Tracy DiNunzio on Resilience, Raising Money, and Guest Hosting the Pod

Summary

Money Rehab with Nicole Lapin: Tracy DiNunzio on Resilience, Raising Money, and Guest Hosting the Pod

Released on December 2, 2024

In this insightful episode of Money Rehab with Nicole Lapin, host Nicole engages in a heartfelt and inspiring conversation with Tracy DiNunzio, the formidable founder and former CEO of Tradesy. The episode delves deep into Tracy’s journey from an art student to a successful entrepreneur, her resilience in overcoming personal and professional challenges, and her evolving role in the financial and business landscape. Below is a detailed summary capturing the key discussions, insights, and memorable moments from their dialogue.

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A Deep Friendship and Mutual Respect

Tracy DiNunzio opens the conversation by expressing her deep bond with Nicole:

“[01:14] Tracy D'Annunzio: ...we are really good friends. Yeah, it's true. People do say this. Oh, they're my sister or they're like my bestie and it's kind of hyperbole. But this is not hyperbole. You're my person.”

This highlights the foundation of trust and camaraderie that underpins their discussion, making the conversation both personal and genuine.

Nicole’s Entrepreneurial Success

Tracy admires Nicole’s transition from fine arts to founding and scaling Tradesy:

“[03:56] Tracy D'Annunzio: ...you are truly the most brilliant one that I've ever met in my time in doing business things.”

She reflects on Nicole’s ability to attract high-profile investors despite lacking traditional business credentials, emphasizing the authenticity behind Nicole’s success.

From Art to Business: A Bold Transition

Nicole shares her unconventional path from being an art student to creating a thriving business:

“[05:07] Tracy D'Annunzio: But how did you even think to start getting into that space? Because you started as an art student. You are a beautiful painter, so talented...”

Nicole candidly discusses the challenges of shifting careers, especially without prior business experience, underscoring her determination and adaptability.

Overcoming Health Challenges: Living with Spina Bifida

A significant portion of the conversation centers on Nicole’s personal health journey:

“[08:35] Tracy D'Annunzio: ...I was born with spina bifida. It's a birth defect where the bones in the spine don't fully form...”

Nicole delves into the complexities of living with spina bifida, the numerous surgeries she underwent as a child, and the ongoing management of chronic pain. Her resilience in balancing health with building a business is both humbling and inspiring.

“[12:25] Tracy D'Annunzio: ...most People don't make it out of childhood with spina.”

She highlights the advancements in medical science that have improved the prognosis for individuals with spina bifida and shares her proactive role in research and community support:

“[14:58] Tracy D'Annunzio: ...I have gotten involved in the community.”

Building Tradesy: Fundraising and Scaling with Limited Resources

Tracy discusses the strategic aspects of building Tradesy, especially the challenge of raising substantial capital:

“[04:25] Tracy D'Annunzio: Raised how much money? [04:27] Tracy D'Annunzio: I raised $150 million of venture capital over about a decade...”

Despite having the smallest budget among her competitors, Nicole successfully scaled Tradesy by securing investments from notable figures like John Doar and Richard Branson. She emphasizes the importance of confidence and energy in fundraising:

“[25:36] Tracy D'Annunzio: ...the biggest thing you need to fundraise is confidence. And if you don't have confidence, you need to have the ability to fake confidence...”

The Mask of Success: Concealing Disability in Business

Nicole opens up about her initial reluctance to reveal her disability in the business world:

“[20:23] Tracy D'Annunzio: ...you made a very clear effort to hide the fact that I had a disability...”

She recounts the pressures of maintaining an image to attract investors and customers, and the eventual relief and support she found when she chose to be transparent:

“[22:04] Tracy D'Annunzio: ...it was extremely competitive. And I'm very proud of how you won...”

Transition to Angel Investing and Financial Wisdom

As Nicole transitions into angel investing, Tracy shares her observations on Nicole’s investment philosophy:

“[28:14] Tracy D'Annunzio: ...I write little checks into promising companies, mostly with founders who I really believe in...”

Nicole looks for founders with determination and a "chip on their shoulder," viewing these traits as assets rather than liabilities.

Personal Finance Lessons and Breaking Down Complex Concepts

Tracy reflects on how Nicole’s expertise demystified the complex world of fundraising and business finance for her:

“[24:14] Tracy D'Annunzio: ...you break this crazy world that can be a black box down into us speak.”

She appreciates Nicole's ability to simplify intricate financial concepts, making business fundamentals accessible to anyone willing to learn.

Behind the Scenes: Nicole’s Pregnancy and Guest Hosting

Towards the end of the episode, Nicole announces her impending maternity leave, passing the hosting duties to Tracy:

“[33:25] Tracy D'Annunzio: ...I would love if you could impart some of this wisdom and knowledge to our listeners while I am doing a baby thing.”

