She Lost 100 Pounds, Got Into YC, and Raised $15M

I got on the scale and I like immediately started crying. I was 40 pounds higher than I had ever, ever been. My whole life I struggled with my weight. I felt invisible. Ended up losing 100 pounds. When you find yourself completely out of alignment, you don't recognize yourself. It's time to make some radical, radical changes. Dump the boyfriend, quit the job, jump on the flight, and you don't need a backup plan. You'll figure it out. I pitched 149 times and got 149 nos. I remember looking at my mom and, you know, her especially being like Anna. Maybe this isn't working. I did one more pitch. It was Y Combinator, and by some miracle, we got in.

What is Trade?

Trade is a construction payroll, HR, and compliance system built for specialty contractors. In total, we've raised more than $15 million.

What would you say is the question you get the most?

Probably what it's like to be a woman building in construction.

What about the question you don't get as much that you would like to?

How am I doing? No one asks that. How are you, Anna?

Anna Berger, welcome to the MakerPod. Max and I are very excited to have you. You've been a very close friend of ours for a while and you have been through so many, you know, challenges and amazing personal transformations that I think will inspire a lot of people. And so I'm just very grateful that you came on and feel comfortable sharing this story. And yeah, we're very grateful to have you.

So happy to be here. Yeah.

And congratulations on the series, Anna.

Thank you.

Well, cool. So before we get into the present day of where you're at with the company, we love to talk about pre-startup founder Anna. A particular chapter that I think is interesting, which is Anna in corporate America and feeling invisible. Can you tell us a bit more about that chapter?

Yeah, it's— you're in these massive organizations in corporate America, right? I started my career in advertising, working at a few different marketing agencies before going in-house to Marriott International. You're just a drop in the ocean at companies like that, right? But I think at the time, for where I was in my life, that was an environment that I actually felt very safe in, kind of falling beneath the fold a bit and just putting my head down and doing good work.

And did you sort of— did you seek that out? Like, were you looking for that, do you feel like, or was that—

I don't know if I necessarily knew what I was looking for. I had a bit of an identity crisis in college, uh, thinking I was going to be one major, ending up in a different one. And so I was pre-med. Wow. Yeah, yeah, before organic chemistry took me out.

And what happened?

It wasn't ultimately my path, right? I grew up watching medical shows and thought I was going to be the best doctor in the entire world, and turns out bio and chemistry and orgo had other plans for me. So it forced me to take a hard look at who I was and who I was going to be. And so, yeah, I stumbled into corporate America and advertising. Knew, knew I was creative in some way and could apply my organization skills, my creative, like, art skills. But yeah, it's not something I sought out.

What was your favorite ER show to watch?

What was ER? Oh yeah, like the ER, the one and only.

What about Grey's Anatomy?

Yeah. Also, I'm still watching it. Season like 97. I was gonna say, there's 100 seasons of that show. Yeah, we're at season 97. Yeah, but I don't think I've missed an episode. Wow. Yeah.

Did, um, did your parents want you to be a doctor?

I think they wanted me to pursue a traditional career path, and that thought has definitely come up again and again as I've taken a very non-traditional career path. I think the early years were very scary for them as I took this plunge into the unknown. I think that they would have felt more comfortable in something that was more predictable. Cool.

And then you said you failed out of—

Totally.

Pre-med. Okay.

No, like literally at the University of Michigan, they— you're in these lectures that are like 800 people. And so when they announce the scores on a test, they put a bell curve on the board of like lowest, middle, highest in front of everybody. That's how they announce the scores. And the lowest score was a 27. The highest score was a 103, and the median was somewhere in the 70s. And I remember turning to my friend and being like, who is the idiot that got the 27? It was me.

Hell yeah.

Yeah. Crazy. Like, if I'm going to go out, I'm going to go out with a bang, right? Crazy.

And so you're like, this is not for me.

Yeah. I honestly, I didn't even get there, but my guidance counselor did. Right. In the time they were like, this is not— you're not successful here. Right. And it's time to look at other classes and, you know, courses. Right.

How did it feel to hear that?

Obviously devastating when you think of yourself in one view your whole life. And I mean, truly, until I was 19 years old, I didn't consider another path for me other than like going to medical school, becoming a doctor. So for someone to just be like, hey, it's not actually working and this is not what you're going to end up being, you have a bit of an identity crisis of like, then, then what am I? Who am I?

You didn't realize that was what you wanted to do your whole life?

Oh yeah. Never questioned it.

So like if you were asked at 9 years old, like, what does Anna want to do?

Doctor. I would have said brain surgeon. So it's not even like I would have said, like, you know, dermatologist, which, you know, we love our dermatologists these days, but like, never in a million years would I have said, like, startup founder.

Interesting. For me, I used to tell people that I want to be a plastic surgeon, but not because I genuinely was passionate about that work, but because I liked the reaction my parents gave me when I would tell them that.

Sure.

And, uh, for most of my early life, like, I was like, yeah, I want to be like a surgeon, plastic surgeon. And there was no actual reason for wanting to do that other than just like to get external validation. Do you feel like there was external validation you were chasing there, or did you genuinely want to like help people?

