The Marketing Bestie Podcast with zoeunlimited - how a man HACKED fashion ($7.4 billion Poshmark)

Episode Date: September 28, 2025

How Manish Chandra (Founder & CEO of Poshmark) went from tech geek to fashion royalty💡FREE 7-day branding course + (🎁)challenge: Early Bonus Access👉🏻 https://tapx.it/unlimitedyou-early5 years of social media and marketing knowledge Thank you Stan (as seen on Diary of the CEO) for funding production✨Manish's socialsLinkedIn https://www.linkedin.com/in/manishchandra1/Instagram https://www.instagram.com/marrc/Poshmark https://www.instagram.com/poshmark/✍🏻FREE EMAIL LIST https://tapx.it/stanzoeunlimitedLearn & Grow with me.💖 Instagram: https://tapthe.link/zoeunlimitedig💜 TikTok: https://tapthe.link/zoeunlimitedtiktok🖤 Listen on Apple & Spotify: https://tapthe.link/zoeunlimitedapple https://tapthe.link/zoeunlimitedspotify🪭 All my outfits https://tapthe.link/zoeunlimitedltk👩🏻‍💻 LinkedIn https://tapthe.link/zoeunlimitedlinkedin🛒 Amazon Essentials https://tapthe.link/zoeunlimited👉use code ZOEUNLIMITED for 10% off ALL travels on Klook https://t.ly/aA76T📸My gear: (Sony A7Siii) [ZOEUNLIMITED15] https://tapx.it/lensrental 📧 Business inquiries: [e-mail] //🕙Timestamps: 0:00 Intro//👗LOOKBOOK Revolve outfits: https://tapthe.link/zoeunlimitedrevolveAll my outfits https://tapthe.link/zoeunlimitedltkCream White Wide-Leg Dress Pants (M) https://tapthe.link/Pgvysbk5oVitaly gold collar https://sovrn.co/7wtgp38Athena ring https://bit.ly/3G54y1y👉use code ZOEUNLIMITED10 for 10% off on YesStyle//😋Fav proteins-BEST chocolate protein https://tapthe.link/huelzoeunlimitedget $15 off your entire order ZOEUNLIMITED- chocolate collagen protein: [code ZOEUNLIMITED20] https://tapthe.link/T-LEclSOa- tastiest bars https://bit.ly/3OpQoN8- 😋try my fav mango chili lollipop and horchata electrolyte https://tapx.it/tastesaludzoe10 🥭🩵 get 10% off with ZOE10 //💪🏻MY WORKOUTS11 abs routine https://youtu.be/D-8kLwf8xjcSlim legs routine https://youtu.be/Dd3Nbh7OXUUKpop idol arms routine https://youtu.be/6QlEAzstdI4//💦FITNESS -Resistance band: https://amzn.to/3w2k3o3-Current yoga mat: https://amzn.to/3CICqjf//✨Fav skincareFav skincare: https://amzn.to/40ciLWzToner https://shrsl.com/3st55Water sleeping mask https://shrsl.com/3st5jLip mask https://shrsl.com/3st5kDr Jart Vitamin mask https://shrsl.com/420l8Dr Jart hydration mask https://shrsl.com/4fl7n//📸 Camera: https://tapthe.link/wp8Yr0GlC//📕MY CPA EBOOK https://tapthe.link/zoeunlimitedcpabook//📚RECOMMENDED BOOKS1) This Is Marketing https://amzn.to/3ArHk7N2) Purple Cow: Transform Your Business by Being Remarkable https://amzn.to/3CnlF133) Atomic Habits by James Clear: https://amzn.to/359KZUk4)The Power of Habit: Why We Do What We Do in Life and Business: https://amzn.to/2BUJwGC5) The Subtle Art of Not Giving a F*ck https://amzn.to/2VtNqQm//🎵 MUSIC Get FREE royalty-free music https://tapx.it/thematiczoeunlimitedIOSUB - Dreams - https://thmatc.co/?l=F1D5E3FESub count at upload:

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Manish Chandra built Palsh Mark in his garage without any following. Three enterprise people, all guys trying to do this shopping website. How were you able to tap into the psychology of this female demographic? If there were a last person to be the face of fashion, it must be Manish Chandra, Born not into the fashion scene, but a town in India, built his career in software, and spent decades behind the scenes coding databases and enterprise tools,

no runway access, no aesthetic Tumblr era, and not even a Pinterest board. But somehow, at 43, he began building the empire of closets. Age itself is not a factor. It's a factor. Manish didn't follow fashion, he reprogrammed it into Poshmark. With over 80 million users,

people were making over six or seven figures by selling fashion pieces with everyone from Ashton Couture, Rachel Zoe, Serena Williams, Doja Cat. Welcome to the Marketing Bestie Podcast, where we dive into branding, business, and creative strategy with the smartest founders, CMOs, and culture shapers to help you and your business unlock your unlimited potential. All resources are linked below. And I remember just walking there at five or six in the night, just crying because I didn't know what to do at that point. This is truly a masterclass in how to build a brand as a quote-unquote outsider how to tap into your intuition and early opportunities and what it takes to scale a business

to the billions you can be misunderstood for a long time poshmark could not have been built without the power of social and mobile having a personal brand is literally a cheat code to business and i want you to have it you asked i deliver i made a free seven day step-by-step guide on how to build your dream life with social media not just going viral but actually monetizing and and getting closer to financial freedom. For me, it helped me quit the job I hated, get paid to do what I love, to learn and grow with you. And speak to Olivier Rodrigo and Fortune 500 leaders,

all on my own time. You just need to sign up for the early access list in the description to get special early access. Plus, bonus is worth hundreds of dollars only if you're on the list. So huge shout out to Stan Store for funding this challenge so everything can be free. It is the same Stan Store you heard Stephen Bartlett, the diary of the CEO talk about, where creators aren't anywhere from tens of thousands to millions. I'll show you how inside the challenge. You don't need to sign up for Stan to join the early

