The Bossticks - #101: Tracy DiNunzio, CEO & Founder of Tradesy - How To Start A Business With Minimal Resources, Pitching Investors & Raising Capital, Building Mental Muscles for Failure & Rejection

Episode Date: February 13, 2018

On this episode we have Tracy DiNunzio on the show. Tracy is the founder and CEO of Tradesy. On this episode we discuss how to start a business with minimal resources, bootstrapping (that famous start up term), pitching investors and eventually raising capital if you need it, what it takes to be an entrepreneur, building up mental muscles to deal with failure and rejection, and taking feedback (good and bad) the right way.  To learn more about Tradesy click HERE To connect with Lauryn Evarts click HERE To connect with Michael Bosstick click HERE Read More on The Skinny Confidential HERE This episode is brought to you by Zola.com.    Zola is the wedding company that will do anything for love. They are reinventing the wedding planning and registry experience to make the happiest moment in our couples' lives even happier. From engagement to wedding and decorating your first home, Zola is there, combining compassionate customer service with modern tools and technology. All in the service of love.   To sign up with Zola and receive a $50 credit towards your registry, go to www.zola.com/skinny 

The following podcast is a dear media production. This episode is brought to you by Zola. So as you guys know, Zola is the way to go when it comes to the wedding registry and the wedding planning process. Trust me, this is totally a thing because over 300,000 couples have used Zola. So basically Zola Registry is everything you love about your favorite department store. Plus, it includes things like honeymoon funds, fitness classes, wine subscriptions. Yes, please.

And so many different creative ideas, we even did a donation. to charity. They have over 500 top brands, tons of experiences, like I said, donations to charities, and even cash funds. For our wedding, I didn't want to hassle our guests, so Zola took all the hassle out of it. It kind of makes the whole situation seamless for everyone. It's a win-win. To sign up with Zola and receive a $50 credit towards your registry, go to Zola.com slash skinny. Again, that's Zola.com slash skinny. Stock this site. You will love it, especially if you're a bride. She's a lifestyle blogger extraordinaire. Fantastic.

And he's a serial entrepreneur. A very smart cookie. And now Lauren Everts and Michael Bostic are bringing you along for the ride. Get ready for some major realness. Welcome to the skinny confidential, him and her. Welcome back, guys, to the skinny confidential him and her show. This week we have Tracy Dinoonzo on the show. and Tracy is the founder and CEO of Tradesy. I'm sure you guys have all heard of it.

If you haven't, Tradesy is the world's leading peer-to-peer marketplace for women's fashion. On this episode, we discuss how to start a business with minimal resources, bootstrapping, that famous startup term, pitching investors, and eventually raising capital if you need it, what it takes to be an entrepreneur, building up mental muscles to deal with failure and rejection, and taking feedback, the good. the bad, the ugly in the right way. For those of you who are new to the show, I am Michael Bostic. I'm an entrepreneur, investor, and business operator.

I specialize in brand development and business growth. Over the last 10 years, I have developed, helped to develop and manage brands and businesses in a variety of spaces. Most recently, the co-founder of Dear Media, a new kind of podcast company with an emphasis on female hosts and voices. Dear Media will place women, their stories, and narratives at the forefront of conversation. I like it. And I'm Lauren Everett's.

Michael's better have? I don't know. Well, they only have one right answer to that. Yes. I created the Skinny Confidential as a blog eight years ago now. I was attending San Diego State. I was bartending, teaching Pilates and Peerrora R and just bored unfulfilled and wanted to create a space for women on the internet and bring together a community. It's really cool now to watch all of that come to life. The Skinny Confidentials is a YouTube channel, a podcast. Like I said, a community and a book, which is available on Amazon. So. What's been going on?

A little slow Sunday for you, huh? A little slow Sunday. Catching up on Monday. You know, a lot of you guys know, we record these episodes. You know, we batch them up because we get busy. So we batch up a bunch of episodes. And then we'll go back the day before they're released and record the introduction so that we can, you know, give a little fire introduction.

Well, we want to keep it fresh and we want to stay relevant. Yeah, you know, I mean, we did this interview a couple weeks back, which is not too far back, but you don't want to come in and be like, remember Christmas last year? So we always come in and do a little update. And sometimes, you know, Mondays are tough. Yeah, we had a nice weekend this weekend. We hung out with each other. We did a conference yesterday or more like a brunch.

I got to meet a bunch of you guys. And tomorrow we are going to the movies, like me and you guys. 75 of us are going to drink rosé, eat popcorn, and see the movie 50 Shades of Grey. I couldn't tell if you were just like, there for a second, like talking about, like, there's 75 of you personally. Like, you'd like, for me, when I'm sitting here listening to you, you just sound like a, like a psychopath. You're like all 75 of us, which wouldn't surprise me because you do have about 75 personalities. I feel like it's 80 after this weekend. You know what? That's how I spent my Sunday. So obviously

we're building out the studio up in Dear Media up in L.A. It's going to be an amazing studio. Top-notch, top of the line. Gorgeous. A lot of bright light for Instagram too. But right now I've been splitting my time, San Diego, L.A. I'm probably going to have to be up in LA a lot more, which I know you're fired up about less time in San Diego. I was just going to have to deal with it. But my Sunday was spent driving up at 10.30 at night, last night, to L.A. so that I could be there for meetings all day today. With the bare naked cucumber in the car. With bare naked cucumber, who, for those of you who don't know who he is, Taylor, he's been working, go back to some old episodes. He pissed himself at our wedding and went to a strip club and then proceeded to do

like a whole lap dance situation. So yeah, he was up there because he's looking at some of the tech stuff. But anyways, so then I had meetings up there and then came back today, got back at 6, and then did some bunch of stuff down here and now doing this podcast intro at 1130. An autobiography by Michael Bostic. It's a lot, guys. It's a lot out there in the life of a podcaster. So tomorrow we get to see a movie.

I'm forcing Michael to go. You know what though? No, don't try to get out of it, Michael. Listen, one of my big pet thieves is I hate to jump into sequels if I haven't seen the first ones. But I think for this series, I'm going to make an exception. And I'm going to miss the first shades of gray. What is it? Shades of Gray 1, 50 shades of gray, and then what's this one?

I don't know. It's like 50 shades of something. We're going to Synopolis so the chairs will be comfortable. Few people might have to sit on the floor. I might be one of them. You might be one of them too. I'm fucking sure as hell won't be one of them. I guess you should.

