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Shark Tank Winner Jayla Siciliano Pivots Into Luxury STRs (Ep 624)

Ep 624`

Jayla Siciliano, former Shark Tank entrepreneur, shares her experience on the show and the challenges she faced in building her wine company. She discusses the importance of staying focused and not spreading oneself too thin. Jayla also talks about her current business in the short-term rental industry and the challenges of managing multiple properties in different locations. She emphasizes the need for strong systems and processes and the importance of customer service in the hospitality business. Jayla Siciliano, founder of Atlas Vacation Rentals and host of the Seed Money podcast, shares her journey as an entrepreneur and offers insights into the short-term rental industry. She discusses her love for design and hospitality, and how she focuses on providing exceptional experiences for families and groups. Jayla emphasizes the importance of joining mastermind groups for support and guidance in the early stages of starting a business. She also provides advice on raising seed money and making decisions about funding options. Jayla's story highlights the significance of aligning your goals and values with your entrepreneurial pursuits.


Building a business requires resilience and the ability to pivot when necessary.
Staying focused and not spreading oneself too thin is crucial for success.
Strong systems and processes are essential for managing multiple properties in the short-term rental industry.
Customer service is a top priority in the hospitality business. Passion for design and hospitality can drive success in the short-term rental industry.
Joining mastermind groups can provide valuable support and guidance for entrepreneurs.
When raising seed money, consider your end goal and whether it aligns with the expectations of investors.
Convertible notes and safe notes are simple and cost-effective options for raising friends and family rounds.
Making decisions about funding should be based on your long-term vision and the needs of your business.
Stepping away from a business requires deep reflection and the courage to prioritize your values and goals.

Apply for our Revenue & Pricing Management Service here.

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Click here to listen on Apple Podcasts.

Read The Script Here


Jasper Ribbers (00:01.29)
Welcome back to Get Paid for Your Pad. I am very excited because I have an amazing guest today. Her name is Jayla Siciliano. She is the host of the Seed Money podcast. She's a real estate shorter rental investor. She's also a former Shark Tank entrepreneur. She got a deal with the famous entrepreneur Mark Cuban, and she's currently on a mission to help early stage entrepreneurs take the next steps to turn their ID into a reality. Jayla, welcome to the show.

Jayla Siciliano (00:30.286)
Hi, thank you. So fun to be here. Thank you for having me.

Jasper Ribbers (00:33.034)
Yeah, yeah, I'm so excited. I've seen some episodes of Shark Tank in the past and it's very fascinating. And I'm super excited to learn a little bit more of the ins and outs and maybe some behind the scenes stuff that we don't necessarily see on the TV. And I would love to also hear your story of the companies that you founded, your experiences. So yeah, without further ado, let's dive.

into it. I know you also manage 20 luxury short -term rental properties. So we'll touch on that as well. But I'd love to learn more about your experience. Let's just kick it off with Shark Tank. How did you get involved with that?

Jayla Siciliano (01:12.27)
Yeah, I'm an open book, so happy to describe any of the juicy details. I had founded a wine company, and I raised money through private investors to kick it off the ground. The short story is I ran into some massive production issues out of the gate. And I was faced with having to go out and raise more money, which was challenging, you know, after you've raised a first round and run into all these production issues.

And one of my advisors kept bugging me to go on Shark Tank to apply. And I'm like, I don't want to go on that show. And then I finally had to go meet him again for coffee. And I was like, I just need to apply so that he stops bugging me. So I applied. And you know, sure enough, I think it was like eight months later or something, I got a call from one of the producers jumped through a lot of hoops, you know, to get on. It's a pretty intense application process.

and ended up getting on the show. And it was even the leading up to getting on the show was a roller coaster. So it was just a crazy experience, you know, overall. Definitely very intense. Looking back, kind of can't believe I did it, you know, one of those. But yeah, happy to expand on it or, you know, however much you want me to share. I'm totally happy to share. I can give you the whole story or, you know, nuts and bolts of it.

Jasper Ribbers (02:29.322)
Mm -hmm.

Jasper Ribbers (02:40.234)
Yeah, well, for there might be some people listening who haven't seen the show, like, could you explain briefly what the show is about?

Jayla Siciliano (02:46.83)
Yeah, so essentially, you have entrepreneurs who get up in front of a panel of investors. It's the, you know, rotating, I think seven investors every episode, and entrepreneurs get up, they pitch their deal, and they get asked a ton of questions. And the investors decide if they want to invest or not. The crazy part is, you know, the show when you watch it is about 10 minutes, your clip 10 to 12 minutes, but you're actually I was in there for over an hour.

and they edit it down to that 10 minutes. So yeah, I ended up getting a deal with Mark Cuban. I think I've heard all the sharks are really great. They say sharks, but they're really all in it for the right reasons. They're very involved. They contribute tons of resources outside of just money to these businesses. And the marketing exposure you get, they've got huge.

viewer stats. So it's just a huge injection of marketing to your company, which is the really cool part.

