Do We Stay or Do We Go? Interview with Jade Leaf Matcha, Mindful, and Clean Break Nutrition Co-Founder, Marc St Raymond
This week’s interview is with Marc St Raymond, co-founder of Jade Leaf Matcha, Mindful, and Clean Break Nutrition. Marc and his partner, Will Crowthers, launched Jade Leaf in 2014. What had begun as a creative side hustle quickly turned into a full time thing. Together they turned Jade Leaf into the top selling brand of matcha in the United States. After six years in business, they took a step back in 2020 and asked the question: Did they want to try and take the business to the next level or was it time to sell? Ultimately, after lots of thoughtful soul searching and analysis, Marc and Will decided to sell the business. Marc completed his two year earn out in 2022 and spent the next two years intentionally being an “unemployed free agent” as he pursued the parts of his life that he’d put on hold. In that time, he met his now wife, settled in Austin, got a puppy, and revisited ideas that had initially been sparked during the early years of building Jade Leaf. Those ideas have taken the form of two new companies: Mindful and Clean Break Nutrition.
I was inspired to reach out to Marc in pursuit of answering the questions: What’s it actually like to decide to sell? What is the mental experience of navigating what comes next after devoting such a big chunk of life to building a business? How is he approaching things differently the second time around?
We spoke about all of that as well as:
The three questions he and his cofounder asked themselves to navigate the question of whether or not to sell
How being all in on one business can feel like placing all your chips on a single bet at a casino
Intentionally taking the time to invest in all the things that had been put on hold while he was building Jade Leaf
The mental framing that’s allowed him to get comfortable with ambiguity
Managing the fear of “Will it all go away tomorrow?”
The importance of reducing friction in creating consistent habits
Note: The following interview has been lightly edited for clarity and length. While every effort has been made to preserve the integrity of the conversation, please be aware that the quotes may not be verbatim but reflect the essence of the dialogue.
How would you describe your career background and what you do for work?
I think career is sort of a funny word for a lot of the folks that end up on entrepreneurial paths. The concept of a career suggests that there is a pathway. The idea that if I do this, eventually it'll lead to this linear path that makes sense. I’ve never really thought about it that way. It's been a combination of trial and error, being curious about a lot of things, and always trying to bring something new to the world.
I am entrepreneurial, but I haven’t necessarily always been working on or at a startup. Necessity is definitely a factor. I've held jobs at various times to pay the bills or to try and learn something. Over the years, I’ve learned that I’m definitely a zero to one type of guy. I really like living in the ambiguity of not necessarily knowing where something's going and having your work change a lot day to day. There are pros and cons to that. You don't hone any particular skill and end up being a generalist. That said, I like being a generalist and having side projects just to see where they go. It’s a bumpy road, but one that I've been lucky enough to find success in. If you can make it work and be comfortable with the ambiguity, entrepreneurship can be a really fun path.
You spent nearly 8 years building your last business, Jade Leaf Matcha, before the business was acquired by a private equity firm in 2021. What’s the most honest way you would describe going through an acquisition process and deciding to exit?
It was eight years end to end including the sale. The meaningful building of the business took place over a six year period from 2014 - 2020. It was a mixed bag of emotions when we decided to exit because we had so many different lenses we’d viewed the business through over the years. In the beginning, it was just a side project, and then it gained steam and became something that was much more successful. Our thinking changed on it a number of times, but by the end we’d come to a point where we had been working on it for a while and were at the juncture of asking: Should we continue down this path or do something different? We asked ourselves three questions. The first was: Is this our life’s work? Do we feel like this is what we put on this planet to do? We said, “No. We love this, but we are interested in numerous other things. This isn’t what we were ordained to do forever.” The second question was: Is this a family business? Is this something we're going to maintain and pass on to become a generational endeavor? That’s a whole another topic, but we said no to that question too.
At that point in 2020, we saw ourselves as having built something meaningful; a product that a lot of people loved and a business that was healthy and doing well. The third question involved thinking about what it would take to get the business to that next level. We decided that we would need more validation to figure out if it truly made sense to put in the time and effort necessary to do that. We initially went out to try and raise money. We had lots of conversations but none of them panned out. We had an incredibly healthy, profitable business but it didn’t have the room to grow in a way that an investor could participate in, given their motivations to find things with a path to a 10x. At least in 2020, it wasn’t clear that the matcha market had that kind of upside. We were already the largest seller of matcha in the US. Where could we go from there?
We understood that investment wasn’t a possible pathway to this moonshot version of what Jade Leaf could be so we took all of that into account and started to think about the personal factors at play. My partner, Will, and I had invested all of our time and personal wealth into the business. Having all of our chips in one place was a scary place to be. It felt like you're at a casino and all of your money is sitting on the table in one big bet. Even though the bet looked good and the odds were good that we could continue to grow, it was hard to not consider all of the aspects of life that had been on hold because all of our chips were in one place. After thinking about all of that we said, “Let's actually try to find a buyer for this so that we achieve that financial freedom we've always dreamed of and have that peace of mind that the financial aspect of our lives is taken care of. We’ll have resources to do other things now without the fear of losing it all.” So that's what we did. We engaged a banker and eventually found a private equity firm that had an approach we liked and made an offer that made sense to us.
