introduced me to Nihal Mehta. He was the person that gave me my first job in VC, an internship at Eniac.‍

"The chillest person alive."

I was used to interviewing at places like Goldman where the processes were so formal and rigid.

Nihal was the opposite of that. He’s really the chillest person alive. We talked and got to know each other and then like three hours later he emailed me and said, “we’ve reviewed hundreds of applicants and we’d like you to join us.” If I had to guess why he wanted to hire me, I think it was because he knew I was ready to work and was hungry. I ended up interning at Eniac for almost 18 months.

Leveling up at Supernode

After I graduated, I was looking for a full-time job in venture capital. A friend mentioned Laurel, telling me that she was a successful entrepreneur and angel investor and was looking for a partner to run a fund with. I had been looking at associate and principal positions up to that point, so this was a huge opportunity.

Arranged marriages

When I look back on it, my partnership with Laurel feels almost like an arranged marriage. We didn’t know each other but we had a shared desire to build something special at the pre-seed stage. And we both really wanted it to work. So we jumped in at the deep end, drafting an agreement, negotiating terms, and starting to invest.

Three years later, and I can say that it’s the best decision I’ve ever made. We’re really complimentary. We both love to meet and host people, and we’re fierce, professional women that don’t take bullshit from anyone.

First wins

The gift of Electric

This is a little unusual, but one of the deals I’m proudest of wasn’t one I sourced.

Laurel met Ryan Denehy from Electric AI and was an early angel investor in the company. Electric provisions IT support remotely, taking the pain out of managing in-house. When we started Supernode, Laurel suggested I look through the data rooms of her 27 personal investments and decide which companies, if any, should be “gifted” to the fund.

Even though there hadn’t been a visible change at the company since Laurel made her initial investment and her position was still held at cost, I thought the concept was brilliant and that the company had a wildly impressive executive in place. So I asked if we could make Electric part of the Supernode fund.

Since then, Electric’s grown rapidly and raised a Series B from GGV and Dick Costolo and Adam Bain of 01 Advisors. I’m really grateful I get to be a part of their story.

The miss

Early days

I’m still early in my investing career, so I haven’t had enough time to see any misses become massive yet. I’m sure that will happen with time. But there are two companies that I wished I’d backed at the pre-seed or seed-stage: Dipsea and Headway. I learned lessons from both.

Audio erotica

Talia Goldberg was the first person to tell me about Dipsea. First of all, if you don’t know her, she’s a badass — the youngest partner in Bessemer’s history. And that firm’s been around since 1911. She’s incredible.

She texted one night and told me about this podcasting app that was something like Fifty Shades of Grey but audio. Essentially, erotica.

Unfamiliar territory

That wasn’t a space I’d spent a lot of time thinking about, but Laurel is into freaky stuff, so I asked what her thoughts were. She wasn’t really interested. I reached out to my girlfriends but couldn’t get them excited either. This was early days for Dipsea, I think they might have been raising a friends and family round at that point. Without traction, I was trying to get a sense of demand.

Months later, Dipsea raised $5.5M from Thrive and Bedrock. The takeaway for me was that to varying degrees, we all live in bubbles. I asked the women closest to me, but I could have been much more thorough in talking to people outside my circle. It’s still early days for the company, of course, but I should have diligenced the concept with a wider range of consumers.

New Yorkers

Maybe it’s because I’m from the city, but I really believe that you should never underestimate a native New Yorker. Oftentimes, they have a resourcefulness (and network) that can make a difference. I also think the pressure I had growing up is not unique — a lot of other born-and-bred NYers had similar experiences. I think that can make for resilient entrepreneurs — people that refuse to fail.

That’s one of the mistakes I made with Headway.

Underestimating grit

I think I was one of the Headway founders’ first pitches. I knew one of them peripherally but was reintroduced by friends, and though I thought their idea to build a marketplace for mental health was intriguing, and an admirable mission to solve, I didn’t see the big vision.

That was a mistake. Among other things, I underestimated the commitment of the founders to the company, their resourcefulness, and the scale of what they might build. They’ve become something of a benchmark in the mental health sector and are growing rapidly. It really taught me to value the introductions friends within my network make, even when the pitch may seem informal or more like a practice run. I got in my own way on that one.

In other words

The first word that comes to mind when I think of Jenny is “unstoppable.” I’m inspired by her boundless energy and how hard she hustles. She’s also clever, charismatic, and unapologetically real, which I deeply appreciate.

— Arielle Zuckerberg, Partner at Coatue

Called the "Cardi B of VC" by people in the industry, Jenny's electric personality is a magnet for founders, co-investors and LPs alike. She hustles for her companies like no other, and is starting to build a portfolio of game-changing businesses. I had the pleasure of working with her at Eniac, where she cut her teeth and found her passion in pre product-market-fit companies. Today, I look to co-invest with her as often as I can."

— Nihal Mehta, Founding General Partner at Eniac Ventures

Venture capital can be a transactional world — Jenny is a true friend. She values and cultivates relationships, which can be a rarity. She's also an exceptional networker, to the benefit of her portfolio. Whenever a founder needs an 'in' somewhere, Jenny always seems to know someone who can help.

— Brian Yormak, Partner at Story Ventures

Jenny is a central figure of the NY VC ecosystem. She has an unlimited amount of energy and hustle, loves to collaborate with others and is a great thought partner.

— Paul Strachman, Partner at Red Sea Ventures

Digressions

A favorite book

Plan B from Sheryl Sandberg. It’s a must-read, in my opinion. She talks about building her life back after her husband’s death. I found it very inspiring and relevant to absolutely everyone. We all face failures and need to learn how to find a path forward. I read this after a break-up and it put everything in perspective.

The theme song to her life

When I had to pick a song for my Raya profile I chose “Jenny from the Block” by J-Lo. One, it’s a great song, two, I don’t want to be judged for my music taste on Raya. And also, it speaks to me. Who doesn’t like an On the 6 throwback?

The last product she fell in love with

For a while, I was obsessed with this folding treadmill. It was a lifesaver during COVID. I think everyone needed a new thing, a new hobby, and this was mine. But I just gave it to my brother because he told me he hasn’t been exercising at all — it’ll be in better hands with him anyway since it was getting almost no use after April.

I’ve also been loving Verb energy bars. Yes, they’re a portfolio company of ours, but I honestly can’t even start my day without one anymore. I don’t drink coffee so I guess this is my caffeine fix, but they’re all-natural, absolutely delicious, and just effing dope.

Fantasy dinner guests, dead or alive

Maybe because we’re talking right after the conventions, but I’ve been thinking about Michelle Obama recently. She’s just such a freaking boss. I’d love to meet her and Barack.

I also would have loved to have met Whitney Houston. I’ve watched all the documentaries about her. I think about her a lot because although she had so much success and was so loved, she really struggled to be happy. I think we all can get caught up in the treadmill of work and forget about enjoying life sometimes.