TCT Exclusive: Gaby Goldberg, Analyst @ Bessemer Venture Partners

We are thrilled to announce this week’s exclusive with Gaby Goldberg, Analyst at Bessemer Venture Partners! Her early exposure to the startup & venture ecosystem shaped her decision to take leave from her senior year at Stanford to pursue her passion of working in venture capital. Most recently, she worked directly with Jeff Morris Jr. at Chapter One before joining the team at Bessemer Venture Partners. Though she is relatively new to the tech scene, Gaby has created quite a splash. We sat down to pick her brain on all things cap table related, including:

TCT: Thanks for sitting down with us, Gaby. Let’s jump in.

You’re currently on leave from your senior year at Stanford, where you’re studying Symbolic Systems. Despite being relatively early on in your career, you have an impressive background within venture capital. What brought you into this space and why did you decide to take a leave?

I feel lucky to be working in venture capital this early in my career, especially since my journey into venture was so quick and unexpected.

As mentioned, I’m on leave from my senior year at Stanford, where I study Symbolic Systems. The major combines computer science, philosophy, linguistics, and psychology, providing hands-on technical training with a deep understanding of how people think and communicate. My general plan was to finish undergrad and join a company as a product manager — Symbolic Systems has a legacy of PM-esque alums (Reid Hoffman, Marissa Mayer, Mike Krieger, etc.). Clearly, that didn’t go as planned! I took last winter quarter off to work on a product team in Tel Aviv, and my spring quarter was fully remote due to COVID-19.

This past summer, I had the incredible opportunity to join Jeff at Chapter One. I took the job, not realizing the extent to which it would shape my career going forward. I understood very quickly this summer that there was nothing else I wanted to do after graduating besides enter the world of venture as soon as possible.

My leave from school is a bit unconventional — normally, I’d be eager to be at school for my senior year, finishing out my degree. However, Stanford is fully remote right now, and my quarter of online school last spring wasn’t great. I decided I’d rather spend this year working with brilliant founders and investors, rather than sitting in Zoom lectures all day.

What’s the most interesting course you’ve taken so far that you would recommend to rising operators and investors within the startup & venture capital community?

My favorite class at Stanford is called Social Computing, and I’d recommend it to anyone working or investing in consumer technology. The thesis surrounding the course is that social computing systems influence the way we interact with those around us: everyone including our friends and enemies, our family members and romantic partners, and even our organizations and societies. How do we design these systems to be ethical and effective? The class covers design patterns for social platforms along with the foundational ideas that underpin them, and it culminates in creating a social computing system of our own (FWIW, I created a social birdwatching app… and no, I wouldn’t invest).

Earlier this year, you spent six months living in Tel Aviv, interning at two different Israeli companies. What were your biggest takeaways from this experience? How would you compare Israel’s tech ecosystem to that of the US?

The summer before my third year at Stanford, I worked at Deloitte Catalyst in Tel Aviv, connecting Deloitte’s multinational clients with innovative startups on the ground of Israel’s high-tech ecosystem (often referred to as the Startup Nation). For one of my projects, I developed a report on artificial intelligence infrastructure — you can read the published version here: Israeli Startups Eliminating Bottlenecks in the AI Workflow.

I enjoyed my time so much that I decided to return during the winter of my junior year. Since Stanford doesn’t have an abroad program in Israel, I took a formal leave of absence for the quarter and went on my own. I joined the product team at Hibob — actually a Bessemer portfolio company — and spent three months working and learning Hebrew through ulpan.

Israel’s tech ecosystem is one-of-a-kind. The top country in terms of venture capital investment per capita, it’s one of the most densely concentrated centers of innovation in the world. This is due in part to the mentality of its people: Israel has a culture of assertiveness, informality, and tenacity, known commonly (and lovingly!) among Israelis as chutzpah.

If you’re interested in learning more about Israel’s tech and venture ecosystem, I highly recommend Ground Up Ventures’ yearly State of Seed report.

You worked as an Investment Associate with Chapter One this past summer. What was it like working directly with Jeff Morris Jr? What was your biggest takeaway from this experience?

Working with Jeff at Chapter One this summer was a once-in-a-lifetime experience. Besides sourcing deals and conducting due diligence on companies in our pipeline, I assisted in the creation of Product Club, a ten-week product mentorship program (read more about the three companies here), and Investment Club, a new scout program for the fund.

From the outside, venture capital can seem really confusing. Jeff helped me learn the ropes — from sourcing a deal, to writing an investment memo, to sending a pass email, and everything in between. On that note, my biggest takeaway is that venture capital is all about the people and the relationships you build. Here’s a quote from Jeff that I’ve held onto:

“It is important to remember that we are in the people flow business, not the deal flow business. Don’t chase deals that everyone else is chasing. Rather, spend your time creating meaningful relationships within engineering communities, design communities, and with other investors.

You will be far happier if you focus on creating authentic relationships. Most deals we do won’t be successful. But if you focus on the people, your happiness won’t be dependent on any given deal.”

You recently announced that you’ll be joining Bessemer Venture Partners, congratulations! What will be your area of focus and what are you most excited about?

Thank you! As of this interview’s release date, I’ll have been at the fund for one week. My main focus areas will be consumer technology and future of work; that being said, I have a lot to learn so I’m excited to enter the role largely as a generalist.

Above all, I’m most excited about the people! I am grateful to be joining such a superstar team with the opportunity to work alongside some of my biggest inspirations in venture capital.

You recently published “Curators Are the New Creators,” noting that the business of influencer bundling has only just begun. What types of opportunities do you see within content curation and the future of how consumers interact with content?

