226. What Does Success Really Mean To You? w/ Jayla Siciliano

Entrepreneur Jayla Siciliano shares her journey from Shark Tank to real estate success, offering insights on pivoting careers, raising capital, and aligning business with personal goals.

• Growing up with an entrepreneurial father who owned a land surveying company
• Developing a sense of adventure and love for trying new things
• Working at Burton Snowboards for seven years in product management
• Launching Bon Affair wine company in 2008 during recession
• Pitching on Shark Tank and securing a deal with Mark Cuban
• Learning that growing too fast without resources leads to burnout
• Transitioning to real estate investment during COVID-19
• Building a property management company with 30+ luxury rentals
• Starting the Seed Money Podcast to help entrepreneurs raise capital
• Understanding when to bootstrap versus when to seek outside funding
• Finding the courage to carve your own unique path to success

Connect with Jayla on LinkedIn or check out the Seed Money podcast on all major podcast platforms.

Chapters

• 0:00 Introduction to Entrepreneur Jayla Siciliano
• 1:41 Growing Up with Entrepreneurial Roots
• 3:55 Developing a Sense of Adventure
• 6:08 Early Entrepreneurial Ventures & Burton Career
• 9:03 Launching Bon Affair During Recession
• 15:43 The Shark Tank Experience
• 23:06 Transitioning to Real Estate Investing
• 28:02 The Seed Money Podcast Mission
• 31:21 Bootstrapping vs Raising Capital
• 35:47 Carving Your Own Path: Final Wisdom

Transcript

Speaker 1: 0:00

Yeah, it's Mindset Cafe. We all about that mindset. Gotta stay focused. Now go settle for the last. It's all in your head how you think you manifest. So get ready to rise, cause we about to be the best. Gotta switch it up. Gotta break the old habits. Get your mind right. Turn your dreams into habits. No negative vibes, only positive thoughts.

Speaker 1: 0:20

What is up, guys? Welcome to another episode of the Mindset Cafe podcast. It's your boy, devin, and today we got a special guest on. We got Jayla Siciliano. I saved myself on that one. I told her I was going to get tongue tied a little bit on it, but I'm excited to dive in. The one thing that stuck out to me when I was looking into her background is she's a Shark Take alumni, right. But also there's some cool things that she has her own podcast that we're going to dive into. She is a real estate investor, she is a CEO and, honestly, she's just a well rounded entrepreneur. So we're going to dive into all of that. But again, her podcast is the Seed Money Podcast. So make sure you guys check that out. But without further ado. Jayla, thanks so much for taking the time out of your day to hop on the Mindset Cafe.

Speaker 2: 1:11

Yeah, thanks for having me. Great to be here. This is fun to connect.

Speaker 1: 1:15

Definitely, and so I want to dive. I like to rewind, you know, right out the gate, and before we dive into all of your accolades and all your ventures, what was your bring up like right? Because this is what connects people and kind of lets it resonate. You know where you're currently at to. You know where you started from. So what was your childhood like? What did your parents do? What was that backstory like?

Speaker 2: 1:41

Yeah, so I grew up in a small town in New Hampshire and my dad had his own business a small business land surveying company. My mom just basically was stay at home mom and did his bookkeeping and worked for him here and there, and so I grew up seeing my parents were home all the time, flexibility, plenty of time to take vacations and do stuff like that. But I also kind of on the flip side of that grew up with, you know, my dad being one of those entrepreneurs who kind of did everything himself. So I've had to make some. So it instilled a lot of great, you know, mindset from a. You can have flexibility, you can be passionate about what you do, love what you do, be successful. But I also had to shift some of that you know, do it, do everything yourself kind of mindset. That was also instilled in me.

Speaker 2: 2:40

So, yeah, small town and day after graduation I could not wait to get out of there. I moved to Long Island and then I moved all around after that. But yeah, overall had a really, you know, very thankful. I grew up in a great place little lake and a ski resort. I love the outdoors because of that. But I live in Santa Barbara now, and you couldn't pay me enough money to move back to the winter, so Santa Barbara is beautiful too.

Speaker 1: 3:08

I mean, I'm in LA, it's a little more city out here, but I believe me, I've been to Santa Barbara so many times and I love it out there it is beautiful. So I mean, with with you moving around where you graduated and you started moving around, what was that like? Cause I mean, each place you're moving to, you're essentially looking for new work, you know, and so forth. So what was that mindset Like? Why did you want to kind of move around and kind of venture all the way out to Santa Barbara?

