Heather Stevenson is the General Counsel at Red Cell Partners, a venture firm that builds and invests in national security and healthcare companies using AI. Before Red Cell, Heather was VP and Deputy General Counsel at the Boston Globe. Before the Globe, she was the founder of Thirst, a Boston juice bar she ran for five years. And before all of that, she was a securities and shareholder derivative litigator at Sullivan & Cromwell in New York.
I met Heather through LinkedIn — she's one of the more prolific and thoughtful in-house lawyer voices on there — and her career is a study in how a lawyer can leave the law, run a food business through the snowiest winter in Boston history, come back into the law in a completely different posture, and pick up new domains fast enough to become a GC of a venture firm. In this conversation, we get into why she opened a juice bar instead of going to a smaller firm, the playbook she uses to learn a new practice area from scratch, why she thinks being "too nice to be a lawyer" is a category error, and what it actually takes to separate your identity from your career.
Keep reading below for the full episode and the complete transcript of our conversation.
Top Insights
Below are the highlights of our conversation:
- The Law Will Always Be There: Heather left Sullivan & Cromwell after three years not because BigLaw was making her miserable, but because she looked at the next 40 or 50 years of her life and decided she didn't want to spend them that way. The key unlock was a quiet confidence that she could come back to the law if she needed to. Most lawyers don't believe that about themselves, and so they don't leave. She did — and she was right.
- Run the Numbers Before You Romanticize the Dream: Heather and her husband joked about opening a food business for years before they ever ran the numbers. The crystallizing moment for Thirst wasn't passion — it was sitting down with a pre-populated business plan spreadsheet and realizing the costs were higher than they expected, but so was revenue. The decision didn't become real until the math made it real. Every aspirational professional toying with "I want to open a coffee shop" should sit with that.
- Status Erodes Fast When You're Busy: The first year of Thirst, Heather sometimes delivered juice through the service entrance of the same Boston law firms her old colleagues worked at. It briefly stung. But she was too exhausted running the business to dwell on it, and by the time she had bandwidth to feel it, she was already over it. The lesson: status is much easier to walk away from when you stop sitting around comparing yourself to people who haven't walked away.
- A Playbook for Learning a New Practice Area: Heather's repeatable method for picking up a new legal domain — used at the Globe for public records work, at Red Cell for corporate governance and venture financing — has three steps. First, find one expert and take an hour of their time on how to learn the area. Second, read widely from the foundational sources they point you to (briefs, statutes, Practical Law). Third, start doing the work as early as possible, before you feel ready. The expert is the unlock that compresses the timeline by years.
- Don't Let Your Career Be Your Whole Identity: Heather's parents are both lawyers, and the thing they did right was never tell her that being a lawyer was who she was. It was something she did. That framing made it easy to leave for a juice bar, easy to come back, easy to switch roles, easy to take risks. Lawyers who fuse identity and career end up trapped — they can't change roles when a role stops working, they can't lose a case without losing themselves. The fix is structural: cultivate communities, hobbies, and relationships that exist completely outside the practice of law.
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Full Transcript
Khurram Naik: Heather, it's so great to sit down with you today. We've been trying to do this for a while, so I'm glad we're finally getting around to it.
Heather Stevenson: Yes, me too. I always enjoy our conversations and it's fun to record one.
Khurram Naik: I think the most obvious way to start your story — one of the more interesting parts of your career as a lawyer and as a professional — is the fact that you owned a popular juice bar in downtown Boston. A lot of folks I talk to would say you left the practice of law to do that, and then also returned to the practice of law. Both are really interesting decisions to make. So let's start with — how does an associate in New York at Sullivan & Cromwell decide to open a juice bar in Boston?
Heather Stevenson: Yeah, absolutely. It's certainly a unique situation. I was at Sullivan & Cromwell for around three years as a litigator. I was doing mostly securities and shareholder derivative suits. And for the most part, I actually liked it. There are a lot of people who leave BigLaw kind of kicking and screaming about how horrible it's been or the sleepless nights that caused them to leave. For me, it was more a twofold situation. One — looking ahead at the next 40, 50 years and not thinking that that was necessarily how I wanted to spend my life. Not because there was necessarily anything wrong with it. My colleagues were great, the work was interesting, but the hours were long and I wasn't finding it that rewarding. And two, I was at a point in my life where trying other things really did feel like a possibility. I was recently married, but had no kids and really no financial responsibility beyond taking care of myself and my husband, who also worked. We loved food. We loved Boston, had family here, and saw a market gap for a juice bar. We had thought about other things — should I go to a smaller firm, should I go to government, should I try to clerk? But this felt like, if I was ever going to start a food business, which is something that was really interesting to me, it was the time. There would be no better time. I knew the law would always be there, which I don't think people always feel is the case, but I felt confident I could go back one day if I needed to, and that I had this great opportunity to try something new that I thought Boston needed. And so I did it.
Khurram Naik: What was the catalyst? Was there something with the economics of juice bars that seemed attractive, or was it the personal passion side? Obviously the intersection matters, but did one factor dominate?
