Season 2 Recap: Claudia & Madison
29 Apr 2021 · 34 min
In this episode of The Room, co‑hosts Claudia Laurie and Madison McIlwain provide a comprehensive wrap‑up of Season 2 while sharing personal career updates. Claudia explains her decision to leave Uber and launch her e‑commerce infrastructure startup Pryve, detailing the realities of fundraising during the pandemic and the importance of concise storytelling and relationship‑driven investing. Madison announces her promotion to partner at the early‑stage venture firm Defy, describing her new focus on seed‑stage founders, product‑market fit, and the relational nature of venture work. The hosts then review the nine (actually ten) Season 2 guests—spanning fintech (Fast, Open, Brex), media disruption (Jane Metcalfe), crypto (Zubin Koticha), consumer brands, and leadership transitions (Ajay Kaur of UrbanStems)—highlighting key themes such as frictionless checkout experiences, the value of strategic early‑stage investors over brand‑name funds, and the psychological challenges of founder‑CEO identity and leadership transitions. They critique the hero‑founder narrative and discuss when venture capital is appropriate versus alternative financing. The episode concludes with announcements for Season 3: new partners Silicon Valley Bank and law firm Cooley, a teaser for upcoming guest Sierra Wilson (music‑industry entrepreneur), and a brief look at podcast growth tactics, including a new marketing associate, SEO, and a call for listener reviews. Throughout, the conversation is informal, supportive, and aimed at providing actionable insights for founders and aspiring entrepreneurs.
Chapters
Come on into The Room. The Room is the series that lets you get a view into the room where it happened. If you're a founder facing questions about your first customer, first fundraise, or first hire, this is the show for you. I'm Claudia Laurie.
And I'm Madison McIlwain, your co-hosts. Hi, Claudia.
Hi, Madison. How's everything going?
Everything is great. It's a bit of an overcast day here in San Francisco, so I'm a little chilly, honestly.
And the past week has been very, very odd. So I'm very much looking forward to a proper spring very soon.
You would not know that I lived in rural New Hampshire for 4 years, given now if it dips below 50, I still break out a hat.
Same. I, based on my reaction to these days, I never lived in Boston or New York.
It's concerning how soft California makes you, but it's been a minute since we've chatted, just you and me. I wanted to touch on some life updates for both of us and give some listeners some exciting things that we've been up to personally outside of this podcast, as well as summarizing our thoughts and feels about season 2, and then some fun teasers and announcements looking forward to next season. How does that sound?
Perfect. There's a lot of goodness for us to share today.
Awesome.
Yours might be the biggest life update yet, so let's start with you. I know you made the big decision to leave Uber in January and actually started your very own company, Pryve. Share a little bit about that decision-making process and that transition for you.
Absolutely. It's definitely been a new year, new changes. It's in short been awesome starting Pryve and going off on my own entrepreneurial journey, I have to say that I think I started thinking about leaving my past company and starting something new in the middle of 2020. And a lot of it was inspired by hearing a lot of the startup stories and founding stories from the guests that we chatted to. I think I had a lot of preconceived notions of what the startup founding journey looks, and it was really reassuring to hear what the nitty-gritty details of what that journey actually is from a lot of our guests. But really, just to rewind a little bit, have always been really passionate about fashion and the retail space. I think a lot of people who know me know that, and also had really learned a lot at Uber in how to think about marketplaces and intelligence and pricing. And I decided midway that I really wanted to go off my own with my co-founder and start something in the e-commerce infrastructure space, In January, we closed our first round of funding. Madison is one of our investors, and so it's been awesome to have not only your friendship and co-host relationship here, but it's been really cool to also be able to work with you in the more day job capacity as you being an investor.
I know I have to start flagging our texts and say, okay, this is a live question. This is the room question.
This is a live question. Otherwise we have too many work streams going on.
We should have 3 separate group chats of just you and me.
I know, totally.
Well, it's been really cool to watch you go on this journey because I don't think it came to any surprise of a, a personal friend of yours that this was the path you took. I mean, you've always been entrepreneurial in spirit, having done a lot of stuff in high school even that we've talked about. What to you has been something that you've learned maybe for our listeners about yourself, about the experience that perhaps was un— was surprising or unsurprising, just given you have had a lot of exposure to the startup world?
