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Get ready as we explore the authentic and dynamic realm of entrepreneurship with Jennifer Ryan, the driving force behind Croux ( and the innovative founder of Blueroot ( This is a must-listen experience that will resonate with and inspire fellow entrepreneurs.


“Our focus was to look folks in the eye and try to solve a problem where we were, where our feet were, not what felt interesting to Silicon Valley or New York.”

– Jennifer Ryan


Podcast with Jennifer Ryan

Topics covered in the interview

Entrepreneurship, motherhood, and startup
Community-first approach
Exit strategies

Jennifer Ryan’s Bio

Ever pondered the heart of local economies? For Jennifer Ryan, it’s rooted in the intersections of food, work, and community. Born in southern California and refined in New York City and Silicon Valley, Jennifer blends global thinking with local action.

As the founder of BLUEROOT, she brought healthy, fast-casual dining to the forefront. Notably, BLUEROOT has been recognized as Alabama’s 2023 Restaurant of the Year finalist by the Alabama Restaurant and Hospitality Association, with the decision slated for 10/30. Jennifer’s efforts have not gone unnoticed, earning her accolades including a nod as Entrepreneur of the Year by Les Dames d’Escoffier.

But her impact didn’t stop there. With Croux, she’s transforming how the hospitality industry manages its temporary workforce, securing thousands of shifts for local businesses and empowering individuals to maximize their earning potential.

In essence, Jennifer is not just an entrepreneur but a visionary. With ventures like BLUEROOT and Croux, she’s changing communities, one plate and one shift at a time. Meet Jennifer Ryan – the catalyst of local economic change.

Follow Jennifer Ryan

Show Notes

Read Full Transcript

Susan Sly 00:00
Well, hey, everyone, welcome to a new year. And this might be your year. I know some of you secretly told me when I see you in person that you're thinking of starting a business. It's up to you. It could be this year, right? If not now, then when? You know how much getting ready to get ready, can you do? My guest today did just that. She moved from New York. And she, when you hear her, she's kind of like a New York girl originally from LA. And she moves to Birmingham, Alabama, and she opens a restaurant with no background in hospitality. And not only that, she has a brand new baby. And then two months later starts a tech company. And she is going to share with you the raw and real truth of what it's like to receive criticism and doubt, and this sense of loneliness, and how she transcended that. And so her two businesses, the restaurants called Blueroot in Birmingham, Alabama. And then she co founded a company called Croux, which is a tech company that provides services of bringing workers in the hospitality space to vacancies when there are seasonal vacancies or hourly vacancies, that kind of thing. And Jennifer Ryan is an absolute amazing person. And in fact, I'm going to disclaim this episode and tell you normally episodes are around 30 minutes, maybe 40. We go on for an hour, she is absolutely incredible. She was named Entrepreneur of the Year by Les Dames d'Escoffier. She has a background in venture and investment. And she's such an incredible human and a mom of a two and a half year old. You are going to love this episode and how she even shifted my mindset after all these years about entrepreneurship that comes in at the end. And you will want to listen to the very end. Before we get into the episode, a couple of things. First and foremost, thank you for being here. Our growth in 2023 was 50%, over, 2022 is incredible. We're in 166 countries and counting. And there's so much going on in my life. And I love that you are al,l are all amazing support. So I have launched a new company called TPT. And it's How you can support me is if you are a woman, you can go to the site, you can sign up to get tips on perimenopause, menopause, the tech platform is being built. And then we will welcome you with open arms to use our gamified AI driven menopause navigation tool. That's a mouthful. That's why we call it TPT. And, you know, if you just want to check in with me and be on the list, that's cool, too. And so that is coming. That was a big step for me as I changed my career and pivoted from being a co founder to a founder and a CEO. So that is going on something in my personal life. And it's going to be a great year. We have incredible shows coming up, we have amazing guests. And please do follow me personally on social. On Instagram @Susan sly, on aX it's @Susanslylive. I'm on LinkedIn, obviously. And then please follow the show channels and subscribe to Raw and Real Entrepreneurship because you do not want to miss an episode. So with that, let's go ahead and get started with my interview with the founder of Crouxand the owner of Blueroot, the amazing Jennifer Ryan.

Susan Sly 03:50
This is Raw and Real Entrepreneurship, the show that brings the no nonsense truth of what is required to start, grow and scale your business. I am your host, Susan Sly.

Susan Sly 04:04
Well, what is Raw and Eeal entrepreneurs wherever you are in the world, I hope you are having an amazing, amazing day. And as you heard in the intro, that you know, this guest is incredible. Not only is she a multiple founder, defied the odd in hospitality and on top of everything as mom of a two and a half year old like we could do a whole show just on that. But Jennifer Ryan, I want to jump right in and ask you this question. What is it like navigating a startup and a two and a half year old and recently, six months ago you just moved to Green Bay, Wisconsin, like how are you navigating all of that?

Jennifer Ryan 04:45
You know, I would say some days better than others. And it's the old adage that it takes a village, right? My mother told me this. I've got two sisters and a brother. I've got a dad who's supportive. I mean, I've got this family around me, an incredible partner in crime in my husband and a broader network. And I have found myself resisting what comes naturally, which is to do something by myself to do it on my own. And I've leaned into being okay asking for help, and asking for support. And I truly am indebted to this group of people, friends and family alike who have supported us in this move, having a baby, having a baby while launching a restaurant, and then a tech startup. And it is just as I've learned with entrepreneurship, it's not a solo venture. And the moment that I can be super clear about my blind spots, or my perhaps areas of growth, I, the faster I can identify those and lean on folks to help me either get stronger or to provide some support in those areas. I think that's what's allowing me to do all of these things. Because I certainly wouldn't be able to do it alone. So it takes a village, I think, is the is the true answer. And then I think the other real and raw response is, there's some really ugly days, and some really ugly moments. And it's not always beautiful. And I remind myself of that as I scroll through social media, or as I read an article about, you know, another female founder, who's got many children and has all the other balls in the air. And those stories of perfection are just not the real reflection of what's happening. And so I think saying it out loud, it's okay to have rough moments and rough days. And it's okay to have the lows. And I think you know what, I'm just taking it all in stride, and recognizing it's part of the journey. So it's not always pretty, I think is the real answer.

