Surviving the Startup Roller Coaster

They say that the startup game is a roller coaster, and for many, it is one of the most difficult, frightening, stressful roller coasters in the world — I call it bootcamp for the soul.

As a founder, an executive, or a leader in a fast-growing company, we can feel very alone in our struggles, and we often hide them in an effort to appear like everything is going great. If you’re feeling alone in your role in the world as a leader, you can find healing in connecting with the stories of others.

I interviewed the remarkable Terry Lee. He’s a founder, he’s a former CEO, he’s a former COO, and he is human, just like you. Many of the lessons Terry learned along the way would not have come without a certain degree of heartbreak, pain, and struggle. And the growth he experienced on the other side shows us that the only way out is through, and the journey is ALWAYS here to teach us what our soul most wants to learn.

If you are a leader who’s never been through the entrepreneurial grind before, if you’re an aspiring COO or entrepreneur founder, or if you are actually in the midst of the most challenging parts of the startup rollercoaster, you’ll receive a lot of valuable information and insight from this conversation with this deeply compassionate man who shared his journey as a leader.

Enjoy the conversation~ Live Conversation

Caneel Joyce: What’s really tricky about being a founder, an executive, a leader in a fast-growing company is we can feel very alone in our struggles, and we often will hide them intentionally in an effort to appear like everything is going great.

High achievers, often we’re conscious of how we are coming off, we’re conscious of the impact we have on others, and so, in essence, we can begin to isolate ourselves.

It’s such a gift when someone is willing to open up their own story and share what it was really like for them.

If you’re feeling alone in your role in the world as a leader, you can find healing in connecting with the stories of others.

We have a remarkable guest named Terry Lee. He’s a founder, he’s a former founder, he’s a former CEO, he’s a former COO, he’s a rockstar soccer player, and he is a normal guy, just like you.

Terry Lee is co-founder of Mezcal Rosaluna, a mezcal brand that is launching in summer 2020. Previously Terry was COO of MeUndies, an underwear and loungewear brand based in Los Angeles, where he helped the company grow to $50 million in just three years.

He also helped to secure Stephen Curry as the brand face of a consumer marketplace called CoachUp, and prior to this he worked at Johnson & Johnson in marketing and sales, and played NCAA D-I men soccer and graduated from the University of Notre Dame.

I remember the first time that we met was back when you were at MeUndies, COOing, and I came in, I met you, I met the others on your team, and we stayed in touch for a while. I didn’t end up coaching you when you were there, but remember how many times roughly we got together before you decided to become my client?

Terry Lee: Yeah, it was a couple of … It was more than a couple times, and I thank you again for your patience and for sticking with me. It’s a testament to your persistence and patience. I’m so glad that we were able to kind of continue that relationship after we initially met, so thank you.

Caneel Joyce: You are welcome. Thank you for your persistence, because it is so unlike me to see a prospective client more than once, that’s very rare. Usually just one meeting, either you’re in or you’re out, I’m moving on. But with you, you kept finding great ways to invite me back and meet you for coffee, and whatever. I remember even telling you at the time, “I literally don’t know why I keep showing up. I don’t know.” But I trusted it was for the right reason, and then years later you finally became my client. I was so excited to work with you.

Terry Lee: I think it was the perfect timing, even though it probably took a lot longer than both you and I expected, and I’m just really grateful for all the things that I’ve learned in the time that we spent together. Even moving forward, after those sessions I think a lot of the lessons and things that we talked about keep popping up and I’m learning them on deeper levels, which is cool.

Caneel Joyce: So wonderful. Terry, for a while you were on a streak of sending me every single morning, early in the morning, some inspirational message. So I would get up and I would be met with this great affirmation to start my day or a great reminder, a great message. I wanted to read to you just one of my favorites.

Terry Lee: Yeah, that’s a couple years ago.

Caneel Joyce: You sent this to me in 2018. You said, “I was reading about harvest and I learned two things. One, it’s the most labor intensive activity of the growing season, and two, the completion of the harvest marks the end of the growing season, and it feels like that’s the stage I’m in.”

Terry Lee: I remember sending that text.