Heather Stevenson: We certainly thought we'd make a lot of money on the juice bar, but it wasn't like we thought we were starting the next Facebook or anything. It seemed like an opportunity to do something that mattered in terms of bringing healthy food to Boston, which is not necessarily known for having the healthiest food, although it has a lot of tasty food. In a way that would create a lifestyle that we thought would be better, and would also make plenty of money — but it wasn't something we started just for the money or with the intention of getting rich the way a lot of people start things.
Khurram Naik: Was there a decision point where you remember it crystallizing? Because it's such a cliche for professionals — "I want to open a coffee shop" — there's always something like that floating around. What was the moment where you said, no, this is actually something I can do, and I'm going to do it now?
Heather Stevenson: We joked about opening a food business — we joked about a restaurant for years before we actually did anything, and it was never serious. Neither of us is a trained chef. Opening a full restaurant is very expensive, very challenging, not something we were well positioned to do. And then we were training for an ultramarathon and eating a lot of acai bowls, drinking juices and smoothies in New York and really loving it. That's when we noticed there was this gap in Boston. We were living in New York at the time but traveling home to Boston all the time. So it was a gradual crystallization of — okay, maybe we could do a food-based business. Maybe it could be a juice bar. I don't think we were totally sure we could do it until we played around with some numbers in one of those pre-populated business plan spreadsheets that supposedly helps you plan your business. It turned out all the numbers were completely wrong — both in terms of costs, which were way higher than we predicted, but revenue was far higher too. So that was good. But I think it was when we really started playing with numbers that we felt like maybe it was probable.
Khurram Naik: If you were launching the juice business today, what would you do differently?
Heather Stevenson: We saw this gap in Boston, and now, having run Thirst in Boston, I understand the reason for that gap. At least part of it is that the winters here are brutal. And nobody wants a smoothie in the middle of winter. I love smoothies in winter. I'll drink a smoothie any day of the year. I don't think I would actually do that much differently in terms of the startup. There were a lot of things we did right. There were things we did wrong along the way of actually operating it that probably could have made it more successful. But we also didn't end it just because it didn't do well financially. It did fine, but not well enough to be worth it. There were other reasons to leave. It was a drain, a stressor. We had left BigLaw to open this juice bar thinking it would maybe create a better lifestyle, because eventually we'd have managers in place, we'd have all these stores, and they would really run the day-to-day. And that was sort of true. But when a pipe bursts, nobody cares about that more than the owner. Even if the manager is doing their best, you really need to be available. Some of the reasons for ending it weren't so much a business failure as realizing I didn't want to be in the juice bar business.
Khurram Naik: It sounds like a real through-line of your career has been that you've done a good job of turning inward to figure out — how do I want to allocate my attention in my professional life?
Heather Stevenson: I think that's right. And I think what I've wanted has evolved over time a lot, which leads to the drastic changes that have happened over the course of my career — from BigLaw to juice bar to in-house, but at a smaller company, at a media company, the Boston Globe, and now to a venture capital firm, where it's a much heavier demand on my time. I believe in seasons. Seasons of life. Thirst was really good for that season. I feel really proud and happy that we were one of the first to bring juice to Boston. There are a lot of juice bars in Boston now. Some of them do really well. Some of them are new every two years. I feel happy about all of that, but also kind of glad that that part of my life is behind me.
Khurram Naik: Remind me again when you launched Thirst?
Heather Stevenson: November of 2014, which was the start of the snowiest winter in Boston's recorded history. Every Monday it felt like we had a blizzard, and our trucks couldn't get through with the fruit because you can't freeze fresh fruit all the time, or our employees couldn't get to work because the subway shut down. It was a challenging first winter.
Khurram Naik: It's so funny because my professional history is actually weirdly tied to yours. In that same timeframe — when you launched — I started going to Boston for a series of depositions pretty consistently as a litigator. I was based in Chicago. And one of the things I noticed about Boston, in part because of you, was that there were more juice bars proportionally than Chicago, which is a much larger city. That struck me — Boston, you have more juice places than Chicago. And then I ended up moving to Boston to join a firm here. So that's one bit of interesting coincidence. The other coincidence — which I think will get into the significance of for you later — comes from social media. One of your offerings at Thirst was a mango oats smoothie, which was a really unusual combination. Those were two food groups I'd never think to put together. My wife really loved your juice bar, actually loved it the most. We were seeing each other long distance and we'd always go there.
Heather Stevenson: I love that.
Khurram Naik: So I contributed for a while to a website called Above the Law. I was a pretty active contributor, really enjoyed publishing there, and enjoyed that more than publishing as a lawyer. At one point I was the fitness and endurance contributor and I had a little blurb about — I can't remember what the prompt was, but I decided to share this mango oats smoothie, which I pretended I came up with, but I'd actually learned from Thirst. And then I decided to go on LinkedIn and share that. My posts on LinkedIn had been very vanilla, classically lawyer — here's a firm update, here's a firm update. This was the first time I ever decided to put some flavor on LinkedIn. And I actually had a co-worker reach out to me about it: "Oh yeah, I love that smoothie." So in a couple of different ways your juice bar influenced me professionally.