Tracy enthusiastically embraces the role, sharing anecdotes about their friendship and Nicole’s impending parenthood, adding a personal and lighthearted dimension to the episode.

Competitive Landscape: Tradesy vs. The RealReal

Tracy introduces Julie Wainwright, founder and CEO of The RealReal, discussing the competitive dynamics between their companies:

“[37:00] Tracy D'Annunzio: ...Julie Wainwright, who was the founder and CEO of the RealReal... we were neck and neck.”

She narrates the evolution from fierce competitors to mutual respect and friendship, highlighting the collaborative spirit that now exists in the luxury fashion resale market.

Closing Thoughts: Embracing Transparency and Authenticity

Nicole and Tracy conclude with reflections on authenticity in business and the importance of showing one’s true self:

“[40:11] Tracy D'Annunzio: ...we were like born in the bleachers in the alleyway...”

Nicole reinforces the value of transparency and the strength found in overcoming personal adversities, encouraging listeners to embrace their authentic selves in their financial and business endeavors.

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Notable Quotes:

• Tracy DiNunzio on Friendship:

  “[01:14] ...You're my person.”

• Nicole on Fundraising Confidence:

  “[25:36] The biggest thing you need to fundraise is confidence. And if you don't have confidence, you need to have the ability to fake confidence...”

• Tracy on Overcoming Defeat:

  “[27:01] I felt like my business was an extension of me, for better or worse.”

• Nicole on Authenticity:

  “[23:46] ...you went to that playing field with like hands tied behind your back and then a literal hole in your spine and you still won the game.”

• Tracy on Investment Philosophy:

  “[30:44] ...when you hear founders say, oh, I'm not like a math person...”

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This episode of Money Rehab offers a profound exploration of resilience, the intricacies of fundraising, and the personal strength required to navigate both health challenges and the competitive business landscape. Tracy DiNunzio’s candid conversation with Nicole Lapin provides listeners with valuable insights into building a successful business while staying true to oneself.

Transcript

[Nicole Lapin]

I love hosting on Airbnb. It's a great way to bring in some extra cash. But I totally get it that it might sound overwhelming to start or even too complicated if, say, you want to put your summer home in Maine on Airbnb, but you live full time in.

[Tracy D'Annunzio]

San Francisco and you can't go to.

[Nicole Lapin]

Maine every time you need to change sheets for your guests or something like that. If thoughts like these have been holding you back, I have great news for you. Airbnb has launched a co host network, which is a network of high quality local co hosts with Airbnb experience that can take care of your home and your guests. Co hosts can do what you don't have time for, like managing your reservations, messaging your guests, giving support at the property, or even create your listing for you. I always want to line up a reservation for my house when I'm traveling for work, but sometimes I just don't get around to it because getting ready to travel always feels like a scramble so I don't end up making time.

[Tracy D'Annunzio]

To make my house look guest friendly. I guess that's the best way to put it.

[Nicole Lapin]

But I'm matching with a co host, so I can still make that extra cash while also making it easy on myself. Find a co [e-mail] Host, I'm Nicole Lapin, the only financial expert. You don't need a dictionary to understand. It's time for some Money rehab.

[Tracy D'Annunzio]

Ah, Tracy D'Annunzio, Nicole Lapis, welcome back to Money Rehab. This makes my heart so happy because you and I talk for hours a day. I don't even know how we find that time because I usually have no time. But we're on the phone and I see it like two hours or I know we're at each other's houses and we talk for so many hours about things.

Sometimes when I put you on hold, I'm taking a quick shower. I just thought you should know. Headphones smell.

Yeah, I definitely have gone to the bathroom when we've been on the phone.

That's how you know you're really good friends.

We are really good friends. Yeah, it's true. People do say this. Oh, they're my sister or they're like my bestie and it's kind of hyperbole. But this is not hyperbole. You're my person.

I married you.

You officiated my wedding. Yes. And you encouraged this large lunch that I'm holding.

Yes.

[Nicole Lapin]

Currently in my belly.

[Tracy D'Annunzio]

Yes. I did encourage it by getting a little too drunk at your birthday. Dinner and telling you and the mister to get to it. And I didn't think you would listen to me. And here we are.

And here we are. And we have an announcement. We do, but we have several announcements. But first, I want our listeners to get to know you in a way that I know you. And during our many hours of discussions, we talk about everything. Boys, bowel movements. I'm trying to think about the third.

Oh, okay. I didn't know we were going.

We talk about the whole spectrum. We also talk a lot about business. And you have taught me so much. And I am so in awe of everything you've done and how you've done it. Because when people talk about being quote, unquote, self made, oftentimes it's bullshit. Oftentimes they started with $5 million. So getting $6 million is not really self made.

