Special Season: Inside Summit 2024 Recap

Hi Madison, how are you?

Hi Clauds, I'm good. How are you?

Good. I cannot believe it's been exactly a week since the first ever Insight Summit?

I mean, I'm still riding the high of just the in-person energy and experience we were able to make and cultivate last week.

Truly. I mean, we've done so many events, we've done like 20, 20 in-person events, but really nothing of the scale with this level of programming. So maybe for our audience members who weren't at Insight Summit or don't really know much about Insight Summit, Mads, do you want to tell the genesis story of how Inside Summit came to be and really what it was?

Yeah, absolutely. So for all of you who've been here since day zero, you know that Claudia and I started this podcast deep in the pandemic, uh, 2020. And of course we're doing this from home. When we were able to really start getting out and about late 2021, um, early 2022, we started to see this energy when we brought together young innovators, most of whom had started their careers in COVID. And were looking to meet investors, founders, and like-minded individuals who felt like they had our shared energy. And that was really this momentum that we were able to pick up back when Claudia and I were both living in San Francisco. We were involved in the first ever SF Tech Week before Andreessen took it over and had accidentally one of our happy hours go viral. I think we had something like 400 people sign up and Location was not happy with us, but we did a lot of business. Truly, like the way that this was supposed to be a 50-person happy hour and it was almost 400 people, we had to start like turning people away at the door. And I think this is when we looked at each other and said, okay, events is a complement to podcast and we might be in a unique position to curate spaces for meaningful connection. And I think that's really where Inside Summit was born for this idea related to the podcast and was the opportunity for us to bring together who we know are movers and shakers for the next generation of innovators. But maybe you're not getting invited to like the hot tech summit or you can't pay $6,000 to go to All In Summit because that's crazy. And so yeah, that was really, I think, you know, where, where Inside Summit came from. But I'm actually realizing it came even earlier than that. Do you wanna tell our listeners like the OG summit idea we had?

This has been like 6 years in the making, Madison. Yes. No, the OG INSIDE Summit, I think when we first met in 2018 through a mutual friend who knew that we would hit it off, I think one of the things that was an early thread in our friendship was this desire to put together kind of community events. Make things happen and really have a lot of fun around sort of themes and ideas and industries that we were passionate about. So I was a product manager. You were a product manager. You were at Gap Inc. I was really interested in just like the retail ecosystem, even though I wasn't in retail, had done some fashion shows previously. And I think we kind of came together and said, hey, like there's this really incredible space in retail technology there's not a lot of community events happening around it. I'm sure there's plenty of people interested in our building in the space, but who are these people? How do we get to meet them? And so we decided we were going to throw Retail Tech Connect back in— what was this, 2019?

RTCS has a great ring to it, honestly.

We had like some jam sessions. We were getting a website together. We were thinking about locations. And honestly, I'm so glad We didn't do it then because I don't think we knew what we were getting ourselves into. But, you know, a turn of fate, 2020 came around. We just were really busy. We were like thinking about doing it, but we were trying to pick the right time and then the pandemic hit. So that kind of was put on pause for a little bit. But of course, we kept on noodling how we could continue to work together and do interesting things. I decided to start thinking about leaving Uber. You were now in venture, and instead of bringing people in the room together in person, we said, let's actually do it virtually and start, you know, really getting advice from other movers and shakers and founders that have built public companies and have backed these massive businesses and get advice from them. And I think that was really the thesis of The Room and how that got started.

No, it hasn't stopped being the thesis, and I think that like 6-year stat is crazy because when you look around at our gen, everyone is chronically online. We're all doing all these different things, and sometimes it does look like things happen overnight. But I was just struck sitting on stage with you last week and had this moment of like, wow, this was really an idea that we hatched over a free dinner at Uber's SF headquarters in 2018, and it took 6 years to realize that dream. And I think dreams sometimes can feel discouraging because is you have the idea and then, oh, a pandemic happens and it gets in the way. Oh, there's a global bank meltdown and that gets in the way. Things are always going to get in the way, but having a north star, having consistency, which the podcast was able to give us, and then growing a platform with a partner like you who always shows up for our shared vision, our shared dream, really, I think, were some of the salient learnings I felt as a builder through what the summit meant to us and of course what it meant for our community.

No, totally. And I think it's really just a testament to how a lot of times like things happen and you think it's taking you off course, but really the fact that we started the podcast during the pandemic, that went and started a business, that you had all this experience in venture, that all of these XYZ things happened is what made Inside Summit what it was, right? Like I think Inside Summit was. So much richer of an experience than what Retail Tech Connect could ever have been. And I think one of the things I really appreciated about Insight Summit was that there's so many events that I go to where it's like you're just there and vendors are trying to sell you and it's on this like very narrow topic and it's just, you know, this sort of like networking for the sake of networking. None of it's authentic. And I think one of the pieces of feedback I heard from Insight Summit that really resonated with me was that it It was genuinely just a day where there was truly something for everyone and people walked away with getting each other's phone numbers and setting up lunches and dinners to actually build friendships and see where those relationships could go, not just in a business sense, but also a social sense, which I thought was really cool.

