How I Built My Small Business

Karan Singh - Mastering Entrepreneurial Mindset: Insights from GINGER and HEADSPACE HEALTH Co-Founder

• Season 1 • Episode 37

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Today we have a special guest, Karan Singh, chatting with us about his journey in starting and growing a business in the mental health space.

Karan is the co-founder and former chief operating officer of Ginger, a leading mental health and coaching platform that merged with Headspace in 2021 to form Headspace Health in a multi-billion dollar transaction.

Although Headspace Health is far from a "small" business, Karan's journey started small, and the lessons, wisdom, and insights he shares are valuable for everyone.

Under Karan's leadership, Ginger was recognized by Fast Company as One of the World's Top 10 most innovative companies in healthcare and was named a World Economic Forum technology pioneer. 

Karan also volunteers on the Dean's Advisory Council at UC Berkeley's Haas School of Business and was the recipient of MIT's Social Impact Fellowship.

This episode is sponsored by Pareto Labs, an online business education platform.

Connect with Karan:

LinkedIn: https://www.linkedin.com/in/karanvsingh/

Headspace Health: https://www.headspace.com/

Subscribe on Apple Podcast , Spotify or other major streaming platforms.

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Website: https://www.annemcginty.com/

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Anne McGinty:

Before we dive into today's episode, I want to share a quick word about our sponsor, Pareto Labs. I didn't have the time or resources to go to business school, so I've been learning on my own terms through experiences, interviews and continuing education courses. Recently, I discovered Pareto Labs, an online education platform that brings business courses to life through entertaining videos. It makes learning complex topics feel like you're watching a TV show. I took their course on leadership with Nathan Rosenberg, and the lessons have been so impactful that I've found myself sharing the leadership principles and key characteristics of great leaders with my kids and friends, integrating what I've learned into my daily activities. The best part is you can sign up for a two-week free trial, so there's no risk. Head over to ParetoLabscom that's P-A-R-E-T-O-Labscom and sign up for the free trial. Trust me, you won't regret it.

Anne McGinty:

Welcome to how I Built my Small Business. I'm Anne McGinty, your host, and today we have a special guest, Karan Singh, chatting with us about his journey in starting and growing a business in the mental health space. Karan is the co-founder and former chief operating officer of Ginger, a leading mental health and coaching platform that merged with Headspace in 2021 to form Headspace Health in a multi-billion dollar transaction.

Anne McGinty:

Under Karan's leadership, ginger was recognized by Fast Company as one of the world's top 10 most innovative companies in healthcare and was named a World Economic Forum technology pioneer. Karan also volunteers on the Dean's Advisory Council at UC Berkeley's Haas School of Business and was the recipient of MIT's Social Impact Fellowship.

Anne McGinty:

You can find a link through to his business in the episode's description.

Anne McGinty:

Before we jump into the interview. If you get even one takeaway from today's episode, please share it with a friend and follow the show to help me reach more listeners. Thank you so much. Let's get started.

Anne McGinty:

Thank you to our listeners for being here today. Karan, thanks for coming on the

Anne McGinty:

show

Anne McGinty:

.

Karan Singh:

Anne, thanks so much for having me.

Anne McGinty:

So can you take us back to before you started a business? What inspired you to enter the mental health space in the first place?

Karan Singh:

It's been about 15 years now. Hard to believe, but the catalyst of that moment for me was I had a loved one who unfortunately tried to take their own life, and so I was on the other end of a phone call one Thanksgiving and I was just completely blindsided. I had no idea. Fortunately they survived. They're still here and in fact they're thriving now, but it was one of those moments that you will always remember and it shook me. In my car and as a person of color. My family's, originally from India, grew up in the United States, but mental health is a topic that we never went into and it was the no-go zone, it's true, for a lot of people of color, I think and so we didn't talk about it and I thought things were fine and I realized that you know, almost everyone's going through something, and not necessarily you know a diagnosed mental health condition, but many times stress and anxiety and potentially depression.

Karan Singh:

So that set me on the course and eventually I was in consulting and biotech world and in healthcare and but not in mental health specifically, and I realized I wanted to pursue this passion and try to solve this problem. So I went back to graduate school at MIT and Harvard, at the business school, medical school, and eventually started what became Ginger. We had a graduate school really trying to tackle this problem.

Anne McGinty:

Coming out of graduate school, what were the next most pivotal steps that you took that led you to successfully starting Ginger?

Karan Singh:

Looking backwards it feels like it's a straight line, but when you're in the moment it's very much twists and turns, and so I think it all makes sense in retrospect.

