Startup Success with Prerna Gupta

January 25, 2022
James Whittaker

Check out this episode on the Win the Day Podcast

Only from the heart can you touch the sky.

Rumi

Welcome to our first Win the Day interview for the new year!

Today we’re joined by Prerna Gupta who has launched entertainment apps that have reached more than one billion people. As an unstoppable force in entertainment and tech, Prerna’s work continues to impact all corners of the globe.

She is currently Founder / CEO of Hooked, an award-winning storytelling platform that reaches 100 million Gen Z viewers worldwide. The Hooked app has been #1 on the App Store and Google Play in 25 countries and has won numerous design awards for its innovative format.

How influential is she? Well, investors in Hooked include: entertainment superstars like Ashton Kutcher, Jamie Foxx, and Mariah Carey; sporting champions like Steph Curry, Kevin Durant, and Lebron James; and renowned talent agency WME/Endeavor.


Check out the YouTube or podcast version where Prerna Gupta does the Win the Day Rocket Round, answering questions about her favorite quote, what advice she’d give her 18-year-old self, the one thing on her bucket list, and a whole lot more🚀


Prerna has also been named one of the Most Influential Women in Tech by Fast Company, and her writing has been featured in New York Times, Vogue, and TechCrunch. 

In this episode, we’re going to talk with Prerna about:

  • How she went from struggling startup founder to amassing 1 billion users
  • What steps enabled her to get a team of A-list celebrity investors
  • When to persist or pivot (or surrender) your business, and
  • How to finally create true freedom in your life.

Before we begin, the right bit of inspiration can completely change the trajectory of someone’s life, so if there’s a friend or loved one who needs to hear this episode or could use some help to Win the Day, share it with them right now.

Let’s WIN THE DAY with Prerna Gupta!

James Whittaker:
Prerna, so great to see you. Thanks so much for coming on the Win the Day Show.

Prerna Gupta:
Pleasure to be here.

To kick things off, is there a specific memory from when you were younger that's still so vivid for you today?

Yes, I actually remember when I was six or seven years old and you think about, “What do you want to be when you grow up?” And there were two things on my list, I couldn't really decide between the two, but one was a writer, I really wanted to be a writer, and two was an inventor. I thought inventors were really awesome and had this dream of inventing something one day.

In many ways my journey as a founder has allowed me to realize both of those dreams.

Your family emigrated from India, and that can instill certain values around making sure that the opportunity is not wasted, especially after a very brave decision to pack up and move to the other side of the world.

Were there any expectations or specific lessons from your family with regard to work ethic or career direction?

In terms of expectations, it's a trope, but immigrant parents tend to have very high expectations of their children and a lot of that just comes from their desire to make sure their children have stable lives, because we don't have deep networks of family and stuff to rely on. So there were definitely expectations that I would do well in school, that I would go to a good college and ultimately have a career that made a good amount of money.

But at the same time I feel like my parents are entrepreneurs. It's very entrepreneurial to leave everything, especially back then in the 70s and 80s there was no internet, I remember for them to call their parents was such a big deal. It was like making a phone call was so expensive and it was a terrible connection, and so you're really isolated, you're coming out, you're a pioneer, and all you have is your degree and your education and then your own confidence and belief in yourself. I learned those values at a very early age from them.

Ultimately, when I decided to become a founder, I was pretty young, I had just graduated from college six months earlier, and I was working in a venture capital fund in Silicon Valley and I just hated my life.

I was working in a venture capital fund in Silicon Valley and I just hated my life.

I had an idea for A business I really wanted to strike off on my own. I remember calling them saying, "I'm quitting my job, I'm doing a startup." And they were shockingly supportive! They believed in me and it was really that pioneering spirit that they had that carried through to me and I really appreciate their support through all the ups and downs.

You probably built up a good track record by then of making some good decisions, so maybe it made it a little bit easier for them to trust you with that next path away from the traditional and stable route.

I think I had a track record of making many bad decisions also, so it could have gone either way.

Law of probability, she's due for a good one!

Yes!

It sounds like a lot of great lessons you mentioned have carried through you not just through your journeys and adventures that you have taken, like Costa Rica that led to the Vogue article, but it looks like you've instilled a lot of those values and beliefs in the business interests that you've had along the way too.