Susan Sly 06:33
Yeah. When you, when you say, you know, you have those rough days, the challenging days, and I think about for you, because I, Jennifer and I were talking about before we went into the show, and the listeners all over the world, I just tell you all everything, so then there's nothing to hide. So we're contemplating leaving Scottsdale. And I said to my husband, we've been here for 10 years, I said that my network is here. And he's like, your network's just a few people. And he listens to every show. It's always going to be like you said that? But it isn't just a few people. It's VCs, it's talented tech people. It's my, you know, support network when I'm having those challenging days. It's my girlfriends I go to yoga class with. Was it tough to uproot and move somewhere where you didn't have a network? And how are you navigating that?

Jennifer Ryan 07:30
Yes, it was really hard. And it is, it's the second time that we've done this in the last decade. And my husband, who is incredible on so many levels, feels a deep responsibility, because it's his job that's taken us to new places, where we have no friends, no family, no network, no community. And the first was Birmingham, Alabama. I'm from California, I was living in New York City. And we moved to Birmingham, Alabama, where we had no connectivity whatsoever. And I have to say, on the other side of it, seven years later and now Green Bay. Those years in Birmingham, Alabama, of all the places, was probably the most formative chapter of my adult life. And I think it was because a few things. We decided when we got there that we were going to really live there not just exist and skate on the surface. And I think that was the most important thing as a family that we just decided to, you know, really dive in. And the second thing I think, was we, we really leaned on each other. And it was really important in our relationship to, we just got married, we didn't have kids yet. I mean, just really learning what we needed, improving communication, all those things that perhaps they were just a bit expedited for newlyweds. And it really forced us to go deep and ask ourselves, what we cared about, and what our values were, and how we spend money and how we spend time and who we spend time with. And those things didn't happen organically. We almost really needed to cultivate each of those, be super intentional about it. And I look back on that, it was a foreign road. But the movies playing out again. So here I am six months into another move to the Midwest where we have no friends, no family, no connectivity, no network whatsoever for his job. And what I learned from the previous move, was a couple of things, but most of which is its mindset. And we went in glass half full, we went in with optimism and open arms, we went in with an openness and a gratitude to newness. And change is really hard for most of us. It's really hard. But I think for us it was the mentality and the perspective of appreciating that it was not happening to us. It was happening for us. And it was a gift that we were able to go see a different part of the country and live in a different community and meet new friends we never would have crossed paths with and that there is nothing different. We are moving regardless. But it was the perspective, the lens through which we decided to look. And so I'm lucky to have a partner that believes in that, and has the optimism and the gratitude. But I really, I will admit to you, since you're so real on this show, there were many months where my response was not one of a supportive spouse. It was not pretty. And I'm not proud of that. Because it was a selfish response. What about my business? What about my friends? What about what I built here? I did this already, you know, and so I had a choice to be resentful, or to recognize that setbacks might be set up for something new. So I'm working on it. But it is really hard. And it's required a level of intentionality that came with, you know, practicing this once before. So I'm trying to get it right.

Susan Sly 10:54
Yeah. And I think about when you, you know, coming from New York, I'm originally from Toronto, it's like, there's a very similar intensity there. And then moving to the south, and then looking at the businesses you've started. And it's, it's really beautiful, Jennifer, because there's a warmth to all of them that really seems to have that, that southern hospitality that you know, they talk about to go from New York, which is like, I'm all about me, I don't want to talk to you, too. Like, I always say the difference between the North and the South is like me versus we, right? Like or with some states, and now you're in the Midwest and very similar. And so from being in Alabama, what is it that you have taken, that you've learned there, and it's permeated into everything you're doing now? Because I can see it so clearly, after interviewing hundreds of entrepreneurs, and I love it, but I love you to share that with the audience.

Jennifer Ryan 12:01
Sure. I'm curious as to what your answer is knowing a bit of our story and having the perspective of having this type of conversation so many times. Here's the through line now that I'm not on the other end of it, I'm in the midst of it. But I have now launched two businesses and they couldn't be more different. They're both high risk and take a ton of time and capital. But one's the restaurant and one's a tech company. And I think what I tried to bring was a perspective of living in big places like Los Angeles or New York City. And recognizing when I moved to somewhere, a tertiary city like Birmingham, and now Green Bay, that there are a lot of wants and desires and interest in innovation and new ways of thinking in these places. But there isn't necessarily a lot of investment. And so the question I asked myself was, were there learnings from my previous experience that can be translated to a place and appreciate it, right? I'm not gonna build a business that people don't want, right? I want to solve a problem, not push a product. And so when it came to the restaurant, it was leveraging learnings and experiences that I love that I thought, well, maybe there are other working parents that are looking for healthy food like me, but don't have the instant accessibility that I can find, you know, a salad or green juice on a quarter like you could in New York City. Maybe there's an interest in that. And the same was for the hospitality industry with Croux, is there a way for us to leverage technology in a new and novel way. And so trying to bring some learnings, but most importantly, I think what I learned was, there's no manufacturing from the outside and putting it into these towns. It's gotta be homegrown. It's got to be organic. And it's got to have the community and the local economy, first and foremost, on the priority list. And I learned that, and I knew that it wasn't about bringing in a brand that I loved, it was about recognizing what was important to the people around me and building what was useful to them. Because we weren't in New York City anymore. We weren't in Los Angeles anymore. We weren't in Atlanta, we weren't in Milwaukee, we were in Birmingham, we're in Green Bay. And so recognizing the people, the humans. And for me, the humans in hospitality, and, and figuring out if we could support a local ecosystem first. And I don't subscribe to the if you build it, it will come because I think you need to do your research to make sure that you're building something that will support the community. But we had this notion that if we built something even so small, that it impacted just a group of people, you know, in a very limited orbit, Could we impact that, you know, small, you know, micro community and in turn start to through job growth, tax dollars, you know, continued, you know, requirements of leaning on other people that can do that did things like legal and compliance and accounting. Could we start to really fuel an engine here? And that's what we did. We built small and earned trust, and really were able to grow from that and so it just started with the local, and now, you know, living and leaning on local is very in vogue. But it wasn't always, right? It wasn't always. And so that that was our focus was to look folks in the eye and try to solve a problem where we were, where our feet were, not what felt interesting to Silicon Valley or New York. And I think that, that has paid off.