Yeah. And I think that's how our generation wants to do work together, right? I mean, we're all side hustling, we're all out here trying to make things happen, and there's just this cultural shift happening, and I think this this is the DNA of the podcast, but also the summit, which is that conferences today are clearly not geared towards our generation who frankly has just different hospitality expectations and wants to connect in, like you said, that more slightly curated but also really authentic way. So, I know we've been jokingly calling this not your dad's technology conference, and I really think that's not a bad thing. It's time for this to be reinvented. We're in a post-COVID era. We're all digital natives. We're just going to, hey, want a barista bar with a matcha, but also to your point, want not to feel like suffocated in like back-to-back sessions slammed without like, you know, meaningful time to speak with people that we kind of think are cool.

No, totally. And so I think like, I think our listeners kind of understand our vibe and really like what we're trying to do and bringing together. This next gen of founders, tomorrow's IPO founders, the people that are funding those businesses, the people that are, you know, operating those businesses. Maybe for our listeners, Mads, do you want to talk a little bit about how we kind of came up with the programming and how we thought about structuring the day?

Okay, cool. So you guys know our style, right? We are technology, we are consumer, we are infrastructure. Really anyone that you think is fascinating and has built a billion-dollar business, We want to talk to them. And so for bringing together this day, we wanted to have that clash of culture, which we do feel like is authentically you and me and the way that we like to engage with people's founding stories. So we had a mix of both infrastructure panels on a next-gen, Gen AI, to D2C consumer panel, to next-gen social platforms, which has a consumer component, but also has a tech platform angle. And then we closed the day with one of our, like, we're not allowed to have favorites, but with one of our most fun guests, Kashish Gupta of Hightouch from about 4 seasons ago. He's since forth had another round. They've continued to scale Hightouch and that company is now worth $650 million. So it was just a range of authentic founders who are building alongside you. If you're listening to this and you're a builder, we were hearing from people in the trenches, but Kashish's a year from college. I mean, I don't think he likes to talk about that, but like, truly, like, he's so accomplished and has learned so much since he graduated from Penn in 2018. Like, that's the learnings we— the juju we want. So that was kind of the content that we were bringing to the table. I think also the fun stuff though was like the moments in between. Can you tell our listeners about like what was going on behind the panels that they're going to get to listen to shortly?

Yeah, no, excited to release the videos of the panels so you can just listen and not hear us talk about it and actually listen to the content. But yeah, I think it was important for us that it wasn't just a day where you go, you listen to a talk, you move on to the next talk. Like, we really wanted Summit to be super engaging and also provide value. Um, so one thing that we did was we had free headshots for everyone who came. When I first started Pryve, Alex and I were like, oh my God, we have no good photos of ourselves that look professional. Like, We need LinkedIn photos, we need pictures for our fundraising announcement, we need them for our pitch deck, you know, and, you know, we had to go find a photographer. It was super expensive. And, you know, our team wanted headshots too. And so we, yeah, we've spent a lot of money on headshots and it's just such an easy thing that really elevates, you know, the brand of a founder when they're fundraising that we could deliver, you know, on site. So that was one thing that we did. And then another piece, which was kind of a fun crossover moment for me with my customer base with Priv was really putting together consumer brand founders in a room by allowing them to showcase their products and have new shoppers discover their products. So we put together the D2C Brand Market, which was really a moment where all the attendees could go and literally shop these products, try, you know, Ollipop for the first time, try Unreal Snacks, you know, really engage with the brands that they're seeing on Instagram, on social all the time and realize how awesome the products are and understand the personality behind the brand. So it wasn't just like a free gift bag goodie moment, but really an opportunity for consumers to interface and build a bit of a relationship and community around like these next up-and-coming hot D2C stars. So that was really fun.

I love that we did that selfishly because I'm a snack girly myself. Also really cool to see all the hard work you've been doing with PRYV and having those brands get to join us in the room as well. And then of course, as you alluded to, some of our past guests like the Olipop founder from last season, upcoming on this season, the Unreal Snacks CEO. And I think what I liked the idea, of course, right? Who doesn't love snacks? But I think what I saw and observed in the room was this insight around experiential conferences that our generation expects out of, out of an activity. Right. And it's not just, oh, I'm picking up the snacks, I'm hungry. It's, oh, I get to shop it. And we have these totes and we get to maybe meet one of the brand founders who was there that day and like understand the energy behind why they're— we're doing better for you, Reese's Peanut Butter Cups. And, and I think like when you get to see these things in person after we were so stifled in the COVID era too, it just like brings this magic and brings this energy. So I think that was like a sleeper hit.

