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Flexible thinking tactics with Poppy Jamie

Episode 13: This weeks’ Happy Millionaire guest Poppy Jamie has had an incredible journey from early TV presenter career to founder of the groundbreaking meditation app Happy Not Perfect, as well as co-founding the successful fashion accessories brand Pop & Suki. In this engaging conversation with Jay and Rupy, Poppy shares her tactics to combine happiness with entrepreneurship. 

What to look forward to:

01:05 – Poppy’s TV presenting career

01:40 – Poppy’s funny moment with Jude Law 

04:39 – App development

12:25 – Dealing with an unpleasant investor

17:02 – Adult mental health

19:46 – Flexible thinking approach

24:18 – Serving mentality

33:19 – Poppy’s exciting new venture!


HM Ep13

Apologies for the typos, this is an AI transcription


Welcome to Happy Millionaire, a show about how to make a profit with a positive impact and stay happy along the.


So excited. Yeah. Why don't you give us a sort of like a TLD R of like the arc of your career and how that all started?


It, everybody would say I was Bridget Jones. And it was sadly quite true despite how hard I tried, despite how much preparation I would give, it would all always, And I'm not sure if I can swear slightly, Fuck up. No. And so there was this one interview and I got, it was my first big one, and I'd only been asked to interview.

People that nobody really wanted to interview, which was, you know, somebody who left Big Brother five years ago. Yeah. Yeah. And anyway, finally, this was a goodie, Jude Law. JDE Law. Massive. Yeah. Yeah, massive. Did he still have hair at this point? I don't remember. I just remember him being very good-looking.

So I know it was funny cuz somebody brought this interview up to me three days ago and I went to go to YouTube to watch the video and I couldn't believe it was a decade ago. Wow. So 10 years ago there I am walking into this interview, Jude Law, and I'm so very excited. I'm, oh my God, it's just so good to meet you.

He thinks I'm a competition winner. I'm that excited. And so I have been kinda, No, no, I'm here for, for my tv. Yes. You know, on set pharmacy, I'm like reputable and anyway, shaking his hand furiously and I go to sit back down on my chair and I completely miss the seat. No. Oh my God. And I go flying and I'm lying on the floor and I'm wearing this tiny mini skirt.

You know, trying to kind of, you know, look professional, obviously clearly unprofessional, and half a butt cheek is out. I mean, just the whole thing is just absolutely mortifying. Then, the cameraman as shaking with laughter, and the PR can't get her breath. And I have to try and continue to do this interview while in my, in my head I'm like, You've just got fired.

You've just got fired. Yeah. You've just got fired. You've just got fired. And I thought, Well, there's only two things I can do right now. I can cry or I can just laugh. Yeah. Because. This is a disaster, and I get hysteric giggles and when I get them, there's no end to it. So I start getting the hysterical giggles and I'm trying to get this interview out and it doesn't, anyway, it becomes viral.

Interview. Suddenly every single, single person I, I possibly know has seen poppies fail in front of Jude Law. And, you know, people came up to me on the street, it was like, Oh my God, you're the girl that fell off the chair in front of Jude Law. And I'm like, Oh God, is this what I'm gonna be known for forever?

So embarrassing. So I decided to move to America. Because that clearly sounds like the logical next step. and, um, while I was in… Long story short launched the first TV show on Snapchat, which was pretty much the only TV show you could watch on Snapchat on a Saturday. And so we had millions of people watching it because they were really at the time, Evan and the team, they were very small at Snapchat.

stressed and anxious back in:

Where do you go? There was nowhere to go. There was no help. There was no conversation about it. Nobody was talking about it at the dinner table. Certainly, nobody was talking about it in the press about the kind of mental health epidemic that we were in. And it goes back to my mom. I thought, Well, my mom's a psychotherapist.

Could I put my mom in an app? I remember being told the most successful apps were the ones that behaved like parents. Uber could take you to school. Postmates or delivery can bring you food. And so if you look at all these, you know ones that we kind of go to most and I thought, But who looks after your emotional health?