Now that you say that, I think that that resonates with me a lot. I had an older brother who was an absolute superstar and he still is, right? But at the time I was 4 years behind him in school and he was the valedictorian of his high school. He went on to go to Harvard University, spoke 8 languages. He was like a certified genius, right? And so for me, there was definitely a part of me that was trying to like, you know, puff my chest of like, who am I going to be? I'm going to be this big doctor, this really successful brain surgeon, right? That felt like I was staying competitive with him in some way.

Do you guys still feel competitive?

No, not at all. We're just doing such different things now. I feel like I'm really in my lane and he's in his and we have such different skill sets. He's very intellectual. He's so book smart. He always has been. I think I have him beat on like the people skills, right? The street smarts, the business acumen, being able to read a room before you walk in. I think that's where our skill sets totally split in the road.

Cool.

Yeah.

So you, so you fail out of pre-med.

Yeah.

You kind of— it sounds like you go on, you get this job at Marriott. Is that obviously years later after you graduate? How long were you there?

I was at Marriott about 3 and a half, 4 years, something like that.

And, you know, we've talked about this, but you said that also you were going through some like serious, like physical challenges, right? Maybe you want to talk a bit about that.

Yeah, I— my whole life I struggled with my weight. I was someone who was, you know, even in kindergarten, I was the biggest kid in class, right? It was something that followed me all the way into my late 20s. And it was something that I was never complacent with. It was always frustrating. It was always really hard for me. I felt like I would truly— I would work out every day, I would eat lettuce and chicken, and I— my body was gaining weight. And it was always a very frustrating scenario for me to be in. And I, in my 20s, I decided to like, you know, I, I chose to do something about it, right? Like, I think I waited for my, my parents to intervene in my teens, and they threw so many resources at me to try and help, but clearly there was something larger going on. So mid-20s, around 26 is when I discovered I had something worth dealing with. And so that's really when I went on this like total, total health journey, ending up losing 100 pounds, which was transformative over a bunch of years. It wasn't drastic. It wasn't overnight. A lot of people didn't even notice, right? At least at first. But it's something that completely changed the course of my life.

And you were sharing the story about Rent the Runway. Do you want to share that?

Yeah, nuts. I mean, first of all, shout out to Rent the Runway, like one of the best startups out there, really. The way that they kind of came in and just blew up the fashion industry, really impressive. Something I like, I was inspired by at the time. But yeah, Rent the Runway. For like 2 or 3 years, I wasn't buying clothing. I was renting clothing. And in this period of time where I was really lost with myself, I knew I was working jobs that weren't aligned with who I was and what I wanted to be when I grew up. And I was caught up in like the drinking scene in New York, right? And there's not much to do but go out and drink and party here, right? And so I really fell into that in my 20s. I'm renting all these clothes, right? And I'm not buying anything. And I slowly realized like I'm bigger than I had ever been, right? 26 years old, I look in the mirror, I don't recognize myself, right? And I— it wasn't like I was outgrowing my clothes. I just kept going up a size, right? And it was this really slow leakage that had happened where there was one really like kind of big like wake-up call that I— it was a health scare. Like I knew I had to do something about it and take, take control of my body. Yeah.

What can you tell us about the health scare? What happened?

Yeah, I mean, I went to the doctor. It was like a routine checkup. And you know how they always ask you to get on the scale? And I got on the scale and I like immediately started crying. Like I— it was a number I had never seen before. It was 40 pounds higher than I had ever, ever been. And I was a serial yo-yo dieter. Like high, low, crash, up and down my whole life. And I just remember freezing and being like, I think something bigger is going on here, right? Because I, I wasn't, um, I wasn't like totally off the deep end, right, with my behaviors. I've always been pretty disciplined, um, so I knew that there was like a larger thing going on.

And did you just in that moment go like, all right, everything I've been doing, like throw it all? Because it sounds like you've been trying to do things. So like, what was the— how did you— what— how did you basically like say, okay, this is going to be different this time?

I knew I couldn't do it by myself anymore. If I had been trying to do it by myself, it was clearly past that point. And so like the next day I was in the doctor, right? Just— and I got every blood test done. And, you know, they're like, it, it, it went past me, right? It couldn't be something that, you know, I'll eat 600 calories and go work out for an hour and a half. Like that wasn't working, right? Because that's what I was doing. So I knew that there needed to be a bigger step beyond that. And I think definition of insanity, it's like doing the same thing doing the thing again and again and expecting a different result. I think that was one of the very many moments in my life where I've kind of just been like, let's burn it down and start over. Whatever.

You blew up your life.

You have to every once in a while when you find yourself completely out of alignment. You don't recognize yourself, right? You have to totally burn it down and start again.

How many times have you done that in your life?

4, 5 times. Yeah.

How much time do we have?

Yeah. I— it's the scariest and also most empowering feeling in the entire world to know, like, at the end of the day, I've got me and I trust me and my instinct and gonna jump and see where I land.

So you realize that you need to make this change?

Yeah.

Then what?

I started a really intensive plan, right? I had to start taking insulin medication. Right? So there was— there were bigger things happening. And something that I should have been taking since I was 10, right? And I wasn't on it for my whole life. Like, I had an insulin resistance. And so, you know, started supporting my body with what it actually needs. The same way, like, people with anxiety take anti-anxiety, the people with depression take antidepressants. I was depriving myself of something I actually needed. So immediately started that. I re-centered working out, but in a different way, right? It's not about running on the treadmill for an hour. It's weightlifting, right? It's Pilates. It's doing movements that feel more organic and don't just put your body into a state of stress. Um, and yeah, of course, like changing the way I eat.

