How They Made It: Todd and Elaine of Dandelion Chocolate on work and marriage

for all the people who fantasize about working with their spouse

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Hi! This week I had the pleasure of interviewing Todd Masonis and Elaine Wherry for How They Made It. They’re the masterminds behind Dandelion Chocolate, but they’re also husband and wife cofounders who met on the first day of their freshman year at Stanford (!). Both possess a very special combination of unflappability, creativity, competence and fun. They’ve long been an object of fascination and admiration for me and I’m so excited to get to ask them some questions about their work and their marriage. Some things we discuss:

• How Todd and Elaine took turns building and selling startups (with another husband/wife pair, Todd with the guy and Elaine with the woman) before starting Dandelion

• How software companies and chocolate companies are similar and different

• What it’s like working with your spouse: “I think you definitely have to have a strong relationship. It's funny because there are three times that people have told us "you will definitely break up." They said if you start a company together, you'll break up. If you go to Burning Man together, you'll break up. And if you renoate, your house, you will break up. Because those are the three things that couples never survive.”

• How to go from beginner to expert at something new: “I feel like a lot of people who start companies really worry about all the problems they might have in the future, and it almost paralyzes them. "What happens if I have 100 million users? Did I get the right servers?" That's not the problem you have. The problem is you don't have a product. For us, it was: Could we make a bar of chocolate? We made a bar of chocolate. Could we make two bars of chocolate?”

• How to know if you’ve found your Person: “In that moment, I realized Todd has good relationship skills, and I have good relationship skills. I was doing this mental formula and thought, "We both have relationship skills that are beyond our years,” and they complemented each other in different ways."

• Dandelion’s present and future

How it began

AVA: Do you want to start by giving us some background?

ELAINE: We met on the first day of Stanford. It wasn't just freshman year—we lived in the same dorm for four years in a row. I met Todd, and he asked what I was going to major in. I said music and econ. He asked why, and I asked what he was going to major in. He said, "Symbolic Systems," which was a combination of logic, philosophy, psychology, computer science, and linguistics. He said it just like that, and I thought, "Who is this guy?" All of my friends ended up being people who were either computer science or symbolic systems majors. I ended up choosing my major based on who my friends were, though I still did music for about two years.

TODD: When we were in school, it was the first internet bubble, so everyone was excited about starting companies. Then the bubble burst, and no one was trying to start companies because the economy had cratered. So we were counter-cyclical. I had started a company called Plaxo with my friend Cam and Sean Parker in 2001, the year we graduated. Sean Parker, if you've seen the Facebook movie, is the Justin Timberlake character. He used to sleep on our couch. We didn't have any money, so both Sean and I were supported by Elaine, who was the only one with a job as we started up. We wondered, "Is this really going to happen?" It was right after September 11, so the economy was terrible. Sean had started Napster, so he thought raising money would be easy, but it was a long slog. We eventually raised money from Sequoia.

In startups, you don't get nights, weekends, free time, or vacation. In 2008, we sold Plaxo to Comcast, and I stayed there for a year, which was the minimum. It was fun to see a much bigger company, but I was ready for a break. At first, the chocolate thing was just because I love chocolate, but I also tried doing other things—went on archaeological digs, took classes, traveled a bit. My friend Cameron and I took over a friend's garage and started making chocolate, essentially for fun, to see if it was possible.

This was 2010-2011. Before we knew it, we had a small chocolate factory. There was a company called Hipchat, which was a precursor to Slack, starting up in the garage we took over. We made this micro-chocolate factory, and everyone seemed to really like our chocolate. It didn't taste like normal industrial chocolate, so we decided to bring it to farmers markets. But there were no farmers markets back then that would take unlicensed food. San Francisco used to have the underground market, where everyone would sign a waiver saying, "This is experimental," and bring their products. We brought our chocolate and sold out at the first market. Everyone said, "This doesn't taste like Hershey's." So we knew we were onto something. We decided to keep going with it and build a little factory.