Karan Singh:

So I don't think I had a premeditated plan as much as it was just this like desire to try to find a way to solve this problem and, growing up in the Bay Area, like thinking about how technology and data had transformed so many different parts of the world, like it hadn't yet done that in mental health care, and so I think there was just a foundational belief that that could be true and should be true.

Karan Singh:

There was just a foundational belief that that could be true and should be true.

Karan Singh:

And yet when I look in medicine and in healthcare, mental health was sort of the stepchild. It was off to the side. It was underfunded and under-supported, under-researched, misunderstood, and so I spent a lot of my time really step one, trying to understand the problem more, and that's part of the reason I went back to graduate school in the first place was really just to create some space and not be working while trying to do that and actually be able to go deep and build new connections and new relationships and approach it with a beginner's mind, and the deeper I dug, the more I realized there's a billion people worldwide who are suffering from mental health disorder. 50% of people in the United States live in a county that doesn't have access to a single provider. The problem is just so pronounced, and that was 15 years ago During COVID. We all sort of saw it firsthand and felt the level of stress and anxiety, and unfortunately, right now it's even more pronounced with a lot of our kids, adolescents and teenagers especially.

Anne McGinty:

What do you think the root cause is in? The rise in mental health problems, you know.

Karan Singh:

I think it's twofold. The first is it's been there. We just can see it. Now we're talking about it, now we're being more open and vocal about it. We have athletes and movie stars and musicians and all these, you know, public figures who are really being more transparent about how mental health matters and how it can impact their ability to perform. And in many ways it's, you know, like I say, it's moved from the back room to the board room, like it's actually now a part of conversation and dialogue, and you know boards of directors and Fortune 500 companies and others, because they realize it's such a critical part of being able to be productive and be effective, and so I think that's part. One is just like the stigma is lifting, so people are talking about it. So that's well.

Karan Singh:

that's one aspect, but then the second is that there is absolutely like in certain pockets with certain people and like we were talking about with adolescents in particular, or you, certain communities of color, a higher prevalence and a higher incidence, and we're absolutely seeing that right now and some of it's the you know after effects of the pandemic and some of it's the after effects of under support in this for so many years, and so I think it's disheartening, but at the same time it's also maybe as the entrepreneur it disheartening, but at the same time it's also maybe as the entrepreneur it's really optimistic, because people are talking about it and people are funding it and people are jumping into it and supporting it and being more passionate and finding ways to solve it in different ways, and I think that's incredibly powerful.

Anne McGinty:

What is your perspective on how screens might be impacting the mental health of adolescents today?

Karan Singh:

Yeah, I was waiting for us to get there and you know it's an active conversation. I know we have certainly at School Beyond. I mean, I think there's some pretty incredible research that's been coming out about the impact of phones and screens and sort of digital interactions for younger kids in particular. Things like access then to social media as being really hard to process and manage when you're at that age and kind of the addictive nature of a lot of sort of the way that these tools, services have been set up can have a really profound impact on the mindset of a child or a teen, and so I think it has dramatic impact. I'd say the flip side is it also can be a really powerful way to provide support and care and access to services, and so I think there's, you know, two sides to that coin. I think there's ways to do it in a mindful and sustainable way, but we certainly have been on one side of that spectrum for the last five, 10 years especially.

Karan Singh:

And I think we're starting to realize the after effects of that, and that's why you're starting to see things like the Surgeon General come out and talk about and warn against the use of, for instance, some of these services at too young an age. So you have to do it in a mindful way and in a thoughtful way.

Anne McGinty:

Yeah, I know, I think being in the thick of it it's very difficult to really know what that even is. So, rewinding a little bit to just the story of like, when you started Ginger, what would you say were some of the biggest lessons that you learned from starting and growing that business?

Karan Singh:

I think, there's where to start.

Karan Singh:

We started Ginger at the time, in 2011, merged with the Headspace team, which we'll talk about, I'm sure, later in 2021. And so I've been on this adventure for almost 13 years now, and so I'd say the first order lesson is entrepreneurial mindset is just foundational to being successful. It was not something I ever was taught in school. We did an early stage startup accelerator program, got a lot of different training from different places and people, but building resilience and finding ways to kind of create a bounce back muscle was never in the cards and I realized, honestly, it's been maybe one of the most important things, because the reality is stuff's going to go wrong.

Karan Singh:

You're going to lose a critical customer, have, you know, negative press or feedback, lose a key employee, not be able to, you know, in our case, we raised venture financing, not necessary for every business, but not be able to raise capital or not be able to withstand an external shock to the you know, to the world like COVID, you know there's all these things that are outside of your control that ultimately, it's your ability to respond not just react to that stimuli that allows you to do this in a mindful way.

