#45: Carolyn Rodz, Cofounder and CEO of Hello Alice — How to transform setbacks into learning, th...

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. Welcome back to From Startup to Grownup, and today I am super excited to welcome Carolyn Roth to the show. Carolyn is the co-founder and CEO of Hello Alice. Hello Alice is a digital platform that helps entrepreneurs save time and make money by curating content, tools, events, communities, and opportunities that work for them and their company. Carolyn has a really interesting background. She went from banker at JP Morgan to a stationery entrepreneur to now the co-founder and leader of Hello Alice. We had a really deep talk about failure and the secrets we keep and about comparing yourselves to others. Never a good idea. Carolyn's grandparents in Bolivia were entrepreneurs, and she's also talked to a lot of entrepreneurs through Hello Alice. So she shares what she's learned about their experiences and her own. It's kind of a masterclass on entrepreneurship. We talk about what makes her relationship with her co-founder so successful, what she looks for in employees and the specific way she hires people and the questions that she asks them. We talk about how she's grown as a leader and what it was like to be 24 hours away from not making payroll. Carolyn is heart and guts and brains, and this discussion is fantastic. You're gonna love it. So please enjoy my great conversation with Carolyn Rhodes, co-founder and CEO of Hello Alice. Carolyn, welcome to the show. I am so excited to have you today and to unpack all your trials and tribulations and successes as an entrepreneur. And I wanna start by asking you specifically about Hello Alice, which is your current venture. What was the founding insight of Hello Alice?

I started Hello Alice based on my own experiences as a small business owner. I left a career in investment banking, started my first small business, and ultimately ended up closing that business down. I started a second company, which I sold 7 years later, and it was that realization that the same business owner could have very different experiences based on access to capital, networks, and knowledge. And it really became my life's mission to help solve those problems that I encountered for as many entrepreneurs across the globe as I possibly could.

Yes, I can totally relate to that. Of course. Tell us specifically what Hello Alice does so everybody understands.

We are a free platform for small business owners, helping them to improve their business health. We focus on the fundamentals that it takes to start and grow a business. And based on the type of business owner that somebody is, based on the type of company that they're trying to grow and their own aspirations, Hello Alice automatically connects you to sources of capital to expertise, into step-by-step guides at every step along the way. And it really recognizes that the path is so different for, for every entrepreneur. We're all tackling the same kind of macro issues, but the solutions that make sense for our businesses are really different based on the type of company that we're running.

Yeah.

So the magic of Hello Alice, right, that we're making those matches in a smart way based on your business.

That's really great. So the idea is that you provide resources across the board and then people can kind of find themselves inside of that.

Yeah, it, it makes recommendations based on your personal and business profile. So if we know that you are a manufacturing company based in Iowa with 50 employees, your recommendations are going to be different than a tech company based in Florida maybe run by a veteran entrepreneur. There's unique resources available for certain demographics. There's unique resources based on where you live. And our job is to make sure that we're servicing those opportunities at every turn.

Yeah, I love it. Now, you sort of talked about your, your background before you go to Hello Alice. I'd love to talk about, first of all, your career at JPMorgan. So my understanding is you kind of glamorize like, I'm going to go to JPMorgan, I'm going to be successful. I'm going to live in New York, you know, all the things. I can totally relate to that. That was my business school model for sure. But talk about your trajectory at JPMorgan and kind of what happened.

Yeah, I, I grew up— my grandparents were entrepreneurs. They ran a cookie and bread factory in La Paz, Bolivia. My dad was an entrepreneur. He ran a commercial insurance company in Spring, Texas, and I had I had grown up seeing how hard entrepreneurship was. And so for me, I was like, I wanna go do what I see all my friends' parents doing, these corporate jobs, these fancy offices. I wanna go that path. And I started that way. You're totally right. I completely glamorized it. And it was fun. I mean, it was a great experience. I got to meet— what I found got me most excited in that job was meeting the self-made, you know, successful business people that we were helping with big mergers and acquisitions. And that was the part that I would get really, really jazzed up about. But what I felt was lacking was the real mission-driven component of what I was doing. I felt like there wasn't a whole lot of creativity. It was very technical, and I'm sort of one of those right-brain, left-brain hybrids. And so I just always felt like there was something more. I remember, you I would, I would see my colleagues getting super excited when we closed a deal and I just never felt that. I definitely, I felt the lows. I didn't quite feel the highs and I was like, this isn't really the right path for me.

Yeah. And so how did you decide from there to leave? Because that is not so easy to do too. First of all, if you have your whole kind of identity on, I'm going to live in New York and I'm going to have this like fancy job, then what? You know, like, oh, that didn't work. That's actually very— I experienced that myself at PricewaterhouseCoopers, actually. And I really remember how difficult it was to realize, like, uh-oh, washed up at 27. What am I going to do now? Because I'd really banked on this thing working out. So what was that like for you? Did you have a moment of truth that you decided, that's it, I'm not going to do this anymore?

You know, I'm the type of person that I often am working hard just to prove things to myself. And I think when I look back at that period of time, I I was exhausted. I was so tired. I was not enjoying my work. And I'm really grateful I got, I would say, nudged out. Not fired, but nudged out. And I think it was probably the best thing that could have happened to me. In my mind, I was looking at it like a firing. I think it was basically the same, but I was up for— there was one position at the associate level, and I had been— I had actually already gotten a job at Goldman Sachs about a year earlier, and they had committed to me that that position would be mine if I stayed. They gave me a nice healthy raise. They asked me to stay. I was flattered, and I stayed even though I didn't love the job. And I, a year later, when it was time for that position to be open, it was political. There were people that others wanted in place. Someone new had taken over the team, and so They were like, we've got this great marketing job over here that makes half the salary and you should totally take that. And I'm like, I was so pissed off. Yeah, I was like, I'm out. I'm done. You guys really betrayed my trust. I'm done. And in hindsight, I'm so appreciative. The funny thing is I'm friends with a lot of those people now, and I'm really grateful because I think it was sort of the universe telling me I knew I wasn't right for that long term. I wouldn't have stuck with it. Forever, or maybe I would have, even worse, but it wasn't the thing that, that, yeah, killed me. And so I left really not knowing what I was going to do, just knowing that I can figure this out. I'm like, if you're going to offer me a marketing job at half the rate, I know I can go figure out on my own how to make half my salary. So worst case scenario, I'm going to go learn this on my own. And I did. I learned it with a lot of bumps and bruises along the way, but I figured it out.

Totally. Well, I think you went from there to become a stationery entrepreneur, a stationery mogul, right? So, so sort of trace that journey. Trace that journey.