AVA: And to back up a bit, after you worked on Plaxo, Elaine worked on Meebo.

ELAINE: Yes, Meebo started a couple years after Plaxo in 2005. What people don't necessarily realize is that Todd and Cam were working on Plaxo, and my cofounder was Sandy, who happened to be Cam's girlfriend.

AVA: Oh, so you guys were a double couple company. That's so neat.

ELAINE: When Todd started Plaxo, I had a job, and then when Plaxo got off the ground, Sandy and I were working nights and weekends to try to do a startup. We actually worked on two startups before Meebo, and the third one actually felt like it would have traction and get funding. I quit my job, then Sandy quit hers, and Meebo had a really good run.

In 2009, Todd left Plaxo. We were growing cacao in our apartment and had done some small experiments. I didn't know I was going to become involved with Dandelion. I was doing farmers markets, branding, and many other things, but I didn't necessarily know it would be a full-time thing. When I exited Meebo and it was acquired by Google around 2012, I took two years off to decompress.

Around that point, I started becoming more involved in Dandelion Chocolate. Originally it was just helping out for a few hours here and there, but it became more and more. At some point, Cam wanted to work with Sandy, so there was a swap, though it wasn't really coordinated.

TODD: He left to work with Sandy, and I needed a lot of help. I asked Elaine to come in for just three months. That was 10 years ago.

AVA: Wow, so you guys did double couple companies, and then swapped. That's amazing. Elaine, I read your blog post where you talk about Todd asking you to help [with Dandelion] and you doing so without knowing that it would be permanent.

ELAINE: Todd and I had this idea that we didn't want to have all our eggs in one basket. Even after having been in tech before, it just felt like that wasn't super stable. At some point, we just decided to do it no matter what.

AVA: And you decided to do it because you really like working together?

ELAINE: Todd and I met when we were doing projects in college, and we're both product people. We both really like details, and we work well together. Because our relationship was forged in doing projects in college, it wasn't so weird to work together professionally. It's almost a return to our origins.

AVA: Did you guys start dating right away in college? You said you met the first day of school, right?

TODD: We started officially dating a couple months later. We knew each other, liked each other, but it wasn't for a couple months that it became official.

ELAINE: I told Todd when we were first talking about becoming official, "I'm not planning to date anybody until after grad school."

TODD: This was like one month into freshman year. I was like, "What am I supposed to do with that information?"

Software vs. chocolate

AVA: Can I ask about the biggest differences between working on a software company and working on a chocolate company? I imagine it's totally different.

TODD: Some things are similar and some things are different. The similarities are that you're starting a company from scratch. You have to build everything yourself, going from nothing and building it up. Silicon Valley in particular has a really nice culture for entrepreneurship—everyone wants to help you out, and there's access to capital and good people. So all of those things you learn as an internet startup transfer.

In terms of what's different: with software, you just start typing, and you have a company. With chocolate, everything here we had to literally build or get permits for. Imagine if you wanted to start a tech company and you had to go to City Hall and wait two years to get permission. That's essentially what happened here—we'd wait two years to get sign-off on building and all the construction.

Also, with software, you make your product once, then you iterate, but it keeps running. With chocolate, every day we make something that then goes away when people eat it. So every day we have to do the same thing over and over again. We're almost trying to make the process that makes the product more than just making the product. It's a different way of thinking.

We've been lucky to have a decent number of resources, between us and investors, to put behind this. But in general, in the tech industry, ideas get thrown a ton of money very quickly. They have the luxury of either scaling quickly or finding very specialized people with lots of resources. We have to be a lot scrappier and really try to make things work and make sense, because ultimately, we're selling chocolate bars that have certain price points. We have to get a certain scale and make the numbers work.

From hobby to high-level craft

AVA: You guys started making chocolate as a hobby and experiment. Now you do it at such a high level and are part of this craft chocolate revival, with amazing spaces and branding. Are there any generalizable lessons? How do you go from learning something from scratch to becoming super proficient at it?