Karan Singh:

And at the end of the day, I think for so many small business owners and just entrepreneurs in general like they want freedom and they want the ability to create something that doesn't exist, but doing so stressful and can be really hard, and not only yourself, but your family, your partner, your spouse, your kids, whoever it might be and so taking care of your own mental health, particularly because founders have a higher rate of depression and anxiety. The clinical research that shows that that could be 2x prevalence or incidence rates. So you got to take care of yourself first.

Anne McGinty:

Yeah, and speaking of those bounce back muscles, because you're so right, but for someone who is listening, who maybe doesn't have a natural resilience and they don't bounce back quickly, do you have any strategies or tools as someone who's kind of been through it that you could give them as advice?

Karan Singh:

I have a lot. It's probably the topic I talk about the most, because most founders don't know who to turn to, don't know who to talk to, don't want to show vulnerability and don't want to show that they might be weak quote, unquote when the reality is like everyone's going through something and it's better to build practices to support that. So I'd say, when I first started, I didn't do any of these things. I was, you know, always on all the time. I didn't have great boundaries, I didn't know how to unplug my startup or company was my identity, like I was doing the opposite of what I will tell you now, which is to say, a mindfulness and meditation practice is an incredibly powerful antidote and is such a meaningful way to build resilience.

Karan Singh:

I mean, you know, and you and I started with the small, deep breath before we pressed record on this session and it was just a great reset and you know it's something that, for instance, we do at Headspace and I encourage a lot of folks to do is thread that throughout their day, find ways to thread that throughout the day, ideally building a meditation practice which can be so simple it can be a few minutes a day or it can be more robust.

Karan Singh:

But you know, ideally now I do it morning and evening, both to kind of set an intention for the day, like very simple and just a way to be able to also ground myself. I'm like what do I want to achieve? But then, just as importantly, at night as a way to process the day's events and just unplug, because I often found I wasn't sleeping well because I was just caught up in everything I needed to do. And the reality is, as an entrepreneur and a small business owner, most everything is falling on you. There's not a whole lot of other people necessarily, and certainly those early days that can be true.

Karan Singh:

So you feel like you have the weight of the world and you can use this as a really important strategy to unplug and reset and level set on managing your emotions and your mindset in an effective way.

Anne McGinty:

And you seem like a generally optimistic person. So are you just talented at seeing the positive in a situation and being able to redirect your attention beyond the meditation, beyond the breathing? How have you gotten through some of the muck?

Karan Singh:

Yeah, no, for sure. To be clear, I've learned this over the years. I don't think I was born with this, although I definitely have a generally optimistic mindset and, I'd say, a lot of entrepreneurs that I meet just like believe the world can be better. There are a number of other things I've developed, so one of which is this mindfulness practice, but you know other things like.

Karan Singh:

I have a forum, a group of other entrepreneurs that I get together with once a month. Got it tomorrow. It's going to be a couple hours long. We have an external facilitator. We've been doing it for almost 10, maybe 11 years now and it's been like one of those almost religious practices I never miss forum, if you will. And at first I didn't actually realize what it was going to be. I thought it was going to be a place where we traded best practices about building a company, from branding to accounting to sales, all those sorts of things and I realized, like, actually, so much of this was like outside of that that that comes up and it's a great forum and place to get feedback and ideas.

Karan Singh:

But it was also a place where you could talk in an unvarnished way about whatever's on your mind and sort of like what are you avoiding that's getting in the way of you being happy and successful? And I don't didn't always connect that to business success, but I very quickly realized like personal, family work, like all three categories have to be fully full or addressed or supported. So this is a great way for me to be able to take a beat pause. It's so easy to just keep going but like reflect and talk about hey what, what is in the way, and and make sure that that's not necessarily your spouse or your partner, that's not necessarily other employees.

Karan Singh:

It's like a safe space to be real and be authentic, and it's more for you than for anyone else, but you get a lot of great non-advice advice from that, so that's been another really powerful tool I've used to help.

Anne McGinty:

So is Forum a group of college friends, or what is this?

Karan Singh:

Yeah, it's interesting. It started through one of our seed investors who really, at the time, pulled together a bunch of other entrepreneurs about 10 of us and we had an external facilitator and there's some best practices and structures. It's modeled off of YPO, the Young Presidents Organization, and so there's some strategies and approaches to facilitate the discussion. But in effect, I mean, at its core it's getting together a group of people that create a safe space for which nothing is disclosed outside of that container and you can talk and you can do it in a structured way so that it's helpful and everybody gets some time to be able to work through it. But it's really powerful to do that with other entrepreneurs or other business owners who might be going through things that they don't realize are actually shared across other people, and just that shared context and experience is a really powerful mechanism to process some of those emotions.