Shibblery is dead. Michael, you might have to sit on the floor. I'm not joking. I will leave the theater. Bring a barefoot dreams blanket. There is nothing I would not do more than sit on the floor during 50 shades of gray. It's not happening. You know, sorry.

You'll get popcorn. I don't care. You could, I don't care what you give me. It ain't happening. Um, okay. Well, it's going to be fun tomorrow, you guys. I can't wait to hang out. I feel like this is the perfect meetup.

Uh, we get to watch a movie. I drink a little rosé. We're bringing goodie bags with valentines in them for you guys. And it's going to be fun. Slip some woo in there. We slipped some woo in there. All right. So it's really cool to watch the Skinny Confidential secret Facebook group expand.

You guys are hanging out in different cities without me, which is awesome and amazing. You guys have met a lot of friends. I think someone held a Skinny Confidential New York meetup the other day. If you want to host a meetup in your own. city. All you have to do is go in the group, join the group, and then search the subgroup that has to do with your own state. I think it's really awesome that a bunch of you are meeting each other in that group. It just makes me so happy. I can't even tell you. To become a member, you're just going to search the skinny confidential in the search bar, and then you just click join. And I go through

and I approve to make sure there's no guy sneaking in. We do have one guy, but that's a whole different story. His name's Gary. But basically Gary's our mascot. So it's a bunch of women and then Gary. A lot of you guys are brides in the secret Facebook group. I've seen a lot of people that are getting married or they're engaged. So I think that Zola is perfect for you. As you know, Zola is the way to go when it comes to the wedding registry and wedding planning process. We've talked about this a lot because we used it for our wedding and it was a total lifesaver and really streamlined everything.

I feel like it's also a big thing because, like I said, over 300,000 couples have used Zola, which is nuts. Basically, Zola is everything you love about your favorite department store. Plus, it's also a medley of things like the honeymoon fund, fitness classes, wine subscriptions, and so many different creative ideas. What did you do with our honeymoon fund? Do you think I'll ever be able to share in that honeymoon fund? Or did you just... We still have it.

We haven't gone on a honeymoon. I'm waiting for you. It's not put into shoes or something that I don't know. What's happening on Valentine's Day? Hopefully I'm going to unwrap a honeymoon. No, we have a honeymoon fund waiting for us. We did a honeymoon fund and we also did a charity where we donated money to colon cancer research and to the Chihuahua Fund, which was very on brand for us.

They have over 500 top brands, tons of experiences, and even cash funds. For our wedding, I didn't want to hassle my guest. So Zola took the hassle out of it. It kind of makes the whole thing seamless. for everyone. Super easy for couples and their guests. You guys should also know the customer service team really goes above and beyond to help you pick out the ideal gift for the couple. Also, there's this thing they offer called group gifting, which allows a bunch of guests to contribute to a huge gift. So fun. Well, it makes it easier on the guest, too, I feel like, you know, you don't want to

like, it's already a hassle. Listen, I know it's your wedding. And listen, I felt the same way. My sister's wedding's coming up. Our wedding was there. And it's an important day, but you, you know, it is an imposition on people and you want to make it easy on them and make so they enjoy it. I know brides are going to come out and rip my face off of this. But it's true. Like, you know, like think about when you have to go to weddings and so. So you want to be nice. I like to make it easy.

But yeah, Zola makes it easy. You're going to get some good gifts, you know, you skip all the, you know, toaster ovens and all that stuff. As the bride and groom, you can even personalize your registry with photos and notes about why you want certain gifts. I love this. I love a story. I love personalization. You guys know that about me. Of course, Zola does price matching and free shipping every day, which is kind of insane.

I also think it was fun how our registry automatically integrated into their Zola wedding website so the guests could seamlessly shop and get all the details they needed in one place. It was efficient, which you know I love. We also did like a newsletter blast where we sent kind of the whole thing to everyone and it went out and they could just go on the site and easily shop. So that's an idea too. Yeah, and for those of my friends that didn't get me something, I see you on that list. Yeah, he's like Santa Claus making a list. I make a list.

Checking it twice. Yeah, a lot of noughties on that list. Taylor, to get even more excited, Zola has a customizable checklist and guest list manager. Best part, though, is Michael and I even manage the whole situation on our phones because they have a quick, easy-to-use app. That's a lie, you didn't manage it. I managed it. Just me. super quick to sign up with zola and receive a $50 credit towards your registry go to zola.com

slash skinny that's zola.com slash skinny for all your registry needs that's zola zola.com slash skinny go stock it you will love it especially if you're a bride all right all right all right let's get into the him and her tip of the week okay so we haven't had like a businessy podcast in a while and it's been, it's starting to be requested. So I think this is a great, Tracy, it's going to be a great episode. And because of that, I wanted to give a businessy or, it could be applied to anything, but let's say it's like a businessy tip of the week. So in our podcast Facebook group, we're getting ready to possibly do some solo episodes

and really niche down and figure out, like, if we were each to do a solo episode, what topics you want us to cover you as the listener. And a lot of the topics that are coming through for me is business. and niche subjects and businesses. But one of those questions that's being requested a lot is multitasking and how to do multiple businesses. And I just, I want to make sure that I'm giving out the right message here when we're doing this podcast or when I'm giving advice.

I actually think it's a huge mistake when you're starting out to try to do multiple things and run multiple businesses. I think at this point in my career, I'm able to juggle a couple more things because I've built out to really solid team under me. and with me. And so I'm able to do to delegate my time and be involved in different projects. But that was definitely not the case in the beginning. So if you're just starting out and I think a lot of very successful entrepreneurs and business owners and operators will tell you the same thing, when you're just starting out, whether that's a blog or it's a podcast or it's a business,

whatever it is, I actually am not a fan of doing multiple things. I'm a fan of doing one thing and really, really honing in and getting good at that thing. There's an amazing book called The One Thing by Gary Keller that basically supports this theory that I'm talking about, which is basically focusing in on one thing day after day until, you know, that one thing it snowballs and becomes a huge thing. And then I think it's able to, you're able to branch out. So kind of to niche down here a little bit and get more specific. When you're first starting out, you know, you're excited and maybe you're starting a blog and then you start to get a little bit of traction. Like, okay, this blog's going really well. So maybe I'll create a makeup line.

and then that's going really well. So maybe I'll create like a health line. And then I'll create like an ebook product. Like this is very common when we go and speak and when I when I speak to a lot of of you saying like, hey, I have this, this, this, and this going on. And while I want to be supportive and say, hey, good for you, a lot of the time I find myself wishing that I'd said, hey, get rid of a lot of the majority of those things and focus on the one thing that you can truly maximize and profit from.

