Raising Capital Online with Rebecca Kacaba

Josh Wilson (00:00:00) - Two. Good day everybody. This is Josh. Welcome to the Deal Scout. On today's show, we're gonna have a conversation with, uh, a lady out in Toronto who is doing some incredible things for the deal making world. Rebecca, welcome to the show.

Rebecca Kacaba (00:00:15) - Thanks for having me, Josh. Great to be here. Yeah,

Josh Wilson (00:00:17) - Awesome, awesome, awesome. So you're in Toronto and you are an absolute deal maker and your team helps deal makers, don't you? Tell us a little bit about who is Rebecca and what do you do?

Rebecca Kacaba (00:00:28) - Yeah, thanks. So Josh, my background was a capital markets attorney for over a decade, but please don't hold that against me. Listeners, don't hold that against me. I'm sure lots of you are attorneys as well. And I closed lots of deals, sometimes referred to as a deal junkie. Saw a need in the market for my clients to have technology to help them close their capital raises because it was largely paper based and cumbersome. And I saw the Jobs Act come out and the idea of these equity crowdfunding portals. And I said, you know, I don't think necessarily that's gonna be the right way the market goes, but I wanna create more of a Shopify solution so that people can set up an online store and raise capital and do their capital raising in their deal, making digitally. And so that's what we've built. Fast forward five years, we're edging close to 2 billion capital transacted through the system from investors all over the world globally.

Josh Wilson (00:01:26) - Wow. All right. So this is gonna be great because I've seen a lot of people have ideas about, you know, let, let's, let's set up this thing that could raise money or that could do deals from real estate to vc Angel. But you started on the legal side because I think a lot of people have the idea to start it entrepreneurs, and then they catch up with the legal side and they realize I can't even build this shit. Right? Like, so they have to go backwards and fix it. You started with legal, which I think puts you ahead of the game. Brilliant. Um, kind of like, talk to us about what, what, what was the, the, the change in the industry? You said the job acts really changed the industry for you guys, which made it, uh, available to do these kind of things. And then other things that you saw down the path, like kind of talk to us about the turning point where money could be raised and deployed digitally.

Rebecca Kacaba (00:02:15) - Yeah, for sure. I think, Josh, you're right, like I had been my entire career doing deals. So it's not just having legal background, but it's knowing every twist and turn a deal could take. And I spent five years sitting with developers and really baking that into the software. So the big turning point that I saw with the jobs act was previously, you know, you've got, you guys deal with a lot of real estate funds or I had, you know, people doing SPACs or going public, right? Any of those deals, you're trying to corral a large number of investors into one term sheet, one transaction. Then the jobs act comes out and it says, okay, we're, we know that companies are taking longer to ipo. We wanna let more Americans invest before that i p o hits because, you know, that's now happening longer and longer.

Rebecca Kacaba (00:03:06) - We wanna let every American in at an earlier stage. And so, but we're gonna have different criteria they need to meet. So now it's not just making sure that people are accredited investors, maybe they meet different net worth requirements and they could put in different amounts of money. All that stuff is really complex for their average, the average entrepreneur or person who's trying to close a funding round. So I said, we're just gonna bake all that into the software so that you can put up a link on a site, you can drive people to that site, and then the software is gonna figure out which securities law exemption they meet to run the right background checks, get the right documents uploaded. We're gonna make it as easy to sell shares online as it's to sell shoes online.

Josh Wilson (00:03:48) - Ooh, I like that. And, and as you, as you guys are coming up with this, this process, right? There's been a, there's been legal changes, right, with the jobs acts and with stuff when it comes to accredited investor, non-accredited crowdfunding. Like how did you navigate all of those things? And you're doing it internationally. So you got Canada rules. Yep. You got us rules, you got international. How do, how do you stay on top of all of the, the different laws and regulations for it?

Rebecca Kacaba (00:04:18) - Well, we do so many deals. Like we're launching 30, 40 deals a month that we're constantly working with all different kinds of companies and their attorneys who are helping them out as well. And we have a deal set up team that really is deep in the weeds. Nobody's launched more deals. I think we've done, like over our history, probably close to 800 deals, right? There's, there's a no law firm that's done that many deals. Our deal setup team are pro is that understanding and coding up the requirements that each of our clients have.

Josh Wilson (00:04:48) - Yeah. So let's, let's talk about what kind of deals did you guys first start doing? Like what was the first deal that came on the platform?

Rebecca Kacaba (00:04:57) - That was some of my clients that used it while I was still practicing. So they were doing, there was a lot of cannabis raising at the time. Yeah. So that, that was cannabis deals. Yeah.

Josh Wilson (00:05:07) - Well and that, and that has its own legalities with, with different industries, right? So like, what could be raised, where could we invest our money? Where could we deploy money? So as you're, as you're going through this, those were the first kind of deals. Like what was the, what was the first and best deal that you guys, you know, like the, the first big deal that you guys were like, oh my gosh, here we go, this is it, this is the turning point for us.

Rebecca Kacaba (00:05:29) - Oh, I mean, without a doubt that was the Green Bay Packers, right? Like there's no bigger brand than an NFL team. Yeah. And the amount of prep we did for that deal to make sure, like the fans were rabid, they were ready to come by their shares, and you know, the cheese heads, they, they don't mess around. Like they wanna be owners of that NFL team. So the day that we launched that deal and we had a million screens up, just like watching the volume hit and the day, the minute that deal opened, there was like 40,000 fans on site. It was crazy.

Josh Wilson (00:06:03) - Holy moly. So exciting. So you guys have seen so many deals and you've seen deals gone, you know, deals that go good, right? And just as planned, right? And then you've seen some deals gone wild where it's just like, we have no clue what even happened there. Like what, what would you say when it comes to raising capital and you know, like these, these groups that are doing it, what would you say are some key points to prevent deals from going wild to keeping deals on track?