Anne McGinty:

Absolutely what a resource to have, and only two hours a month, I mean. It's not a huge commitment but a great way to reground. So, ginger, after 10 years you merged with Headspace Health. What motivated you in the first place to pursue a merger with another company?

Karan Singh:

Yeah, you know it's been an adventure it's my first time founding a company and first time merging companies and a lot of great lessons learned. I think it starts with it always starts with the people and the culture, and I think in many ways there was such a great alignment in how we saw the world that we believed in a world at the time where everyone could be kind to their mind and that everyone could have access to lifelong mental health support and so we went through a series of twists and turns of ginger and a few different pivots over the years, and one of the early pivots we had was a business model pivot, where we previously were kind of selling into healthcare systems, hospitals and clinics this technology solution, but then eventually decided to become one like become a virtual clinic ourselves.

Karan Singh:

And when we did that, we talked about the three C's of support, coaching, clinical and content, and we thought we could only do two out of the three, and so at Ginger, we built a coaching and clinical service so you could download the app and, within 60 seconds, start talking to a mental health professional, a coach, who could help you with whatever might be going on, many of the things we're talking about right now.

Karan Singh:

It's actually been an incredible resource.

Karan Singh:

Or, you know, talk to a therapist or even a psychiatrist if you need medications, and so having this sort of access to a mental health support team in your pocket, around the clock, whenever and wherever you need it, it was so powerful.

Karan Singh:

And we realized that it was still missing a key ingredient, which was content, which was things like mindfulness and meditation practice or other accessible content that could help us in scaling access to care, and so the Headspace team had built an incredible brand with 100 most influential brands, partnerships with Netflix and Sesame Street, and had found ways to break down barriers to accessibility and to stigma and all the ways that we talked about. So that we realized was like the fundamental problem is people have got to get through the front door first before they even get into care, and so being able to partner with someone like Headspace and bring this vision of accessibility to the masses and then real care and real support was ultimately what drove the merger and what has driven sort of the product and vision since then. It's been fun, it's been adventure, it's been hard, all the things, but we're on a new size and scale and opportunity ahead.

Anne McGinty:

What is that like? Building and blending the culture of the two companies? It sounds like you are more or less aligned, but I imagine that there were still some differences that needed to be ironed out.

Karan Singh:

Yeah, yeah. No, it's interesting. It's never easy. Mergers are hard. I think that there's no doubt about it and I think a lot of it has to do with this. It's people.

Karan Singh:

Mergers are the merging of two different sets of people. Even if there is cultural alignment, you still have to figure out well how do you restructure the teams and set them up for success, and so that took some time. And mergers are different than acquisitions, where there's clearly kind of one company sort of identity, if you will. I think the merger in many ways is sort of bringing two companies together to create or found a new company. So it was in many ways, a refounding moment and an opportunity to redefine sort of how we existed and like what we wanted to do.

Karan Singh:

So I've learned a lot about you know how to do that well, and a lot of it has to do with being clear about your vision, do your values and being explicit about how you're going to reorganize your team so that they have clear roles and responsibilities and can be able to execute. I think that's probably one of the most important lessons I've learned over the last 10 years is getting your who right, getting the DNA right, or the mix of people you have is so important and it's going to change, like the team that you might have when you're you know a couple people founding a company, and it's going to be different than the team that you might need when you're at 50 or 100, which is different than what you need at 500, which is different than what you need now and we're you know, over 1000 people, and at every stage it can and should change and that only constant is change, and that's a good thing. It's hard but it's a good thing.

Anne McGinty:

So you've had to maintain this strong level of culture while it has expanded quite rapidly. What do you do now to make sure that your company's culture is supportive and that is cohesive too?

Karan Singh:

Yeah, no, it's a great question, something actually I'm really passionate about in addition to chief operating officer, which is the role I played for a long time, I serve as chief people officer here at Headspace, so I think a lot about culture and values and you know a lot of it has to do with making them explicit.

Karan Singh:

So we have a set of four core values that we talk about things like seek truth, speak truth as like a fundamental value, and really what it is is sort of a, an operating system that can help them make decisions.

Karan Singh:

So meaning like if you're in a meeting and you're not sure should I say the thing, If you remember seek truth, speak truth like you're going to share it, but you're going to do it in a compassionate way, and so I think it's something that we spend a lot of time on, both defining, but then maybe more especially as we're growing, more importantly like pruning and figuring out when you see behaviors that are inconsistent, like naming those, calling them out, helping people understand hey, that's actually not what we believe that value means. Here's what it looks like. And being really explicit with stories, and those stories whether you're a couple people or whether you're, you know, a thousand people are the culture and are the values that you aspire to be and I think are one of the most important things you can get right, because that who, ultimately, is going to define your success, Like that is the most important thing, sort of you have enough financial capital to execute on the plan.