Speaker 2: 3:35

Yeah, that's a great question, I think you know. Looking back, I think I I definitely love new things. I really do have a deep sense of adventure. I'm actually not sure where that came from. It's not like I traveled all around the world as a kid or anything, but I just get antsy, would get antsy and be like want to go somewhere else and there's so much more to do and so much more to see and why not just try another place.

Speaker 2: 4:05

So that kind of came out by moving around and then I think later it came out and starting, you know, career shifts and business shifts and stuff like that. But I think it really was just rooted in like this excitement to try new things and always be on a new adventure. And I I still a little bit like we're leaving for Belize in three days. I absolutely can't wait. I have a thing where I try to travel to a new country, at least one new country every year. I just love traveling and so I think. But ultimately I think it was kind of that, you know, looking for something new and exciting.

Speaker 1: 4:42

Oh, I mean that's awesome, though, because getting to see the world and even just around the country and I was talking to someone about this because I mean born and raised in LA and until becoming an entrepreneur and joining Business Masterminds and us, doing quarterly meetups and all that kind of stuff and traveling to other states there's a different way of life, even within the United States, that you don't realize unless you actually visit, right Cause I mean you think I'm being born and raised in LA. You think everything is like fast paced, you know hustle and bustle and all that kind of stuff. And you go to Montana and all of a sudden we're at a restaurant and I was like, all right, come on. Like let's like I've got things to do, like but it's.

Speaker 1: 5:26

And then, but it's like in the movies where you know the the waitress is walking around and introducing herself to each person and have a conversation with each person, and I'm like like, oh my goodness, like come on, like this is, this is taking forever. But then at the same time you realize that maybe you should just slow down and, and you know, kind of appreciate the day, right. So I think that's so awesome with, like you traveling and everything, because you get to see different cultures, you get to see different ways of life and it really opens up your eyes to be able to walk in someone else's shoes. So, speaking of walking in someone else's shoes and living a life that is not necessarily for everyone, because it's not the easiest path, what was your intro to entrepreneurship?

Speaker 2: 6:08

Well, you know, it's funny, Even my high school project was I had this, you know, vision of designing my own clothing brand and I really wanted to do that and I learned how to sew. And then, even in college and right after college, I had a little art studio and I was making, you know, leather handbags and doing trunk shows. So I think I kind of had this, just didn't even call it entrepreneurship, it was a hobby, but it was this desire to like create things on the side. And then I did. I had seven years of a corporate job, which was great, super fun.

Speaker 2: 6:48

Some would call the dream job of working at Burton Snowboards and getting 60 days on the mountain and traveling to Asia and working with the team riders Super fun job. But it wasn't enough, which is crazy, and I just was like I don't know, I have this idea and I can totally do it. Why can't I? You know why not? And so quit my job and people thought I was crazy. But that was the first real jump into entrepreneurship, which was a slightly, you know, rude awakening a few months later when it was like oh, whoa, what did I do? But yeah, so that was that, and even, you know, actually right after college too. I did a business plan course women's economic ventures here in Santa Barbara. I went through their program so I definitely had this like desire to be an entrepreneur before I actually took that leap, you know, after Burton.

Speaker 1: 7:42

So what was that first entrepreneurial venture? Was that the Bon Affair?

Speaker 2: 7:46

Yeah, so that was my wine company and I did that for 9, 10 years, yep.

Speaker 1: 7:50

And so with that, unless I'm mistaken, you started that during the 08 recession.

Speaker 2: 7:57

Yep, I quit my job at the end of 07, right before the market crashed and you know, thinking everything's great and then all of a sudden I had. You know I have no job, that we're in a recession and I am. I've told my whole friends and family that I'm going to start this company and now it's like sheer determination I have to make this happen. But I had a lot of things working against me for sure.

Speaker 1: 8:24

Yeah, so what was the confidence I mean not even the confidence what was the mindset that you had to adapt or develop to essentially become an entrepreneur, and especially in such a crazy time, that really allowed you to grow into the person that you are today?

Speaker 2: 8:45

Yeah, I think it's. You know I lived by the words patience and persistence. I kind of had this awareness that, like I don't, I don't know what I don't know, I don't know everything. I know that I have a lot I need to figure out, but I do think that my that seven years I spent in product management and product development. The whole seven years I was just spending figuring things out. You know, how do we make this? How do we get this to cost less? How do we make this more sustainable? Like, how do we find a new factory?