Oh wow, that's amazing. Um, I think so many people, uh, struggle with that sort of ability to blow up their life and actually make meaningful change. The fact you're able to lose over 100 pounds, you said, is crazy.

Yeah.

How long did it take?

The large chunk of it, no pun intended, um, was probably over 3 years.

Okay.

Wow.

And then where were you at socially? Like, what does your social group look like at this point? Does it change over these 3 years?

That's a hard thing, right? Because you're— everything about you is changing through this. I'm so lucky I've had the same like 10 best girlfriends since I'm a child. And so—

10?

About that. Yeah.

That's a lot of best friends.

From different phases, right? They're like my sisters, right? From like, you know, nursery school all the way through to like college that like I've had these people in my life forever. I was watching all of them get married, right? I watched all of them go through these like transformative life moments and I was like radically focused on fixing Anna. Um, mind, body, and soul. Mind you, this wasn't— I don't want to make this all seem like I had a problem with my body and that was the root of it all. Like, I was, I was lost. I was in a career that wasn't fulfilling. I was, was hiding there because it felt good. Um, I mentally was insecure. I wasn't dating with intention, and when you don't date with intention, you get caught in really bad situations. Um, it was all off. Right? And so this 3-year transformation was me coming back to Anna, like, who am I? What am I looking for? What do I want to do with this life? Uh, it was a, a great recentering, and a lot of that was like a change to my social scene, who I went out with, how I spent my time. Um, you definitely lose a lot of people that fall out of alignment with you.

Sure.

Maybe talk about like, how did your life change for the positive, and how did it change for the negative?

I think my life changed predominantly in a positive way. I think for me, the world started seeing me as I always saw me, which is, you know, vibrant, a lot to offer, a lot of love to give. I think people started listening to me more. And I don't— again, it's important to say I don't know if that was in my head or if that was like reinforced via society, But when I lost the weight, my career took off. And I'm sure it's both, that like there is a societal reinforcement. And also when you start to feel confident with yourself, everything kind of changes from there. So I started letting the world see me and that was the best feeling in the world, right? To finally feel seen, right? Like I've always been super smart. I've always been a go-getter. Even though maybe in my early years they saw my brother first, right? Um, or I pretended to be into bio because it made me seem larger than I was academically. Um, but yeah, every— my, my career started taking off. Um, my friendships, I felt, got stronger because I was more authentic to what I needed in those relationships. My life in New York made more sense in where I was spending time and what I was doing here. I think negatively, you're always fighting the internal battles in your head, right? Like, there, there is always an imposter syndrome, especially now being this startup founder that's actually done something. Like, really? Um, but body dysmorphia is real, right? And so when people start noticing you for the first time, when they saw you 10 years ago and they would've walked past you 100 times, which has happened, and they start to see you, you know, the battle is mostly internal, right?

Was there a moment when you like first felt seen like that?

Yeah, there was. I remember being at a pregame like for a bunch of kids I went to the University of Michigan with, and there was a guy that I remember always seeing from a distance in school and having a crush on from a distance. And he never saw me once, ever. I was completely invisible to him. And I remember at this pregame, he walked right over to me and like was like making a move and ultimately ended up like asking for my number. And I remember being so shocked in the moment because I'm still Anna, 22 years old, feeling the way I felt then, right? Insecure, a bit skittish, not sure why someone would be talking to me. Right. And there he was. So that was a— that was probably the most tangible feeling of being like, whoa, I must look really different now.

Did you give me your number?

No.

Why not?

I don't know. There's something about— and again, that's maybe it's in my own head of like, if you didn't see me then, why should we spend time together now?

On the flip side, were there any examples of where you did feel invisible?

Moments of feeling invisible. It's— it's hard to pull out. Specific moments. It's, uh, yeah, it's one of those things where like going to college, you know, I was in a sorority, right? Now I kind of think that I was more of a personality hire than anything else in that sorority. But like, you know, all the girls were always invited to date parties. I never was. Um, you know, there, there was— there were all those— I guess it's more in a romantic sense that I was like looked over, right? Um, which is totally fine. It's all good. But yeah, I think mostly in that way, I think socially it showed itself more than anything.

Could you have seen yourself if we went back to like 18-year-old Anna?

Yeah.

And we could see yourself today, how you look, how you feel, all these things. Would you have believed it?

No, not, not at all. And I can say that with such like confidence. Yeah.

Why? Because you didn't think it was possible? Because you didn't think you were capable? Like, why didn't you believe it?

All of those things. I don't think people realize what they're truly capable of. I always saw grandness for my life, but it was very blurry for a while. And now I think something that I've gotten really good at is like manifesting even like the smallest details. Like I can like see my life in total, like 4D, right? Like you're saying now, you can now looking forward and then it was always blurry. It was always like, I want to live a big full life, but I don't know what that looks like yet. This is beyond my wildest dreams.

Where you are today?

Yeah. Yeah.

Yeah, that's really cool.