Yeah, yeah, we do see a lot of that. I've been, like, shocked as I've made my way through the world and gotten to know more and more successful people. There's like a culture in the US where everybody swears that they're a rags to riches story, that they started at the bottom. And then you get to know people more and more. And it's not always true. Interestingly, it's totally the opposite. In Europe. When I went to work for a while in Europe because I sold my company to a French company, I would say, oh, yeah, and I don't come from this world. I had to work my way up and people would be like, oh, oh, it's okay. So, yeah, that plays differently.

[Nicole Lapin]

But you really did.

[Tracy D'Annunzio]

And the more we've gotten to know each other, I'm truly in awe of everything you have accomplished and how you did sell that company. We can say the big headline. You sold your company for nine figures. What was the we?

I'm not allowed to disclose, but you are free to speculate. It was a nice outcome.

And that company, Tradesy, that you founded and were the CEO of and saw death in its eye many times.

It wasn't simple.

Raised how much money?

I raised $150 million of venture capital over about a decade to fund the.

Growth of the company from huge investors. John Doar, if people don't know who that is. Huge Silicon Valley investor Richard Branson. Yeah, your cap table was pretty sexy.

Yeah. I got really lucky because I really started without having any connections and then somehow managed to get some of the most storied investors in Silicon Valley and beyond to put money and time and effort into my business. And I learned so much. Getting to work with people like that was like I was pinching myself the whole way through.

But how did you even think to start getting into that space? Because you started as an art student. You are a beautiful painter, so talented. You went to school for fine arts, which, by the way, that and, like, 350 will get you a latte.

Yeah. Oh, no. You're, like, so unemployable if you go to school for fine arts. It's crazy. Like, it's a. It's worse than not going to college, I think, in terms of getting an actual job. I went to art school. I always wanted to be an artist. My wonderful parents encouraged me to do that. They were like, whatever makes you happy. But as I was nearing 30, it became clear to me that making a living as an artist was going to be very risky and very challenging. And I was tired of not knowing if my work was good, because you can make beautiful art and, like, it still won't sell sometimes. And so I turned my last art project into a business, but I had no business experience. I had never worked at a company or done business before.

[Nicole Lapin]

You've turned out to be.

[Tracy D'Annunzio]

And I've. I've met many a business person, entrepreneur, and you are truly the most brilliant one that I've ever met in my time in doing business things. I think about little Tracy a lot. Like, I love her so much.

[Nicole Lapin]

I love you so much.

[Tracy D'Annunzio]

But I think about. I didn't know her, and she. I can just imagine growing up in Long Island.

Strong Island.

Strong island, yeah. And sometimes you do go into the accent.

It comes out when I'm drunk or angry, and I don't know how I lost it, but I do know that I. There's one video of me in high school where I clearly had the accent super heavy. It just faded over the years, but.

Faded into this, like, stunning old Hollywood voice that I truly can listen to forever and ever.

I also have been told that it puts people to sleep. And pretty much every relationship I've ever had, my partner, if we were talking at night, would just kind of doze off and be like, but your voice, I can't help it.

It's so good, though.

Thank you.

You have a face for tv, a voice for podcasting. You have it all. But take me back to baby Tracy.

I will. But I want to say one thing first about the voice. I don't think I did this consciously, but when you're a woman in business and you don't have credentials and you want to be taken seriously, Every single thing matters. And I do think that probably over time, I evolved my voice to be calmer and deeper. Not to compare to Elizabeth Holmes, but, like, I understand why she did that, because it's a little bit less feminine and a little bit more digestible for the men who write you checks that allow you to build your business. It wasn't conscious, but I feel like that's how my voice got. Cause everyone says, oh, you sound so calm. And I'm not. But I know that I can put that out.

I know you're not. It's so funny because it's such a poker voice.

I guess I have a poker voice. I do. I have a poker voice. And it's weird. Cause the more stressed out I get, the calmer the voice gets. So, yeah, it's okay. It's cool. It serves me.

Yeah, it's definitely served you. And I want to hear more of your voice, which is a tease for what we'll talk about at the end of this.

Yeah. Okay. So take you back. So I grew up, like you said, on Long Island. I was an only child. I didn't know if. In Long Island. On Long Island. Depends. If you're from there, you say one or the other.

What do you say if you're from there on.

You say in Long Island.

Okay.

Yeah. And if you're not from there, you say on Long Island. I don't know why.

Interesting. It's, like, in line online.

Totally. And we say online for when you're waiting in line. We also drive on the parkway, not.

The freeway, and park in the driveway.