. What year was this? This is:[:[:grew happy, not perfect from:

Had to persuade every, I mean, it was exhausting. It was three years of saying, This is important. This is important. Yeah. No one believed in it. Nobody believed in it. Yeah. And if anything, people didn't wanna talk about it. I got it, I had investors say, Can we just change the words on your deck? You take out mental health.

tech team, and we launched in:ping mall. I mean, my life in:

Yeah. It's been a full on decade. Wow. And now we've


I actually posted this, um, when I was announcing the acquisition, I posted my first deck. Oh. So, and it was so basic,, I really noticed within a year and a half how much that deck evolved. So for anyone writing their first decks, be kind to yourself and know that it is a constant iterable journey, if that's a word.

other at the time, and it was:

That you are willing to wake up your brother who likes to go to bed at night and you're willing to wake him up at 10 just to tell him. But I became obsessed and that's what I do with all my businesses. It is becoming a complete obsession that gives me so much joy to think about and I'm willing to sacrifice for it.

And I did. I sacrifice my television career for this company because of every investor. Um, okay, but you are not gonna carry on with the TV stuff, are you? In a way that was a bit shortsighted actually because as we all know, a bigger platform helps you get a better C but I was, if they wanted me to do that, I was willing.

And I remember going in and saying, I've got this idea. And he said, Oh, I think I met someone who can design some app screens. And that was the end of the conversation. Woke up to an email in my inbox and my brother's very efficient. He'd introduced me to a random guy that he'd met completely randomly.

That he had learned who. Wireframes, just app designs. And I don't think I realized how valuable designers are, especially when you're building tech companies. And apps in particular. In apps in particular pre-code. It's not expensive. Well, it's not as expensive as making mistakes with code. Yeah. I think that there's no time like the present, You know, I call this guy up saying, Let's meet this evening.

And again, I think you need that kind of momentum when you're setting up a company. Every hour should be so valuable to you that you don't wanna miss it. And so I met the. Didn't even care about his qualifications because I just said, Can he design some app screens? He said, Yes. I said, Great. We're off again.

I think you can waste time finding the right person for you. But I just knew I needed to get to my next step, and my next step was to show a. Uncreative investors, what this could look like in a physical form, rather than just in my head explaining why it's important. So we sat, I remember we sat down for a day and I said, Okay.

And I'd done the research and I kind of knew what I wanted and I had drawn it out literally on the kind of a back of it and napkin. That's sort of a vibe. And he created some really basic wireframes for me to then be able to show investors, if you click here, this is what the journey would be like.

ink this entire phase cost me:

Yeah. Is that all you spent to get Oh, I spent, to get to Wow. The point where I could get investment. I do think you can get very far on a small amount. Yeah. In the early days, especially when you're working with other young people that are passionate like you are, and then it was just, A game of networking and just being obsessed on email and emailing every single person I possibly could, and also speaking to really unusual people you don't think could help you.

Yeah, and how it really ended up being was I was doing a TV show at the time and I started talking to my producer of the TV show and he said, Well, I'll loan you. The first 50,000. Yeah. To be able to get you on your way. Brilliant. And then after that, my best friend in LA had a music manager who had just met a tech investor, and it was just through the most unlikely connections because I don't believe that there's value in an idea.

I tell. Everybody my ideas. Yeah. All the time. Because I think a, they're the good feedback. Or they can introduce you to your next jigsaw puzzle piece. Yeah. And I see building companies like Jigsaws, everybody's looking for a piece that they need to complete their jigsaw. So every, you need to tell everybody about your jigsaw in case they've got the secret piece that you're missing.

And then they introduced me to my main investors, and then from. I'd raised the first half a million, and after that, I was able to raise, you know, a few million after that quite quickly based on the legitimacy my first investors had given me. And then suddenly the space started bubbling. So it was kind of slow, slow, slow.

So slow, and then it went


Less favorable terms than if you are raising maybe two years ago. So for first time founders especially, I don't think you are in the sea of telling people exactly what you want to be investing on, but I invested on really terrible terms. And so these were when some of my mistakes started to show and I started to pay for them years later.

ad. I was a female founder in:

Both. Both. Okay. It was a UK company, but it was US investors. Yeah. And then we ended up having a top company in the UK and then a subsidiary in the. But I remember one investor, even when I had 50%, I remember one investor saying, You know, probably we feel really uncomfortable with you having so much of the company.