For example, we take Lauren. She really, really focused in on her blog in the beginning, blog content to a specific audience. And since then, it's been able to umbrella into different things. Me, like my first career was JetBed and we really, for the first like four years of my life, or my business life, just focused in on building out JetBed. And from there, I was able to go into marketing and then I was able to go into different investments and obviously some other businesses since then. But I think if I would have tried to do all these things out the gate, everything would have failed.

So I think when you're starting out, it's super, super important to really, really hone in on that one thing to start with and build that up so that you have a foundation to build other things if eventually you want to do those things. So I just want to make sure that I'm putting that message out there and I'm not confusing people into thinking they have to do multiple things all in once. I think multitasking can be very, very dangerous and destructive. So my tip of the week is when you're starting out, focusing on the one thing. And then even when you start to branch into other things, make sure the other. other thing, the first thing is running smoothly and operating, I don't want to say on its own, but running like a well-oiled machine before you take on another task. You don't want to be juggling 50 things like an octopus. It's just not going to work. Great tip, honey. Okay, so my tip,

since we're talking business, has to do with my favorite thing ever, which is branding. You guys know I love branding. If I wasn't a blogger, I think I would be a branding specialist. maybe an interior designer, but probably a brand specialist. There's this book that I read that I featured on the Skinny Confidential, but I want to talk about it on this episode because I think it's a book that everyone should go out and get. You can find it on Amazon. We'll leave it in the show notes. It's called The Brand Gap. And I just think it really lays out business strategy and design of designing a brand. And just to give you a couple spark notes, I kind of wanted to just lay it out. for you before you buy it. And when you do buy it, you'll get more information out of these

spark notes. So the first note is a brand is not what you say it is. It's what the consumer says it is. Don't you agree, Michael? It's the emotional reaction individuals feel when they see your brand and listen to your audience. So with the skinny confidential, I have always wanted you guys to use the skinny confidential as a resource. And when you leave, I want you to leave what you don't like, take what you like, apply it to your own life, and I want you to feel inspired to be the best version of yourself in an unapologetic way. I think that that was really important for me. It wasn't just for you guys to leave with my outfit deets or what I was eating or how my hair looked. I wanted you to leave with something valuable that you could apply to your own life.

So next spark note, a branding has nothing to do with data, numbers, and Excel sheets. Nothing at all. It's about the people who experience the brand, not the number. So stop looking at the data, look to the people. I've always done that the whole time I've had the skinny confidential. I just think constantly being buried in your analytics is really counterproductive and looking at your following count every second. I think it's all about the community. I always say that you should focus on the audience that you have, even if it's five people. You should focus on serving them and from there they'll go out and tell more people as opposed to taking those five people, ignoring them and trying to get more people.

The next spark note is a typical design has four goals to identify, inform, entertain, or persuade. However, when it comes to branding, there is a fifth to differentiate. This comes down to strategy, guys. So why do you like Nike over other shoe companies? Because honestly, Nike's done an incredible job of differentiating its brand. And if you look at a blog or a blog that you really love, why do you like them over other blogs. I think that it's really important to stand out in the market and do something different. You know, I was talking to someone the other day and I think to be successful, you know, you do need

to look at other people's formulas and maybe some people will copy those formulas, but to be remarkably successful, you need to do something different that's down the road that's, you know, being ahead of the trend. Another one, which I feel like this one applies to the skinny confidential, is brands can become small tribes if they're done right. Your vibe attracts your tribe. Community is key. Community to me is everything. It's always been everything. It's why I do what I do. I've told you guys this when the secret Facebook group launched. It made me emotional because it's what I've been working on so hard the whole entire time I've been blogging. And I can see in that Facebook group that the vibe has attracted the tribe. You guys are so cool and amazing and you guys are all

viking off each other's energy. So if you're building a brand, make sure that you are building that tribe and that community. It takes a village to build a brand, so you've got to take the ego out of it. Not one person can develop a powerful lasting brand without a strong team of people around the brand's message. This is you guys. Collaboration is so important. I talk about that a lot. Of course, engagement. I'm always, you know, looking at what you guys are doing and talking and engaging. It's my favorite part of the job, my favorite part of the gig, meeting you guys. It's awesome. Okay, so I'm going to give you two more, and then I think you should all go read the book if your business owners or bloggers. The next one is to pick a strong icon and a name. So

criteria for a good name is appropriateness, easy spelling, punctuation, like ability, and protectability. So keep that in mind when you're picking your name. Lastly, I'll leave you with this because I think it's important you guys read the book, but a brand should always lead with authenticity. Authenticity is a word that's completely overused, but it is true. Your brand should lead with that. Your audience feels that. Your community feels that and that is important. So check out the book. It's called The Brand Gap. It's super cheap. I want to say it's like $9 on Amazon. We'll leave it in the show notes. But I also have to give a shout out to another book, which I'm in, which is called Crushing It by Gary Vaynerchuk. I am so excited because he featured me as one of the entrepreneurs

in the book. Gary is a huge, huge inspiration for me. We've been a on his show before. He's been on our show. And he just wrote this book about a bunch of people who were scared, just like you, who had obligations just like you, who were told they were being foolish or reckless or irresponsible, just like you. And they did it anyway. And they reaped the rewards. And he basically showcases a bunch of different entrepreneurs in his book and gives you so many incredible tips on how to build a brand in 2018 on social media. So make sure you check out those two books. I'll leave them both in the show notes. And with that, let's meet Tracy. Tracy Dnunzio is the founder and CEO of Tradesi, the world's leading peer-to-peer marketplace

for women's fashion. As an artist-turned entrepreneur, Tracy bootstrap the business in its early days by running out her bedroom on Airbnb and sleeping on the couch. Wow. Today, Tradese has a team of a hundred team members and five million customers that have attracted funding. from top-tier investors like Richard Branson and Tim Ferriss. So I just want to throw this out there. I actually have had my closet on Tradesy since 2013, guys, which is nuts. You can shop my closet. It's a bunch of my clothes. It's Tradesy.com slash closet slash Lauren Everett's. If you also Google the Skinny Confidential Tradesy, a post will pop up. I find Tradesy super easy to use. user-friendly, and they also have some really rare and unique pieces that you can shop.