But I think everyone parks in the driveway. So that's not unique to Long Island. But, yes, we do all those things back home. So, yeah, so that's where I grew up. And I was the only child. And on one level, you could just say, like, normal childhood. Both of my parents really, like nice, normal people, grew up in a little house that was like a square with a triangle on the top of it. But I did have one thing that was different or unusual. That was tough. So I was born with spina bifida. It's a birth defect where the bones in the spine don't fully form. So the nerve column where all the nerves are that make your stuff work is exposed through a bunch of sort of medical miracles, you could say. I was able to receive a few operations at birth, and when I was a baby, that helped me be able to walk. And my parents laughed because they. I guess they sent my parents home from the hospital with me, and they Were like, we don't know, anything could happen from here. And I never sat up. I just went from laying down to crawling everywhere. And they were like, we think she's going to be okay, but she's weird. She doesn't do things in order. Which ended up being my whole life. And so, yeah, so I grew up spending a lot of time in hospitals and doctors offices. I had more surgeries than I can count to address all kinds of different problems that happen from spina bifida, mostly related to my legs and feet and just trying to preserve my ability to walk. I had spinal surgeries that were very risky and complicated to try and alleviate, like, nerve issues in my bladder and my hips. And so my life as a kid was, like, going between phases of being normal and then going back into a hospital phase where we wouldn't know if I was going to come out of the next surgery able to walk. And there'd be a lot of, like, pain and difficulty and big risks and just, like, trauma. Right. And people talk a lot about trauma now. And I've known my whole life that I had a lot of childhood trauma. So I've been working on it for a long time. And, yeah, and then I still have to do a lot, like, medically to stay walking. And I have a lot of kind of chronic pain and areas of weakness that I have to manage. So when I think about building my business, that was my second job. My first job has always been, like, managing the body I was born in. And when people asked me about being a CEO, I didn't used to talk about this. But what I always wanted to say was, like, it's easy. You should see my first job. My second job is really easy compared to my first job. But really both jobs, not that easy. So that's the other things happened. Like, I went to summer camp and I had a first love, and I had a lot of the normal milestones in life. And I was like a big partier as a teenager because I had to let all that energy out. But I did deal with a lot of medical challenges.

I didn't realize how serious spina bifida was until I think I was dating this brain surgeon for four minutes, and you asked me to ask him a question about spina or get a specialist or something like that. And I remember telling him about you and how amazing you are and that you have spina. And he's like, how old is she? And he thought you were a kid or something. And it was only then that I realized that most People don't make it out of childhood with spina.

Yeah, the prognosis isn't, well, it's getting better. So before I was born, historically, most people born with spina bifida did not live into adulthood. And if they did, they were often institutionalized, lived limited lives, not necessarily because of their limitations, also because society didn't really make accommodations for people with disabilities back then. So it was a pretty tough thing to be born with. Around the time that I was born, there were some surgeries developed and interventions developed that would help people live into adulthood and maybe get some mobility. And since then, there have been a lot of advances. So today a lot fewer babies are born with it. Those who are have a lot of options for surgery, in utero interventions and surgeries all through childhood that are much better than when I was younger. But for me and the other people of my generation who have spina bifida were medical mysteries in a way, because nobody ever did research on adults with spina bifida. So every doctor I go to has never seen an adult with spina bifida. So I have to be my own doctor. And I always was like, even when I was a kid, 8 or 9 years old, I used to go to the public library after school and read medical journals on microfiche and try to understand what my doctors are saying and what the decisions were, because it was all like a mystery. So, yeah, it's serious. And I mostly think I've just been lucky. But I have also worked really hard to train myself to walk and to try to keep a really positive mental outlook, because that's a big part of dealing with it too.

But you're in this group or several groups where you talk to. There's not that many adults with spina bifida. Right now you're in some of these chat rooms and you guys talk about symptoms. Ongoing.

Yes.

Not walking, not being able to go to the bathroom. These are serious issues.

Yeah. I'm involved with a few different groups trying to get research done, trying to create community for people who have spina bifida. And even now I'm getting involved in things beyond spina bifida. Just understanding that there are so many under researched medical conditions where people are living with difficulty that can maybe be solved with technology. And that's just like the entrepreneur in me. I want to use AI and understand what little data exists to help improve life for everybody. I have gotten involved in the community.

It's amazing. I'm no doctor. You'll obviously forget more than I'll ever know about anything medical. You are like my ad hoc doctor.

But I ask everybody's pretend doctor random questions, too.

But it's a neurological disease.

It's like you are generally neurologically compromised because there's a mechanical issue at the part of the spine that's affected. So different people who have spina bifida have different systems affected because it depends at what level of your spine, the defect or deformity or.

It's a hole, right?

It's a hole. And you have to. One thing my mom taught me growing up, being in and out of the hospital is you have to laugh, right? You have to laugh. So we joke all the time. Oh, sorry. I'll be right there. It's just the hole in my spine is acting up. And I have another friend who will go on a really slow hike because I can only hike pretty slowly. And he'll just look at me and be like, why are you still faking it? And, yeah, it affects primarily your neurology. So for me, it's like my calves and my feet and certain muscles in my hips don't get nerve signal, so the muscles in those areas are really atrophied and weak, and I can't feel my feet at all. So I walk using my eyes and my ears to balance. So if you ever want to, like, mess with me, you can just turn the lights off or play a really loud noise, and it'll completely throw my balance off.