Speaker 2: 9:24

So I had spent seven years basically learning how to figure things out. And then I just applied that to, you know, a business venture. And I think that's one of the biggest things. If you can just learn how to figure things out and it's interesting I kind of think that that's just something everybody knows how to do. But I've learned since that it's not, and it can be a skill that's learned, or some people just have more of an inclination to do that on their own. But if you can just approach things with a I'm going to just do whatever it takes to figure it out. It's amazing how much you can accomplish. You know, it's crazy.

Speaker 1: 10:08

No, that is true, right, I mean, there's a solution to every problem, but it's just your willingness to find that solution and have persistence and patience too, because, again, solution number one might not be the real solution, right, so it takes a little bit of time, but how? So? You said you were in that for 70 years. Did you sell the company? Did you close the company?

Speaker 2: 10:26

So yeah, the wine company I did for nine to 10 years and I long story leading up to kind of how I pivoted out of it, but I ended up just closing it down. It was the hardest decision I've ever made in my life and I could look at it, you know. I realize now like it. One, you know, frame of reference is that I quit and gave up on that company. But how I truly see it is that I actually opened myself up to a completely different life, started a family my husband and I had put off having kids.

Speaker 2: 11:01

I'd put my entire personal life except for gay married on hold to run that company and got extremely burnt out and realized the dream wasn't the dream anymore and it was a really hard decision. I had my investor's support, though that I just that wasn't the vision that I started with and that wasn't what I wanted. And it was a huge pivot to really get what I truly want in life, which is, you know, business ventures, flexibility, time with my family, financial freedom. Those are the things I truly care about, not like this ego drive of growing this huge company. That just wasn't cutting it for me anymore, I guess.

Speaker 1: 11:46

No, I mean, it makes sense. I mean we all have those pivots and there's, no, there's no correct pivot, you know, in life it's whatever fits you or fulfills you in the moment, as well as maybe that next phase or that next chapter of your life, right, going from Burton to being an entrepreneur, right, and so what was the next chapter? You know, you said you put your life on hold, but what was the next career chapter in your life?

Speaker 2: 12:12

said you put your life on hold. But what was the next career chapter in your life? Yeah, so I took a year. I was pregnant and basically I had gone out to raise another round of funding and I was like sick as a dog. And that's when I was just like you know what I just. This is so not the top priority anymore. So I took a year off spent with my son newborn. That was a whole nother like whoa.

Speaker 2: 12:29

This is not easy either. I don't want to be a stay at home mom, that's for sure. I love him to death, but I love working and I don't want to not work. So I. But I also was like I don't ever want to have my own company again. I will be totally happy just collecting a paycheck. I don't need to have my own business. But in the back of my head and I did say out loud to my husband a few times but if I ever do start another business, it'll be a service-based company. I'm not doing consumer products again. So I ended up just getting a job as a VP of sales and marketing with a music company here in Santa Barbara. I did that for five years and then I realized I overcorrected. I was like I don't want to work for someone else. So I was like, okay, this isn't sustainable either. I need way more flexibility. It was fun, but I just realized I didn't have to work for someone else.

Speaker 1: 13:33

I had a lot of skills that I could put to use and work for myself. So I mean going from being a being the boss and having that flexibility to having a boss is definitely not an easy transition, you know, and unless you disagree.

Speaker 2: 13:43

Well, I think for certain people it's not.

Speaker 2: 13:46

I think for me the reason it worked is because I had so much respect and appreciation for what it is like in that CEO founder role that I didn't butt heads with them because I saw my job as supporting their vision. Right, it wasn't my company, I wasn't responsible for payroll, I didn't have the luxury to call those shots of what the vision and direction should be. So in some ways I think I was like a great employee because I fully respected how hard it is to be in that CEO you know founder role and I saw my role as VP of sales and marketing to ultimately support their vision and then execute it. But I do think some people get in there and they, you know it can be a different situation where they feel like they know better or they have their own way of wanting to do it. But unless you are in that CEO founder role like you, just you know that is the benefit that they get for putting in all those painful, long hours and taking those risks and all of that.