Jasper Ribbers (03:46.634)
Mm -hmm. Were you nervous when you stood in front of those investors?

Jayla Siciliano (03:51.15)
Well, so it's funny, I, a little insight into who I am, I research things to death and I got up, you know, for months before getting up there to actually film it. And I watched every episode, I wrote down every question the sharks asked. I mean, I rehearsed that pitch, you know, I don't know, hundreds and hundreds and hundreds of times. And when I actually went there, you know, they give you your film date.

I'm there in my dressing room trailer, ready to go, you know, finally, okay, gonna get this over with. And the producers come in and they're like, we're so sorry, you're not gonna get to pitch today. We don't know if you'll get to actually do the show. And it was just one of those like, what? You know, wasn't expecting that, didn't know that was a possibility. Drove home. And it was just a surreal moment of, you know, you practice so much for something to not even be able to get it off your chest is kind of, you know, a –

such a downer, right? And I was like, okay, whatever, you know, keep pushing along. And a few days later, the producer called and she's like, there's a 50 -50 chance you'll get to pitch tomorrow. Do you want to come up? I was like, I'll be there, you know, so drive up, there I am again in the dressing room waiting. And at this point, I was super nervous before, but I think because I almost didn't have the opportunity at this point, I was just so thankful to get a chance to do it again.

And I was like, you know what, I'm just gonna go into this and try to have fun. This is an incredible life experience. So the way it worked out, I was actually a lot less nervous going in there than I might've been the first time because I almost didn't have the opportunity. But you know, it was still a blur. The producers, they said, you know, if you go out there, if you pee your pants, we're not stopping filming. Like no matter what, once you're out there, they can edit anything into the show that they want.

So it is nerve wracking from that standpoint, just that it's definitely high pressure.

Jasper Ribbers (05:55.754)
I can imagine, yeah. So was it the wine company that you were pitching for?

Jayla Siciliano (06:01.198)
Yeah, so I started, this was, I spent my first part of my career working for Diesel Footwear and Burton Snowboards, both like very heavy drinking culture kind of companies. And I was always really active and healthy. This was in the early 2000s. And I saw a gap in the market for kind of a lighter, healthier alcohol option. At the time, you know, all of these seltzers, none of this existed. It was basically, you know, wine coolers of the 80s, beer and wine.

And so I decided I could do it, you know, very naive. I had no idea what I was doing in the alcohol industry. Decided to just quit my job and go for it. Life is short. Why not? And dove, you know, head first into it, quickly realized like, whoa, this is a bigger undertaking than I anticipated. You know, flew through my savings 401k, all of that. But now it's an $11 billion category, huge, you know, huge.

category in the alcohol space. But I was definitely kind of one of the first ones to try to push that along, which isn't easy to do. You know, creating a new category, educating customers and stuff like that is expensive and challenging for sure. So, but great experience.

Jasper Ribbers (07:05.802)
Mm -hmm.

Jasper Ribbers (07:13.77)
Yeah. Yeah, it's interesting. Like when, at least for me, when I started as an entrepreneur, I thought it was all about having the best idea. Right. So I was like, okay, I just got to come up with a brilliant idea and then like everything will work out. Right. And then you realize like, okay, and the deer is really like nothing. Right. I also, I love the founding story of Airbnb because they were so close to not getting the company off the ground. And it just, it just.

Jayla Siciliano (07:23.086)
Mm -hmm. Mm -hmm.

Jayla Siciliano (07:28.078)
Thank you.

Jayla Siciliano (07:32.366)
Look at the ice cream.

Jasper Ribbers (07:43.178)
reminds me of that concept of you can have a brilliant idea. Clearly Airbnb was a brilliant idea, if you look at it now, right? But it was so hard to make it happen, right? So yeah, so you pitched this idea to Shark Tank, to the investors. What was the response from the investors that you were pitching to?

Jayla Siciliano (08:06.542)
It was mixed. You know, Damon John was like, you're gonna need way more money. He had invested in I think maybe a tequila company or something. So he knew the alcohol industry pretty well. He was like, you're gonna need millions and millions of dollars. Mr. Wonderful, he was actually in the wine industry. But this again, not being regular wine, he was just like, I don't know about this. I'd like to help but I'm not sure.

And then Mark Cuban ended up basically saying, you know, I think my wife would love this. People do want to be healthy and want to drink. And, you know, I think he saw how much I'd put into it just as an entrepreneur effort wise, and he decided to invest. So overall it was good.

Jasper Ribbers (08:50.186)
That's amazing. And then on the show that that's announced, right? So on the show, Mark Riemann was like, okay, I'm going to take the leap. I'm going to invest. Do you hear the amount right away or?

Jayla Siciliano (09:00.622)
Yep. So you go out asking for an amount. And at that point, again, I was on the verge of like possibly going out of business because we had all these issues. So you do have to pick evaluation when you go on Shark Tank. The previous round, I raised about a half a million as convertible notes where you don't have to pick evaluation, but on Shark Tank you do. And they will just chew you up if your valuations, you know, ridiculously high.