Susan Sly 15:21
To your point there was a time when it was, oh, let's bring the New York Business to Birmingham. I've been to Birmingham a couple of times, so I can speak from that place. Fun sidebar. I you know, everyone has their 15 minutes of fame. So I'm very, very publicly passed out on ESPN doing the, the Power Man in Birmingham, and I was out there with a lead pack of girls, I don't even know what year this was like, maybe 1998. And I was a pro do athlete and I was running, running, running. And I totally collapsed. I had shingles. I didn't know I was putting on all of this, you know, Benadryl cream and stuff. I thought it was rash. And I just passed out on ESPN. Anyway, so that's Birmingham. But everyone's lovely.

Jennifer Ryan 16:12
Other than that.

Susan Sly 16:13
Other than that, other than that. So, there, Jennifer, I read a statistic that 70% of Americans think about starting a business but less than 7% ever do. So what gave you the courage to go, I have this idea for Blueroot, but I'm actually going to start it?

Jennifer Ryan 16:30
So I, by the way, not to throw a question at a question, but I wonder what percentage of that 70% is women? Because I'd venture a guess, pretty limited amount. You know, we were talking about this a little bit of where do you, where do you conjure up the confidence to do something you've never done before, it's such a hard thing to jump off a cliff. And mostly because, we're getting better as a culture, but mostly because the notion of failure is that big scarlet letter that nobody wants to wear, you know, and we're, we can talk, I made a lot of mistakes. But I think that's really what holds people back, what happens if. And so I approached it a little bit differently. I had the good fortune and grace to have 10 years working in an investment bank under my belt. So I felt like I had a fairly good sense of the nuts and bolts of what I needed to make happen. I had a fairly good understanding of even just what financial I was going to need, and how to even read a p&l. I also think the thing I learned after, you know, 10 years of working, was to get really clear again, with my blind spots, and be really, really self aware of the areas that I knew I didn't have a muscle to flex. And I was at a point in my career where I wasn't going to go out and learn through those things, I was going to lean into what I was really good at. And so I have to admit, I wanted to bring a big box brand from New York City to Birmingham, because I didn't want to start a restaurant. This was a selfish endeavor. When I was on the move, traveling, I really wanted to start a family. It was a terribly difficult process. And I was trying to take care of myself and eat good food while I was working a weird, crazy job. I wrote manifestos to all the brands you'd imagine and beg them to come to Birmingham, giving them statistics and information and data and telling them that it was so compelling, they couldn't pass up. And the truth was nobody answered. And so the question I had in front of me was, Do I just let this lie? This is now my home, I'm gonna be here for the foreseeable future. Or do I do something about it? And I think part of me was, it was a bit of naivete, coupled with a certain understanding of where I knew I was good and where I knew I did, I needed to have some help and the naivete was maybe what was part of it. And I think that's part of entrepreneurship of it. But a lot of it was the courage to put it on paper and saying something out loud, to my husband, to my friends, to my family, made it real. And then I gave myself really, really meaningful, impactful, but simple milestones to hit. And I told myself and my husband, I'm not going to just spend our life savings. these are what I need to hit and if I don't, it's an easy off ramp. So I always felt like I had a good plan versus diving off a cliff without, you know, any gear. I really felt like I had, you know, whatever tools I needed to either, you know, keep going or to take a left turn and say, Okay, I tried, I really did, I gave it my best my best shot. And so by setting up two things, the milestones, so I knew at certain periods of time, I wanted to see these markers hit and recognizing my blind spot, so leaning into others that had you know, the expertise of the acumen. I knew I had some guardrails in place. I knew I had somebody checking me on areas I was, you know, really not very strong in for me running a restaurant. I did not have a culinary background. I cook all the time, but I did not have that background. And the rest of it was really a timeframe. And the last thing I did was we drew out as a family the worst case scenario. Are we comfortable with this? Can we do this if all of our wishes you know, disappear and nothing works? And to me putting the hardest piece which was failing on paper, made it real, and almost, you know, for lack of a better word stomachable. And so that's how I got over that first, that first hump was really, you know, really trying to clarify, articulate an outline, but it was work, you know, really, really did the work up front. And it's the whole adage of measure twice, cut once. And I think that's what allowed me to be able to do something I had no business doing, right. In addition to asking for help, and leaning on great advice, and having wonderful mentors and all the, all the infrastructure around, but those were a couple of things they did internally, to make sure that me and we as a family felt okay about it.

