Investing, Fundraising, and Podcasting: How Perseverance Leads to The Greatest Successes with Josh Muccio

27:44How are, how do you see the business of what you do differently after having taken a step back? What changes manifest? I think, I don't even know what it is. It was basically, I was just letting go of essentially a, I thought that the pitch was me and that that was what gave me importance in the market. And I realized that that was just completely a lie. Like whatever I was doing, I would be giving that thing. I would be the one making that thing important. Like whatever my time is spent on, that's what makes it valuable. And so it was not the pitch giving me value, but it was completely the other way around.

28:23And I know that maybe doesn't sound like a huge paradigm shift, but for me, that was, that was everything. So then it was like, all right, what is next that I'm going to do? And I'm not thinking about, oh, there's this pressure because the pitch is the last thing I did. It was just like, I'm going to let that go. And whatever I do next, it's going to be great because I'm going to be working on it. And it wasn't even about the success metrics of what other people said about the thing. Does that make sense? Totally. And I've been there. This is why I was asking. I do understand that there has to be an uncoupling of your personal brand, your personal identity in the business itself.

29:04So that's why I asked. So you decide to do what with the show when you say, okay, I've let it go. But obviously you haven't. So tell us the transition. Yeah. So then in early 2022, we realized... So during this time off, I kept thinking about, okay, what's the next thing I'm going to do? We basically decided, all right, I guess the pitch is not it. We're just going to let the pitch die. And every idea I would come up with, every business idea that I would get excited about, it was just like, oh, but if I had the pitch back, this is how I would launch the thing. It was just like, oh, I would launch this product for entrepreneurs.

29:47Oh, if I only had the show, if I published with the show and I promoted the thing. Like it could be really great. Like I have this amazing audience and it just like thing after thing, it was like every idea would be better if I had the pitch back. And one of them was to start a fund and to start investing in companies similar to how the investors on our show invest in companies. But it was, there was enough where it was just like, all right, the pitch needs to be ours again. We need to bring this show back. Of course, listeners this whole time were like, you know, asking us what's happening. And I wasn't sure.

30:22And I, I felt like I couldn't, I don't know. I'd been so honest with listeners up to that point, but I felt like I couldn't be honest about this thing where I wasn't sure if the show would come back or not. And if I had known for sure that we were ending it, I could have come in and say, the show's over. I'm so sorry, but I couldn't even do that. So I was just silent for like a year and a half. And then when we decided like okay we want to bring the show back we talked to spotify and they were like okay we don't want to bring it back here at spotify budgets are constrained we're like letting go of shows and you know this whole process has been of basically unloading all of the assets that they bought with gimlet has been ongoing for a couple years now and so i was like well what if i bought the show from you guys and just took it independent and they were like oh yeah yeah we could do that oh really and so we did i mean it took a couple months to come to a deal but we bought the show from spotify took it independent and uh pretty quickly after that partnered with another network vox media they you know produce and uh distribute shows like recode and pivot and prof g and a bunch of other um also great podcasts but very different from Gimlet.

31:38And yeah, we partnered with them this time. So we didn't sell the IP and relaunched our show in June of 2022 and launched a fund around the same time. Okay. So this is where I want to pick up part three of this story. But before we do that, I think the business question comes up for me is when you decide to buy back from Spotify. So So Gimlet sells to Spotify. So venture-backed media company sells to mega tech company. Then small business owner creator wants to buy from Spotify. Can you connect the dot? Because it seems like that's a, you know, a David and Goliath type thing. And like, how much liquid cash are you sitting on?

32:25Like, what does that even look like? Like, when I think about buying a podcast, like, how were you intimidated? appreciated like what does it even look like like because i'd already sold it to gimlet a few years ago so like which at the time that was kind of a big deal because people like what you can sell a podcast it's like well yeah it's an audience like people buy and sell audiences all the time um i don't know you know it did seem strange at the time for podcasts because it felt so nascent it was felt like you know people in their garage like you know recording a thing and um who would want to buy that you know um but it turns out certain properties uh are really valuable and ours because it's in the business niche advertisers really like to advertise on business shows because it drives incredible roi and so our show was profitable inside of gimlet so yeah i mean all of those things don't make sense as to why they would let it go but i mean it was weird things were happening inside of Spotify.