Yes, absolutely. I do think, in a lot of ways, entrepreneurship is a mindset and it's a way of life. It's not just about how you build a business, it's about how you approach your personal happiness, how you manage your time, and how you interact with other people. 

Entrepreneurship is a mindset and it's a way of life.

I've also been very lucky, I co-founded all of my companies with my husband, Parag, and that's not an arrangement that would work for everyone, but it works very well for us. So he's my co-founder in work and in life.

One of our favorite startup books is Lean Startup by Eric Ries, and that's a philosophy that we really implement in our own lives as well as in our business.

What do you and your husband focus on specifically to make sure your relationship remains strong while staying true to the business and its stakeholders?

Yes, it's definitely hard. As you mentioned, the entrepreneurial journey can be so emotionally draining and there's so many ups and downs that you go through, and when both of us are going through it, when there's a down and if both of us are experiencing that at the same time, it can be really tough. 

But for us it's a couple of things. One is communication, just open communication, always being just very transparent with each other with no drama. For the most part, we don't argue, we debate. If there's a disagreement about something, it's really, okay, here are our points, each of us gives our points and generally the person who's right ends up convincing the other person. 

That objective approach to decision making and just being very open and transparent and keeping the drama out of it has been really important to our success.

We've been together for 17 years, we've been doing this together basically that entire time, and so we have a really strong intuition about how the other person is feeling. And when there's that emotional up and down, where is the other person on that roller coaster?

When things are really great, experience that joy but don't let yourself get overly elated and that will help you when things suck to not get overly down.

We just do a great job of balancing each other. So there's a day where I wake up and I'm feeling down, he senses that immediately and he keeps me up, he's happy that day and keeps me up. And I tend to do that as well for him and that helps a lot.

I'll mention one final thing just related, but we mentioned that roller coaster, this is important for every founder, you can't let yourself ride that roller coaster too much. And what I mean by that is there're going to be highs, there are going to be lows, the best thing you can do is just stay as even keeled as possible. 

So even when things are really great, experience that joy but don't let yourself get overly elated and that will help you when things suck to not get overly down. And we try and both really practice that in our lives.

You mentioned the highs and lows of the entrepreneurial journey. Is there a particularly dark day that you can take us into that you've experienced personally on this entrepreneurial journey?

Yes, well I've had many, but probably my first one that really stands out in my mind, so we've done three startups together and our first one was a social networking site for Indians. We started it in 2005 soon after Facebook had raised a $12 million Series A, which seems like such a tiny amount in retrospect. 

We were both from Silicon Valley, I mean, I had just, like I said, I was six months out of college and most people thought it was insane that this weird website was raising $12 million. But we saw the energy and the momentum that they had amongst our peer group, we were all on Facebook, we were using it, and we felt like this was going to be something big all over the world.

So I decided to quit my job and we moved to India to start the Facebook in India. We stuck with it for four years and we had some success, we had 2 million users at one point in time, getting good momentum in India for a while. And then of course Facebook entered India and completely ate our lunch, Facebook became the Facebook of India. 

Four years in we still had some money in the bank but it was clear that there was just no chance, we had tried some pivots and nothing was working and he and I together had to make the very, very difficult decision to give the money back to our investors and shut the company down.

And that was definitely one of the darkest days that I had, had up until that point in my career and was a really tough decision. It took a couple of months to recover emotionally from that, but it was one of the best decisions I've made because that allowed us to then start our next company which we started very soon after and ended up being a success.

Two million users is amazing in any market except maybe India!

Exactly, given that they have a billion people, yes!

During these early stages, what motivated you to keep going when most people were writing you off and you hadn't achieved the success that you wanted at that point?

Well, it's a very perceptive question because you are out there on your own, everyone is writing you off. And back then especially, being a founder was not cool. I mean, when I quit my job I remember I majored in economics at Stanford, all of my friends were in consulting and finance and four years into my failed startup they were off to business school at Stanford and Harvard, and here I was just with nothing to show for my decisions, and they thought I was crazy. But everyone was writing me off.

There were those days where I woke up just asking myself, what am I doing? And why am I doing this? And do I still believe in myself and in my dreams? And every time I asked that and really dug deep, the answer was, I'm doing this because it's the only thing I can see myself doing. 

I'm not going to go back to that stable career path because it just doesn't inspire me.