Rebecca Kacaba (00:06:31) - Yeah, so I think in the retail capital raising space, like raising money digitally by, through digital marketing efforts over the last six to 10 months has been a really crazy time, right? Like a lot of people were watching this market and saying, this is never gonna work. It's just like NFTs, it's just like crypto. And we've seen deals continue to perform amazingly well. We, we've got a lithium deal closing right now, raising millions of dollars. And, and what has proven out over the that time period is that if you've got a good deal, people want it. And that doesn't change in a down market. And retail investors, you know, you get people talking about how much the con average American consumer has to spend like buying shares online. Consumers want in on that. They wanna make these investments that's not going away. And this, this space isn't going back to paper and pen. So I think a lot of what's proven out over the last six months has been that there are rabid fans just like the Green Bay Packers who wanna make investments and they wanna invest in companies that they believe in. The equity crowdfunding has shown those fans of the company are really strong supporters. We have clients who have gotten some of their biggest contracts from the people who made those couple thousand dollars investments.

Josh Wilson (00:07:55) - Now explain that because I've, I've seen, you know, we've interviewed Republic and, and Crowd and a few other crowdfunding platforms and, and debt, uh, raising platforms and such like that. And you know, that's one of the things that I've heard is when when people invest, even if it's a thousand bucks, a hundred bucks or whatever the case may be, they start following the journey. You start that conversation and once they have their wallet open, man, it's easier to get another dollar. But what, what have you seen work really well in cultivating those relationships? Cuz sometimes I think people look at, okay, I got an investor look for the next one. And it's like, no, cultivate it, cultivate that relationship. Like what have you seen?

Rebecca Kacaba (00:08:34) - Well, I think that's exactly right. And, and you know, the space to know that you're asking that question. Like we built a software exactly for what we saw our most successful clients doing that way. It's called sh you engage, right? Yeah. You engage that community, you send them videos every quarter, you keep them posted. Like I do that with my investors anyway, right? I don't wanna talk to every single person. So I send them a quarterly update. They love it keeps them engaged in the company. You put an ask in that and they respond and they wanna be helpful. They wanna help make their investment successful. So it's that continued reengagement. We've seen companies like Meso Robotics over probably four or five rounds raise upwards of 65 million. Yes. Like we're talking big numbers. When you continue to reengage with your audience and just keep them in the loop, um, the trend we call it is impact investing, right? People want to make investments in companies that they believe in, that they believe are making a great difference in the world, and it becomes part of their own personal day-to-day. Hey, I'm an investor in Netflix, I love what they're doing, I love what they're building. I love how they're disrupting an industry and I feel good that I'm a part of that.

Josh Wilson (00:09:46) - Yeah, yeah. The the the way to, I guess, um, build those relationships, what have you found is a good way to start that, right? So here I am, Josh, I'm gonna, I'm gonna raise 5 million bucks and I come to you and I say, Rebecca, I need some help. You know, I've got, I've got a community, I've got 20 something thousand followers here, I've got followers here, but I'm looking to raise some money, but I wanna do it for good purpose. Let's just say it's an impact thing. But how do I start that conversation? I've never asked for money before. This is my first time funding. You know, like, yeah. How would you guide me through that kind of thing? Or what, what advice do you have you seen work really well?

Rebecca Kacaba (00:10:21) - Well, our digital marketing team, deal maker reach, I mean, they do this stuff all the way down to the analytics. They're, they're monitoring the reactions on the first emails you send and tweaking the messaging and understanding how to position it to get that deal done. But the first thing is you gotta make the ask. Like people are there for it. You just gotta ask. And then I always tell people like when, when I see founders who are meek in their ass, like sales is seven touch points, right? Don't think you're gonna get it there on the first ask. You gotta follow up. And you followed up some of my investors who ended up writing big checks. I mean, I probably followed up with them upwards of 15 times.

Josh Wilson (00:10:58) - Yeah. Most people stop at maybe one, maybe two. I don't wanna bother people, I don't want you. Right? Like that's the kind of the mindset. But you know, the deal research has shown seven touches to get a sale, especially if you're going complex or something that's expensive, you go 15, why? What sets you apart to go double what it's normal to get a yes. Like why does your brain work that, that says that's okay. And I know I'm not bothering them. Like how does your brain work? Explain that to us.

Rebecca Kacaba (00:11:31) - To me, you just gotta read the room, right? Like if they're telling me no, I'm not gonna waste my time, time is my most valuable asset, so I'm gonna use it wisely. But if they're a little bit interested and they haven't given me a note, I just haven't figured out how to get them to guess yet. I haven't given them the right messaging. That's exactly what a reach team is doing. They're monitoring, they're tweaking the messaging until you can get a person to Yes.

Josh Wilson (00:11:55) - Yeah man. And, and, and unless you get an explicit no and sometimes a no is just ask me again later. Right? But like knowing how to read the room, give us some clues on reading the room because some of this is done digitally, right? So teach us how to read the digital room.

Rebecca Kacaba (00:12:13) - Yeah. So I mean I have some, every room is different, right? I have something that I dubbed when I was raising capital called a Canadian No. Which is like, they never directly outright say no, they'll just like string you along because they're trying to be polite. Actually it's really annoying and it's a huge waste of time. Like, just tell me no so I can move on to the next person. Yeah, yeah. Um, you know, but digitally is is a whole different thing, right? People like stories that they can connect with, they like stories that, um, are on trend right now. So depending on what's going viral on the internet or what the bigger trend is, you can position your story that way. For example, um, when Silo Ibin was big, we had a lot of silo ibin companies. As that trend started going down, the element that you wanna focus on in those stories is really how they're changing the world.

