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Join Susan Sly in this illuminating episode of the Raw and Real Entrepreneurship Podcast as she explores the inspiring journey of Chelsey Roney, co-founder of Proxi ( Witness how Chelsey, a notable entrepreneur and mother, transitioned from a finance role at Boeing to B2B omnichannel marketing at Microsoft, and ultimately into the realm of tech entrepreneurship.

-Chelsey Roney

Topics covered in the interview

Entrepreneurship, motherhood, and business growth

Exit strategies

Valuation in 2023

Fundraising challenges for women-led startups

The beginning of Proxi

AI and its impact on society

Balancing work and family life

Chelsey Roney’s Bio

Chelsey Roney brings her business-building and strategy experience to Proxi, where she serves as COO and leads a team of 5, growing the business through sales and marketing. After graduating from Texas A&M, Chelsey joined Boeing where she worked in financial planning and analysis and Microsoft where she worked in a demand center that focused on B2B omnichannel marketing. She grew and sold two businesses: a SaaS business in the University space, and a local services business. Chelsey is also an active member of her community, dedicated parent, and passionate supporter of women and business.

Follow Chelsey Roney

Show Notes

Read Full Transcript

Susan Sly 00:00
Hey there, Susan here. Oh my gosh, I'm so excited about this show, I cannot even begin to tell you. This co founder and her fellow co founder started company out of the need during the pandemic as moms trying to help people navigate where they can take their kids trick or treating. And from there, they have grown a company that has a significant user base. They are just incredible humans. And on top of everything, the entrepreneurial journey this co founder is going to share is definitely going to warm your heart. And if you're looking for an episode of tenacity, of ingenuity, of risk taking, and just being able to understand that you don't have to sacrifice everything to go for your dreams, this is the episode for you. So the co founder of is here today, Chelsey Roney, and Chelsea has a background working for Boeing, also from Microsoft. And you are going to hear about the different business ventures that she endeavored in, including things she had no experience in. So it's such an exciting episode for me. I absolutely am excited for you to hear from Chelsey. And before we get into the show, I just once again want to thank you for being here. And if you haven't done so, please do subscribe to the show. And I would love to see a five star review from you. And follow me on social on Instagram @Susansly, on X @Susanslylive and on LinkedIn. And all of our show channels as well. The show is a labor of love. And for those of you don't know the origin story, back in the 90s, I was in media. And then during the pandemic, I just felt this need in my soul to connect with people and to also just hear and be inspired. And so we started to really take the show to a different level and put out a weekly show, meeting all of these incredible founders. And today, I've interviewed over 330 founders. And so this show, today's show is very special, because I love to highlight founders who are women. And I love to highlight founders who are moms. And so with that, let's go ahead and get into this episode with the founder of, Chelsey Roney.

Susan Sly 02:35
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 02:49
Well, what is up, Raw and Real entrepreneurs wherever you are in the world, I hope you are having an amazing day. And as you heard, this incredible, incredible founder, I have like 5 million questions for her. So this is going to be a 15 hour show. No, it's not. What's going to happen is we're going to have a show and then at some point, we're going to meet up for margaritas and all the things we didn't cover on the show. We're going to have girlfriend chat. Okay, Chelsey, I gotta ask this first question, Microsoft and Boeing and then you become an entrepreneur, like how did you go from employee to entrepreneur?

Chelsey Roney 03:24
Okay, so the story's a little more nuanced than that. And I'll give you how, I'll tell you how it happened. So senior year of college is when I Well, first of all, I've had like a knack for entrepreneurship my whole life. I think for a lot of us, it's in our blood. It's something we're, you know, oftentimes feel like we're born with, I started my first business when I was five or six and kind of had ongoing businesses after that. Various things from like, you know, pet sitting to like swim lessons, etc. But senior year of college is when I started my first business, it was a SaaS business in the university space. And we got started with one national account, my senior year of college, we were solving an issue that was, we were solving something that was a manual process, turning it into an automated one. And, you know, meanwhile, I graduate with my degree in finance, and I ended up working at Boeing in financial planning and analysis. Meanwhile, I'm still growing this company after my full time job. So I would work from like 7:30 to, you know, four or five at Boeing. And then I would come home and work almost a whole nother day. So probably like six to midnight ish, on this other company. And I did that for, you know, six, seven years. We had a team of, four of us going or five of us going after it. And we all did it after our full time jobs. Now the important thing to note here is that this SaaS company, you know, was, the tech was, it didn't require a lot of hand holding. And we made it so that it was very easy to use so that once you were on boarded, it just made intuitive sense. It wasn't like we were taking a lot of customer, you know, help calls all day or anything like that.