I'm not a mogul. I have a ticket for it. So I, I shortly around that time, I was actually out just having, having drinks with a friend of mine who ran a wholesale company of like luxury home goods. He had these beautiful candles and all of these things. And so we were talking and I'm like, I just keep— I would go to these shows and just go support him and pop over to his— he had these, you know, great sales reps with these fancy showrooms everywhere. And I would pop in to support him. And he was like, you know, you should do something. I was like, I just love how creative your work is and how neat that you get to do this stuff and such a great salesperson and stuff. Well, you can do this. You could totally do this. And so the National Stationery Show was coming up and he's like, let's, let's do it right now. He's like, just get your booth. And I remember it was $600. I had the back corner and I was like, all right. And we were drinking margaritas and I'm like, I'm going to do it. I'm going to do it right now. And I got online and I bought a booth and I had no idea what I was going to do. I just said, I was like, all these products are so like ordinary. Everybody's doing like, it's the same thing. I was like, can't somebody like jazz this up a little bit? And so I bought a booth and then I had to figure it out. And so I started a home and gift line, again, largely sight unseen. But I love beautiful packaging. I love design. I just loved the really like tactile experience. And it felt so simple compared to this, you know, complex world of investment banking. If anything, I think it was just a little distraction and departure from, from what I was doing. And lo and behold, at that back corner booth that I signed up for. My mother came and staffed the booth with me. I packed that whole booth into two suitcases and ended up winning Best New Product at the New York National Stationery Show. That's incredible.

Carolyn, before you go on, what was the product like?

What were the things that you— It was so— I had all kinds of fun. I had wrapping paper and then I had, I had these little packages of like scented stationery. So I had these little like scents, these little bottles of fragrances, and they all had like fun little personalities and than the cards that you could do. And so it was more of the storytelling, I think, behind it than anything else.

But the packaging was—

I paid so much attention to the packaging, to every little label, like every piece of that product was just such a labor of love and so much fun that I think it was just a little bit, a little bit different, right, than everything else that was out there. And so I ended up having— and I didn't even know. The funny thing is they had announced who had won best new product out at the front. And here I was in the back corner manning my booth, and all of a sudden these buyers started coming by and nobody went back to that corner. Like, even like the buyer from Neiman Marcus came by, the buyer from Harrods came by, and the buyer from Bloomingdale's came by. And I started getting these purchases and I'm like, what is going on? I remember my mom being like, oh my gosh, this is so cool. Then all these like press people started coming by and it just felt like I was like, I'm actually like, this is pretty cool. And so I was making all these orders with a great show. I'm feeling really good about what I'm doing. I'm like, oh my God, I made more money today than I would have made in banking. Like, this is amazing. But I knew nothing about the retail world at all. I realized I was great at getting a product onto shelves. I was not great at getting a product off the shelves and into the hands of customers. And I totally misread that whole part of retail. That you had to go train sales reps and you had to go show up in the stores and you had to go push your products. And I just didn't have that piece. And this was early in the days of online marketing when there wasn't much of a direct voice to consumers. So it really did happen through, through sales reps. So it became where I was. I had these big initial orders. I put a ton of money out into building up inventory and then the repeat orders didn't come. And so it really just became an issue of, of cash flow management and having enough time to float in between and live my life, which hadn't fully adjusted since my days as an investment banker into the life of an entrepreneur. And eventually I just ran out of cash. And it was, you know, I think this difficult experience in that it was the first thing I'd ever done in my life that I had poured everything into because I was working around the clock. I was working just as hard as I worked at a banker. I hadn't quite figured out how to even regulate since that schedule. And I had failed. My cash was going away. I got to a point where all of a sudden I had, you know, credit card debt. I didn't know I was going to make my mortgage payment the next month. I, you know, every penny that I was spending, I would go to the grocery store and have peanut butter and jelly sandwiches because it was the cheapest thing to get. And I just sort of had this moment. I was— it happened so fast, I think, from this time of, you know, it was a matter of of maybe 6 to 9 months where everything kind of just started unraveling. And I remember looking around me like, what have I done? Like, what has happened? I've put everything into this. I've worked my ass off and I have nothing to show for it. I'm worse off than if I had done nothing at all. And it was, it was probably one of the most demoralizing moments of my life. You know, you're around these, my friends now that are getting promoted, that are moving up the corporate ladder. And here I am being like, I don't know how to make my mortgage payment. And I've got, you know, now bills coming due. And it was overwhelming and the biggest knock to my ego, I think, that I've probably ever experienced.

Yeah. Do you remember what you told yourself in those moments?

I think I was frustrated with myself. I was frustrated with myself that I had let myself get to this point because I knew I would just look around. I'd walk down the street and I'd see businesses all around me. And I knew my grandparents had done this, my parents had done this, I have friends' parents who had done this. I'm like, why can't I do this? Like, what did I do wrong? And I was just broken. And I hadn't told anybody. I think my biggest mistake was that I was, you know, externally I was getting press, I was in these stores, all my friends were like, this is so cool, you have all the flexibility in the world and look at you and this must be so amazing and you get to go to these fun shows. And were so jealous. And I kind of just lived that facade externally. And then behind the scenes, life was unraveling. And I was frustrated. I was frustrated. I felt like I couldn't lean on people to ask for help because everybody thought everything was great and I didn't want to let them think otherwise. And so I had this amazing network, but I couldn't tap into it at all. I felt like I wasn't quite ready to leverage certain contacts and to try to push certain things because I just wasn't there yet. And so when it all unraveled, I was— I took a lot of time to just process it for a moment. I got a job making, I mean, maybe 25% of what I was making as a banker. I worked as a personal assistant for this lovely woman in my neighborhood, helping her with odd jobs and just taking a minute to piece together life. I actually applied for some jobs back in finance and didn't really find anything that fit. And I just kind of floundered for a bit. I mean, I think it was probably a year of just bouncing around trying to figure life out. But in that time, I studied a lot. I read every— it was podcasts like yours and books and talking to people. And I just ingested so much information around why certain entrepreneurs succeeded and certain entrepreneurs failed. And as I started watching, the ones that succeeded asked for help at every turn. They surrounded themselves with great experts. They always reached out for help. They brought— they built amazing teams. And I had tried to do everything myself. I didn't hire employees. I didn't ask for, for guidance. I didn't have mentors. I didn't join networks. I just thought I could do it on my own because I'd always done things on my own and I'd always been successful at doing it on my own, and I felt like I needed to do it on my own. And so I think that was the biggest turning point for me that was like, I'm never going to make that mistake again.