Rebecca Kacaba (00:13:03) - Like some of them are curing cancer, some of them are working with professional athletes to rehabilitate them after their careers. And so it's those elements of the story that people can really connect with. And so AB testing, you know, the same thing as continual learning is the key to it is listening to your readers. One of the biggest things I've always done is when you do get an investor, Hey, what'd you like about my story? Why did you invest? And then you wanna take that message cause you know it worked and then launch with that message even bigger.

Josh Wilson (00:13:36) - That's so good. And I think the deal junkie in me sometimes I get the client, I get the investor and then I'm looking for the next one cuz I'm a hunter, right? But the cultivation of relationships, especially as I'm getting older, especially as you know, my kids are getting older and I'm losing time, right? I know that, okay, I got some, you know, I've got someone on my team now I got a partner, I got an investor, let's find out and learn from them. So the next one I could get easier or I could get more and I could do more, right? Like, uh, so that's such good wisdom. Thank you for sharing that with us. Let's talk about the Canadian No, because in, you know, here in the US in the VC world when I was working there, we get a lot of tire kickers, right?

Josh Wilson (00:14:17) - They're like, they had no intent. It didn't invest, you know, it didn't fit their investment thesis like when an entrepreneur was pitching, but they don't say no because they're like, this might be a unicorn, let's just string them along. Yeah. And I hated that that wastes so much time and energy cuz the entrepreneur gets so excited they go to their mom, Hey, I spoke with the VC and they didn't say no and they said to keep a keep them updated and that they're excited. But that still, it's same thing. It's a tire kicker. It's the Canadian, no, how do we get to a no faster so we don't waste our time when we're raising money.

Rebecca Kacaba (00:14:52) - I think that's a really important point because when people look at equity crowdfunding, they say, are the campaigns raising what they want? They target 5 million. Did they hit it? Did they raise three or two? The amount of time we've all burned talking to vs. Who don't end up investing or the amount of investment bank deals that go public and then the share price drops or they try to raise money and they don't succeed. A lot of times with equity, proud funding and that digital messaging, if you're learning and you're tweaking your message, you can raise something. And that's a lot different than burning a bunch of time and raising a big fat zero. Yeah. So that's a really a big difference in the space. Yeah. Um, pointed questions are always great, right? Like, does this fit your thesis or not? Um, get them to know faster and ask them what their criteria is. Have they made an investment in this space? If it's one of those bigger folks, how many checks do they write a year? So if they're looking for that one or two opportunity, your chances of success are a lot lower. And asking what their investment thesis is is huge. Because at the end of the day, if it doesn't meet their thesis, just like you said, they're not gonna write a check. They're just interested in learning. But the company,

Josh Wilson (00:16:03) - Yeah. Uh, so good following someone's investment thesis is, is so valuable cuz it's like, let, let's give it you, you, you mentioned, you know, being able to buy shares just like you could buy shoes online, right? So, you know, when you're going look for a pair of shoes, if someone's trying to sell you a hat and you're like, I I came here for shoes and you're trying to sell me a hat, not a fit. And it actually becomes a turnoff and you lose credibility in that. So when it comes to investment thesis, like it, why don't you explain to us, actually, I should have start there. Explain to us what investment thesis is and why it's so valuable to try to figure out the fit of the investor.

Rebecca Kacaba (00:16:41) - Yeah. So if you're going and talking to like VCs or growth funds or professional investors, a lot of time they raised money telling people on a specific investment thesis, this is how I'm going to get you returns. And so if you don't meet that thesis, maybe it's a fund for simplicity's sake, maybe it's a fund for natural resources. And so if you are not a natural resources company, they don't really have authority to go outside that box because what they've promised to their investors is they're making the money on natural resources. They said they're a pro in investing in natural resources. So if you're not in that thesis, it's gonna be very hard for them to go inside. I've always found Angels family offices, they don't have investment thesises. If you have a good bus business, they're much more likely to invest. That's the same with retail and equity crowdfunding, right? It opens up the capital markets because these people don't have such a defined thesis, they're looking for a different thing.

Josh Wilson (00:17:38) - Yeah. So this is such a good point, right? So some with, with VCs or some specific investment bankers, they have their niche, they have their, you know, their thesis and they're really good at, you know, IOT or you know, a whatever, right? AI or they're, they, that's their niche Family office and angels, you know, they're a little bit more maybe opportunistic and they might have their industry sectors that they've, they like, but you know, it it's, it's going after maybe a specialist over here for maybe more of a generalist to get you up off the ground. Let's talk the different levels of maybe investments. We got Angel, family, vc, investment bankers, and then, you know, as we get much higher, we might be talking to a SPAC or an I P O. Like where does your company find the most, um, like favor? Where do you guys enjoy the most?

Rebecca Kacaba (00:18:31) - Well, we have people using us for all kinds of rounds, backgrounds, early stage angel rounds. Um, we're seeing retail capital raising these community rounds, really forming a compliment at various stages. We've got public companies using it. We've got kind of series B level using it. You know, Picasso, that's one of America's fastest growing unicorns. They're, they're our newest client. They're using it. Um, so we see all different elements of the game and I, I think you've just gotta go out there and figure out who your story resonates with and then put together a funding strategy for yourself that makes sense. If you've got a business model that's gonna appeal to the VC community, that's great. You can stack up with VC into growth capital, eventually go public. If you've got a different kind of story, then you're gonna put together a different kinda strategy.