Caneel Joyce: I love that. Can’t wait for your harvest festival. Thank you. Well, I’d love for you to share today about the journey that you’ve been on. I’ve certainly been inspired watching you grow over these past few years, and the depth with which you’ve really taken on your personal growth work, and your extreme commitment to being open, learning, and growing. I think you’re an excellent role model for what is possible. I’d love to just hear about your journey.

Terry Lee: I will give a high-level overview and then whatever area that we find is interesting we can kind of dive into further.

I had grown up playing soccer my whole life, and the reason why I think this is relevant is that soccer was an all-consuming hobby for me. I don’t even think it was a hobby, it was my life.

I played it as much as I could, I would practice all year round, play on multiple teams, and there was this one singular goal that I had, which was to play in college at the Division I level. Fortunately, I was able to walk on to the team at the University of Notre Dame and that was an incredible experience.

But so often in life, at least from what I found, is that you achieve a goal and then there’s always more that you want.

So as soon as I joined the team it was this mentality of okay, I need to start, I need to score goals, I need to make a positive impact for my teammates and for what we’re building together in this program.

Unfortunately, I didn’t reach those goals that I had envisioned and was humbling because I had such a clear vision of what that would look like.

I would visualize me scoring goals, or me having this active significant role on the team, and it just never came to fruition.

So that was really humbling in a sense.

I bring this up because it’s almost reflective of how I feel the last few years have gone.

Fast forward after I graduate from school I spend a few years working at Johnson & Johnson, and then I had the opportunity to move out to LA and join this company called MeUndies, which is an underwear e-commerce brand, and I was fortunate enough to join in a COO role.

We grew to $50 million in three years, it was a lot of fun, a lot of growth in a short amount of time.

If I’m being honest with you, after those three years, I just had a real … I wouldn’t even call it confidence. I think there was a lot of arrogance that was kind of beneath it, just in terms of my own ability and how much I had made an impact.

It was a lot of focus on me and my capabilities. Coming out of that I was like, “Look, I’m ready to start my own journey and start my own company.” And so I started a beauty company called Panacea.

I started it with a couple of other partners, and unfortunately, kind of similar to the soccer story, it didn’t pan out the way that I had envisioned, and I think it was this reminder of results aren’t everything, and it brought to my attention to areas that I needed to grow in to move forward in my life.

That’s been the journey over the last few years.

Caneel Joyce: I was laughing a little bit at the beginning of you telling this story as you described being on the soccer team. By the way, this seems to be really a common thread amongst the executives I’ve met, is some really big commitment to a sport early in their life.

So Notre Dame is obviously a fantastic school, and a fantastic sports school. I have to imagine it was a really big deal, but then you get there and then the goal post keeps moving, and the bar gets higher. I’m laughing because what is your Enneagram type?

Terry Lee: Type three.

Caneel Joyce: There are themes here that were present in a lot of the work that we did together in your coaching work about on the darkest days maybe it’s never enough. I’m never doing enough, there’s always more I have to do. In your words, you called it striving.

Terry Lee: Striving definitely comes to mind, and it’s this mentality of if I do good, I get good, and results will come my way. It’s great and it feels great, it feels great for both my ego and for myself when that formula works, but when I feel like I’m doing good and not getting the results that I “deserve” or have earned, that’s where you start to get really shaken up.

Caneel Joyce: What’s it like then?

Terry Lee: It challenges this very deeply ingrained formula or way of living that I’ve adhered to. When it doesn’t go according to plan, you ask yourself, well maybe it’s me, maybe I’m not doing it the right way, and there’s a lot of insecurity that arises.

Look, I’m not going to begin to say it’s right or wrong, but I think one thing that I’ve learned is that I’ve tried to shift my focus and mentality from striving. The way I define striving is trying to do things that are outside of my control, or control things that are outside of my control.

I’ve tried to shift more to a mentality of striding, and striding for me is just going at the pace that I’ve been graced for. It’s letting things come to me. It’s about pull momentum, where I’m getting pulled into what I’ve been called to do. What my life is supposed to embody and look like versus me trying to knock down every door, do it all on my own effort in my own timing.

Caneel Joyce: What’s the difference in how that feels to do striding versus striving?

Terry Lee: I’m still learning it, to be honest. I definitely haven’t mastered it by any means, but I do think that there is a distinct difference on many levels.