So I looked at it, my previous investors, we all saw it as a really strategic opportunity to get airtime on the show, to get an influential investor. And so we went out there asking for 150 ,000 for 35 % of the company, which is like nothing, right? So Mark, you know, there was no negotiating. I think he was like, okay, that's as kind of low as you can go. So he gave us that amount. But again, with all the resources and stuff that he

you know, provided it was really so much more about, you know, all of that than the 150 ,000. And he did end up financing inventory runs for us also. So he sort of acted as a bank, which was super helpful.

Jasper Ribbers (10:10.026)
Mm hmm. And so how did the how did it turn out the business?

Jayla Siciliano (10:14.062)
So it was a few years of really going crazy, grinding. I was traveling constantly. Just the alcohol space could not get it profitable. I mean, you're giving your distributors 30%, your retailers anywhere from 20 to 40%, having to do tastings, just a very expensive category to be in. And looking back also, I mean, there's so many layers and complexities to

how this kind of went about, but in a nutshell, essentially, I just got to the point where I was gonna have to keep raising money. With every round, I got diluted more and more, and I was just killing myself. And my husband and I had put off starting a family. And I really got into this because I wanted, I saw a need for the product, and I actually wanted more freedom and flexibility than working in this corporate job.

And I basically woke up one day with my own company going, I'm miserable. And I'm just killing myself. I'm working like crazy. I'm traveling like crazy. We're going to have kids. I don't want to be the mom that's gone all the time. And it was a very, very hard decision, but I had to make the choice to basically walk away. And I had the support of all my investors. They understood. I think the market timing was really key there too.

had I known that that category was gonna completely take off, like White Claw came out the year I closed the company. And they really like blew up the space. They had the marketing dollars, the distribution. And so, you know, had I known that that was about to happen, maybe I would have pushed through, but still it just wasn't the right thing. I had high blood pressure, you know, I was super stressed. And so it's funny, that's how I kind of ended up, you know,

Jasper Ribbers (11:49.674)
Oh wow.

Jayla Siciliano (12:10.126)
now being in real estate, while it's not this sexy product in wine, it really gives me the true lifestyle and freedom that I ultimately wanted, you know, when I first started that. So it's, it came full circle. But yeah, it was, it was definitely a bummer, very painful, you know, to go through that. But I've learned now it's, it's part of entrepreneurship, you know, many.

The more common story is entrepreneurs who have to pivot and face making that decision. And it's a tough one, not fun, wouldn't wish it on anyone, but incredible, you know, makes you stronger for sure. And you grow so much and get great experience out of it.

Jasper Ribbers (12:52.17)
Yeah, I was talking to a business partner the other day and we recognize that the only constant in our business is change. You know what I mean? But yeah, it's, you know, it's, it's, it can be very difficult to deal with the uncertainties and like the doubt, right? I'm sure you in your journey, like you probably ask yourself multiple times, like, is this really worth it? Like, you know, the, you making a lot of sacrifices to, to

Jayla Siciliano (13:00.462)
Yeah. That's true. That a roll.

Jasper Ribbers (13:21.77)
make this dream happen. What are some of the biggest learning lessons that you got from that experience?

Jayla Siciliano (13:29.902)
You know, I would say the biggest learning lessons that I fortunately did learn from and have, and I'm doing differently now in this short term rental business. One, not allowing myself to get burnt out. I think I, you know, my dad was an entrepreneur and I grew up.

around more that mentality of like, you got to do everything yourself, you know, that kind of thing. And in that business, I was wearing so many hats. I had a team, I had employees and stuff, but it was, I still just felt this pressure that I had to be doing everything, you know, and I'm doing that very, very differently. Now I've, I've gotten a team who's experienced delegating. I've gotten so much better at that. The other thing is I think staying focused.

That's something I really wish I had done differently. We were doing online sales. We were selling at wholesale to grocery stores off premise, and we were selling on premise to bars and restaurants and clubs and resorts and stuff like that. And multiple states, shipping internationally. So just spreading ourselves way, way, way too thin. I think if I had just focused on online sales, which…

Also, online wine clubs were really just gaining momentum, you know, so that wasn't quite as what a thing it is now. But had I focused on online sales, I think we could have gotten farther with less stress, you know, and possibly been more reached profitability. So one thing I've done in the short term rental business now, we actually started growing too fast, quickly ramped up to 30 properties very quickly in like a year. And

was like, wait a minute, what am I doing? Scaled it back to about 20 properties that are all, you know, fit the same avatar, family, more luxury, bigger bang for the buck in terms of, you know, bookings and stuff like that. So narrow, I was in multiple markets, narrowed it down to only two markets. So, you know, that idea of being focused and staying focused and having that discipline is so hard to do, especially when you're just trying to grow.