Susan Sly 05:15
I want to pause just a moment. Microsoft, are you listening? Intuitive SAS. That just makes a lot of sense. Hello, whoever is on the Teams like design that, no. And then Microsoft UI? No. and No offense, because I know you go on

Chelsey Roney 05:32
Oh my gosh, my huge Microsoft fan girl. Yeah.

Susan Sly 05:35
If more women would design UIs, we wouldn't live in this world we live in. Okay. Yes, please.

Chelsey Roney 05:42
100, I totally agree with you. It's all about into intuitive user shipping, can someone walk through the product on their own and use it on their own, and you know, different tech will meet people where they're at, there's some tech meant for developers, there's some tech meant for the average person. And I think whoever's designing that UI needs to be really cognizant of who they're designing for. And that's overlooked a lot of time. So that aside, I ended up working on this product for six, seven years, we ended up selling to private equity, that offer came out of nowhere, I just get an email in my inbox one day that was, you know, we're holding co, we're building, you know, we're taking all of these companies in the space. We're-

Susan Sly 06:29
Sorry, I have to ask you this this question, because I've received many such emails. And, you know, it was like in Nigeria, you know, is it a Nigerian prince email? Or is it actual, like, how did you know that this was like, not a spammy Email?

Chelsey Roney 06:42
That's a great question. Well, it looks legitimate, first of all, and so then when I went to that website, in a signature, it really was a holding company, or upright, you know, a company that really was consolidating these firms, and they had all these press releases, and like, you could tell like, this was actually the real deal. Furthermore, they were ready to give an LOI without even, you know, it was like they were ready to move forward. So that was a pretty unique situation. In hindsight, just never having gone through that before. Usually, it takes many months of finding the right acquirer, or, you know, working through all of that, and we didn't have to go through any of that, it just, we were lucky that it just worked out. So. But meanwhile, I had gotten my MBA at University of Washington. And then I moved over to Microsoft, and I first worked in recruiting there, and then I ended up in b2b marketing. Yeah, a bit more to it, but more or less b2b marketing. And while I was at Microsoft, I sold the first business and I ended up using some of those funds to purchase a local landscape installation firm. And the goal, at that point-

Susan Sly 07:54
hold on, hold on hold.

Chelsey Roney 07:55
I know, I know.

Susan Sly 07:57
Girl, like we just, you know, you're like one of these powerhouse women. It's like you just kind of throw this and so I'm doing a finance degree, but I start the SAS company part time and then just random e-mail, we exit this, but I'm working at Microsoft, I get my masters at U-Dub, and then I buy a landscaping firm. Landscaping firm. Okay, how did that happen?

Chelsey Roney 08:22
Yes. Okay, so the idea at this point, I've started so many companies in my life, you know, a lot of them much smaller. But I had realized that my passion is around building business. And I'm more agnostic around the, you know, what the business is, I just love figuring out what customers, makes customers buy. I love figuring out how to sell it, love figuring out every piece of it. And so I had been scoping out local businesses for a long time. And it was more about was the business a right fit financially? Was it someone I could hire a manager role into so I don't have to be in the day to day, you know, are the, is theire low hanging fruit? For instance, this business I chose didn't even have a website, you know, like, how can I find something where I can really expand it from what it is currently. And so I made the choice to buy this business. And you're right, there were some, you know, you're alluding to, there may have been some bumps and there absolutely were. I mean, you know, first of all, I didn't know anything about landscaping. So that was a big problem. But I learned a lot. And now I can tell you anything you need to know about landscaping. And, you know, we managed crew, I had three crews, they didn't, I didn't speak their language. So that was, that was quite a problem. And then of course, there was a gender disparity, with me being a manager, the female and then most of all of my crew members being men, which was fine. They were, for the most part, that was just fine, but it did cause some differences in terms of working relationships. And then for me personally just a learning experience. I don't know how to, I think probably people can relate like I just had never, I had never done a physical job like I hadn't physically labored before. And so I never, I'd still have never physically labored. But managing people who were doing that type of work presents different problems across the board, both literal physical problems, like if they get hurt, or if they're tired, or if it's hot or too cold, or things like this, to just like, what it looks like to, you know, even how overtime works when you're doing physical jobs. So it was really a learning experience. And then, with that business, cashflow also looks different. Because with a SaaS business, the margins are high, there's low cost, you can make distributions to yourself, you know, yeah, it's a different ballgame. And so whenever we walk, I walked into landscape installation, there's a lot of working capital that you need to pay your employees, to run the actual crews, maintaining all the equipment, the lot that you park, everything on in it, reserving materials for jobs out into the future, it's really a bear. And so, of course, having been a finance major knew that cash flow was important, but it really hits home when all of those factors come into play when your're in charge.