So hopefully we get to bring back to the market to next Inside Summit.

Yes, brands listening, if you want to be involved in really cool IRL experiences, hit us up. We're down.

Yeah. And I mean, I kind of just teased it there, but Claudia, do you think there's going to be a next Inside Summit?

I think obviously there has to be a next Inside Summit because people are asking for it. I mean, I think, you know, maybe I'm speaking for myself, but going into planning Inside Summit, I think we were kind of like, well, let's see what happens. You know, it's a bit of an experiment. Experiment as to whether there's real appetite for bridging kind of digital communities in real life in this way. And I was honestly just so humbled by all the conversations I had with the guests, the attendees saying, this was not like your tech conference. Like, this was actually fun. This was refreshing. I'm really inspired. When are you doing your next one? So I think maybe we'll do one in a different location, but I think, I think we gotta keep this train moving.

I hope we do too. And really, it was a huge thanks to Perkins Coie, Ramp, and Raise, who were our core sponsors who believed in us from the beginning with this vision around curating this space. Not only did their partnership help make it happen, but we were actually oversold for the event and had 120 people join us in the room. We were supposed to only have 100, but we made some exceptions at the last minute because we felt like we could do it. And I'm so glad we did. It felt like that perfect number of interesting, dynamic individuals. I think everyone in the room was truly under 35, if not under 40, which was just like insane. And every single person just had a story to tell and a story to learn from. So yeah, we'll be back. So look out for that. But let's take a step back from Inside Summit, which really is an extension of our platform with The Room Podcast. We are running into season 11 right down the corner.

I mean, I was floored when we hit double digits with 10, but the train keeps moving with season 11, and I think it's going to be probably our best season yet.

I literally just combined some insane, uh, turn of phrases there.

I don't know exactly what I was trying to say, but thank you for picking up on my analogy with the train.

For sure. I mean, weird turn of phrases is what we're in the business of, so you, you know, you knew where I was trying to go.

Yeah, no, and it is crazy. Like, season 10 was such a milestone for us. We kind of have teased this, but we're going to be launching all of those conversations I mentioned right now. So this is our recap, but next week we'll have the first conversation with KJ Sidbury of Google Ventures and his opening fireside chat about transitioning to becoming a partner at GV. And from there, you'll hear all the panels, all of the chats, and then this fall, Season 11 will be launching. But I think that as a part of our miniseries, for the Inside Summit recap, we're going to cross 100 episodes. Am I right?

I think you are right. We're going to cross 100 episodes. We need a separate event for that.

I know we're at 96 right now, and I'm just like counting down the days till we hit 100.

It's been a lot of fun hours in this virtual recording studio with you, Mads. I can't believe we're hitting 100.

Yeah, so, so, so much fun. And I'm really really grateful to get to be kind of at this stage of growth. Um, I guess like as we take a step back, like what would you say are some of the learnings we've had about podcasts? And you know, now that people are, you know, considering starting their own or thinking about their careers around podcasting, like yeah, what would have been some insights that come to mind for you?

Yeah, I think one which you touched on earlier, which is, you know, success doesn't happen overnight. Things don't happen overnight. You're not going to record 3 episodes and suddenly, you know, get a $60 million deal from Spotify. It just doesn't happen that way. Um, and so really being passionate about the content that you're putting out and being passionate about who you're doing it with is so important, right? I think this has been a testament to our friendship and just like committing to getting this done. Um, and we've learned and grown so much along the way. So I think just like consistency, commitment, and having a deeper reason for why you're wanting to, you know, speak on a podcast and put it together and what message you're bringing to your audience is important. And then I think the other thing is it doesn't have to just be a podcast. Like, what is the unique edge you are bringing with podcast being part of your platform? I think for us it's bringing together the entrepreneurial community in person and, you know, having these different ways in which we can kind of engage with this next generation of founder and funder. But, you know, maybe if you're doing a wellness podcast, it's by putting together wellness retreats or having some other version of community. And so I think a lot of people think of podcasts in such a narrow way. It really isn't. It's just a tool for you to achieve, you know, your mission. And however that happens, you can decide.

Yeah. Yeah, that's a great shout. And honestly, we're constantly evolving too, right? Like, you're going to see this miniseries is done with video because we're hearing that video is like the thing to do right now when it comes to podcasts. And so that, that's going to be a learning for us, like always having that growth mindset. I think like taking a step back from the Inside Summit itself and the learnings there. You're a full-time founder. I had always been an investor and you guys do so much work. The concept of asking someone to pay for our Inside Summit was a big step function for us. And I personally underestimated how much of a step function that would be. And I think you're chuckling at me because you're like, yeah, Madison, I know.