Heather Stevenson: I love that. I also love that smoothie. Our version, the third version, was called the Peruvian Pick-Me-Up. I can't remember if you added this — but it also had maca, which I was a huge fan of at the time. It was supposed to help with energy regulation. And when I made it for myself, I would add almond butter.
Khurram Naik: I did the same — I would also add almond butter when I made this smoothie.
Heather opened Thirst the same way Silpa Maruri eventually launched her own law firm — by treating entrepreneurship as a real option lawyers have rather than a fantasy professionals joke about. Both did the math, both walked away from a defined path, both built something. Listen to my conversation with Silpa Maruri.
Khurram Naik: So let's talk about the decision to leave Thirst. Was there a crystallizing moment, like there was for leaving the law?
Heather Stevenson: It was kind of phased. In 2017, my son was born. I initially had this plan that literally everybody told me wouldn't work, but I thought would work — I would be his full-time caretaker while my husband was at a more traditional job, no nanny or support. And I'd keep Thirst running because we had managers, we had two stores at the time, managers in each location. I thought this was a great plan. And of course it was a terrible plan. I was exhausted. I felt like I was doing a terrible job as a business owner and a terrible job as a mother. So that was the first thing that happened. My husband and I talked and decided, around December 2017 — so our son was three months — that I would try and find a job around when he turned one. Thirst was not kicking off enough money to pay for childcare, but I'd be able to dedicate some time to a job, a little bit of time to Thirst, our son would be well taken care of. I was quickly realizing that, in addition to my plan being a bad one, I was just not meant to stay home full time. We had this whole plan, and I ended up just getting really lucky. Rather than waiting until he was one, I started poking around on what was available, and found something like two weeks after we decided that I would go back to work. So in January of 2018 I started as an in-house lawyer at the Boston Globe — in addition to being a mom, without a nanny. We were still running Thirst. It got to be a lot. It was actually much better than trying to be a full-time stay-at-home mom and full-time stay-at-home business owner, but it was a lot. Thirst was profitable, but also in this scary position where a few bad months could have put us in the red. So first we closed our Wellesley location because of disagreements with our landlord — we'll just leave it at that. And then at the end of our Boston lease, which was in November of 2019, we decided not to renew. Largely because I had a full-time other job, my husband had a full-time other job, and Thirst, as much as we had loved it, was causing a lot of stress. It turned out to be a very lucky decision because, as you know, March 2020, Boston shuts down for the next 18 months. It took them I think three years to get a new tenant into that space. So it was a gradual decision and evolution. There was really no light bulb moment with shutting down Thirst.
Khurram Naik: In making a decision like that — you ran into challenges with operations, with counterparties like a landlord. Are there principles you took from any of these? Categories of issues that businesses run into, or forms of conflict, if you want to think in terms of a litigator. Any enduring principles you still use today?
Heather Stevenson: I think there's a lot of lessons learned, some of which could be put into principles. One is you have to be really clear on your why — why you're doing something. For Thirst, it was this combination of passion project and it was supposed to be our job. I think we should have raised prices a lot earlier than we did, and probably should have paid our employees less than we did, although I would never have wanted to do that. But had we done that, we would have looked a lot more like other similar companies in the area, and probably would have been more profitable — maybe to the point where it would have been worth the risk to keep Thirst open. In terms of conflict, planning for conflict is something we do as litigators anyway. It's almost funny to me, some of the situations we ended up getting into with Thirst, because I know better. But planning for the worst-case scenario from day one — assuming everything that could go wrong will when you're negotiating any agreement — is also key.
Khurram Naik: Do you have a point of view on lawyers having side businesses?
Heather Stevenson: I think it's great. I think it's important to understand why you're having the side business. Being a multidimensional human, rather than just a lawyer, is really valuable, both to people's happiness and even to their effectiveness as a lawyer. It's a lot easier to make principled logical decisions when your whole identity isn't wrapped up in being a lawyer. A question I always have when someone tells me about a side business is — why? Do you do it for fun? Do you do it for money? Do you do it because you're planning an eventual exit? And then the most concerning one — do you do it because you're unhappy and you're just trying to fill all of your time so you don't have to sit with your thoughts? That one's concerning. The others, it's sort of like — you do you.
Khurram Naik: How did a former litigator who ran a juice bar end up as an in-house lawyer at the Boston Globe?