Honestly, I found some really, really good finds on there. So go check it out, tradesy.com slash closet slash Lauren Everts, or you can just shop tradesy.com. With that, let's welcome Tracy to the show. This is the skinny confidential, him and her. Tracy, how did you get started? We want to hear the whole nitty-gritty. Okay.

Hey. Well, I was a painter, an artist, and after the 2008 crisis, nobody was buying my paintings. And I had an idea. It was actually an art concept to create this universal online closet for women, where we could all share our clothes, like having millions of sisters. And so I got really inspired to just create that and started building it at my kitchen table on my laptop, quickly. found out that I needed to hire or contract or beg some people to help me build it. But that was the original concept for Tradesy. It was an art project about connecting women and our closets so that we could feel like we had a support network of sisters. And then I quickly recognized that it had some good business potential and started looking

at it that way as well through that lens. I read somewhere that while you were building it, you were actually Airbnb out your bedroom while you were staying in the house. Well, okay, so I was teaching myself how to design and code and market and all of that, and I got really obsessed, and I would fall asleep on my couch with my laptop on my chest, like every night. And then one night I saw this ad on Facebook for this new thing at the time called Airbnb, and I thought, gosh, I'm not even using my bedroom anymore.

I just fall asleep on the couch working every night. And I had a well-located apartment. I thought people would want to stay there. So I went for it and ultimately ended up renting out my bedroom for a really long time. Then my roommate moved out, rented out her bedroom and earned enough money to be able to stay focused on the business and even invest a little bit into growing it. No, I think it's extremely like inspiring to hear about because I think a lot of people that listen to this show, they think, okay, I need all of this money to start moving. on my idea. And I think you're a perfect example of someone's like, okay, you just got started with what you had at the time. And as you evolved, you, you know, you brought in the other pieces

and you brought in some money to fund the business. But it wasn't impossible to start the business with what you had at the time. Totally. I think it's so easy to, and I was almost so ignorant that it was bliss. I didn't realize how much money it really would take to build something like this. So I jumped in with both feet. And then as I encountered phases, where it required more capital, I figured it out. But you don't need anything to get started except the will. And I'll say enough money to pay for your basic living expenses. And for me, Airbnb helped to create that opportunity.

I took side jobs. I really hustled for a couple of years just to make rent and oftentimes didn't make rent and had those like cute eviction notices on my door. But it was all part of the journey. and I think you can start wherever you are. What would your advice be for someone that's listening that has a big idea like you had? Where would you start? Oh, that's the hardest, right?

You really break it down into pieces and then smaller pieces and smaller pieces in terms of what are your first steps. And I would say something I didn't do, but that I think is really useful. And when I work with budding entrepreneurs now, I encourage them to do this, is create a deck and a financial forecast as if you were going to go pitch investors about the next five years of your business. And you can Google all of this. What does a great deck look like for early stage investor pitching?

What does a good financial forecast look like? And it's not that you'll even necessarily take those out into the world and use them to raise capital. It's that the exercise itself is so clarifying to help you understand where you're going. if your business works, at what point you can expect it to work. And that will help you set realistic incremental goals along the way. There's a really good article by Guy Kawasaki that basically shows you how to write a pitch deck. I think it helps you frame it out.

It's basically what is it 10 slides? Exactly. And then that kind of forces you to say, okay, what are, what's my real answers here? What's my problems? What are the solutions? You touched on something. You said in the beginning you didn't really know what it took, right? you didn't know how much capital it took and how many resources are going to take.

I think that that can be a blessing in some ways. Like if you knew everything you know now, do you think you would have got started at the time? Oh, I would have been terrified. And I may not have started. I may have thought, well, that just sounds impossible. It's just not achievable. I was, again, just ignorance is bliss. I thought, gosh, if I just had $50,000, I could really build this thing.

And I can tell you that almost nine years after starting on this, we've raised $80 million in venture capital financing. So my 50,000 estimate was like slightly off. Yeah, a little bit. And I really had no idea what it meant to build a business at scale. But you can learn that as you go, because no matter how much you know on day one, you've still got to put the first brick in the building and then the second. and you are equipped to do that. So let's talk a little bit about bootstrapping. I think a lot of people now, you know,

they go and get venture money right off the gate and maybe they don't have a lot of experience. And so when you do that, you kind of, you start hiring and scaling your team immediately. And then maybe that founder doesn't know what it takes to be in the sales department or the customer service or basically get your hands dirty. And next thing you know, you've spent a ton of money.

You don't really know where it all went. You don't really understand how it got spent. What do you think the benefits of bootstrapping of business? like this are. Yeah, that's exactly right what you said. I mean, the three or so years that I spent in pure bootstrap mode taught me so much. And, you know, it's hard to tell someone who's starting out stuff like this, because if I thought money was an option, investment money was an option when I was

bootstrapping, I would have gone and gotten it. I just, you know, I didn't have a network. I didn't have an education in this stuff. I didn't know any investors. So it wasn't accessible to me to go out and raise capital. And the fact that I was forced to learn how to build and do every single job on the team myself, and I did them all pretty poorly. But when it came time to hire people to do things like marketing or design,

I had enough fluency to understand what I should expect from them and where I wanted them to be better than I was. So yeah, that education is irreplaceable. Is there a book or a resource that you would recommend to someone that's looking to raise capital? Oh, gosh. There are so many now. There weren't as many back then. The classics are, I think it's called Venture Hacks with the Bradfeld sort of guide to raising. And now there's also a lot of great info on Angel List as well.

but it's really changed even since I was in the early stage trenches. Like now you can Google what it's like to raise in early financing an angel round of friends and family around a seed round from VCs and find abundant information. So I'm old enough to remember when if you wanted to know something, you had to like go to a library. It sounds ancient. I can't even believe it. But for me, part of why learning how to do all this stuff was so exciting was that we saw. suddenly gained access to all the information in the world when we got the internet, when we got the mobile internet. And so there's never been a greater opportunity to teach yourself anything

than there is right now. And I think it's easy to lose track of that and all the noise of the connectedness of the internet. But Google it. Like, it's all there for it. We're having a conversation about this in the car because there's a couple of people we know that, you know, they say, well, this doesn't come naturally to me. My theme of my entire life has been figure it out. You find a way to figure it out. And it doesn't matter if it comes naturally to you or not. You just got to figure it out. There's not been one thing in my whole entrepreneurial life that I've known when I started. Yes. And that's the fun of it, right? Like I lived in Mexico for a few years and I always look back on the first year as so much fun because I was both living a life and learning the language at the same time.