Wow. What? And he said, uh, he used the example. He said, Well, the founder of, um, it was a YouTuber at the time. And she set up a company, uh, sending out samples. Okay. And he said, Well, she only owns 5% of her company, so we feel all very uncomfortable with you earning 50%. So I suggest that you write to the board and tell everyone that you want to give me another 3%.

And I remember being so shocked and not really knowing what to say. Yeah. Because he was a really big voice on the board. Mm. And I think at the time I probably said, Oh, okay. Well, probably was just polite back and afterwards I thought, It felt, actually that was a bit unfair. I thought I've already given you 50% for not that much money and you've already taken away so much control of my company, but Okay.

And basically at the next board meeting, uh, hadn't given them the extra equity yet, and he screamed at me and he's like, What have you done since the last meeting? Yeah. I was just waiting for the tech to be built. There was nothing. I, you know, of course, I was working every single day on it. Yeah. But it, you can't, If the tech team said, This is the sprint, it's very difficult to speed them up.

I mean, I was hysterically crying for three days afterward. Geez. And the only reason he, he was so rude to me and screaming at me so much in these meetings was that I hadn't given him the equity. And I remember calling my parents saying, I'm just gonna have to give him the equity because I can't live life like with him being like this to me.

In a way, my life is gonna be easier if I just give it to him and my parents like, That's ridiculous, Poppy. You shouldn't have to do this. You shouldn't have to do this. And I said, But at this point, I'm already in too far. I've already taken other investors who I really like, I really respect. I'd be now screwing over them if I left.

I'm gonna have to endure this. So this is my life. I just wanna make it easier for myself. So I'm just gonna give them the equity and.


Varied, scary and dangerous for everyone's mental health, and I get it. It's like basically a big pyramid scheme. What happens in investing is that these investors have got LPs underneath them. They've got a lot of pressure, so they're feeling pressure from them to deliver. So then sometimes I feel bad for these investors who are screaming and.

Got their own mental health and then they're taking out on entrepreneurs sometimes. And there is this vicious selection of investors that, um, you know, can cr like create these situations which are just totally unfair and unneeded and, um, for you to have gone through that, it's just, it's sad. And I guess one of the hopeful items in this is that, You did have this mental health experience and I know you even got your method on the flexible thinking.

So was that stuff helping you? Cuz now all of the great things that you've learned on like through your journey, did you find those helping you in these tough times? Cuz it's really hard sometimes in life. Like I know what to do, but this is one of the hardest moments. This is the big test. And how did you cope in that and did those methods help you in Yeah,


I have been through as being as difficult as building a company. I almost find that so ridiculous to say because on the surface of how hard can it be, and I think the entrepreneur journey or any, and, and I generally think mental health in the workplace, whether you're not, it's not your own company or just in a workplace.

It's a hugely under-discussed topic because I think we've become much better at talking about how our childhood has affected our mental health. But actually adult mental health is hugely impacted by the environments they're in on a day-to-day basis, and often we're trapped in them. And again, that's a horrible word to use, trapped, and it's a horrible word to think that we are trapped in our jobs.

But being brutally honest, we are. You know, we've got mortgages to pay or rents to pay. So, you know, it takes a lot of maneuvering to course correct even to change jobs or especially when you set up a company, you are in that company until one of two things. You get bought, or God forbid you to go bankrupt or you go public, so they're your three realities or you step aside or you step aside.

But especially if you have investors that you really respect, which I did with happiness not perfect. I had people I truly loved and maybe I took it my fiduciary duty too seriously. But I was like, I'm gonna get these people's, I wanna be successful for them. Yeah. I wanna be the right horse that they've backed.

There's a. Pressure you put on yourself, the environment you put in, and so the flexible thinking method that I write about in my book was life. Same thing when I talk about mental health and things that have helped me. It has been the difference between me being in this seat and maybe not even being here.

It was that bad at one point, you know, it was. The things that I prioritized, and I wrote about this in my book, but dancing in many ways saved my life. When I found this dance studio in New York where I was building the company, I remember going in and just. Bursting into tears to this entire class because I think we, we forget how much we're hunched over a desk and we're, even if we're cycling right, we're hunched over still.