Totally. I think fundraising was very different to what my expectations were, and especially fundraising in 2020. I had this vision that I would go to Sand Hill Road and have in-person coffee chats with all these different investors, and instead it was 7 back-to-back Zoom pitches a day. And I think I learned a lot throughout the process. I think if I look back at my first few pitches and then the last few pitches that I did, you evolve a lot. It's almost a job that you have to learn how to do, and once you have cracked how to do that job, it's actually really fun. But really figuring out how do you put together a mission in a few compelling words, how do you pitch a vision in a few sentences because you don't have a lot of time to catch investors up and attention spans are short, especially when you're their 20th pitch of the day. And I think a lot of it was around getting really crisp on storytelling as well as hitting the key one-word important notes that investors really care about. I think I could go off for hours and hours and explain what we're doing and why we're excited and why this is awesome, but you just don't have that time. And so it was really more of an exercise of how do you take all of these thoughts and plans and how do you distill it into 10 slides? And I think that's just so much more difficult than you think it is. I think a lot of the most successful pitches, and I think you see this all the time, are these very simple, almost, oh, that, that's it pitches. But really that is the most difficult part.
You're calling out this really interesting learning I had earlier this year when we had a positioning and messaging event for our portfolio, which was really focused on this. How do you tell your story both to investors as well as to potential customers. And I heard this statistic that our attention spans are now at 8 seconds, which is crazy that you have 8 seconds to really hone in on a point and explain to someone what is Priv, and you just lose someone so quickly because really I think technology has habituated us to change. And so hearing you say that, I think resonates with this number I have in my head that 8 seconds. That's what you have to convince someone. You have obviously 30 minutes on the pitch, but 8 seconds of captive interest.
And I think the other learning was really how personal fundraising was. And I think for founders who are looking to fundraise, DM me. I feel I have a book of tips and tricks that I learned after Pitch50, but I didn't think that it would be so relationship-based in an interesting way where there is a lot of due diligence. Everyone talks. The investment community is incredibly small and just to be emotionally prepared for not only one, how draining pitching for hours and hours a day is for weeks on end, because it's not just you pitch 5 people and then you all get them to invest, even though that would be wonderful. And maybe in some cases that does happen, but really at the pre-seed and for your first fundraise, it's a marathon and you really have to divorce your personal emotions from the process and understand that this is truly— it's— relationships are incredibly important, but people are going to at the same time invest in you because it's a business decision that makes sense to them. But it's also important to make sure you build a strong personal relationship with them because at the pre-seed stage, they're investing in your potential as a founder. So it's this interesting tension between it being this transactional business process, but it also being an incredibly personal relationship that you'll end up having with your investor for years and years to come.
What I'm hearing you say almost is the, the nos are not personal, but the yeses are personal.
I think that's a good way to distill it.
Interesting. I'm excited. Yeah, I'm excited for you to go on this journey. I mean, congratulations really first and foremost. I think watching you go through this as a friend and obviously as an investor, I've just been really impressed with how you've carried yourself, how you've handled yourself. And I know there's so much more to come, but it's really fun to get to be on this journey with you in multiple capacities. So big congrats.
Thank you. And I'm excited over the next season and seasons of The Room. We'll probably have some more opportunities for me to give my take and share some of my experiences as we have conversations with guests and, and other people. So definitely more, more to come there.
Me too. There's a lot more to come.
And it's not just me with a life and career update, but some incredibly exciting news from Madison's side of the table is that she was just promoted to partner. So tell us more about that.
I am so thrilled to get to have a new role within the firm at Defy. We are an early-stage venture firm in the Bay Area, as many of you know. We invest across pre-seed, seed, Series A, but this new role for me is really an opportunity to lean into our seed portfolio, both helping those founders figure and find that product-market fit, which is really, I think, what my background comes in, having been a product manager prior to this role, as well as that relationship side of the business that Claudia alluded to and really spoke to just now. The idea that at the seed stage, it is so much about the people and figuring out and helping them on that founder journey. Personally, I think the relationship-driven nature of the business is what really gets me excited. This role of helping our seed strategy, helping our seed investments grow into Series A and lifelong Silicon Valley companies is really exciting. And so I'm just grateful for the opportunity to do so.