Josh Wilson (00:19:23) - Yeah. So from lawyer to tech founder, c e o, right? Like what were some of the, the differences and changes? Did you ever like, while going to school, like, Hey, I'm gonna be a, uh, you know, cap cap attorney and now one day I'm gonna be a tech founder. Was that ever in your mind that you were gonna head this direction?

Rebecca Kacaba (00:19:41) - Tech? No, not really. I mean, I was always, uh, very entrepreneurial. Yeah. My dad was a lawyer and started a couple of different businesses. So you could say it's in my blood. Uh, both my sisters are lawyers. My uncle's a judge, so , I like,

Josh Wilson (00:19:56) - Oh my gosh,

Rebecca Kacaba (00:19:57) - I like to joke in my family that you can do what you want after you get a law degree.

Josh Wilson (00:20:02) - . Yeah. That's awesome. Are are there, I would love to like, all right, we're sitting down for dinner. You got your, you know, uncle, the judge dad, the, the attorney sisters who are at the attorney. You're the attorney, right? Like sitting down at the dinner table, like that sounds so intimidating. Are your like arguments like just like on point and then the uncle like presides, like , this is how it's gonna be. What is it like around dinner table with you guys?

Rebecca Kacaba (00:20:26) - Yeah, no, not really. We get along pretty well. My dad's in the wine business, so that's all we talk about.

Josh Wilson (00:20:32) - Yeah. What, what business is he in?

Rebecca Kacaba (00:20:34) - Wine Alto. Oh,

Josh Wilson (00:20:35) - Nice. That's fun. That's really nice. So, alright, so you, you went through the Strout, you became that. At what point did you go, all right, I, I was an attorney for a while, but now this is, this is the direction I need to go because that's a, that's a, that's a big change. That's a life-changing thing. What, what was the, what was the turning point for you to go, I'm doing this and what were the, some of the fears to go that route?

Rebecca Kacaba (00:21:01) - For sure. I was actually featured in the Hustle, if you know that newsletter as one of, one of the biggest career changes they've ever seen. Yeah. Um, yeah, thinking back on it, a bunch of different things happened at the same time, right? The jobs act came out. I saw an opportunity there, I saw an opportunity to be in a business where I could make a real impact on the world versus just selling my hours as a lawyer. I was, I started a startups practice. I was working with a lot of founders. I was giving them flat fee packages for legal services, which doesn't probably sound that groundbreaking to you, Josh, but like in It's a big deal.

Josh Wilson (00:21:41) - It's a

Rebecca Kacaba (00:21:41) - Big deal. Yeah. Um, so it kind of got the startup bug working with so many amazing intelligent founders. And I had kids and I think when you have kids, you wanna spend your time doing something that is going to impact them in a really positive way. And if you're a mom and you're gonna be away from your kids, you wanna feel really passionately about what you're doing. And I met my co-founder who had been practicing in New York, and we both shared the excitement of what we could do in building out the deal maker business and really building Shopify for the capital markets and how that could change the world.

Josh Wilson (00:22:19) - Yeah. So, oh, this is so good. All right, so we have two attorneys coming together to, to, to form a company like the operating agreements and all of that other stuff. Like, was that like the most intense like formation you've ever seen in your life? Two attorneys coming together to build some a tech company?

Rebecca Kacaba (00:22:38) - Actually it was the opposite. Like we were like, so we, because we know the law, like we sketch out our own agreements, we we're like, we spend like nothing on legal fees. We were just like, oh, that's, we can do that ourselves, that's fine. But that was a big benefit to us because we understood so much of the regulatory landscape. And the difference about both of us is that we understand that and we're looking for ways to make it better and easier to operate within.

Josh Wilson (00:23:07) - Yeah. You're so awesome. You guys are so lucky. So as you guys are, are getting, you know, getting this thing up and running, like what were your roles and responsibilities in the beginning? I mean, you guys were probably doing everything, washing the dishes, taking out the trash, trying to figure out code, trying to figure out the laws in different places, but like, what is your primary role's responsibility?

Rebecca Kacaba (00:23:27) - Yeah, for sure. I was doing, you know, sales customer success deal set up, um, yeah. Handling the clients when the system didn't work. So, you know, sweeping the floor is everything. Um, today I'm ceo so I manage kinda the overall vision and direction of the company and work with the executive leadership team. And my co-founder Matt, is chief strategy officer and heads up our broker dealer. You know, when we were spinning that out, he, he went out and brought all the exams and I don't know that he ever thought he was gonna be, you know, a series seven and, and c e o of broker dealer business. But yeah, that's what we do. We do what we gotta do to keep our clients happy.

Josh Wilson (00:24:09) - Yeah. Holy moly. So many different licenses, so many different legalities. We, uh, man. Yeah. This is so good. Cuz I was, I I was going that route. Everybody, you know, I'm, I'm, I'm a real estate broker, right? Yeah. I'm a I we have an insurance company, we have other few other things, but everybody's like, Josh, you need to be in cap braces. And I'm like, all right, I'll consider it. And I looked at the licenses, it's like, I gotta spend the next 10 years of my life like figuring out this, how to take these tests, right? Yeah. Um, but he did it and he crushed it and he's probably just brilliant dude. Um,

Rebecca Kacaba (00:24:41) - He is, he is. You can put him in anything and he could do an amazing job at it. I'm very fortunate.

Josh Wilson (00:24:46) - Yeah. As, as you're building, you know, like, so here you are, you know, you, you have kids, you're c e o of a company. How, like, give us some, give us some like milestones that you guys have hit 2 billion in, in, in deal flow, which is crazy, right? Like, uh, 800 deals, massive amount of deals. So you guys are getting deals under the belt, large volume, like what other, some of milestones that you guys have hit and maybe employees or growth or, you know, direction of what you guys wanna accomplish.