Jayla Siciliano (15:44.494)
But I definitely learned my lesson there also how important that is. It's a critical thing.

Jasper Ribbers (15:51.306)
Yeah, yeah, no, I can relate to that. And, you know, most of the, most of the companies and operators that they're joined, like some of our programs and masterminds, they typically like, the first thing they do is they let go of a couple of properties because when somebody else looks at the portfolio and ask some questions of like, Hey, this unit is not really making any money. And like, sounds like the owner is giving you a headache. Like why, why are you still managing that? And it's like, yeah, it's a very good question. Well, I guess I'm just afraid to let go of something.

Right. And then the first thing that happens is that people let go of the units that they don't really want to be managing in the first place. So I think that's interesting. And yeah, definitely like shiny object syndrome is something that I think every early stage entrepreneur has where you're so eager for opportunities and you're afraid to miss out on opportunities. And you just like jump on everything that comes your way. You know, in a short -term rental business, we often see

early operators like just kind of taking on whatever they can take on. Right. And then at some point to your point, it's like, what we call the hectic host is like somebody who's like, just has no idea really what they're doing anymore. They're a bunch of random properties and like no real systems and no real brand and you know, none of that stuff. So it's very, yeah, very relatable. So right now you're, you're, you have 20 luxury vacation rentals. Which markets are you in?

Jayla Siciliano (17:16.526)
Santa Barbara County and then Stowe, Vermont. Santa Barbara, California and Stowe, Vermont. So 3 ,000 miles apart.

Jasper Ribbers (17:20.458)
Okay. So like.

And is there any particular reason why you chose those markets?

Jayla Siciliano (17:29.518)
I just love to torture myself. No. I basically I live here in Santa Barbara. So this is we bought our first one in wine country here. And that was early COVID. A few different reasons we bought that one. But looking back, I think, you know,

being right here in our backyard, it felt a little more comfortable. I had had long -term rentals before, but never short -term. And we also wanted it during COVID just as a place to go and get away from our house. So that's what started it here. I grew up in New Hampshire and we were getting ready to buy a second property. And we didn't want to buy one here because the regulations are a little bit up in the air.

and it's expensive, higher price points here obviously. So we were looking in Big Bear, Pacific Northwest, and Vermont. We really wanted to kind of get one in a mountain town. We grew up snowboarding and all that stuff.

And I kept looking at the numbers in Big Bear. Well, Big Bear was having all these regulation issues, Pacific Northwest and Vermont, and it just made sense in Vermont. And we go back there every summer. My brother still lives there. My parents are there in the summers. So we were like, okay, I think Vermont's the spot. We saw this place and we were like, that's it. And it's actually 20 minutes outside of Stowe. And locally, the town it's in doesn't have the best reputation, but it's

this gorgeous property on 18 acres, beautiful ponds, you know, very much that Vermont vibe. And people from Boston and New York, they just want that Vermont vibe. They don't necessarily know the local reputation of the town, right? Like Vermont, or sorry, Stowe is the cream of the crop town, but it's only 20 minutes. So it had all the bells and whistles of someone, of what someone's looking for going there, but it was a much better value than what you would pay for the same, you know, a similar property.

Jayla Siciliano (19:20.014)
20 minutes away in Stowe. And that property is so, and then that just kind of spread, word of mouth started managing other properties in that area. And it's funny, that one actually outperforms a lot of the Stowe properties, which is so it's funny how it works out. Sometimes what you think might be the best location or value to location is worth exploring those little outside pockets for sure.

Jasper Ribbers (19:45.834)
What were some of the biggest challenges that you encountered while you were building this business in these two different locations?

Jayla Siciliano (19:55.982)
I think the biggest one was the systems and processes, getting those set up while growing. Also Vermont, you know, it's really cold. You have mud season, the maintenance there, the maintenance issues there are at least triple what we deal with here in Santa Barbara, you know, so there's just always something there. Mice, bugs, snow, mud, you know, it's something all the time. So having a really strong team there was super important.

And it's funny in the beginning, you don't know what you don't know, right? You just kind of dive in and start figuring it out. And I didn't realize how critical the systems and processes and tech piece of it was and having those things and having a team that was not only utilizing those processes, but helping me, you know, build them out. And so I did have to restructure the team a bit to, you know, really get people who aligned with the tech we're using.

the systems that we're using and make sure everybody's on the same page. And now everything is running so much smoother than it was, you know, at the beginning when not everybody was using the systems. And it was just kind of a free for all. And it was a total hectic mess, but that straightened out.

Jasper Ribbers (21:10.41)
Yeah. Yeah. I kind of mentioned, um, how would, like, I, I feel like the short term rental or in general, hospitality business is, is very interesting because it's 24 hours. There's a lot of moving parts, right? How would you compare your current business to the businesses that you had in the past?