But these are things that most people don't think about having to think about.

They don't. Most of the time. I'm very happy with my life. I feel like I cheated a bunch of worse potential outcomes and got to live a very full life and still get to. But every now and then I look around and I'm like, man, everybody should just stop and be really grateful for how you can just walk around and not think about it.

I sometimes look at you or hear your stories about even Baby Tracy going to the library and I'm sure researching on microfilm or whatever it was back in the day to adult Tracy starting tradesy and like, staying up and teaching yourself how to code from being an artist. Like some. I feel like something. What's that movie that's like Invincible the drug Limitless. I feel like a limitless thing happened to you with this because it turned your brain into something truly. You have a Lamborghini between your ears, and it's something that is so unique and it's gotten you so far. But whatever that is, like, you're able to go so deep into to topics that you know nothing about and just teach yourself.

It might just be like a lot of. I mean, when you're young, your brain is such a sponge, right? And most people set their minds to learning whatever you're learning in school. And I just set my mind to learning like medical research and things like that. So I really got to flex those muscles and I was like a voracious reader. So I think I have an ability to learn quickly. When I'm interested in something. I get a huge appetite for information and can process and digest a lot of it, which came in really handy.

[Nicole Lapin]

Hold onto your wallets Money Rehab will be right back. I love hosting on Airbnb. It's a great way to bring in some extra cash. But I totally get it that it might sound overwhelming to start or even too complicated if, say, you want to put your summer home in Maine on Airbnb, but you live full time in.

[Tracy D'Annunzio]

San Francisco and you can't go to.

[Nicole Lapin]

Maine every time you need to change sheets for your guests or something like that. If thoughts like these have been holding you back, I have great news for you. Airbnb has launched a co host network, which is a network of high quality local co hosts with Airbnb experience that can take care of your home and your guests. Co hosts can do what you don't have time for, like managing your reservations, messaging your guests, giving support at the property, or even create your listing for you. I always want to line up a reservation for my house when I'm traveling for work, but sometimes I just don't get around to it because getting ready to travel always feels like a scramble so I don't end up making time.

[Tracy D'Annunzio]

To make my house look guest friendly. I guess that's the best way to put it.

[Nicole Lapin]

But I'm matching with a co host so I can still make that extra cash while also making it easy on myself.

[Tracy D'Annunzio]

Find a co [e-mail] host and now.

[Nicole Lapin]

For some more Money Rehab.

[Tracy D'Annunzio]

And when you were starting Tradesy, you got deep in tech, in business. You didn't. You probably thought like I did the first time you heard ebitda, that it was like an STD or something. Like we didn't come from this world or this language. But when I knew you and you were still at Tradesy, there was a time that you were walking with a gate.

Yeah. So when I started my company, I made a very clear effort to hide the fact that I had a disability. I was very obsessed with it was really important to me that nobody would see that anything was wrong with me.

Why?

Because part of what I needed to do to be successful was raise a lot of capital from investors and hire the best possible employees and appeal to customers of a. It was a fashion company, and I didn't see anybody with a physical disability able to do. I can't say I didn't see anybody, but it just seemed to me like.

You certainly didn't see a woman, right?

I was already a woman without a business background. And now what? I'm going to march into the top venture capitalist office and have an obvious physical disability? Like, it didn't seem like anybody would give me money or follow me in terms of wanting to join the company and take equity and believe in our future if they thought I had anything slowing me down or distracting me. And so I used to, like, go on TV to promote the business, and I would tape chicken cutlet boob things to my legs because my legs are really skinny from the atrophy. But I wanted the shape to look correct to the cameras. And, yeah, I tried really hard. If I really focused, I could not limp at all. So I worked really hard to make sure nobody saw it. And then I worked too hard. Not just at that, but at everything. I was working seven days a week, 24. 7. Like, I overworked myself. I got really stressed out. My health got bad. And part of that was that I was not walking as well, and I had to use a cane for a while. And so I. That was maybe 2019. I started having to tell people that I had something going on, and I thought the world would end. I panicked about this, and I stayed up late nights and I thought about hiring a CEO to replace me because I really had made it in my mind. People would judge me and be disappointed in me and no longer have faith in me. And it was the opposite. I felt like my team and my investors were like, wow, we want to follow you even more. You're like a real human being, and we believe in you even more. But also, it was no big deal. It was like I had made it in my head, like the whole world was going to care. And the number one rule of life is, like, nobody actually cares about you that much. People were just like, oh, wow, that's wild. Sorry to hear. Moving on with my life. But I don't know if I could have been as transparent about it earlier in my career and actually gotten over the early humps to bring on support for the business.