Mm. And it was the first class that kind of like opened my body up and, you know, opened my chest and asked me to like, raise my hands above my head actions that we do as children, and they suddenly get less and less and less as we go through our life. So dancing was connecting to my body. Probably the biggest change in all of this, so probably


I wonder if you can distill exactly what that means.


And so flexible thinking is a group of science back tools from users, behavior science to C B T to act acceptance, commitment therapy, to be able to remold and rewire our brains. So we have the power and the capacity. Constantly relook, and modify our response to the world. I often think that you know, we don't have sometimes a choice to be happy, but we have a choice to be kind to ourselves, and so it teaches you how to do that.

in a really easy four-step method. That's


So, yeah, communicating it in a way that is compassionate I think is something that you do really well. Thank


And at the basis of flexible thinking is that, It doesn't cost anything, you know, to connect with our body, which is the first step, doesn't cost anything to do five-star jumps and go for a walk in the morning, and to connect truly to how we feel. That is a skill and a step away from what we're used to doing, which is suppressing or distracting and pretending it's not really going on or ignoring the pain that we're feeling.

Getting curious costs. Nothing just to ask, is this true? Is my inner critic true in what it's telling me? Or how can I look at this differently? Step three being compassion, again, costs nothing to be kind to ourself, and yet when we're kind to ourself, as Dr. Rui will know, Very well. Our whole body changes the way that, you know, our immune system is reacting to life and we're kind to ourself.

We massively deregulate the nervous system so we can move into that rest, relaxed system. And if we know stress equals not the best decisions, and we include a little space, which is pauses to connect, to get kind, and to focus on what actually matters in life, and then respond to life, we create. The reality for ourselves.

Um, that was the main point of flexible thinking is to step away from reacting to life. And so when we are in tough times when the economy and we're reading the news and it just seems like the end of the world, we can stay in that state of alert. Everything's going wrong, but it's not gonna help us. We all have to learn to take a beat, to pause, and to make different decisions because this is why I find the whole manifesting world a little bit controversial what makes your future is the decisions you make in the present.

Why are we not teaching ourselves to make better decisions in the present? Because I can guarantee that will create a different future and a future you more want to live in.

I think it's important to have friends that don't value you for what you do. That's a good one. Yeah. Yeah. It's meeting up for dinner and realizing that you probably didn't speak about work once, but you were engaging in it. Other things, whether it's this cinema or whether it's just having a joke, whether it's just letting your hair down in some way, shape, or form, and them still loving you just as much afterward.



I find myself talking shop quite a bit and I have to sort of schedule in time where I'm like, Oh no, we're just gonna go to the gym, or we are gonna go climbing, or we're just gonna go out for dinner and not have to talk about work stuff, even though I really want to talk about work all the time. But yeah, that's super.


Or you know, whenever you call me up again, it's to serve my friends. So it's like I, that's it. That's my hack to keep. Yeah. So I just feel like, you know, I'm there to support all of these and none of them are mine. That was really hard though, because again, as my identity, that was the only way I could get


Fully agree with that. Mm-hmm. . And then it also, that also led me into trouble too. Okay. Because the whole reason I sat happy, not perfect was that I only did it out of service to other people's mental health. It was that I'm setting up this company and so I actually killed myself because I was just wanted to be in service.

So when I was being bullied or when I was being terrorized, you know, I almost kind of started playing the. Like, I'm gonna take this because I am serving other people. And that's probably what kept me going for so long, in all honesty, is being of service. But I learn almost going into spiritual flight that is also an escapist tool.

I actually had to come down from spiritual flight. Just to face my reality. Yeah. Of what were huge wounds. And I needed just to nourish them and nudge them with just some of the basics. So I think it's like everything in moderation, it sounds like that really works for you. And I think maybe the nature of the company, because it was around serving people mental health and like, and I was receiving so many messages every single day saying This app has changed my life.

This app has stopped me from committing suicide. I dunno what I've done without this app. And so even more and more and more, this element, I need to be in service. Yeah. Like their wellbeing is more important than mine. Like it's okay if I suffer because other people are benefiting and that's okay. And this is where I find studying kabbala really helpful, which is an ancient spirituality.