Yeah. Yeah, it is. It is really cool. I don't think I thought I was worthy or deserving of this much happiness, freedom, love, purpose, and I think crazy enough, like, I do believe, like, losing the weight was doing something for myself. Like, I proved that I was worthy of this type of happiness, right? It's all interconnected for me.

And if there's somebody listening out there who's, like, going through maybe a similar moment in their life like you a few years ago—

yeah—

where they're either— whether it's their weight, their mindset, they're sort of feeling the stuckness and maybe this ambiguity you described, what would you say to them?

Dig as deep as you possibly can to the deepest source of your unhappiness. For me, I felt invisible, and part of that invisibility was like me hiding behind kind of like armor, right? Like, it was— I was, I was hidden. And so for me, I knew I had life to share and ideas to share, and I felt like I couldn't And so I had to unblock myself, right? This was my way of doing so. I'm also like the healthiest version of myself now, right? Like, I work out 5 days a week. I eat super clean, right? Like, I— and I, you know, people, people say I look a lot younger than I am, right? Like, I, I take radically good care of myself, and that makes me feel so powerful, right? And in a career where I have to be powerful and strong and resilient. Like, this is what I needed to do to get here.

When do you think someone should consider blowing up their life?

I talk about this all the time because it's so, it's so scary. But when you feel so anxious and so out of alignment, right, and just like day to day miserable— I've been there, I know this. I'm like describing states that I've been in where you're at a dinner table and you're almost like out of your body, right? You're, you're like looking into the room, right? You're dissociated. When you're like waking up every day and you don't want to get out of bed, when every little action feels so draining, you're not in alignment. Like, I fly out of bed in the morning. I know you guys laugh at me at how early I get up. I fly out of bed. Right? For all of my 20s, I couldn't wake up. And so it's like when you feel like everything is— there is such like headwind against you, like everything you're just pushing against so much, it's time to make some radical, radical changes. And I mean like dump the boyfriend, move out of the house when he's at work, literally, like, uh, like travel across the world, go on a 7-day solo trip. I'm naming all things that I've done, mind you. Um, quick the job that's unfulfilling and doesn't pay you enough. And don't give 2 weeks notice, like, just leave. Um, and you don't need a backup plan. You'll figure it out. When you open yourself up to the universe, opportunities come forward, right? But unless you are completely unattached, like, you, you have to— you, you won't be able to fully let go. You have to be completely unattached. That wasn't so clear, but like, you— it was clear.

Yeah, you can't dump the boyfriend.

You dump the boyfriend, quit the job, jump on the flight. It's true. It's like, these are all real things.

Of all the things you've done to this day, Anna, what would you say is like the thing you're most proud of yourself for?

Choosing myself.

Say more.

In my 20s, it was really, really hard, and watching all of my friends choose marriage and kids, and I always took the other path. And a lot of people have questioned that decision along the way, that I didn't just do the conventional thing in my 20s. I'm 33, right? And I, for the last 10 years, I've been choosing myself and this, this career. And this life. And I've now, like, built the most beautiful life. I'm so, so happy. But, but every step of the way it was seen as other. And that's really hard, right? Because it's like you have to have like that internal stamina to say, trust yourself, keep going, because no one else is right. Society and everyone around you is like, who are we dating? Like, what job are we doing? You know, even my mom being like, I don't, I don't think you should do a startup. It's too risky, right? Everyone telling me to not choose this.

Okay, so you're at Marriott for 3 years.

Just about.

And then you decide to leave and start a company. Take us like to that decision. Why did you leave? Why are you trying to start a company now?

Yeah, it was all very kismet. I met my then co-founder Brendan Strauss at Coachella. Believe it or not, talk about like finding your co-founder in a hopeless place. But this is like 2017.

You guys met in Coachella?

We met at Coachella.

You guys are rolling together and—

Not quite. Not quite. We met at a pool party, you know, one of those like ancillary parties around the festival itself. So we had a ton of mutual friends from New York. And I, mind you, it was a gay pool party and I was the only girl there. And Brendan saw me from across the pool and came right over and we became fast friends. He is— if you meet him, he's sunshine, he's larger than life, and I was immediately taken by him. And when he was telling me what he was doing and who he was, he shared that he was toying with the idea of a video dating app. He had been, you know, in the New York dating market for a while, as had I at the time, and was expressing frustration, right? Every, every date you go on, you're catfished. You show up and they're not quite like you thought they'd be from their 4 photos that are edited, right? No, no, no kidding. He was fascinated by Musical.ly, which is now known as TikTok, and he was really just going back and forth on like, how cool would it be if like TikTok or that mode was actually built and designed for connection? Just the way he was talking I was immediately captivated. I had recently been on like the Marriott Bonvoy launch where it was a small startup team that was working on this new massive loyalty campaign. And it was the first exposure to a small company, right? Even though I was within this massive 14,000-person organization. And I really started liking how quickly decisions were made, how there was just this really tight-knit team, really agile working style. And so when he started talking about what he was building, he really piqued my curiosity, right? And I related. I was going through the same thing at 26 in New York City. You're going on all these dates, you're frustrated. It's, it's— I think it's still pretty bad out there. I'm not sure anyone's truly cracked online dating, right? And so we started hanging out. It was really organic. It wasn't like one meeting at Coachella and then boom. It was like we started spending nights and weekends together. I was still still at Marriott, right? Um, but I started like offering my time to brainstorm and come up with different elements of the product and experience and how we would launch and who we would launch to. Um, and as, as luck would have it, the pandemic kind of reared its head, right? And so we had been spending like over a year building together, um, and then it came time for the pandemic. And what was kind of most affected by the shutdown was hospitality, right? And so Marriott, we were one of the first companies to just be completely furloughed, right? And I was just faced with this opportunity of like, you know, do I risk it all and just jump off the deep end, right? And go all in on this startup, or do I like wait to see if Marriott will rehire me in 6 months, right? And I knew what I was going to do. Everyone around me was like, that's too risky. Why would you do that? Right? And I was like, what else am I doing?