Rebecca Kacaba (00:25:14) - Yeah, for sure. I think, uh, I was gonna say hitting a hundred employees. We're at about 10 right now when we cross that milestone. Yes. That was huge. That's huge. Um, the acquisition we did last March, so a year ago of one of our partners, the digital marketing firm, uh, they're based in Austin, Texas. We love those guys. They know what they're doing. They're always groundbreaking in terms of like how to leverage the power of the internet to raise capital. Yeah. Just crazy innovation strategies and, and digital models. So our first acquisition, that was huge. We wanna continue that and, uh, and got our site set on some other stuff that can grow the company even bigger. And, um, I think, you know, for us we're, we're power housings our way towards unicorn status. So there's always different milestones along the way and getting there and dominating the US landscape and then moving on to more international jurisdictions is, is really where we set our sites.

Josh Wilson (00:26:13) - Yeah. What are some of the things you talk about, like the, the heart of the investor. I like, you know, like people invest in things that they're interested in, people like that, that they, they have a, I forget the word they have like, um, affinity towards, right? They Yes, they like that. What are some of yours? What are some of the things that you're like, it just makes your he beat and you're like, ah, this is cool. Like, I know you're, you're four entrepreneurs, you've been doing it since the day of, uh, that you like, you know, back in the day of legal, you, you, you love the capital markets, but what are some of the, the things that really make your heart beat?

Rebecca Kacaba (00:26:44) - Yeah, I mean my, my main things are deal maker and my family. So yeah. Uh, that doesn't leave a lot of time for other things, but in terms of investments, I always think real estate's cool. I think all the different real estate models that are coming out there, um, with fractional ownerships are really, really interesting. We have some clients that are doing those models and they're now like dividend and distribution generating. Yeah. Which is very cool to me because especially in the startup world, like typically you see either go big or bust and and exit, right? Yeah. And so I think it's like 13% of the companies that have done equity crowdfunding have actually gone on to do exits from like the companies that started 20 15, 20 19. So it's like not a bad ratio considering it's high risk investing, but with a distribution model, I think that whole thing flips on its head and it's a whole different return for investors, which is very cool.

Josh Wilson (00:27:40) - For sure. For sure. I, I'm, I like real estate and I own, you know, rentals and such like that, but then I also own like shares of like these cool startups that are doing fractional this and that. And like to me, I don't have to deal with tenants, I don't have to deal with like toilets and, you know, all that other stuff. It's so fun. And I could examine it on my computer anywhere in the world, in our, you know, going camping with the wife there or doing whatever. Such a cool, fun world, isn't it?

Rebecca Kacaba (00:28:08) - Yeah, it really is. Yeah. It really is. And you can divide it up and exactly as you say, you get the benefits of real estate, but you're not doing all the management stuff.

Josh Wilson (00:28:15) - Yeah. Super fun. Let me ask you this, this is, this is a little selfish of me, but I have a 10 year old daughter, a five-year-old son, and a three-year-old daughter. So I got two daughters, right? And, uh, one day they're gonna maybe come work, you know, for you and I'll work for them or whatever, but like, give me some advice on raising a female entrepreneur. My, my daughters are super entrepreneurial. Like they're talking to me about lemonade stands and you know, creating art and selling it and such like that. Give me some advice that I could share with them.

Rebecca Kacaba (00:28:44) - Bam. You got it. My girls are doing lemonade too. That's it.

Josh Wilson (00:28:48) - So cool. Right? Yeah.

Rebecca Kacaba (00:28:50) - I I think you gotta make it fun. Like they've gotta get out there and hustle and I see my six-year-old flagging people down with their cute little pigtails and trying to sell them lemonade.

Josh Wilson (00:29:00) - Super cute.

Rebecca Kacaba (00:29:01) - I think like enjoying that cold calling is a huge part of building a business and, and that sales aspect to it. Yeah. So I think making that fun is a really core piece of it. One of my daughters was really into writing, so I encouraged her and she wrote a book and we found an, um, illustrator on fiber and then she published a book and she got to give it away. And I think she got a lot of gratification outta that. Sure. And really making business fun because you know what, like, you know Josh I know, but a lot of people don't know, like being an entrepreneur, being in business, it's really fun. Yeah. And it involves some risk, but if you enjoy the risk and you don't mind falling flat on your face and you know that's a part of life, then it's not a big deal.

Josh Wilson (00:29:45) - For sure. For sure. Making business fun. Um, yeah, my daughter, you know, wrote a book and we sold it on LinkedIn. She, you know, one book, one copy 20 bucks and she was like, oh my gosh, I created something and sold it. And that was so fun. So now she's thinking I could create bracelets, I could create, you know, like, but you know, like I think sometimes as an entrepreneur and you talk about falling flat on your face. I've been in DC and private equity, I built millions of dollars worth of stuff. I've also been bankrupt, I've been on food stamp, had to move back in with mom and dad. I think, you know, I'm a, I'm a risk taker. Obviously I'm an entrepreneur through and through. I can't go work for corporation. I just, it's just not gonna be a good fit. Um, when it comes to falling on, on your face, give us some advice right on, on some of the things that maybe from a, a personal experience or something that you've seen on how to maybe shore up so you don't maybe have to hit as hard as I did or how to get back out if you do hit your nose like I did.

Rebecca Kacaba (00:30:42) - Yeah, that's good. I mean I think that's a key part of it. I try to permeate that within the deal maker culture and values all the time. That done is better than perfect. Um, we don't care about mistakes as long as we're learning and having an ongoing learning mindset. I had a girlfriend that was doing like a health and beauty business and she cut a bad deal and she was paying a lot of money to partner and she was being really hard on herself about it. And I said, you gotta look at that couple hundred thousand dollars that you feel bad about losing cause you paid to someone else. That's just the cost of that lesson. Yeah. And if that lesson causes you to cut a better deal next time and you make a million bucks, that's money well spent. So don't be hard on yourself about it. There's no point in being hard on yourself about it. You're not gonna be perfect every time. Yeah. And just learn from it and it was worth it.