Susan Sly 20:36
Well, restaurants of all businesses have the highest failure rate. But I love what you said, you had an easy off ramp, In the hundreds of interviews I've ever done I've never heard that before, I had an easy off ramp, we did the worst case scenario, and I knew that there were just multiple places, this highway where I was, you know, wanting to go but I could exit any time. And the risk was, you know, relatively low, compared to what a lot of people do is they they go for that destination and they keep borrowing money, borrowing money, borrowing money, and they're in over their heads. Right, Jennifer? And then they, and then, and then they're laying you know, then the whole business collapses. So this, starting the restaurant, and with no culinary background, I mean, having a business background, I have friends who have restaurants, and they're great chefs, but they do not have a business background. And so when you said you had no business starting that restaurant, I would say you had more business starting the restaurant than a great chef. You can always find someone to cook, but someone who understands the p&l, who understands how to do the projections. Glenn Stearns, who's been on the show a couple of times, that when he, on Undercover Billionaire when he started Underdog Barbecue, Glen wasn't a restauranteur. Right? He had 90 days to create a million dollar business. But he was the business person, he knew like you, how to gather the right people. I want to talk about Croux. Because there are so many questions I have for you because the the number of startups in the United States that are tech startups that have at least one female founder is, let alone a CEO, is less than 2%. It's incredibly small. And so what, here's what VCs would say to you, but you came from this world so you know, and you're New York, tough and LA tough. And they would say, Well, you already Oh, Jennifer, you already have this restaurant. Now, It's like what business do you have starting a, you know, a tech business? And so going from having the restaurant to starting Croux, What were some of the criticisms you heard?

Jennifer Ryan 22:55
Yes, I mean, I have, I mean, the number one for me was you, you have your hand in too many pots. Right?

Susan Sly 23:04

Jennifer Ryan 23:05
And I think there's a, look, there's a lot of value in listening to criticism and a skill that I've tried to hold on, and I'm still working on it is really filtering out the noise and trying to hone in on feedback that's actually really helpful. And I'm not saying all of it is and I'm not saying you should cast aside, you know, take all feedback in or cast all of it aside, but really trying to filter through and understand are there threads here that I keep hearing, what really is it that is precluding somebody from investing, in supporting, you know, whatever it may be. And so I heard that, you know, you can't do both. And I actually do subscribe to this philosophy of being more focused and sharp shooting and you know, a bit more of the sniper versus the shotgun. You know, not spreading yourself too thin. I tried really hard, even during the day to focus on a task versus context switching. We know that's really hard on the brain. So I actually really subscribe to that. But the reality was like, I had this restaurant, and I also was a mom, and neither one of the things was going away. So I either could capture and seize this moment, or I can let it pass me by. Right. And that moment was, it really came to us as the great resignation was taking this country and the world by storm. And we were in a really unique position, as you know, five founders, one technical software engineer and for hospitality people that were living and breathing this every single day. And I decided to seize the moment, and I decided to push back. VC said, we will never ever, ever see investment in you because you have more than two founders, it's never gonna happen. It happened. Right, you will never be able to be successful because you have two new voices around the table. Well, you know what, I think our team is actually our strongest asset. So a lot of this, you don't look like what we've seen before. We really had to either dispel the myths or just be comfortable with the, you know, the bullets that were flying, and really lean into the conviction that we had in not just the technology, but our philosophical approach of putting the humans first, right, like trying to lean into this notion of supporting the humans in hospitality. And I'm still combating a lot of that but I now have, you know, a couple of reps, a couple of wins and some funding under my belt to be able to say, I hear what you're saying but I'm still confident in our approach. And I'm just, I'm gonna politely disagree but I really appreciate you, thank you for your feedback. And sometimes that's all you need to say, thank you for your feedback, right? And take it and bank it. But I really am trying hard to listen. I think some of the, some of the questions were also on, you know, I don't have technical acumen. Right. I worked in cybersecurity, but really on the strategy and operations and finance side, I'm not an engineer, What business do I have running a tech company? Right. And last but not least, you're in Birmingham, Alabama, like get yourself to New York or Silicon Valley so you can really play with the big boys? Well, you know what, I'm not moving to Silicon Valley or New York, I'm actually moving to Green Bay, which is a smaller town. And we're still, and we're still going to be successful. And to really again, pushing against, again, what I call, you know, some of the norms. So goes back to conviction, confidence, perhaps a little naivete. But now in the second round, the difference here is that I've got this team, right, I really have this arsenal of killer, killer experience, instinct, execution. And that's what makes us unstoppable. But you know, those people that said, You're doing too many things, you know, they're right. And I am not running the restaurant day to day anymore. It's still mine. But really, I wanted to choose and lean and hard. And my little one, she's my priority, my family and getting this tech company to the place I know it can be. So I'm still navigating the feedback. But you know, look, I worked in, at an investment bank for 10 years, and there were very few women, the ratio was very much slanted against us.

Susan Sly 26:43
You're from New York anyway. So you know how to boomerang. I love that. I love what you said, Well, yeah, we may look different, but that's our asset, not our lives, I'd like you know, you go girl, like just-

Jennifer Ryan 26:54
You gotta, I guess you just gotta get comfortable the criticism, because particularly female entrepreneur, like it's just gonna come, like, there's just never going to be a world in which it doesn't happen. So I don't know, the thicker the skin the or, and also just let it be porous enough to listen to the good feedback, but let the rest of it just slide off. And just, you know, surrounding yourself with really good people. I've got mentors and advisors that are helping gut check me, you know, I need to listen to this, you know. So I think it's what it comes down to really again, it goes back to that village. So-

Susan Sly 27:19
definitely, and the, I love that you said that the, so for my new startup, the one things I've been doing is, is going for lunch with VC friends and reverse engineering it from before we've taken on one investment, and just saying, if we were going to go to an A round in 18 months from now, let's reverse engineer it. Here's what our deck looks like, here's what the plan looks like. This is my customer acquisition. This is why I know I can hit this target. Here's why it's actually a low target for based on what I know I can hit. And I was having lunch, Jennifer with one of my VC friends who's a mentor of mine. And he said, No, this is, this is it, this is, there's only one thing I would do differently. And, and it was great because they have their, to your point, they have their checklist. And, but there are new funds emerging. My new startup is in menopause tech. That is a new category. I'm on an airplane and I love what you said Be intentional, like you, you know you have your ethos, you're intentional, whether it's affirmations, whatever it is. And I'm coming back from seeing my dad who's not well, and it's a five hour flight from DC to Phoenix, and I sit beside this gal. And one of the things she does, she has one of her funds, they only invest in menopause.