It's an ancient form of Judaism for the last 10 years. And I have a teacher called Marcus, who always tells me to lean into what I find most uncomfortable. I find it more comfortable being in. Being a martyr. I find that easy. Actually. To me, that's an easy way to live life. Classic people pleaser ca.

Classic people pleaser. Yeah. Yeah. So for me to kind of move into what I find uncomfortable is how do I look after myself today actually? What is right, Because at the end of the day, otherwise I'll just fall into burnout and then I can't help anyone.


Mm-hmm. Cause once you do start serving, everyone starts coming to you for more and more and you're just like exactly like yours is, and something, the bottles just so fall up and you'll just get overwhelmed. And then that boundary is just, you have to really figure out what that is. That defense is otherwise.

Yeah, it just, it's like a tidal wave just comes at you. So how did you set the boundary of, Hey look, this is the people I can help and this is what I can do because you wanna try and maximize to help, but you need to protect yourself. So how did you manage that


Yeah. And there is almost like no formula for the kind of knowing. What feels right because it is, it's that kind of weird spirituality, gooey, fluffy space that we can't quantify in many ways. I can't say to myself, I'm gonna do 10 today, or 20 messages only because sometimes I'd have energy five, sometimes I'd energy for 55.

So, Another person who I think speaks really well to, you know, really accurately to this is a girl called Jenna Zoe, who really focuses on human design. And one of her main messages is what comes easy to you in life, and that is your sacred gift. And I guess with entrepreneurship as well, I think it's really easy to build a company that you absolutely love and then you end up doing the jobs that.

Are not aligned with your sacred gift. Do you know what I mean? You're suddenly, you were, you were a creative and then you're just stuck in the admin. Yeah. And after a while, you got really drained and you're like, God, why is this not as fun anymore? There's a whole


One of the things I want to talk about is a bit more about the shop side of things. So when you started, you raised the investment, you got the app, and then you mentioned an inflection point. As to when things really ramped up and just went crazy and, you know, millions of downloads and, and whatever. How far had you been going along at that point and what actually led to that exponential


Well, I think the exponential growth really came when we pivoted to also servicing b2b. Mm-hmm. . And suddenly we found this incredible B2B partnership that then ensured that the app was suddenly available to a hundred million teachers. Person, students. Yeah. Wow. And that's when it was this idea I'd woken up in the middle of the night with to suddenly, five years later, we.

Or exposed to bigger deals. Right. Yeah, it was huge. And that's where I really saw the power of B2B actually in, you know, combining communities and how that deal came about again, was really. Serendipitously, it was certainly not in front of a laptop, just like firing off emails. I was launching Pop & Suki in Shanghai, and my investors at the time were not happy about it because they thought that this meant that I wasn't completely focused on Happy Not Perfect, but on being out in the world is.

Some of the most valuable things that you can do for your business are. And I always think pounding the streets, whether that just be going to industry events or just being out there talking about your idea, that is when serendipity can happen. Serendipity is very difficult to happen when you're at home.

And I remember being in Shanghai and I met a guy and he said, Oh, you know, what do you do? I said, Oh, I do Pop & Suki, but primarily I've just launched a tech company that focuses on mental health. And he said, Oh, you should meet this guy. I set a meeting. Suddenly, within three days I was flying to Canada to meet the CEO to start the negotiations for this deal.

Wow. That's quick and well, I know it was, but it. Do you create your luck or is it lucky? I don't know, but it was a lucky moment and I couldn't have planned it. When you


I really look back on it with positive energy, like going back there. I haven't, you know, after just sharing with you some of the things that happened, even brings me back because, in all honesty, I was learning so quickly, and I can't also blame it all on these investors. I was a very young, deeply inexperienced entrepreneur.

Me now. I wouldn't have even let that happen. Mm-hmm. You know, I would've put the boundaries in place. I would've formed a relationship that was appropriate and acceptable. So I also, I'm gonna take some of the blame here. Do you what I mean, I'm not sit here and say it was… No, I was probably a nightmare to have invested in, you know, and I was, I knew what my idea was and I wanted it to do it my way.

You know, I definitely had some learning curves that I, um, I shouldn't have done, probably. It got to the middle and actually towards the end of the company, everybody had suddenly relaxed because at this point, and don't get me wrong, I hardly owned anything of the company at the time of kind of acquisition.