Susan Sly 11:33
Would you have, going back and giving advice to your younger self, Would you have still purchased that business?

Chelsey Roney 11:39
I think so. You know, I'm sure you can relate, and listeners too like, part of entrepreneurship and being successful in entrepreneurship is like a night naivety. Naivety, like going into things. If you knew what, you know now in every entrepreneurial role, would you ever go back and do it? Like probably not right? No way. And so I think I would never tell myself anything different, or I would let it happen.

Susan Sly 12:10
Yeah, because things build, right, Chelsea, like things build on, you know, in the 90s, I bought a health club. And the, you know, the lessons learned from that are lessons learned from you know, choosing the right business partner and things that capitalize on that. And as entrepreneurs, we always say, of course, I would go back, it's my real life, MBA and PhD and you know, everything, but at the time, it's a little sucky.

Chelsey Roney 12:40
Yeah. Oh, god, yes. I mean, well, one, I'll give you a raw and real example from this business. When I purchased the business, I consider myself fairly financially savvy, reviewed the financial statements, reviewed everything I thought I needed to, had an accountant, had an outside adviser even come in and review all of these financial statements. And after the purchase went through, and there was nothing I could do about it, I realized that the business had actually manipulated financial statements. And so yeah, talk about like wanting to go back and like feeling that deep regret and feeling like, oh, man, I really messed this up. Like, not only are they financially negative, but it's like 20 or 30k a month, like, and turning that ship around with your personal money on top of the personal money that you already invested in it, feels well, you can imagine how, anyone can imagine how that feels. So you know, there are lots of lessons learned there. And lots of things I would tell myself about that, in particular, but I don't think I would go back and erase the purchase.

Susan Sly 13:50
And even looking at your, your career highlights or your you know, body of work, right. And going from SAS and going from landscaping. And like you said so eloquently, it's this, this excitement and building and growing a business and you, there are certain things you can take regardless of the business. And you and I are sisters in that regard, from one business to another, you know, a p&l is a p&l in, you know, certain things about HR, management, insurances, like all sorts of things, they just transfer and then the more businesses you do, the more experience you get. I want to, I want to ask you, before we talk about Proxi about valuation, because this is you know, Raw and Real Entrepreneurship. 2023, depending on when someone's listening to this, has been the toughest year in raising money. And a lot of people that you know and I know are starting tech companies and we're not seeing the valuations. I call 2021 the year of perpetual Christmas. We're not seeing the valuations that we were. And so if, in starting, if someone's starting a business right now, and let's say a tech business, what advice would you give to them in terms of choosing that early valuation, especially if they are going out there to raise money? Because I think you're uniquely qualified in so many ways to give that wisdom.

Chelsey Roney 15:27
Oh, Susan, I don't. That's a hard question. Obviously, right now, I think you're absolutely right, that the year of 2021, was incredibly unique. I will say that, in 2021, was the first time I raised venture capital, and we raised around 2 million. Yeah, I mean, like, is that public? Yeah, to around $2 million. Around a $10 million valuation. I will say that, when we're looking at raising capital today, that valuation is, even though we've been building for two years since, is probably the maximum valuation that we would see on our company even today. So I think you're right that, obviously that there was inflation in the past couple of years, and that those valuations are drastically coming down. I think in terms of raising money, if I were to start a company today, and attempt to go for it, again, this is just my thought. I would try to bootstrap it until the market gets a little bit more returns a little bit to where it has been in the past. And the reason why I say it is because I think valuations are really low right now. And maybe some of them are appropriate, I'm sure some were much, much too high in the past. But when you're a founder, and you're starting, obviously you want a higher valuation, so that you can keep a larger portion of your company. And so however long people can hold off in fundraising might be a good idea, at the very, at this very moment in my mind. Now there, you know, you might have to raise money to either build a team to build your product or to continue growing like us. And in that case, you know, I think finding a VC that sees the real potential in your solution area and finding a lead investor that sees the real potential and believes in it as much as you do will be key in getting the best valuation that you can. What do you think about this? It's a really tricky situation right now.

