SHAN-LYN MA: Two of my very good friends met each other and fell in love at the French Laundry while working for Thomas Keller.

BERMAN: The French Laundry is a world-renowned restaurant in California’s Napa Valley, operated by chef Thomas Keller. And that’s Shan-Lyn Ma, who, as founder of the wedding business Zola, may know more stories about romantic couples than anyone you know.

MA: So, of course, when it came time to decide where to have the wedding, they had their wedding at the French Laundry. But it wasn’t the most memorable wedding because of that, although, of course, the food and the destination were incredible.

I would say it was memorable because the after-party was at a dive bar down the street, where typically the bride and groom enter in some dramatic, romantic, beautiful way. They entered the dive bar, falling on top of each other, literally, because perhaps the wine was a bit too excessive at the wedding. But it was just that combination of going from one extreme to the other that showed that no matter where you are, there’s a lot of love, both in this couple, in this wedding, and everyone around them. And so, it was an incredibly fun, special wedding, and one of those that sparked the idea for Zola.

BERMAN: Early in her career, Shan honed her product and e-commerce skills with tech juggernauts like Yahoo and Gilt.

Now, as co-CEO and co-founder of the online wedding planner Zola, she has helped over 2 million couples start their lives together.

I’m Jeff Berman, your host.

In this episode, Zola’s Shan-Lyn Ma shares lessons about how intrapreneurship prepared her for striking out on her own, finding clarity in a personal crisis, and weathering pandemic-level disruptions to her business.

But first, I wanted to talk to Shan about the earliest inspiration for her entrepreneurial story.

Shan, welcome to Masters of Scale.

MA: Thank you for having me.

What drove Shan-Lyn Ma to entrepreneurship

BERMAN: I’m thrilled for you to be here. A lot of the Masters of Scale we have on the show started their entrepreneurial journeys early. How did you get the bug? How did you get started as an entrepreneur?

MA: Well, I have wanted to be an entrepreneur before I even knew the word existed. I was born in Singapore but grew up in Australia, where my family moved when I was four. And I think I realized very early on that any money my parents had, which wasn’t a lot, went to school and books and not much else. So anything else that I wanted, I had to earn for myself.

And so very early on, I kind of learned — or caught the bug, I should say — of creating something out of nothing. And that is truly addictive, not just the fact that you get to earn something, but the fact that you created something out of nothing. I think that is still the most fulfilling part of my job.

BERMAN: I grew up mostly with posters of athletes on my wall, including a famous poster of a basketball player named Darrell Griffith, whose nickname was Dr. Dunkenstein. I still remember that poster on my wall. You grew up with a very different kind of hero on a poster on your wall. Who was on your wall?

MA: Well, there were two very different people on my wall. One was Kylie Minogue, who I wanted to be like. The other person was Jerry Yang, the founder of Yahoo, who I also wanted to be like.

The entrepreneur who motivated Shan

BERMAN: So how does Jerry Yang end up on your wall as a young woman with the entrepreneurial bug in Australia?

MA: Australia is a very remote country in that it’s literally on the other side of the world from the U.S. and surrounded by water. So my window was really magazines, which ended up being business magazines, which was what the library had at the time. And so I would read about all the exciting things that were happening in the world.

And this story of Yahoo was one that really caught my imagination. Here was this young person right out of school who was finding a way to democratize information and make it accessible to everyone. And by the way, he did it in a very fun, down-to-earth way. And he also looked like me. It made me feel like that was something that I would like to do one day.

BERMAN: Shan was laser-focused on getting to Silicon Valley, so when she had the opportunity, she enrolled in the MBA program at Stanford.

Soon after, she got an internship at Yahoo, and then a full-time job. The man on the poster in her childhood bedroom was now signing her checks.

MA: There were so many things I learned at Yahoo, but the most exciting moment for me was when I walked past Jerry Yang in the hall.

BERMAN: Did you get to tell him about it?

MA: No, obviously I was too stunned and shocked and starstruck. And so, he was very busy, clearly very stressed, with a lot of things going on at that time in Yahoo. But I walked past him, and then I think I just stopped in my tracks and maybe had a small panic attack.

BERMAN: Have you had a chance to talk to him since?

MA: I have, I have. It was incredible. I think he was everything that I imagined he would be, in terms of being kind, humble, obviously extremely smart, and I feel so lucky to have had the opportunity to meet him. And part of what gets me up every day is the motivation to be able to show Jerry that I can one day write to him again and say, “Look at the things I’ve done. I hope you are proud and what you’ve inspired.”