Heather Stevenson: Randomly, as it feels like my whole career has gone. As I mentioned, December 2017, I started looking around at what was available for Boston legal jobs. I had never practiced in Boston. I'd only practiced in New York. So I really had no sense even of what the market looked like. I knew I didn't want to go back to a firm. There'd been a political event, and a friend of a friend had joked, "Oh, you should come work for me." He was a GC of a local company. We talked about it and he ended up not having anything that was a good fit, but it got me on the idea of exploring what it might mean to be in-house, which was really not something I had ever given that much thought to. I saw this job at the Boston Globe that seemed cool. Having grown up in Boston, the Boston Globe is a big deal. It's our local paper, covers all the local sports, we care about it. The job itself was actually not that interesting. It was reviewing and negotiating all of their basic contracts — everything from the ink they used to print their newspapers to more substantive licensing agreements. I was mostly attracted by the brand and by the general counsel, who I knew a bit previously. I saw the job on Indeed, I think it was, and reached out. I had a connection to him — he had worked with my mom. I asked her, "Will he talk to me?" She said, "I don't know, sure, let me see." He agreed to talk to me, and his initial reaction was, "I don't think you want to do this job. I just need somebody to review and negotiate contracts. You're used to fairly complex securities litigation. You've been doing all this interesting stuff standing up your own business. I don't know if this is for you." And I was like, "I want to do it. I will do it well. I can do it. I've been negotiating contracts for bananas. If I can negotiate a contract for bananas, I think I can negotiate a contract for ink for your paper." I convinced him to hire me for significantly less than what you would pay a first-year associate — more like a paralegal. It was great. And I only did the contract work exclusively for about a month. I just kept raising my hand after that. So the job that I actually did at the Globe, which was fantastic and I loved and never really planned to leave, was nothing like the job that had been described when I first applied.
Khurram Naik: What did that job evolve into?
Heather Stevenson: When I left, I was VP and Deputy General Counsel. The general counsel by that point was also in a co-business role where he was developing their new media arm. So I was doing basically everything and anything he didn't have time for — from public records requests to overseeing someone else who was doing the regular contract negotiations, to employment work, to licensing. It was very broad and very interesting, because the Globe was at such an interesting time in its history, where the local paper in so many ways is dying, but the Globe is not — and it's finding ways to make sure it doesn't. Being part of the team trying to do that was really exciting.
Khurram Naik: These are brand-new practice areas. How did you pick up these new skills and the confidence to say, yes, I can take that on?
Heather Stevenson: A lot of it came from Thirst. I had no business starting a juice bar. I had a lemonade stand when I was five, and somehow that translates into an actual juice bar. So a lot of it was — once you figure out that you know how to figure out random things, that becomes a lot easier. I also had really good support and mentorship at the Globe, both from Dan, the GC, and from some really fantastic outside counsel — a guy named John Albano, who basically knows public records work in Massachusetts as well as anyone. He taught me in a way that I could take that over, which was a really specialized but super interesting field of work that I did a lot of. At a certain point you learn — okay, there are many things I don't know, but I know how I can learn things. That made it a lot easier over time.
Khurram Naik: Is there a playbook you can share for how you learn new things?
Heather Stevenson: If you have an expert to learn from, that is one of the best first or second steps. Take an hour with them and ask them how to learn that particular area. That is what I did with John, who gave me a bunch of briefs that had been filed with the court and said, "Go read these, plus go read all the cases they cite. And you'll pretty much be able to figure things out." That was specific to public records. An expert in a different area can give you the playbook for that. Maybe it's reading aspects of the Delaware code, whatever it is. The other way I learn is just from reading widely. Not everybody learns that way, but I do really well. I love school. I love textbooks. I love things like Practical Law. You have to get to this initial very basic level as soon as possible, as soon as you know you need to know something. And then it's just a question of starting to do. I think doing early is important as well, although you obviously need to know something before you can do.
Heather's three-step playbook for learning a new domain — find one expert, read widely from the sources they point you to, start doing the work early — is exactly the engine that Shashi Kewalramani described in his episode for compounding skills across a nonlinear career. The skill of learning new domains fast is the meta-skill behind every meaningful pivot. Listen to my conversation with Shashi Kewalramani.
Khurram Naik: You started to build a name for yourself for picking up new areas. How did you transition from the Globe? I came to know you on LinkedIn as someone who was talking about the transitions she had made. How did you come to start sharing your story on LinkedIn?
Heather Stevenson: I realized pretty early on at the Globe that I love being in-house. I would probably be in-house for the rest of my legal career, and that was where I wanted to be. I also realized that as much as I loved the Globe and didn't really want to leave, I would probably never be its general counsel, because Dan is only four years older than me. And he also loved the Globe and will probably never leave it — which is great. Having a team that is that loyal is amazing for a company. But I had a problem, because nobody in Boston knew who I was, or if they did, they knew me as the juice bar lady, not as a lawyer, the way people in New York had. So I initially started posting on LinkedIn, along with going to local bar association events, just to start to build a local network. This was pre-COVID, so people got jobs locally too, went into offices, all those things. I started just because I wanted people to know who I was, and I wanted to know who they were in the legal world in Boston.
Khurram Naik: How did it evolve over time? Because now you're prolific and known for big portable ideas. What happened on the way to that?