TODD: I think it's about just putting one foot in front of the other and trying to make it a little bit better every day. When we do employee onboarding, I always show a photo of the first day we were open compared to now. It wasn't that great, honestly, but it was a start. You start and make it a little better, then a little better, then a little better. It's the same thing with software—when Plaxo or Meebo started, we had a blank page, and then little by little, you build and build until suddenly you have lots of people using it.

I feel like a lot of people who start companies really worry about all the problems they might have in the future, and it almost paralyzes them. "What happens if I have 100 million users? Did I get the right servers?" That's not the problem you have. The problem is you don't have a product. For us, it was: Could we make a bar of chocolate? We made a bar of chocolate. Could we make two bars of chocolate? Could we make a really good bar of chocolate? Could we sell it? Could we get a space? Every day is just slightly incremental. If you make things a little bit better than the day before consistently for a decade, you're probably going to have something pretty good.

AVA: For the first farmers market chocolate bars, were they just wrapped in foil?

TODD: We went to Paper Source and just got whatever they had off the shelf.

ELAINE: We bought a lot of Paper Source paper in those years. Whoever was doing their inventory and trying to figure out how to stock them was probably really confused about why they were selling so much cream paper.

AVA: So you'd buy the wrapping paper. And would you hand wrap the bars?

TODD: Yes, we'd cut it and found clever ways to get paper, or to get sticker stock made, like wine label stock that we could print on with mobile printers. So it would look really good, but also be low cost and short run. Normally, going to a printer means doing a big run. We tried to be clever about making it look really good—look craft, but not arts and crafts—even though there was a lot of arts and crafts. We went to the Tech Shop a lot when that existed and made many original signs there. We had to learn a lot about metal.

ELAINE: When we started, you had a lot of duct tape, and now you know how to weld.

AVA: And you guys had to make a lot of the equipment too, right?

TODD: Yes, there used to be all these small chocolate makers everywhere, and then it became industrialized. Now there's a handful of companies that make all the world's chocolate. All the small chocolate makers were gone. When we started in the garage, there were only about 10 other small chocolate makers in America. No one was buying industrial chocolate machines and making things with them on a small scale. So we had to figure out how to do it. There were good sites on the internet, like blogs where people were sharing tips and tricks. We'd build a little machine, put it on the forum, and people would say, "That's a great idea." Then they'd improve it and post their version.

It was very much a DIY home brew hacker movement that really contributed to the birth of the American craft chocolate movement. Once the barriers to entry got so low that anyone could make chocolate at home in their kitchen, suddenly a lot more people started up. Before that, if you were willing to go to Europe and buy antique equipment, it would cost millions of dollars to bring it over, refurbish it, and then make chocolate. Not a lot of people wanted to do that. That's what Scharffen Berger did—they started the whole American chocolate movement, and when they started, it was much harder. We were part of this DIY movement.

AVA: I found an interview from 2015 where you mentioned making 10,000 bars of chocolate a week. How many bars do you make now?

TODD: Now it depends. In a year, we might make half a million or so. But actually, chocolate bars aren't our main product anymore. We have a whole confections department now, with pastries, drinks, and shippable items. Our offerings have expanded—chocolate bars are just a small piece of it now, but it's a lot more than when we were in the garage hand-wrapping one at a time.

AVA: Do you still conceive the main offering as bars?

TODD: That's the core of what we do, for sure. But now we also make chocolate in all different forms. I love hot chocolate, cakes, and other things. So we're always trying to build from that core idea.

AVA: How much of this did 2014 Todd and Elaine predict? Would they say, "It went the way we hoped it would, this was our vision of the trajectory"? Or is it a surprising unfolding?

TODD: The 2014 version of us would be pretty happy with how things have gone. But there have definitely been twists and turns and things we didn't expect. The pandemic was a pretty big twist and turn because we didn't really do a lot of online sales before. We wanted people to come into the store, smell the cocoa beans being roasted, and taste it. So we sort of overnight lost all of our revenue, almost went out of business multiple times, and the whole company had to convert to basically online web developers. We survived that.