Jennifer Ryan 28:39
Like what?

Susan Sly 28:40
I girl, I'm not even kidding you. And so-

Jennifer Ryan 28:43
What are the chances?

Susan Sly 28:44
Yeah, she and I, by the time this show goes live, she and I will have had dinner. And it's the same conversation. I won't disclose her name, but it's like, this is what I'm doing. This is the plan. This is why I know, like, my zone of genius is b2c, I've done b2b when I, you know, was the CEO of Radius, I know how to bring in the big deals, I know how to do recurring revenue, but this is our plan. And here's the thing I would say, because I invest in tech is I would look at you and go, actually, she's more qualified than a data scientist or an engineer because girlfriend owns a restaurant. And if you look at what Croux does, and it's human first human, you know, oh, in hospitality, what business does someone have building that business if they don't know hospitality? So I would say you're actually more qualified. You would be for, as an investor, I give you a much higher priority than just yet another me to company that has a data scientist or an engineer at the helm. That in my opinion.

Jennifer Ryan 29:43
Well, I appreciate that. That's a very unique perspective. But to your point, I've had to lean in time and time and time again to different is not just good, it's better.

Susan Sly 29:54

Jennifer Ryan 29:54
And that like whether I'm you know, applying for a job or starting a company and different is really differentiating. And some people get that, and some people, and that's okay. They're just not either the right investors, they're not the right partners, whatever it is, but we're all about innovation. And we're all about changing the way we do things. And to me, one of the hardest things to really wrap my brain around, is when we keep doing this something the same way. And it's there's a more efficient, more interesting, more compelling way to do it, whether that's a different paradigm of what a CEO and a founder looks like, a different background, a different approach, you know, more innovative philosophy, different, I've learned is really the superpower. And having a unique perspective and a background that, my resume does not make sense on paper. It absolutely does not. But I think, you know, when I've talked to a lot of younger, particularly women, but younger people that are trying to figure out how to, you know, land that next job, you know, putting your resume in front of somebody, that's not very interesting, but being able to tell story about what you glean from somewhere that you're able to, you know, translate and give to your next opportunity, that's what's interesting. And that's where I really tried to sharpen the sword for me personally, because I know I'm gonna go into gunfire, I just know that I'm prepared for it. You know?

Susan Sly 31:08
Yeah, absolutely. It How did you get the initial funding for Croux? Because the tech startup isn't free.

Jennifer Ryan 31:15
It's not, it's not. Okay. so this is one of those, call it serendipity, call it coincidence, call it God, call it the universe coming together, I now have learned over many years, you got to put yourself out there, right. You got to say what you want, you got to be really clear and intentional about it. And you've got to say it out loud. Because then your network, whether, you know, implicitly or explicitly, your network can help. And so I sent a bat signal, when we were starting Croux in Q4 of '21, when the world is falling apart, and you know, everybody's restaurants were closing. And you just remember that time, I had, I had a baby in May, and then launched a restaurant eight weeks later, when I would never recommend that to anybody. And then two months after that, we started the tech company. And when we were thinking about what we're going to do, we put our own capital, and there were five of us, there are five of us, I should say. And we really wanted to get some reps under belts, make sure that it was, you know, fruitful. When we decided to go out and look for capital, we went to our community first, like the people that understood what we were doing for Birmingham that people that, you know, went to the restaurants, the people that were supporting the industry, the people that were, you know, interested in seeing technology become part of the fabric of this town. And that's why don't we went to other humans. And we didn't go to institutional capital, until, in a very serendipitous twist, my husband got a job opportunity in Green Bay, Wisconsin. And in this process of, you know, meeting people, figuring out if we were going to move, I was casually introduced to a small VC firm, that has a joint venture between the Green Bay Packers and Microsoft. And it's based in Green Bay, Wisconsin, and it's called Titletown Tech. And that introduction would never have happened if the What the heck moment we're moving to Wisconsin had never happened. And so this is one more reminder to me, to be open to change, to be open to twists, to be open to turns. And Titletown Tech led our round, we had a friends and family around the close last year with people locally from our Birmingham community. And this fund that is investing really in the Midwest, in companies like ours, that are changing the game of how companies operate. And that was very, very special and very unique. And, you know, Titletown has, it's a VC, but it acts in a much more human capacity. And it was the right fit for us at that early stage. We were really trying to find our footing. Clarify our story, um, you know how it is, in the earliest days, right, you know, had this thesis, you've got promise, but you've got to go prove it. And you've got, you need a little leeway from your investors to just have a minute to go prove that you can do what you know is possible. And they gave us that moment. And now here we are, we filled 10,000 shifts in the last year. And we're in seven markets, and I've got this incredible team and we're gonna be profitable this year. I mean, who knew? And so-

Susan Sly 34:08
That's fast? I mean, let's, let's pause for a moment. And like, have, you know, the champagne moment, like profitable in a tech company in two years in the hospitality space? Like, let's just like, there are so many things, Jennifer, that that's just like, you know, if you, if you said that you know, two years ago, I'm going to build a company. It's gonna be profitable in two years in the tech space, and I've never been a tech founder, and I am going to have a baby. So I have an infant, and then who's going to become a toddler who gets into everything, and I'm going to do all this. A lot of people would have said, You're crazy, like they would have, they would have nodded and smiled and then the door closed. They're like, she's never going to do that. And I personally love that, She's never going to do that moment because oh man and it makes me like, you know, it fuels me.