33:23They, yeah, they, they're a tech company that bought a media company and didn't, didn't really know how to run a media company. So, um, anyway, yeah, I mean, buying the show was just like, uh, it was just a series of conversations. Like they're, they can't do anything with it. They're not like, I'm the host of the show. I mean, they could like buy enough, you know, put somebody else in there, but like, they weren't going to do anything with it. So they might as well sell it to me. So in that sense, like in the business sense, like position yeah like when it came to buying it back from them you're like as of now what i've learned is my value isn't derived from the show but essentially my my value is the show and so sure you don't want to sell it to me no problem i'm going to go out and do my own thing anyway and so did you did you say like you like you stand to make a sale and i'm okay walking away Like, how did that affect the way that negotiations happened?

34:20I mean, I think like, I don't really know because it was just, you know, their lawyer talking to my lawyer. Okay. You know, I had friends inside of Gimlet who basically helped vouch for me and helped put in a good word. Right. Because I think the biggest concern is that we put in a request to buy the show and they completely ignored us. But they didn't ignore us because basically we had friends inside of Himlet who were going to bat for us. Yes, your network is your net worth. So I want to tell now from a listener's perspective, it's 2021, right? When you guys come back? 2022. 2022. So you come back in 2022 and you come back in a big way.

35:04and you come back with a fund. Now, I remember seeing the show pop up in my feed and I'm like, they're back. And then I had to wrap my mind around how the show is different and what it meant for you to come out with a fund. So can you explain the fund in like, explain it like I'm five because I want people to be a part of this journey. And then I want to tell listeners that I inserted myself in this part of the story. So explain it to us. Yeah, you're part of the story now. Okay. So yeah, the story of the fund, I mean, it's very simple. Basically, we just like a stock market money manager would take a bunch of companies that he thinks he or she thinks is a good investment and bundles them all together and then says, hey, Jasmine, this is what I'm doing with your money.

35:54You're invested in all of these companies. I do the same thing in the private market. So with companies, early stage startups that are just getting their companies off the ground, They hope to someday be the next Facebook, the next Uber, the next Twitter, you know, whatever. Like they're trying to change the world. And the best way they think to change the world is to use their company and to build something that tons and tons of people use. And so we try to identify who those people are, invest in their companies. And it's not like a stock market where you can like actively trade these things.

36:28You buy in once. It's not a liquid investment at all. It takes basically 10 or more years for these companies to mature and to hopefully build something of value. But it's a very unique asset class that, you know, when done right, can actually outperform the stock market. So that's we basically took all of the information that we learned running the show, working with venture capitalists who were the panelists, the investors on our show for all those years. and being able to go back and look at what were the good investments they made on our show and learn from that was essentially the thesis for starting the fund.

37:06But what was so cool is like most funds start and they pitch institutions, they pitch family offices, right? They pitch high net worth individuals and they just like pound the pavement trying to raise the fund. We did not do any of that. We just published an episode where we told the story of what had happened at the pitch the past couple of years. This was in episode 101, Josh pitches the pitch. And we asked our audience if they would like to invest, which used to be illegal a few years ago, but the SEC changed some stuff. And now, you know, you check a few boxes and you can publicly raise. And so we were able to raise our fund.

37:45We're tracking towards raising about four and a half million dollars in our first fund. And it's raised entirely from listeners of our show. Okay. So let me pause here and break this down in the most simplest of terms. Back when Gimlet wasn't acquired by Spotify, I was listening to a show called Startup, and they gave for a brief amount of time the ability to invest in Gimlet. Did you invest? Well, what I didn't know at the time was I was like, I'm going to invest. and I was going to invest because I just loved everything about it. And I believed in it because I was a massive consumer. And I'm like, if there are people like me, then it's going to be hands down the best investment that I could ever make.

38:30Now, there were times in the past, Josh, where I missed on these very blatant opportunities where I live in Southern California and there was a store that descended from Canada called Lululemon. Now we say that now, but when there was like a line of women outside the door, my husband had asked me, do you know what that is? He's like, do you think we should buy stock? And I'm like, no, that's just for crazy women who really like to work out. And next thing I know, I was one of those crazy women standing in line because I swore by these bands. You know, you see these like with other coffee shops, you see these opportunities.

38:55So I just knew I was like, oh, Gimlet is my future Lululemon. I didn't know at the time that we had to create an AngelList account. And it took a long time for it to like be approved or go through. So I was like, I'm going to invest in Gimlet. And when they had announced it, it was that day that I decided to go through and create an AngelList account. or a profile. And I was far too late. They sold out like less than a day. And I was like, that is my greatest regret. And so then, well, now I went through the AngelList process. And so when the pitch comes back and says, we're raising a fund, I have to be honest, I didn't understand what a fund was.