Susan Sly 17:55
It is and it's, I you know, if you look at this year, that it's we're seeing 409 A valuations at, 90% of companies are either have a 409 A that's less than last year or the same, then, you know, a friend of mine is an LP at a VC firm, they were going to disperse 90 million this year, they've dispersed 0 million, and zero pennies and 00. And so then we're seeing, I call it the mash up, where they, VCs that invested in companies in 2021, and conflated evaluations, and we saw like 33x, and so forth, that they are now, those companies are doing down rounds. And those VCs are looking to pair them up with other companies so that that other startup can boost that valuation. And we've never seen a climate like this right now. And I love what you said Chelsey about bootstrapping it, if possible, and also getting your head on straight. Like if you're going out to raise money in a new company right now, then, you know, in 2021, you could say, oh, my new idea's worth 20 million, and it's pre revenue. And you know, I'm gonna raise 2 million, and I'm only giving away 10% of the company. We're not seeing that now. And so it's, and I don't think we are going to see that, again. Not likely that money is going to be this cheap in the next few years anyway. So when you, and then the other aspect, too, is as a woman less than two and a half percent of pitches by women to VCs get funded. Yet women-led companies are 62% more profitable than male-led companies? Like what the heck?

Chelsey Roney 19:33
No, we feel that, we definitely feel that. I think we have, Well, of course, we're biased, but we have this idea that we really believe we'll change the world in the way that we're we want to execute will change the world. And when we talk about that you can tell that the questions that we're getting asked are a little more specific and a little more like you need to back it up more than perhaps a male counterpart. What I also see is if a male friend, or you know, like someone who is our ally in biz, you know, like a different company but like with a male CEO, if they pitch my company to someone else, you can see the difference in how people react to when I pitch my company. And maybe that's me needing to work on my pitch, I'll take that criticism, but like, I don't believe that's true, I think to your, to your point of what you know, women having a harder time raising, I think there is something to it, but it's really hard to pinpoint what it is.

Susan Sly 20:37
Yeah, and I love that we're seeing more women lead funds and companies. In one of the companies I invested in, Lori Harder's company, Lori was very clear, Lori was like, Listen, I'm only having female investors, you have to have either a podcast or X number of social media following in addition to being safe qualified. And, you know, I love the Lori's been a longtime friend of mine, that she was bold and said, This is what I'm doing. And I think we're seeing this trend of, yeah, women lead, women funded and you know, just get out of our way. We do, we 100% to you.

Chelsey Roney 21:15
And the more of us that can invest in other women's companies and pay it forward a little bit, even if it's one investment a year or two investments a year, if you are able to be an angel, or take some sort of leadership and that way, it, it makes all the difference. And I just read a LinkedIn post about how it's really helpful when women, and you know investors in general, but I'm gonna go ahead and say women, in this case, make commitments toward rounds for other women. And before a lead comes into play. Does that make sense? So like, even if a company is searching for a lead, if you're an angel out there, and you can make a commitment toward a company just to get that momentum building on their round, make it. If you believe in that company, help them move forward.

Susan Sly 22:03
Yeah, that's huge. And on the show, as you know, sometimes I'll do like unsolicited, like, for companies I've invested in. I had Jen Pelka on the show, Une Femme wines, and I invested because I love wine. That's okay, that's rRaw and Real Entrepreneurship. Jen was having wine while doing the show.

Chelsey Roney 22:24
You have to invest in what you believe in, that's for sure.

Susan Sly 22:27
Exactly. And to your point, I love that, you know, if you can, you're ISQ qualified, and you can afford to do that, and we need to see this. This is the rally cry for women and especially women in technology. So let me ask you this. Landscaping, okay. I, I'm not, it's not a judgment call. Because I could see myself doing that. I watch a lot of HGTV, like, decompress.

Chelsey Roney 22:59
It was like HGTV, I will admit, but I got to go in people's backyards. I got to be like, we should do you know, X, Y, and Z. And it was very fun. Yeah.

Susan Sly 23:08
Yeah. It's a true confession, like the Food Network and HGTV is kind of like my go to. So yeah, just like, okay, so, so. So Proxi, where did the idea for this come from? Because I love origin stories, like, you know, the true origin story, right? Where did you get this idea?