That makes sense. And was it a Wait off when you finally could do it because you never wanted to be treated differently. That was some of the driving force.

Yeah. It was very important to me that nothing ever be like influenced by that so that I could compete on the same playing field as everybody else, whatever. However, they were coming to the field and win on my merits and I don't think it really changed anything.

But you went to that playing field with like hands tied behind your back and then literal hole in your spine and you still won the game.

Yeah, I don't know if I won. My company was very successful. It got very big and then it sold. It was not the biggest company in our category. There were companies that did even bigger and better, but there were also maybe 50 companies that completely failed. And so it was extremely competitive. And I'm very proud of how you won. I just how we play.

I decided who wins here and you won.

Thank you.

When you were going through the building of the business, you and I talk about this a lot as you are now angel investing, you're a board member, you're a consultant extraordinaire. Anyone who does business with you is the luckiest. We talk about fundraising a lot and I find it to be so helpful that you break this crazy world that can be a black box down into us speak.

Of course. It's really fun, I think, to demystify. One of the things that I noticed when I came into the world of building big companies, building venture backed startups, was that there was so much lingo and I initially felt like such an outsider. And then I learned that people were just using big words for simple concepts, which might be a way that business schools get to charge tuition or something, but it's really not that complicated. I think anyone can pretty easily understand business fundamentals and build a great business if they have drive and vision and work really hard. And so I love making it simple because it actually is simple.

So when you were going out to fundraise in the beginning, what did you need to learn?

The biggest thing you need to fundraise is confidence. And if you don't have confidence, you need to have the ability to fake confidence, which was what I had because I felt very unsure and very insecure and very out of my depth when I first started meeting investors for all kinds of reasons. And it just wasn't my world initially. But I was good at faking it, at putting on a bit of a mask and putting out big cack energy. I can tell you a bunch of other things that are helpful for fundraising, but Those are all things you can Google, right? You can look up, like, the standard 10 slide deck that you should have and all of that. But investors are just human beings. And as a human being, when you feel like someone is holding on to a magical secret and they're on a magic carpet ride, you just want to be part of it. And I think your energy when you go in to pitch an investor is so much more important. Like, you have to have your T's crossed and your eyes dotted, your numbers have to foot. Your plan has to make sense. You have to know your business. You have to understand your category, but you also have to walk in like you know the future, and it's so good that you can't even believe you might share a piece of it with these guys. And that's contagious, and that's actually what gets them to fund it.

Did you instinctively know that, or did you go in timid to start?

I wrestled with getting my mask on straight. So I had an investor tell me early on when I was in this incubator program, you feel defeated, and that's. I was the last out of the 10 companies in the program to raise capital. I did feel defeated. I had pitched all the same investors that everybody else had pitched, and nobody wanted me, you know, and everybody else was raising money, and we had a bell that you could ring when you closed capital, and I just wasn't ringing the bell. So I did feel very defeated. And he basically told me, like, he could smell it on me. And I took my business very personally. I felt like it was an extension of me, for better or worse. It's not like a great way to live your life, but it is a great way to put all your heart and soul into your business. So, yeah, I felt really bad every time an investor didn't jump at my pitch, but I got really good at hiding it.

I think I mentioned that you're an advisor board member, Right. So now you're really rich.

[Nicole Lapin]

That's good.

[Tracy D'Annunzio]

So you are an angel investor.

I am.

Because you got a lot of angel investments from people who had exits, and now you're in that position.

Yeah. And it's nice to. I don't write big checks. I write little checks into promising companies, mostly with founders who I really believe in. And I look for the founders who are like, how I was hungry with a chip on their shoulder and, like, very determined, mostly in the AI space. But I have a broad variety of investments.

And now it's so interesting that you see that chip on the shoulder as such an asset and not a liability that you thought yours was.

Totally. Yeah. It's such an asset. Like most founders, CEOs, business builders, people who just overachieve tend to have a chip on their shoulder. And now I'm part of all these groups of CEOs and founders and have gotten to know people really deeply, and it's. We're all a little bit crazy. We all had something that made us feel less than or different or not.

Something to prove.

Yeah. We had to come and prove ourselves to the world. I don't know if that's. Personally, as a human being, I'm looking to move away from that feeling, and I don't want anybody to feel that way. But I do believe that for people trying to build something where it's a very uphill climb, that's good fuel.

I know you've not wanted to talk about this chip on your shoulder, so thank you for opening up to me to talk about it.

Yeah, of course. Only with you. Yeah, I feel like, why not? At this point, I don't feel like I have anything to prove anymore. And if it's useful or helpful, then great. Yeah, I'm happy to talk about anything.

Really? Yeah.

What do you want to know?

You have some really good stories.

Most of the stories are like, me doing dumb and risky things to either get ahead or have fun, and it backfires.