So my brain was really on fire all the time because I wasn't just doing what I was doing. I was doing what I was doing in a new language while learning the language. And that's sort of what entrepreneurship is like. So there's a lot of humility and strength required because you are in the unknown and also being asked to be a leader. So that's a really scary place to be. You know, you're saying I'm capable of running this business and also I don't know a lot of stuff. But for me, at least, I've also always been so curious. And there's never been more access to learning than there is today.

I had no, I had never used Excel. I have never worked at a company in my life. I was an artist. I got, I had ninth grade math. That was it. Never took a business class in my life, knew nothing about tech. And, you know, we're doing all right. You figured it out.

Yeah. So you, you obviously, you've met a lot of, of successful people now. You're a successful person. You have a lot of mentors. What do you think one quality is in these people that you see consistently in order to be entrepreneurial? I think it's that curiosity for sure. And also a high tolerance for chaos and uncertainty. I would say, like, I tend to be anxious and want to make everything right before I go to sleep at night. You know, before I started the business, it was like, unless everything was resolved, I didn't feel like I could go to sleep. And since starting the business, I've had to

really develop a capacity to kind of live in chaos and uncertainty without letting it trigger my anxiety. So I go to sleep now. It's hard. Oh, my God. It's hard. I want you to talk more about living in chaos. I want you to really elaborate on that because I've had to teach myself to do that too, and it's very hard. As a perfectionist, we were talking about this earlier. How do you kind of manage that? it's very hard because if you're the kind of person who's starting a business you're probably the kind of person like how i was who wants to you know who thinks they can control and fix everything um and then you you in order to really run a business well you actually have to let let the kind of chaos of the puzzle unfold and guide it instead of trying to fit all the pieces together so if you're trying to fit all the pieces together you're going to exhaust yourself and create an environment in which teams can't work. In order to allow a team to work and develop, you kind of have to stand back and be okay with a lot of things constantly being unresolved. Sounds like your parenting. It's similar though, because you have to step out and let the child make the mistake

and have them learn from it. Yes. And I don't have kids and I often think that my parenting instincts go into the team a lot because it really is like having kids. And if you're doing it right, your kids need you less and less, right? You're not raising kids well if you teach them to be constantly dependent on you for answers. And so with a team, it is similar. But also within yourself to be able to withstand all of that uncertainty, it just takes tons of practice and like talking to yourself and saying like, if it were all tied up and neat and resolved,

that would mean I wasn't pushing the boundaries enough. If you're innovating and you're stretching, then there's going to be some degree of chaos and uncertainty. And if everything is really easy to manage, you're probably staying too safe and not pushing to your highest capacity. You got to get uncomfortable. And that gets extremely boring, too. What? That gets extremely boring when you're just playing and safe. I would rather try something innovative and push the boundaries and crash and burn than just kind of coast along.

I would too, but then those moments of crash and burn can be really. devastating. So you also build up muscles to withstand rejection and failure because those are inevitable along the way. So let's talk a little bit about failure. Do you have a particular failure in mind that at the time seemed crippling but ended up being a blessing and driving just a success? Oh boy. I've a ton. I can tell you that after I launched the early version of Trade Z, which was a wedding marketplace. I thought, six months in, when we had a couple of customers, I thought, see, this is all going to work.

I should start another site. And I started another marketplace for baby and kids clothing. And gosh, that just, I took all of my early profits, money that could have paid the rent, and I put it into this new business because I thought I was going to be able to run two businesses and grow them both at the same time. and that just, it was so ill-conceived and misguided, and it crashed and burned so spectacularly.

So that was an early humbling moment. I've had a moment in 2013 where I was raising money for the company, raising our Series B financing, and I had three deals on the table that I thought we were going to get all of them, and right before Christmas they all fell through. I spent Christmas through New Year's in a fetal piece, position crying and thinking I had ruined the whole thing and let everybody down. And then we came back after the holiday. I said, I'm going to move to Silicon Valley for a few weeks and I'm not coming back without a term sheet. And we were really able to turn it around, became one of the hottest

deals in Silicon Valley, got great investors on board, got a better valuation than expected. But yeah, there have been the moments of failure and rejection and disappointment come fast and hard. And as long as you develop resiliency to get back up out of the fetal position, you get enough at-bats to score. It sounds like the theme of your story is resourceful. You got resourceful. Yes. Being resourceful, resilient, all of that I think is key to surviving the entrepreneurial journey. What is Tradesi's why? And how important is that why to you? I've been talking a lot about this on the Skinny Confidential. Your why. Yeah. It's so important to have a why. And when you lose sight of your why, it really shows in your business. So very simply stated, the why for Tradesy is to create sustainable commerce. So, and I'll give you the quick backstory on that. I mentioned that I lived in Mexico. I also lived in some other places. And when I came back to the states, I was really stricken by how much disposable consumer stuff we were.

were consuming and throwing away. Like I, living abroad in the places I lived, if I was done using something, I found someone to give it to, and they valued it. And in the States, I had reverse culture shock. It really struck me how much we were just consuming and trashing things. And fast fashion was at its peak. And it was really like myself and all of my friends, we were buying all of these cheap, poor quality goods that I then learned were made in ways that were really bad for people and the

planet and we were consuming them like junk food you know i'd have a hundred t-shirts in my closet but nothing to wear and i thought gosh this is really it's unsustainable in so many ways it's unsustainable for us as women we're being sold garbage you know we and when we wear it we don't feel good we think we're going to and then we don't it's disappointing customer experience of owning these types of disposable goods um and then we're we're participating in a consumer culture that isn't supporting people or supporting the environment. I mean, fashion became one of the top five most polluting industries in the world over the last 20 years. And I thought, this is so silly.