Lessons from Gilt

BERMAN: About a decade into her career, Shan landed what became a transformational role at the website Gilt.

MA: For those people who might not be familiar, Gilt was one of the earliest, I would say, web 2.0 startups based in New York. It was at the forefront of a new wave of e-commerce and shopping experiences, both on the web and on mobile.

I came across Gilt at first as an early customer. I was looking, and I thought, “Wow, I can’t stop coming to this site. There’s something special happening.” I saw the team page and thought, “These are people I would love to work with and learn from.” I was lucky enough to get the job as the first product manager there.

I feel like that was one of the best decisions I’ve ever made.

It gave me the opportunity to have a seat on the rocket ship, which I think is a phrase that Sheryl Sandberg coined, where it was about 30 people at the time, and four years later, over 1,000 people. It was doing close to zero in revenue at the time. Four years later, over $600 million in revenue.

And so I got to have a front seat on developing all the new products that would drive that expansion. Because when you’re in such a fast-growing company, there’s a lot of opportunities to do things you would never be able to do otherwise, including coming up with ideas and having the chance to execute them if they’re good ideas.

The moment of frustration that led to Zola

BERMAN: So, having taken those lessons from Yahoo through Gilt, where did the idea for Zola come from?

MA: It was really born out of personal need. In 2013, which was the year we started Zola, all my friends were getting married at the same time. Many people have that year where every weekend you’re going to a different wedding, spending a lot of money, traveling a lot, buying a lot of gifts. I was buying a lot of gifts from my friends from their wedding registries.

And I distinctly remember there was one friend where the only thing I could afford on her registry was one silver spoon. I called her up, and I said, “What is going on with your registry?” And she said, “Oh man, I don’t even know. It was so frustrating to put together, I just let my mother deal with it. I don’t even know what’s on there. The whole thing is just so painful and horrible.”

And that kind of set up a lightbulb, because here I had been working on creating simple, fast, fun e-commerce shopping experiences, and suddenly I was faced with one of the worst shopping experiences I’d ever seen online. And so I started talking to Nobu, who is my co-founder here at Zola, and we had been working together for a long time.

And I was saying, “This is kind of crazy. It’s like stuck in the 1900s. Our friends deserve better.” And Nobu was married, and he said, “Oh, it’s just as bad for guests but also for couples. Everything that you have to do to set up a registry is one of the worst parts of getting married.”

We heard again and again that people wanted fundamentally different things than what they were getting from department store registries, which dominated the market at the time. They wanted to fully personalize their registry and their entire wedding, and they just wanted the convenience of managing things where and when they wanted them. And no one else was doing that.

And we thought, “We have been doing that, just at a different company, and we can bring very unique insights to this problem.” And we kind of looked at each other, and we said, “We should do something about that.” And that was the beginning of Zola.

What Zola got right — and wrong — early on

BERMAN: So almost every company, when they start out, they get some things really right. They get some things really wrong. What did you get right, and what did you get wrong at the beginning?

MA: So, my co-founder Nobu and I are very much product people. We are focused on the customer, the couple, and we believe the best product always wins. And so, I think what we got right was laser-focusing on, “How can we design and build the best possible product for couples?”

And we also didn’t want to distract ourselves with doing a lot of different products or features until we felt like we had really nailed the first one, which was the wedding registry.

Now, I think what we got wrong was that maybe we waited a little too long to respond to couples’ requests to expand beyond the wedding registry. We spent the first four years on that one product, but we heard from day one of launch, “Oh, could you please help me with this in my wedding planning? Can you also help me with my wedding website?” Because my registry really has all my information. “If I could just add a few more things, it could all be in one place.”

If I could do it all over again, I would react faster to those couple requests.

When to expand to other product lines

BERMAN: But there’s a tension, right? Because you want to nail the one thing, you want to get it really right before you start expanding. And yet, if you’re not serving your customers’ broader needs, you risk losing them to competitors. So, when other entrepreneurs are coming to you and they’re asking you about this, how do you advise them about when to branch out into those next product lines?

MA: When you can start to see, both in your product feedback and in your P&L, that you have that word of mouth going, that you have that viral network effect, which is inherent in weddings. But once you see that, that is the time when you can continue to invest in that core product but also consider, “Oh, are there other things that we can then add on that are accelerated by that word of mouth?”

Inside Shan-Lyn Ma’s fundraising journey

BERMAN: Talk about your fundraising journey, if you would. When did you decide to go talk to investors, and how did they respond when you brought Zola to them?