It's, it's awesome. And it's also been cool being someone in your portfolio to see you do your job, but also how much you've grown over the past year. I'm really excited to see where your career in venture goes in the next year and the next 5 years.
Thanks, Clauds. Yeah, it's nice to have a friend on the inside now as well of our amazing portfolio and, and learn along the way. So yeah, I think I think taking a step back and looking at you and me, we're just one example of where female friendship can really open so many doors. And it doesn't have to be female friendship, it can be friendship across the board, but there's just so much power in investing in your friends and believing in your friends and being their biggest champion. I think having you be that for me and, and hopefully me for you has just been invaluable in these 3 years in San Francisco together. And I would encourage all of our listeners to think about their incredible friends who are doing cool things. How are you supporting them? How are you showing up for them? Not just at brunch on the weekends, but really in the work context as well, because I think that's what people do to help build great companies. And so looking at how you can be doing that in your own community is really powerful.
Definitely. And for our listeners, if any of you are thinking about a career in venture or thinking about starting something or are struggling with that early founding journey, definitely reach out to us. I think we would love to pay it forward and speak about our experiences a little bit more.
We don't have all the answers, but we have to pretend we do. So definitely DM us.
Totally. I feel one of the, just very much to your point, Madison, about friends and having more in-depth relationships than just light banter over brunch. One of my really close friends who has been one of my best friends since freshman year of college embarked on the fundraising and founder journey at the same time as me, and she has this group chat of these 15 incredible female founders and the amount of incredibly helpful tactical nuggets you get out of this group chat, as well as just being able to vent to a group of people who really have been there and are going through it, has been a lot more helpful and, and needed than I expected.
I think what you're talking about is the people who are in the room with you and in the room this season, we had some really cool people. I, Didn't think we could get cooler guests than season 1, but I'm gonna say we, we leveled up ourselves. We really showed ourselves we could.
And should we do a quick burn down of who we've had on this season? I'm looking at our list and we'll dig into what we've learned and some highlights and surprising nuggets from those episodes. But we've had such incredible founders, operators, investors from opening the season with Amy Chang of A Company to Ajay Kauri of UrbanStems, which by the way, I've used 4 times since our podcast recording. To Jane Metcalfe of Wired magazine and Cho Chocolates. Also, I have bought many Cho Chocolates since our episode. Jesse Draper of, of Halogen, which was such an incredible episode, and I'm so excited to have just had that conversation with her. A little bit more news to come later, but Jesse and I are now working together in a more professional context. So it's awesome how a podcast recording can often just turn into a pitch and something more. Then we also chatted with Sridhar Ramaswamy of Niva, Allison Barr Allen of Fast, Zubin Koticha of Open, our first crypto episode, which has been a fascinating space that has been heating up over the past few months. Liz Meyerdirk of the Pill Club, of course, and then one of Madison McIlwain's partners, Trey Vassallo of DeFi.
Wow, you really crushed those names, Claudia.
That's my biggest fear on this podcast is that I'm gonna butcher someone's name and it is gonna be really embarrassing. So well done.
Well, it's funny, sometimes when I record the episode intros, I have to coach myself through the name multiple, multiple times. I get through the whole thing perfectly and then butcher the name on the last second.
So, uh, brutal.
Well, I don't think we'll have to take a second take on those, but The 9 guests we had this season really fell across a lot of different sectors and areas of expertise. They all had different paths into entrepreneurship and leadership, but I'd love to touch on a couple different themes that we saw both across seasons as well as emerging themes in this season. And one of those first emerging themes was fintech or financial technology. We didn't have any fintech entrepreneurs in season 1, but in season 2 we had 3, which I think really speaks to The way that the world is leaning more into fintech. And so Fast, Open, and then our bonus episode with Brex were really 3 unique and different types of fintech solutions that are in some ways consumer-facing, in other ways B2B, but are changing the status quo on what it means to be a fintech company. So what, what did you think of those conversations?