Heather Stevenson: I started just to meet people locally, and it turned out I was connecting with people all over the country and really enjoying it. The posts that seemed to resonate the most, and that I enjoyed the discussion around the most, were really about the bigger-picture thoughts. How do I think about being an in-house lawyer? How do I think about transitions? What's the role of failure in success? Rather than what does this aspect of the public records law mean, or how should we interpret this piece of copyright. It was fortunate, because people liked the same things I liked talking about. I've experimented over the years with posting more often, less often, commenting more, less, but I'm now at this cadence of once a week, which is enough that I think I'm still on people's radars, still getting the chance to have great discussions. I try to get on there and comment on other people's posts and meet new people more than once a week. But I'm not giving a ton of my time or energy to LinkedIn. I'm using it as a tool to meet people and learn from people. It's not really about LinkedIn. It's just a way to learn and grow in my community.
Khurram Naik: Do you have tips for other people who want to become more active there?
Heather Stevenson: For most people, just starting to talk about their personal stories is a really easy, surprisingly effective way to start to build a community on LinkedIn. Most of us — our stories feel like they wouldn't be that interesting because we lived with them. But if you actually start talking about it, you'll find that people are fascinated by them, because of the similarities or the differences or whatever it is. Sharing about your personal experience, I think, is great. Sharing about how you think about things is also really interesting, because it starts interesting conversations and allows you to build real relationships over time with the people you're engaging with. I had said I wasn't planning to leave the Globe anytime soon. I ended up getting my current job largely because of LinkedIn. A woman who had helped me redo my resume for a side adjunct professor job I was doing — who I liked, and we talked from time to time, but not often — knew my boss who was hiring at Red Cell. He reached out to her and said, "I need an in-house lawyer who has also been in BigLaw, ideally, and run a business." She was like, "Oh, Heather's been talking about this on LinkedIn. Let me connect you." It turned out to be a really great fit that she certainly wouldn't have been likely to think of me for had I not stayed top of mind by talking about this so frequently.
Khurram Naik: How did you size up Red Cell? You loved the Globe, you recognized you weren't going to be GC anytime soon — but how did you evaluate this option to see whether it made sense?
Heather Stevenson: When she first reached out, I looked at the website for Red Cell and I was like, nope, nope, definitely not going to do this. At the time it looked very different than it does now. It was a bunch of men, former government officials, with whom I didn't necessarily share political leanings. Looked a little think-tankish. I decided to talk to the guy who'd be hiring me, and completely changed my mind once I heard about what they were actually doing. What Red Cell does is build and invest in national security and healthcare companies that are using AI and tech. What was so cool about it to me was that I did love Thirst, I did love building a business, it just hadn't quite worked out. But this was an opportunity to help build a bunch of businesses as a lawyer. That was one thing that was really big. The other was that as much as I loved the Globe, it could feel slow-moving at times. It's a 250-year-old paper that has some entrenched processes. And I did want to be a GC eventually. I hadn't really planned on it as early as it ended up happening, but it felt like an opportunity I'd been looking forward to coming early. So I decided to go for it. Telling Dan, my boss at the Globe, really was not fun. I felt terrible. But he of course was excited for me. In the end, once I understood the opportunity, it was an easy decision, largely because of the ability to participate in building businesses while also being a lawyer — to combine the two things I wanted to be doing.
Khurram Naik: What does being GC mean to you? What was significant or important about that?
Heather Stevenson: As not the GC, you're obviously doing legal work with hopefully the business in mind, but you're not always in the room for some of the big-picture business strategy decisions. As a GC you are, or at least hopefully you are. That's really fun, and it makes the role more rewarding. It also takes out some of the frustration when you get to be there and share your view up front. You can at least sometimes avoid the business doing something that creates legal work that didn't make sense, or legal challenges later. Or at least people know about it. When they're doing something that's going to create regulatory challenges or compliance issues, at least it's being planned for, because you are in the room, and it's also in your head, so you're emotionally prepared for it. I also like managing and mentoring people, and my team right now is very small, but I like that aspect of being a GC — getting to grow a team with me.
Khurram Naik: What was the biggest challenge for you when you moved into the GC role at Red Cell?
Heather Stevenson: I'm more than two years in and I still feel like I'm drinking from the firehose. I think that's the nature of the business we're in — we keep doing more and more. The challenge was, and continues to be, appropriate prioritization. There is a lot of work that needs to get done, but we all have to be careful, as a whole legal team and even the broader Red Cell team, about making sure that as we race ahead, we're racing in the right direction. There was also a steep learning curve at the beginning for just learning about corporate governance, Delaware C-corps, issuing equity, all these things I hadn't really done. I'd seen the back side of it when I was at Sullivan & Cromwell, dealing with shareholder derivatives and securities litigation. But there were new areas of substantive law I had to learn while also figuring out how to be a GC.
Khurram Naik: How do you allocate your attention between legal issues and business issues?