access list, but if you're entrepreneurial, check out their free trial. You'll be ahead of the curve when the guy drops. You're actually one of the first ever male guest on the show. Wow. So very honored to have you here. I'm very honored to be here. I'm super excited. Manish, what are some early contexts of you outside, side of all your impressive stats that the audience should know about you. You founded a fashion retail company called Poshmark that at one point was humbly valued at $7.4 billion. It was acquired at $1.2 billion with over 80 million active users, including Serena Williams and Doge Cat. But you did not come from a fashion background. In fact,

you didn't even grow up in the U.S. You moved to the U.S. when you were 19. And as, at 19 years old. What was your experience with fashion or entrepreneurship? I didn't feel an entrepreneur at that time, but, you know, in hindsight, you can see that I did some things that were entrepreneurial. I'll talk about that in a second. But I came here thinking, my vision of entering U.S. was more New York. This is, if you can go back into the 80s, there was not a lot of content. There was no social media. Correct. You know, so everything was done through books. So I had kind of this visualization. Books, not even television. Some movies, but not like a lot of content was there, especially in India.

And so I had this vision of reading Iron Rands Fountainhead and Atlas shrugged. And from there, everything was New York. But I instead landed in Dallas and Austin, which was even flatter than you can imagine today. And so it was kind of a little bit of a surprise to me that America looks like that, you know, not knowing how diverse America is. And so it was kind of a very different kind of a arrival. here. But I loved it. You know, it was so fun. There was so much to discover. I came here in 87. At that time, music in Austin was a big thing. And I love music. It was an incredible time where I was able to go walk into and just listen to a great artist called Tracy Chapman. And I was just standing right in front

that she was performing on the stage. It was very informal kind of like stuff where, you know, you could still buy tickets for like $5 or some crazy number. I don't, because I was a student. I couldn't afford more than that. So it was a fun time. That was fun. I understand the small culture shock where you expect everywhere to be New York. For me, it was like gossip girl. It should look like that. And then everywhere else was like flat and blocks of strip malls and things like that. Very interesting. But you did not study fashion. You were an engineer. Study computer science, right? Yeah. So my degree was in computer science and my projects were all in database. And at that time, AI, which is like very old AI.

Really? Less programming and stuff. But I was doing like more databases and database software at that time. I was enrolled for a PhD program. But after two years of doing my master's, I, U.T. Austin had the option to finish up with masters and actually just take a degree and leave. So that's what I did. I ended up finishing my master's and moving to Silicon Valley in 89.

I know you started Intel right after, but what was your goal and ambition at the that time. And did you want to pursue anything fashion-related? No, not at all. I was actually wanting to work for building database software. I wanted to make some money. You know, I spent two years studying. And I wanted to be in Silicon Valley. I didn't even know what that was, you know, but it was like somewhere in California. So those were the three goals I had. And that's it. Like, I didn't have any other major ambition besides just being able to get a job, do some cool coding, and get a paycheck. I love how pure it is. You enjoy building things and you just want to live a sustainable life where you can provide for yourself.

I think the simplicity of desire is pretty helpful. I feel like in some ways with all of the information available to this generation, there's too much information available. When I was at Intel, I'd been there for a year. And they had moved from building databases internally because it was a semiconductor chip company, you know, fast growing to buying commercial database. And I said, I don't want to work on deploying commercial. commercial databases, I want to be inside the heart at the software level. So I interviewed with a few

companies and got a job at a company called Sybase. At that time, it would take like a few months to transfer your H1 from one company to the other. So as I was waiting for those few months, unknown to me, Silicon Valley hit its first recession that I was, you know, alive to, but I didn't know. I was just there. So when my H1 came, the recruiter called me and said, Mnishir, H1 has been approved. But I want to tell you that we're going through. layoffs and the company is, you know, not doing well, but we are going through layoffs. I'm going to lay off a certain number of people. And I was so set on joining this company. It was the best technical company. It was in Berkeley. I used to have a ponytail at that time. So I was like all these sort of I wanted to be in Berkeley.

Really? And so it was like this strong desire. I asked her, I said, you know, is my job still there? She goes, yes, you have a job. It was an entry-level job. Is my salary still the same? The salary is still the same. I said, I'm taking it. And I moved. And the very first. Friday, we used to have Friday beer bus. The CEO came and he talked about the fact that, you know, we have not been successful in raising capital. We're operating on debt and we're trying very hard to raise capital. I didn't understand anything. There was some guitar playing. Engineers were playing guitar. You know, I was like having some beer and I was just like learning from a fire hose. Right. And I think being a little naive helped me in making the decision to join his company.

What ended up happening was that recession was a fast-poly recession. It lasted. for about a year and a half. Okay. And the company had pulled the plugs on an IPO. Company was small, I think, 70, 80 people. And in the next five years that was there, we grew to 6,000 people. It became a public company. The little bit of stock they gave me, allowed me to buy my first house.

I met my wife when I was there. Oh, really? Not at the company, but like at that phase in my life because being in Berkeley, S.F. It just turned out to be one of the best decisions I made. Wow, I love that. Sometimes you have to not overthink things and just like follow it, go through the actions. But I'm also wondering, did it plant a seed in you where you got to see the risk as an employee where it's like, oh, this could be taken away from me any single moment. And in order to

build something sustainable, I need to have equity in something and have more of the upside and also take on more risk as a owner. Not really. What it did build in me was joining things smaller. So I went from that company to joining an 8% company. then joining a three, four-person company kind of a thing, and then starting my own company. So it kind of became smaller. I actually was a reluctant entrepreneur. I was not like, oh, man, I need to start something. I'm like geared up for that.