Josh Wilson (00:31:37) - Yeah. That's so good. Is counting your losses as a lesson is, is so valuable because I've made some mistakes and I share them openly and the more that I share it's weird. The more I tell people about my failure, some more they show up with money

Rebecca Kacaba (00:31:54) - For sure. Cause they know you take risks.

Josh Wilson (00:31:56) - Yeah. And in that, I'm, I'm open about it. And I think that entrepreneurs, you, you talked about the beginning about cultivating the relationship with your investors, communicating often to them, and I'm learning to do this much better. But like, I think when times get tough, we tend to go, Ooh, I I I need to fix it before I could talk with them about it. But talking with them through the problem, a lot of times they could help. Right.

Rebecca Kacaba (00:32:21) - Totally.

Josh Wilson (00:32:22) - And you know, like a making the ass. So, oh, I, I love this. This is, thank you so much for jumping on this interview cuz I'm gonna pull so much outta this is we ask for money and we gotta learn to ask and you're, you're really good at it. You're like, I'll ask 15 freaking times to get to a yes. Right. Then there's other ask, once we have them in that relationship, what are some other ask along the way that founders need to get comfortable asking from their investors?

Rebecca Kacaba (00:32:49) - Yeah, I'd love that. It's so key. We're building this right into the product so everybody does it every time. Because when you send your quarterly updates, and I'm guilty of it too, Josh, like I don't ask as much as I should. I don't do as much as my investors would do for me because I'm always running around trying to build the business. But in those quarterly updates, what is your ask? What do you need? And ask those people for it. Like I had, one of my investors came to me when this Silicon Valley Bank failed and he said, Rebecca, do you guys need a loan? Like I, I dunno if this affects you, but if it, if it does, I'm here for you. And that was so nice. Like I didn't even think, and then I said, you know what? I have to send an update to all my investors.

Rebecca Kacaba (00:33:28) - Yeah. They're probably wondering if this affects me, I gotta communicate with all of them. It doesn't affect me at all. But they don't know that I'm a tech company. Maybe I did do something with Silicon Valley Bank. So it's just that communication and the more you communicate with people, like, you know, you're out there hustling, you're building businesses, the more you're out there communicating, the more things happen. And you can do that with the people. It's like upselling your existing clients. Right. What's the best way to make more money? Take a client, sell them more stuff. So you already have an investor, take that relationship and cultivate it more and you'll get more outta it.

Josh Wilson (00:34:03) - Ah, that's so good. Now on the, on the flip side, as an investor, right? Like we invest into a company or a deal and you know, like we're, because we did it because we trust in the person. We, we like the idea, we have an affinity towards the direction that they're heading and we're sitting there waiting, chomping at the bit to help and add more value. Now the founder on the flip side is going, oh, I don't want to bother them. One person saying, I wish they would ask me for more. Cuz I, I, I have connections, I have experience and maybe they're retired and they're going, I'm bored, I want to dive in. So it's just like crossing that over. And this is a, this is something that I learned from podcasting and interviewing people. Uh, I, I forget who it was, but they, they make consistent ask from their investors even if they don't need something specific cuz they want to get them used to being asked for something. One of the first things they do. Hey, as we're sending this out, would you mind taking a look at these docs and just giving us your feedback? Hey, will you take a look at this? Will you like and comment on this and maybe share it with your community. Will you listen to this or read this book? And it's just like, they're consistently so when they need the big ask, these people have been like prepped for. And I was like, that's genius. That

Rebecca Kacaba (00:35:12) - Good is genius. That's genius. We could all learn from that.

Josh Wilson (00:35:15) - Yeah. Oh my gosh, you're, you're awesome As what did, what was the biggest thing that you had to learn from going from the legal side? Like, you know, the, you know, I want the truth legal, you know, like I love those movies kind of Right. The legal movies. But like from that to c e o, what was the biggest growth that you had to do? Personally?

Rebecca Kacaba (00:35:35) - That is a great question. To me, I think it was communication and talking things out and realizing when people aren't on board with you. Like, I like to move really fast. Right. And as the company grows, communicating and making sure the whole team is growing in the same direction is a bigger part of my job. And so that really involves talking to people and making sure they're on board. And both my co-founder and I, we like to make things happen and we like to move quickly. Sure. But sometimes part of moving quickly is listening and communicating, which kind of feels slower sometimes .

Josh Wilson (00:36:13) - Yeah, sure. Does it it sure does. Cuz you're now leading a hundred people or 110, right? Yeah. When it's like, when it's just you the solopreneur and you're like, oh, have an idea, boom, you could fire off. But now you're like, oh, I have a c o o I have a chief strategy officer, I have management, I have three. You're at three levels of management at this point, right? Or two? Yeah, yeah,

Rebecca Kacaba (00:36:36) - Yeah. About two and two and a half. Yeah. Three

Josh Wilson (00:36:39) - Some places. Yeah. So it's just like, you just can't go to the bottom row and go like, here, do this. It's just like, wow. It, that's a huge change in personal growth.

Rebecca Kacaba (00:36:49) - Yeah. Because otherwise the whole house will like start tore and fall and you can see it when it's happening, when it's not all going in the same direction and you gotta keep bringing it back together to make big things happen.

Josh Wilson (00:37:00) - Yeah. What was the hardest point of that for you? So you talked about going slower communication chain of command in learning that like in that where you look back and you go, wow, that was the biggest thing that I overcame in that journey.