Anne McGinty:

As an entrepreneur and the founder of a mental health business, I know you mentioned some meditation in the morning and in the evening. How do you stay personally grounded throughout the day?

Karan Singh:

Every 18 to 24 months I re-recruit myself to PetSpace or to this mission. So I sit down with my wife, lena, and with a few other like personal mentors and I say, like, do I still want to be doing this? And I kind of asked like, well, yeah, what would that look like? And it's more like there's clearly like a set of things that I need to do at work. But it's actually to your question, like, what does my day look like Like, what does my week look like? What does my month look like?

Karan Singh:

And so I you know, for instance, right now this has been true for the better part of eight and a half years, since my daughter, ella, was born. Family is incredibly important to me. It's a non-negotiable and it's one of the reasons why I actually wanted to be an entrepreneur because I had the ability to be able to craft my schedule in ways that allow me to spend time and prioritize her and family. And so on Friday afternoons, head out to school to volunteer in cooking class, or I'm going to be trying out a assistant soccer coach this fall and I'll find out when. But I think Tuesday afternoons, and it's things like that that are like just I know, are really critical for my own happiness at home that I want to prioritize. But I want to make explicit, and so it doesn't mean I'm any less productive. In fact, in many ways I'm more productive because I have these boundaries that, like previously in the old world, like pre Ella, I just didn't set.

Karan Singh:

And I read this book that I recommend to everyone. Set, and I read this book that I recommend to everyone. It's called Essentialism, and the byline of the book is the disciplined pursuit of less but better, and the whole premise of the book is like it's less, not more, especially for most entrepreneurs Like you think you got to do more to be effective, and in so many ways it's actually doing less, because this is a marathon, it's not a sprint, and I certainly didn't expect to be doing this. You know, 12 years later, and it's like survive till you thrive, and so I think figuring out some of these practices that give you the space so you don't let work bleed into all parts of your life and you can be intentional, actually helps you be more effective at work and in your business.

Anne McGinty:

I totally agree with that. How do you shift from one to the other? Can you let go of your work while you're doing your personal life activities?

Karan Singh:

Yeah, great question. I'll say you know, I'm very much still a work in progress and I think I'll always be so I haven't nailed it yet.

Karan Singh:

And in some ways it's almost not compartmentalizing, it's sort of integrating. There's this work-life balance question versus like work-life integration. I've been learning a lot about dialectical behavioral therapy, this concept that two things can be true at the same time. It doesn't have to be, or it can be and I think that that's true here like you don't have to choose just work or just life, you can choose both, but you have to dial up the knob higher sometimes and higher the other way. So the ability to flex is really important.

Karan Singh:

I know I keep coming back to mindfulness, but having a mindfulness practice or meditation actually has been a really powerful way to like reset so I can shut the laptop, take a beat, just do something as simple as like going outside, spending a lot of time in nature. That's probably my number one practice and way to kind of unwind and use that as a reset moment to then be able to go and spend and be fully present for my daughter or family or otherwise, and I think that's been really helpful. It's so simple and I feel like it was advice I heard all the time but, heard it didn't do it, and I think that's been really helpful.

Karan Singh:

It's so simple and I feel like it was advice I heard all the time but heard it didn't do it, and until I started to actually do it I realized it's actually quite easy to do and can have profound impact, and so I'd start there.

Anne McGinty:

There are so many ways that I feel like it's easier to say it than do it. If someone were to approach you who was interested in either starting a business in the mental health space or getting involved in some way, do you see any gaps anywhere in the market that you think it's underserved, or there is just a critical sort of point that needs to be addressed?

Karan Singh:

It's a great question. Yeah, there's so much. Unfortunately, there's too much to go around right now. There's so much need. I will say I think to what you and I were talking about earlier. Teen or even preteen mental health is just a category. It's just so underserved and undersupported and is hard, it's tricky, it's tricky to get it right, but there's clearly more that needs to be done there, and whether it's in schools or whether it's at home or whether that's through other forums.

Karan Singh:

I think that's just an area that I'm really excited about seeing more innovation and support, and so I think that's in general category. I'd say one thing we haven't talked much about is just overall. One of the reasons that mental health is so hard is not just the stigma, but it's really the idea that first you have to admit to yourself that there is a problem. Then you have to find a provider who's available, and most providers in the United States aren't available. You wait weeks, if not months, then you find that provider Many of them aren't practicing evidence-based medicine and then when you leave that provider and they bill you, they're out of network and not accepting health insurance, and so they cost hundreds of dollars a session.