Any specific conversations you can think back to where people were doubting you?

My parents, truly. And I don't blame them. Right? Like they are, you know, we didn't grow up with excess. They have worked my whole life, both parents. And they were both like tradespeople, like my dad in construction, my mom a teacher. They had their craft and that's what they did their whole career. And so like me jumping off of the deep end to go like build an app that didn't exist, they were like, what are you doing? Right? Like truly it was as if I was speaking a foreign language to them. That's really how it was. A very organic start, right? We built a really strong friendship while we were in this like early ideation. And when it was time to get really serious, the kind of the universe pushed me into it.

So you start this company.

Yeah.

And what does the company do?

So it was a TikTok-style dating app, right? So imagine the TikTok feed, but, you know, more in style with Hinge prompts. So people were responding on camera. What's your favorite kitchen appliance? You know, what's— what season do you like the best, right? And you could hear someone's voice, get a sense of who they were, all from your phone.

And did you guys raise any money to build it?

We raised $1 million. Uh, the round was led by Sam Altman of OpenAI, as well as Joel Simkhai, the founder of Grindr.

Cool.

Yeah.

And how did those relationships come about? How did you meet those people?

Yeah, Brendan really led the charge on fundraising at the time. So, you know, Trade is actually my first time truly fundraising because that was Brendan's role within the company. And so he really spearheaded, you know, all capital at Curtin.

What did you learn from Brendan?

Brendan, so much. He was probably most influential in my breakout story. He showed me my worth and proved it to me over and over and over again, gave me the platform to shine and loyalty, like building with a family, building with a crew, and that being unbreakable, really.

And it sounds like through that you've built a really deep relationship with Joel as well. Yeah, from Grindr.

Yeah.

Tell us about your relationship with Joel.

Joel was an early investor and quickly became an advisor and mentor, probably one of the most influential people to my career at this point. I had spent in total around 3.5 years working alongside of him and learning from him. He's a pioneer in his own right, right? He was the first to ever concept geolocation apps, right? Grindr was the first, and He had, he built the business from literally zero and sold for an incredible amount of money. And there's a lot to learn from him. I think a few key lessons are radical customer centricity. If you are not deeply understanding your customer and building for your customer, then like nothing else matters. It doesn't matter how much you raise, who your investors are, if they're like splashy VIP investors or not. Like it does not matter if you are not building something for your end user, full stop. And that has completely shifted how I build. That's probably the biggest takeaway.

Okay, so you raised from Sam and Joel, and then what ends up happening with the dating app?

Yeah, we raised enough to get the product in market, all while the global pandemic was in full blast, right? So we were traveling from college campus to college campus launching this platform, and it, and it worked until it didn't, right? We grew to 60,000 users. We definitely had the early signs of product-market fit. There was something there, right? But as the world started opening back up, we didn't necessarily have the resources to redefine ourselves.

Cool. And then where does life take you?

I spent some time working with Joel Simkhai on his next big app. And so I was, I was doing that during the day and at night is really when trade started to come to life. So I'm from a construction family. And so during that transition period where I knew I wanted to build again but didn't exactly know what, I was spending a lot of time with my dad and watching his business, seeing how I could help and support. And that's really when the earliest, like, signs of trade started appearing. Yeah, it wasn't this light bulb moment. It was Slowly over time, realizing this was a really broken space with a lot of opportunity. But because it's so big, construction is all green space that like you have to be so specific on where you start. It took me a really long time to find that start.

What is Trade?

Trade is a construction payroll, HR, and compliance system built for specialty contractors.

So you start Trade. What does it look like to raise your first round of funding?

Hell, truly. I had a really tough first go. And as I was just saying, this was my first time fundraising.

Sure.

With my first company, it was all Brendan. And so I was new to fundraising in general and new to the CEO role. It's an entirely different beast. So my, my first at-bat in market was like early '23. And if you remember that market, it wasn't a good one. The SVB crash was right around there. It was a, it was a weird time in venture. And I pitched and I pitched and I pitched. And I don't know if my messaging was off or I was insecure and not leading with confidence, but I pitched 149 times and got 149 nos. And I remember at this point we're in May. I had been pitching since January. And I remember looking at my mom and, you know, her especially being like, Anna, maybe this isn't working, right? Like, maybe it's time to put the pencil down. And I felt that for the first time. I was like, maybe trade won't exist, right? Like, how much convincing can I do? How much screaming from the rooftop on like, I know this market, I understand this end user, talking about customer centricity. Like, I don't know why you don't think I can do this, right? And we can talk about that in a bit later on the founder market fit angle, which I think reared its head in my early fundraising days. Um, but I did one more pitch and it was Y Combinator. It was a week after the deadline for the summer '23 batch. And by some miracle we got in.