Chelsey Roney 23:32
So I have an amazing co founder, and it was her idea. And Melinda, her name is Melinda. I'll mention her name several times. She and I have been friends for over a decade, we both went to undergrad together at Texas A&M. And we both ended up in Seattle. And so when she ended up here with me, we, of course, continued our friendship. And a lot of our friendship was based on Nerdy business doc. So we would always say, Did you hear what happened to skim? Or did you hear what happened to like, you know, whatever other women founder and it was, it's been a lot of fun. But I, how it started, she was in a South Seattle neighborhood Facebook page. And it was the October right after COVID had started. And everyone here can unfortunately remember that we were all nervous about what would happen around the holiday timeframe and how not to spread germs. And so there's this movement that Halloween toward distance candy delivery. So putting candy on your front doorstep, sending it down a little chute, just staying away from each other, but still delivering candy. Well, in this Facebook group, a parent had made a post that said if your home is going to offer distance candy delivery, go ahead and write your address in the comments and then people will know where to go if they're nervous about this. Now, pausing the story, my co founder had actually produced maps for one of the US intelligence agencies before moving out to Seattle. And she knew based on her research that people synthesize place based information, visually, not in list format. And so when she saw this list of addresses, she was like this is unusable. What is someone going to do? Type in the first address then the second address. But what if that second address is farther away than a foot, You know, it just doesn't make any sense, right. And so what she did was created a map and strung together several tools on the market to create, like a visualization of all the homes in this comment thread, and then made it so that people could add their homes to the list. And so what happened, or what evolved was this map of Seattle where people could add their homes for distance candy delivery, and other people could easily access it and reference it. Within two weeks that had 500,000 views, and she was on Good Morning America with this mom saves Halloween story, which is amazing. But given our nerdy business friendship, she of course called me and we had been talking this whole time about why is this taking off? What is the catalyst behind why this is even successful? There must be something going on here. And what we found was that there were no crowdsource mobile mapping technologies in the marketplace. I think people out there will be like, Well, wait, Snapchat, wait, Facebook had had these like map functionalities within their platform that you can add to. But there's, there was no technology that was platform agnostic, where you could share a map across text, email, social, wherever you wanted to share it, that anyone could add map points to. And so we created this technology, and we put it out into the world, and more and more people began to use it. So people were using it for like Hurricane marking where like aid was in a hurricane situation, or marking, where holiday lights were going to be displayed or like Valentine's Day activities. So from October to around January, February, we had this NVP out in the world. And it was getting more and more traction. And people were coming to the site and requesting more and more features. And that's when we started to realize there's a significant gap in, there's not just a crowdsourcing gap here, there's a gap in custom mapping technology. And what we found was that people could either use Google mind maps, which is a fairly easy to use solution. However, there's a lot of red tape around what you can and can't do with that product. Or if you're a business, you can hire a developer to create a custom map for you. But there are all these people who sit in the in between who needs something more feature rich than a Google mind map, and who needs something that they're not going to dev out or pay someone to dev out. And so we began to incorporate more and more features into Proci like brand ability, for instance, like it's a white labeled mapping tool that people can embed in their website or whatever. At this point, we get into TechStars. And Seattle, which was a fantastic experience, I sold the landscaping firm, Melinda actually quit her Ph. D. program at University of Washington, dropped out of it to work on this, to work on Proxi, because we believed in it so much. We ended up raising a couple of million dollars at that point. And we built out a what we like to call the Canva of maps. So anyone could go in, create a beautiful map, publish it, share it all within minutes. Now, where we are today is that we've incorporated many features that are friendly to businesses. So not only that branding, we talked about, but also analytics on where people are clicking, what types of places they're clicking on, where they're converting that they're clicking on buttons, the whole thing to lead generation tools within these maps, to passport challenges that are digital instead of like a stamped passport booklet, among many other things, but we have turned on subscriptions and people can pay for some of those more advanced features at this point. And it works especially well for like media companies recommending locals, local things to do, or Chambers of Commerce or economic development or ads or travel agencies or, or things like that. Whoever's trying to activate people into their communities, but individuals can also use it as well. And that's where we, that's where we sit today. We have over 70,000 maps on the platform, which is really exciting. And we're continuing to grow.

Susan Sly 29:48
Chelsey, I love that origin story because as a you know, as a mom, like you're, there's a, there's a problem and it's what I find fascinating about this, and I've only had a couple of founders on the show, like you and Melinda, that have this initial kind of idea, you test you, that you're testing something, you're putting it out there. And then suddenly you have all of this interest of the users, because oftentimes what happens in technology, as you know, someone has a great idea and then they're trying to get those early users. But for for you, and Melinda it was so different, because you knew there was this need, and you were putting it out there into the marketplace, which definitely makes it very attractive from an investor standpoint. There's no question. And I think the, the, when I'm looking at this beginning of Proxi too, and I'm thinking, you know, my mind is going like all these different use cases. And with Melinda's background, I'm sure she has many ideas for different use cases for government and all sorts of things that could possibly happen. Thinking about all of your experience, and where you sit right now, if you could look, I guess, five years in the future, where do you think Proxi can grow? Because I know this is a question VCs ask you.