The general thesis of the piece is that it’s becoming increasingly difficult to separate signal from noise; as such, there’s an increasing willingness to pay for high-quality content. We can’t change the amount of information that exists, but we can change how it feels to navigate it.

I’m excited to see what types of platforms might emerge in this space. For example, we already have recommendation-driven e-commerce sites, like The Infatuation or Wirecutter. Another potential vertical is gaming, with great insights here from Blake Robbins. At the end of the day, across all industries, consumers are engaging, communicating, and spending more than ever before. There’s a massive opportunity to capitalize on this information overload and curate high-quality content at cost.

You seem to be very plugged into college and the recent grad ecosystem. What are the biggest challenges that new grads are passionate about solving? What types of startups and industries are they looking to join?

I can’t answer this question without referencing the incredible Gen Z VCs Report by my friend Meagan Loyst! After speaking with over 70 young investors, Meagan found that some of the most popular trends among Gen Z include social gaming, the creator economy, EdTech, and the consumerization of enterprise software. Popular brands and companies included legacy businesses like Apple, Instagram, and Nike, as well as new incumbents, like 100 Thieves, Italic, and Glossier. In terms of the types of startups that new grads are looking to join, Meagan writes that “Gen Z is full of socially-conscious consumers who care about things like environmental impact, sustainability, positive and inclusive messaging, and being value-driven.” I think Meagan is spot-on, and highly recommend you give her report a read if you haven’t done so already.

Do you have any mentors? If so, what role have they played in your career thus far?

Absolutely, and I have been so lucky to have had their support throughout both my life and my career. I will say, the mentorship that has remained the most constant over time is that of my parents.

My parents are both immigrants to the United States. My mom, specifically, learned English while in school, went to medical school at 18, and had three kids without ever leaving her job as an OB/GYN. When I was a teenager, both of my parents quit their jobs to move my family across the country to California, rebuilding their own lives and careers in order to create a new life for my brothers and me. The amount of doors my parents have opened, both for themselves and for others, inspires me every day. They will always be my biggest mentors.

A close second to the mentorship of my parents is that of my peers: some of my most valuable discussions regarding my career have been with those going through similar life experiences. There’s a unique sense of trust and mutual understanding that forms when you “grow up” alongside others, and it often provides a perspective you can’t find anywhere else.

Above all, mentorship has already played such a crucial role in my career and personal life, and I am dedicated to paying it forward. I’ve said this before and I’ll say it again: if you are a young person in tech or venture, I am always happy to connect! You can reach me via my DMs.

What are you passionate about outside of work?

I’m lucky to live near both the beach and the mountains, so I’m a big fan of anything outdoors! During quarantine, I’ve done lots of hiking and trail running, and have found both to be great ways to unplug and burn off steam at the end of a long day.

I also love to read and write. I write about consumer technology on my Medium page, and I also love to write poetry in my spare time (although that doesn’t get published!). During quarantine, I hosted two book clubs — a Venture Book Club for friends in tech, along with a book club with friends from high school while we were all quarantining back in our hometown.

Even though you’re early in your venture career, we have to ask. What’s your secret for getting on the cap table? If not your secret, what are you seeing as an edge for getting on the cap table?

A great piece of advice I got a few years ago to be well-lopsided, meaning you’re well-rounded but have a competitive edge in a certain area, or something that makes you stand out. That can manifest as a specific industry focus or a particular skill you can offer to founders. For me, I like to spend my time focusing on consumer software businesses, and my favorite stage has been helping a product achieve its first 10,000 users.

On a personal level, I fell in love with venture because I loved the relationships I was building with founders and investors across all industries, geographies, and stages. At the end of the day, I want to be on the cap table if I truly love the founder and her vision for the company. If I can build trust with a founder and show up for both the highs and the lows, then I’m off to a pretty good start.

On the flip, what’s the biggest cap table “mistake” you’ve seen thus far?

I’m still too early in my own venture career to have cap table “mistakes” of my own (early-stage investing has a feedback loop much, much longer than my few months of experience!), but I love reading Bessemer’s Anti-Portfolio, with the incredible companies they missed over the years.

What advice would you give to folks early on in their career looking to get into venture capital?

As I mentioned earlier, venture capital is all about the people. Don’t be afraid to be scrappy and get out of your comfort zone so that you can meet others in the industry and establish your own place in the ecosystem. Building relationships is a crucial aspect of growing as an investor: in my opinion, one of the most valuable skills you can have is writing a great cold email.

I also love this quote from Sahil Lavingia:

Doing the job before you get the job is a great way to get the job.

— Sahil (@shl) October 27, 2020

The year is 2030. What’s the state of venture capital?

Venture capital is incredibly competitive right now. There are a large number of new funds (solo capitalists, operator-angel funds, rolling funds, etc.) competing with larger institutional funds. Additionally, this year’s expanded accredited investor definition has further increased the pool of eligible investors for early-stage companies.

Over the next decade, these trends will only intensify. As venture capital becomes increasingly accessible to founders, there will be more pressure on investors to have a defined value-add besides their capital alone. (Note: a great example that comes to mind here is Form Capital, which invests real design expertise alongside seed funding.)

Most importantly, I’m excited to see venture capital expand to include more diverse voices, backgrounds, and perspectives. There’s still a lot of work to do, but organizations and funds like HBCUvc, Femstreet, and Rarebreed VC make the future look bright!

Thank you for your time and thoughts, Gaby! We look forward to the continued success of the various companies you’re involved with!

Sources: Crunchbase, Twitter, LinkedIn