TCT Exclusive: Kate Coughlin Stern of Homebrew, ex-Goldman, ex-Uber

We’re thrilled to announce this week’s exclusive with Kate Coughlin Stern! Kate began her career on Wall Street in investment banking before making the transition to Silicon Valley. Her operating experience at Uber helped propel her into the VC ecosystem, where she currently serves as Principal at Homebrew.

With a deep background in banking, consumer, and now VC, we discussed various cap table topics, including:

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

How did you start out with regards to your career?

I started my career as an investment banker at Goldman Sachs. I definitely didn’t know I wanted to join Wall Street when I entered college — I grew up in a family of scientists, so the finance world was totally foreign to me. I started to learn more about the capital markets while I was at school, and a summer internship at GS really confirmed my interest. I was immediately drawn to the fast pace and the quantitative nature of the markets, as well as interacting with the firm’s clients. While at GS, I helped corporate clients manage their macroeconomic risks, which gave me great exposure to companies across a variety of industries.

I graduated college in 2009, right in the middle of the last recession, so I have a lot of empathy for everyone just starting their careers now.

You’ve moved from banker to startup operator to VC investor. What advice would you give Wall Street folks thinking about transitioning into their first startup?

This is a tough one! 

First off, the transition can be difficult, so don’t get discouraged! Most importantly, start reaching out to folks in tech that are already in your extended network. Don’t treat those conversations as immediate job interviews. Instead, spend your time listening and getting a sense of the different roles and types of opportunities there are in the startup world. The culture shock between Wall Street and Silicon Valley is very real — at times it’ll even feel like you’re learning a new language.

As you get closer to making the transition to your first startup job, remember (and internalize) that no job is beneath you. Focus on selling your work ethic and ability to hustle — sometimes it’s valuable to just get your foot in the door. When I was making the transition, I emailed dozens of NYC startups volunteering to work for free, just to build up my resume. I ended up revamping the customer service operations at a tiny coffee subscription startup — it wasn’t glamorous by any means, but I was able to sell that experience during my interview process at Uber. 

Scrappiness pays off!

You’re currently at Homebrew, joining from Uber and Goldman. Tell us about your experience so far. What has been the most challenging aspect of the job? What’s been the most rewarding moment to date?

I joined Homebrew in February 2019, after almost 5 years at Uber. To say it was a big transition would be an understatement! I’m really grateful to have the mentorship of the two Homebrew founding partners, Satya and Hunter, who both made similar transitions from operator to investor earlier in their careers.

For me personally, the most challenging aspect of the transition has been shifting towards a much longer-term view of outcomes and success. While I was at Uber, we could measure the impact of our work almost immediately — we’d all gather around our shared dashboards after a new launch to see how it impacted orders, etc. That immediate feedback meant we were always iterating and tweaking things to optimize for success in the near term, and we always knew how well we were doing. Of course, we were also guided by longer-term priorities, but it was so rewarding to see the immediate impacts of our work.

By contrast, venture investing requires much more patience. As a naturally impatient person, it’s been a real shift in perspective to focus on a multi-year time horizon! That said, working with our portfolio companies to balance near term execution with a long term, crazy ambitious vision is its own kind of fun. Building enduring businesses is certainly a long game, and it’s been rewarding to see companies start to realize some of the dreams they outlined in their original pitches before they really got started.

Without question, though, the most rewarding aspect of the job is interacting with founders. Whether they’re at portfolio companies or pitching us, speaking with a great founder can be incredibly energizing. Their optimism is infectious. Every day I’m learning from people who just dream so big about the future and the impact they can have on it. It also makes the job intellectually stimulating. Every day I’m learning about something new. Especially after having a relatively narrow focus on food delivery as an operator, going from fintech to healthcare tech to DevOps to green tech in one day is fascinating.

What are some notable stories from your times at Uber and Goldman Sachs?

There are way too many stories for one newsletter, so I’ll limit myself to one from each company.

When I started at Goldman in 2009, the firm was really beginning to pick back up the pace of business after the worst of the recession. Everyone had just been through an incredible shock — the economy, the banks, and our jobs were not nearly as stable as everyone thought. It forced everyone to work harder and smarter. It also built resilience. This was also in the thick of Occupy Wall Street. It was an interesting experience to come out of college, go to my first real job, and have tons of protestors screaming at me each time I left the office, to say the least!