Building this factory was a bit of a debacle. It took two years to get permits, and five years total, which is a pretty long time to get your factory going. So that was a challenge. There are a lot of things that didn't go exactly the way we wanted, but we had to push forward.

AVA: Is online the biggest source of revenue?

TODD: Yes, online is the biggest piece now. Last year was the first year, besides COVID, that online was the biggest piece. But retail is still really big too.

AVA: How would you describe your respective roles at Dandelion?

ELAINE: Todd is the CEO, and I am CXO. I work with the web, product, creative, people operations, chocolate production, and design. But it also ebbs and flows—you do whatever is necessary to make sure the business is successful. I really like learning, so the X is nice because it allows things to be fluid.

TODD: We've also hired some really good team members so they can do more. Depending on what skills people on our team have, it usually ends up that we work on the stuff that no one else is doing. Oddly, now I've been doing a lot of tech stuff because we need that and don't really have it on the team. A couple years ago, it was more about chocolate production or factory build-out or architecture. Every year it changes.

Working with your spouse

AVA: What do you tell people if they ask, "Should I work with my spouse?"

TODD: Probably depends on your spouse.

ELAINE: Most people don't work with their spouses.

AVA: But I think it's a lot of people's dream to work with their spouse—it's very aspirational. It's certainly aspirational for me.

TODD: I think you definitely have to have a strong relationship. It's funny because there are three times that people have told us "you will definitely break up." They said if you start a company together, you'll break up. If you go to Burning Man together, you'll break up. And if you renovate your house, you will break up. Because those are the three things that couples never survive.

These events are very stressful. Even if you're the best person and everything's great, things are stressful. There are a lot of exogenous factors that can make your life miserable, or times where you almost go out of business, or things happen that are really stressful. When you don't work together, you have the benefit of one person doing something experimental while the other is doing something more stable. It was nice when I started Plaxo and Elaine was the stability, and she started Meebo when I was the stability. It's nice to have that balancing act. When you're all in together without working together, you better be able to get along. You have no safety net.

ELAINE: There's also the other side of things—when you're going through hard times, it's really nice to know that you have each other's backs. If I'm going to go through a hard time, I'd much rather go through that with Todd. We're both so committed to trying to do something interesting and compelling in the world. When you have that foundation, it's irreplaceable.

If I were with a different company going through a really challenging, existential time where I didnʻt have the same values, I'd probably just think, "I'm out of here." I don't know, because I've never had that test, but I think that would be so much more challenging.

With Todd, we both have the same values and shared history. We understand each other. I have your voice in the back of my head, and I know what you're going to say. I have so many little virtual meetings with you throughout the day. I'm trying to make it so that when we do have a decision to make, I've already made the micro-decisions. When something needs to be surfaced and we need to talk about it, we can, because we know each other well.

Then again, sometimes I'm super excited about something, and all I want to do at the end of the day is talk about it with Todd after dinner, and I can tell that he's just not interested.

TODD: The worst is when you wake up in the middle of the night and Elaine's talking about some problem that's going on. It's the middle of the night, I'm in bed, I really don't want to talk about this right now. You have to put boundaries in place, because otherwise it can be too much.

AVA: The upside is 24/7 shared collaboration and having each other's back. And the downside is also the 24/7-ness of it.

How do I know if I found my soulmate?

AVA: Obviously, you guys met each other very early in life, but I'm sure all your friends say, "Wow, you have such an amazing marriage." What do you say when they ask, "How do I know if I found my soulmate?" How do you know when you've found your person?

ELAINE: I think I knew that Todd and I were likely to get married during freshman year. Most people think it's like suddenly your life flashes in front of your eyes and you're overwhelmed with love, but it wasn't really like that. I liked Todd a lot, and we had been together for two or three months, which seems like such a long time when you're a freshman, which is hilarious.