There wasn't really a question, I'm not going to go back to that stable career path because it just doesn't inspire me. And what inspires me is creating these products that have the potential to bring joy into people's lives, and that was really always my mission with the startups that I did. 

I honestly just almost felt like there wasn't a choice, this is what I was meant to do and the only thing that would fulfill me, and that's what kept me going.

In the absolute worst case scenario, if everything just tanked, would you feel comfortable going to a corporate job or are you an entrepreneur for life?

I'm an entrepreneur for life. I really can't do it. I mean, obviously, when there are certain situations where a founder takes the golden handcuffs or whatever when you sell a company, and that, that would be the only time that I could see myself doing that and it would be for probably a short period. But it's just really not in my DNA, I'm truly a founder for life.

I really also value the opportunity to build teams and to create work cultures that are fluid and just give people the ability to be their best selves and to really flourish at work and in their lives, and that's harder to do in very large organizations.

Yes, your big goal is to change the world, it's very hard to do that when you've got so many layers above you when you're constrained by bureaucracy.

Exactly.

Well, after you and your husband, Parag, reached a point in your careers where despite your success these self-constraints that became all consuming.

And I wanted to read you a passage from the amazing piece that you did in Vogue magazine which you wrote after making the decision to leave so much of your life behind. You wrote:

"Freedom was what mattered to me, I realized, more than status symbols, more even than making a positive impact on the world, which I believed in dearly. The drive I used to feel, the relentless need to check boxes to achieve success at all costs had all but disappeared. 

It was as though I had disappeared but in the most pleasant way possible." 

That search for simplicity and alignment it's so inspiring. What can people do to reconnect with who they are these days, especially after such a tumultuous couple of years?

Well, obviously, getting out of your own space and going somewhere else and being in nature is one of the best ways which has been so difficult in the past couple of years, so it's harder now than ever. 

But I actually think the most important thing is disconnecting from social media, from the internet, putting your phone down. I mean, I make mobile apps! But get off the apps, get off your phone. I love technology but it can definitely be a curse and there's so much noise out there and it doesn't matter, I don't care who you are or how strong your mind is, the only way to really reconnect with your center and just clear your mind is to shut it all off.

The only way to really reconnect with your center and clear your mind is to shut it all off.

I try to build in those moments in my day, in the morning and at night, where I take time before getting on my phone in the morning and I make sure that there's a significant chunk of time before I get into bed where I don't look at my phone, and that helps me center. 

And I do have a meditation practice that I do every night before bed which helps clear my mind, but it's also just important to have full days where you go and you do that, and so however you can. It's difficult when you have kids too. I mean, I have a toddler, you mentioned you have a two year old. My son is two and a half and it makes it harder to do that. 

But in a lot of ways you put down your phone and just be present, be present with your child, it'll help you even though they're bouncing off the walls I actually feel so much calmer a lot of times when I just give my child my weekends.

It's a blessing and a curse, isn't it? I actually had a conversation with my wife as recently as last night about just doing things like adding more boundaries to that technology, because if you're not aware of it, I mean, there's always an excuse that you tell yourself to be able to go and look at your phone.

The reality is that the most important thing in our life is being present with our partners and with our children. You can use it for everything. You can use it for cooking, you can use it for fantasy football, phones, text messages, emails, these things are relentless, right!?

Absolutely, that's exactly right. And like you said, it's insidious, it creeps in, it's easy to make an excuse that you need it for this thing, but every time you pick up that phone and that screen light hits your eyes it changes a piece inside your mind.

You've traveled a lot in your life and you've spent a bunch of time in places like Silicon Valley. How important is being around the right people and being around the right inspiration when you've got these lofty business goals?

It's incredibly important to be around the right people for inspiration, but we live in this amazing time where you don't have to be physically in the same place as those people to be able to connect with them and be inspired by them.

I started my entrepreneurial journey in India, then I moved to Atlanta, my husband was a professor at Georgia Tech during our first startup and we ran the company from there. We had a primarily remote culture back then in 2008-2009 when it was really frowned upon, and to explain it to our investors they thought we were crazy.

And then we moved back to Silicon Valley and obviously I really appreciate being here, I love it here. And it is valuable to be able to meet people in person, but at the same time, the world has become a much smaller place and we have advisors all over the world.