Mm-hmm. To do it by yourself and not ask for help. Yeah, that's such— thank you for sharing that. It's, it's just— and I know you've done a TEDx talk on failure and, you know, reclaiming failure, but let's be honest, especially before you kind of recognize that like, oh, failure is part of the game. And it's like so embarrassing, especially to your point when you see you're comparing, right? Comparing to your classmates and to other people, maybe even to your parents and grandparents who have somehow managed to do this, but you can't do it. So I just wanna, I really appreciate that you just brought that up because it's so important to be honest that actually having, you know, hitting bottom is often part of the journey and part of the process.

It's hard to recognize, I think, when you're there, right? Because you always are sort of in denial that around the corner things can get better and I can do this and I can pull myself out of this. And I think that was the, the idea that I had sort of implanted in my head, that if I just worked harder and I just pushed a little more and I just like figured out the next thing, I could extend a runway a bit and I could, I could get through this, what I thought was rough patch. And I, and I didn't want to disappoint people. I knew if I told my parents, I would worry them. And I'm like, "Well, what are they going to do? They can't really help me through this. Like, this is my problem." And if I told my friends, like, they're— they don't really care. They're going to wake up and go to their jobs the next day, and they've got their own lives to deal with. So I never felt like telling people was going to change anything. And I also felt like I could fix it. I think I was just like, "If I just push more and do more and work harder, I can fix this. And the reality was the business model was flawed. There were fundamentals to that business model that didn't work, and it didn't matter how hard I worked, the business model was broken. And had I done it in a different way, I certainly could have made it work. But at the end of the day, even when I penciled it all out and worked everything out, I'm like, this actually doesn't provide for me the lifestyle that I want for myself. And if this all turned around is this what I want? And when I finally had that realization with myself, that's when I was like, I just have to shut this down. It's— yeah, I don't love the business. I'm not super passionate about the business. I really started this on a whim a little bit. And so in that kind of time of diving deep and figuring out what I wanted, it made me really sit back and say, do I want to go back to the workforce and get a job? And maybe banking wasn't the job that I wanted, but there's lots of other jobs out there. And what might that be? And so I started really digging into the world, like what I loved, and realized a lot of it was around branding and marketing and storytelling. And there were these aspects that got me so excited. It was like the parts that I did love about investment banking, putting a pitch deck together for a client and getting to tell their story and highlight what was really unique about them. Like those pieces I enjoyed. I loved the part of building a brand with my own company. And so I went down this path of branding and marketing and realized, you know, one, I can— I need to learn the business. That was one of the takeaways for me in retail. I was like, I need to learn the business before I jump into the business. And so I went and worked for a branding agency for a bit and just again continued to ingest a ton of information. My salary was okay. It got me through. It wasn't anything to write home about. It's still not back to my banking days. I sort of felt like my career had taken this slide backwards a bit. But I loved the job. I loved the people I worked with. I loved the clients I got to work with. I learned so much and took that knowledge. And I think all of those experiences, now I look back, I'm like, I would never be where I am today if I hadn't had all of these, you know, weird discombobulated pieces along the way.

So yeah, in a weird way, I guess it always works out, but I'm not sure if it always works out, but I, I think when you keep, when you have a certain temperament, right, and you have a certain kind of mindset, it, it works out because you can learn from every experience as opposed to letting experiences crush you. Like you said, you were broken, but guess what? You fixed yourself, right? Like you were able to process and imbibe and learn from an experience to help you, like as we say, sort of fail forward.

Yes. And I should say, I mean, I'm the type of person that I don't like to be told no. And I mentioned before that I'm often more than anything trying to prove things to myself. And that really became, I think, for my second company, a huge piece of, of why I started it. It was less about— and I should mention that I left working for this branding agency. I ended up starting my own business again because I had that nagging sort of feeling that I needed to prove to myself that I could do this. I kept seeing entrepreneurs around me that were succeeding. And I knew I could do it, and I just needed to have some, some quantifiable evidence behind that, that I could do it. And I remember writing down every way that I was going to do this differently, why it was going to be different, how I was going to fix what I had messed up on in the past. And, and I did. I ended up growing that company. I sold it 7 years later. And again, I would say where I, where I didn't feel like I quite nailed it with that one, as I didn't have sort of the passion and the mission-driven side of it. But it solved the problem of proving and rebuilding the confidence that I had lost in that first experience of me knowing that, that I could do this.

Yeah.

And recognizing that, you know, it's not rocket science, but entrepreneurship is not a solo sport. You have to bring the right people to the table. And you have to build the right team and you have to put the right resources behind you in order to set yourself up for success.

Yeah. And it sounds like you implemented all those things or more, but kind of better inside of the second business, which was like a web branding agency, right?

Yes. I started as a really a consulting model. Yeah. And eventually grew that into selling and building technology products for clients, which is sort of my first foray into tech. And that was kind of what then after I sold that business and coupled with the fact that I was then mentoring other companies and this whole world opened up to me, right? I sold my company. There weren't that many women who had sold businesses at the time. Still today, they're not a whole lot. Right. And all these doors opened up. So here I was. People were like, come speak at this conference, come join this network, come do this thing. And I remember being like, you know, I just had a baby. I don't even have a business right now. And now all these doors open up to me. I'm like, I'm— this is the last thing I need right now, but I know a million people who need this. And so how can I start to just use these connections that I have to bridge other people into the things that they need? Um, and it became sort of this, I think, like awe and excitement that all this stuff existed out there that I had no idea was there, but also this frustration that I didn't know that it was there when I needed it and what a difference would it have made. And so that was really the impetus for starting Hello Alice was how do we help connect people in much more effective ways and bridge this ecosystem together and stop everything from happening through word of mouth? How do we actually leverage technology? Like, here we are in this, you know, industry of tech and we're the least tech-enabled industry in the world is the reality, right? Everything passes through word of mouth. It's who you know, it's what room you're in., and that became and continues to be, I think, my, you know, what excites me every day that what an opportunity if we can break those barriers down and build efficiencies into this space. Imagine the amount of people out there that were just like me that had ideas and had things that they could do and had jobs that they could create and, you know, value that they could provide, but just don't know the right path to get there. Right.

And need those resources. And to your point, community and mentorship, but then also actually knowledge and access and all those things together. I really love it. And then how did, how did Hello Alice actually like spring into existence and how did you meet your co-founder, Elizabeth Gore?