I was entrepreneur, but not like entrepreneur. So for a long time, at Sybase, I grew, you know, and when I was leaving Sybase, I was interviewing with some, quote, unquote, startups that were smaller, joined a startup which had about eight or ten people. He just finished my MBA at that time. but they still wanted to hire me as an engineer. And I wanted to work in marketing and product. And they were like, no, we don't have a job for you, but you can hire you as an engineer.

And, you know, obviously at a startup, you're not going to give me a chance to learn something new. You want me to do something I already know. So I took the chance. And the thing was the company needed people in product and marketing. So I was transferred there very quickly. And that company was such a great experience. You know, I was just lucky enough to choose good companies. And we went public.

There I was a senior executive. By the time we get public, I was running product for them. And then a year or so late, I was running all of product and all of marketing. And then we went through the full dot com sort of boom and down. And then I left them in 2001. Now, what was interesting at that time was when I left them, things were starting to cool down, but things were not bad. I resigned on September 1, 2001. 11 days later, 9-11 happened. And that tragedy, was pretty significant to the American economy and everything sort of smashed to the ground. So literally, even though the jobs in Silicon Valley were slowing down, after 9-11, there were no jobs. In fact, you could drive down 101 in Silicon Valley and it was see-through buildings. It reminded me the next. Okay. When I sell my business, I want the best tax and investment advice. I want to help my kids and I want to give back to the community.

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Play. Post. Taste. View. And enjoy. Via Rail, love the way. The time I saw that was actually during COVID. When there was no traffic on one-on-one, you could go from one point to the other, like, fast. So it was a very sad time. And that was a time I had to improvise to survive.

Because you just left 10 days earlier. Yeah. Wow. I'm also curious, before we jump into when you took that leap of faith into entrepreneurship, what was your thought process in taking an MBA and you had a very intentional pivot? to business and marketing at the time when you were already building a successful foundation in engineering.

That's kind of interesting. I would say I didn't have the money to go to a full-time MBA. And so I went to Haas, UC Berkeley. And at that time, the MBA program there was incredibly good value for a citizen, for a state resident. And I think my MBA on an annual basis

cost me less than $10,000, maybe less. And my company was willing to pay for it. That's amazing. Because it was a small amount, right? But the second thing was I really got a taste of business because at that company, I got exposed to the sales process, the marketing process. And I was partnering actively with these folks and being sent to conferences and stuff. So I really wanted to learn about business. And so those two things ended up being the reason I did my MBA.

You know, doing a part-time MBA while full-time working was not easy. But it was definitely rewarding. I mean, for me, a lot of light bulbs that went on in my head and kind of started, I think, In some ways, it was a pivotal journey to learning about even being an entrepreneur or a business person from being basically a very strong engineer. So here you were with this full-time job in engineering, you were in a relationship and you were balancing an MBA. I was married at that time because I'm just trying to think through. Yes, yes, we have gotten married, yes.

We were balancing marriage, job, and a pretty intensive, like it was a three-and-a-half, four-year program. Wow. It really shows when you're hungry to learn you're willing to make it happen no matter what. I think given your audience, I was in my 20s at that time. So you do also have incredible energy at that time, right? As you guys are. You can do a lot of things and not like me like now

where maybe the strip is already making me like, oh. No, I feel that sometimes. I'm like, am I old now? But I love it. After 9-11 happened and you just quit your role as VP of marketing, right? Yeah. So what happened at that time was there were still job interviews and offers coming in my direction.

But a lot of these companies, you know, they would make an offer and then they would disappear the next day because it was a really tough time. And so I decided to what now we call fractional consulting. I would call it timeshare or in the cloud. So basically I became the chief product officer and chief marketing officer kind of a role for many companies. And I was like doing this fractional kind of a role. Interesting. What I realized is I had two young kids. I had a mortgage and then I had sort of this thing where I was trying to think through what I want to do.

And through that process, I met a dozen or so companies and ended up partnering with about seven to eight CEOs, helping them a little bit, you know, a day at a time, a half a day at a time, et cetera. And soon one of the COOs who had worked with in the past said, Manish, why don't you help us look for a small company to acquire? And so I signed what I would call an investment banking agreement with this CEO and ended up finding a company and merged them. And then he invited me to be the chief marketing officer. And that's how my next job was. I literally created a job by finding two companies, merging them together and then joining them as the CMO.

So it was kind of an interesting journey for the next job. That's so interesting. And how was that role of being the CMO of this new company that you created? That was a tough one because somehow through the journey, the CEO ended up getting pushed out. And the CEO was decent, but it was like thing. And so what I realized through that process is that even though I'm helping all these different companies and doing all of these things, not being the CEO kind of puts me in this disadvantaged position where everything changes.

And then I have to kind of fix things and rebuilding. But CEO, I don't hold the cards. Even though I'm the architect of the deal and everything, I'm not the CEO. So I said, for the next company, I want to really. create it from scratch. You know, there were certain cultural things I didn't like about the company that I wanted to sort of take, but I wanted to be that. Fortunately or unfortunately, the idea that came to me was a consumer idea.

And I'd spent my entire career till that point in time, which was over a decade, in deep technical enterprise software, selling in the heart and guts of IT departments, you know, databases, object databases, relational databases, real-time databases. and this idea was a consumer home remodeling idea. And so I kept saying, you know, no, let me think of a different idea. How did it come up? It came up because we were remodeling our home. So it was basically the idea was what you would call a modern-day Pinterest,

you know, idea boards, social sharing. Nothing was like sort of simple at that time in 2003, 2004. So it was really painful. Like we would have to print out and then share the printouts. And then there were a bunch of people collaborating. you'd forget where the thing was, then you have to go back. You know, stuff that we don't even think about. This is pre-mobile, right?

It's all web. And so, sounds like I need to create this software. We can put these ideas, collect them in a list or a page, and just everyone can get on the same page and talk about it. And I just, I was like, who am I to do it? So I kept thinking, I'm not going to do it. For six months, I kept resisting it. You know, kept resisting it.