It's important too, no matter where you live, you don't have to move to find that inspiration. You just have to reach out and connect with people, and you can do that from anywhere.

Let's switch gears now and talk about Hooked, your amazing storytelling platform. It officially became the #1 app on the App Store in December 2016. What's the problem you wanted to solve with Hooked and why did it fall on your shoulders to do it?

The problem we wanted to solve was really that the fact that reading is dying. Teenagers especially are spending more and more time, as we know, on their mobile phone, in their social feeds, and less and less time reading books. 
For me growing up, books were everything. I mean, they were what gave me inspiration, they helped me understand the world and myself and just opened my mind.

You don't have to move to find that inspiration. You just have to reach out and connect with people, and you can do that from anywhere.

So the idea really came up when Parag and I were traveling after our music startup and we started to write a novel for young adults, it's a sci-fi fantasy trilogy set in Silicon Valley in the future. 

And when you travel you meet people, and we said we were writing a book for teens. And we just kept hearing this refrain, well, what's the point? Teens don't read anymore. And that really just made us sad. 

So we started Hooked with the goal of figuring out, can we change that somehow by meeting teens where they are? Meet them in their social feeds and help show them that reading can be this very engaging and very fun thing to do. And that was really the genesis for Hooked.

It sounds like books have been so impactful for you throughout your entire journey. Are there one or two books in particular that contributed most of the mindset you have today?

My favorite book of all time is Lord of the Rings, it's the greatest story ever written. And I've read it so many times throughout my life at different moments in my life, I still read it again and again as an adult. 

It's just the most beautiful portrayal of this internal battle that we have and also how it gets waged at a mass level between this intense desire for power and love. And ultimately, you can retell the story a million times in different ways, but love always wins in the end, and ultimately love is the only thing that matters. 

That has been really important to me as an individual and also in everything that I've done in my career. We really try and lead with love and to create products that help people see that and feel that.

What is it about the power of storytelling? And how can people give themselves permission to pursue their own adventurous side?

Storytelling, it's one of the greatest inventions really of humankind, it's one of the ways that we distinguish ourselves as a species. 

What it does is it allows an individual to share their unique journey and their unique insight and growth with other humans, and it can be with one other human or it can be with billions of other humans. 

It's such a powerful way for us to feel the emotions of another person's hero's journey. And obviously you can do that with fiction or nonfiction. I love fiction in particular because there's a certain growth that you have by feeling yourself in another person's shoes as they're going through that journey that's really unparalleled. 

I do encourage people to read as much as they can, whether it's fiction or nonfiction, it's also another great way to disconnect from the internet, even if you're on a Kindle, I love my Kindle, but yes, and just center yourself again.

In my life, I look back at the most vivid memories that I have and they revolve around a book, a song, or a film in some capacity. The moment that you see that, or you feel that, or you read that, it just transports you immediately back.

There's something about the emotional connection that happens through stories because even things like music, I mean, songs are storytelling as well. And I know that you've got a music background.

Yes, beautifully said, I couldn't agree more. Music is so powerful and music is the thing that brought Parag and I together. He's a professional musician, I'm an amateur musician, I'm a singer. Parag plays an Indian classical instrument called Sarod and produces electronic music. And we met at a concert that he was playing. 

And it's, I think, yes, music and storytelling, these are our two great passions and they're interesting because they both have that same impact, like you're saying, of just helping people connect very deeply with the profound emotions of being human. 

They do that in different ways. A story is really about a longer journey that you go through, and through that journey and the ups and downs and the obstacles that you overcome, you have this transformation. And music is so visceral, it's really it's a meditation and it's about being in that moment and just seeing this insight into life that's nonverbal that is just the most amazing experience.

You have an all star list of investors in Hooked, people like LeBron James, Ashton Kutcher, and Jamie Foxx. How has that celebrity clout contributed either to the product specifically or the business growth more broadly that you've experienced?

Yes, it's really been, more than anything, they have an incredible network and one of the things that has been so inspiring to me, I mean, you mentioned surrounding yourself with people who inspire you, every time that I talk to one of our investors or one of the people that they introduce me to, what I've seen is that people who are at the top of their space, whatever it is, they are exceptional people. 

One of our first celebrity investors was Ashton Kutcher, and we met at a party, at a private club in San Francisco. And it just blew me away how sharp he was.