You stayed on for a two year earn-out. What were those initial weeks and months like for you after you officially left the business? What was it mentally like to navigate figuring out what would come next?
It was an interesting time. There were little bits of regret that would pop up here and there. That feeling of “Oh, did we make the right choice? Should we have held on to it?” You inevitably ask yourself those questions over and over again. Reflecting on that now when I consider why we sold and how it played out, it feels like the right call personally. Were I to be in my position now where I have more comfort that other parts of my life are taken care of and I have this financial freedom, I probably wouldn’t have sold.
It’s obviously a vastly different scale, but I remember Mark Zuckerberg talking about an enormous offer he got for Facebook early on. Something crazy like a billion dollars where he’d be way more than set for life at age 22. His framing of why he turned those offers down really resonated with me. He said something to the effect of, “Well, what would I do with that money? I would probably go start another social network, and I already quite like the social network I have.” If the circumstances were different, I would probably still be working on Jade Leaf to this day. I hope to recreate a business that was as successful and fun to work on as Jade Leaf.
How did you land on what you're working on now? I have to imagine it wasn’t a linear process of, “Oh, I’ll just go do this thing now.”
It was a journey of being able to be more patient and really understand what I want to do and getting my life in order in other ways. There were 2 years of earn out where I was effectively working for the purchaser of the business. It was a big change to go from a scrappy startup to working in a more corporate environment with a bigger team and all the dynamics that go with it. Over the two years since I left at the end of 2022, I have effectively been an unemployed free agent. It became a time for me to try to catch up on the parts of life that I’d delayed, like pursuing relationships and finding a partner. Everything has an aspect of luck to it. There's no guarantee you’re gonna find that partner even when you set out to do it, and there’s no guarantee that your business is going to do well even if you go into it with really good intentions and a lot of effort. So there's always some luck, and I recognize that. But sure enough, I did get lucky. Not long after really putting the effort and intention into finding someone, I met my now wife. We met in mid 2022, right towards the end of the earn out days, dated over that year, got engaged shortly thereafter, and got married in January of this year. We’ve since settled in Austin where she's from, gotten closer to the community she’s built from growing up here, and built relationships with a lot of great people in the local entrepreneurial community.
On the business side, I knew I still wasn't interested in going to work somewhere. Even being in the somewhat small corporate environment of the acquiring company really reinforced that for me. I know I’m a zero to one person. What I've started to pursue in these new endeavors are essentially ideas that had their spark during the Jade Leaf years but weren’t related enough to what Jade Leaf was doing to pursue. So I put them on hold, and I think that's been really healthy because it has acted as a gut check. I definitely fall victim to the stereotypical entrepreneurial thing of having lots of ideas where there's a sense of urgency to them. That’s not always wrong, but it's often misguided when you’re in the headspace of, “Hey, I have this idea, and if I don't start it now someone else will, or if I even tell a single soul, they'll go do it because it's so good.” You need both good ideas and good execution. In this case, I was able to be patient with these ideas and observe them as the years would go by. Some of the ideas I’m working on now were ideas I first got excited about 4-5 years ago. No one's serving the need in the way that I’ve identified, which leads me to believe that there is genuine value in what we’re building and that the ideas are worth putting out into the world and seeing what happens. I’m a big believer in getting a prototype out in front of people, getting their reactions, and seeing if they pay for it. That is by far the best way to vet something, and that’s what I’m currently doing. As of literally a week ago, I’ve bifurcated my idea into two different brands. There’s the Clean Break Nutrition brand and then what will soon be a separate company called Mindful.
You’ve spoken about being comfortable with the unknown and ambiguity. That is not an easy thing for most people to get comfortable with. What’s the mindset or mental framing that’s helped you build a positive relationship with ambiguity?
I was reading your interview with Slate Milk co-founder Josh Belinsky and really resonated with what he said about personal circumstances playing a big role in allowing him to pursue building a business. That was a big factor for me too. I had a stable family and an upbringing that was relatively comfortable. It was your classic suburban story of going to public school and getting to go to college. That made it easier for me to pursue things without the fear of, as Josh put it, “Not falling flat on my face.” No one does anything alone and circumstances can definitely make pursuing entrepreneurship much more difficult and psychologically harder.