Really? Okay. Because I was like, let me think of something else. But a good idea and a good passion, it turned into, like, madness. You know, I looked at any problem and I felt like I could solve it with the software. I could solve world hunger. Then I was like, what do I do? Because I was so, like, challenged. And I was self-aware that this is a hard thing to do.

Right. And so I sat around, got some advice from my, you know, folks. And I started to create a small group that would meet every weekend at our home to brainstorm on the idea. Ah. And we call it the kitchen sink cabinet because, you know, gather around the kitchen. saying so what I would do during the week, I was still working my full-time job, was meet up with people and try to recruit them, recruit them to just come to this weekend meeting, right? And my pitch to you, if I met you, I'd say, so you come to my weekend

meeting, here's sort of high level of what the idea I'm talking about. If you want to come, you know, we'll sign a mutual sort of agreement that you can come and be participative in this thing. Your only commitment is show up. I'll give you hot Indian chai. And my wife, Asha would make some hot Indian snacks. That would be your incentive and you get to meet some interesting people. And soon that group organically grew to about eight or nine people. And we had coders in it. We had design people in it.

We had consumer people in it. And we started to create the product. So cool. Everyone was there because of a common interest and a passion for creating something that doesn't exist yet. And they were all energized because they liked the idea, etc. After a year of doing it, we were still working full-time job, etc. A bunch of people were there. We decided that, okay, now.

it's time. We feel like the idea is good, you know, et cetera. And I was more cautious because I didn't have the right instincts in consumer. I said, let's come. We'll have a big demo. You know, we're going to put all these things together. It was a little bit of like extraction of information. There was like technology. There was consumer UI, et cetera. We were able to do all of that, create a basic working prototype. And let's meet together and look at this prototype together. So like about nine or ten people gathered at my house and we called up to the prototype. It was working. And we said, okay, it was around end of December. we said, let's all go home and think about, do we want to quit our jobs and jump into it?

And the way we approached it is, I said, most people had kids at that time. And so people had to kind of take the risk of doing it. I did, I did as well. And I said, we're going to all think about it. And we will come back and decide who wants to jump in. And I said, you know, there's like three options. Either you don't jump in, in which case will create small advisory equity and say goodbye to you. Okay.

If you jump in full time now, quit your job. then you get a co-founder level status or a co-founding engineer level status, depending on you are. Or you just decide to walk away, you know, completely. And I said, even though I've put this whole team together, I have to think through, am I ready for this? Right? I had to talk to my family. Luckily, for some reason, we were going to my cousin's wedding, the theme of this podcast. And my mother was flying from India.

And so I got a chance to meet with her. And she encouraged me at that time to jump into this. She said, it's your passion. You should do it. So I came back. I said, I'm ready. I looked around. I thought maybe one technical person and one consumer DNA person would jump in.

All the consumer people said, no, no, it's too risky an idea. They left away. And so two of my enterprise friends wanted to jump in. So there were three enterprise people, all guys, trying to do this shopping website. And we were foolhard enough again to jump into it. We just said, you know, we're going to reserve some equity because we still need this consumer DNA. And that's how we start the journey. Wow.

Wow, wow. And that became... That became my first company. Caboodle, which in 2007 was acquired by Hearst Media and then became part of Hearst Media. Yeah. Think of Caboodle as kind of like a precursor to Pinterest. You would, you know, clip things.

You would be able to put them on the same page and people could leave comments, collaborate, et cetera. And we created a pre-active community, a few hundred thousand active members, a couple of million registered members. And that journey allowed me to go from business to business enterprise software guide to a tide-eyed consumer. and Kaboodle ended up starting in the home space but became mostly about fashion. Interesting.

You know, we did a lot of partnerships with Marie Claire, you know, a lot of sort of the big media, it was advertising based. Most of the content was fashion related. Very little was sort of home related. It kind of gave me the proverbial 10,000 hours in fashion. And I realized fashion had a lot of unsolved things that we could look at, a lot of things going on. So that, I would say, was sort of my journey into consumer, into fashion. into tech, passion tech. At the time, we coined the term social shopping. This is 2006. Oh,

that early. People used to ask me, like, what is social shopping? How can shopping be social? I go to the internet. I do comparison of, you know, SLR 1 and SLR 2, and I shop. And I realized that most of the people I was talking to were men. And we were building the product predominantly for women at that time. Right. Do you still get times where you feel lonely and not understood in your journey? Yes, for sure. But less so now, because I think I'm more at peace with myself and it's probably just more a factor of age than anything else. Even building Pashmart, there were times where I felt completely like I didn't know what to do because of just the circumstances they were.

I couldn't talk to anybody because the wisdom I knew, but I couldn't accept it. So I remember one time just walking around, you know, we had this office which was an office and there was like a little walkway around it where the parking lot was. And I remember just walking there at five or six in the night, just crying because I didn't know what to do at that point in time. but things were just, it was just like a crazy time. It was kind of like one of those times that so many good things were happening, but so many crazy bad things were happening.

It was different pressures, personal and professional. Right. That were going on. Those moments happened, right? And you just have to sometimes, you don't plow through them. Yeah. But they are challenging. Thank you for sharing.

Was it also hard to kind of show that vulnerable side to your family, especially to your wife and children? To anybody, right? Because everyone was counting on me at that minute. That's so rough. Because you have to kind of uplift the morale, while you know behind the scenes so much chaos is going on. Yes, on all fronts, yeah.

There was a moment of like tremendous pressure from various points in time, but there was not a good solution at that time. And then solutions did emerge in the next few weeks, you know. At that minute, it felt like, my God, you know, what am I going to do? If there was a friend at that time who could have showed up for you, in what ways would you like that friend to show up for you? I think to remind yourself that you have the strength to overcome this moment and to move yourself and your journey into a really positive place,

you have that strength. But sometimes we forget that we have that strength in us. That is so true. We forget that we have the light in us. Time and time again. At every stage. Absolutely. So that's how my journey started.