And looking back now, why do you think they passed?

I think probably my first 80 pitches were bad, right? I think that learning to fundraise is a skill. Learning to tell your story as concisely and intently is hard to do. And so I think 50% were probably really bad pitches. And I have enough self-awareness to say that. Beyond that though, I think, you know, construction's never really gotten the airtime until lately, right? Now we're in a total construction tech renaissance. So I think it was a mixture of market, of founder, of idea. Like, they're like, you're going up against ADP and Paychex. Like, what gives you the right? It's like, well, it's wide open lane, right?

Cool. Yeah. So you get into YC.

Yeah.

What was that like?

Wild. It happened so fast. I think when you get into YC, sometimes you have months and months of notice, right? Like you can get in in January and you have until May, right? We got in in May and we flew to San Francisco 3 days later. So we— me and Kara, my co-founder and CTO. Yeah, she's been with me since This is like day zero of this journey. And so, yeah, we packed our bags overnight really and flew to SF and moved out there for the summer batch. And we threw ourselves into the experience, right? The group office hours, the one-on-ones with the group partners, the social events. We took advantage of it as much as we could. There's a lot to learn from YC and the network you get from it is undeniable.

Wow.

Are there any lessons that have transferred over from being in the dating industry to now being in construction?

Again, I think it's like centricity of the customer, like always building for these. I really build for very specific use cases. If you look at my kind of product history, it's like very specific functions. Like you're opening up this phone or this computer to do a task, right? And so like now it's you're opening up a computer to run payroll. It's a very specific thing. And that's a different mindset to go in than like Shopify or the platforms where you're going on to browse or consume. These are like action-oriented products. That's been similar in both ways.

What's your relationship like with Kara?

We're so different. We're really, um, I think a lot of credit to our— we have no overlapping skills, right? Like, I am very front of house, she is very back of house. That's where we both want to be. I think when you find a co-founder that is truly your yin and yang, like, we are complete opposites. Our skill sets are complete opposite. When an email comes in where someone emails both of us There's never any question on like who's answering because we have such clear lanes. And I think we've watched a lot of founders kind of crash and burn in their working relationships. And a lot of it is because they're stepping on their toes. Right. That just doesn't happen with us. And I think we're better for it.

What's it like working in the construction industry?

At first, very intimidating. Now—

Say more.

I walk into a room with 60 to 100, frankly, white men, right? It's not a very diverse industry, right? And so, and they're all between the ages of 45 and 65, right? And so I'm obviously sticking out. And so at first, especially when like, you know, my product is still in development, we don't have total confidence in what we're putting out there yet, this is years ago, right? There's apprehension for me to be walking into these rooms and sharing what I'm building. Who gives me the right? Right. But you have to get over that. And so I think at first it was deeply intimidating walking into these rooms of men that are between 45 and 65 that have been building their careers in construction their whole lives. A lot of these guys start in the trades. They're carpenters, they're laborers, they're plumbers. And then they move into management over time, right? And here I am, having just come from the dating world, right? Having real no experience in the field, no credibility with them, right? And I'm coming in and trying to sell them a software, right? So intimidating. I was so in over my head, and I could feel their stares. And in the beginning, that would take me back, and I would get a bit a bit like gun-shy, and I've learned to embrace the attention I get in these rooms.

[Speaker:BEN] Sure.

[Speaker:CRISTINE] Because a lot of times they're just curious. Who is this girl? She doesn't look like any of us, and like, why is she here? And I now channel that into, oh, I have their attention. Let me strike while the iron is hot. So what used to scare me beyond is now my leverage.

Any specific moments you can think back to that were particularly intimidating or maybe caught you off guard?

Honestly, every memory I have is me walking into rooms where I don't know a single person, where everyone already knows everybody, right? These are all like— construction, as massive as it is, is the smallest, smallest industry. Everyone knows each other.

It's kind of ironic, right?

It is ironic. All of the competitors are friends. Like, if they're competitors in the market, they actually know each other and they trade notes. Like, and so especially when you're building a payroll system, they all talk, right? So every memory I have of building this business has been me walking into a room where I'm uncomfortable. That's still true, but I'm managing it differently now. Like, I, you know, I take a few deep breaths before I walk in, but I still always get that, like, you know, moment of like, is this the time that I'm going to crash out? But smile, be kind, ask questions, right? Be interested in what they do. And no one's mean, ultimately. No one's mean. And so when you realize that, there's— I've had enough repetitions to know no one's going to kick me out of the room, right? Um, they may stare, but they're not going to kick me out.

Do you have any notes on working with a best friend?

There's nothing quite like it. Kara and I especially, we like love and bicker like sisters, and I think it's something that our team actually really enjoys watching that dynamic. This is the second time I've built with a friend, and for me, I think it just allows the trust to go deeper, the memories to go deeper, to actually enjoy the ride, right? This is beyond a transaction. This is like we are building memories that we're going to tell our kids and our grandkids about, and being able to to explore and feel all of the highs and lows with someone you love is way more enjoyable, frankly.

That's really cool.

Yeah, I'm lucky to have it.

So you just raised a Series A. Again, congrats.

Thanks.

What was that process like?