They are not just incredibly talented in that thing that they do, whether it's sports, or music, or acting, or business, or politics, whatever it is, they are exceptionally intelligent, every single one of them. And they're also good people. They do what they do because they want to make a difference in the world and they believe in the same thing I believe in, which is really trying to bring joy into people's lives. 

So for me, just having them as mentors has been incredibly inspiring and then having access to their network is invaluable.

Yes, the ‘who’ and not the ‘how’. What high profile name amazed you the most? And how did that relationship come about?

One of our first celebrity investors was Ashton Kutcher, and we met at a party, at a private club in San Francisco. And it just blew me away how sharp he was.

Obviously his persona as an actor especially in his early stuff that he did was very different and so, I mean, it surprises you because he's a really, really smart guy, he's a total nerd. And that was really the moment where I had that realization that he's as successful as he is for a reason.

It sounds like getting a ‘yes’ has been hugely important for you, whether it's getting investors to say yes or all of the other conversations that you might have with people.

Are there any tips that you can share to help people specifically get a yes in what might be a potentially life changing conversation with them in their business?

Three tips. First, tell a story. We are wired as humans to pay attention to stories, it's much easier to absorb information when it's told as a narrative. Don't think of your pitch as a series of facts; instead, try and tell a story. If you can connect it to your own personal life some way and start with a personal anecdote or maybe it's about one of your customers, tell a story, that's the best way to pitch and to convince anyone really of anything.

Second, don't get discouraged. You're going for the yes, you are going to hear no many, many more times than you will hear yes. And it's one of the hardest parts about entrepreneurship and it's going to happen throughout the course of your journey. It happens most when you're fundraising. Just don't get discouraged, you got to keep going and not let the no’s get you down. 

Finally, try and learn from every interaction. Even when you get a no, what was the feedback that you got? And a lot of times the feedback will be wrong and not helpful, but it still will give you some information that will help you change your pitch or change who the types of people you're reaching out to. So really try and use each no as an opportunity to improve and get better.

If you were working with a solopreneur who wanted to get to that next level, what are the specific steps that you would take them through?

I would say, read Lean Startup basically. There's so much wisdom in it. It's overwhelming what you're trying to do, especially in the beginning you have this grand vision, this product that you want to build, all these people that you need to get on board, the money that you need to raise, the people that you need to hire, it's too much and it's easy to get overwhelmed and try and do everything at once.

If you start thinking incrementally and executing incrementally, you'll eventually get to a point where we can start growing your team.

Break it down into incremental steps, always build a minimum viable product, do a little bit of work, get it out there, get feedback, iterate. That's the only way, really, to build a successful company. If you start thinking incrementally and executing incrementally, you'll eventually get to a point where we can start growing your team.

Yes, Lean Startup was one of the first books I was handed when I was in business school. And you’ve done very well to get its author Eric as an investor in your company too.

Yes, very lucky to have Eric as an investor. I'm a huge fan of his and he's been an incredible mentor. And yes, I'm just a really a big believer in that methodology.

Persistence has been so big for you, but for people who have tunnel vision for their concept, at what point do you pivot away from something – or even give it up completely – versus having the persistence to keep going down the direction that you think is right for you?

Yes, it's a really tough question because it always feels like you're failing no matter what's happening. And so it's tough to know, but I've definitely had those moments where I needed to pivot, or as you said, just needed to give up entirely and move on to something new. 

For me, it's always been about asking myself, do I still want to spend my time doing what I've been doing? And is this the most optimal way for me to spend the moments of my life basically? 

When you sit and you're still and you're quiet, and you ask yourself that very honestly, you'll know deep inside, and that's the moment where you need to pivot or potentially move on. And it really comes down to opportunity costs and making the most of your own talent in your own time.

As a parent, with our second child just born earlier this month, a big part of my work is trying to figure out what we can do to raise healthy and resilient children – primarily in terms of mindset, adaptability, growth, and strength, so they can be resilient rather than to basically make sure they can keep moving forward as they face all the inevitable challenges and adversities that life throws their way.

What are you focused on specifically as a parent to make sure that you can raise strong and resilient children?

Yes, it's a beautiful question and something that we think about a lot. For me, it's really difficult, I think, especially as a mother because you want to protect them and you want to ... it's just the little things, he loves Legos and when he's trying to put them together and it's just every time I just want to grab it and do it for him, but it's that resisting that urge to remove all the obstacles and solve all the problems for them. Let them solve their own problems.