I remember this moment when we were all together with a group of friends, and Todd laughed. I think sometimes you can really tell who somebody is in those moments of laughter because it's involuntary—you don't have as much control. I remember doing this little micro-study of Todd's face and seeing the underlying kindness. In that moment, I realized Todd has good relationship skills, and I have good relationship skills. I was doing this mental formula and thought, "We both have relationship skills that are beyond our years, and they complement each other in different ways." I ran the numbers in my head and realized, "I am probably with the person I'm going to marry." I went back to my dorm and wrote it down, but I never told Todd. It was just one of those wild moments where I realized, "I'm with the person I'm probably going to marry." But it was more like a math equation. I don't mean to diminish it—I would love to romanticize it, but it wasn't like that. It was just playing it out in my head, like an instant equation.

AVA: You've told me this story before, and I've thought about it a lot since then. I remember you saying the reason you knew you would marry Todd is that you both had really good communication skills. I'm curious, what does it mean to you to have good communication or relationship skills? I definitely observe that in both of you, and I can imagine it being something you were both very precocious at.

ELAINE: It's very different things.

Todd came from an amazing family. Both of his parents are school teachers and Todd was born relatively late in their lives when they were confident parents and stable people. My parents were semi-hippies, divorced, and dated a lot of people. I learned a lot by watching those relationships and seeing what worked and didnʻt work. They say that a divorce makes you more likely to divorce but for me, I think I gained a few more years of secondhand relationship skills by seeing those partnerships play out.

So when Todd and I met, we both had these different types of skills. He is stable, even keeled, and has never known anything differently. I’m naturally more artistic and tend to go all in 110% but that was tempered by early life experiences—Iʻve seen a few things and when I met him, I had a sense of what actually led to a good long-term partnership.

From my side, at Dandelion, I'm also very good at reading Todd. He has small tells where I can immediately know if something is working or not working. That's hard to articulate exactly.

But in both settings, we communicate well, and we're both kind. After you've been together for so many decades, you also know each other's quirks. I remember when we were getting together, people would say, "Couples break up after year two, after the honeymoon period," or "They break up after year seven and year eleven." I remember flying past those milestones and thinking, "I can see how that would happen here." Your relationship evolves, and you evolve as a person too.

Every 10 years, you're probably married to a different person than you expected to be. The things that do not change are your values. I know that Todd has good values, and I know that I have good values. We have those tested again and again and again. I know that if we're put in a really difficult situation, I could always count on Todd, and he could say the same thing for me.

I think up until my 30s or so, I really felt like all of my personality could still evolve, or I could become this epitome of a person. After my 30s, I started to realize there are parts of myself that are just who I am. Some of that is learning how to accept that. There are also parts of Todd that are core to who he is, baked into his DNA. When I look at my grandparents and how they interacted with each other, there's always this feeling of, "That's just how your grandmother Mary is." Now in my mid-40s, I can see, "I know that Todd's always going to be like this."

AVA: Having been to your birthday and other events, I feel like you guys do an amazing job of still really working hard to surprise and delight each other. That seems really important in a long-term relationship and maybe something that other people fall out of doing. Is that a values thing too?

TODD: I guess we naturally do it. I don't know where it came from. We would do kidnap vacations—one time I kidnapped Elaine for her birthday, and then she started kidnapping me for my birthday, and it became this whole arms race, which got pretty bad, so we had to stop. It's actually much harder to kidnap someone now than 10 years ago. We have doorbell cameras and everything's on your phone. But I think if you like the other person, you want to make them happy and find ways to do that. Growing up, I was a really bad gift giver because I'd always give gifts that I wanted, not what the person wanted. It took a long time to think, "What does this person want?"

ELAINE: It's fun. Also, we're product people, so if you're going to design something, designing your life is really fun too.

AVA: So would you say the biggest thing about finding a great partner is finding someone who has compatible relationship skills and values?

ELAINE: You really don't know what another person's values are until you've been tested. But yes, I think the fundamental values probably are the most important. Other parts of personality are going to help over time.