MA: So, I always tell any founder or aspiring entrepreneur that every fundraising journey is completely different from anyone else’s, and ours fits that exactly. So Nobu and I, once we had quit our jobs and started working on Zola, we started talking to Kevin Ryan, who is someone we knew very well from Gilt. He is a well-known founder, investor, entrepreneur.

And because we worked with him for so long, we were just used to kind of sharing ideas, getting feedback on those ideas, hearing his thoughts. I still remember his words to this day, which were, “I’ve always wanted to do something in weddings. Love to work with you guys again. Why don’t I just give you the funding, and we’ll do it together?” That sounds like a dream, right?

BERMAN: Sounds great. Problem solved.

MA: Every single founder I talk to says, “Wow, that was the easiest fundraiser I’ve ever heard.” And in many ways, it was the quickest fundraising story. But I consider it more as one of the longest-running fundraising stories in that Nobu and I worked with and for Kevin at Gilt for four years. We worked our butts off, 24/7, to really show that we were people worth investing in again.

And it was only because of that history of the track record performance that Kevin had the confidence to say, “Let me do your seed round,” and we were off from there. The week before we were about to launch, I remember we started to get outreach from investors who were interested in meeting us to hear what we were working on. And once we showed them the product that we were about to launch, they sent us a term sheet the same day.

And so, again, it was a matter of, “Wow, that seems really easy.” But in fact, it was all the work that we had put into developing the product that we were about to launch that made them want to invest. Now, I wish every round was as easy as that, and it certainly has not been as easy as that.

BERMAN: What’s gotten harder?

MA: Well, I would say once you start to drive revenue, have real metrics, of course, the fundraising pitches shift from being all about the dream and the vision and that market opportunity to being about, “What has the business done? What is it going to do? And how much money is this going to earn me?”

There are some years where it’s very easy to tell that story, and then there are other years where you see the revenue is coming, but it’s just not immediately apparent on the books. And those are tougher fundraisers, and we’ve certainly had those. So what I will tell anyone who is kind of experiencing a tougher fundraise is that you just keep going until you can’t anymore.

BERMAN: Yeah, I mean, this is one of the paradoxes, right? It’s like if you’re pre-product, it’s all in the promise of the product. If you’re pre-revenue, it’s on the promise of the revenue. If you have revenue, it’s on the revenue. But like if you’re in growth mode, they’re less focused on the bottom line. Once you’re getting close to profitability, now they’re focused on… The goalposts move as you move down the fundraising field, and it can get harder.

Inclusivity around same sex marriages

You all made a decision early on to be inclusive of same-sex couples. What was that decision like for you all? Was that something that required a lot of discussion? Was that an obvious thing? Was that something investors were worried about or in favor of?

MA: It wasn’t even a decision or a discussion. It was something so obvious that it was offensive to us that no other wedding company was being inclusive of any type of couple. The default was always, “What’s the bride’s name? What’s the groom’s name?” The default was, “Oh, it must be a bride and a groom.”

It was quite frankly offensive that that was even still in existence. We thought, “Well, why don’t we ask? We say, ‘Who is getting married here?’” And then we change the experience that we’re showing to someone to reflect what people have told us.

And I cannot even describe the outpouring of love and messages that we received when couples said, “You know, it made me cry when you showed me a groom and a groom’s picture because no one else has.” And it kind of helped us know we were on the right track, and we need to do it everywhere we possibly can to show that we are for all couples, not just in the product, but in our marketing, in customer support — every single place that we can.

BERMAN: Has there been negative feedback for that?

MA: There was one instance where the Hallmark Channel refused to run our ads that showed same-sex couples.

BERMAN: Wow, remember what year it was?

MA: I think it was around 2019.

BERMAN: Oh wow.

MA: Not the 1800s, right? And at this point, we had been running ads with same-sex couples on different platforms for years, and thought nothing of it. It’s just the way that we operate. But this was the first time that someone said, “No, we’re going to run these three ads, but we’re not going to run these three ads.”

At first, we didn’t understand why, and then we looked at the ads, and the only thing that was different was the ads that were rejected featured same-sex couples. So, we asked, “Is that the reason?” And the answer was yes.

And the thing — one of the things I’m most proud of in Zola’s history is that the marketing team knew that was not okay. They knew that it was unacceptable and that Zola as a company would reject that answer. And so, they told people. They told the press. And it was an important moment for us because by standing up for what is very core to the company, we showed our couples and prospective couples, everyone, who we are. And it ended up attracting love not just from couples but also from our team, who said, “Thank you for doing that. I want to work here. I want to continue working here because of this.”