I feel were really interesting how they could all be bucketed under the umbrella of fintech, and yet they're all solving incredibly different things in very different spaces. And so it really seems unlocking access to transactions, to payments, to credit in new interesting ways for different demographics was one of the connecting threads there. Let's start with Fast. I thought that was fascinating. It was awesome to chat with Allison, having seen her in the office back in the Uber days. She was working on the payments and money team at Uber, and so it made a ton of sense for her to go after the checkout space. But I think the checkout space is something that has been getting a lot of funding and attention, and it makes sense in 2020. If you are able to check out quickly, you're more likely to buy something. And then I think there's also a really interesting data play there. Madison, from your perspective as an investor, what are your thoughts on the checkout space? Specifically in the fintech world?
I'll start with sharing a personal anecdote, um, which totally reveals me and my terrible shopping habits. But just last week I was looking for bikinis for summer because swimsuit season is apparently back. But I was first looking at Revolve and was like, all of these swimsuits are $200. I don't understand why swimsuits are costing that much. This is ridiculous. It's fabric that goes gross. This is irrational purchase. So I was Googling and what's the best swimsuits this season and Abercrombie and Fitch kept coming up and I was okay, I don't know if I've shopped here since 2010, but I guess I'll go check it out. So I downloaded their app and I was just swiping and, and they had a lot of cute swimsuits. So I was okay, well maybe I'll order from Abercrombie. This is embarrassing. I'm never going to tell anyone. I can't believe I'm talking about it now, but I went to the checkout, went to the cart and it was pay right now with Apple Pay. And I was on my phone and I have Apple Pay installed and I bought it right then and there because it was so frictionless. It was just preloaded and I didn't want to leave my bed to go get my credit card. And so it was an amazing consumer experience. The aha moment of this was so seamless and this is such a delightful moment and I spent way more than I was planning on spending because I could just check out right there. From a retailer perspective is very powerful. And then from a consumer standpoint was so seamless, I would 10 out of 10 do it again. And so Back to your question, as an investor, those are the kinds of surprise and delight moments that we're looking for, for consumers that create real monetary incentive for brands in this case, or the stakeholder who's actually paying to have this service on their checkout flow. And so, yeah, I think as, as companies like Fast and others continue to innovate to make things checkout, which is a hassle for anyone, no one actually wants to do checkout, more simple and seamless, there's going to be a lot of value creation there.
Yeah, no, I completely agree. And it seems you made an incremental purchase because of the experience. And I think just zooming out a little bit away from payments specifically, but I think if we look at the e-commerce space overall, I think any infrastructure or any tool that drives a shopper towards incrementality, I think will continue to be interesting. I feel we've gotten past the phase of Okay, we have Shopify, we have Magento, we have WooCommerce, we have these platforms that are enabling businesses to emerge and, you know, get running. And I think now we're entering this interesting space of how do you get efficiency and also how do you grow. And so I think a lot of it is around loyalty programs, subscriptions, seamless checkout. And I think a lot of that is directed at driving incrementality, which, to bring it back to Uber, was everything we focused about and a little bit of a hint at what I'm going to be focusing on with my startup.
I was going to say, is this an ad for Pryve? Maybe, maybe it is. Here for that. Let's talk about your friend Zubin, who you've actually known since high school. So speaking of relationships, that's a long one. And he is another person who didn't surprise you that he was going to become a founder. And he had so many great insights on the future of DeFi, not my venture firm, the decentralized finance space and crypto. But one thing that really stuck out to me as an investor from his insights was the reason they chose Paradigm for their Series A, and Paradigm is a crypto-focused Series A early-stage venture fund. He had some great insights there. Maybe speak to your take on his exposure to why he picked them as an investor.