Another big one is just letting them get hurt. It's so hard to do but it's actually really important, I mean, within reason obviously. But letting them get those bumps because that's how you obviously become more resilient and also just how you learn to navigate the world and to navigate life on your own.

And I remember reading a few years ago, there was this New York Times article about, I guess, they termed it “Helicopter Parents,” and it was really horrifying to me to learn about these wealthy parents and their kids all go to Ivy League schools and they're there every weekend basically still living their lives for them. 

I personally don't believe that's the best way to raise resilient kids. A big part is that you got to let them be scrappy and learn for themselves. 

Then the final thing that I will say is just trying to be that model for them as well and showing them resilience. The interactions that my husband and I have in front of our child, I mean, we're very mindful of that and we want to make sure that they see resilience in both for us as individuals and also in our relationship with each other and then feel that strength and feed off of that strength.


Check out the YouTube or podcast version where Prerna Gupta does the Win the Day Rocket Round, answering questions about her favorite quote, what advice she’d give her 18-year-old self, the one thing on her bucket list, and a whole lot more🚀


COVID has been crazy the last couple of years. What have you learned about yourself personally during this very transitional and defining time for the world?

Yes, obviously, it's been so challenging for everyone. One of the things that has probably surprised me the most, I mentioned that we have been running our companies remotely for many, many years way before it was considered okay, and it's been really cool to see the rest of the world come around and realize that you can actually do this

Now as all the tech companies are starting to think about going back to the office, almost everyone that I'm talking to, the expectation is three days in the office at most and they get two days at home, which is really cool.

At the same time, I have a tendency to be a hermit sometimes because we have been able to figure out this virtual lifestyle. What the pandemic showed me is just how important human interaction is and just having a community is – it's so fundamental to us as humans – and I really, really missed just being with friends and mentors and peers in real life. 

It really just taught me the value as much as I, again, I love technology, I love being able to have the flexibility of working remotely and being able to connect with people all over the world such as yourself virtually is awesome, but you cannot replace that in-person interaction.

Yes, that connection is such a big part of the human experience. On your best day, what's an affirmation that you would write on a flashcard to show yourself on your worst day?

Wow. You know what, I'll just tell you, I don't know if it's exactly an affirmation, but this is just a little prayer that I tell myself a lot of times. It's funny because, I mean, I'm not religious, I'm actually atheist, hopefully no one hates me because I'm admitting that.

But it's weird because I don't actually believe in God but I have the religion gene, there's a part of me that just has this belief in something greater than ourselves. And I really value having just that feeling of connecting with something greater than ourselves and channeling that. 

So whether you're religious or not, I respect people who do believe in God, but for me, I say this little prayer to an amorphous higher power, which is: “God gives me strength, clarity and peace.”

And that's really what I strive for everyday whether it's a bad day or a good day and I try and channel that in everything that I do.

Yes, strength, clarity and peace, if you've got those three things at the end of the day that is a day well spent. So thank you for sharing that.

Final question. What's one thing you do to Win the Day?

Sleep.

Prerna, thanks so much for coming on the show!

Thanks, James. This is wonderful! Thank you so much.


As you heard, our guests love to hear positive feedback, no matter where they’re at in their careers. Share a comment on the YouTube version of this episode with your favorite takeaway so our guests know they’ve made a difference in your life today.

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Finally, the right bit of inspiration can completely change the trajectory of someone’s life, so if there’s a friend or loved one out there who needs to hear this episode – or could use some help to Win the Day – share it with them right now. 

That’s all for this episode! Remember to get out there and win the day.

Until next time…

Onwards and upwards always,
James Whittaker


Resources / links mentioned:

⚡ Download the Hooked app.

📷 Prerna Gupta Instagram.

🌎 Hooked Instagram.

🗺️ ‘Why a Tech Entrepreneur Got Rid of All Her Possessions and Lived as a Nomad for a Year’ for Vogue Magazine.

🌱 Lean Startup by Eric Ries.

💍The Lord of the Rings by J.R.R. Tolkien.

🎬 Subscribe to exclusive Win the Day videos on our YouTube channel.

🗝️ Apply now for The Day Won Mastermind (strictly limited to 12 people).

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