Heather Stevenson: I don't necessarily think of them as separate most of the time. There are times when I'm just sitting there literally reading Practical Law or reading a new opinion that may change how we interpret something, or learning about the Corporate Transparency Act. But for most of the time when I'm thinking, it's how do these pieces fit together. If we want to be able to use this IP in these three companies, but also be able to sell that company ahead of this company, how do we need to structure that? That is legal and business. You can't really separate one from the other.
Khurram Naik: The Globe is a very old institution and Red Cell is certainly newer. By nature of the business, it's probably a very different risk profile. How did you get comfortable advising on risk at Red Cell compared to the Globe?
Heather Stevenson: It is very different. At the Globe, we had set amounts of risk we were willing to take on certain things, and we also weren't doing that many things that were all that risky, at least that I was involved in. We are constantly talking about how to manage and balance risk at Red Cell and our portfolio companies. There are some places where we will draw a clear line — we will not violate the law, which sounds obvious. For example, we have a company that is now a platform for obtaining psychedelic-assisted therapy. Only psychedelic-assisted therapy that is legal in the United States, meaning federally and state. So right now, that's just ketamine. But figuring out — well, what if we started an ibogaine facility in Mexico? It's legal there. That type of thing is a real challenge. And we just have to weigh business upside versus legal risk. Ultimately some of those things we decided didn't make sense, because even though it's legal to do that in Mexico, building it into our overall business strategy and repatriating that money was going to be very challenging. It wasn't really who we wanted to be as a company. We want to be fully on the side of the law. But when there's gray areas, we have to have discussions about it. There are certain places where courts haven't opined, where the law isn't fully developed. Everything around AI is new. It's just important to align everyone, including our insurers in some cases, around what we're doing.
Khurram Naik: At this stage in your career, what is the thing you're most excited about on, say, a year time horizon?
Heather Stevenson: I'm a little over two years in, and Red Cell is totally different than it was one year ago, two years ago. I think we're going to be something really different and really cool in another year. I'm excited for how we're not just building companies that make a difference — which is so important — but from a legal perspective, we're starting to really think strategically about how the different companies can interact with and be set up in ways that benefit each other, so that even if they are independent companies, we're creating this more powerful whole than the sum of the parts. We haven't quite figured everything out yet, but we're going in that direction.
Khurram Naik: At this point do you feel like nothing about your career can surprise you? There's no path you couldn't see yourself taking given how disparate the different paths have been?
Heather Stevenson: The only thing that would surprise me would be going back to a law firm. Nothing else would surprise me. And I think that's cool. I could literally do anything. I kind of feel this flexibility to do whatever I want. Having left the law — having left a prestigious BigLaw job for Thirst, which is admittedly not prestigious, very risky, very stand on dirty floors, covered in fruit juice all day — if you can do that, what can't you do? It's a really cool place to be.
Khurram Naik: Can you talk about that? We've done the finances of making that decision, but I'd like to touch on the status issue, because it's so huge. Sullivan & Cromwell, litigation, New York, Manhattan, beautiful office, you have your own office, all these trappings of success. You went to Columbia. Most of your peers are in capital institutions. That's your entire reference group. How did you get over that status hit to launch this no-name juice bar?
Heather Stevenson: When I was first making the decision to do Thirst, I didn't really think about it. And I couldn't tell you why. The status thing just didn't occur to me. I started to feel it as former colleagues would come in to say hi and support us. They were completely there being kind, in no way judgmental. But they'd be there in their suits, and I'm there in my baseball cap and oversized T-shirt. Or we would do catering orders to some of the Boston firms, and I'm literally going in through the service entrance with my quart of juice. That was briefly hard, but I was doing what I wanted to be doing, and I knew that. I was kind of too busy for the first year to worry about that, or to think really about much of anything other than getting through the day. By the time things started to calm down, and I wasn't always the one running across Boston with a quart full of juice, I was over it. I'd done that. I had delivered to these people. I had worn my baseball cap around my colleagues in their fancy suits, and it was okay. I don't have a really good answer other than — you just do it. At some point you realize it doesn't matter.
The way Heather walked through service entrances of Boston firms in a baseball cap is the same kind of status reset Sunny Kim described after quitting BigLaw to own her own narrative. Both stories end the same way — once you've done the thing, the status reflex stops firing. Listen to my conversation with Sunny Kim.
Khurram Naik: I think what's interesting is that would be such a different story post-pandemic, where people's eyes changed and everybody has the story of who's walking around in a suit anyway. So everything about the story would be completely different. I really admire your courage during that pre-pandemic period. If you were going through this experience three years later, it would be very different.
Heather Stevenson: I think that's totally true. I think there are a lot of people who value things more in line with doing something like Thirst after we experienced the pandemic. And — I can't put a weight on how much this matters — but I never started with a chip on my shoulder or anything to prove when I went into law. From a very young age, everyone always told me, and society told me, and my parents told me, you'll be whoever you want to be, you'll do whatever you want to do. Nobody was surprised when I got into Columbia or went to Sullivan & Cromwell or any of those things, just because of the opportunities I'd had growing up. I think that made it easier for me in some ways to do something different, both because I hadn't worked as hard to get there as I'd always expected to get there, and because I always felt like I could go back.