Yeah, absolutely. I think at the early stage, and my co-founder and I, we face this as well, it's really important to bring people on who just really get the mission and are able to bring a lot of specialized skill and focus to the table. I think it's very easy for people to want to go after those Hallmark venture fund names at an early, early stage, which is awesome and incredible if you can get them on board, but it might not necessarily be strategic. So even if you are able to get one of those big brand name firms, definitely consider getting someone on board who can be of significant strategic help, whether they are an awesome operator that has been in your space and is able to really help you with some low-level things such as thinking through a difficult problem or strategy, or just industry and built knowledge that you wouldn't be able to get from someone who hasn't deeply worked in that sector, all the way to having investors that are really in tuned with who your customers are going to be. And can give you that perspective. And oftentimes having people that will provide so much more value that by the time you go to raise your next round, the big brand investors will be incredibly excited and you've started to already hit product market fit. And so it seems from Zhu Bin's perspective, Paradigm and, and Matt Huang, the partner there, were incredibly valuable to him because they were at the forefront of crypto and where it was going for many, many years. That they were able to help him think through some significant technical challenges and recommend certain people for him to hire. And I think that's very much a testament to the fact that you want to make sure that everything you do at the early stage is value-additive, not just optics, even though that's all also incredibly important.
So the takeaway that I'm getting from this abstraction of Zubin's experience and your own is for first-time founders or founders in general who are raising these earlier rounds, let's call it pre-Series A or at Series A, maybe index on expertise and hands-on help rather than name brand recognition for a venture fund. Because today capital's cheap, right? I mean, I just read a report in the WSJ that the amount of investments made in, uh, Q1 of 2021 was 40% higher than the total number of investments made in venture capital at the previous high. So it was 40% higher than any other quarter ever. In total investments. So there's a lot of capital going around, but it's not about the money. Well, it is, it's helpful. It really can be about the people and how they get you to that growth. And so would you resonate with that as a founder? Definitely.
Huge plus one.
So we're talking about these experiences in fintech, which is a relatively newer industry, but we don't always talk about new categories. Sometimes we talk with old categories, and one that was on this season was media and media disruption. And in season 1, we had Jessica Lessin of The Information. Our guest this season, Jane Metcalfe of Wired, was an innovator when the whole technology industry was being disrupted and created a traditional media source, i.e., a magazine, but really focusing on the disruptive industry of technology.
I thought her episode was particularly interesting because she was talking about the first version of paid advertising and inventing promotional banners on websites. And these are things that we take for granted and couldn't really imagine how people message things and market things without things like that. But she had such a fascinating perspective of what the world looked before the internet and the stories that she was able to report on as the internet became mainstream, which is a wild statement to think about. And I have to think of her as almost an OG disruptor because she was just so passionate about what she was doing.
You could tell from the way that she spoke, the way that she was animated through our conversation, that she just had this big belief in knowledge sharing and the power of inspiration that comes from access to ideas and access to vision. And so it sounds what she's doing today with NeoLife, which is on the forefront of the biotech revolution, um, is another manifestation of her desire to be promoting and challenging and questioning all that is to come in another area of tech. We can talk about other sectors of overlap. Of course, there was more consumer consumer brands, cuz that's what we know and love. There was some more enterprise SaaS, but one theme that is not a sector theme, but rather a thread of leadership and leadership transitions came up in a couple episodes this season. I wanted to talk a little bit about the idea of when or why a CEO and co-founder might take a step back from their company. Ajay Kauri of UrbanStem shared a little bit about this experience for himself. What did you take away from, from his insights there?
Yeah, I think the skills and also just what you're interested in as an early-stage founder, zero to one, is very different for what it means on a day-to-day to be a CEO of a large corporation in its growth stage. I mean, I feel that definitely. I feel the things that make my day-to-day as a very early-stage founder successful are scrappiness and a lot of ideation on whiteboards and quickly getting things out the door and just selling people. That's very different than running an org of hundreds of thousands of people in some cases where a lot of it is around not getting an idea out and seeing if you can make people fall in love with it, but more optimizations on an existing business. It's been really fascinating to see the differences in founders we've chatted to from the early, early stage all the way to seasoned executives. I think if a founder does not want to be a CEO, that's not a bad thing. They should be doing what they're good at. And if what they're really passionate and good at is testing hypotheses and finding product-market fit, then it absolutely makes sense for them to bring in an external CEO to bring the company to the next level. Because at the end of the day, that initial founder just wants to see that business successful, and they probably also want to go after another space that they think can be disrupted.