My friends and I, when we go to each other's closets, we always feel like we found treasure. There's so much stuff already in the world. If we could just use these supercomputers in our pockets to connect all the people and all the stuff to each other, we wouldn't have to go to the mall and empty our wallets and come home with piles of disposable crap. And maybe we'd be more thoughtful about what we buy knowing that it's going to go to someone else and have a second lifetime and maybe even a third. And so the why for Tradesy is to connect women who make or influence 85% of all consumer purchasing decisions. So we determine what consumer behavior looks like. And our why is that we connect those women to create an

entirely separate peer-to-peer economy, first around fashion, and then ultimately around all consumer goods, so that we create a world where demand for disposable goods goes down, and the life cycle of products is extended, and everybody has access to really high-quality consumer goods. That's a why. I like it. I like it. That's a little long, but that's the why. With the political climate, a lot of people, you know, they really get down on oil and gas,

and I think that's fine. but people don't realize how traumatic, you know, the clothing industry is on the planet. Like there are so many problems in this industry that causes so many issues for this planet. People just don't think about it. They think oil and gas and the typical, the talking point things, but the clothing industry is crazy. I mean, you've got oil and gas. You've got industrial agriculture and fashions right up there. Some say it's the third most polluting industry.

Some say it's the fifth. I say either way. Like, we could do better with it. So what is a perfect customer experience for someone that comes on Tradesie? Like, walk me through it. Yeah. So the perfect customer experience is that you, maybe you're looking for something you really want, like a Chanel bag. Like my Paul Green, white loafers that I can't find anywhere in a seven and a half.

I don't ask for much. I feel like we just take those to a cobbler and they're going to be like new anyway. Okay. Michael, get on it. Are you on it? Yeah, let me find the local cobbler. Yeah, so you would come to us, probably find us when you're looking for something that you want, maybe like a luxury bag, et cetera, and then be pleasantly surprised to see that it's up to 90% off the retail price

because everything on our platform is pre-owned. Some of the products for sale on trades, and we have millions and millions of fashion items for sale. Some of them are pre-owned but never used, if that makes sense. Every woman knows this. Like you bought that amazing dress and never wore it or you got a bag or a pair of shoes and carried them once or twice. So we have a lot of pre-owned but like new. And I have to give you guys a shout out right now because you guys gifted me the most beautiful white Chanel purse. And it looks brand new and I still have it and I still use it and it looks brand new.

I mean, you would never know it's used. That's the thing about these really high quality luxury goods is that they are. more durable, they last, they don't look used or feel used. And that's sort of the whole point of owning something high quality is that after being used for a time, they retain their integrity, their value, they appear like new. So yeah, I mean, I have a vintage Chanel bag that is just starting to show a little bit of signs of wear on the leather. And even that, I think, is beautiful because it's out of life, you know? It is. Yeah. How is, you know, your business evolved, like if you could get, look, step back and look at it from the beginning to now.

Oh, I think initially, um, we were focused on, um, creating a certain type of customer experience. And as we've grown, we've, we've learned, um, how much we can leverage technology and data to create a, a marketplace system that is truly, truly scalable. Um, so starting off, I just wanted to bring this experience to women and see what kind of impact we could make. And now we have ambitions to create groundbreaking technology that enables the peer-to-peer marketplace to really scale and thrive. So I think in that way, internally the work we do and how we think about the business has changed. When you were developing this business, you inevitably have to, as you grow, you have to come up against the eBay's of the world. What is your take on that and how were you guys able to navigate that competition?

Yeah, competition is a big thing in our category. So eBay's always been there. Maybe not always, like not since the beginning of time, but they've been there for a long time. And what we learned when we started was that less than 3% of women who shopped online had ever sold online. So we knew that for whatever reason, eBay's platform wasn't turning all the women who shopped into sellers. Yeah. And when we talked to women, we found out that that was mostly because they found three things difficult, listing, shipping, and returns on the selling side. So we decided to solve for that. But we didn't just have competition from eBay because we saw Tradesia as a way to fill in something that eBay might not be providing to the market at that time. Which I think is super smart. A lot of people think they have to come up with this brand new idea that's never, the world's never seen. And you could just basically take something that they have. have seen and greatly improve upon it.

Totally. And think about it through the eyes of a different customer. Like I think traditionally we know that a lot of the products and services we use were conceived of by men and built by men and therefore end up feeling like they were built for men as well. So that was the opportunity that I saw. I felt like, gosh, eBay just doesn't speak to me as a woman. This experience doesn't feel geared towards me. And I thought there was an opportunity to create an alternative really specifically.

for the way that women wanted to sell and shop. But competition is so interesting because it turned out to not be eBay. That was our competition. It turned out that this idea of fashion resale online was having a moment right around the time that I thought of it. I wasn't the only one. If you have a good idea, a lot of times, you are not the only one having that idea. Yeah, like when an idea's time has come, something really interesting happens, and you see pockets of people in different cities totally unrelated coming up with the same ideas.

And early on, I would see competitors emerging and I would say, did they like hack my computer? How could we have thought of the same thing at the same time? And that's actually not uncommon, I've learned. But we ended up having 23 venture-backed competitors in this category. So the category became really... And how many of those 23, though, are still around today? There are four of us left here in the U.S., major players. There are a handful of smaller ones, but I would say that the field has narrowed down to four kind of major players in the market from that 23.

And so there remains competition, but fewer bigger competitors. Have you ever heard of a guy named Bill Gross? Yeah, totally. He did a speech, and he basically said a lot of people, they misunderstand the most important. trait in a successful business and it's timing. A lot of people think it's funding or the idea it's timing. And I think, you know, it's hard to get that right. A lot of it comes down to luck, but a lot of it also comes down to like listening to what the consumers are saying and seeing what other people are doing and waiting for that time. And if your timing's off,

even if it's the best idea in the world and you're the best team, you can be in a lot of trouble. It's completely true. I mean, you can look at our category and other categories and see that other people thought of these concepts, tried them out. but the market wasn't ready or the technology platforms weren't mature enough or the ways in which, you know, peer-to-peer shipping could be enabled were not fast enough to really meet the needs of the market. And so there's, I mean, a great example of this is YouTube. There were a ton of streaming video services on the internet. A close friend and early supporter of Tradesy had one of these businesses so I know. And it was like, he put streaming video on the internet almost before anybody.

But it also didn't matter because the market wasn't ready. Yeah. Talk to me about your morning and nightly routines. I'm obsessed to hear about, you know, successful, happy people and what they do in the mornings and the night. Oh, my goodness. Do you like a routine situation? I don't. So I'm still like a bohemian weirdo and I don't like routines.