Striving, it’s hard to recognize until you’re out of the striving mentality, but it’s a lot of hard work. The analogy I have is imagine pushing a boulder uphill and every little bit or inch that you move that boulder up, it’s dependent on your effort.

The line that I keep thinking of if life isn’t dependent on me. Life isn’t dependent on my ability.

I think that encapsulates what striding means, which is yes there is work, there is commitment, there are these things that I have to show up and do, but it just comes more naturally.

I’m along for the ride versus the ride being dependent on me.

Caneel Joyce: That’s a really big change. How do you really take stock and be willing to experiment with this totally different way of being, and letting go of the idea that we can control things outside of our control — this can be really scary when that’s been our MO. I don’t know if it was scary for you, but I’d love to just hear about the turning point and how you even came to these realizations.

Terry Lee: I don’t think it was this one aha moment, and then flip of a switch, it’s done.

There’s definitely been a few poignant moments but it’s been a process and it’s been a journey because I've been operating in this striving mindset for most of my life.

To think that I can undo or unlearn that at a moment’s notice is unrealistic.

That’s given me grace and freedom and patience with myself that I don’t need to have it all figured out today, and it’s about making small improvements.

It’s not even about improvements, I think it’s about recognizing the difference, and not beating myself up for one way or the other. Just be like "Hey, I feel like I’m striving in this moment. What would striding look like?"

Back to your original question in terms of what’s that moment consisted of, there’s one in particular that stands out, and it actually happened almost two years ago.

I mentioned before that I started Panacea with two other partners. One of them was my brother and the other was a good friend of mine. Unfortunately, it wasn’t the right team to build this company together.

It was no one’s fault in particular. It was the timing and how it all came together. I made this decision. In my mind, I thought I was falling on the proverbial sword and going down with the ship because the business wasn’t doing well.

I knew in my heart of hearts that it was a matter of time before we had to shut down the company. So in my mind, I was like, “Hey, I’m going to let you guys go so you can pursue other things while I try to figure this out, and it doesn’t get figured out then I’ll be the one to kind of take the blame.”

I made the decision to let them go and it really blew up in my face for many reasons. It led to a fallout in terms of friendship, in terms of my brother.

He and I were best friends up until that point, and obviously it caused a lot of conflict within our family.

I had made this decision and saw the repercussions of that decision, and it was one of those rock bottom moments where the things that I held dear to my life in terms of friendships, my brother, family, I saw them kind of exploding in front of me and I was like, “Oh man, this is a big wake up call.”

I realized I had to let go of the way in which I was living my life and the way that I was interacting with people, and building relationships but I had to let go and start over in a way.

I don’t know, it’s hard to describe, but that was the feeling that I had.

Caneel Joyce: You had to let go of your own brother and a friend. Now it sounds like it’s almost like if I were to rebuild myself what would that look like? So that level of discomfort opened up the possibility for a change.

Terry Lee: Yes, one of those things where I had to be shaken up, almost to the core, to recognize and be aware of these things that I needed to address personally.

At the time, thought it was like "oh well, it’s my brother or it’s this business partner, or my friend, they’re not the right partners for me, and trying to rationalize it."

What I was covering up were the insecurities and things that I needed to work on with myself.

As soon as I started to recognize that, honor that, and admit to that, I identified these are the areas I need to work on and to take a different approach moving forward.

Caneel Joyce: It sounds like a crisis moment when we find, I have so little to lose because there’s hardly anything left, that I’m able to let things go that I never thought I’d be able to let go before, or do things that seemed terrifying before and now I’m willing to do them.

Even something as simple as I will begin to say no to people who expect something of me. That was a big thing that I had to learn, that was hard, but it became very easy once confronted with the discomfort of not doing it was greater than the discomfort of continuing to do it.

Terry Lee: Yes, wow, that resonates for sure.

Caneel Joyce: I heard you say a word, and I’d love to trace back and hear what this word means to you. I heard you say grace and give yourself grace, which sounds like it is what you’ve done in my understanding of that word, but I’d love to hear how you understand that word and what relevance you think it has for leaders today.

Terry Lee: It’s a word that I heard it in the church growing up, and my family is Christian in terms of our background, and it was kind of one of those words like you’re in church or the song Amazing Grace comes to mind. You just kind of hear it but it wasn’t a word that I fully understood.