Karan Singh:

Most people in the United States and around the world, that's just out of reach, and so, like each part of that puzzle, there's opportunities to solve, and so, in general, I'd say, like a strategy is thinking about ways to apply. I mean, there is the AI hype cycle right now, but thinking about ways to apply artificial intelligence, general AI, as a force multiplier for some of these problems, like just not having enough supply. Can we use that to help amplify, kind of the impact of coaches and clinicians. I think it's just an area that we're working on and focused on, and something that's going to continue to transform the space.

Karan Singh:

There's no doubt in my mind it's going to be a fundamental transformation but, it's going to take time and you have to do it in the right ways, and it's not an overnight success. There'll be some hard work to get that right, but I think that's ripe for opportunity.

Anne McGinty:

Thinking about AI a little bit more. What are your thoughts on how AI will impact what you're doing?

Karan Singh:

Yeah, I mean it's wild.

Karan Singh:

The future is here.

Karan Singh:

I have been very skeptical, or just maybe treading more lightly and being thoughtful, but as I use it in my own life whether that's writing emails, whether that's summarizing content, whether it's like blog posts, performance marketing there's so many ways you can at least use it as a force multiplier, and so I don't see this in many ways as like a replacement of although there's certainly parts of the economy where that's true but I actually see this as like a force multiplier for the work that you're doing, and I think that's very true for mental health care, where it'll be a way for coaches and clinicians especially, to be able to do more sustainably, to really flip the less but better script.

Karan Singh:

It's kind of like more but better, or more but sustainably, and I think it's really powerful and I think so many clinicians and coaches especially, are burnt out, like just like small business owners. The rates of burnout are really high because the profession is so hard, so taxing, there's so much that they've shouldered, and that I think we have an opportunity to really use this as a way to give them more relief and to help more people along the way. So I think it's happening. We're using it in very targeted ways right now to help support, and we're seeing some really interesting results.

Anne McGinty:

And in both your personal and professional life. Can you give us some insight into what AI software you are currently experimenting with?

Karan Singh:

What I've been most fascinated by is the different prompts and use cases, like even just in my email. I use Superhumanhuman and it has some level of auto responses built in Kind of like in Gmail.

Karan Singh:

If you use Gmail, the smart compose, where it gives you just like a quick reply, and it's getting to be pretty good because it's able to process what I've said before and then, in my own tone, kind of say it for me, and so I've started to use that in a very lightweight way. Just a couple of settings. One very important and critical piece of advice is be thoughtful about what you put into it and be really careful about that. Increasingly, I've been using it to summarize content, so like if I get a really long post email note or a piece of content I need to write, like using that as a way to either summarize and or jumpstart. Like I have to give a speech or give a talk or give something where you know I just would love some pre-work done that I could then modify and edit, but sometimes it's helpful to have a primer as a starting point.

Anne McGinty:

It's been amazing how many conversations I've been having recently just about AI and how exciting it is. I mean, some people are very worried about it or they're just very resistant to it. But I spoke with Amy Wilkinson. She's the entrepreneurship lecturer at Stanford's Graduate School of Business and she was just saying that between a two hour meeting and a drive home, in that drive home she can talk to conversational AI about how to craft a proposal based on what she's saying as she's driving and when she gets home in her email there's a multi-page proposal that is more or less done. She said it's about it's like needs to be edited, but it's about 85% done by the time she gets home and it took 20 minutes for something that would have taken her two days to put together.

Karan Singh:

That's a great use case.

Anne McGinty:

I love that. I'm going to start using that.

Karan Singh:

I've been using the conversational agent and chat GPT. It's actually really, really powerful. So, to your point, I think so many people can feel resistant to it because they're scared about change, and I think the reality is like this is one of the best pieces of advice I got early was just the only constant is change, and so, like, if you are an entrepreneur, a small business owner, like you should expect that change and be planning for it and think about how you can integrate it, not ignore it.

Anne McGinty:

If somebody were to approach you today and they, let's say, they just want to get out of their career or maybe they're a recent graduate and they are inspired by entrepreneurs, they are thinking about being one, they are wondering whether or not they have what it takes what advice would you give them?