Khurram Naik: That's huge. That's the part of the story I want to lead to. You mentioned your mom's a lawyer, your father's a lawyer as well. Could you talk more about those influences? Because that could have cut in both directions. It could have cut in the direction of, oh, all this pressure, look at my parents, they couldn't turn careers out of this. Why might you afford it? You could have felt this pressure. Tell me, what was it about parenthood, something that you observed along the way — what was it about that influence that had the outcome you just described?
Heather Stevenson: So many things. My parents are both lawyers, as you said. My mom was a litigator — or is a litigator. She's, I won't tell you how old, she'd be mad, but she's old enough to be my mom, and she's still practicing. She loved work and loved trial work. I watched that — we're very similar — and growing up I thought, I think I want to do that too, that seems really cool. And they never pressured me to be a lawyer. They always said, go do what you want to do. If you want to do this, that's great. If you want to do something else, that's great too. I did Teach for America after law school. At one point I thought I'd do something related to urban studies, which was my undergrad major. They were fine with whatever. Then I got to Sullivan & Cromwell and I was a litigator, but what I was doing was so completely different than what my mom was doing as a trial lawyer in Boston, where the relatively big cases actually go to trial. Whereas these multi-billion-dollar securities litigations don't typically go to trial. You would think with access to lawyers in my family and social networks I would have realized this difference before I got there, but I didn't. So that was a funny surprise. When I told my parents that I was going to leave Sullivan & Cromwell to start a juice bar, I think a lot of parents would not be pleased with that decision. My parents paid for all of my education — they paid for my undergrad and my law school. And they were just like, really, are you sure? And I said, yep, I'm really sure. And they're like, okay, how can we help? My dad, who was retired by this time, walked over and bought a smoothie almost every day. It was great because I got to see him, and he'd come in even when I wasn't there, and our manager would text me pictures of him being like, your dad was in. My mom would cater smoothies for her practice group lunches. I'm lucky that way — but they've just always been super supportive. I think that made a lot of these decisions easier. And, you know, I was talking before about the value of not having your whole identity wrapped up in your legal career. The fact that they never told me it should matter really helped, too. A lot of people grow up hearing, you're going to be a doctor when you grow up, or you're going to be a lawyer, or whatever the thing is. And they get there or they don't, but it's almost ingrained in them by that point that that's some key part of who they are. I never felt that way about my career. It's one thing that I'm doing. Whether it's lawyer or not, it is something, it is important, it is valuable, it is not the only thing.
Khurram Naik: You've talked about how it's good for lawyers to not have their entire identity wrapped up in their work. What happens when they do?
Heather Stevenson: I had a LinkedIn post about this the other day, and some of the reactions were really fascinating. I think when they do, they're in big trouble. A couple of people said — and they didn't say it of themselves, so I would love to talk to these people — but a couple of people said, "I have friends who live, breathe, love law, and it's all they have. And if they lose one job, they'll find another. If they lose one case, they're down, but they're back up. And it's what makes them happy." That is interesting. Maybe for those people it works. I think more typically it makes you unhappy and makes it harder to make good decisions. Because if you think that fundamentally who you are is just a lawyer, and then you take a hit, you lose a case, you lose a client, it's really hard to deal with. If you get to a point where maybe the position you're in no longer makes sense, it's harder to let go and say, maybe I should take a break from this role, take a break from lawyering. So I think it's a really risky position to be in. And I feel that way about being almost anything. It's not just lawyers — I'd be similarly concerned about somebody just being a doctor.
Khurram Naik: Do you have prescriptions for how to not have a lawyer-dominated sense of self-worth? How to have a diversion of identity? Is there a playbook for being aware of whether we're in that?
Heather Stevenson: I think there are at least two pieces. One is the mental — how you think about yourself. The other is what you actually do with yourself and your time. They're related but not identical. On how you spend your time, because I think that helps with the mental — go do other things. If you don't have any hobbies anymore, what did you like to do when you were 10? I'm not the first person to say that, but literally spend half an hour drawing or riding a bike or whatever — just doing something that brings you joy, or you find interesting, or you're bad at but could be fun. Just to be something other than just a lawyer. And then the mental piece — so much of it is just how you talk to yourself about yourself. If you tell yourself you're just a lawyer, that's how it's going to feel. Are you also a partner, a parent, a friend? Are you a member of certain communities, church groups, political groups, civic groups, a team? Identifying those things and just telling yourself, "Oh yes, I am a lawyer and a mom" — for me, I'm a lawyer and a mom and a wife and a friend and a runner and someone who likes to travel and someone who likes to cook, and all these things that go beyond just my professional identity. I think that makes it a lot easier when any one thing — whether it's career or some other thing — isn't going right.
Khurram Naik: When you think about your core competencies as a professional, what would you say are the one or two or three things?