It's saying it sprung into existence, which is a great way to describe it because it was very fast. I, I had this idea after I was mentoring these companies, and I felt like I was answering the same questions over and over and over again, but I was answering them in different ways for different people based on who they were. And so I started with the idea that, that if we could build technology that could take this data and ingest this data in and spit out a recommendation that was based on what worked for and learned from more and more and more entrepreneurs as more people used it, how powerful that could be. And I was having this conversation at a conference, one of these conferences that I'd been invited to because I had sold this business and that I never knew existed before. And I met Elizabeth. We were simultaneously around the same time. We had a mutual very good friend and we were in her wedding together. And so these things kind of all happened in tandem. But yeah, so I'd seen her at this wedding. Fast forward, we were at this conference together and we were having this conversation about, you know, what's next and what are you doing? And Elizabeth was then the head of the Global Entrepreneur Council for the UN Foundation. And I was pregnant and bouncing this idea around in my head. And she was, you know, on her third beer having a good old time, like sober as can be. And yeah, of course, I have a really nerdy conversation. Yeah, right. I would just start going off on this tangent. And she's like, "Oh, I'm really interested in that." And she kind of started going off on the macro issues and what entrepreneurship solved for the world because she had been in Africa and East Asia and these very exotic remote places, Latin America. And it resonated with me. I had family in Bolivia, and so I'd spent a lot of time there seeing the power of entrepreneurship. And so I think we both had enough that we can kind of really understand where the other one was coming from, but realized Well, this is actually bigger than I initially thought, that if we can solve these problems, it's not just solving the problem for a single entrepreneur and even a group of single entrepreneurs, but it's really solving problems for society at large and big global macro issues. And so she said she was like, look, I really want to continue this conversation. Let's, let's talk some more. I want to figure out how I can support you. And mind you, Elizabeth, you know, this was at the same time she was off having dinner with the Obamas and being, you know, she was keynoting the conference. And here I was being like, I'm just here, got my baby at home and sorting through life. And my life was just very different. And so I kind of blew it off and I was like, I'm sure she's, you know, got caught up in the moment and she's busy. Yeah, things as people do. And fast forward, we were at another conference together about 2 weeks later and she pulled me aside. She's like, I'm really serious. I actually, I really want to support you and 'How do we do this?' And let's, you know, paper this thing out and put this plan together. And that was the spark of everything. I think when I started thinking bigger, I just— it made— it kind of opened my mind up to, 'Okay, I have this idea,' and I was going to sort of tinker away at it as a side hustle. And then Elizabeth just sort of— I think it made me think much, much, much bigger. And it's— we've probably had that relationship ever since. I think I always— I sort of come up with these ideas and she's like, all right, we're making this happen and here's what we're going to do it. So it's been this great partnership. I have no shortage of ideas, but she's great at bringing the right people to the table to amplify them and help bring them to life. And I'm often, you know, the person that's like, okay, here's, here's technically how it needs to work and what we need to do to build it and all these pieces that need to happen. And here's who would be great to bring into this. And then she goes out and she, you know, puts every connection together and has no fear in making the ask to, to bring the right resources to the table.

Yeah, that's amazing. Did you— when you decided to paper it into like, say, yep, we're going to become co-founders now, you know what I have in my book From Start-Up to Grown-Up is this co-founder prenup, as in like, let's have these conversations before we decide to start a business together. Because it's a really important business relationship. You're going to see her more than you see your own spouse. Did you know that you were aligned? Did you have a lot of conversations? Did you kind of be like, okay, feels good, let's do it? What was your process?

You know, there's definitely something about just gut instinct. We did start slow and it was funny. I remember she sent me her— she's like, well, I can help you out. Here's my day rate. And I just laughed because I was like, well, I can afford about one day of this. So, of course, And so we still laugh about that. I'm like that. She was— she had then shifted over. She was working as the entrepreneur-in-residence at Dell, working directly with Michael Dell. So she was making much more money than I was ever going to pay at the startup phase. And so she started— we started out, I gave her a small piece of equity. We both— it was funny, we both called our mutual good friend and said, hey, we're thinking about working together, what do you think? And she told us both, I don't think that's a good idea. Like, you guys are very different. And neither of us had told each other until years later that we had called this friend.

Hilarious.

And that we had gotten this advice that no, this is not a good idea. We both ignored it clearly and decided to work together anyway. But it was a small, I think a small risk at the beginning. It was like worst case scenario, it doesn't work out and, you know, lost a small chunk of equity. But little by little, Elizabeth brought so much to the table and kept putting more and more time into it that we renegotiated later. We were sitting in a coffee shop in New York outside a meeting with L'Oréal. I remember going in to meet with L'Oréal about a contract. They were one of our first partners. And right before the meeting, we're like, all right, we're obviously in this much deeper. I was like, I want you to go full in. She wanted to go all in, and so we kind of scrapped our original agreement and split things much more evenly. And it was a risk still. At the end of the day, we didn't know each other that well at that point in time. But I think we were so aligned in terms of what we wanted to do with the company, why we were doing it, type of culture that we wanted to build, the difference that we wanted to make. Like, the important things aligned. And at this point, we did both know that the other was going to work their tails off to make this happen. It was that, that trust that I think kind of put us, put us over the edge with each other.

Yeah, I think a lot of co-founders, you know, it comes down to feeling that you have alignment with mission, but also trust, and specifically trust around that person is going to work as hard as I am. So I'm never going to have to like be like, I'm so resentful that I'm the only one working around here. I feel like that is a common theme with co-founders.

Yes. And I think what I realized, Elizabeth, her superpower is she's one of the fastest workers that I know. We would always, still to this day, we'll be on a phone call together, you know, you go through your list of like, all right, you're gonna do this, this, this, this, this, I'm gonna take these things and let's go divide and conquer. And 9 times out of 10 before that call is done, Elizabeth's like, all right, I've already emailed that person, I've already done this thing, I've already sent this text, I've already— and you're like, oh, like slow down a minute. So She's so fast, but it builds this momentum for our company that it's like, all right, you said you were going to do this by the next day, it better be done. I'm the type of person that I'm, I'm always going to deliver. Like, I don't like to show up unprepared. I don't like to not have things ready. And so it was sort of this race to like keep up with this pace that she had set, which just left us running and accelerating. And I'm also very detail-oriented, so I will give I'll stay up till 3, 4 in the morning to make sure it's perfect. She's out like firing out connections. It sort of— it built this instant accountability for our company that we had to move fast. And I think one of the big failures with many startups is that there is no accountability, right? You're building things, but there's no deadlines. There's no sort of hard, you know, things that need to be hit along the way because you don't have a lot of clients. There's no like external factors at play. And but we had that, we had like people we had to show up for, things we had to deliver, and it made us work so fast and efficiently. And I think that's what fueled so much of our early growth.

Yeah, that's really powerful. Actually reminds me of your, your stationery store or your stationery conference thing. You said you bought a booth and you're like, all right, I need a product. You have a deadline. So deadlines really help and you've got to create deadlines if you don't have them. So significant.