Speaker 1: 14:53

So no, definitely. I mean, yeah, that makes sense. And sometimes an entrepreneur, transitioning, is a great entrepreneur, right, Because you have the creativity, you know how to build, but you don't have to have as much of the stress. But there comes, you know, some give and take with that. You know, if you're a creative, creative type and you want to do it a certain way, it's like sometimes you gotta, you know, know that you can't go that way If the person above you is telling you, hey, that's not what we want to do, Right, so there's there's there's pros and cons, but again, it just whatever pivot works best for you at the time. I do, before we get too far away from it was Bonifera. Was that the company that you were on Shark Tank with?

Speaker 2: 15:43

Yeah, yep, so that was the one I was on Shark Tank with and quickly, what led up to Shark Tank? So I started that venture. It was 2008. I ran through credit cards, 401k, all of that, realized I needed to go out and raise money. Went back to school for my MBA, thinking I really need like to network, and then masterminds weren't as common or prevalent as they are now. So the MBA was kind of a very expensive way to network, but it took me. So I started pitching investors. It took me 18 months of nonstop pitching hundreds of investors to raise the first half million from non-friends and family. I did a friends and family round and then I raised a half million in convertible notes from non-friends and family and that was enough to get us started.

Speaker 2: 16:30

The total raise was going to be 2 million, but we got the first tranche of 500,000 and went to do our first production run and we lost a hundred thousand dollars worth of inventory. It was devastating. There was only one bottler that would take us on because of all these licensing requirements Then. A lot of those are not issues now, but they were out of business six months later. So devastating place to be where you've put your heart and soul into. Investors have put their trust in you and then you lose $100,000 and you have no inventory. So basically we had to put a ton of money into licensing, legal all that. We launched a direct to consumer website. So basically we were going to run out of money a lot sooner, weren't hitting the milestones we needed to hit to get that next one and a half million.

Speaker 2: 17:22

So I was like, you know, this is, this is not good. We're potentially going to end up doing a down round if I, you know, raise more money and I can't get the valuation up. So I had an advisor who kept saying you should go on Shark Tank, you should go on Shark Tank. And I was like, oh, I don't want to go on that show. And then I was going to meet him for lunch one day and I was like I have to just apply before I go meet with him so I can just tell him I did it and he can stop bugging me.

Speaker 2: 17:52

So I applied for the show and then, you know, a few months later and got a call and I was like, oh my God, now I actually have to like, do this. So jumped through all the hoops and you know they said I'd been accepted to the show and I practiced like crazy, you know, to be um to get on there. I list, I watched every episode, I wrote down all the investor questions and I got up there and it was all ready to pitch. I'm in the dressing room and the producers came in and they said we're so sorry, you're not going to get to pitch today. We don't know if you'll get another shot. I was like devastated. I'm like, oh my God, I just want to like get it out at this point.

Speaker 2: 18:28

So I went home and then a few days later I got a call and they said you know, there's a 50-50 chance you'll get to pitch tomorrow. Do you want to come up? And I was like kind of going into it like this is I'm so thankful for the opportunity. This is like just a cool life experience. I'm going to try to just enjoy it as much as I can. And I went out there and it's it's pretty brutal. They're all firing questions at the same time. You know, trying to throw you off.

Speaker 2: 18:58

I was in there for about an hour and they edited it down to 10 minutes but ended up getting the deal with Mark Cuban, which was amazing and super cool, like such a great guy. I can't say enough good things about him. He was like, actually involved, had contact with him. He had a whole team of people that supported us. But what happened is, you know, we went from. You go from where you're kind of just begging distributors, begging retailers to take your product when nobody knows about you, and then you get all this exposure and it's just a shot in the arm and now everyone's coming to you and it's so hard to say no, right, because you've just been like so you want to take advantage of all these opportunities.

Speaker 2: 19:39

So the big, big lesson learned was growing too fast without the right resources is recipe for burnout and very, very challenging. Mark was financing inventory runs for us but he just doesn't do further equity investments. It's kind of his rule of thumb. So I ended up. It's very challenging in alcohol to be profitable and this was kind of carving out a new category. This was before White Claw came out.

Speaker 2: 20:07

It was like an all natural, healthier, lighter wine spritzer no preservatives, no sugar and distributors are like why would anybody want this? Why? So it was a very expensive thing as a small brand to try to educate an industry and an end consumer on a new product category. So there was a lot of factors involved like market timing, lack of resources, trying to go too far too fast. I think if I had launched it five years later, as the category had started to already, you know, be carved out, it could have been a different story, because now it's like an $11 billion category. Now you go into Whole Foods, there's a whole section of these like lighter, you know, alcohol options. So anyway, yeah, that was the Shark Tank story, but again, can't say enough good things about the show and you know Mark Cuban's amazing. So it was a fun experience.