Jayla Siciliano (21:32.078)
Yeah, I gotta say this business is crazy. It is every once in a while, I'm like, it's just so weird that it's 24 hours a day, your customer service is 24 hours a day, you know, I mean, there aren't many businesses where you have to be like that. So, you know, I think from that perspective, it is, you know, it has its element of just that hectic side.

The other thing that I think is a little bit challenging is you've got guests, you've got owners, and then you've got your whole cleaning, all of that staff. So you're catering to a lot of different personalities, right? And so I think that dynamic, and it's just very urgent. With guests, you don't have time to resolve stuff slowly. Everything moves very, very quickly.

Whereas with my old business, you're working with retailers, your end customers, it was a slower pace in that sense. So I do find hospitality, you really have to be on top of it from a customer service standpoint, but there's so many.

resources to do that now easily. You know what I mean? Like we use Breezeway, I love Breezeway. We use their Breezeway Assist and it's been great, I have to say. They've been really wonderful. Virtual assistants obviously are wonderful. Again, having all the right trainings and processes in place is key though. But yeah, it's…

It's got its pros and cons, but overall, I think for the flexibility, the nice thing is when a guest leaves, you don't have to deal with them again. Yeah, that's true. Yeah. But in the other business, if you have a buyer who is just a total jerk and you got to keep dealing with them over and over and over, you can't really get away from them. You need them. Whereas you do have a little more flexibility to choose who you want to work with in this business, which is nice.

Jasper Ribbers (23:13.354)
Well, they might come back.

Jasper Ribbers (23:33.322)
Right. That's true. I mean, yeah, if you have somebody that you don't want to host again, like you're not obligated to host anybody, right? In the end of the day. Obviously there are some complications with canceling bookings on Airbnb and whatnot, but in the end of the day, you are in control of who you host, I guess, right? Is hospitality something that you always wanted to get into or did you kind of get into it by occasion?

Jayla Siciliano (23:41.102)

Jayla Siciliano (23:52.238)
Mm -hmm.

Jayla Siciliano (23:59.918)
Um, yeah, I mean, it was kind of by accident, but I will say I do love, um, the design side of things. Um, I've, I've done a few, um, I've designed a few STRs for other people at this point. So I've always loved, you know, aesthetics and design. My background previously was product development and design and footwear and bags. So I absolutely love that part of it. I love the, I really do enjoy hosting, you know, and, and the.

hospitality function of the business. We do welcome baskets and we go above and beyond with all these amenities. The idea of people just having this amazing time and being pleasantly surprised is really fun. I love that part of it. It's not too far away from what I ultimately love to do in that sense.

Jasper Ribbers (24:44.49)
Mm -hmm. Yeah.

Jasper Ribbers (24:53.642)
Right. And so your management company is called Atlas Vacation Rentals, right? Can you tell us a little bit more about the brand and who's your guest avatar and what kind of experiences are you providing?

Jayla Siciliano (25:07.854)
Yeah, so I would say mostly our guest avatar are families, you know, looking to either we have a lot of people from LA coming up to wine country or coming to Santa Barbara. And in Vermont, it's mostly people from New York and Boston, you know, going up to ski for the weekend or be in Vermont for the summer. So the properties, you know, that do the best for us are the ones that have.

amenities where the whole family can hang on the property, friends and family can hang there and be entertained on property, or just a few minutes away, go out to dinner, you know, go adventure and have stuff around the property close by that they can access easily. And, you know, we do, again, the best performing properties.

In Vermont, we put snowshoes and cross -country skis and all these things where they can really have this Vermont experience, these little add -ons that don't cost the owners a lot of money, or us a lot of money, but they just kind of help fill out that experience. And I think when people are trying to decide between two properties, if they see one that has like all these little bells and whistles and one that doesn't, and the prices are the same, it's easy to lean towards the one that does. So.

Jasper Ribbers (26:19.786)
If somebody comes up to you and this probably happens actually and asks you like, hey, you know, that's short -term rental business that you have that sounds really interesting. I want to get involved in this as well. Right. What would be, what would be your number one piece of like advice for that person?

Jayla Siciliano (26:36.622)
join multiple masterminds. So I don't have a mastermind, so I'm not even promoting my own mastermind or anything like that. I have joined two or three different masterminds when I was starting this off. And it would have been a much slower and more painful process. I don't know if I actually would have really built this up the way I did.

It's just, you know, it's very foreign, all these little things you need to do and all the systems and all the tech and everything. There's, I don't know, it just…

It's worth every dime to join a mastermind and have that community and have those resources and group that you can just go and ask questions when things pop up. I think in this business too, there's a million one -off situations. There's all this gray area and guest issues or stuff pops up all the time. And to have a community where you can just go and ask questions of how to deal some, get advice on how to deal with something is super helpful.

Jasper Ribbers (27:37.226)
Yeah. Yeah. And I think, you know, when I got started with Airbnb, it was in 2012 back then there were no masterminds. So there was nothing really, but it was also like so much easier to make money. Right. Cause it was literally like you throw something on the Airbnb and the phone will go ping, ping, ping, ping. And like, you know what I mean? So I think, yeah, and this in the current climate it's yeah. If somebody is going to start from scratch without any education or any support.

from communities. Yeah, it's pretty hard with the support of the communities, right? Let alone if you're trying to figure everything out yourself.