So different than the first time around. Pretty much night and day, right? From pitching like my life depended on it to, you know, the Series A, which was 4 term sheets in 3 weeks. Unbelievable. Uh, I can, I can kind of break it down, right, for founders that are fundraising, because there is a science to it.

Um, yeah, please.

Yeah, I think it's like deck preparedness and data room preparedness. Being able to anticipate the first 30 or 40 questions that you're going to get and have it ready to go so that like you're not stalling between you have the meeting and they're like, okay, send me this, this, and this, and then you have to take 3 days and lose the momentum post-conversation. We spent about a month preparing the deck and the data room before I went to market. We sat down with our current investors and we said like, what have— what's asked of a Series A founder during their fundraise? And we were locked and loaded. So like the second the call happened, the data room went and I think what that signaled was, oh, they're already moving here. Even if it was my first or second conversation, we had everything so locked and loaded that it made it seem like our process was further along, and it was building FOMO without me even realizing, right? So they were like, oh wow, she's got everything together, like this is further along, and it was our— it was my first week, right? And I really think like more founders need to do that, right? They can't build the data room while they're also fundraising and doing 10 pitches a day. Like, they have to have all of that locked and loaded ahead of time.

Any specific conversations you remember having with the Series A that were notable?

Trade is not an AI-native platform, and we are in the middle of a massive AI hype cycle. A lot of these companies will stay and, and sustain, but I think a lot won't. And there are funds that— there were a few, I think 3 or 4 that I spoke to that as soon as they realized we were not like AI native, the call wrapped within 2 to 3 minutes. I always find that interesting when funds are so pigeonholed into a certain fund, like investment strategy that, you know, you're either going to work for the fund or you're not. I think a lot of people think, oh, like, I can finesse it and get them interested. No, no, they have a thesis. You're either on thesis or off thesis. And it was really interesting. This happened this way more than the last time I was in market where, like, if we weren't AI, it was like the conversation's over. And it's good to know for next round, right? And certain, like, positioning, but That was more felt this time than last time for sure.

So what did the Series A look like? How did it come together?

Yeah, so fortunate to have a global fintech fund lead the round. So WhiteStar Capital led the round and then Suffolk Technologies, who led our seed round, came in to support. YC also came back in, which is super exciting as they continue to be bullish on Trade.

Awesome.

Yeah.

So obviously you've been on a few podcasts before. What would you say is the question you get the most when you're in these conversations?

Probably what it's like to be a woman building in construction.

Hmm. And then what about the question you don't get as much that you would like to?

Like, how am I doing?

You say more?

Yeah, I— it's a simple question. Just like, how am I?

Hmm.

No one asks that. We're as founders are under so much pressure and so much attention. Constantly to deliver monthly, quarterly, annually for our investors, for our team. Our families start expecting things, right? It's a tremendous amount of pressure, and we're doing all of that by— at the same time while we are feeding ourselves, traveling across the country, trying to work out, trying to maintain relationships, friendships, everything. It's a lot to manage, and it'd be nice for someone to just ask how I am sometimes.

How are you, Anna?

I'm convicted. I'm good. I know exactly what I'm doing. I'm focused. I'm definitely tired, but just tired now for, you know, what will end up being so worth it.

What would you say have been the, like, most emotionally challenging parts of building this company?

For the first 1 to 2 years, no one sees what you see, and so you are spending every waking minute convincing people that what you see is worthwhile. People, you're convincing your first investors, your first team members, your first customers, like, look what I see.

Yourself?

Myself, mostly, yeah. That this is a journey worth taking. This is a product worth building. The amount of like mental resilience that is required to push through the entire world not seeing what you see is another level of crazy. I, looking back on it now, I'm pretty surprised that I pushed through the amount of doubt and questioning that I did, right? Like, no one saw this as possible.

What does that self-doubt look like when it creeps in?

Anxiety for me. A lot of that. I think Max and I have talked about my anxiety levels and keeping them in check. I think that's probably my, my personal battle to take, right, is, is grounding myself in what's happening right now and focusing on that versus thinking— because anxiety is all thinking in the future, right? And having to reground. What am I trying to tackle in this moment? Who am I trying to convince right now? What is the next step that I need, right? Instead of focusing too far forward, because that's where you can trip up. Um, for me, that, that feeling is, is just deep, deep anxiety.

Um, when you say anxiety, is it like this existential feeling of like the company's not going to work? What is that? What does that internal conversation with yourself look like?

I think it's two. I think there's a, like, a somatic effect, right, where like your heart is racing, you're, you're— you can't really sit still. For me, that's how my anxiety shows up. I have to like physically start moving my body to kind of bring myself down. I think it can also manifest in questioning, deep questioning, right? What am I doing? Did I choose the right thing, right? Did I, um, spinning out too far forward, right? Instead of focusing on like, okay, instead of getting too far ahead of myself, what can I control right in front of me that could push me one inch forward? So much of this journey is doing one thing a day, one small thing, right? And it does compound over time. It's not about having one big perfect idea the first day you start a company. It's about making smart calculated decisions every single day that get you closer and closer to where you want to go. But it's so massive that that feeling is anxious, right? That's a massive undertaking. If I thought about like where I need to be and all the steps that I need to get there, like that's too much for me to handle. Right? I can only focus on what's right in front of me.