Karan Singh:

Try before you buy. You can start to test things out in lightweight, low touch ways. You don't have to necessarily jump full force in lightweight, low touch ways. You don't have to necessarily jump full force in, for instance, if you're in school, like a graduate program or undergrad, like even increasingly, there's ways to give it a try. There were some few things that I tried before doing this that gave me a sense that actually this is something I was interested in. I didn't intend to start a company. I didn't actually think that. I didn't realize that that's actually what I needed in order to solve the problem, but what I was focused on was a problem, and so if there's one, you know, big piece of advice, it'd be to find that white space.

Karan Singh:

I hear people talking about founder market fit, which is a concept I really like. It's like product market fit is you, can you build a product that fits a market? The founder market fit is can you find a problem that you're energized by? And, like for me, I didn't realize it at the time, but mental health has become this problem that I feel like could be.

Karan Singh:

You know my forever work and there's so much depth and issues and now that I've gone deeper. There's more opportunities to go even deeper. That I've really enjoyed understanding it at a really, really nuanced level, and that may not happen for everyone, but I'd say being focused on founder market fit and identifying a problem that gets you energized, that you just can't put down, that you keep coming back to, would be maybe priority number one to figure out whether this is something or a path that's right for you and then talk to other entrepreneurs and I love the podcast and all the folks that you've been talking to who are able to talk about what it's really like. You know, because it can be glorious from the outside. It can be really hard on the inside, and both are true and that's okay, but you got to be comfortable with that.

Anne McGinty:

And I love what you were saying. You know you mentioned it earlier in the episode but again, just aligning your values with your business, with your life, so that it's not really work-life balance, it's more just that you're fully integrated. I think that that is the goal. I think getting there can be a bit of a journey, weaving around In your journey. I'm sure that this has happened many a times failures. So when you look back at the last 15 years, what stands out to you as some way that you failed?

Karan Singh:

I have to decide which one to pick or which ones. Goodness, I've got my fair share of battle scars. I don't think we spent as much time on them as I normally do. This is a tough game to play, and I wrote about this and I'm happy to share it.

Karan Singh:

You can maybe link out to it if it's helpful about our kind of three pivots over the years, our business model pivot, which I was alluding to, where we made the wrong call when it came to commercializing the product that originally thought that we were trying to sell to providers and eventually became a clinic ourselves, because we realized that the fundamental problem in the space was access to care. It wasn't efficiency, it was access. But then the second big change was our team pivot, as I called it, which was ultimately we didn't have the right team to scale that business and so we had eventually to change out many of the team. We got in a new CEO, my co-founder left, many other executives left. We had to go through layoffs and other things that were incredibly hard for so many people and even changing out different people within the board.

Karan Singh:

And then I've talked about kind of my me pivot as an entrepreneur, a founder, and thinking about how can I change my mindset, kind of like this notion of before my daughter and after my daughter in many ways, like how did I sort of adapt? And I continue to have pivots now, post-merger, and we've got a whole host of new things that are coming, and I used to think that pivots were like a euphemism for failure, you know, and I realized like it's the opposite of the truth. It's like good thing you pivoted, because otherwise you wouldn't be around and I think it's survive until you thrive. And I think it's thinking about like each one of those opportunities as a way to learn and to take a beginner's mind. And so I'd say I made a lot of mistakes and fortunately, I feel like I learned from most of them, if not all of them, and it was the learning that then produced the next opportunity.

Karan Singh:

And I read a great book by Daniel Pink about the power of regret. It's called, and I think it's actually another one that I'd add to the list, because as an entrepreneur, I have had so many regrets of the thing I thought I wish if only I had done, and I realized, like that's just part of the process, you know, and if I hadn't done it I wouldn't be where I am today, and so that's been, I think, a super important lesson. I've continued to learn because I have made many, many mistakes, and I think what I've tried to do is focus that on. Okay, well, what now? Like, what can I take from that? And it's so hard at the moment, definitely, and you got to process and work through it, but it's really then, okay, it goes back to the bounce back muscle. It's like, well, hey, can you get back up? And if you can do that you'll be successful, you'll be just fine, but you got to get back up.

Anne McGinty:

So now what we need is a way to teach people how to do that.

Karan Singh:

That's right, that's right.

Anne McGinty:

Somebody out there listening. We need a bounce back business, something that teaches people how. I have two more questions for you, and one of them is just. You know, as we were talking about a fully integrated life, what would you say? Your overall goal is then, with everything that you're doing balanced with being a family person, what's the goal?

Karan Singh:

It's a great question. I think I'm going through a redefinition of that right now, so I don't know if I have a very clean answer just yet, but I think it comes down to purpose and feeling like your life and my life has meaning and I think I get that meaning in each of these different buckets from work which we've talked a lot about, and so much of that has to do with having a legacy, if you will, that the work that I've done can impact and change the world in a meaningful way and that can help change.