39:37And so this is back in 2022. I mean, like, gosh, it's like, oh yeah, Jasmine, this is like two years ago. But hey, I'm just letting you know, this has been my journey. And it was different than what Gimlet was asking for. Now, on show 101, Josh pitches a pitch. You were very candid that you were getting a little bit of heat from different people asking, well, does that change the nature of the show? Since the show has a vested interest in these entrepreneurs who are pitching, does that change? And I remember listening and this is where as a business owner, I'm looking at this is saying there is a multitude of funds.

40:13If you have money and you want to invest in a fund, which basically means somebody else will be making investments on your behalf and you're patient enough eight to 10 years to see how that actually played out for you. I can go anywhere, but I am choosing a fund based on somebody I trust. And that came on the back of listening to a show again and again. And I talked to my husband and I said, we need to get into this fund because whatever we invest in the fund, it will be less than what I would have paid for an MBA to learn everything I have learned. So even if it's a bust, even if it's a bust, I just paid for the investment of education that I had learned.

40:50And I will say that in order to invest in the fund, what was the minimum to invest in the fund, Josh? 10 ,000. Mm-hmm. And so I reach out to you. And at this point, I actually think the fund is like a popularity contest. I'm like, I need to pitch myself to be a part of the fund. And so I remember emailing, not you, but like, it was like, I don't know, like the pitch at the pitch or something like that. It was like a corporate email. Oh, was it? Okay. And I was just like, so I am essentially telling myself, I'm like, I think that I could be a value add because I would love to help the pitch grow on social and expand its reach.

41:25I am literally begging to be a part of the fund. Yeah. And I I remember this. And it led to a conversation that I had an opportunity to meet with you and Lisa. And we had a great conversation about what it would mean to grow the pitch socially. And that was that. Now, what I want to do is I want to bring everybody up to speed with October 2023. Can I read something? Yeah. Okay. Hi, Jasmine. As an active investor in the fund and the Gemist and Tether SPVs, I'd like to personally invite you to join me, Lisa, and the rest of our team at The Pitch Miami. me. We only have room for 10 people to join us on January 11th or 12th.

42:02So I wanted to open up to LPs first before we opened it up to the general public next week. This is our first ever VIP experience and invite only. We're handpicking a mix of LPs, angel investors, and VCs to join us at the studio. The idea is to give a few of our most active LPs the chance to meet founders on our show at the earliest possible moment. And then we will host a special dinner in the evening for investors. The cost is, and we can talk about the cost or not. I wanted to not put that out. Oh, I don't care. Sure. Okay. The cost is$3 ,000 and it includes lunch, dinner, snacks, and a full day of live recorded pitches with your peers, the pitch team and investors of the show.

42:37So how would you like to join us at the Pitch Miami? I am telling you, Josh, I'm trying to be such a professional podcaster right now. And I am battling a cold Josh. And I am like, keep it together, woman, you will not cough into this microphone. And I am sucking on this cough drop. And so people are going to be listening. Like, is she chewing a taco? No, y 'all, I'm trying to keep it together. I read this email in our kitchen and I can't even get the words out. I can't even finish half the email. Cause I turned to my husband, my business partner, my high school sweetheart, the guy who believes in big dreams.

43:07And I'm like, we're going to Miami. And he turns to me, he's like, what? I'm like, no, no, no. We're going to drink Cubanos and we're going to be on South beach, baby. And we're going to go to this. And he's like, wait, what are you talking about. So I explain and he says$3 ,000. And he said, do you want to know the ROI on$3 ,000? I get to sit and watch not one, but five companies do something that maybe, maybe in the future, or maybe not. I am getting a front row freaking seat to see how the game is freaking played. The game, which is traditionally, and I'll just come out and say it, not been all that inclusive to women, underrepresented groups, and people of color.

43:47The amount of Latinas who ever get to pitch to an investor, the amount of people who get to pitch, but the amount of people who actually get funding is less than 1.5 % for Latina and female founders. The fact that I get to see in the room and be in there and watch, how do I play this game? And how do I find a way to win? If that's ever something I so decide to do. So he says, let's go in. That's it. I respond to that email. And then a few days later, Can I read something else? Yes. Okay. Sure. I'm like, what do I say now? I know. No. It's what do I say now, Josh? Oh, okay. Okay, good. Hi, Josh.

44:24Happy Monday, and I hope you're gearing up for an amazing Halloween. My daughter made a special request for our family to dress like her favorite story, Little Red Riding Hood. She said she wanted to be the wolf, a girl after my own heart. Two questions. Would I be able to create a vlog about my experience going to the pit show? It would be a behind-the-scenes look at why I was invited. what I find valuable as attending, and what I will have learned. I'll be sharing it on my social channels as well as my newsletter, a total combined reach of over a million people. I would like to take a handheld camera for video clips, but I'd be discreet and not intrude on recording endeavors.