But it sounds so hard. Claude, this is your baby, right? I feel this way about The Room. You feel this way about The Room and Priv. Just the emotional maturity it takes for some of these CEOs. And, and I really didn't feel that with Ajay and the way that he shared about why UrbanStems brought on Seth Goldman to become the new CEO when he transitioned to chairman was he knew exactly what you described as this need for an operational excellence CEO who could really scale UrbanStems nationwide and, and grow it, which as you alluded to earlier, they've absolutely done. It really impressed me with the grace that he brought to our conversation and his capacity to say what you said around, yeah, I'm a zero-to-one founder. I, I thrive in the nitty-gritty tactical figuring this out. And when it hits scale, it's someone else's job. It was inspiring for me to think about, wow, there is transitions and there is stages in a career as well as a business. So for all of our founders who are listening, if this is something you're thinking about going through, you've gone through, definitely listen to Ajay's episode.
I think it's definitely a topic that needs to be talked about more because I think a lot of businesses end up shuttering or end up going down a really bad path because that moment of transition and maturity is difficult.
And I think there's just a slight critique maybe of the way that we think about founders today, which is there's this heroism that comes in and as the founder you become the company and the company becomes you. Uh, and I think that's a really powerful way to grow a business, especially on the consumer side. The face of the business can be what helps excel the company. But a business and a person, it sounds silly to say, but they're very different, right? And so if, if you become your business and that's who you identify as, I just think it creates a really fragile psychological situation for a founder at the end of the day.
Especially when you're taking venture funding. I think that was another topic we touched on a little bit that, and we touched on it, um, in the Trey episode. That just because you wanna start a business does not mean that you need to take venture funding. It's a very specific business with a very specific growth projections that you would need for venture funding. And when you bring investors in, you're bringing a lot of different opinions to the table. And ultimately when you stand up a board, you can't be the only person with the decision, right? And I think a lot of people think that being venture-backed means that you're a better company. Or you've made it, and a lot of these different other connotations. However, I think a lot of people would actually be happier and the business could potentially be better if they didn't take venture funding.
It's definitely not talked about here, and I'm obviously biased. I think everyone should take venture capital. Just kidding. But venture capital is a great source of funding. But questions equity versus debt are fundamental to asking yourself, how am I going to grow this business? So you raise a really excellent point from another one of our amazing guests, and I mean, I would almost say I can't imagine how we're going to top it in season 3, but we have some exciting announcements around how season 3 is coming together in a short couple days. And so just want to say to all of our listeners, thank you so much for listening in to season 2 and these 9 amazing— no, 10, 10 amazing guests that we spoke to this past season. We hope that they inspired you, and if you had questions about the guests themselves or questions you would have preferred us to ask the guests or future guests you'd like to see, I mean, let us know. Hopefully we're accessible on Instagram, on our website and other channels, Twitter, Clubhouse. We're pretty all over the place, so you can probably find us. We'd love to hear from you. Absolutely.
Not only do we have incredibly exciting guests for season 3, but we have some pretty awesome partners. Madison, do you wanna tell our listeners a little bit more about our partners through season 3?
Yeah, absolutely. As we continue to grow and think about how we're sharing the room to you, we've brought on two incredible partners who are gonna help us do that. We have Silicon Valley Bank and Cooley, who is a law firm here in the Bay Area. And the reason we thought about these two specific partners is because they have been in the middle, in the heart of technology and entrepreneurship for, I think, the past 50 years, but maybe even more than that. I mean, they're just stalwarts in the industry and have helped hundreds of thousands of founders probably get started both in banking and in these kind of opaque law terms that you need. You can Google, you can look up on Investopedia, but we really think sometimes just talking to someone is the best way to get your answers. And so we're really excited to be bringing them in as partners and sponsors for the upcoming season to hopefully create more access to your questions around how to find banking, how to, how to start your first bank account, or how do you, uh, get your legal documents signed to finalize your first fundraise. So we're pretty stoked to have them coming on. Claudia, what would you add?