Speaker 1: 21:01

How I mean, I do want to like. Like talking to your peers and pitching your peers is one thing right, and it could already be get. You can get nerve wracked, you know, just stepping on stage in front of your peers, your colleagues, let alone like just an audience. But when you're in front of such like high profile individuals, you know, on the show, what was that like? Did you know that feeling right when you actually saw them all you know, lined up ready to basically shark attack you?

Speaker 2: 21:29

Uh well, I think you kind of like blackout a little bit, because it's a blur. I don't really remember all of it for sure. Um, I think that's why anybody who's gone on the show that I've coached afterwards. It's like you have got to practice and be so dialed. It's so different than any other pitch Because you can't rely, yeah, the nerves just ramp up and the adrenaline and so you just have. It has to be like muscle memory at that point responding to questions and the pitch itself, because I remember the producers are like you know, we're going to hit record and even if you pee your pants, we're not going to stop recording. So anything spare game once we hit record, you know. So you're like it is definitely high pressure, but I don't know it was fun. Somehow I got, I did a great job and, you know, got a good edit and pulled it off. But I put a lot of time and effort into practicing and prepping.

Speaker 1: 22:28

Well, I mean, that's preparation is key, right, so that's that's awesome. But while watching the show and knowing that you know, you said it's, you know like an hour long of of Q&A and back and forth, it's like, man, it just seems like it is five, 10 minutes, and so I can't even imagine that pressure. So that's a win just in your life book of being able to do that.

Speaker 1: 22:51

Yeah it's fun. So I mean, now you've transitioned from the Bonifera and you transitioned from being an entrepreneur. Was the next step your real estate, your rentals, or was there something in between those?

Speaker 2: 23:06

Yeah, no. So, um, when I had the, the job at the music company um, covid hit 2020 and we went to rent a place in Paso Robles for a week and it had a pool and I you know we're everybody was dying to get out of their house. We were cooped up with a toddler and I was crunching the numbers. I'm like, wow, these guys are killing it with what we're paying here and we're driving home and we're always looking at real estate. Anyway, I had bought a triplex in my early 20s. I fixed up each one, so I've always been in tune with real estate. My parents used to renovate houses and had rental units and stuff like that.

Speaker 2: 23:50

So after that trip, there was a property on the drive home. My son had to pee. We pull off on the side of the highway and I said to my husband I said there is a house right over there that's for sale, that has a pool. Can we go look at it in this little town, little wine country town? And so we drove by it and I went home and I crunched the numbers and the next day we put an offer in and we hired a management company because I was working and they were so horrible, I can't even tell you. The customer service, like everything was just so bad. They were renting it for super cheap and I was like this is not going to work and my husband's like you should do it, you should do it, and I'm like I don't have time to do it. And then finally I was like, okay, I'll do it. So I pulled the like wake up at 4am, set up all the software.

Speaker 2: 24:38

We knew we wanted to keep buying rental properties, buying rental properties. So I like set up the you know to be able to manage like 100 properties, went kind of overboard but started managing it myself and I was like, actually this is kind of fun. I like the hospitality side of it. I love creating a great experience for people. And I was like actually I could just do this and it kind of checks that it's a service based business. I love the real estate investing side and kind of going back a little bit even to that, always looking, you know, sense of adventure. The fun thing with real estate is there's always a new deal. There's always you can be looking for new deals. You know development projects, renovations, it's like there's always something new, but it's still within the same bubble. So I ended up quitting the job and started doing this full time and then got this pretty well set up to give myself a lot of time and flexibility and started the podcast. So that's kind of how that turned out.

Speaker 1: 25:40

Okay, so that was actually my next question, but before I ask that, so how many real estate properties or rental properties do you guys currently have?

Speaker 2: 25:49

now, if you don't mind me asking, yeah, so we own three and then I manage another 30.

Speaker 2: 25:57

And most of those are in Stowe, Vermont.