Grinding for years, and I know you have, and I'm a proud investor.

But I think as someone who just sometimes knows authentically, like, this is a great product, why wouldn't someone pay for it when then you're actually asking someone to put their credit card down again? Like, that was a learning for me.

And I want to just give a shout out to everyone who is trying to create revenue-generating businesses. Like, this is tough work. And if you are listening to this and you want to help us think about go-to-market and growth, like, we would love your advice.

I think that was the thing for me is like, you know, we put all this content out here. We had our Inside Summit landing page. It looked super snazzy. We got all these great content people who were going to tell their stories, and we hired an incredible event planning team, Kathleen O'Neill Productions. Like, truly everything was set up for success. And then when we put it online, there was like a week of crickets. And I was like, okay, if you build it, are they coming?

And so where I'm going with this maybe is, A, if you want to help us with go-to-market, the pod and events, come shout.

But also just sometimes having that conviction that magic is going to happen and getting in front of people is the harder part because everyone's time is such a valuable resource.

Increasingly so too. Like, there's just so much going on coming out of COVID Everyone's doing different things, going to events, AI, all these different tools and platforms people are paying for.

Just throw AI in there.

AI's happening. Yeah, it's tough. But I think, yeah, if you have a clear point of view, you'll figure out a way to kind of communicate that, that mission and that message. And I'm excited for us to continue doing that with Season 11 and the events that we're going to continue doing in 2024 and 2025.

Yeah, me too. I mean, me too. So, okay, look forward. Coming out is the miniseries which is surrounding Inside Summit content. You can expect 5 conversations. I mentioned KJ from GV, our conversation on next-gen Gen AI in collaboration with the Gen AI Collective. We had our conversation on the future of platforms with some really fun household favorite consumer social from from Belly, which many of you maybe are ranking your restaurants on, to Landing, which is next-gen Gen Z Pinterest, which is all moderated by Alex York, who is an associate editor at Forbes. We were lucky enough to be on her Forbes 30 Under 30 list for media this past year. So it was grateful to have her in the room and that synergy with the list. And then the panel that you led, Claudia.

Yes, the future of direct-to-consumer. So it was a fun conversation. Around what's coming next in the land of e-commerce. We spoke about community building, building a celebrity brand retention, how to engage with your customers. And so we had some unique perspectives. We had Nick Sharma, the CEO of Sharma Brands, one of the top DTC agencies, Scout Brisson, the CEO of De Soie, which is Katy Perry's nonalcoholic aperitif brand, talking from kind of the celebrity brand building perspective. We've had the head of digital product at Coterie, Marissa Steinmetz, who is a Priv customer. It was awesome to hear that shout out. And then we also had Brianna Tubner, who is a past podcast guest, the COO of TYB, a next-gen community rewards engagement platform. And so we just had a great conversation with so many different perspectives on what's next for consumer brands.

And then in case that wasn't enough, we had Kashish Gupta of Hightouch. I already teased that, which is a follow-up from our conversation in September of 2022. But he really read us in on what's new in reverse ETL, reverse extracts, transform, and load. The modern data stack, which he informed me kindly after the panel, is no longer called modern and is just data stack now. And also how that relates to the future of AI and how people are thinking about storing and using their data for really meaningful and impactful ways as we enter into this new era. And as, as we are entering into the new era, we're making sure that that's a continued conversation that we have on the podcast. So I'm pretty excited for season 11. One shout I want to make is the co-founder of Perplexity, which many of you maybe have used to help put together, you know, whether it be your notes after a meeting or research that you're doing. Honestly, I'm using Perplexity more than ChatGPT these days, so that's on that. And then on the CPG side, we're having some really fun founders around Unreal Snacks, Parachute Home. So if you're not already subscribed for season 11, I think you're going to want to.

Link below. Link. Amazing.

Okay. Well, I think with that we can wrap up. You can look out for the recap of the Inside Summit. Well, I guess the last thing I'll say is thank you for all of our listeners who've been so loyal to us from literally day zero. Send a podcast to one of your besties. Let them know you're thinking of them by sending them a conversation you might think they'd like. But truly, having you guys all in the room with us has meant the world to us. So Claudia and I couldn't thank you enough.

Couldn't be here without you guys. And excited for this community to keep growing and for both Madison and I to see you in person sometime soon.

Oh yeah. Look out for our newsletter, which always posts about our latest and greatest events. Definitely some coming this fall to a city near you.

Amazing. Well, let's get to it.