I think there are many levels, but I don’t think I started to really understand what grace looked like, at least for myself, until the past couple years. I think the best way I would define grace is being kind to yourself.

I think there is this mentality, at least from my own personal experience, and I imagine it is somewhat systemic with other leaders, or type A people, people who are really achievers, or people who are really kind of ambitious with different aspects of their life where you are your own worst critic, you always want more.

We talked about this mentality where you achieve something and then instead of celebrating it you’re automatically setting your eyes on the next thing.

The sports analogy that I would use is that you see an athlete or you see a team, or you even see a coach who wins a Super Bowl, or who wins the national championship, which in sports is the pinnacle, there’s no higher moment than that, but then they’re interviewed in the post-game interview and the coach or the star athlete goes, “Hey, this is great, but I can’t wait till next year to win another championship.”

And there’s nothing wrong with that mentality, but I think that is just how many of us are wired to operate and to approach our life.

When I think about this concept of grace it’s not necessarily setting lower less ambitious goals. It’s not putting in any less work, but it’s just giving yourself kindness and just being understanding of yourself in the same way that I would be for other people.

I saw that there was this misalignment or inconsistency. I would be very understanding and very kind to other people but when it came to myself I would beat myself up, even on little things.

Like hey, you’re supposed to get up at 5:00 in the morning. Today you 'slept in' and it ends up being 6:00 AM and I’m beating up myself for that, right?

It shows up in little ways but naturally, the little things are the big things in our life.

So that’s been an evolution for me and one that I’ll continue on, which is giving myself grace, giving myself kindness, and the patience and the rope to make mistakes, and be human.

Caneel Joyce: I’m hearing you say that in the past you might have made yourself a villain. So the people who have been watching this or listening to this show for a while are familiar with the drama triangle, they’re familiar with hero, and victim, and villain.

I’m hearing you say so okay, I like to wake up at 5:00, that’s when I’m guessing you go to the gym, I know you’re a big worker outer, but I get up at 6:00 and then I beat myself up for it, and I’m a bad guy.

I should, I should, I should. Ouch, ouch, ouch. I’m curious, where would you go on the drama triangle after that? Would you stay in villain for a long time? Would you hero yourself, would you go into victim, or would you shift between the three?

Terry Lee: I think all three of those roles really resonate, but the one that resonates the most is probably the hero.

Caneel Joyce: How do you like to hero?

Terry Lee: It shows up a lot of ways, and probably ways that I’m not even aware of yet, but one was I made this decision to hero and let go of my co-founders, and try to build Panacea by myself, that was as much of a hero example as anyone could have.

It was this mentality of hey, I’ll fall on the sword, I’ll take this on myself, you guys go pursue other things, and it was this mentality of oh, I’ll try to take on more than I’m capable of, and that’s very much the hero mentality if I understand it correctly.

Caneel Joyce: I’ll fix it, I’ll save it, I’ll solve it, and maybe even a little bit I hear fall on my sword, I hear maybe there’s even a little bit of martyr, as a combination of victim and hero. I’ll make this sacrifice because I’m the one who can do it, I’m the one who can save.

Thank you so much for sharing the arc of your growth journey in recent years, and knowing you as I know now I just want to share that I’ve seen you shift at a cellular level.

Your nervous system is different, and your level of calm, even your speed, the way you hold eye contact. Just the relaxation in your muscles is different, and there feels like there’s just so much more space when we talk compared to before, and you were already a very engaging spacious person, but there was more of the sense of urgency, and your level of presence is just it’s off the charts.

I’m sure people see that and feel that in you, and it’s partly why you’re a great leader.

I’d love to hear about the roles you’ve held: the role of COO and you’ve also now been founder CEO.

Let’s first dive into the COO role. This is a role for many CEOs and founders finding the right COO is the silver bullet that’s going to save them from all people and culture, and process problems, all the stuff that is really weighing them down and they don’t want to do it.

So they’re often looking for that panacea, that perfect COO.

You’re one of these that’s been in high demand because you’re successful.

Can you share with some of our aspiring COOs or junior COOs what are some of the things you learned along the way and what advice would you give?

Terry Lee: First off thank you for those words, super kind and it means a lot, especially coming from you.

When I think about the COO role it’s very much about finding a complementary partner to the CEO.