Speaker 2: 26:01

So 24 properties in Stowe, Vermont, 3,000 miles away, and the rest are here in Santa Barbara. And we bought a property in Vermont because we go back there every summer, Because, hence, growing up in New Hampshire, most of my family is in Vermont now and so the numbers just worked really well. There we saw this gorgeous place 18 acres. It had seven lots already pre-approved through the state to develop and we were like this is a great spot. So we bought that and then it just kind of word of mouth, started growing the rental side of it or the management side of it there and set up my team, you know, and it was definitely some growing pains at first because of time zones and you know again, learning a new business, it's not easy Again, you don't know what you don't know at the beginning, looking back, like I would have had things way more dialed in earlier in certain areas, you know, but you just kind of keep evolving and fine tuning until you get it in a good spot, which it is now so no, that's awesome.

Speaker 1: 27:08

So I mean, so the management company like that you're managing your three houses, but three homes, but you're also managing other people that are doing the same as well, right?

Speaker 2: 27:18

Yeah, so these are either just second homeowners, where they vacation there a couple times a year. They're all larger luxury properties and we just so we manage the whole property for them. We, our maintenance team, takes care of all the maintenance, our turnover team, guest relations, booking, marketing, all that stuff. So it's yeah, it's a service for homeowners who want to rent their house when they're not there.

Speaker 1: 27:48

Okay, I mean that's awesome. And then you said you started the podcast after this company was already started and it's the Seed Money Podcast, right? And so what was the idea behind starting the podcast and what was the purpose for the initial start?

Speaker 2: 28:02

Yeah, so I love the real estate stuff, but I don't really feel like I'm, you know, doing a lot to kind of help the world. You could say, and I I've had so many mentors over the years and so many people helped me in those 10 years of starting Bon Affair like just gave their time to help me learn how to raise money. You don't just know that stuff, I mean, you can read about it online but you really need people who've been through it to point out some of the things that can go wrong to help you avoid some of the common pitfalls. It's not an easy thing to do to go out and raise money and there is so much passion behind a person who has an idea and is committed to going out to get funding to launch their idea. You have to be so passionate about what you're doing and so excited and committed and dedicated and I just love that passion. I think it's so inspiring and it's just needed to make the world go round and we need more good entrepreneurs, and so it was kind of my way of giving back. I was like I love that early stage process.

Speaker 2: 29:18

My story isn't of raising millions and millions and millions of dollars, but it's raising money against all odds, like I had no revenue. I had no experience in the industry. It was in a recession. I'm female and a very male, especially then in 2008, even more so. So I feel like you know, I just have so much to give and I love talking about that stuff.

Speaker 2: 29:40

So I started the podcast as a way to just give back and help, and I'll review people's pitch decks. I've started taking on some one-on-one coaching clients who just they're so busy in their company They've got maybe a million in revenue. They've never raised money and they don't know how to put their pitch deck together to make it compelling. They put a gazillion words on a slide and it's like nobody's going to read all that. So I love I mean I could just do pitch decks all day. It's so, it's fun for me. I absolutely love doing it. So, um, so that's why I started the podcast and I just kind of do that. It's it's a passion project, but I would love to put more and more time into it, as you know. I don't know, in the next year or something, I'll figure out how to do that.

Speaker 1: 30:22

But no, I mean that's. It's such a niche area of business too, because you could be a great business owner and a great entrepreneur, but pitching and raising money, it's not. It's, it's a whole separate subcategory of business. And I mean we, for for my actual business, like you know, we do have an investor and even that one pitch, I mean that for for my actual business, like you know, we do have an investor and even that one pitch, I mean that was one of many, but that one, it was still again same thing with you Like there was no revenue, there was, there wasn't even a really a company. When, when I pitched it and it, I'm definitely not at the level you're at and so I know even the information you're giving out on that podcast is going to be huge in such so niche down on that. So I mean the one question I would ask is when? When should a startup decide to bootstrap it and figure it out or try to raise money and outside capital Is there? Is there a line?