From a mindset perspective, a lot of my ability to take this path has hinged on not having hard expectations or beliefs about what I should do in life or where I should be. I think that can be tough for a lot of people depending on their upbringing. Maybe your parents are your primary prime reference point and they got married at age X, had you at age Y, and followed Z career path. I do credit my parents for not trying to push me one way or the other or be prescriptive about what I should pursue in life. They really instilled a mentality of “Go explore. Go figure things out. You have the privilege to be able to do that, and you've created relationships that can support you along the way.” That said, I am very jealous at times when I look at friends of mine, or just people that I see in the world, who do seem to have more of a defined path. Those people who seem to have had a sense of, “I’ve always loved this and that’s going to be my thing.” I have a friend that took a more traditional path, got married to his high school sweetheart shortly after college, and is as happy as a clam. I don’t think that could have been my path, but I think it’s amazing that he had that clear understanding of what he wanted and pursued it. To the extent that you can really believe that there isn’t one right way to do life and not compare yourselves to people who are on more defined paths, it becomes easier to be okay with not knowing what you’re doing. I think accepting that is a key piece of being entrepreneurial.
I do want to look back on your entrepreneurial journey to date and reflect on some of the lessons learned. Failure is understandably a major fear for a lot of people. However, success can also be its own kind of trigger for fear and self doubt. “This is great!” can often be followed by a debilitating case of, “But how will we top this? How will we reach that next milestone?” I believe Jade Leaf successfully doubled in size every year for the first five years. Did you ever experience fears or doubts around where future growth would come from? If so, how did you work through those moments?
Jade Leaf’s largest distribution channel was Amazon. I feel like it's gotten more stable and predictable now, but I'd say between 2015 and 2020 there was a lot of unpredictability. I can't tell you how many sleepless nights I had thinking about, “Oh, man, Amazon's gonna shut us down tomorrow, and this all goes away” or “Was this just a flash in the pan?” There was enormous doubt all along the way. The stress of the Amazon unpredictability was very candidly a factor in selling the business. I needed a breather from that stress. As they say in startups and entrepreneur culture, “the highs are high and the lows are low.” You're inevitably on a roller coaster.
How do you think you might manage this kind of stress differently in the future knowing what you know now?
Hindsight's definitely 20/20, and my circumstances are very different today because I know I could weather the storm now. Even still, I think I've seen enough data through Jade Leaf and other businesses that have reached some scale to feel like I really haven’t seen cases where demand just evaporates completely overnight. If you have a good customer base of people that like your product, and they're using it day to day, I haven’t seen examples where their habits and preferences suddenly change out of the blue. If people like something, there’s some inertia in sticking with it.
I think there's also a recognition that if you have a fundamentally sound business, you continue to pay attention, and you're opportunistic, you’ll likely be able to pick up on changes in market preferences and adapt to them. Who is better positioned than you who has cash flow, a giant email list, a social media following, and subscribers? You’re better positioned than you think. You have resources, a platform, and are not completely at the mercy of someone just coming over and eating your lunch without you being able to do something about it.
I listened to an interview of yours on the Success Unfiltered podcast where you shared that one of the biggest pieces of advice you would give to your younger self was recognizing the importance of good habits and routines. You said, “They seem extraneous to your business and seem like taking time away from it, but they actually sharpen your axe and make you more productive in the long run.” Still, it’s easier said than done to prioritize these types of habits. Have there been any major breakthroughs that have helped you prioritize healthy habits more consistently and effectively?
Habits interest me ceaselessly. I think we are the sum total of our habits. I love James Clear’s Atomic Habits. I can’t say that I follow everything he says to a T, but one thing that has really worked for me is removing friction. Even the tiniest barrier will make an enormous difference as to whether you continue to do something or not. If there's any little bit of dread, you probably won’t make something a consistent habit. As one example, I cannot maintain a gym workout routine if I have to drive to it. I think the only habits we keep are the ones we look forward to, and if there's anything you don't look forward to, inevitably consistency will drop off.
The ethos behind No Directions is that there are many, many different ways we could live, work, and build a life. What does the life that is uniquely yours look like today?
It’s a continual aspiration to better and better daily habits. I’m not an early riser, but I do love a calm morning where I allow myself to wake up, drink some electrolytes, have coffee, and do the USA Today crossword with my puppy next to me. I find I'm just happier when I do that and recognize that I’m very privileged to be able to do so. I’m also generally trying to have meaningful work days working from my home office on Clean Break and Mindful. Beyond that structure, it’s pretty free form. Austin's got a lot to enjoy. My wife and I are continuing to settle in here and build relationships. We travel a lot. We’re also excited to build a family in the not too distant future so we're starting with puppies. We’re definitely on a “no directions” path. We don't have huge expectations around things happening by a certain time. We're not stressing about that. We're a little more accepting of taking things as they come and embracing when luck happens. I think it’s easy to look at the Elon Musks of the world and feel like you’re not doing enough, but I think you have to accept there’s no one right way to do this thing, and we’re all just figuring it out every moment of everyday, and that’s okay.