So much of it is fit. It’s also about having alignment, shared vision, and values. I’ll be honest, I got so lucky in terms of the two other partners that I worked with at MeUndies.

It was definitely not my own doing, it was very much Bryan, who was the CEO of MeUndies at the time, and Jonathan, who is the founder and now the current CEO.

We had a really good working dynamic that organically worked without us having to try. Looking back that’s something that I didn’t fully recognize just how organic and seamless it was because I tried to recreate it, and almost force it, if you will, later on at panacea.

The advice I would have is understanding the role at its simplest level because when we think about C-suite titles and even job descriptions and roles and responsibilities we can think of pages of what that looks like, but I think at its simplest level it’s about being a complementary partner to the person who is running the business.

If we’re talking about it in terms of title, it’s the CEO.

To build on that, the way I’ve always approached the COO role is to understand the vision from the CEO or the founder and translate that into tangible next steps that we can take every day.

Small little steps that we can take toward achieving that vision. It’s an execution role, and a learning process.

It’s a role that requires a lot of humility because you’re going to be operating behind the scenes, and may not be as front-facing, it’s not about you.

It wasn’t about me at MeUndies, and my posture when I was in a great headspace was how do I help John help Bryan articulate the vision more clearly so that I would understand and translate that for the rest of the team.

That was when I was at my best.

The one other thing that I would add with the COO role is I like to think about it as building scaffolding versus building a building, especially at an early stage company where growth and change is happening so quickly.

The reason why I like this analogy of building scaffolding is that it’s very flexible and malleable, and you can adapt and change on the fly, whereas if you build the building it becomes really rigid in terms of the structure.

Everything from how we communicate, so I think about communication architecture, I think about the way in which we make decisions, the way in which we hire and build the team, and retain, and train people, all these things I wanted to do with a level of conviction and a consistency in terms of building purposeful culture and a team, but also not so rigid where we can’t change things as we continue to grow.

Caneel Joyce: There’s a key tension right between the rigidity and the structure that you really are wanting and then the flexibility and nimbleness that you need in order to change, especially when the company is growing so quickly, and you’re a new company to begin with, and still reading the tea leaves in lots of ways. What’s been one of the biggest differences that you’ve noticed between being COO and being a founder CEO?

Terry Lee: There was a big difference, and for me it was more about the stage of company versus the roles, although I imagine the roles are still somewhat distinct and different.

For me I had joined MeUndies when we were about five or six people, so still very much at an early stage, but I would argue we had already achieved “product-market fit” in terms of identifying our customer base and having a solid kind of revenue base to build off of.

When I started Panacea it was from ground zero. So building something from ground zero to product-market fit is a totally different game than having achieved product-market fit and trying to scale that.

There are other entrepreneurs or even investors who’ve talked about this chasm, or excuse me, the difference between building something from zero to one and something from one to N.

I’m oversimplifying but I think MeUndies was in more like building something from one to N, and that skillset is just different than what is needed to build something from zero to one.

You can learn both of them, but it takes a lot of intention, self-awareness, humility, and it takes a lot of painful growth as well.

Those are some things that come top of mind, but also it helped me understand too where I’m better suited in terms of those types of roles, and going back to what we talked about earlier, this concept of striding versus striving, I want to because I’m more in this mentality of striding, if I feel like I’m striving too much, it’s an opportunity to learn and see if "hey, am I playing or working in a space that feels very natural or an extension of myself?"

And if it’s constant uphill, constant I have to grip my teeth and go through it, that’s probably a sign that I’m not operating within the role or the position I was meant to play.

In conclusion, I’ll describe it in a sports analogy where it’s like if you have a basketball team and you have a center who is asked and is pulling himself to be like hey, I need to play on the perimeter and shoot three-point shots and take the ball off the dribble, whereas they’re more meant to be a traditional center operating or playing down in the low post.

It just you could understand the tension that creates between their skillset, their mentality, and the role that they’re trying to play in.

Caneel Joyce: I think of this as living in your zone of genius, where you effortlessly easily are creating value using the gifts that you were naturally given versus living in your zone of excellence, which actually sounds like what you describe as striving, where you’ve worked hard to learn how to be excellent at something but the effort feels harder, it feels more draining at the end of the day.

