WIN

What is the story behind your two startups? Can you kind of tell us a little bit more about what you innovated and how you feel like you might have shown up as a woman in innovation in that process?

Sequoia

The two companies were almost a decade apart. The first company was called Seven A.M. and it was in the edtech space. We were direct competitors with MasterClass, who have gone on to do amazing things. That company died about four years in, purely because I had no idea how to build a business. I knew how to raise capital, but not how to build a sustainable revenue model. The Silicon Valley ecosystem was all about raising capital and I realized we needed to take a step back to look holistically at building the business. That took me on a trajectory of creating another company called Commas, which was all about how to build a profitable business. I brought on experts in every vertical, from sales to marketing operations, and just learned as much as I could. I wanted to take our minds out of venture capital for a second. Ironically, a venture capital firm heard about it. We had a conversation and they were like, "Hey, let's roll that into our venture capital firm.”

That was my first acquihire. I ended up at their firm on the platform side, but it wasn't called platform then. We helped their founders productize every single partner's information from their different verticals. While I was there, I started coaching founders and we ended up having a TV show called Startup U, which was basically a baby Shark Tank on ABC Family. It died very quickly, ABC family was not the right network for it. But that show, as an entrepreneur in residence and working with their founders, I grew an affinity to coaching entrepreneurs and I stayed doing that throughout that acquisition. Once I left, I continued to coach them and I think coaching is the through line from the beginning of my founder journey to now. This current company has been four different pivots since we started. Before all this tech came into my ecosystem, I actually was a commercial music video director. 

My brain has always been in the creative space, and I channeled that into the second startup, which started as a marketplace for videographers and photographers. When we began, I spoke to my co-founder about whether we wanted to hit the home run or do a lifestyle business. He was like, "Let's go for the home run.” We started raising capital for it, and there was a lot of pushback. Investors loved the idea in 2016 but were focusing on different things today. We looked at the ecosystem of what we had built, and knew we were profitable. There were two options, we could continue to have this marketplace where you book photographers or videographers on demand or we could pivot into AI. And we decided to pivot into AI. 

At first, we pivoted into AI workflows for creatives, and it was really interesting because at that time, maybe two years ago, creatives wouldn't even touch AI. We saw creatives as the perfect people for AI because they actually know what to do with it. They know how to create storyboards, shot lists and a narrative arc. At the time, they were so turned off by the idea of even using it that we realized we couldn’t sit there. Every single major tech company was throwing money into the agentic space, and again we had one of two choices: we could pivot out of this, or we're gonna get hammered. I took everything I learned from being a director and put it into an agentic workflow that could spin up a commercial in just a few hours. Then we had to figure out what our brands actually needed. What was the missing component? For me, it was revenue. When you're targeting SMBs, you need to be very cognizant of not charging too low because then you need a massive amount of volume. We started working on how to target the right customer just enough that we know they can actually afford to continue to have this. It all starts at the top of the funnel, which was attraction, by letting them create their commercials. We pivoted away from that and realized our customers are way too early, this was more mid-market enterprise work. You don't even know what this means as an SMB, you are just thinking about how to sell it. They aren’t thinking about their position in the market place, so we moved down market to the retention layer for people who have been in the market generating revenue. That's how we ended up in agentic commerce. Agentic commerce meant they had customers who had churned out of the ecosystem. Our company today has an AI agent that reaches out to the customer, figures out why they churned out of the ecosystem, and tries to win them back into the ecosystem. 

WIN

You mentioned your co-founder earlier. Throughout your journey, have you always worked with the same co-founder? How has that evolved over time?

Sequoia

When I was at Draper, I didn't have a co-founder. Along the way, I realized Silicon Valley won't fund you without a co-founder. I was like, oh no, what am I gonna do? I ended up doing something that you should never do, which is to reach out to a co-founder who doesn't know what it means to be a co-founder, and this co-founder was a celebrity. That is just all the things that you should never do.

You might think it’s positive because they will bring traffic. For me I realized they wanted the attention but didn't want to work. They just want to be the face. I needed somebody in the weeds with me. My co-founder actually had another startup that got funded by Draper and we were both in the ecosystem. That startup was in the blockchain space, and we just stayed connected throughout the years. When this company came up, I reached out with a billion dollar idea and asked him if he wanted to work with me. 

WIN

What was one of the biggest challenges you faced getting your first company up and off the ground as much as you did.

Sequoia

I came from the creative industry, and in the creative industry, you're only as good as your last job. You’re constantly trying to avoid failure. In tech, you are always running into failure, it’s championed. Fail fast, fail hard, fail forward, all the things. When I started, I didn't understand that and I was so afraid to fail. I didn’t want anybody to think that I didn't know what I was doing. The entire process being on the StartupU show, the last thing I wanted them to know was that my company was falling apart. 

I kept thinking everything was fine but it wasn’t and I stayed there trying to work on it and kept trying to work on it. At the time, we were generating revenue, but not at the magnitude and speed at which we needed to in order to raise more capital because we needed to show a certain amount of traction for the business. And so I did everything I could think of including interviewing at Masterclass so I could see what was going on. At the end of the day, I learned that you have to see failure as positive and be transparent about it. 