44:57Number two, would you be interested on being a guest on my podcast? I'd like to talk to you about your entrepreneurial journey and the show. Let me know what you think. Both, one, or none, the options is totally fine with me. But if there's one thing you need to know about me. It's that I love to create synergy, magic, and expansion with content. I'd be honored to co-create with you. And Josh, that is what leads us here today. So I want to say thank you for that. Oh yeah, that was an easy answer. We're very excited to have you at the event. Yeah. And here's the beautiful thing about this for people who are watching or listening is if you have your chance to shoot your shot, shoot your shot.

45:33I was completely unattached because the win, I'd already won. I got into the room. I am a get in the room kind of girl. And if the door is closed to me, I'll find a window. I'll break off the roof. And little did I realize that making an investment into a fund that I believed in based on a personal brand and trust that was built over year after year after year. So I get into the room. And so I'm like, what do I have to lose? Nothing. And here's the best, most surprising part is that this podcast serves as a podcast. It also serves as a video, but it serves as a testament of what is to come because I will be creating a blog and I will be citing these things.

46:06And unbeknownst to me, I get an email from Lisa, Josh's better half, let's be real. And she says, do you think that you would be able to share some of your video clips with our team? And so here I thought, more synergy, more magic, more co-creation. And so this is why I wanted to have the show, Josh. I really wanted to document the journey of you as an entrepreneur, the journey of your ability to first and foremost, listen, that the thing that you're doing now might not be the thing, but it could lead to the thing. And then I want to talk about the entrepreneurial journey about co-creating. And then when things don't turn out the way that you had expected, and then letting go of the lie that you were the most valuable thing to the business and that the business was the most valuable thing about you.

46:52And once you uncoupled those two things and you understood that you could do whatever you have done before, but better in less time, you then go out and say, I'm going to bet on myself in a way that I never have before. I will retain the IP. We'll find a partner. And then we're going to do it better. And we're going to do it different. And despite the outward opinions about how the show will change, you still know what is best for the show and what is best for listeners and what is best for business owners who are raising funds. And from an outsider's perspective, as a viewer and a listener, I find it so valuable that the investors on the show, you really aim for diversity.

47:28That people who are pitching the show, it is a wild misrepresentation of what is actually happening in venture capital and Silicon Valley, because there are every color of the rainbow, every gender, disabilities, and not women, men, everything under the rainbow. And I listened to this and I say, you guys are creating the future of what venture capital should and will be. And so I want to be a part of that. And I want to take my listeners and people on YouTube and just be like, I'm documenting the journey. I want to say, thank you for that. Thank you for making a fund for this Brown girl to get a front row seat.

47:59So what it actually looks like. So thank you. Thank you. You're welcome. We're psyched. We are so happy to have you come and join us at Miami. I mean, like, this is why we started the fund. It's like we really believed that we had incredible people listening to the show. And the only way we'd ever worked with them was to say, listen to the show and we're going to make money off of ads. You know, like, so like there was no relationship with our customer other than you listen when we publish stuff. and so we were just really looking for ways to actually engage with our audience in a deeper way and the fund made more sense to us than just like starting a patreon or doing something like that which is you know the typical uh the typical podcast path so yeah i mean and josh have you seen this i mean we're closing the conversation i mean we are going to close the conversation but there is something i have not seen this done anywhere else no i'm not saying that you guys are like unicorns the first to ever think this way but you guys are definitely the one percent of people who are doing this, which is fascinating to me.

48:59You guys are creating an entirely different monetization model, so different than what other people are doing. How is that working? And in closing, for people who are interested in the fund, and can you explain the difference between the fund and SPV? Because I didn't know those differences and how I've been able to extend in closing and closing. Yeah. I mean, people can join us. We still have a couple spots left at the pitch. We've got lots of LPs coming, still looking for... We've got a few VCs coming, but still open to just some angel investors in the general public who'd like to come. I mean, the idea is that if you're interested in investing in these companies, what better place to be than to meet the founders the moment they're pitching the VCs on our show?

49:38There's no greater access. I mean, you're getting the same access that the VCs on our show get. So anyway, I don't need to pitch it. People know. But yeah, it's called, I think the website is thepitchevent.com, where people can express interest in joining us in Miami. um oh the difference between the fund and an spv so an spv is just a i wish they called it something else um it's basically just like a deal like it's like you can invest in this company the deal is gemist this company we had on our show you can invest in gemist but what an spv is specifically is it's a basically a business entity that's created that allows a bunch of people to pool their money together and then invest one big check in the company.