Chelsey Roney 31:18
This is something we talk about a lot and something we're actually really passionate about. So today, we are the Canva of maps, we are an easy to use mapping technology, anyone can come map and in publish these these maps. Where we're moving to in the future is a platform like an app where consumers can come and figure out where to go and what to do in a more personalized way than they're able to today. Using a lot of the data that has already been put into Proxi. So let's think about your experience right now when you use Yelp, Google Maps, or you know, just the web, the web, to figure out where to go and what to do. What you do today is you type in restaurants near me, let's just take this example. And Susan, if you and I are typing in restaurants near me we don't actually, we need much more than that. And we we need something, results that are much more personalized than what we're getting today. Today, you're returned with ad based results. So the top of the line is all ad, you know, filtered by who's paying to be seen. And then, you know, you can filter on different aspects past that. But let's talk about what we need. Susan, you might need a restaurant to have a really nice cocktail at with your friends after work. But right now, where I am in life, I need a restaurant where my children can be really loud, they're three and five. And, you know, things are wild at restaurants. So when we search restaurants near me, we don't mean the same thing when we put in that same inquiry right now. But when we're moving into the future, and we're thinking about technologies of the future, these technologies will know us based on prior search history, based on other things that we can input into the technology like questions that can ask you. And it will return more personalized results. So we will receive restaurant recommendations that are more meaningful to us and that we are more likely to convert on which is key for marketers, right? And, and you know, perhaps there, not only will there be personalized search results taking place, but in Proxi, you will also be able to layer in suggestions from trusted resources as well or your friends. So you might take Chelsey's map of Scottsdale, you might take, you know, Susan's map of Scottsdale. And you might take the local newspaper's map in Proxi. And you might layer them all together to get an experience that is unique to you. So I might want to first layer in coffee shops, and then playgrounds. And then like something else my kids might want to do all together so that I can make a plan on what to do today. And then route that plan and even book whatever I need to all from one place. So really the vision is that you're going to this app, you're getting these personalized recommendations that you actually want. And then you can also move forward with those recommendations, whether it's booking or directions or however you need to keep going but it should be more seamless, personalized experience in terms of wayfinding. Does that make sense?

Susan Sly 34:48
Absolutely. And what comes to me Chelsey is we were talking you know, Food Network, HGTV. So like Guy theory, diners, drive ins and dives. I could see my husband who's like a big foody like whatever city we're in, like, oh, I want to add anywhere that guy has gone to Triple D, right? And be able to create that, we were, funny story, so to your point, and there is a need. So my husband and I grew up in a really small town in Canada. And when I went into TripAdvisor, I'm like, every time we go home, this is Raw and Real Entrepreneurship. Every time we go home, we're like, yes, we want to see our family. But there's nothing to do. All right. And so I was like, maybe there's some new restaurants or something, and I go into TripAdvisor, and when the top 10 restaurants that it serves me up is literally McDonald's. Now, anyone who knows me well knows, like, I eat only organic. And I, you know, like, I'm super health conscious. And I'm just, it's a personal choice. I'm not going to go to McDonald's. So but then I found out when we were there, that there was a new place that opened and they were doing like these delicious quinoa bowls and things like that. And, you know, it's stuff like that. And to your point, like, I wouldn't have known if I didn't ask my friend who, you know, has a cottage in a town like, where do I go? And she's like, Okay, you need to go here, Susan, because I know how you eat.

Chelsey Roney 36:20
Okay, exactly. This is exactly the point. So perhaps she would put her recommendations online or on Proxi, right? In this special part about Proxi, as eventually surfacing information to other people, is the description. So she would write whatever she wants to about those quinoa bowls or like healthy eating, or living or whatever makes sense to her. And then what we would do within Proxi is use AI NML to understand all of the descriptions in aggregate, and then recommend them to use this. And so we would be able to take this description about this business, and maybe someone else's description about the same business, triangulate it to you and recommend it. And that's what's different about the vision for Proxi in the future versus Google or Yelp is that people aren't able to, I guess, you know, Google and Yelp aren't using comments. They're not using, like descript, like rich information about place to surface recommendations. And that's what we're aiming to do.

Susan Sly 37:26
Yeah, and I see so many, you know, positive implications using to your point like generative AI, using even voice you know, as well to be able to shape that custom experience. Now, I want to ask you the shifting gears, because you and I both work in technology, we're both moms, your children are much younger than mine. What excites you about AI and what terrifies you about AI?