Speaker 2: 31:24

I think I think it's different for everybody. And one thing I actually want to say before that the other reason I started it is because so much of the content out there on this topic are from this Silicon Valley go big or go home kind of VCs putting out content, and it's very much from the investor perspective and it doesn't cover that like human side of what you're going through when you're trying to raise money and the challenge, the mental challenge there, and so to how that applies to your question, is that I think there is this culture where people do feel like I need to grow a huge company. Well, it's not as much anymore. It used to be a lot worse like this, but there's still this culture of if I'm going to start a company, I need to grow it big or I need to get it to a certain dollar amount. Even a lot of the VCs now now they're looking more and more for companies that can reach profitability and be more sustainable. You know this like invest a ton of money into something and then just have it flop a year later is, I think, getting old right For everybody involved. So, in terms of like when to bootstrap versus when to raise money, I think there are certain companies that you can bootstrap and there are certain companies, like consumer products, where you just need inventory and you need marketing dollars and you don't always have that money, and so I think a lot of it comes down to what your risk threshold is right. So some people I mean some people like mortgage their house to put it into their company. I do not recommend doing that. So the one thing I never did I never personally guaranteed anything. I didn't get sued. I wasn't in debt when my company ended, so I went out, I put in what I was comfortable putting in and then I raised money after that and I raised it from non friends and family because I didn't want to put them at risk.

Speaker 2: 33:24

So I'd say you know you bootstrap until you, for the most important thing in the beginning is really setting a goal for your company that aligns with your personal goals, right. So if you are in your head going, I need to grow this to 20 million, like why, why do you want to grow this to 20 million? Like why, why do you want to grow that to 20 million? What's the real reason behind that? And if you still want to grow it to 20 million, then you probably need to go out to raise money. If you are growing it to just own your own company and have more money and flexibility that you don't necessarily need to grow it to 20 million and once you get investors involved, you're just working for them, right? You're not necessarily working for yourself as much anymore. Now you're on their trajectory. You have to hit certain milestones.

Speaker 2: 34:11

So I think there's a lot of factors to that question of bootstrapping versus, you know, raising money like the company I'm working with right now. They've been bootstrapping versus you know, raising money like the company I'm working with right now. They've been bootstrapping since they started in 2016. They were kind of successful in other areas before but you know, still not paying themselves and that's where it gets really exhausting.

Speaker 2: 34:36

So when you're at that tipping point of like we just need more money to get ahead and make this sustainable, you might need to go out and raise more money because typically bootstrapping, you know you're cash strapped. You're not paying yourself a market salary, most likely, and you can only do that for so long. Some people can do that, are in a situation that you can do that much longer. Other people, you know, know can't do it for as long, so I don't know if that was helpful at all, but I think there's just a lot of variables there and ultimately it comes down to like figuring out what your personal goals and then deciding you know how to incorporate your business goals with your personal goals and letting that be the foundation for the decision no, I think I mean that answered the question in detail.

Speaker 1: 35:23

That was, that was amazing, and so I like to ask you know, one final question, and this question is on Jayla's legacy wall. Right, you can leave any lasting message for the up and coming generations, right, short or long. But what is one message that you would leave that you've learned along your journey?

Speaker 2: 35:47

Hmm, I mean, I would just say it's like carve your own path, like don't worry about what other people are doing. I think it's very easy to compare yourself and feel like you're supposed to do this, you're supposed to do that. And it is the brave decision to not follow that and to just carve out your own path. Maybe your path zigzags, maybe it's not, you know, like your average thing, and that is totally okay. There's no right or wrong way to do it and you just have to, like, go after what works for you and just, I think, get really in tune with what it is that you want out of life. You know what is it? What are you? Again, those personal goals are so, so, so important and should be kind of your anchor for everything you do, and if you can be brave enough to do that, you can live a really fulfilling life.

Speaker 1: 36:38

So that's what I would say brave enough to do that, you can live a really fulfilling life. So that's what I would say. No, that's awesome. It is true, Not everyone's journey, even to the same or similar goal, is going to be the same right. Yours might zig and zag and mine might go just up and then take a huge left turn right, and so that is so awesome. Where can people connect with you and where can they find your podcast? At?

Speaker 2: 37:02

Yeah, so podcast is on all the podcast channels. Just search Seed Money Jayla and it'll pop up, and then LinkedIn is the best spot to connect with me. I'm pretty active on there.

Speaker 1: 37:14

Awesome. Well, guys, that will be in the show notes as well. If you're watching on YouTube, it'll be in the video description. Make sure you guys go check out her show. Make sure you guys check her out on LinkedIn. But I just want to say, you know, thank you so much for taking the time out of your day again to you know, hop on and drop so much knowledge of business and your experience of business in such a cool, you know, journey that you've been on.

Speaker 2: 37:36

Oh, you're so welcome that you've been on.

Speaker 1: 37:51

Oh, you're so welcome. It was fun, happy to connect. We'll connect soon.