Rebecca Kacaba (00:37:17) - Yeah. For me and my personal communication, that was it for sure. I mean, in starting business there's all kinds of rocks and boulders you have to move and Sure. Um, using creative problem solving to get through those things, those were some of the hardest things. And you know, one day my co-founder and I write a book about it and some of those late nights and like brainstorming we did and way we made the business successful come hell high. Um, but those are the good days. Those are the days in the trenches.

Josh Wilson (00:37:48) - Yeah. All right, so you got kids, so let's, let's fast forward 50 years, right? Y uh, you know, we're looking back and, you know, we're on the end of our journey and we look back and we go, this is the thing that I was most proud of accomplishing. What was that for you?

Rebecca Kacaba (00:38:03) - For me, that'll be, if I look at the capital markets landscape and I see retail capital raising as a component of it, and I see that founders in North America can reach pools of capital in Germany or in India or in different places. If we've succeeded in making the capital markets move more fluidly and bringing more capital into them, that gets more founders funded. And to me that's, you could never have a bigger impact on the world.

Josh Wilson (00:38:33) - That's super cool. There's so many dead ideas because they didn't have access to capital. Um, not everybody has rich uncles and aunts. Not everybody has friends and family that ha that have money. And uh, there's a lot of good ideas that could change the world that just need a little bit of support from investors. And there's investors chomping at the bits because they might hate the stock market. They might not know how to invest in real estate, but they're really good at sitting behind a computer and finding good opportunity. Right. And I, I think that that is, um, I think you're making an impact and I, I'd love to see that happen for you guys. Um, let's talk through an ideal client for you and their journey of, of how you serve them.

Rebecca Kacaba (00:39:09) - Yeah. So a lot of our clients are basically companies who have capital needs. They're gonna need to do multiple rounds and they can build a community around that business and they wanna continue to go out to that community. Similar to what you described, how we get those clients is really through partners. So lots of investment bankers, angel investors, venture capital partners, family offices, private equity. Lots of times it's people saying, I'm not gonna do this round guys talk to deal maker. Maybe you wanna do a retail round. Maybe we're gonna sidecar, we'll put 2 million bucks in and you can raise 3 million equity crowdfund. So that's really an exciting change in the market that we're seeing. We're only in the second inning of this. We've got some big, big brands coming out this year that are gonna continue to move the needle in terms of this kinda capital raising.

Josh Wilson (00:40:02) - Yeah. So who is this not for?

Rebecca Kacaba (00:40:06) - Um, it's not, who is it not for? That's a good question. I think it's not for businesses who are generally not synced for taking investment because they don't have that growth plan. They don't have some end game of a liquidity or a distribution plan. So, you know, small mom and pop coffee shops that are gonna make a little bit of money, but there, there's not really gonna be an exit there.

Josh Wilson (00:40:33) - Yeah. So multiple rounds to a, some, some form of exit. Right. This isn't for lifestyle businesses. Hey, I need a hundred grand to build a flower company. That's, that's awesome. There's other paths for you. Yeah. Hey, I wanna build the company cuz I, Josh wants to build it and exit. Yeah. And I know I'm gonna have to go through six rounds of funding to get to an I P O or whatever the case may be. Right? Yeah. That's, that's when you're like, okay, let's take that journey. Let's start building the investor community. Let's build your investment path, let's start having those conversations along the way. That's, that's a good fit for you guys.

Rebecca Kacaba (00:41:04) - Exactly.

Josh Wilson (00:41:05) - Cool And good strategic partners, family offices, investment banks, uh, banks in general. What other Yep. Uh, what other people are good as people are listening and what are other good strategic partners for you guys?

Rebecca Kacaba (00:41:18) - Lots of angel groups that we help compliment with. Maybe they're going in on a seed round and they're like, ok, now equity crowdfunding is gonna do kinda the series B series A level ish and beyond. Lots of attorneys who can make their clients aware of this as a funding opportunity. Often that's the person a company's talking to, right. When they're trying to assess options. So just for attorneys to be aware, listen, if that BC rounder, they're stringing you down the path and you're running outta money, you should be looking at equity crowdfunding at the same time so you don't go broke.

Josh Wilson (00:41:50) - Yeah. Do you mind if I ask you like, just an off the wall question that just popped in my head. That's my job as podcast hosts. It's just as things pop in this crazy brain, I'm supposed to ask it. Yeah. What was your favorite childhood memory?

Rebecca Kacaba (00:42:04) - Oh man, I don't think about my childhood a lot

Josh Wilson (00:42:08) - Either. I know it's weird, right?

Rebecca Kacaba (00:42:11) - Probably ski racing. I, I used to ski race competitively, so I like, I like going fast.

Josh Wilson (00:42:17) - Oh, very cool. Like downhill, like on snow.

Rebecca Kacaba (00:42:20) - Yeah.

Josh Wilson (00:42:21) - Okay. Because I'm in Florida, so skiing to us is flatwater in, in, in, you know, behind a boat. Yeah.

Rebecca Kacaba (00:42:27) - That's You're looking at me like I'm crazy. Yeah, no, I do that now. But like back in the day, I, I used to travel a lot and, you know, did the, the f i s international rain competitions and had some really good times.

Josh Wilson (00:42:38) - Wow. So you were really good.

Rebecca Kacaba (00:42:40) - Yeah. Barreling down, you know, and whatever miles an hour with in those days. I mean, you were a helmet, like, that's it. Yeah.

Josh Wilson (00:42:47) - Can you do, like, are you, do you still ski?

Rebecca Kacaba (00:42:50) - Uh, here and there.