Chelsey Roney 38:00
Well, I think what excites me, and probably because I talk about this a lot, is the personalized experience that we're going to be able to receive from AI. I think whether that's like AI as a personal assistant, and you know, making your life so much more streamlined to trip planning to whatever it is, or personal recommendations like we plan on helping with, I think that's what excites me most is this. It is a truly like, individualized interaction with the internet almost, and in how we interact with the world, in a much smarter way to interact with the world. I think what scares me most, obviously, is, I mean, you know, all the science fiction things that we hear about AI like being able to eventually talk to each other and build on one another and build towards something that none of us really want to see. And how do we regulate AI and ensure that it doesn't overstep any boundaries, but I think we're a long way away from that. And there's a lot of reason to be more positive than negative about AI. But

Susan Sly 39:17
And to your point, it's interesting as a parent, because I was just doing a big talk on AI, and the things that we used to say to our kids in terms of going to university even or what they would study and my talk was centered around which jobs are most likely to be displaced. And here's the interesting thing. One of the top areas that is not likely to be displaced by AI is landscaping. Not even kidding. And to your other point, there was a just, I just did a talk on this too. I was illustrating this when I was in Barcelona, speaking for HPE, but in Hong Kong, there were three Chinese drones and they gave them one instruction, which was find a key and they hid a key in a park. The drones spoke to each other, collaborated, they problem solved, they got organized. And they figured out their technique and how they were going to find this key, and how they were going to procure the key. And they did it without any instruction other than find the key. And so we're there. And, and that's the thing, I think, you know, one of the things that, that I talked about a lot is, is women in AI and women leading this, and I love that you and Melinda, have a company and you know, someone might say it's a mapping company. Someone might say it's a technology company, in my mind, it's a technology company that is going to be incorporating personalized AI and I love that, that focus for you, and to be a woman and to be a leader and to stand in your power, especially when you know that for us as women in technology, sometimes there are more challenges, because we need more women leading companies that are AI enabled in these, in this coming era, there's there's no question especially as mothers and leaders, right?

Chelsey Roney 41:16
I think we have a unique perspective from a woman, you know, just from a woman's point of view. And I hate to, I don't mean to overgeneralize or anything but I, a word that comes to mind when I think about women in leadership is reasonable. And I think there's some lack of reasonability within leadership at companies, especially that have AI. And it's my hope that, just like your hope, that we can provide reasonable expectations, leadership, guidance, rules around this ever evolving technology. And I think we have to take leadership and encourage one another and boost one another up so that we have equal representation in this field.

Susan Sly 42:17
There's no question. And I love that you and Melinda are moms because when I think about AI, it's something we're giving birth to. And who gives birth? Moms do. And also thinking about, as you said so beautifully, like we have to safeguard this because at some point, I always say, Chelsey, that AI is in the toddler stage. And you know, when my son was smaller, he ate dirt. My girls didn't need dirt, but my son ate dirt, I don't know. I told, I turned around, he's like eating dirt out of the plant. I'm like, Dude, what are you doing? So that's the stage we're in. Like with AI, it's very cute, but it's still having temper tantrums, that doesn't always pave the way we want. Like you said, the restaurant. I like to, I need to go to a restaurant that you know, if we're loud, it's going to be totally okay. And that's where AI is now. And that's why I think that women are so well positioned to be governing. And like you said, reasonable, governing this AI expansion. And Sharon Goldman, who's a tech reporter at VentureBeat, we're like, all over LinkedIn talking about how Open AI has no women on their board, depending on when someone's listening to this. But after Sam Altman is out, he's in. And they have three dudes on their board. And it's like.

Susan Sly 43:40
No comment.

Susan Sly 43:41
I am commenting. I commented all over the place.

Chelsey Roney 43:43
I have been so passionately following this particular representation issue. And it's huge. Open AI is transforming the way everyone does work and lives life and they're at the forefront and they really need to have equal representation.

Susan Sly 44:06
Yes. Because if we are going to democratize AI, then shouldn't the, whoever's on the board be reflective of humanity? Hello. I think last time I looked at, we were approximately 50 or 51% of the population.

Chelsey Roney 44:22
It's a big deal. It's a dig deal to, I don't know what's going on there. But something needs to get figured out.

Susan Sly 44:31
Oh, yes. Absolutely. And you heard it from Chelsey and Susan, who have decided Open AI, guys, listen up. The Silicon Valley bromance thing. It's so you know, so gone. It's time to smarten up. Chelsey, I have a final question for you. This is, this is like a hard space question because you have a three year old and a five year old and you're building a company and you, building a company is like having another child. It, you know, there's a lot of decisions you make as a co founder every single day, many hats you wear. And because of your background in finance, it's not like you can't, you know, be looking at those p&l, and on top of it everything, like you said earlier cashflow, and plus you're. So it's a lot going on. How do you handle life when, you know, with kids and the startup and everything, like how do you, what are some of your strategies?