Karan Singh:

The trajectory of mental health now at Headspace has been proactive and preventative care and finding ways to move upstream and to solve this problem, not by tackling everybody who's already sick, but finding them well before that right, and creating things like the bounce back muscle as an example, right, or supporting kids early, or finding, you know, entrepreneurs earlier in their journey who could start to learn these skills, because it's a learnable skill and many people have diagnosed depression or anxiety or otherwise, but there's support and there's treatment for that. That can work really well. So I'd say there's that's like one bucket. It's like continuing down that path of like what would the next version and level of that? And whether that's within a company or whether that's government or whether that's through, you know, non-profit or a variety of different sectors or ways to get to that problem at a holistic level. Like I want to see that fundamental seismic shift and then, at the same time, like I want to enjoy the ride and I want to live a full life and have community and connection and relationship.

Karan Singh:

And that comes from, you know, prioritizing time with my family and especially my daughter for the next 10 years before she goes off to college, and I know that's like a priority for me. It's something, you know, my wife and I talk a lot about. It's just like that is where we're going to spend our time. It's important to us. And then, on the personal front, I'd say it's investing in many things we talked about, like a mindfulness meditation practice for mind, body, soul, if you will, and continue to be active. And a big strategy I've used for my own mental health has just been exercise in all forms and in all ways In order to achieve the first two buckets. I've got to take care of myself and make sure that I'm healthy and take care of yourself and so you can be there for as long as possible, and to care for yourself so you can be there for as long as possible.

Anne McGinty:

Yeah, you've got to enjoy the process. It can't all be about the angle, because that angle will just keep on shifting.

Karan Singh:

Especially in entrepreneurship. You've got to enjoy the ride.

Anne McGinty:

So for a final question if you could go back Karan and have a conversation with yourself in your early 20s, what would you say?

Karan Singh:

Do you Meaning like if you can set your own bar of success, if you don't let others define it but you get to define it, you take care of yourself along the way, I think you'll be much happier. I wish I had learned that much earlier in life, that as soon as I started defining my own happiness, my own success, not through the bar of anybody else, that I can control it, and I feel really centered and really balanced right now. But I certainly did it when I was coming out of kind of school and you know, was trying to find what and where and why I wanted to do what I wanted to do. You know it's a discovery process and sort of be patient through that. But you set your own bar and you do you.

Anne McGinty:

I love that. That's some great advice

Anne McGinty:

. Well, .

Anne McGinty:

As thank entrepreneur, looking much for coming on the show and taking the time to chat today.

Karan Singh:

Thanks so much for having me and I love the questions and I appreciate the opportunity.

Anne McGinty:

As always, thanks for being here. Today's key takeaways as an entrepreneur, looking back can feel like a linear path, but in reality, the journey is usually filled with many twists and turns

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. If you have found a societal problem that needs a solution, dig deeper and try to further

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understand that problem so that you can get more clarity around a potential solution. An entrepreneurial mindset is foundational to success. While business school will teach startup acceleration, it won't teach resilience. Resilience and

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building a bounce back muscle is something you can only get through experience. Stuff will go wrong in your entrepreneurial journey. Learn to respond, not just react

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to these situations. Being a business owner can be stressful, impacting

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not just yourself but your family and relationships. Take care of yourself and learn to

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respond mindfully. Mindfulness and meditation are excellent tools . . building resilience capital, your deep breaths is your company's success. throughout

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the

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day

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.

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In the morning, set your intention with a few deep breaths and at night, fully unplug for a restful sleep. Learn how to manage your emotions and mindset in an effective way

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. Join a group of like-minded individuals that you can connect with on a regular basis. Getting the right people on your team is crucial Beyond

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financial capital. Your team's success determines your company's success.

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Every 12 to 18 months or so. Think about what does your day look like, your week, your month, and evaluate. Consider reading Essentialism and

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the Power of Regret. Survive till you thrive. Teen and preteen mental health is currently underserved. Teen and preteen mental health is currently underserved. Opportunities exist in recognizing

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the problem, finding available providers using evidence-based medicine and ensuring cost-effectiveness. Start using AI as a force multiplier .

Anne McGinty:

Tools like Superhuman, chatgpt and other AI technologies can enhance productivity. Embrace change instead of ignoring it. Find the white space and founder market fit, meaning, find a problem that you are energized by. Mistakes will be made. Learn from them to create new opportunities. Remember the bounce back muscle. If you can do that, you'll do just fine. Don't let other people define success for you. Come up with your own definition of what success means to you. Say your own bar and you do you. That's it for today. I release episodes once a week, so come back and check it out. Have a great day.

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Anne McGinty

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