Jennifer Ryan 35:04
It does, I completely agree with you. And you're right, I probably would have had a moment of pause too, if that's the track, you would have projected for us. But we launched, you know, in, really, we've been around for a year, and we'll be profitable by the end of next year. And you're right that the 24 months. I mean, look, we can dive into that, to your point is a whole nother show of how we, how we're going to get there. And why I think we can do that, and why the projections are conservative and this than the other but the fact of the matter is, it started with surrounding myself with the right people, having the right team, it then progressed to bringing the right investors in. And you know, what the best advice we got were raising capital was not all money is the same, you know, people say it's green, it doesn't matter. You know what, you know, this, it does, because those people are attached to you for almost a decade, if not longer. And so they've really got to be in the family and in it with you. And so really, we're so early on, but I really feel like we were very intentional about who we brought into family. And, and that was part of the story, you know, it's fueling what we knew as possible. But it's still climb, right? I'm right, you're, today is a day where I'm writing on a high, right, we've really had a lot of milestones, we have an incredible q1 planned, we have expanded into new places, we have this wonderful team, there are deep dark lows. And I know there are right around the corner, because this is just how it works in the worlds of running a startup. And so, you know, really trying to lean into when we're writing on the high end, be grateful. And it all started with a couple people believing, right. But it started it goes back to that. Even if cheesy notion of starting local, right, we went to the people in our community. And that's where we started. So-

Susan Sly 36:39
and that is huge. And that goes back to my question for you about the network, the thing that scares me the most of anything, moving away from my network. I have like a, I mean, a vast network, but moving and it's like, oh, okay, you know, whether it's something little like, oh, I go here, I get my hair colored, or I'm having my wall kicking moment, I pick up my girlfriend, we meet, we have, you know, we go for dinner. Or my VC mentors or whoever it is. And that is something that, you know, always being able as an entrepreneur, I would say, of the hundreds of interviews I've done, there's one common theme is that entrepreneurs who make it know how to build their network. I want to ask you, how did you set your early valuation for Croux? Because that is such a, that is just an interesting concept for so many startups, how they get there?

Jennifer Ryan 37:32
Well, I wish I had a more formulaic and scientific answer for you. It's a lot of this right, in those early stages. And we did a bunch of work. Now, to put it in perspective, the world has changed so much in the last, when we we came together in 2021 in Q4. And it was still when valuations were out of control. And there was tons of money moving around. And that has really corrected itself in the last, you know, 18 months to 24 months, right? And, and so really, when we set that valuation, then we, we did some homework, we looked at competitors, we better understood what the landscape looked like. And we really thought a lot about what we can build. And then we got checked today, you know, across a few different, a few different resources. And I'm not sure that it was right or wrong. I think, you know, the people continue to remind me, it's not gonna be perfect. And right now, what you have is an idea on paper. So really whether or not that was the right answer is isn't I don't know. But we did set it. It was part of, you know, the friends and family rounds that we did last year in our convertible note. And it's there. And so the question for us now is, you know, two years later, I guess, a year and change later, Do we do it? Did we do what we said we were going to do? And the answer is yes. And so now as we recalibrate and get ready, most likely for a larger raise in '24. You know, I think that'll be a bit more of a straightforward exercise. But I mean, it was one of the hardest things for me as a founder, I've never done that. I didn't have to do that with a restaurant, you know. To be totally transparent. I took out an SBA loan for the restaurant, because I knew the failure rates of restaurants. I didn't want to bring anybody down with me if we went down in flames.

Susan Sly 39:10

Jennifer Ryan 39:10
I just didn't. And that goes back to, you know, the notion of learning how to ask for help and learning how to, you know, bring people into the fold, I just wanted to fail alone. And here we brought investors in. So there's a bit of trust in that process, as well as trying to corroborate the data with as many people as possible and kind of get the same answer. So I'm not sure. Is there a playbook for this that I missed, by the way?

Susan Sly 39:33
No, it depends on the year. I love how you you know, II said like, which way is the wind blowing? Right? It depends on the year for the valuation, depends on what is in the company, like you know there's, so many companies will say, Well, I'm an AI company and in '21 that would get you like even a pre revenue valuation that was, you know, even just, you would just start and be like, Oh, we're at 20 million valuation, right in dollars, money. And now that has changed, it has contracted, but then given what is going on in the economy and what the Fed is saying, and then I'll give you an example, I have a friend who's a VC, they were going to deploy 90 million in capital, in 2023, they did one investment, they didn't deploy it. And they're waiting to see what the economy is doing. But at some point, they're going to have to deploy capital, a lot of VCs are like this, they're holding back, but their investors are expecting them to deploy because if they're sitting on the money, and you know this coming from your background, the money is depreciating in value, because it's just kind of sitting there, whether it's in you know, even if it's in some kind of term deposit, just based on the inflation rates. So there, I predict and I, my mentor always says give a percentage. So I'm, I'm, I'm very bullish on next year, unless there's, you know, more global uncertainty. There's another pandemic or something, God forbid. But I think there is going to be more deploying of capital. But what a lot of VCs are doing, It's like a mash up. You know, when you take two singers, this used to be a trend several years ago that have, you know, it would be Oh, it's like when Martha Stewart and Snoop Dogg Got together. Yeah, that kind of mashup. So what VCs are doing, is they invested a conflated valuations in tech companies. And now those companies are doing down round. So they look for startups that can actually work synergistically with those tech companies and boost those companies back. And I think we're going to see a lot of m&a activity. You know, I wouldn't be surprised if Croux is on several m&a lists right now. There are other, there are companies I know that have tried to penetrate this space, they didn't expand like you did. And that's why I said, you know, kudos to you, my friend, like starting local grassroots. I talked to another founder, she bought out all of her seed investors, because they didn't get the vision. And she's like, I've decided I don't want any investors. And I'm thinking, God bless you. But at some point, you're going to need to scale and you can't scale a tech company unless you're sitting, maybe she's sitting on hundreds of millions of dollars, I don't know, I don't know. But you will need to scale to your point. But I see very clearly, where you have a very clear path to m&a or IPO. Have you thought about it? Or do you want to disclose that, like m&a, or like IPO or acquisition?