BERMAN: Still ahead, we’ll hear how Shan survived a crisis in her personal life that brought clarity to her business. Plus, she’ll share her insights on navigating the most stressful period in wedding business history — the pandemic. Stay with us.

[AD BREAK]

Welcome back to Masters of Scale. You can find this conversation and others like it on our YouTube channel.

How a near-death experience fueled Shan

I want to just take a half step back because a few years into the Zola journey, you, I believe, were in an accident. Can you tell us about what happened?

MA: Yeah, so I was coming back from California, where I was speaking at a conference, and I was in a ride-sharing service on the way home when all of a sudden, the driver ran a red light and — a car slammed into me.

And in that millisecond of extreme pain, I remember the exact thoughts that went through my mind, which were: One, this is it, I’m dying. It’s all over. And two, I’m not done yet. I cannot die today. I’m not ready.

Specifically, the two things that I thought, “I need to get these done first.” One was, I would like to have a child. And then the second is, I need to get Zola to where I know it can be, to fulfill this potential of this company.

And while what happened after that was something that I would not wish on anyone, when it comes to the amount of broken bones and pain and recovery and trauma, the way that I was able to get through that was to think about, well, I know now, it’s very clear to me, the things that I really do want to do.

And sometimes as a founder, when you’ve been working on a business for a while, you start to think, “Would I like to do something else?” And that moment was very clarifying for me because the answer came back very clearly, “No, this is what I need and want to do every single day.”

And so ever since then, I feel like my personal mission is very clear. And every day I need to continue to push Zola to where I know it can get.

How Zola survived the pandemic

BERMAN: Between that accident and today, we had a little pandemic, a once-in-a-century event, which, for some businesses, like Peloton, pulled their business forward incredibly. But you’re running a business that supports people gathering in person. So I want to go back to March of 2020. What was it like being at Zola then, and how did you manage through especially those first few months of the pandemic?

MA: One of the reasons that we were so excited to do something in the wedding space in the first place was because when we looked at decades and decades of history, we saw the number of people that get married every year is remarkably consistent. Through depressions, through boom times, no matter what the decade, it’s a very consistent number every single year.

Even as the culture changes, people still want to get married — except for when there’s a pandemic and you’re not allowed to leave your house. And that was probably the darkest year for the wedding industry overall, certainly for us.

We could see very quickly as couples removed the wedding dates on the wedding websites. With Zola, we had kind of three things that we knew we had to do, and we thought, okay, this is clearly going to be a make-or-break year or month for us. What are the things we need to figure out?

The first was, how can we support our couples, who are clearly going to be in a lot of pain, because they don’t know what’s going on. They don’t know what to do. They, in some cases, have put down large deposits.

And so, we started building products and features that would support couples during that time specifically.

BERMAN: Can you say more about that? I mean, so, I’ve got a venue booked, I’ve got a honeymoon planned, I’ve got guests coming in, all of it, and all of a sudden, the world is shut down. So what are the tools you’re giving people to manage that?

MA: So, we started talking about, “You might want to change your date. You might want to change that booking.” And what are the ways we can support you to do that? Well here’s exactly how you do it via your wedding website and other Zola products.

Here’s how you message that to your guests in a way that hopefully people can really hear. And then for those that have bought “save the dates” or wedding invitations with us, let us help you send out free “change the date” cards. And so, that was one example.

The other example was, okay, maybe you just really want to get married on that same day. So, here’s a virtual wedding feature that we put up very quickly. And then here’s some other vendor recommendations of things that might be more supportive of the type of wedding that you might want to have now or later on, potentially with fewer people.

BERMAN: And in the meantime, your own team, you’re not gathering in the office at that point, so you’re figuring this out for your customers at the same time you’re figuring out how to lead a team that is all of a sudden working from home. How’d you do it?

MA: So, I would say that we made the decision to focus on two things that I think helped limit the distraction and the, what we call doom-spiraling, that one could have gone into mentally. I think the first was, let’s start to build out scenarios of what could happen.

Let’s start to build out scenarios of what could happen. So, we had a “What happens if the pandemic lasts three months? What happens if the pandemic lasts six months? And let’s not even imagine what happens if the pandemic lasts nine months — lord forbid that.” And that then helped us create some very quick decisions around things we needed to stop and start doing.