But those are the best stories. Yeah. And I think that you ran this huge p. L. And you got super deep and smart about all of the business terms, and you are a freaking savant and wizard. And you would school these Harvard MBA McKinsey people with on. In cell Z47. There's a mistake. I mean, you're really good at the math and the numbers because you had to be. So when you hear founders say, oh, I'm not like a math person. Somebody does the math number stuff, what do you say to that?

For me, those founders are probably not the ones that I'm going to invest in. All types of founders have succeeded, so you can't, like, rule out or negate any. But for me personally, like, I always viewed my business through the numbers. Right. What else is there in a business? And I had the mental map of all of the mechanics of how money flowed through the various parts of the business. And so when somebody would come up with an idea, I would float the idea through my mental map and see how the money moved through the system and whether enough came through. And that was based on understanding what assumptions drove our revenue. And so when I Meet founders who don't understand what the levers are in their business from a math perspective or a money perspective. I have a hard time having the most exciting types of conversations with them because it's a different lens. So, yeah, that was always just my.

Lens, but it's a different lens. And I learned this when I was at cnbc, even just talking to bond traders versus equity traders. Not everybody in business knows all the things about all numbers and types of business or finance. And so you are super deep and knowledgeable in certain kinds of business and finance. But also when we look at your bank of America account, it's a whole different world. Right? And so I think it's really important to bring that perspective and to also say, no, I don't know all the things, but I have smart friends or have smart people who I can bring in on these topics. And not all business, not all numbers, not all finance is totally equal or the same or you understand it all because you understand one part world.

I was flummoxed by personal finance for a long time. I was so busy building these, like, large, complex businesses with massive P Ls that once I had some money in my own bank account, I really called you and I was like, I don't know what to do. I'm afraid to let any of it go or put it anywhere. And I didn't know the lingo, and it felt very, very challenging to dive into a whole different world where the money, the mental map, and the money map flows a little bit differently. And frankly, I wasn't used to managing money that was mine personally. I was used to managing investor capital. And so it's a different mind frame. When it's your own money.

[Nicole Lapin]

Hold onto your wallets.

[Tracy D'Annunzio]

Money rehab will be right back.

[Nicole Lapin]

And now for some more money rehab.

[Tracy D'Annunzio]

If you don't mind doing me another favor because you've done so many for me already. But I would love for you to tell those stories on this show while I go have a baby when I birth this burrito that's in my belly and guest host for this show and talk about some of these stories.

Yeah, I am super excited to temporarily take over while you bring our bundle of joy into the world. So, okay, we are how far along right now?

We are seven months, we're third trimester.

And you're about to go take off and let me take over?

I don't know. I'm gonna try. But when we were thinking about this and saying, why don't we own this business? Like, we don't have maternity leave. We don't have hr. How am I supposed to. I didn't expect this to happen. I'm 40. What is happening? And so this was not part of the plan. This was not in the business plan.

It was always part of my plan. I don't know what plan you were operating on, but I was planning and hoping for this plan.

[Nicole Lapin]

You did.

[Tracy D'Annunzio]

And you were the first person. You knew that I was pregnant before I did.

I did. You looked pregnant in your eyes. I will never understand. I was like.

I was like, I have to pee all the time. And then you thought you're pregnant. And I said, you think I'm fat.

Yes. And I was like, okay, I'm not going to say this anymore. But you were only like two weeks.

Yeah.

Pregnant. And you were like, no, it's not possible. I wasn't ovulating.

I thought so anyway. Maybe tmi.

But I think everybody knows you're ovulating. Can't hide it.

Okay.

Yeah.

So when we were thinking about what this plan looks like, because it was an unexpected plan, I thought, okay, I probably need a little bit of time to at least birth the child and go from the hospital. And this is a daily show and what are we going to do? And so the first person that came to mind was like, I don't know if we could possibly talk even more. You have more capacity for me in your life. But I was like, it's. Of course it's Tracy, because she's the smartest and she knows all the things that also are a good complement to the skill set and the knowledge that I have. And I learn from you all the time. Maybe sometimes every once in a while you learn from me. I doubt it.

But all the time. All the time. I can bring all of the sort of business and starting a business and getting your ambition for money in order and how to chase that and you really, without you, I would not know how to manage my money at all.

That. That is maybe. No, just kidding. That is definitely not true. But you do have too much money in cash. So just FYI.

Okay. I know.

Which is high class problems and very. And I'm so proud of you.

I'll diversify. I promise I'll diversify.

But I would love if you could impart some of this wisdom and knowledge to our listeners while I am doing a baby thing. I would love for you to take this seat, if you don't mind. And I can't wait. Bring on all the fabulous people and who've been investors in you or I know. You're even doing an interview with your biggest competitor in the space. You alluded to the fact that you didn't win. Yeah, bullshit, you did. But there's your major competitor, the RealReal.