Fascinating how social shopping started as early as 2006. I would love to chat more about current day and also like the future of fashion, but like AI and tech as well. I feel like social shopping is a few. future where nobody's buying a thing just on a standalone basis. They buy it because the community is saying this is good. Today, I would say, you know, live shopping and all of that is quite a bit of social stuff happening today. I think so. The algorithm or the social atmosphere knows what you want

before you even know it. Yes. And creators. Social is everywhere. It's just different forms of social. Very much true. Was Caboodo profiting at the time or like how was the early stage and the growth stage of Cabo? Caboodle never became profitable. when I was there. I think eventually it might have, but when I was there, no, it was very early. We were only three or four years into building the company. And you boost-jraft the whole thing? Well, no, we raised capital, but small amounts of capital. More like pre-seat kind of capital.

Gotcha. It was early. We got acquired two years after founding the company, two and a half years. So it was very fast. What was the decision process? It was early. It was kind of complicated. We had a term sheet, I think, we had a term sheet from SoftBank, actually, at that time,

and we had this offer from Hearst. And we had a couple other choices. It was bored. It was the specific timeline. It was different things happening. You know, if I were to revisit that time frame back again, it's hard to know all of the factors that went into it. Just to give you a little bit of a sense, nine or ten months before we decided to sell the company, we'd gone through almost a near-death experience. Where we literally almost ran out of money.

Like I had to go drive around Silicon Valley, collect small checks to make the next payroll. That is so real. I think that's how real it gets. Yes, it was super real. It was like really stressful because I suddenly realized that it's just going to happen. It was almost like kind of a begging exercise to go to the investors and collect 10, 20 grand checks. It's so hard too. It's kind of like an ego death as well where you were betting a lot of your hopes and dreams on this creation. And now you have to overcome that and be like, actually, I need some help. I need some funding. Yes. The funny thing or sort of not the funny thing, but like kind of the high.

and lows of entrepreneurship are such that this happened, and then four months later, we had a pretty solid term sheet from SoftBang, which we ended up saying no to, and we ended up taking a letter of intent from Hearst. All of this happened in six months. So, you know, when they say the darkest days and the lightest days in entrepreneurship happen this quickly, this was all within six-month period. Wow. What pulled you through the six months when you didn't even see the light yet? I don't know if anything pulled me through. I definitely was going. Crazy, crazy. But, you know, on a different note, I do think that power of intention, you know, which is sometimes overused as power of manifestation, was a key skill set to go through it. I used to do it, but I became much more conscious and intentional at that time in terms of the outcome I wanted.

And just using intention as a way of empowering yourself when everything is going crazy to see that this thing can actually happen. And I can tell you so many things happen in the way that I. intended. Of course, it's overused to say, oh, you just intended it. It happens. No, you, you hustle. You know, you're working 20-hour days. You're coming home, you know, taking the kids to whatever soccer, and then you're working again, et cetera. And so obviously, the sweat is there. The hard work is there. The luck is there. You know, chances have to come in. But intention is very powerful. So I do think that intention carried me through that very complex journey. Oh, wow. So what was your intention in starting Caputo? And did it ever change?

from the evolution from Caboodle to Poshmark. Kaboodle changed quite a bit. I would say like my journey in Kaboodle was a journey of continuous sort of change, even in my own thinking and mindset. And as you asked, why did you sell it or what was the thing? I think it was all happening in real time overall. I would say with Poshmark, it has been the opposite. You know, the original plan we laid out, we literally marched towards it.

And 10 years later, we hit the metrics, very similar to the metrics we had put in the very first step for our investors. So two very different journeys. I can't say that one journey is better than the other. I was more a genius in the second journey. I think it's just to some degree luck. Or you just gave enough time for the luck to come to you. Yes, you work hard to make luck.

But I would say whether the plan changes along the way as an entrepreneur or the plan remains the same, I wouldn't necessarily quibble as long as the plan leads to some success, you know, point whatever you define success to be. And sometimes plans have to change in order to become that. I mean, think about what happened in 2020. We all had to change every single plan we had. We were just talking about the fact that, you know,

number of live interviews I attend these days is very few compared to, you know, Zoom. And that's all post-COVID, right? Pre-COVIDs, you always did everything in person. Adaptability is a key mindset that any entrepreneur has to have. So true. How did the Poshmark idea come to you? It was kind of an interesting story and I want you to share.

Yeah, sure. I had left Caboodle in 2010, and I knew I wanted to do something in fashion. So one thing I was doing, because I had come five years out of fashion, I had some ideas, but not the specific idea. But I knew this time, because I had the background, I had the credibility, I said, one of my co-founders has to be someone who came deep from fashion space, not from media space, and preferably someone who at least spent part of their time in New York or LA fashion, not Silicon Valley fashion.

Even if it's a lot of fashion companies, surprisingly speaking, you know, we have Levi's, we have GAAP, but I wanted someone who spent that time. So I kind of intentionally sat around what I call founder date to find a co-founder who had that. Because tech and product, I had lots of networks. Right. But this I didn't. So I had to kind of broaden my network to go seek that partner. Interesting. And that's how I met Tracy's son who became my co-founder for Poshmark.

So we first met, you know, I met a lot of different folks and just was not feeling the right connection. and Tracy and I, in the very first meeting, I would say we had like this instant founder connection. And part of it was that what I saw in her was that she knew fashion, but she had deep respect for technology. And what she saw in me, she says now is that even though I came from technology and product, I had deep respect for fashion in a way that was more authentic. So we kind of connected around those lines. So that was sort of happening. And we were brainstorming ideas and things. And then in August of 2010, I was on vacation in Santa Cruz area.