Yeah, I would just say that as someone who has recently closed a round of funding, your banking relationships and also your legal team for going through that whole process is so critical. I, I also thought, oh, I could probably Google it and maybe we can draft some forms. This should be pretty straightforward. Really depending on the type of financing that you have, it's, it's not. And there's, you know, so many negotiations and different components that you have to put together. And I think having someone that you can trust and has seen all of the edge cases before is incredibly important. So I'm really excited for us to have some real talk conversations with some of our partners this season to help shed light on what a lot of those questions and processes actually look ask for all of you.
As Claudia and I are thinking of growing and hoping to continue growing The Room, turns out there's some things that actually matter in growing a podcast. People don't just ask you to subscribe and write a review because they—
the nice words actually really matters for our search engine optimization and helps us get found on the Apple Podcast Store. So I'm gonna say what I never thought I would say because we don't wanna be those podcasters, but please subscribe and write us a review.
5 stars, please.
5 stars. We won't take anything less. And if you give us less, DM us first and we can talk it through.
We would love to add one other way we've grown this past season is we added our amazing marketing associate, Aurelia Han, who is taking a year off Harvard to just be a big kid in the real world, but also because he wants to be at Zoom University. And so she has been helping us. You may have noticed that we really leveled up a lot of our graphics. Our content, our blog posts. So, welcome, Aurelie. She's not joining us in the conversations, but she's behind the scenes and is a wonder woman. So, thank you for all that she does.
Absolutely. Huge addition to the team. And Madison, we also have a really exciting guest who is going to be opening season 3 for us. And I don't wanna spoil anything, but do you wanna give a hint to our listeners?
I don't wanna spoil anything either, but I think we're just a couple days away, so I think the cat's out of the bag. We can share that Sierra, no last name needed, but also known as Sierra Wilson, is joining us in the room to share about her experience being a young woman in the music industry and the lessons she learned there and how she's grown into her own businesswoman and founder and entrepreneur, both as the creator of her own music production company, Beauty Marks Entertainment, co-founder of a fashion house, the House of Love, Respect, and Care, with her life partner Russell Wilson, and so many other amazing things that she's doing to make our world a better place. I mean, I walked away from that conversation absolutely inspired. Claudia?
Same. I was floored. I was on a high for the rest of the day. So if you don't listen to any other episodes for season 3, definitely listen to this here.
We talk about leveling up yourself and your career, how you only need one person to believe in you, and that person's you, and I just really took that to heart. And so definitely tune in next Tuesday to our launch of season 3 with our amazing partners, SVB and Cooley, and learn about Ciara's incredible career, both as a music sensation, Grammy Award-winning, as well as an entrepreneur and a mom. Uh, I don't know how she does it, but she's thriving and, uh, it's gonna be such a treat to have her in the room with you all. So thank you for listening to our season 2 recap, and we're looking forward to all the fun ahead in season 3.
Absolutely. It's been fun catching up, Madison, and talk to you later. Yeah, I'll talk to you later.
All opinions expressed by Claudia and Madison and podcast guests are solely their own opinions and do not reflect the opinion of The5AC. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
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S15E1: Building the Infrastructure for Voice AI with Russ d'Sa, Co-Founder and CEO of LiveKit


Building an Enterprise VC Firm with Jai Das, President and Co-Founder of Sapphire Ventures | Founding the Fund 4


Turning Content into Competitive Advantage with Packy McCormick | Founding the Fund 3
Backing Technical Founders with Amplify Partners Founder Sunil Dhaliwal | Founding the Fund 2
Investing in Trillion-Dollar Outcomes with Ben Ling of Bling Capital | Founding the Fund 1
S14E8: From a Shark Tank No to Billion-Dollar Exit with Ring Inventor, Jamie Siminoff
S14E7: Building the AI Layer for Legal Work with Scott Stevenson, Co-Founder and CEO of Spellbook
S13E6: How Almost Friday Media is Shaping the Next Era of Entertainment with Jack Barrett