Totally. So I'm bringing Julie Wainwright, who was the founder and CEO of the RealReal. She's a phenomenal entrepreneur. I feel like she doesn't get enough press for how successful she's been. One of the only women who's been the CEO of multiple public companies. Just, she's extraordinary.

But also your biggest rival.

We were direct competitors for years and we like luxury fashion resale. Like we had the two, I think, biggest companies in the category and we viciously competed. And for the first half of that we were neck and neck. And then the Real Real took off and started growing a lot faster than we did. So, yeah, she was on my dartboard for a while, but then we became friends and I'm very excited for her to talk to the money rehab audience.

And you're even a customer now, which you never thought you would do.

I am, I am. Because my company Tradesy doesn't really exist anymore. It got folded into Vesture Collective after they bought us. And I love Vestier Collective too, and I shop on there, but now I'm free to shop and sell wherever.

Yeah, you guys were neck and neck. Yeah, you were number one in the space. Then they came to number one and they. But you were all kind of. It was you guys real. Real Poshmark. Probably like in the team photo.

Yeah, team photo would have been tradesy and the RealReal in the luxury zone and Poshmark and Thredup in the. More like mass market zone. With a special shout out to Fashionphile, which was also a really big company in the luxury zone. But they weren't. We were all part of this era where sustainable fashion and fashion resale became a very hot category and got extremely heavily funded by Silicon Valley venture capitalists. So you could think of it as a decade long race. The way Uber and Lyft were, where everyone was just raising a ton of money and spending a ton of money to grow as quickly as possible without worrying about being profitable. And that era is now long behind us and companies have to operate differently right now. But that was our. I raised 150 million to grow tradesy. It sounds like so much, but out of all four companies, that was by far the least that any of those companies raised. So yeah, so it was a wild.

Era of scrappy $150 million.

Yeah, I made it work. With just this tiny budget while everyone else had big budgets.

But I want our listeners to hear more from you because I've learned so much from you personally. And the stories you tell just remind me that you were not born on third base like a lot of entrepreneurs who are so successful and so self made. I mean, you and I joke sometimes that we were like born in the bleachers in the alleyway. And so figuring that out is the kind of energy and the type of teaching that really resonates with people who want to also break out and want to also learn but didn't go to business school. And you and I are finally at a place where we can be like, yeah, fucking, I didn't go to business school. But that wasn't always the case.

Yeah, I think I almost feel like an obligation, having come to this point in my career and my life, to drop the mask, even though it's hard to do that and actually say, yeah, I had to really work my way up. And yeah, I did it with a disability because I really needed to hear that when I was starting out and I didn't hear enough of it. So I think we just have to show up and say we clawed and scratched our way here and you can do it too.

[Nicole Lapin]

Money Rehab is a production of Money News Network. I'm your host, Nicole Lapin. Money Rehab's executive producer is Morgan Lavoy. Our researcher is Emily Holmes. Do you need some Money Rehab? And let's be honest, we all do. So email us your money questions, money rehaboneynewsnetwork.com to potentially have your questions answered on the show or even have a one on one intervention with me. And follow us on Instagram @moneynews and TikTok MoneyNews Network for exclusive video content.

[Tracy D'Annunzio]

And lastly, thank you.

[Nicole Lapin]

No, seriously, thank you. Thank you for listening and for investing in yourself, which is the most important.

[Tracy D'Annunzio]

Investment you can make.

[Nicole Lapin]

I love hosting on Airbnb. It's a great way to bring in some extra cash. But I totally get it that it might sound overwhelming to start or even too complicated if, say you want to put your summer home in Maine on Airbnb, but you live full time in.

[Tracy D'Annunzio]

San Francisco and you can't go to.

[Nicole Lapin]

Maine every time you need to change sheets for your guests or something like that. If thoughts like these have been holding you back, I have great news for you. Airbnb has launched a co host network which is a network of high quality local co hosts with Airbnb experience that can take care of your home and your guests. Co hosts can do what you don't have time for, like managing your reservations, messaging your guests, giving support at the property, or even create your listing for you. I always want to line up a reservation for my house when I'm traveling for work, but sometimes I just don't get around to it because getting ready to travel always feels like a scramble so I don't end up making time.

[Tracy D'Annunzio]

To make my house look guest friendly. I guess that's the best way to.

[Nicole Lapin]

Put it, but I'm matching with a co host so I can still make that extra cash while also making it easy on myself. Find a co [e-mail] host this episode is brought to you by Progressive Insurance. You chose to hit play on this podcast today. Smart Choice make another smart Choice with Auto Quote Explorer to compare rates from multiple car insurance companies all at once. Try [e-mail] Progressive Casualty Insurance Company and affiliates not available in all states or situations. Prices vary based on how you buy.