And one of my friends took out this little device called iPhone 4 and took a photo. And pretty soon the photo was on my Facebook. And here I was with this big SLR, you know, taking a photo, finding the time to take my SD card out, figure out a little way to shove it into the laptop, upload it, do some stuff. And he'd already like smoothened out and uploaded it. So I was like, wow, this thing is getting real iPhone. iPhone was there, but iPhone 4, and it was so clear. Everything was sort of like the display.

That was sort of first thing. So I said, okay, whatever I do has to be on the mobile phone. And so what I did at that point in time is I literally stopped using the laptop and moved 100% into mobile phone and iPad. Did everything, including banking, et cetera. This is 2010. Most of them didn't have apps. So you were like basically hacking Safari to do everything.

The second thing that happened was we were at high school homecoming. game for my son, and the homecoming queen was wearing this yellow dress. And after the game, we asked the mom, and she had thrifted it, which was not a huge concept at that time to come to, you know, the queen was wearing a restaurant on thrift store. So it started to click, like, this trend is happening, you know, overall. And then our closet had so many unopened bags, not even like used clothes. They were just like shopping bags that had not been open in two weeks. You know, many people could relate to it today, right? They're saying, sitting there. Nobody has even opened the back. So I was like, this waste problem is there. So that

everything clicked in the brain. When I get an idea and I start to feel it concrete, I write the whole business plan in two pages. That's sort of something I've done. So I have like 15 business plan sitting. Because that first fresh that comes in, you can refine it. That's sort of when you write at Ross. So that's how the poshmark thing came. There's more to life than finding the perfect car. But finding the perfect car can help you get the most out of life. Like the SUV that handles everything from drop-off to off-road, and the car that hulls groceries and hockey teams, or the van that's gone from just practical to practically family. Whatever you want, wherever you're going, start your search at ototrater.ca. Canada's car marketplace. Square knows

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Less of a catalog, but more, you know, as you're going through the journey thinking about it, you just kind of write it down. And I write it down in the following way. In fact, at Boschmark, we use it called Day in the Life Office. You sort of visualize a user. Zoe wakes up. Zoe gets a package in the mail. It's a dress she'd ordered from Julia.

Julia had just won this dress to her sister's wedding, and I was ready to. So like that storybook format, and then you sort of say, how many dresses are days, washmark selling? What is happening? So you kind of like get it down to very specifics, and that becomes a user journey and then a business plan. Then you write down features and screens. And in four or five pages, you've captured the essence of that business.

I love it. Write things down. Write things down with specificity and detail. If there are areas you can't write down, then think, harder to figure out, like, what they are. Okay. And so sometimes it takes me, like, a few weeks to write something down because I'm thinking, but when the things start to become clear, I just write it down.

Oh, I love that. It's like a download from your brain. If you don't write it down, sometimes it just disappears. You do it without the help of chat GPT. Yes. That's critical these days, right? Like, doing it purely from there, and then using AI tools to help, because otherwise they can influence your thinking.

And I think pure thinking is really important. That is so true. Not that using AI tools as bad, it might become more prominent, but, you know, I would say we're still in this evolutionary stage that your original thought may be more valuable than just your AI assistance there. It's early. So I may not know what it's going to be. That's true. Like, I would say use it as a tool, not a crutch. Yeah, and I mean early. So everything is changing, right? Like, I may be talking like a dinosaur. So I want to kind of caveat that I don't know this. So, you know, maybe full business plans will come out of AI that would be better than the business plan. So I can. from my brain. So I'm open to that possibility. We'll see. But you were like from the very beginning trying to tap into the psychology of the desire demographic. How would you describe the avatar of the targeted consumer of early stage poshmark? Yeah. So so the mindset was that if you think of shopping,

shopping is very natural. People buy. Yeah. If you think of selling, selling is not very natural, right? So in order to unlock the power of closets, across America. We didn't want to make selling selling. We wanted to literally think a 20-year-old girl sitting in her dorm room or sitting in her apartment and she just opens up the stuff and says, I want to literally put this dress out so somebody else could wear it. How can you make it super easy? So that was the mindset. The mindset was how do you make it very easy? And mobile phone was an enablement, but then we had to build a whole level of infrastructure to make buying and selling, not just simple, but fun. And so, for example, for mobile. For mobile phones,

of our first seven years, there were no ratings in that. Oh, okay. Because, you know, if a girl is putting some item from her closet out there, she feels very vulnerable. And when you give her two-star rating, it doesn't feel like it's two-star rating on the transaction. It feels like two-star rating on her style. Yeah. So we were very conscious of that.

So we were there. There was a lot of elevation of what you were doing, curation of what you were doing, curation of style. And so that allowed a lot of people to participate in that process. and that formed the early formation of Pashmar community, which was designed to uplift each other. I love that. How were you able to really tap into the psychology of this majority of female demographic? I would say one of my superpowers, my weirdness, as I call it, is empathy. I'm able to truly try to understand, you know, what people are doing.

And I really try to understand what the users wanted and thought about it. Some of the journey started in Caboodle and some of it was there in Pashmarks. It was like deeply trying to understand not what people are saying they want, but what they truly may desire. That is so true because a lot of times people don't even know what they want. And yet here you are. You figured out what they want before they knew what they wanted. Yes, yes, yes. That's very insightful.

Marketing-wise, how did you grow in the early stage? What were some? I know for a lot of startups, the early stage marketing is always. the fun is because you have to be very scrappy. Yes, no, very well said. We were in the same mode. We were working on a mobile app, and there were really no ways to distribute mobile app at that time.

No. No cost-effective ways. Just to give you a sense, when we started the company in early 2011, most girls we would talk to did not have an iPhone. And we were only an iPhone app. We didn't have a website. We didn't. Android was not even there.