WIN

Where did you find community in the start-up ecosystem and how did that benefit you in the long run?

Sequoia

My opportunity with Draper was super happenstance. I had been in LA, thinking about what I was going to do next. The entire entertainment industry was tanking. This was when streaming started to enter the industry and people were panicked. I saw it happening and decided that it was time to switch. I went to Silicon Valley to teach at an all girls entrepreneurship boot camp. These girls were between the ages of 10 to 15 years old and they came to camp to learn coding and I was there to teach them branding for the products they created. The program had them building products from scratch and then pitch their ideas to venture capitalists. I was so fascinated by the entire thing. I had a little girl, Sanjana, who created an app that could change the color of your shoe, and then by Friday she was talking to the VC about how he would fund it and what she would need to do. I was so impressed and one of the instructors saw that I was so into it. She suggested I look into the Draper University program.

I looked it up, and to me, Draper looked like an adult summer camp. Tim's theory is all about make it fun, or don't do it. He pushes you to the brink of exhaustion in the most creative ways possible. That's how I got introduced into the ecosystem. I had no idea that Tim Draper's great grandfather started venture capital in Silicon Valley. I had no clue, it just looked fun to me. That's how it happened.

WIN

How did you leverage community to help you lift off in your own vertical?

Sequoia

I stayed in the ecosystem over the course of my career in entrepreneurship, and I have a natural strength in building relationships. When I build relationships, I don't ask for anything. Oftentimes, I think people try to leverage the relationship too early. For me, I've been really careful to not leverage them for anything. When it came to my second company, I was really rooted in the startup ecosystem from my prior company, working with Tim and investing myself. When we started crowdfunding our friends and family round for Lexore Spark I just turned to my LinkedIn network. We raised $140,000 in a month. It was crazy. We raised $10,000 in a day and I knew we were on to something.

But that was the leverage I had. I had never tapped those people so when they saw my fundraising outreach, it was like oh Sequoia of course, we’ve been watching you for years and you haven’t asked for anything, of course I’ll invest. That's how I was able to leverage the network for the second company.

WIN

Switching focus to your investor lens. Can you speak to how your perspective grew when you started to understand the investor lens alongside your founders perspective.

Sequoia

It's all unit economics and I had no clue. Like I'm a creative, we're just gonna create something. It's gonna be great. It's gonna be awesome.

I didn't understand the unit economics of the business. When we were doing diligence on deals, it was all about unit economics, making the lifetime value make sense within the business and keeping customer acquisition cost low. Once I understood that, I understood why my first business didn’t work. I just wasn't optimizing for all that,it was just fun for me.

After seeing deal after deal, how and why people invest, I had a much more holistic understanding of the industry. Oftentimes, investors rally around one founder. It’s not as happenstance as you think, it’s actually very structured. It’s not because you know you have this thing, they all talk to each other and share deals. Once I understood that perspective, I had to compartmentalize it, which felt weird. But when I got back to the founder side my brain switched and I had to remind myself that I knew how it works.  

If you can’t get a champion of investors to all believe in this concept simultaneously, I was going to be in trouble. Having that perspective helped a lot and I recommend every founder take an investing course if they can. It’s vital to know what the investors are measuring against because what founders don’t understand is that investors have a fund they must return. There’s a lot of math on the investor side too. If they are expecting a 10x return on the fund, it doesn’t matter what you say if they don’t believe you’re capable of making it happen. If founders understood the actual math, you realize it’s not a game, it’s really clear what you need to return the fund. It’s a mix between the belief in the founder and some truth in the math, once a founder gets that side, a lot of them shift to a service-based or lifestyle business. 

WIN

What is your perspective on how the women founder ecosystem has changed over the course of your career? 

Sequoia

I think it's really important that women are founders of companies, but I also think it's equally as important that women are capital allocators. Silicon Valley looks for pattern matching and they’re very clear about that. If women see themselves in those patterns, they’re going to want to invest in themselves. It’s a subconscious bias but the math works. You think if I put this money into this type of founder, the likelihood of the exit is this. If we don’t have those representatives and examples, then it’s that much harder to get the capital. It’s also in the culture. I’m looking at two companies right now, one male-owned and one women-owned, and they run completely differently. Women founders give more space for women to see that they’re capable of doing the work. The deal here is that the likelihood of us flourishing to our highest potential is going to be contingent on the women who came before us. That’s why it’s so important that the ecosystem has more women founders, more women investors. 

WIN

When you think about your journey so far, what is a moment you’re proud of. What gets you out of bed every day. 

Sequoia

At first you chase the Silicon Valley unicorn exit because that's the thing that's top of mind for you. But now, I am motivated by watching other founders' success. As someone who coaches entrepreneurs and founders, watching them go from A to B, maybe not A to Z, but baby steps is exciting for me. Understanding that as you mature in the industry and the time frame of your life, different things become important at different time frames. 10 years ago, the unicorn tech exit was the north star that we all wanted to get to. As time changes, your opinions about things change, and for me, it's more about watching the next generation come up, seeing how they're able to navigate and making sure that I'm impactful to that journey.