We talk about that a lot at HelloAlisa Cohn. How do we create a platform? I think we've done a lot of this, but holding entrepreneurs accountable to the goals that they've set for themselves. If you say that you want to go raise capital, we're going to hold you accountable to that goal. These are the things you need to do to get there. Why haven't you done these things? Make sure you're showing up and building that sense of accountability. Because it is really easy to be like, okay, I need to go raise capital, but I also need to go hire an employee, but I also need to go sign that lease, but I also need to go get inventory. And you end up actually doing nothing at the end of the day. And so it's one of the reasons in our technology that we force business owners to choose one goal at a time. Of course you have a million things you need to do. You get to focus on one right now, and we're going to hold you accountable to that one. Dabble in all the other things, keep racing, keep doing it all because you have to, but we're going to hold you accountable to the one that you said was most important. And I think that mentality is so important to keep people pushing, pushing forward on the big things that matter.

Yes, very powerful. Absolutely. So in the trajectory, remind me, what's the— what year did you start? Hello Alice. How long have you been?

We launched in May of 2017. And so we started, I would say unofficially, we kind of started around— it was around 2015. We had a couple of conferences, we ran an accelerator program. We, we sort of started building the community and the, the company and the brand, I guess, a little bit. But the technology we started building January of 2017 and we launched in May of 2017.

Yeah. Amazing. So with the trajectory and all the ups and downs and there are plenty of downs we could pick to in the macro, we could look to in the macro environment, were there any kind of near-death experiences that you thought, oh, I do not know how this is going to go?

Yes, the biggest ones were around payroll, not surprisingly. I think there were many—

not surprised—

who were going to have those freakout moments. We— ours was around— so that's probably the most memorable one was when we were raising our Series A. We really struggled in our early fundraising. Our seed round was incredibly difficult. We raised way less than we had initially set out to raise. I think that ended up being a blessing in disguise because we didn't make as many stupid decisions as we probably would have had we, had we raised more. But when we went out to raise our Series A, this was a sad past week for us because Silicon Valley Bank actually led our Series A and saved us. We had gone to so many different investors. We were told no every way you can imagine., and it was John China at Silicon Valley Bank that, that stepped up, led our Series A, uh, and we were 24 hours away from not being able to make payroll. Alisa and I had already cut ourselves back to making nothing. We were, you know, taking out second mortgages on our homes. Like, we were— we'd done everything. And of course, you have to, you know, you don't want to fill your employees in on everything, that you're down to the wire and hoping this stuff is going to pull through. But we literally got funding 24 hours. I mean, when that money came through our bank accounts and we just sat there, we were in a parking lot getting ready for a meeting and we just sobbed. We felt like this, like, relief that, okay, we could do this. Like, all our metrics were pointing in the right directions. We were just— it was cash flow and we knew we were like, we can— we think we can do this. We know we can pull this off. We had enough investors that were showing enough interest and we're like, one just needs to show up for us. Just need one. And thankfully Silicon Valley Bank did. And, and we got to see the light of another day.

What a dramatic story. It's—

I mean, it's terrifying right there. I remember going to the dentist and the dentist was like, do you ground your teeth? Like, like, what is going on in your life? I'm like, it is stress. Like, I go to sleep every night. I'm so stressed out at this point. You know, you're letting down employees and you're letting down investors. And it's not just about you. I know I would be okay. I'm like, my, husband had a job. We were, we were okay. It wasn't going to be, not, you know, great, but I was going to survive. I really, I mean, it was, it was so stressful for all the people around us that we were going to let down. And I think that's what happens at some point. Your business becomes so much more than you. I knew I'd already failed. I knew I was going to be okay. I had never failed other people before, and that was a moment of— I think lessons learned in that piece of the journey were, one, we were never going to cut it that close again. I think Elizabeth and I both got through that. We're like, this was like, you know, it would have been hard, but we should have laid people off way earlier. We shouldn't have let it get this far. We should have cut things back way beyond. But your runway isn't as long in those early days, right? We were a year and a half into the business and your, your ups and downs are a little bit lumpier. And we had— luckily we had contracts that we knew were going to renew, so we knew things were coming around the corner. It wasn't like the business was in dire straits. The business was growing and doing great. Cash flow was just really lumpy. We would get a $400,000 contract and then we'd be months with nothing, and then we get a $300,000 contract and we'd have nothing. And so we just really learned, I think, to manage our cash flow, to give ourselves a whole lot more runway and to plan much better for worst-case scenarios. Luckily, we didn't have a worst-case scenario, but we weren't prepared for it if it had happened. And right now we definitely are. Right.

How did that— how did those lessons— did you draw on any of those lessons when there was a global pandemic? Right. As you may recall. And I'm just curious, I mean, all the startups that I work with and really obviously everybody around the world had a moment of pause and frankly a moment of panic. And then some things, you know, worked themselves out and some things really didn't in terms of businesses. What, what did you think was gonna happen when the pandemic came upon you and, and how did that play out?

So we thankfully went into the pandemic really prepared, and I think a lot of it was because of this experience that we had had earlier. We, had also put our biggest marketing campaign together to date. It was an election year. We had put a whole plan together around how we were going to help small business owners, or one of the most prolific voting, you know, blocks. And so we were going to go out and really support— it's a bipartisan issue. Small business, one of the few bipartisan issues. And so we were like, this is a great way to get out, to get people, you know, to get in the public eye more and to support something that matters for our country, but also to show up for our business owners, help them understand the issues that matter to them. And so we were going to launch this whole campaign at South by Southwest. We had put our biggest budget to date behind it. And if you recall, days before South by Southwest that year, they canceled it.

Oh, I recall. I recall.

It's 3 days before. Yeah.

South by West. March. March 2020. Yeah.