Josh Wilson (00:42:51) - Yeah. Could you do like black diamonds and such like that or Oh

Rebecca Kacaba (00:42:55) - My god, yeah. That stuff's easy. I could do that. ,

Josh Wilson (00:42:57) - That's easy. Yeah. , I got that. Yeah. Yeah. So Rebecca, for, for people listening into the audience, like what's a good place to connect with you guys and do a massive fundraising deal?

Rebecca Kacaba (00:43:07) - Yeah, so probably best send us an email info Dealmaker Tech. Uh, we got a really, really knowledgeable team who can walk you through all the various options, whether you're partner looking for capital yourself, connect you with our partners network and, uh, help you get your raise off the ground.

Josh Wilson (00:43:26) - Cool. What does that look like? Could, could you give us some maybe framework in terms of how does it work? Maybe some of the cost involved or you know, like, I don't know if it's deal by deal basis or whatever, but give us some ways to look at like, all right, this is what it would look like.

Rebecca Kacaba (00:43:40) - Yeah. So if you're a partner, you're doing like a background, you're doing your own distribution and filling your deal, you just wanna use the tech. You're looking at like maybe a couple thousand bucks. You can get your deal spun up in 48 hours or less. You're looking at launching a bigger retail round and using all the digital marketing depending on whether you're raising up to 5 million under CF or more than that. Under reg you're looking at audited financial statements, legal costs with an outside advisor and then our tech or marketing or broker dealer fees. Um, so those costs probably more like 30,000 we saved for CF to earmark. And then for a bigger, like a reggae, you're gonna earmark 150 grand to get that raise off the ground before the money starts coming in.

Josh Wilson (00:44:26) - So good. So good. Yeah. I have some friends in the, uh, SPAC world i p o world that uh, that this would probably be a very good, um, like lead engine for them cuz they're looking for deals to, to help take, uh, public and such like that. And then, um, yeah, so you and I should, uh, connect about, you know, those kind of, uh, relationships, but, uh, people in the audience, fellow deal, makers in the audience, if, if this kind of stuff fits for you as always reach out to our guests and say thanks for being on the show. Um, you know, their contact information will be in the show notes, you got info@dealmaker.tech, right? Is the a good way to reach out and just send them a message and say, Hey, this is what we're working on, would it be a good fit for us? And how can you help? Um, Rebecca, during this interview, there's probably a question that I should have asked you that I screwed up and did not ask you. What is that question?

Rebecca Kacaba (00:45:17) - Oh, that is a great question. Uh, I, we covered so much ground. I

Josh Wilson (00:45:21) - Know skiing and all this stuff. Family lemonade stands, SPACs.

Rebecca Kacaba (00:45:26) - I can't believe how similar our kids are. That's awesome.

Josh Wilson (00:45:28) - Yeah, it's cool. Right?

Rebecca Kacaba (00:45:30) - Um, what's the biggest change that I think we're gonna see coming in the exempt markets over the next year?

Josh Wilson (00:45:37) - Great question. We're in a bunch of different shifts and changes. What do you see for the future?

Rebecca Kacaba (00:45:42) - Yeah, I think as online capital raising grows, the analytics and the power of the digital is growing in power because the analytics are getting stronger. So with us closing close to 2 billion in capital now, the analytics we have on where investors are based, what kind of deals they like, what kind of check sizes they're writing Yeah. Into different kinds of deals. That's huge for our partners network. And we've got tons of folks leveraging that already for their own knowledge and and practice. I call it like, it's like private information like a Bloomberg and before capital raising moved online, this data didn't exist. Now as it moves online, the data is gonna power the entire industry.

Josh Wilson (00:46:26) - Yeah, yeah. Cuz you're seeing companies like PitchBook, you're seeing Crunchbase and, and these different groups that are kind of earmarking the raises and they're, and they're showing that data is so valuable, especially if you're raising money. You can go to you guys and say, how do I buy new investors? And what are they investing in? Where's money not moving? Where is money moving? That's so valuable. Um, do you ever think I got another question? My, I I, I lied. I'm, I'm, I'm, I'm keep on going. Um, do you ever think that your stuff would be valuable for non the non-profit world for, you know, donations and raising money for donor campaigns and such like that? Do you think you'll ever see that?

Rebecca Kacaba (00:47:07) - Well, that's a really interesting question because if you look at the trend of impact investing, the newer generations are really coming, bringing corporation and donation together as one. So they expect to see the investments they make have a material positive impact on the world, and they're actually less likely to straight up donate to charities. And so that is a new movement of the younger generations in the way that they're viewing the world. And so you see a lot of different kinds of corporations developing as a result.

Josh Wilson (00:47:40) - Yeah, that's interesting. So for the nonprofit world, they need to start paying attention to that and, and where the money's going and maybe some type of corporate path or corporate relationship. Right.

Rebecca Kacaba (00:47:51) - Bingo, the ones that are doing well have a sustainable business aspect because the younger generations are saying, I'm not just giving you money for it to disappear, like do something with it.

Josh Wilson (00:48:02) - Yeah. So good. Oh, that could be its episode in it in itself. But Rebecca, fantastic interview, uh, such a great time connecting with you and, and learning more about you and the business. Uh, one more time. Where could people go to, you know, find more information about the company? What's your website?

Rebecca Kacaba (00:48:18) - Dealmaker.tech? Or they can send us an email@infodealmaker.tech.

Josh Wilson (00:48:23) - Cool. Rebecca, you're awesome fellow deal makers. As always, reach out to our guests, say thank you. Find a way to connect with them, do a deal or add value to their world. If you have a deal in the audience that you would like to talk about here on the show, the deal scout.com, fill out a quick formm and maybe we'll get you on the show next. Love you guys and we'll talk to you all on the next episode. Bye everybody.