Jennifer Ryan 42:35
You know, I think, I think all of the avenues are on the table, not to sound so cagey. I think all the avenues are on the table. And for us, we're still young, that I can envision a lot of different exits, a lot of different outcomes. I think, with the space that we're playing in, so there's the, we try to get super specific. And by the way, just to comment on one thing you said, I'm also bullish on next year, my projections would read otherwise, because I have tried to keep things pretty conservative in just in case, you know, to make sure we've got the runway to make sure that if, God forbid, we can't raise or whatever else, like we still get to the point of profitability. But I do think we're gonna start to see a lot of capital unlocked. I suspect there's some conversations about rate cuts. I mean, there's some things macro economically that I think are going to encourage that those funds to flow. And there are folks like us that I think have not been overvalued, that are ready and willing for the right partners, right, and the right capital. All that to be said, when I think about you know, flash forward several years, we've chosen to play in a very specific space. And I commend my team for a really, really sharply focusing on both the industry that we're focused on, I mean, I get asked all the time to lean into manufacturing, into agriculture, and to all sorts of other spaces because the technology is applicable. I know we can get there and we can grow. For better or for worse, Susan, we've decided to say sharp basically do the sniper approach on the hospitality industry, but also in these markets that are under loved and flyover zones, the South and the Midwest. A lot of our competitors play in the big places that you'd imagine. And I chose with my team, we chose not to play there right now. We make it there at some point. But we're playing in a very specific industry in a very specific geography. And I imagine flash forward, that could be an interesting puzzle piece for a big company that doesn't want to build it out themselves, right. And so I imagine at some point, in five, six years, somebody turns around and says, we forgot about 30% of the country that needed us. And we decided not to innovate and invest there. But you know, what Croux did, because we believe in supporting these communities that are looking for a lot of the innovation and investment and interesting things that are happening in some of those big cities that you and I don't know so well. So that could be an off ramp. And I also imagine if growth continues, you know, we could be in a really interesting position to be on the other side of m&a, you know. So we're open minded, I think what we're trying to do is really keep our eye on the ball. And I don't, as a founder, it's hard, you've got to be acutely focused on what's happening day to day. But you also have to keep the team's vision so clear, keep the dream alive. And toggling between those two is a skill I'm really still trying to work on, you know, because you can get mired in either one. You can be too detached from the day to day, and not understand how you need to be pivoting or, you know, navigating. Or you can be so mired in the details, you forget where you're going. And so keeping those end game options open, while recognizing that the only way any of those avenues is open to us is if we deliver today. We've got to deliver today. So we've got big, big dreams and big goals. But at the end of the day, my job is to make sure the trains on the tracks, and we're doing what we've promised ourselves and our investors we can do, you know. And we've got a really clear, you know, 12 to 24 month view of what that looks like. So I hope, like many of these moments in my life, the hard work, the perseverance, the planning, puts us in a position of opportunity, whatever that looks like, and who the heck knows what the opportunity looks like, in 12 to 24 to 36 months, you know. What, what could, how could we plan for the last few years? Right?

Susan Sly 46:14
And, and even. And even the next, the next 12 to 24 months, right? That I just, I was at a, I was invited to this think tank called Humans First. And we're, there's a group of people and you know, the we're sitting in this like room, and we're discussing the future of humanity and AI and different perspectives and things like that. And I said, How many of you have heard of chat GPT, 18 months ago? And they're like, none of us. And I said, so we can't predict, you know, the next 12 to 18 months. But here's what we can predict. We can predict resilience and grit of humans, we can predict that, you know, for certain industries, people still want to eat, they want to connect, they want to do that. And, and so I, it's evident to me, Jennifer, your trajectory, and if I was just sitting in a room, not like in this global living room that we're sitting in, I would look you in the eye and say, I love that as a founder, you're like, six, seven years, I'm going because that's you know, that's necessary. I think your off ramp opportunities are gonna come a lot sooner than that. Just, you're a very rare founder. You get the numbers, you understand what it takes, you get the, you have the humility to know what those blind spots are. And that willingness, and it's rare. So yeah, I'm, I'm excited to to watch this journey unfold for you.

Jennifer Ryan 47:47
Oh, I'm so grateful for that, you know, it's how lonely you know this, because you've done it. But how lonely it can be when you're running a company. Because it is, it feels like we're at a private conversation yet I know that, you know, so many people are going to be listening to this. But, you know, there's two things I think a lot about one of which is potential of people about taking the leap to do it in and of itself. And we touched on that a little bit earlier, really finding this notion of confidence and courage, which I really do believe has to be learned and earned. It just doesn't come innately to all of us. Just practicing jumping off the cliff, practicing taking a chance. But this other reality, particularly as a female founder, and I think it just comes up enough with other female founders. It's very lonely. And so I really appreciate the words of confidence, because most of us need it. We need the fuel from somebody else who's sat in those shoes, and has been successful, particularly if it's a female, to say, Okay, I see you, you're on the right track. I just personally, deeply appreciate that. Because you don't want to shout out to the world when you're failing, right? You want to put on a strong face, you want your team to have a strong leader. But it's really hard. Particularly when, you know, most of us have never done this before. And there's some sort of assumption that we've got a playbook and we do not. Looking at my whiteboard right now, I mean, holy cow, there's just, there's so much to do. So anyway, just just a real deep thanks. And you know, obviously for the conversation today, but for the acknowledgement for all of those, any founder, particularly female founders who are out there, like we see you, you're not alone, and there are very few of us. But I think learning how to find community, and leaning into what we've all learned is a really special thing. And that's particularly been some quiet fuel in my engine over the years. So-