At Uber, one of my favorite and most chaotic times was launching the Eats business in New York. Before today’s version of Eats, Uber Eats was focused on instant meal delivery — each day, we’d feature two or three set meals and deliver them in 10 minutes or less. Delivering on that instant model meant setting up a new supply chain each day depending on which restaurants were featured, so getting it going was a huge challenge. In the weeks leading up to launch, I was spending 12-15 hours each day in the office doing everything we needed to prepare: onboarding hundreds of bike messengers in-person to ensure they understood the product, assembling the variety of racks and baskets they’d need to attach to their bikes to hold the meals, and sourcing insulated bags to ensure the meals were high quality when they reached customers. By our first day of service, I was absolutely exhausted, but seeing those first orders be fulfilled made everything worth it.

What’s your vetting process for seed-stage founders at Homebrew?

From the founder side, our process is relatively straightforward — we’re a small investment team (only three people), so we make sure we all have the chance to meet the founders and get to know them a little bit ahead of the investment decision. During those conversations, we’re looking for a few things. 

The first thing is mission-driven founders. We’ve all seen how technology can change the world in our own lives; we want founders who have a vision of a better future and believe that their company can help create it. 

The next is whether we believe that the problem they’re tackling is urgent and painful for a large segment of users.

And of course, that process goes both ways — we hope that while we’re making our decision, we’re giving founders a little bit of perspective on what it’s like to work with us over the long term. Just as we're picking founders and their companies, they're picking us. Founders should choose us if they believe that we can provide value and want to work with us on building their company as it gets started.

Any particular thoughts on the Uber/Postmates deal given your background on the Uber Eats team?

I’ve been pretty removed from Eats for a while, so I don’t have much more insight than anyone else. That said, Postmates was always a formidable competitor, especially in some key markets like LA, and has some fantastic restaurant partnerships. I’m excited to see what the two businesses can build together, especially in areas outside of traditional meal delivery (like Postmates’ existing convenience and drug store delivery options).

What new trends are you watching across consumer software? How has it changed since you were at Uber?

So much has changed since my time at Uber — and so many of those changes have been accelerated by the pandemic. One trend I’m really interested in is new types of communities. Instead of social networks connecting everyone, there are interesting new applications of digital community emerging to meet different human needs.

For example, I’m excited to watch the new group of startups tackle loneliness — we’ve seen some really inspiring founders tackling this from a community building angle as well as a mental health angle. We’ve also seen new tools and platforms for creators to grow and monetize a community of their fans, and allow fans to engage their interests more deeply. It’s incredible to see products ramp up to allow people to live off of their creative pursuits and pursue their passions in previously impossible ways.

What are you passionate about outside of work?

As a relatively recent transplant to the west coast (I moved from New York in early 2019), I’ve been spending tons of my free time exploring California. Of course, my exploring has been a little more distanced and involves lots of disinfectant now, but the hikes and beach visits have started up again. I’m also an avid traveler and love trying new restaurants, which I can’t wait to do again… someday.

Now that the world has locked down, I’ve been grateful for the time to connect with family and friends (even though it’s mostly virtual) and boot up my Kindle, which had been neglected for too long. When I’m not reading, I’m usually watching basketball or reality TV.  

And of course, it’s been great to spend even more time with my rescue pug, Frank.

Any mentors? In life / investing.

I’ve been lucky to have so many great mentors and advisors in my career — too many to name here. Of course, I’ve benefited from great advice from those senior to me throughout my career, whether that was from my managers or others who were simply generous with their time. But one of the best sources for mentorship and advice I’ve found has been from my peers. Whether fellow GS alumni from my analyst class, former Uber colleagues, or the wonderful women I’ve met through All Raise, I’ve found some of my most useful career decisions and conversations have been with peers — that perspective of essentially ‘growing up’ together can be really invaluable.

The year is 2030. How are people getting their food delivered?

I think the biggest shift in food delivery over the next decade will be a real increase in the popularity and frequency of grocery delivery. The pandemic has already led to a major shift in behavior here, with many consumers trying grocery delivery apps and services for the first time ever. Over the next 10 years, I’d expect that trend to continue, as users become comfortable with online grocery ordering, the user experience improves, and affordability and access increase across the country.

The other shift I’m expecting is a little less visible to end-users, but no less important — I think we’ll see an increase in delivery-only food businesses, whether that’s in the form of delivery-only restaurants (which we’ve already seen an increase with cloud and ghost kitchens) or vertically integrated grocery delivery services. These delivery-focused businesses will have better margins and lower price points (as they’ll likely pay less in rent and won’t need to focus on in-store customer experience), and should also result in a better experience for shoppers and couriers (no need to fight the crowds at a grocery store or at the hostess stand to pick up orders).

Thank you for your time and thoughts, Kate. We look forward to the continued success of you and Homebrew!

Sources: Crunchbase, LinkedIn, Twitter