And I used to listen to CEOs talk about that. And they'd be like, I wake up at 5 a.m. and I do a one hour workout. And then I check my email. And I'm like, I might, if I don't have a meeting, like, roll out at 9.30 and lay in bed doing emails for an hour. You know, I actually don't like to have a routine. The only thing that's consistent is morning coffee. And then at night. Sparkling water, you said too.

Sparkling water. Only fizzy beverages and caffeinated beverages. That's like the only rule. And I like to stay up late and work when the world is quiet. And so, No, Lauren and I've been going back and forth

on the conversation. Like, I like to get up early when the world's quiet. She likes to get up late, but I don't think there's a right or wrong. I think it's like whatever works for you as an individual.

And what I've learned over time is you can't stifle creativity and if that's when she gets creative if it's late at night. You told me I have to get out of the bedroom though. Well, there's a difference. I said like, it's hard to sleep with the keys

like clicking next year. And I don't know if she's got like giant fingers or something. It's just slamming these things. Last night I was up until like 3am, which is probably a bit excessive. but I totally understand what you're saying. It's just silent at night.

And there's something about I'm the type of person that like I have to wrap my head around things and I just procrastinate the whole entire day until I absolutely have to fucking get it done and there's no other option. And all of a sudden it's like go time. Super shame. Super shame. I think that happens with all creative people. I think and you can't.

Who am I to stop it? So you were in Tim Ferriss's book. Tribe of Mentors? Or Tools of Type? I was in Tools of Titan. Tools of Titans. Okay, and he's an investor. What is the best advice he's given you that you just always think about?

Oh, gosh. I know. You're like, let me pull out my scroll. Yeah, he's given me so much good advice. It's hard to even narrow it down. I would say he helped me think through a bunch of branding and messaging early on that I don't think I was seen clearly. enough. Tim just has an incredible knack for zooming out and distilling down messages into their most powerful form. So when he first invested, we spent a bunch of time kicking around, you know,

how do we talk about trades? And I think some of the insights he shared were not just the insights he shared, but the questions he asked me about our brand really stimulated my creativity and allowed me to stimulate the creativity of my team. His questions, man. Yeah, right? He goes super deep with questions. He's a master at questions. He really is.

What are two resources? It can be anything that you continuously look to. It could be anything. It could be like, or not even speech, people, anything. Blog, book, podcast, anything. Or even a quote, just something that you look to constantly in life, to get inspired or to get motivated. I'm really into a lot of artists.

and like historical figures. I look to Frida Kolo all the time. She was such a unique woman with her, with a really unique story and lived really honestly and bravely in her truth. So I get really inspired by her. And then also I have just such a phenomenal set of investors and advisors that I keep in touch with and learn from all the time. And they've really,

they've really shown me how little I know. So when you get to hang out with people who are in their 60s and have done what you're doing 50 times over and have been really successful at it, it's incredibly educational and also really humbling. And so I like my older, more experienced advisors a lot, and I draw a lot of humility and learnings from my relationships.

What's that old saying? It's like when a man with money, meets a man with experience we use a woman in this term the man with the man with the money ends up getting the experience and the man with the experience ends up getting the money woman yeah it could be I also heard one early on

that really served me well when you want money ask for advice and when you want advice ask for money that really works it's a great thing especially with early investors like you don't go in and say hey I need money you go in and say hey I'm working on this thing and I've got a few problems that I'm

trying to solve, what are your ideas? Because until an investor feels engaged and part of it and like they can contribute to solutions and to the vision, it's hard for them to get excited about putting their money in. That's fantastic advice. A lot of people don't understand that a lot of the time it's not about the money or the check. It's about do they feel passionate? Do they feel excited? Do they want to be a part?

Like, you know, for a guy or a venture group or whatever that has that type of the funds to invest, how interesting could writing a check be? Right? They have to be passionate about something. I think a lot of people make a mistake where they go in and they say, you know, you're going to write me this check and I'm going to give you this money back. And it's like they're already doing that on their own, which is why they have the money in the first place. Yes. You have to demonstrate that there's going to be a return on their investment. That's sort of the table stakes. But in my experience, the best investors are the ones who believe they have some unique perspective or value to share with you that's going to help you accelerate your business. So, When you think about who you're going to meet with or talk to, it's like how do you leverage their unique experience or expertise to help build your business? Because that's when an investor gets excited. They're like, I think I can make a return on this. And also some of the hard one knowledge that I've developed is going to be a competitive advantage in this business.

That's interesting that you say that because you were talking to me before we started podcasting about achievement and how sometimes people think when they achieve certain things, they feel fulfilled. And I was saying, oh, yeah, that reminds me of Tony Robbins. And Tony Robbins says that the best part of life is contribution. So as an investor, it would make sense that they want to contribute as opposed to just write a check. Completely, completely. I think there's, we were talking about this earlier. There's like a, when you're ambitious and you're starting, it seems like once I hit certain benchmarks of success, I'm going to be like,

I made it. I feel amazing. and at least in my experience, and I've heard other people say this, when you actually get there, it's oddly less fulfilling than you would have expected. And then it turns out that the only thing to do, at least for me, that ends up being fulfilling, is to take the knowledge and the experience that you've been lucky enough to access and use it to make a contribution to other people. I love it. And we read in your bio that it says that your team is so, important to you. Can you elaborate on that? Yeah, totally. When I started the business,

I didn't consider the part of leading a business in which you become an employer. And what a great responsibility that is to the people who work for you, to society. You know, you're shaping the work experience of a large number of people and whether you, you know, treat them with dignity and respect, compensate them fairly, et cetera, starts to become, at least for me, it became really central, really important. And we really strive, even though we're crazy startup, and we're always running really fast, and there's always so much work to be done. We do our best to make sure that we're being really fair to our team. And then, I mean, there's nothing more rewarding than watching them grow and excel and achieve. So I think we've worked really hard to create an environment

where they could do that and then seeing it happen is just the ultimate well we love sam and ashton sam and ashton who were who were among the very first here we've been in in business as tradesy for almost six years now um and sam and ashton both came in like the first year or so and they got me watermelon jerky when i came in here do you remember that i'll never forget that they had the watermelon jerky what's watermelon jerky oh my god you got to try it what it's it's So good. It's like, so basically it's one ingredient and it's dried watermelon and there's nothing else in it. And it's in jerky strips and you get it.