Yes. We had I mean, we had a food truck, we had all this press stuff, we had like printed— I mean, we had thousands of boxes of giveaways that we were going to do that were sitting in a storage unit in Austin. And I was like, come hell or high water, we are going to Austin. And of course our team, we had employees that were really uncomfortable with it. I'm like, whoever's uncomfortable doesn't have to go. I'm gonna go. If you're not, obviously totally understand that. I'm going and I'm going to go find these businesses and support them, show up for them. And that really became our ethos around the pandemic was that we were going to show up for our business owners and we had no time to even sit and process what it was going to do to us. I think for a minute we kind of spent like 24 hours being like, oh, this sucks. Like all this effort that we put forth, all this money, we just like flushed $200,000 down the toilet. But we're going to get through this. Imagine what all these other businesses that are not as well capitalized, that aren't prepared for this situation, what are they dealing with right now and how do we show up for them? And so we took this whole plan that we'd had to give small business grants away at the end of the year or on voting time. We're like, let's take that, we're going to accelerate it and let's give away money right now. We became— before the government had announced PPP, before anybody was— before corporations had pulled anything together, we were one of the very first organizations to start giving away money to help business owners. We gave away $10,000 grants out of our own pocket that we had planned. But what it did was open the doors for everybody to say, ah, here's an organization that knows how to give money and can help facilitate and connect to business owners. So all these corporations came to us and started leveraging our technology, started leveraging our community to connect founders to funds. And it became what, what was very scary time for us, certainly probably more scary for our community. Business owners became a massive opportunity for us as a business and for small businesses everywhere because it shines such a light on them and what their needs were and how they could support that. We felt like we've sort of been like beating this drum of how do we bridge corporate, the corporate world with what entrepreneurs need. And all of a sudden it was like everybody wanted to do it and we didn't have to try to convince them anymore. All we had to do was be the mechanism to bridge those worlds together, and that's what we've been building for so long. And so it became a period of massive growth for our company where we went from, you know, we'd get thousands of owners every week to getting hundreds of thousands of owners on our platform. And it was then the big thing became, okay, how do we actually support this and how do we manage this growth and how do we handle things like, you know, fraud and how do we handle data security and all these pieces that we were then really scrambling to make sure that we were so buttoned up on, which thankfully we were, we were ahead of the curve on anyway. I will say I'm very grateful to our chief product officer who was always, you know, he's like, I need data security, data security, data security. And I'm like, all these other things to deal with. Like, let's do the basics, the bare minimum. And he always went above and beyond. And when we had this massive growth, I was like, I don't know, Kelsey, you, you saved us. Like, you really saved us. And thank you for pushing so hard on this because this, this stuff matters tremendously. But we've always been, I think, ahead of the curve for a company of our size.

Yeah.

When it comes to security, thankfully.

Yeah, thankfully. Yeah. Because that's the whole thing, is that like the growth is great. First of all, that's amazing. And also being able to connect to mission.

Right?

Like, okay, this is our moment, right, to help entrepreneurs. That's our mission. And oh, by the way, it's good for business. It's fantastic.

We're growing.

Oops, we're growing too fast, right? It's that sort of, you know, constant balance with startups.

Yeah. The exciting part there was that we truly did it for mission. At the time, there was no business model behind it. I mean, giving money away was probably a bad business model by anyone's measure. But what we realized was when companies started coming to us and then they were like, all right, we're, you know, what do you charge for this? And we're like, I don't know, what do we charge for this? And so we kind of think this, you know, packaging this up in a way that really helped, it helped the ecosystem, it helped us as a business, it helped the business owners. And we're like, there's a real win-win-win situation here that, that is sustainable and that we can grow and we can build. And it opened up lines of business for us that we would have never had otherwise. But it also proved to our community of entrepreneurs that we really care, like we're going to show up. We were partnered up with the U.S. Chamber of Commerce and we were helping. If you recall, the rules were changing daily on what did a salon need to have, what happened to happen at a restaurant, and how do you do business and taking cashless payments. And there were all these things happening. How do you get PPP? How do you connect to your banker? Which bank is taking it? Which bank is not? How do you get an emergency loan? And so all that stuff, we were just daily, I mean, day and night, we were pushing out whatever we could find and however we could find it. And it really became a conduit for everybody to say, okay, I've got this information I need to push out. How do I push it out broadly and quickly? And we were there. And it meant a lot of sleepless nights and a lot of stressful times, but it was rewarding. Rewarding on so many levels when I mean, so many levels that you'd hear from these business owners, they're like, my business is alive because of what you all built and what you did. If that was one story that I heard like that, it would be enough. But to hear so many, it's like this fuel that just, I don't know, it lights me up because every time I talk about it, I'm like, it's the coolest part. I always say I have the coolest job in the world, but it truly is. I can't imagine doing anything more rewarding.

Yeah.

Yeah.

It's so rewarding to hear that and to, to realize that you're making a difference for people, especially given your orientation as an entrepreneur helping entrepreneurs. So that's very powerful. And I can imagine also your employees, of course, taking a lot of, you know, support from that as well. And at the same time, you're an entrepreneur, you're a business owner, and you're dealing with employees, you know, and that is not always easy. I guess I'm curious, how, how have you changed maybe in two regards in terms of the way you think about hiring people and kind of what have your lessons learned over the trajectory of Hello Alice and then also how you manage people? Because I'm sure you've had some insights along the way. What are some thoughts on like 4 to 5 years in?

I know I've learned so much. I mean, at this company, I would say my last companies were very light on— well, my first company, no, no full-time employees. My second company was really light on, on full-time employees. And, you know, now we're a team of almost 100 employees. It's changed significantly. I think probably the, the biggest learning for me, one, I just, I feel like I've become a much better leader along the way. I always, you know, you look at things, I think when you start out, you look at it very much from how do we want to be managed? And you see the perspective of, you know, I dealt with a lot of managers before and I knew a lot of what I didn't like. And I knew a lot of what I liked, but I think when you start thinking from the other perspective, you're like, there's, you know, board pressures and there's financial pressures and there's, you know, you have to deliver and there's customer pressures and there's all these other things that you're trying to answer to that you can't always be 100% seeing things from the perspective of your employees and accommodating those needs. But the key is to be very direct about why you're making those decisions, be very transparent about why you're making those decisions. And I think early on it was try— I did a lot more of trying to appease, and Elizabeth would probably say the same. I think this is a lesson we both learned. We did a lot more trying to appease employees, and it became oftentimes a colossal waste of time where we actually didn't get them what they needed, and we also didn't get what we needed, and we didn't get what the business needed, and we wasted so much time in the process. And now We are certainly much more transparent. I mean, we have a lot more metrics and data and knowledge to, to guide us than we did back then. Back then it was a lot more, you know, you're leading by intuition and gut because there is no historical data to rely on. But I also think we're, we are much more direct and I would say much less soft, but in a way I actually think we have better relationships with our employees today. Than we did in the beginning. So it's, I think, eye-opening and, and, and then the way we hire, I think, has changed very much. We're really transparent about where we are strong as a company, but also what people may not like about us as a company. We, you know, we are often, you know, having to, to appeal to things that our, our partners need. Things are changing very much in the macro environment that impact the way that we operate internally. So a process that may work today may not work tomorrow. If you're someone who likes consistency and likes dependency, we're probably not the right place for you. If you like the new and you like innovating and you like problem solving, we're a great place for you. Uh, but we're very upfront about that. And in probably to a point where we're almost selling against ourselves sometimes in interviews, but I think it's important that people go in eyes wide open knowing what they're getting into. Yeah.