Susan Sly 49:32
And as a mom, and the gift I will give to you, because everyone that comes on the show we all become friends, is that I never apologize to my children for, from working. Because we live in a world where, you know, somehow, you know, we have to apologize for work. I never apologize. I said, Mommy's going on a trip. Here's why I'm going on the trip. Here's who I'm going to meet. And even when the kids were little like, your daughter's age, I would bring them to business meetings. And my, four kids in there, my youngest now is 14. But I, my 18 year old, she's working in hospitality, is really funny. And she's like, it was a slow night the other night. So I interviewed the security guys. And I said, What did you ask them? She's like, I wanted self defense tips. I want to know why they're here, what their ambitions are, because she grew up in an environment that you're curious, you're not as a woman apologizing for your ambition. Elon Musk is not apologizing for his ambition whatsoever. And it's a very large ambition that he has, that I didn't apologize, Jennifer. I didn't like, it didn't mean I wasn't torn apart in pieces at times. You know, I, I wanted to be there every soccer game, every recital, every everything. But I didn't apologize because I didn't want my girls especially to ever think that I had to apologize for production.

Jennifer Ryan 51:04
I needed to hear that. And I didn't realize I did. So I really appreciate it. Because it is so real. And I do, and I think about why I work personally. But I also think what I'm bestowing on my daughter, what skills, values, meaningful through lines of how to approach life and the permission to choose your own adventure. I think about that a lot. She's two and a half, you know, we're grappling with these existential conversations at home. But what I'm trying to do is we know kids don't learn by us telling them things, they learn by watching us.

Susan Sly 51:39

Jennifer Ryan 51:39
And it's such a good reminder, because those little habits of apologizing for something that we shouldn't be sorry for quickly gets caught in their vernacular, it quickly becomes part of their psyche. And I just, I didn't realize how much I needed to hear that. And I really appreciate it. So for all you listening out there, if you needed to hear it too like me, it's just a really, really good reminder. And being unapologetic about creating and building and improving, you know, the lives and the systems around us like, contributing. So thanks, I just really appreciate, with four kids. My God, it's just incredible. So wow, what an inspiration.

Susan Sly 52:24
Thank you.

Jennifer Ryan 52:25
I'm building this into my own approach of working momhood. So-

Susan Sly 52:30
yeah, well, and the only way we are ever going to have more women founders is conversations just like this. And you know, the other thing I'll say to you, we always, I would get the kids together, we'd make family vision boards. I remember one was Bali, the four seasons, and I'm like, Okay, this is what I'm working on. And here's what it's going to, how it's going to go down. We're, I'm going to be there for dinner, we always sat down as a family for dinner, and then we're going to, I'm going to be there for homework, and then I'm going to tuck you in, but you're going to probably hear me because I'm going back on my office, and I'm calling from East Coast to West Coast, and I'm going to be doing these things. And they'd be like, how close are we to Bali? Or what can I do to help you? Or you know, can you take the dog for a walk because I don't want the dog barking while we're you know, while I'm doing this? And, and we celebrated because they contributed. And that's the you know, that's the thing I will say and you know, God, thank you, God, you know, all of them, like 3.9 GPA, 4.0 GPA, like all they, I never pushed them in school, because they saw me push myself and I didn't even have to push them. And so that would be my contribution. But Jennifer, you have got this, I am so beyond excited for you.

Jennifer Ryan 53:56
Thank you for the opportunity. Thank you for all you have done. It's just such a gift to have the conversation today. And I mean, listening to you and hearing the stories, so many stories that you've unearthed that I never would have ever heard or learned about. It's just, it's really been a pleasure. So I appreciate the vote of confidence, I'll keep you posted.

Susan Sly 54:15
Well, all of Jennifer's links are in the show notes. And so, and tag us on social if this has been helpful. And as Jennifer said, leaders ask for what they want. So our bat signal is like if you're a mom, if you're a grandma, you know, please tag us if this has been helpful. If you're a dad, a single dad, you know you we are all in this together. And Jennifer, thank you again so much for being here. And you know, I am so excited for your moonshot. I see it. I see it so clearly.

Jennifer Ryan 54:50
Thank you. Thank you.

Susan Sly 54:51
All right, everyone. Well with that this has been another episode of Raw and Real Entrepreneurship and I hope you go out there and just crush your dreams and have the courage to do so. And I will see you in the next episode.

Susan Sly 55:07
Hey, this is Susan and thanks so much for listening to this episode on Raw and Real Entrepreneurship. If this episode or any episode has been helpful to you, you've gotten at least one solid tip from myself or my guests,. I would love it if you would leave a five star review where ever you listen to podcast. After you leave your review, go ahead and email Let us know where you left the review. And if I read your review on air, you could get a $50 amazon gift card and we would so appreciate it because reviews do help boost the show and get this message all over the world. If you're interested in any of the resources we discussed on the show, go to That's where all the show notes live. And with that, go out there, rock your day, God bless and I will see you in the next episode.

Susan Sly 56:01
Are you currently an employee looking to start your own business? Maybe you've been thinking about it for a while and you're just not sure where to start? Well my course Employee to Entrepreneur combines my decades of experience as an entrepreneur with proven methods, techniques and skills to help you take that leap and start your own business. This course is self paced, Learn on Demand and comes with an incredible workbook and that will allow you to go through this content piece by piece by piece, absorb it, take action and then go on to the next module. So check out my course on Employee to Entrepreneur.

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Susan Sly is considered a thought leader in AI, award winning entrepreneur, keynote speaker, best-selling author, and tech investor. Susan has been featured on CNN, CNBC, Fox, Lifetime, ABC Family, and quoted in Forbes Online, Marketwatch, Yahoo Finance, and more. She is the mother of four and has been working in human potential for over two decades.

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