50:28Because actually, it's quite hard for an early stage founder to sell, basically sell shares to a bunch of different investors. Like, it's, it's just really difficult to do. Like, it's, there's so much paperwork, so much back and forth, you know, terms have to be negotiated on for every single one. It's just, it's just dumb. So, So basically you pull everybody together and then basically like we as the fund managers host this SPV and negotiate on your behalf to get allocation in these deals. So that, you know, basically, you know, someone like you can put in a thousand, two thousand, ten thousand dollars into a company if they want.

51:11Okay. So as the listener is listening, I want to break this down as simple as possible. So JD and I invested in the Pit Show fund. And so part of the money from the fund, they invested in a company called Gemist. We're not going to get into it. Go and listen to the Gemist episode. It's pretty fascinating. Now, as part of us being a part of the fund, Josh and the team get to invest however they best see fit. Now, there is also an SPV. This means that any investor on the show that JD and I listen to, and we really like that business idea, we get to put more money into that particular business outside of the fund.

51:45And so I want to explain why we chose the gem is because it was the first time in my entire life that I had ever heard Of a vertical sass solution And josh I I invested in the company because I liked her as a founder But I learned so much about what she was doing that i'm like if nothing else This is my tip my hat to you doing the dang thing and I get to get a front row seat to what it is You're doing and so to me, I want to say thank you for democratizing what was otherwise, it felt like a black box and giving people like me the opportunity to get in, learn business from actual business owners doing the dang thing in the mud, missing a tooth, a punctured rib, a broken arm, a matted hair and get up.

52:26You say, okay, one more time. Josh, how do people find you and The Pitch online? We are just The Pitch. On every podcast app there is The Pitch. You should be able to find us. It's this big blue cover art with the words The Pitch on it. And I'm not super active on social. I am on LinkedIn, probably more active there than anywhere else. But basically... Give a shout out to the YouTube channel. We got to give a shout out to YouTube. Oh, yeah. We're on YouTube. You guys are producing it big time. Yeah. The Pitch Show. We just launched that last year. Yeah. The first episode actually was the Gemist episode.

53:00It was. It was. So, y 'all... People seem to really like seeing the show. It is. It's fascinating. It's fascinating. Do you watch it? I, I'm, I'm, I've always been audio girl. I've always been audio. And so that's mostly how I listen to it. But every so often when I want to see the founder, so, okay, I'm going to totally nerd out. I can't believe I'm saying this. I'm glad it's at the end of the episode. I actually like looking at body language when the investors are asking hard questions. And I am actually looking at the time duration of facial expressions, body language, and how long it's taking for them to respond to the question because I, I'm, I'm a watcher.

53:35And so if i'm looking at the body language if i'm looking at the face I need to know how do I possess that same type of power that I hear audibly because visual is a major distraction in human human interaction So I hear the audio and I could hear the palpable pain discomfort awkwardness of it But how does it come across conveyed that is something that I need to master and the video has helped me do that So whenever I hear it, that's when I would go back and look at the visual of it Is there anything that surprised you in watching the show that you didn't expect? um, yeah, the um, the the gentleman the the product designer for Apple, the one that does the touch, like the pointing.

54:10So I knew that he had, for all intents and purposes, he had said he had a disability. So I wanted to know how his disability, how did he approach the mic? How did the disability convey itself in front of an investor? So somebody with a physical disadvantage when investing, how did he leverage it so powerfully as an advantage? Audibly, you heard it palpable. I was like, Like this guy is unmessable with, like unstoppable. I would, you know, I just want to throw money at him. And how he showed up on camera was very different than what I heard the power in his voice. And I said, Jasmine, how might you possess the same power and confidence in your voice, despite how you might feel on the outside?

54:49And that was like a big lesson for me. So I'm a consummate learner. I'm a studier, Josh. I'm a studier. Yeah. No, that's super helpful for me. Thank you. Oh, well, thank you. Y 'all, The Pitch on every podcasting outlet to get to know more about what they are doing. You can connect with Josh on LinkedIn. Check out The Pitch on YouTube. And y 'all, be sure to follow both of our, subscribe to both of our YouTube channels because I want you guys to get a behind the scenes look at what it looks like from a viewer and participator and investor's perspective. Thank you for listening to The Jasmine Star Show.

55:22If you have found that at all interesting, please make sure to leave a review. We are indebted to them and I appreciate you being on this journey. A thousand times over. Thank you again to listen to the Jasmine Star Show.