What are you looking for in employee and what are some questions you ask people to make sure they're gonna be the right fit?

I care way less about experience. I would say experience in the traditional sense. It doesn't— if I'm hiring for, you know, I don't know, a growth marketer, I don't care that they've had the title of growth marketer before. I actually want to know what have they delivered on? Do they understand the metrics at play? Do they— maybe they've done it with their own business. Maybe they've done it, you know, in another role, but they've touched on pieces of it. It's so much more about the ability to collaborate and problem solve and the willingness to jump in and figure it out. And I think for me, if there's a proof point or many proof points along someone's career that they've, they've built something from nothing, that's the piece for me that, that is most exciting. Obviously experience and, you know, having done it in that very relevant area is helpful and important and much more important in some roles than others. But more than anything, it's like, are you— do you have that like hustle and spark that you wake up every day and you're excited and you want to do a good job and you want to show up and you care about the people that you're serving? And I'll balance that with, I think where we've gone wrong also is when people are solely about the mission and don't understand the business side of it. We realize that's not the perfect fit for us either. Those are great employees for, you know, a nonprofit organization or for other places. We are a for-profit business, and at the end of the day, we have to make decisions that are going to provide a return for our shareholders. Mission is important, and it's a huge piece of what we do, and we're lucky that our mission actually drives profitability in our case. But we can't disregard the business side of it either. Um, and yeah, it's probably the two sides that we've kind of falter on is going on either extreme where someone's all about the business and they don't, they don't care about the mission, or they're all about the mission and they don't care about the business. We really need that balance of, of both.

Yeah, totally. And if I, if you were interviewing me, how would you kind of assess if I were like, had that hustle and that spark and that, you know, eagerness? And also if I could understand again the business aspect, what are some ways you would do that?

Well, one, I'd say you have it, obviously. I mean, I think having written a book, having a podcast, like you've done these.

Thank you.

You've launched things, right? You've created something from nothing and you've done it in a way that's— one, you've leveraged a network around you, you've brought these amazing speakers in, you have this community around you. And I think those are signs of evidence that you're not someone who just puts your head down and does the task that you're given, but you're actually creating the tasks and you're coming up with the ideas and you're executing on those ideas. And I think those are the things for me that I'm like, it's easy to come up with ideas. I have I would say I have way more ideas than time. Coming up with ideas is easy. Executing and taking a task is quite easy. There's very little in this world that is, you know, so complex that very few people can do it. The ability to take an idea and to transfer that idea into reality, I think, is a small group of people that have that follow-through, have that level of detail, and have the ability again to surround themselves with the the resources that it takes to get it done.

Yeah, totally. I love that you use the word evidence. I mean, of course I love that you're going to— that you want to hire me. We can talk about that later. Exactly.

I know.

Exactly.

I have it for you.

This is a recruiting process. I know.

I got it.

But I love the word evidence because that's what I'm constantly asking my clients to look for. It's not just, oh, they worked at LinkedIn, they worked at Facebook or whatever. No, no, no, no, no. What have they delivered? And to your point, the world can look me up and see what I've delivered, right? Because I'm a creator in that sense. And, you know, a resume doesn't tell you that. It's sort of the discussion that you have with people where they talk about what they did, what surprised them in that process, you know, sort of. So you really have evidence that they've delivered. And again, to your point, delivery being one of the most important things for you, and they have the hustle and the hands-on experiences. I really love that you said that.

Yeah, and it comes— I think the cool thing is it comes from everywhere. I mean, there's people all over that have that, and that's, I think, why I love the community that we've built so much at Hello Alice. But the stories of people that, you know, you could— you know, there's— I feel like there's a lot of times people, we fall into this trap as a society of, well, I've got all these barriers against me and I've got all these obstacles and I have all these things. And yes, there are certainly communities and individuals of all demographics who have incredible barriers that they're facing, some many more than others. But the reality is there is always opportunity and you have to find it. And the thing I always tell people, I'm like, people are rooting for you as an entrepreneur. They are. At the end of the day, they want to see you succeed, more want to see you succeed than fail. So go find those people that want you to succeed. Give them, show them traction, show them that you're willing to put the work in, ask them to open a door, like just keep keep going and keep going and keep going, and I promise you will find a way. You'll find a way to do it.

Yeah, I love that philosophy. I'm just curious, do you think any of that philosophy came from having kind of entrepreneurial parents and grandparents yourself, or, and/or your sort of, let's say, American and Bolivian roots, in the sense I know that you went back and forth as a kid?

You know, I always say I have kind of the best of both worlds in that I saw— and interestingly, my American side was actually much less financially supported than the Bolivian side of the family. For us, going to Bolivia is always like the treat, and we'd come back to the States and like we lived much more humbly. Ah, yeah, interesting. So my dad's path through entrepreneurship was much more difficult. Frankly, than my grandparents. What I got to see from my grandparents was how much a business could support a community. They had, you know, people coming up, the drivers coming up to pick up bread from the factory in the morning and delivering it out, you know, to these workers on the streets who would sell or into the stores. And to see kind of all these micro-businesses that had emerged from this one factory, to also see how they were taking those funds and they were educating employees and the programs that they set up for their employees. So that piece for me was just a great, like, really tangible way to see how business could sort of fuel a society. They were a pretty large factory, the largest, and it was kind of like the equivalent of like Nabisco for Bolivia. But it was a very successful business. My dad's company was, you know, started on a shoestring. He was supporting our family and barely making ends meet. The sacrifices that he made and the late nights and the stress and seeing that side of it, it made me realize like, this is hard. This is a hard journey. It's hard for everybody. My dad was a white male, college educated, and he struggled way more, way more than my grandparents who were Latinos in a third world country. And so I think the story on the surface, it made me realize the story on the surface is not, you know, we can't take those stories at face value and that Everybody needs support at some point in time, and it's not easy for anybody. And who we are certainly factors into the path that we're going to lead. But it's not— it's not everything.

Yeah, that's so— it's so wise. And I think it's such an expansive worldview for sure. We all have strengths and we all have kind of liabilities or disabilities. And I think our job to be successful in life and certainly in entrepreneurship is to use our strengths and to navigate around those disabilities that we have.