Jayla Siciliano (28:16.75)
Yep, agree.

Jasper Ribbers (28:18.314)
Um, do you have any, any funny stories to share from, from your experience renting out these, these homes? Anything crazy, crazy happen?

Jayla Siciliano (28:27.758)
Oh boy, crazy. Well, you know, we use ring doorbells, I guess the funniest ring doorbell.

one was this was when I only had like two properties. So I was actually paying attention to the ring doorbell, you know, occasionally. And I don't know, I can't remember exactly what happened, but for some reason I checked it and I saw there were a bunch of cars in the driveway. And I was like, Whoa, there's not supposed to be that many cars in the driveway. And then I looked again, like 10 minutes later, and there's a whole mariachi band standing at the front door with like a PA system and you know, microphones and all this stuff.

waiting to go in and it was a family who was in town for a wedding and they were throwing a party the day after the wedding. And you know, but we were like, oh my gosh, what should we do? You know, neighbors, blah, blah, blah. And so we were all worried that they were throwing this raging party. We couldn't get ahold of the guests. This is, you know, again, this is one of the ones that was an hour away from us that we own. So my husband drove up there because we were just like, we can't, you know, there's a

band, Mariachi band standing there. And so he knocks on the door and opens the door and it's like a bunch of grandmas dancing, you know, super innocent, like family party, but still we were like, we're so sorry. We just can't have a band in the backyard. You know, we actually felt really bad breaking it up, but we were like, sorry, you know, and they were nice about it and it worked out, but that was probably one of the funniest ones where it was just like, ah, you know. And then we've had a, we've had our share of just, you know,

Jasper Ribbers (30:01.066)

Jayla Siciliano (30:04.942)
what on earth is going on while people are there. I have no idea those situations. But my motto is just fix it and move on. It is so not worth getting emotionally worked up over any of it. You just fix it and move on. It's so random at times and it's just not even worth wasting an ounce of energy stressing about it.

Jasper Ribbers (30:16.714)

Jasper Ribbers (30:27.114)
Yep. I think we've all learned that through the experiences. I'd love to talk a little bit about your podcast, right? So Seed Money podcast. What's the podcast about?

Jayla Siciliano (30:41.326)
Yeah, so the podcast is really about that early stage entrepreneur who maybe has an idea or they've already invested some of their own money. They've got a little bit of traction or you know, they've gotten customer feedback and now they're going I really need to go get other people's money to take this, you know, to market or really make it a real business. And

I just love that stage of entrepreneurship. When people have ideas, there's so much passion that has to go into a company at that stage. When you're ready to go out and take someone else's money to make your, grow your idea, you have to be so passionate and so all in and excited. And I just love that stage. And it's also so hard to know what to do. And, you know, I think it's a lot of the content out there is from the VC perspective or.

the small percentage of entrepreneurs who exited for a gazillion dollars. And while I think all of that is super, super important and valuable experience, obviously, and those people are amazing, I think there's a bit of a gap in content around that more just early stage human side of the mental process of what you're going through to raise that first round of funding.

some of the tactics that you wanna use. It's very different than when you're going for an institutional round down the road. And now there are some VCs doing seed funding. There's all kinds of dynamics, but I just love that stage. And somebody asked me about a year ago, like what would my perfect day look like? And I said, well, I would spend time with my family.

I would exercise every day and I would basically talk to entrepreneurs all day about startups. That was like my, if money were no object, if, you know, blah, blah, that's what I would do all day. And then I kind of had this realization. I was like, well, I can do that now. You know, why, why am I waiting? I've got my short -term rental business functioning really smoothly.

Jayla Siciliano (32:43.406)
And, you know, it's not taking me a gazillion hours. I probably spend, you know, 15 hours a week on it. And so I went all, you know, dove head first into trying to figure out like how to do a podcast and ended up hiring a company to basically produce it. I was like, I don't want to burn myself out trying to do a podcast now. So I want to set it up so I can do this ongoing. I have no idea what to expect from it. I've committed to it for two years and.

We'll see what doors it opens. And it's just so much fun. I'm loving it already. I'm interviewing other entrepreneurs who've gone through this early stage and talking about my experiences and stuff. So it's really, really fun. I'm excited.

Jasper Ribbers (33:15.21)

Jasper Ribbers (33:23.978)
Yeah. Now I can relate to that because that's, that's kind of like how I got into this podcast too of like, Hey, no one's really talking about this Airbnb thing. I love talking about it. So let's interview some hosts and publish it. And then, yeah, 10 years later, it's, uh, it's become something much bigger than I thought it would. So, um, yeah, that's amazing. Well, actually, when it comes to raising seed, right? Cause this is actually like our, our

Jayla Siciliano (33:41.134)

There you go. That was so cool.