I also think there's so much benefit from being together early. We didn't have to spend a lot of time and resources on dating or going through breakups and losing housing. We were pretty stable from a young age. I think it would make it hard to do a startup otherwise, unless you have extremely wealthy parents or other support. We were able to support each other, which I think was a huge benefit that a lot of people don't have. Then you also get the compounding interest of building on that. If you can do it early and get the foundation right, that's a huge advantage.

Dandelion’s present and future

AVA: One thing I was thinking about is how you guys are always doing these interesting collaborations. I feel like you're constantly collaborating with other companies, chocolate makers, etc. How does that happen?

TODD: We have a small product team with some really good people. But some of the collaborations are fairly straightforward—we have the chocolate, and then we find other people we're friends with who do something really well. We ask, "Would you like to use our chocolate to do something really cool?" We have more of the infrastructure to do packaging. For us, it's more about finding other people we really like and would enjoy working with.

In some collaborations, they are doing a lot of the work themselves too. The advent calendar, for example, is something where we're trying to make it the Oscars of chocolate. We get all our friends and people all over the country to submit, then we do taste tests, and that becomes the best version of lots of different people. We do a lot of work, but everyone else also does a ton of work too.

AVA: Do you guys work constantly, or are you doing more 9-to-5 hours now?

TODD: If anything, it's gotten busier. Early on, it was definitely more lifestyle-oriented. When you just have one small factory cafe, we were there all the time, but we still had time to go out at night every now and then. We thought we were busy, but now we're a lot busier.

Dandelion is a small company, but it's also very complex because we have our own supply chain. We do sourcing, we have a full chocolate factory, we have a full kitchen operation, a second one in Las Vegas, we have a confections operation, and then we sell online, retail, and wholesale. So we have a matrix of nine small businesses under one roof, but we also have a small number of people. The whole team is probably about 100, with most people working in cafes or as chocolate makers. In terms of the corporate team, it's pretty small, so a lot of people have to do everything.

AVA: Yeah, it's a lot of work for you guys.

ELAINE: Certainly the last five years, since about 2020, COVID was really hard. It's one thing to say we work all the time, but also keep in mind that I appreciate it so much more because it wasn't a given that we were going to survive COVID. There were many times we should have just gone out of business. So there's also really appreciating the opportunity to get it right and make sure we have something sustainable that we can be proud of, and hopefully the greater community can be proud of too.

TODD: I think you can measure the stability of a company in potential company-ending events. When you first start, every week there's a company-ending event, and then you get more stable, and then it's once a quarter, once a year. I think we're getting to the point where there are two of those a year. During COVID, every week was a potential company-ending event. Now we're back to probably only two or three things a year that could end the company. We're trying to get down to one.

ELAINE: That sounds alarmist, but that's just the nature of it. There are all sorts of things that could go wrong—it could be the market, it could be a fire, it could be San Francisco issues. There are a lot of things that could go wrong.

AVA: Do you feel like you've just adapted to that? There are lots of things you could be anxious about, but you're just more used to it?

TODD: Yes, I think there's that. But we also have better systems and better preventive measures. Many chocolate factories eventually catch on fire, and we don't want ours to catch on fire, so we do a lot of preventive maintenance and make sure our ducts are clean. You have to think ahead so these bad things don't happen. But if you worried about everything that could go wrong every day, you would just be miserable. So it's like, "What's going to be today?"

AVA: Last question, because I don't want to keep you guys forever, but what's the 50-year vision? If you're building a company that hopefully will be around for 200 years, what's the dream for that?

TODD: I think we just want to be one of the most respected chocolate companies in the world. For us, it's less about scale per se, but we always want to be the best, or one of the best, and put out products that we're proud of. There are a lot easier ways to make money in Silicon Valley than a small-batch chocolate factory. We're doing this because we want to change the world of chocolate and do something special for the world—create something we're proud of. We just want to continue to do things for the right reasons.