Everybody has them. It's attitude to me. At the end of the day, the biggest differentiator between those who succeed and those who struggle is attitude. And I get emails all the time from both sides. I got an email the other day from a woman who was like, I started my company in this country. I came to this— I came to the US with $300 in my pocket. She always had this dream that she wanted to start a business. She started a catering company in the pandemic. Obviously, it got shut down. She started right before the pandemic happened. She shut it down. Got a job. She's now back to catering, just got her first food truck, just got a great contract. And she's like, I did all this with the help of you. Thank you for the help that Hello Alice provided. On the flip side, I'll get an email of like, you know, I didn't get funding and I'm angry and here's all the reasons why. I'm like, of course you're not going to be successful with that attitude. Like, it's just two totally different mindsets, both hard paths, But the way that, that one is processing it and building, and the way that the other is processing and shutting down, the second one shouldn't be an entrepreneur. Like, it's not the path that's right for you. I'm sure there's other amazing skill sets that that person has. This is not the right path for that. And I think I always tell people, like, if you don't have that, if the no doesn't fire you up and the blockers don't motivate you to figure out a workaround, you are not an entrepreneur. And better to figure it out sooner rather than later. You can be broke, you can be, you know, in the worst environment possible. You can— you will figure it out. It's not going to be easy, but you'll figure it out.

I love it. I'm so fired up that you just said that. That's so great. You know that I agree with you that attitude is everything. And also many entrepreneurs, most entrepreneurs deal with imposter syndrome or severe self-doubt. Just a flagging of confidence. I know you had your own downfall of confidence early in your career, in your entrepreneurial journey. Do you have imposter syndrome? And if so, how do you deal with it?

You know, I've never really understood it, so I'd probably say I don't. I love it. I think I am a realist when it comes, you know, I look, I know I'm not capable of everything. I know I'm not without my flaws. But I truly believe in my ability to succeed. And I think it's a reason I went back to entrepreneurship is that I obviously didn't doubt it so much that I wasn't willing to try it again, but I wasn't so confident that I thought it was going to happen. You know, I would never been like cocky of the experience for sure. So I think it's like this, this balance of do I question, am I on the right path sometimes? And do I question my abilities at times? Certainly. Certainly. And do I take, you know, external validation sometimes is incredibly valuable. I literally just had this conversation on Friday after a call that we had, and I was telling my co-founder, I was like, I thought it was such a good call. And I'm like, that was like a shot in the arm that I needed. Like, I just felt like it like sort of revalidated what we're trying to do. And I think everybody needs those in all aspects of life at times, right? I mean, you're but parenting my kids. And sometimes I'm like, am I doing this right? I don't know. Like, what am I— what's going on? And then something happens, you know, some— someone comes out of the blue and it's like, oh, you have the most respectful, kind boys. And I'm like, oh my God, I'm doing this right. Like, it's, it's working. So we all need those moments of validation. But at my core, I don't think I doubt my ability to do it. And where I think I'm off track, I'm always trying to figure out how do I get back on track? Where am I off? What's not working? What doesn't feel right here? And how do I stop that and reinvent around it? Right. And I, I think it's kind of the same thing I was saying before. Like, this is to me, that's the DNA of an entrepreneur. Like, you're always looking to improve and iterate and make it better. So in moments, do I feel like an imposter? I guess maybe I was an imposter when I was trying to convince everyone my business was great and it was a hot mess. Then I felt like an imposter. But I was, right? I was out there like pretending to be something that I wasn't. And— but that was well within my control. So I always— I feel like it's up to me how I'm perceived and what I'm doing and how I feel about myself. That's in my control. Yeah.

Amazing. I love the agency. Just two more questions before we part ways. What do you wish, Carolyn, you had known earlier on your journey?

I definitely wish I had known how much you had to lean on others and how willing others were to support. With the right ask, how much people show up. I always— I still to this day, it's probably my biggest weakness is that I worry about being a burden or putting people in an uncomfortable situation where they feel like they have to say no. I am so thankful that Elizabeth loves raising capital because I would probably never be able to do it on my own because asking people for money, I think, is the hardest thing. I'll do all the prep work for it. I'll show up to the meeting. I'm happy to sell, but it's really hard for me to, to make the ask. It doesn't come naturally. I've gotten much better at it over the years. And I think had I known then what I know now, I would've made asks much earlier and, and much more directly than I did in those early days. It's been a, a learned skill for sure. Yeah, I love it.

That's so helpful. And what advice do you have for other founders as they embark on their journeys to grow into leaders?

Focus on the fundamentals. Um, Sometimes I think it's easy to sort of— we want success so badly that we kind of blindly believe that we're building something that's going to succeed versus being realistic about the fundamentals and, and not being afraid where things are failing and acknowledging it. There's always an opportunity to fix it and to redirect it, but the more objective you can look at those those metrics, the better you can build your business. And so look at the fundamentals of your business, understand your financial model deeply, understand team performance metrics well, understand, you know, what does your, your cash runway look like? Like really go in eyes wide open to those things so that you can make the best decision for your company. Bad, you know, I would say discouraging data is better than no data. Because at least it gives you an opportunity to react to it and, and manage it.

So true. It's easy to shy away from discouraging data, and it's also easy to be one of those vision entrepreneurs who's like not into the details, right? But it's actually ultimately, it's not sustainable.

I mean, entrepreneurs are optimists by nature, right? We wouldn't start a venture if we thought we were going to fail, is the reality of it. And so it takes a little training, I think, to go in and be like, okay, so with one of My favorite exercises to do as an entrepreneur is risk mapping and to write down every way a project can fail. What are worst-case scenarios? Let's go through all of it. And it almost becomes a game. You're like gamifying the experience of failure. But what happens is you start addressing it. You're like, all right, let's, let's take this biggest risk of failure and how do we mitigate against it? And what does that mean? And how are we proving whether or not we think this project should move forward? Because at least we're going to get there fast, there's a million other opportunities out there. If this one fails, we're going to move right on to the next one. And once that mindset starts going, I think it becomes— you start having really transparent discussions, you start really being willing to poke holes in your own projects. You're, you know, as a team, you build a culture of people critiquing each other and working to make everybody better versus this like finger-pointing fear of failure. Yeah, I think I really embrace failure. I'm thankful for that first because that's made me embrace failure in a way that I'm not afraid of it. It's not, it's not that bad, right? Once you've been through it, you're like, I can— I don't want to do it again, but I could do it again.

I love it. So realistic and so, so down to earth. Carolyn, what a joy to talk to you. I really appreciate your time. I appreciate the discussion.

And I know a lot of entrepreneurs are going to really benefit from this discussion. Likewise. Well, thank you for having me. It was fun. It's always fun to sort of wander down memory lane and remember what some of those, those early days are. I feel like, oh, I need to go. I need to go like take a minute. I feel like that was a lot of, a lot of those big, like, you know, cliffhanger moments of my entrepreneurial journey.

Yeah, well, they're good for your book, so we'll have to keep this recording for your book.

Exactly. Exactly. That's great. You can help me write it. Perfect.

Perfect. I love it. Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.