Jasper Ribbers (33:52.522)
company that I founded with my business partner, Eric Freewild. That's something that we talk about a lot. It's like, should we try and raise some seed money? Does that make sense? Or do we just generate, do we just like add some new revenue streams so that we can just support ourselves through those other revenue streams while we're building this business? What you call bootstrapping, right? How do you make, can you give any…

advice on like, how do we make a decision? Like what's the, what's the better route to take? Cause we're all, we're always like jumping back and forth on the, between those two options.

Jayla Siciliano (34:25.742)
Yeah, and I think it's smart to think through it because it's two very different routes and each have very different challenges and obligations, right? Once you do raise money, you're setting yourself on a path that is hard to reverse. You know what I mean? Now you have investors. So I just talked to some friends who are in the same situation last week about this.

And they were talking about going out and raising money. And I said, well, what's your end goal? Do you want to sell it? And they were like, oh, we haven't really talked about that. And so I was like, first thing is really figure out what that end goal is. And if you guys are aligned and the end goal is to say to sell it or to be able to hire a CEO earlier, so you're just an owner and not necessarily an operator.

If those are your goals, or you just have this passion to grow it bigger, to impact, have an insanely positive impact on as many people as possible, that end goal is so important because that's what the investor's gonna wanna know, right? And that will also help you decide if you need that money. If you're like, no, we just wanna kind of…

pull profit from it and just have an owner's draw and we'll do that for the next 10 years and we're cool with that, then you probably don't need to go raise money. But if you have that bigger goal, you're gonna have to have an exit of some sort in mind for that investor. Or if we reach this milestone, are we profitable enough to then repay them? But ultimately, typically they're…

investors are going to want to see some sort of exit. So that would be my recommendation is, you know, really hash out what that end goal is. And that should help you kind of decide if you know if that's the right route or not.

Jasper Ribbers (36:13.418)
Mm -hmm.

Jasper Ribbers (36:25.002)
I think it was like one of the seven habits of most effective people or something that book where I think that's one of them, uh, have a, have an end in mind, right? With everything you do have, have an end in mind. Um, so it's just, uh, yeah, that's a, that's good advice. Um, and then, you know, you talked about there's, there's raising money from the VCs, right? The institutional side, but then most companies, most entrepreneurs will start with like a small friends and friends and family round, right?

Jayla Siciliano (36:34.606)
Mm -hmm.

Jayla Siciliano (36:54.606)
Mm -hmm. Yep.

Jasper Ribbers (36:55.306)
If somebody was thinking of doing that, what would be some first steps or some basic one -on -one type of knowledge that they would need?

Jayla Siciliano (37:06.894)
Yeah, so I think first thing you want to do, there's two really simple ways to raise a friends and family round or a seed round from angel investors, convertible notes, and then what's called a safe note. And the benefit with both of those is you don't have to determine evaluation upfront. The paperwork is very simple. It's much more simple than a full on equity round.

And so it's going to cost you less money from an attorney perspective. So talk to an attorney, step one. You know, you need to kind of incorporate or have your entity structure in place and then basically ask them about, you know, convertible note paperwork or a safe note. And then you can basically take that, what your terms are, you know, hey, we're trying to raise a total of a million dollars. We're going to do a minimum of, you know, $25 ,000 each.

or if it's a hundred thousand dollars, a minimum of $5 ,000 each. And then, you know, basically have a pitch deck, you know, even if it's just a very simple one of, I always recommend doing a business plan, even if you don't ever show it to anybody, it's going to give you the background to be confident, to talk to investors about, you know, what you need and what you're doing. And then basically just getting it in front of people. And, you know, the best way to do it is just say, Hey, I'm going to start.

you know, raising money, would you mind just listening to my pitch and just start practicing it? And then networking your ass off because you just never know like, you know, I raised that initial almost half a million and they were from non friends and family investors I had never met many of them I met through, you know, six different connections, someone introduced me someone introduced me someone through and so on. So yeah, I think it's it's really figuring out.

What your terms are going to be what your structure is going to be which convertible notes are a great way or safe note and then from there You know have your ducks in a row your materials make them as professional as possible and then just start talking to people so Make sure you get enough money a long enough runway. That's one thing I think is you know Just really make sure you might not want to raise more money or you might you know It you might

Jasper Ribbers (39:17.546)

Jayla Siciliano (39:29.838)
What am I trying to say? Basically, you don't want to have to raise more money six months later. You know what I mean? So give yourself enough wiggle room that you've got a chunk of money to work with for at least a year.

Jasper Ribbers (39:41.642)
Yeah. Cause then the next step will be to raise like a real round with evaluation and like, you know, giving you an equity and stuff. Cause the first, the first seed round is you don't determine a certain amount of equity, right? You just say like, you're going to, when we raise the next round, you're going to get a discount on that race, but right. So you don't really determine evaluation or equity or anything that, which makes it so attractive to, to do it this way. Right.