So, for example, up until that point, we had heard feedback from couples and started to see in our data that a lot of people are buying for their home because the home category at that point was booming. So, we very quickly launched Zola Home, which is essentially a kind of home website where you could buy anything you need for your home. And that was one of the things that helped us get through that year.

And then, of course, the following two years were the biggest years ever for weddings, where a lot of people who might have pushed their wedding back or pulled their wedding forward decided, “We are going to celebrate being back in person again, and we’re going to have a really big wedding.”

Zola’s growth strategy

BERMAN: So, as we sit here in 2024, you added Zola Home in the pandemic, you had this experience at Gilt of beginning to expand into new business lines and what have you. As you look at growth ahead for Zola, what’s next?

MA: Well, there’s still, first of all, a lot to do in weddings. So, we will continue to grow and build upon the weddings product portfolio that we have. But we’re excited about being a life stage company and thinking about couples. Once they get married, they still actually do come back to Zola. They still kind of ask us to help them with more things that they think we’re well-suited to do.

And so, our recent launch of Zola Baby is a good example of that, where actually, from probably the first day we launched Zola, we also heard requests for, “Oh, can I use this for my baby registry?” And it took us 10 years, but we finally decided it was time to do that.

And so, that now I think kind of puts us into the “We serve you from engagement through this entire life stage of really kind of growing up, creating a family, and all the parts of this life stage.” It’s everything to do with a couple and their relationship together, and how can we best support that?

The wedding gift that every couple wants

BERMAN: What is a non-obvious, unusual wedding gift that you saw, or that you’ve given, or that you’ve liked? What’s one thing that people should think about giving as a wedding gift that they might not otherwise think about?

MA: Every registry, towards the end, there’s a bunch of things that people aren’t as excited by, and one of those things is a Dyson vacuum cleaner. And as a guest, I understand — I don’t really want to gift a vacuum cleaner either. It’s not one thing that you want to walk into someone’s house and say, “Oh, I feel so great because I gave you that vacuum,” right?

But every couple always says, “I really hope someone gets me that vacuum cleaner because I’ve always wanted a Dyson, but I’ve never wanted to spend that for myself, but I would love to get it.”

BERMAN: Well, James Dyson was a guest recently, and not a sponsor of the show this week, but he’ll be very happy to know that the Dyson vacuum cleaner should be the number one item that people buy or contribute to buying for their friends who are getting married. I love that.

How Zola is leveraging AI

And we’ve entered this world of AI, and you all launched a Split the Decisions tool. Can you tell us about that?

MA: What we heard consistently from couples — mostly heard from brides — is that there’s one person that does all the work in putting together a wedding, and they really wish it was more fairly distributed.

And so, we put together this tool that asks you a few questions, such as “What are you each strong at? What are you interested in?” and then kind of divides up what are the responsibilities that you can both take on in planning this wedding together because you’re getting married together.

It was something that started as a fun idea, but we’ve really been surprised at how many people have embraced, tried it out, and continue to see a lot of positive feedback on that.

The other thing that we also launched was a “thank you note generator,” because one of the most painful things after you get married is that you have to send a lot of thank yous to people who came to the wedding or gave you a gift.

And we thought, well, this is something that is very easy to generate if you know who gave you which gift, and you know their contact information. And if you know you can, as a couple, put in what kind of tone you might want that thank you note in. And now, we can just help you generate that. And then you can imagine, over time, just click a button, send the note, and you’re done.

Shan-Lyn Ma’s favorite part of her job

BERMAN: Yeah, tons of applications. What’s your favorite thing about what you do?

MA: It’s still the thing that I started doing when I was very young, which is working with a group of smart, fun people to think about new ideas that will make other people happy. Working on getting that idea out into the world, and then seeing if people actually want to use it and love it.

And there is nothing as satisfying as when someone who used Zola comes up to me and shakes me by the shoulders and says, “You don’t understand how much I love Zola. I love Zola.” I say, “Well, thank you. I really appreciate it.” And they say, “No, no, no, no, no — you don’t understand. I love it.”

And that passion is what I’m always looking for, for anything that we do, because it means that we have done something truly different. Still the moments I live for.

BERMAN: Well, that’s a wonderful place to bring the conversation to a close. Thank you for being with us.

MA: Of course.

BERMAN: Zola has built a better experience for millions of people around a key milestone in their lives. And Shan’s commitment and clarity in the face of crisis continue to fuel Zola’s growth.

And if that isn’t something worth raising a glass to, I don’t know what is.

I’m Jeff Berman, thanks for listening.