Yeah. Thank you for sharing that. I feel like, like, I, I very much love, um, the work that I'm doing in the company that we're building, and it feels so deeply aligned. But I find that every single day that anxiety comes in, um, that existential fear of like, what if this doesn't work out? What if I'm not going down the right path? Do you find that it also comes up for you every day? Like, how often do those feelings Less and less. Cool.

In the beginning, every single day. Yeah, totally. Especially because I'm someone who— I have a fear of wasted time in general. I have since I'm a kid. I've always felt like I'm running out of time. It's a weird thing that I can't quite like even get to the bottom of. And so anytime I've spent too much time somewhere I shouldn't be, I get super anxious. Going back to like blowing my life up at a few different points, right? That's kind of like, oh, I've spent way too much time on this thing or with this person or at this job. It's kind of like I reach a breaking point and I'm like, I just got to kind of break free and run. And so that comes back to this initial, like that feeling of I can't spend too much time somewhere I'm not meant to be. And I think when you're out of alignment, that's just day to day and that's horrible. It's a horrible way to live. I've been there. It's depressing and it's, you know, it's so unfulfilling. Mm-hmm.

What would you say has been the lowest point in the journey so far?

I think the lowest point in the trade journey was probably that first 6 months when I was so sure that this deserved to exist and no one could listen. No one heard me. And it kind of brought me back back to my early 20s, the early parts of my career, when I felt like I was speaking up, sharing things, and felt like no one was hearing me. It brought me right back there, and I was physically in a very different place, right? But it was, um, it wasn't enough, and I couldn't understand why people weren't seeing what I saw. So yeah, like, as, as much as, uh, you know, Y Combinator bets on a lot of founders, but I felt very, very lucky that they bet on me because it gave me first check, that first exposure point to start really sharing this thing. So yeah, it was a really— I questioned myself a lot during that time because I had spent about a year validating Trade and proving to myself that this platform deserved to exist, and then I spent 6 months trying to raise capital. And so that was a year and a half. It's a lot of time to spend on something that I had never reached the market, right? It was all still in my head. So I was really starting to question myself.

Yeah.

Any specific moments or days you can think back to where you just felt like, I'm not sure if I can go another day or another step forward?

Towards the very end of that fundraising period, when I, like, I was going through the pitches and I almost like hung up and just immediately closed my— I didn't even bother sending the follow-ups because I was like, I was like, it doesn't matter, they're going to pass, right? It got to that point. And I'm so glad to never go back to that point. Like, it really was, it was like, what am I doing? Like, what? Like, this is what a terrible feeling to be so passionate about something that no one can see.

Yeah. To the founder that's listening who is maybe going through a similar fundraising experience, getting a lot of nos, what would you want to tell them?

Keep going. And stay as close to your customer as possible. If you stay close to the customer and to what they really truly need, you're gonna be right and someone will hear you. I think that was my saving grace, was that like no one understood this industry more than me, and ultimately people saw that. But it's so hard, and I, I, I'm not going to sit here and be like, oh, you got it. Like It's, you have to dig deep. You have to really, really want it. And I understand why so many people give up, 'cause it's really hard.

What's next for Trade and Anna?

So much good stuff, honestly. I can't help but smile. This is a dream come true, bringing a product into the world that's fundamentally making people's lives better. It's what I've always wanted to do. I think I went down a different path first, thinking it was more social connection. But I think unlocking financial opportunity to a completely underrepresented demographic is really powerful stuff. And I jump out of bed in the morning. So I think sky's the limit for Trade. I see it being a household name. I see when you get on the subways, it being, you know, the subway promotion. And I think people people will know Trade and love Trade. And I'm excited to continue to bring it to the world. And for me, I hope I just stay happy. Honestly.

I asked you this during the Maker interview, but what is a successful life to you, Anna?

You did ask me that. And I wonder if my answer is going to be the same.

We could compare.

We should. We totally should. I'm in a very different place. A successful life for me is a simple one. I want to build this product and truly like, I want to see it thrive. I don't see this ending anytime soon and I'm excited to be in that journey all the way through. It's also a husband and kids, right? Like when I close my eyes and see a very happy ending for Trade, I want to be able to share that with my family. It's a lot of travel. It's seeing the world that I haven't been able to see these last few years since we've been so, so focused. I have a few DreamTrips that I'm just like tucking away. It's, it's slower. Like, life, life in the future is slower. I'm really excited for that.

What do people get wrong about you?

I think people think I am more extroverted and social than I am. I think in my work persona I may appear to do all these interviews and be on the big stage and that that's how I'm wired. It's not at all. I definitely prefer a slower, quiet life. I'm in bed at 8:30, 9:00 every night. I prefer nights in. So I think I'm I'm probably an extroverted introvert. I can turn it on when I need to, but I think people are always taken aback when they see me online and then meet me in person. I'm a bit more mellow.

And if people listen to this, forget everything we said today, but they could remember one thing, what would you want them to remember?

Don't be afraid to blow up your life. Don't be afraid to leave the job that's not serving you leave the relationship that's not serving you, to take care of yourself in a way you've never taken care of yourself before. Choose yourself 1,000%. Find that alignment, and it's all gonna work out.

Anna, thank you.

Thank you.

Anna, you're the best. This is awesome.

So fun. Thanks for having me. [MUSIC] [MUSIC]