Oh, wow. And so we literally had to buy, what was called a video iPod, which was like an iPhone predecessor, and hand it to our users. I remember those. They were like very thin, but they were better than the small iPod. Yeah. The iPod video had the iPhone iOS operating system. Right. So you could do everything but make a phone call. Right. And so we load up our app and give the whole device to people. How did you choose like who to gift this iPod to you? That was sort of interesting process. You know, some of it never came back. Some people never used. So it was a little bit of a hit and miss.

But basically, first we started with our own team's friends and community. And what we found was the direct friends may be not useful, but one degree away, you would find that thing. But then we would just go to local fashion colleges. You know, we went to SFSU, we went to fashion design, et cetera, and just handed out flyers. The vision we had was that we wanted to do this event. We called it 5 at 5. So the idea was we would invite users at 5 o'clock to come up.

We would serve them a little champagne, and the idea was invite, bring five pieces from your closets. We'll show you how to list. A lot of it was done at a wine bar in Soma area of SF initially and in our offices. So there are two places. We had a tiny little office. So we would invite people there. One was in south area of Bay Area and the other is north. And people would come up initially were like two people, three people, four people, five people.

One fact, at that time, 20-something-year-old girls did not want to take any photos. What a crazy concept. What a crazy concept, right? Like, you can't even eat food without eating, taking photos. We literally had to persuade them to take photos of each other. You had to beg girls to take photos. They were like, I don't know how to take photos. My co-founder, Tracy was there.

Tracy, you take photos. And Tracy was, no, no, no, you take photos. They're like, no, no, I don't know. And so, you know, when I see people taking photos at a second, like five photos in a second, it's a whole different world. And so this is not that far back. It's only 14 years back. 20-something of girls did not feel comfortable in taking photos of each other.

Or of themselves? Certainly not. Nobody was taking a selfie. This was like, I'm talking, not even selfie. I'm talking, me taking photo of you. Imagine if I'm 20-something, you're 20-something, I would be, I can't take Zoe's photos. Wow. That was the scene.

One thing, you know, Tracy and our head of community, Leanne, who's our head of community now, they both basically said, we're not going to take any photos. Here's cameras, you take it. And so part of it was that a lot of people didn't have phones with cameras. Right. And so you would take photos in digital cameras or stuff like that. And even there, you know, it was not as common to just take individual style photos as at a high velocity, right? And selfies were not even a thing. Imagine that the next generation of not just young women, but everyone kids. They grew up taking videos and digital footprints of themselves from day one. Yeah. Every second of your life is documented now, which is good. challenging. But I also wanted to ask you about intuition because you made a very big and risky bet

on going full on iOS when not only were people not using iPhones, they were not really using the video iPods. They were not even taking photos. I think one thing that I have now that I look back over the last 20, 30 years of my career is somehow I've been good at understanding technology and now more culture waves, but certainly technology waves. So I've been a lot of. I've been a good at understanding technology wave. So I've been able to unconsciously align myself with where the puck is going as a wave and then work in that context. So I could see the wave of mobile happening at that time before the world seat. Saw it, right? So at the time I was conceptualizing these things, it was also a tiny little app brewing called Instagram. It was tiny. It had just started launch out. I was one of the

early guys to start to put photos on it. Really? Yeah. Wow. And so it was, it was, it was, was just starting at that time. And so I could see that this thing is going to have potential. So that's why I bet on it, right? I think understanding both culture and technology waves is an important part of making bet. So you could have an idea, but if it's not time to a proper wave, the idea may be mature. Like if you think of Caboodle, it was leveraging a little bit of the social wave, but the mobile wave had not started. And that idea became much bigger with mobile, right? And so now if you think of many ideas with AI upon us, they're going to just explode to the next level. And so if you can think through your idea and align it with, in this case, AI is both a tech wave, but also a culture wave, right?

We're just talking a few minutes back about how it's going to transform. And then thinking how it will transform in ways that are not imaginable today is even hard. Because if you think about a Pashmark or an Uber or a DoorDash, pre-Mobile, they're going to be able. they couldn't exist. They could not exist. They only put an artifact of mobile. Now, you needed other things besides mobile to make them happen, but, you know, a website couldn't do Uber. And so those are, I think, things to kind of think about there. So the intuition part is understanding the waves and then understanding the consumer problem and then trying to marry them together. It's not a simple task. I don't think, you know, you can get it right all the time, but when you do get it right, it's magical.

That is magical. For someone who understands intuition as like a gut feeling without really a way to operationalize it, how would you put it into words as to like what are some of the patterns you recognize that just stick out to you? I think it is kind of a sense of ESP or like this weird feeling you have, you know, in there. Sometimes also unease in you like this is happening. There are two things about intuition. When it's happening, it's real, right? It may not be as real as you think, but it is really.

real in the sense that whether it's truly, truly real, something you want to bet your life on, or it's just something that's happening. That's a discerning part you have to do through a little bit of experimentation and seeking external feedback. But if you have this feeling, don't dismiss it. Like I told you, for six months, I kept dismissing that, yeah. I felt the same way. Like, during college, I was like, I really want to create a YouTube channel. For around six months, I couldn't go to sleep, honestly. I would wake up at like five or six and I'd be like, I want to create a video. But at the time, I was like getting through exams. and then trying to get through the quote-unquote essential steps of kick-starting a corporate career.

But it was always there, always there coming back. So I totally understand what you mean. And here you are. Congratulations. Thank you. Yes, yes. No, absolutely. I feel like that is the key is that you have to marry intuition with data, right?

Data or like feedback from the outside. When I have an idea, I'll try to validate from everyone I meet. Like, so if I have an idea for a 16-year-old, every 16-year-old I meet, I'll ask them the question and see what their reaction is. And by the way, in talking to the particular user or the person, you also refine your pitch, right? Because the first time you say people are like, what are you talking about?