Jayla Siciliano (40:06.702)
Yeah, so let's say right now the convertible note paperwork would say, you know, sometimes an investor might ask for interest on it. So they're going to accrue interest on say that hundred thousand dollars a year from now, when you go to raise that next round and you do it as an equity round. And let's just say the share price is determined at a dollar. Their hundred thousand might convert over at say 80 cents, you know, compared to a dollar. So they're getting a 20 % discount. So yeah, that's the incentive and motivation.

for them to kind of come on as an early investor, they're getting a little bit of a better deal.

Jasper Ribbers (40:37.802)
Yeah. And then I guess if, if we're not able to do that next round and we just burn through the cash, it's we're at the end of the runway, then we don't, we don't owe anything to those investors. Correct.

Jayla Siciliano (40:52.046)
Yeah, you definitely make sure you set it up that way. So sometimes convertible notes can be due and payable. So you want to make sure you set it up that, you know, and that's where you want to talk to a good attorney and ask them what is the worst case scenario? How am I protected? I have a, that is one thing I did correctly was set up all my paperwork and structure correctly. I have a lot of friends who got sued when they ended up having to pivot out of their companies, losing houses, stuff like that is not.

fun, right? So yeah, talk to an attorney and just say, what is the worst case scenario? How can I protect myself? Don't personally guarantee, you know, stuff. So definitely doable to set it up, you know, the right way, but you just want to make sure you talk to a good attorney for sure.

Jasper Ribbers (41:21.802)
Ooh, that sounds scary.

Jasper Ribbers (41:37.578)
Yeah. Yeah. It makes sense. Um, awesome. I have one, one last question that, uh, just kind of popped up as we, uh, as we were having these conversations, like going back to that original company that you founded the, the wine company, right? I'm just curious, like, what's, what's the sort of the mental journey when you decide to step away from it? Cause like, you know, people have invested in it and like, how does that? Yeah. How is that?

Jayla Siciliano (41:51.886)
Mm -hmm.

Jasper Ribbers (42:06.346)
mental, emotional process from walking away from it.

Jayla Siciliano (42:09.934)
Not fun, no. Ultimately, I think it really takes some very, very deep reflection on what do I want my life to be about? At the end of the road, I always think this way. If I am not here in five years, how do I want to spend the next five years of my life, the next year? We have no idea. It really can be over in a moment. And…

I think it really came back for me to living a life without regret. I have no regrets in trying things. I'm so glad. I've always gone for it and given it a shot. And I don't think I'll ever regret that. But if I stayed in something that I was just miserable in and wasted years.

and I come to that point, you know, at the end of my life, whenever that is, that I feel like I would regret or, you know, if I again, I have my son now, I love spending time with him, like, I'm not trying to grow this huge company right now. That's not my priority, my priority, he's only going to be little and want to spend time with me for so long. So my priority is really spending time with him. So I think it's really digging deep to what is important to you and then being, you know,

Honestly, just having the kind of balls to go for that, you know, and no matter what anybody thinks of you, I mean, the first time when I quit my job to start the wine company, my friends and family thought I was absolutely nuts. You know, they're like, you have an amazing job working for Burton snowboards. What are you doing? You have the dream job. Why are you doing this to yourself?

They thought I was nuts. And then when I stopped and decided to pivot out of the wine company, people were like, what are you doing? You got to deal with Mark Cuban. You're crazy. Why are you doing this? Keep going, keep going. But everything in my soul was telling me to not kill myself going down that path. So I think it just really takes digging deep and figuring out what is important to you, what are your values. And

Jayla Siciliano (44:17.966)
and then just having the courage to kind of act on it despite what anybody else thinks, which is not always easy as we all know, right?

Jasper Ribbers (44:25.162)
No, it's definitely not easy. It makes sense on a logical level, but to actually like practice it is a whole different story, right?

Jayla Siciliano (44:28.846)

Jayla Siciliano (44:32.622)
But doable, for sure.

Jasper Ribbers (44:34.858)
Um, awesome. Well, I want to thank you for, for joining us today. It's been absolutely amazing. Um, the, everything that you shared, uh, very interesting before we wrap up, um, you want to tell people where they can find your businesses, your podcasts, um, you know, any, any, anything you want to share or.

Jayla Siciliano (44:56.59)
Yeah, absolutely. So the management company is atlas -vacations .com. And then would love to have people check out the Seed Money podcast, obviously seed, if you just search Seed Money in any podcast app or seedmanypodcast .com. And then I'm on Instagram, jlissisliano. I'm not, you know, I don't do tons and tons on there, but love connecting with people.

So yeah, I would love to hear from people if anybody has any questions about the seed money side of things. I love chatting about that stuff, so it's fun.

Jasper Ribbers (45:27.658)
Awesome. Well, thanks for joining today and to the listeners. Hope you enjoyed this episode. And of course we will be back soon with a new one. See you then.


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