Chelsey Roney 45:39
It's hard. I think every woman out there can relate. Some days are really difficult. And there are other days when everything feels like it's fine. But I think my top, my strategy that works the best for me, and then I feel most comfortable recommend, you know, talking about is prioritization in your day. For me, what I do is I identify top three priorities of the day. It could be as small as sending a really important email, it might be throwing up a new page on the website, at our stage, I still do that. It may be getting my daughter to her competitive dance class, you know that some days that just has to come first. But I, I identify those top three priorities for the day. And I do start on them first, I get them done, and nothing comes before them. Not text messages, not phone calls, not emails, not pings, not Slack, nothing can come before that for me. And it annoy- I can see where you know, it does rub people the wrong way who you're trying to talk to me and trying to get in touch. But this is what works for me. Because these top three priorities are things that I've identified that will move things forward, and not, you know, just working in the business like, you know, paper pushing, basically. And so once those three things are done, then the other things can start to come into play, the emails, the meeting, the phone call, whatever else is more transactional, I suppose can come into play. But as long as those top three priorities make it through, then I'll relax. I think a lot of people can relate to this too. Before kids, I could work 12, you know, 20 hours in a day. I could work a long time and not feel fazed and I would be happy and giddy. But I can't do that anymore. And I have to be gentle with myself in terms of letting the rest go after those top three things make it through. And of course, I tried to do as much as I can. But past that, I let the guilt go if those three things are done.

Susan Sly 47:59
I think that is great advice. Because the reality is that if you can accomplish the things that aren't going to knock down the dominoes, a lot of people focus on them minutia. There was a, one ofthe first business biographies I ever read was from a Canadian entrepreneur whose name was Casey Irving. And he was a billionaire many times over. And he had the same philosophy. He passed a very, very long time ago, but he said, I write down three things and I do not do anything. And this was before you know, Slack and text and smartphones, everything, but I don't do anything other than those three things. And there's, there's an amazing compound effect to that. Because that's 60 things a month, if it's Monday through Friday, 720 things a year, and you're gonna make those strides because one of the things, and I know for myself, since it's Raw and Real Entrepreneurship, I spent five years helping to build this AI company. And there have been many times in the morning when I get up and I pray and I meditate. I'm like, God, please help me get the time I've lost with some of my kids back because they're, I was building the company, the face of the company. And, and you know, and that, it is to your point, it's hard. And there's, for people who haven't started businesses, they can look at it. Like, you know, when Elon Musk got his first McLaren when he sold the first company and you know, you can look at all of the like trappings and Jeff Bezos on his yacht and everything. But when you ask the bigger questions, like, you know, how are they actually living their lives? And you know, why is it that they're on their fourth partner or fifth partner and they have all these big divorces with these massive settlements. And and I think there's something to be said about knowing how to prioritize like you said, knowing how to delegate. And if one of those three things is getting your daughter to the dance competition, and my daughter used to competitive dance, plus it's the hair, done makeup, like when they hit a certain age because they gotta like and the dance leader, if the bun isn't done right, like, oh, dear Lord, right?

Chelsey Roney 50:20
Yeah, so true all of it. Man, it's a lot.

Susan Sly 50:24
And, and there's something to be said at that because you you building a business for a reason to contribute tremendous value out there. But you don't want the collateral damage of your family because that is a price that no one should be willing to pay. So I love that you said that. And your transparency. And it, I like, I know. Like that's why I said at the beginning of show, we could do a 15 hour show, but you know what, we need to get Melinda, we need to get Jen Pelka with Une Femme, and we'll get Lori to bring the Gloci and that way our skin look right after we have wine. Yes. And, and do a female founder summit because this is, I think this is so important that we have these conversations. So Chelsea, thank you so much for being on the show.

Chelsey Roney 51:10
Thank you, Susan, it was a pleasure to talk to you.

Susan Sly 51:13
Well, and everyone, check out the show notes. Go check out and go make your map.

Chelsey Roney 51:21

Susan Sly 51:22
.co Sorry, don't go to .io because you will not get there. Now Chelsey has got to go on GoDaddy and buy that. Yes, there we go. I'm so focused on the conversation I did not even look. Okay, Llet me do a redo of that. But anyway, thank you again, Chelsey, so much for being here. And next time I'd love for you to come with Melinda. We can have like such an amazing chat. And definitely, I would love to have you back. And to everyone listening in the world and especially to the women and to the moms and to the dads please we would love a five star review in the show, share the show and tag us on social. So with that God bless go rock your day and I will see you in the next episode.

Susan Sly 52:12
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 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 53:06
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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Author Susan Sly

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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