Heather Stevenson: A combination of approaching everything with a sense of curiosity and willingness to work extremely hard. Putting those two together is a key strength. One without the other doesn't get you all that far. If you're curious but you don't do anything about it, you're not really any better off. And if you're just grinding, you'll probably be an okay junior to middle-level person, but you'll never really progress, because you always need someone to tell you exactly what to do. I think of myself as really good at reading and reacting to and dealing with people. That's important because so much of how we make huge strides as an organization is as a team. By being able to be a good team player and reactive to others, you can really add a lot of value. And then just willingness and ability to learn new things, I think, is key.
Khurram Naik: You should anecdote those first two. What are moments that illustrate those competencies?
Heather Stevenson: In terms of the combination of curiosity and willingness to work hard — an example without going into too much detail was a recent, not that recent, like a year and a half ago structuring question, where we had a plan for how we did things, how we set up companies, all the early-stage stuff. Someone mentioned to me the way that a different incubator was doing it. I said, oh, that's interesting, started learning about the different options, went down this rabbit hole. Found a few good options that seemed to me would be worth exploring more, and actually put in the time to understand what they were and lay it out in a way that was understandable for my colleagues, so they didn't have to redo all the work I had done. We ended up changing something about how we structure things in a way that should make our investors a lot of money. On the second one in terms of people — meetings can be going really well and then suddenly they just get off track, and you're not quite sure what happened, but everybody's angry and frustrated. A lot of times, it's just being the person to literally say, "Okay, I think we're all feeling frustrated. Here's what I'm hearing — who hears something different?" It's not really a special skill. It's more of a habit of being the person to be like, hey guys, let's pause, this is okay, work together, how can we move on? I think anyone can learn to do that. It can feel scary at first to be the one to take control of any room. I'll do that even if I'm not the most senior person in the room. Just getting meetings back on track regularly is a good example of how being able to work well together can help you turn what was going to be a lost hour back into a productive one.
Khurram Naik: Mapping out your strengths is awesome. I'm curious how you feel about — for people in their careers or transitions — do you feel people should focus on their strengths, or to what extent should people shore up weaknesses? How do you think about that?
Heather Stevenson: Ideally you should get into a role that allows you to use your strengths, not just because you're going to be better at it, but because things are more enjoyable when you're good at them. So you're going to enjoy your core role. But then I think, depending on the role, there's a lot of value in going from bad to okay at the things that are weaknesses. If you can get into a place — this is for in-house lawyers, really — where the role relies heavily on what you're best at, and then you've increased the things you're bad at to okay, you're much better positioned to be an overall advisor to the business, which is really what you want to be as an in-house lawyer. I think it's different for law firm lawyers. There's a certain value to being the absolute best at one random little piece of the tax code, where you know people are going to call you and maybe everybody's only calling you for one hour, but you're adding a ton of value just for that. There aren't many in-house lawyers who can be that specialized, which is why we need to work on our weaknesses.
Khurram Naik: What's the LinkedIn post you're most proud of?
Heather Stevenson: I don't think it's necessarily the best-written post, but I have one that I like the most, which is a post I first wrote several years ago. I don't normally repost my posts, but I repost this one that starts, "There's no such thing as too nice to be a lawyer." Every time I post it, it gets thousands of reactions. It's gotten millions of views over the years. I love, love, love that so many lawyers are excited and agree on this idea that there's no such thing as too nice to be a lawyer. I always want to be a kind, respectful person who's doing everything I can — even when I am fighting with somebody who's not being nice to me — to be a good person in my work and in my personal life. The post is about how you can be nice while also negotiating very hard for your client. You can agree to extensions and all sorts of things that make your counterparty or opposing counsel's life easier where it doesn't hurt your client, just because it's a good thing to do. It's easy to say no, but you don't need to. I love it because I like the idea of a warmer, kinder legal profession where we are respectful of each other, even when we are in tough negotiations. But I also like it because I think a lot of the reactions are about how anyone can be a lawyer. There's no set type of person who has to be a lawyer, which is really different than an idea a lot of people grew up with — of a particular man in a suit as what has to be a lawyer.
Khurram Naik: Is there a post that surprised you in terms of popularity?
Heather Stevenson: I posted one the other day that I was surprised people liked so much, but now I can't think of it. LinkedIn feels so random to me a lot of the time. It is so hard to tell what resonates. I run experiments. I don't repost the exact post, but if something seems weird and gets a lot of traction on a particular theme, sometimes a couple of months later I'll try again with that theme. And it works again. Oh, I remember the one — the recent one was about lawyers, or service providers, when we say, "Let me know if you have any questions," we have to mean it. It was just funny how many people reacted to it.
Khurram Naik: I'm really glad we took the time to sit down, because your worldview is so fascinating. You're such a warm and open person. I'm glad I found you on LinkedIn. You're one of my favorite people to follow on there. You have such a fresh perspective. You really are a vanguard for how people approach their careers — not just the decisions they make, but even how to present and share it with people. I really appreciate you in that way.
Heather Stevenson: Well, thank you. I love your posts. I love talking to you. Love this podcast. So thanks for having me on.