If that’s all you did it wouldn’t be sustainable and you’d burn out. You can be great in both things but it’s the ease and flow that’s accessible to you when you’re doing the thing that you’re called to do, is it frees up so much energy, right?

When you’re figuring out where should this one employee go … I had a client the other day ask me, “What do you think about the philosophy that Facebook has that we should only focus on strengths and not on weaknesses?”

And I’m like yeah, I agree with that in theory, but then I thought about this excellence thing, and that so often we are hiding. We’re not even revealing at work what our genius is. Has that ever been true for you?

Terry Lee: I heard this great quote from another entrepreneur name Naval Ravikant and he talks about how my zone of genius will feel like play to me but look like work to others.

Caneel Joyce: Yes. Totally, and the zone of excellence feels like work that is really rewarding and that you’re really good at, but it’s so different.

So many times I go home from work and I’m aware that there was an output of energy but also so much energy came in, and I feel … I would pay to do my job. I would literally pay.

If I didn’t have access to do this job professionally, which before I didn’t, and I actually would pay to do this. I would take time off work and I would meet people at coffee shops, I totally get it. Is that where you’re at now? I hope so.

Terry Lee: Yeah, totally. I mean, I’ve been there but I don’t think I understood it or appreciated it as much as I do now.

Caneel Joyce: We sometimes judge and we think well if this doesn’t feel enough like work I’m probably not doing it right, I’m not doing enough, I’m not working hard enough.

Terry Lee: Yes, that resonates. It’s this shift toward what am I doing wrong versus appreciating it and being really grateful for the situation that we’re in.

Caneel Joyce: Completely, completely.

Terry, now having been through the number of roles you’ve played and companies you’ve been a part of and you’ve started, what advice would you give someone who is starting out, as they’re trying to figure out who should my partners be? Who do I want to be on that core founding team with me?

Terry Lee: For me it’s simple. It’s about finding partners who have a shared vision and shared values, and also understanding that shared vision and values in one area of life may not translate to another.

For example, you may have a best friend or a close family member where you’re super aligned in terms of the things that you value within a friendship, within a relationship, how you communicate, etc, but those may not directly translate over to the business world and building a company.

I look at it less like oh, that person is a bad co-founder or this person is a great co-founder, and I think it’s all about fit.

Another variable to the equation is timing.

The stage of life that we’re in translates to a certain risk profile. For example, if I have kids and I have a wife, a family to raise, that naturally changes my risk profile from when I’m single.

Understanding the stage of life that we’re in, and as a result from a macro perspective, the timing of things is important to consider.

There’s other things as well around work ethic and just complementary skillsets, and there’s a litany of things, probably a checkbox that should just kind of be observed and you should be aware of, but I think at the end of the day it really comes down to shared vision and shared values.

Caneel Joyce: I couldn’t agree more. What are some of the things that you’ve seen others hire for, maybe or hiring other leaders or other executives, and prioritizing them over shared vision, shared values that you think should not be prioritized?

Terry Lee: One is hiring or partnering with a co-founder who just on paper may look like a great fit, maybe in terms of the past success that they’ve had, the track record that they’ve built, but maybe not understanding how it may directly translate to the new business.

I think another thing is sometimes we’ll get a little too focused on finding the right partner, which again, is a very important decision, but lose perspective on what we’re going to build together.

One thing I’ve learned more recently, and it’s going to be a staple, it’s just going to be the lens in which I evaluate future opportunities is building unfair advantages.

You may have the best co-founder in terms of fit, shared vision, and shared values, but I think we have to be realistic that building a company, it’s a very low likelihood of success.

If you can build as many unfair advantages in your favor as possible, it naturally makes that journey a little bit easier. I think that sometimes gets lost in the mix of okay, I’m looking for all these different things in a partner, but just as importantly, how can we as a team embody some type of unfair advantages that give us a greater chance to succeed than any other team that may be entering this market?

Caneel Joyce: I’d love to talk about the challenge that you just mentioned. So it’s a very low likelihood of success when you start a company, right?

And for many, this brings on understandably a lot of stress. Your company is in an existential crisis almost all of the time, and you truly are really fortunate. Every month that you make it, every month you continue to survive, you’re winning.

But along the way, and for those who haven’t been a founder yet, this is good to note. Is that you will be confronted with some of the demons that you thought you would never have to face.