So it's not like my life has changed. Um, but. It wasn't about the equity for me at the end. Happy Not Perfect. To your point of being in service, happy, not perfect was bringing something to the world that I really thought needed to be in the world. I do look back and think, Wow, that was an amazing life experience, and it made me reevaluate what success means.

I think in our culture, we can think success is only a big house, a big paycheck, whereas success has never really truly been that. For me, it was. I set it up with impact in mind and I sold with huge impact in mind. That was a success. I


You, and, and you remember you've won. Yeah, no, I was like, you, but not, not, not just from the acquisition side of things, but. Truly, from what you just said, the impact that you're having, the millions of people that are gonna be using this app, and how it's gonna grow. Now it's in the hands of another company, you know, and the, the exposure that it's gonna get.

brother up with, you know, at:[:

Yeah. Isn't a to know three. Yeah. I'm back at the next company and. I think to myself, God, this feels quite masochistic. You know, kind of like going back in, I've just just told everyone, like being entrepreneurs black,


The community of entrepreneurs. My dad is an entrepreneur. I just think it is a privilege to be able to create something that wasn't in the world, you know, before you came along. And, you know, I remember when I was little, my dad invented, um, him as his business partner invented the Cling film Cutter. Oh wow.

The Bio gradable pink film content . That's amazing. We were taught to invent, you know? Yeah, yeah. It was. If you want something, go build it. And yes, it's another up-and-down road, but if you can look after your mental health religiously, I think we can all do it. I think it's, and as I said, it's, it's a privilege.

So I'm back building, but I did take some time just to heal. So


We are waiting until we get really stressed out to then start. Meditating or whatever intervention, any tool you're gonna use. But I thought, well, how do we stop people from getting to that point? How can I intervene higher up the stream? And that's why I got obsessed with sleep health because as we all know, if you sleep better, you've got better relationships.

More productivity, better health. To me is like the golden bullet of being human, which is getting better sleep. And clearly Dr. Rupe, you are the king of this .


Oh, amazing. Which I. So excited about it. I think that my other big piece of advice is co-founders are great when they're great. At the time I didn't have that many friends who were doing similar things, and so I think, you know, talk about my mom. She was almost this co-founder in many ways that I would, and she was a psychotherapist so I could call her up and actually talk to her about the mental health content to actually.

You know, just complete moral support. But in this new business, cuddle, I have an amazing co-founder. How'd you guys met? When he was doing his past business in CPG. He's been a CPG for 10 years. Okay. Worked at Heights, BA beans to Coco Water set. AdOne Fizzy drinks company. Oh, he is on a start-up up as well.

Yeah. Okay, brilliant. Scaled it in America. Yeah, I mean, he was one of the best founders I had met. Like eight years. And when I was in New York and he was in New York too, we met up because we had a mutual investor and they put us in contact. And I honestly think we, both of us must have been in tears in our first meeting, like kinda sharing the struggle.

Right? And so we just instantly had this bond. And what's so strange is I've been waiting for him to finish and um, anyway, so I reached out to him. Cause I saw on his LinkedIn status it had changed. Like a new job or something. And I thought it's huge now this time. See how of a relationship. Yeah, yeah, yeah.

and I messaged him and I said, Would you wanna collaborate on something? And uh, he responds being like, Yeah, what are you thinking? And I said, Well, I'm really interested in working in the sleep space cause I'm obsessed with sleep health. And he said, This is so odd. And he sends me a picture and it's an entire al sheet of paper that says sleep recovery and.

An arrow. It says Poppy, Jamie. No. No. Yes. What?


Yeah. I do kind of like to use this word tentatively. Whatever you, however, use it. But I give up to God, You know, you give it up to the universe. I put something into motion and you know, you know, like either something goes quite naturally and suddenly these serendipitous moments happen, or, you know, this is not my first idea after happen.

Not perfect. I've come up with five others. I was gonna build a community therapy app called Heartful last October, and it was all gonna be about group therapy. , it was sticky, built the deck, had a first investment meeting, and it just didn't go. And so I know what it feels like when the world is showing you signs that this is not right for you.

And when the world is kind of giving you a bit of a kind of push forward. And this was a push forward sign to me when he sent me back that piece of paper.

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