Slowly you refine it. And people are still going to be skeptical because they haven't seen it. But once they start to see it, it becomes powerful. For example, when we said we're going to only do it on mobile, a lot of investors were scandalized because they didn't know that anyone would ever buy on mobile. Right. And they were partially right. Like the conversion rates on mobile at that time were much smaller than conversion rate on Web.

So the form factor was small, et cetera, et cetera. But because we bet on mobile, we ended up building a much better mobile app than anybody else did. So that gave us a huge advantage. And it's something that we've fortified as a company value. We call it embrace your weirdness. A lot of it is not about being weird, but it's about like understanding your strength and quadrupling down on your strength, one. And number two, which we haven't talked about.

as much about yet is in order to build anything great, you need to have a team. You can't do anything alone. Having a team means also understanding that you are not alone. You don't have all the strengths, which means seeing the strength in you and being able to partner and create that. So embracing other people's weird deaths, right? It doesn't make you any lesser. Like if you have some strengths, I don't have to have those strengths, right? And being able to respect others, leverage that partnership allows everyone to be great. I love that. How was it the process of finding the right people to bring on to the bus, so to speak? It was challenging and continues to be challenging as you build the teams and, you know, do that.

But obviously you get better at it. There you have to use, again, paper qualifications, resumes and intuition and data. You know, one of the things I talk about is that we talk a lot about building diverse teams. And diverse teams are not just teams that may look diverse by, you know, how you look, but deeply diverse in terms of point of views you bring, journeys you bring. sometimes ages, sometimes even college experiences, etc. That allows for building more robust teams that allow you to grow. And we truly, you know, we had some homogeneity at the surface, some differences.

But over time, we created a team that had many different viewpoints and many different journeys that came together. And that's what ultimately created Poshma. I love that. One thing I'm specifically really impressed about you is that I read in Fortune, you you asked your Gen Zee employees to dress you. And you're so humble and open-minded. to accept changes and to be flexible and adapt.

Yeah, I mean, I think when you live in the world of fashion, which I have now for 17, 18 years, you're exposed to a lot of things. And, you know, one thing I find about fashion is fashion is both enduring and temporal. Right. And the temporality has to be embraced in a pretty meaningful way. And right now, your generation is writing and defining, you know, where we are going in terms of fashion. So I wanted to kind of really see, you know, because there's stuff,

particularly with COVID, we created COVID blindness. so much of stuff was happening around vintage and remix and stuff like that. That's gone now because, you know, we're actually having a lot more in-person things. But remember the COVID, they were like, there was not in-person. You didn't even see what you were wearing, right? No. You just saw the face or whatever I decided to show you. And so a lot of our insight was coming through video or through social media, you know,

which is good. But to me, actually seeing people in real life is sort of so much more interesting. So I asked some of our team to help me find new brands, new styles, etc. And I've been leaning into it because I find it quite fresh. Also, I find some of the Gen Zee Stive to be more comfortable personally. Okay. And I know you have this leadership principle of if you lead with love, the money will come. What does love mean to you in a corporate setting and also on a personal relationship setting?

You know, when you think about what is love, love is this feeling that we all, ultimately, you know, I feel in some ways the focus of life is love. But a way to think about love is that when you're making a decision, quite often we are filled with dread and fear. We're like thinking, oh my God, everything's going to go wrong. Like, should I even be doing it? And then something start to go right. And then you start like, how can I get more out of it? How can I squeeze more out of it? Both of those pieces end up taking you into journeys that are not so good, right? But if you center yourself and say, things are just the way they are and it's all about sort of creating that connection, serving people in the community, then a lot of good things happen. Right. And so,

I can call it doing the right thing, but it's more than that. It's doing the right thing that also brings joy. It's something where I'm giving and receiving. It's something which is making me feel good. And that's love. But it's also, to some degree, a little bit elevated form of connection. That's not just very basal and very basic, right? And it's not transactional.

And sometimes, you know, you have relations with that transaction. That's fine. But a lot of times relationships really enjoy is where you go beyond the transaction to having a more deeper feeling of love. So hard to describe, but hopefully this gives you a little bit of a sense of that. Is it more like doing something for its own sake as an end rather than a means to an end? It is. It is. It can be that as well. It doesn't have to be. What I'm saying is let's say you have a co-founder, right? You're on a business journey.

There's clear goals. You have clear partnership. If you're the CEO, even if you have a co-founder, you're in a way, they're their boss as well. So you have to create for them as an employee, even though you're a co-founder, etc. Having said all of that, One of the places that love does emanate from is a sense of trust. It's a sense of, you know, we talked about forgiveness and trust and relationships. I think that's part of the whole thing. And I think in a workplace setting, trust and this feeling of being understood creates a sense of love. That's powerful.

I'm sure it translates beyond just work and into your personal relationship as well. Selfishly, I really wanted to ask you if you have any relationship advice that you will give to your children. And selfishly, I just want to know because I feel like you succeed in many areas in your life and in your relationship. I'm sure it's a place at the age you guys are in, you struggle a lot. Oh, yes. These four books that I recommend. Hey guys, really quickly. Because of the low attention span on YouTube, this is only part of the podcast.

The full dive will be available for intentional members who want to take the time to learn and really grow. Part two will also be available on Spotify and Apple in a few weeks. But if you do have the attention spent and want to learn and watch the full. episode. It is also on the members page right now. Thank you so much for sharing these incredible stories, the insights, and for being so vulnerable and open. I'm sure it's an inspiration and great insights to so many, not just young people, but like people of all ages and gender who are embarking their own growth journey, whether that's entrepreneurial or something else. So thank you so much. Thank you for inviting me. It was a pleasure. Thank you so much. Where can everybody find you or

Hashmart? LinkedIn. Mnishandra and, you know, And that's probably the simplest place to connect. Amazing. And then follow Poshmark on all the social platforms. Download Poshmark. Thank you. Thank you. Thanks so much.

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