And it tastes like fruit snacks, but all it is is just dehydrated watermelon. That sounds amazing, although not as amazing as what I thought it was, which was beef jerky watermelon flavor. That sounds good. That sounds good. I could get on board with that. That's either. Yeah. It sounds good. Watermelon glazed beef jerky.

What is some bad advice? You've heard along the way. We've talked about good advice. What's something that you're just like, no. Oh, there's so much of it. There's just so much of it. Where do we start? And how do you navigate it?

Knowing what you know now. Obviously, it's got to kind of put yourself back a little bit. You're going to take yourself back to a different time. Oh, gosh. I mean, I will say in the, I feel like maybe I've mentally blocked it, but in the early stages, especially you'll get a lot of bad advice. And the, how do you discern it? It's really hard.

I think it's important to be constantly soliciting feedback and advice from everyone you meet. Like if you're an entrepreneur and you're not pitching to strangers on the street, like you've got to do more of that. All the feedback is valuable, but you will get what I think of as feedback whiplash, where two seemingly competent, you know, smart people will tell you to do the exact opposite thing. And I don't have a miracle answer for how to be. to deal with that. I think that staying in touch with your own intuition is very important and

hard to do when you're getting a lot of advice, but doing that matters. And then remembering that there are no absolute truths. You know, nobody who's giving you advice has a crystal ball. If they did, they'd be a lot richer and probably not hanging out with you. But it's also important not to just ask your mom or your dad or your best friend. Totally. Get out and solicit all the feedback you can find and then maybe sometimes there are patterns in the feedback where you go gosh four people said this now maybe I should really listen to it um sometimes something will just resonate with you and you'll kind of know it's true and other times advice will feel a little wrong to you and I would say the only the best you can do is to listen to that and to keep to do something whether it's meditation or

exercise whatever you do that keeps you in touch with you um and and keep tuning into your intuition and trusting it doesn't mean it's always right it just means you don't you don't have any other way to navigate it. And I think that doesn't always need to be when you're, I think it can also be while you're evolving the business or the platform. For example, we'll use this podcast, for example, when we started, it was definitely a little rough around the edges. Lauren and I were not the best. We're still, still, yeah. Your middle name was interrupt. Yeah, still improving. But a lot of what we did to get feedback was, didn't ask, you know, people around us. We asked the listenership and said, what do you guys like? What do you dislike? And, you know,

at some points it was painful and like, oh, that sucks. It feels like a punch in the stomach. But taking that feedback and saying, okay, like 10 people are saying the same thing. Yes. Let's address it. Yes. I want to end this on a positive note. What does success mean to you?

I heard a quote once that has always stuck with me, but I'm not going to attribute it well. So someone, some mystery person said, the measure of your success is not. how much money you make or how much power you get when that window of opportunity opens for you. The measure of your success will be when that window of opportunity opens, how many hands can you grab to pull through with you? And I think for me, that's the measure of success. If I can look around the world and see that I had a small part in helping other people get closer to what they want, that's really all there is.

You'll feel fulfilled. Yeah. Yeah. Where can everyone find Tradesy? Pimp yourself out. TradeZ.com on the interwebs. But I highly recommend that you download our apps for iOS or Android. We're just Tradesi, T-R-A-D-E-S-Y in the App Store, unless you hate saving like 90% on designer clothing,

in which case in fashion, then don't download our app. And I would also recommend that everybody, think about becoming a seller. You probably have some stuff in your closet that another woman would value or want. And selling is like a miracle. It's like you're getting money for things that we're just sitting there. And you can use it to shop again. Or to start your new business.

Or to start your new business. We have women who are selling on Tradesy in order to fund their businesses, which I think is just such a cool. The last time we met when we came here, there's women that do this full time. Oh, yeah, yeah, yeah. And really, like, they're able to quit their day job. jobs and like fully do this whole time totally i think we've talked about that in the past on this podcast that's amazing yeah i think so yeah we had a mom and daughter whose house was in foreclosure and they used um their great fashion sense to go out and source like under underpriced clothing and um outlets

etc and then resold at a profit on trades and they were able to keep their house wow that's amazing super cool that is a cool story i know i need it's great instagram at truble um instagram at Trade Z, T-R-A-D-E-S-Y. You could also follow me. I'm real boring, but it's just my name at Tracy Denunzio. And I want to tell the audience, too, I am a seller on Trade Z. I've been a seller on Trade Z for three years, and I have my own online store. It's under Lauren Everett's, right?

Okay, I just want to make sure. And it's a lot of clothes that I've worn once that are really cute. Amazing. Yeah, so check me out on Trade Z too. So if you go to the site or the app and you type in Lauren Everett, your closet will come up. I love it. How can we get Michael to have a tracy situation? His closet looks like.

Probably not as much. You need something. We don't officially have a men's category yet, but we find that a lot of our women are listing their men's stuff anyway. So we're going to launch a separate men's category soon just so that everything's in the right place. But you can list already. Please, can you do something with the men's things? She's going to start offloading my stuff. No, your closet is so absurd.

I mean, it's just. I got a, yeah, I guess. I've never seen someone with so many boots. I like boots. I start taking things slowly and bringing it like, and like to like give to my brother. He doesn't know. No, I do notice. Like, where's my boots?

And I'm like, babe. I noticed everything. I'm like, that was my favorite pair and it's gone. His voice gets like 20 octaves higher though. And he's like, where's my boots? All right. Let's not make this about me. Thank you for coming on.

That was so fun. Thank you so much for having me. guys I'm going to do a giveaway for Gary V's book before I go. All you have to do is tell me about your blog or business on my latest Instagram and I will pick two of you to win crushing it by Gary V. Like I said, I'm featured in it. The Skinny Confidentials featured twice, which is super exciting. Just leave your business or your blog on my latest Instagram. I can't wait to see what you're all about. Also, do you want to get a short email from me? Tipsy Thursday is a quick email, kind of like a TSC app or teeth with lots of value that includes five tips from me.

My favorite song of the week show, book wellness tip, random tricks, and obviously lots of easy beauty hacks. To check it out, just go to the skinny confidential.com and click Lauren Everts and then subscribe. Drop your email in the box and you guys will get the next one. It's always something different and fun and fresh. Lastly, if you rate and review the podcast, make sure you screenshot it. Email it to ask Lauren at the skinny confidential.com and we will send you my five top secret beauty hacks straight to your inbox. Thank you guys for listening.

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