You thought you were successful in burying them, ignoring them, maybe you’d worked through them, and I just find it to be one of the most personally confronting journeys that you can ever go on. Has this been your experience?

Terry Lee: Yes. 100%

Caneel Joyce: It’s the ultimate bootcamp for the soul.

Don’t go into it thinking this is going to be really glamorous and it’s going to be really easy, and I’m going to start a winner and I’m going to win the game because there is only one way to win the game and it’s to make it till tomorrow.

But in the meantime, there are those dark nights of the soul. What advice would you have for a founder who is starting out, or maybe they’re in the trough of despair, and they’re stressed, they’re panicking, they’re maybe experiencing burnout, depression, anxiety. What are your tips for staying sane in the startup game?

Terry Lee: It’s a great relevant question, and one thing that I’m also trying to navigate, so I don’t want to pretend that I have the answers, but a few things that have helped me is trying to learn from those feelings and those emotions.

In my case, there is this tendency to suppress negative emotions. By negative I mean sadness, anger, and cling to positive emotions, happiness, joy, and this is something that you and I worked on a lot.

It is not judging the emotion by what it is, but trying to invite it and sit with it, and learn from it. My immediate reaction to your question about what do you do in your difficult times where you feel, and it sounds like you feel these intense emotions that are difficult to process and navigate through.

I think the first thing that I would remind myself and others is just to sit with them and experience the whole journey for all that it is, because the way that I’ve heard is the startup journey is like a roller coaster, right?

So like life, but the lows are very, very low, and the highs are very, very high.

There is this need in terms of maintaining your sanity of trying to be even keel and trying to establish a baseline in which you operate and live your life so that you don’t go through these, you don’t get swung either way too emotionally, but there is this balance where you do need to feel them to a certain degree.

I think through that feeling you actually learn a lot. Those learnings help you navigate that course of even fundamental decisions around your business of should we pivot, should we stay the course, should we hire this person, should we let that person go?

And it’s amazing what I’ve uncovered and learned by just kind of sitting with my emotions.

The second thing I would offer up is understanding that it’s an infinite game. This is something that I’ve learned more recently from talking with friends who are also entrepreneurs, but also Simon Sinek just came out with a book called The Infinite Game.

The basic premise, as I understand it, is so much of our approach in our life is dictated by wins and losses, successes, and failures.

Even what I mentioned before was thinking about it through a finite lens of hey, with a startup the chance to success is really, really low.

But my mentality has shifted from this finite, from playing this finite game to trying to play this infinite game. With the infinite game, there’s no winning or losing. The only way that you lose is if you give up. The only goal of the game is just to stay in the game. So if by operating in that-

Caneel Joyce: I have a question. I have a question. So I had to pause you because what do you mean in this case of the infinite game, what do you mean by giving up? Do you mean never shutter the business, never pivot, what do you mean?

Terry Lee: I think there are moments where you’ll have to let go, maybe shut down a company. Giving up I don’t think so much in the literal sense, but I think more figuratively of just giving up on life.

Sorry, I don’t mean it to sound like this end to life, but more so understanding that this, the outcome, the result isn’t a reflection of how I’m doing in this game.

It’s a data point and it will help me learn and course-correct on how I move forward. What I’ve tried to take from this approach or this mentality of the infinite game is that yes, I had to close down my first startup, and by all measures, it was a failure, but not beating myself up and pitying myself because it was a failure, but more owning up to it, taking full responsibility, learning from it, and then just moving forward with a higher degree of confidence and conviction because of the learnings and lessons that I gain from that journey, and understand that it’ll make me a better leader, better person, better entrepreneur moving forward.

Caneel Joyce: So the business may have “failed” but you are not a failure.

Terry Lee: Yes.

Caneel Joyce: Your business closed but you are not closing up shop.

Terry Lee: Exactly. I’ve learned so much from you, and I was telling you this the other day, but the lessons and insights that you’ve shared with me over the past couple of years keep popping up and I’m learning them I feel like on deeper levels.

So it’s not this one and done thing, but just continual evolution and one where I’ll just continue to let it marinate and learn from. So I’m incredibly grateful for you and all that you’re doing. So thank you so much.

Caneel Joyce: Thank you. My pleasure, seriously.

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