June 30, 2025 • 38 mins
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.
Thanks for listening & being part of the Mindset Cafe Community.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
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 youthink you manifest.
So get ready to rise, cause weabout 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, onlypositive thoughts.
(00:20):
What is up, guys?
Welcome to another episode ofthe Mindset Cafe podcast.
It's your boy, devin, and todaywe got a special guest on.
We got Jayla Siciliano.
I saved myself on that one.
I told her I was going to gettongue tied a little bit on it,
but I'm excited to dive in.
The one thing that stuck out tome when I was looking into her
(00:45):
background is she's a Shark Takealumni, right.
But also there's some coolthings that she has her own
podcast that we're going to diveinto.
She is a real estate investor,she is a CEO and, honestly,
she's just a well roundedentrepreneur.
So we're going to dive into allof that.
But again, her podcast is theSeed Money Podcast.
So make sure you guys checkthat out.
(01:05):
But without further ado.
Jayla, thanks so much fortaking the time out of your day
to hop on the Mindset Cafe.
Speaker 2 (01:11):
Yeah, thanks for having me.
Great to be here.
This is fun to connect.
Speaker 1 (01:15):
Definitely, and so I want to dive.
I like to rewind, you know,right out the gate, and before
we dive into all of youraccolades and all your ventures,
what was your bring up likeright?
Because this is what connectspeople and kind of lets it
resonate.
You know where you're currentlyat to.
You know where you started from.
(01:35):
So what was your childhood like?
What did your parents do?
What was that backstory like?
Speaker 2 (01:41):
Yeah, so I grew up in a small town in New Hampshire
and my dad had his own businessa small business land surveying
company.
My mom just basically was stayat home mom and did his
bookkeeping and worked for himhere and there, and so I grew up
seeing my parents were home allthe time, flexibility, plenty
(02:03):
of time to take vacations and dostuff like that.
But I also kind of on the flipside of that grew up with, you
know, my dad being one of thoseentrepreneurs 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.
(02:24):
You can have flexibility, youcan be passionate about what you
do, love what you do, besuccessful.
But I also had to shift some ofthat you know, do it, do
everything yourself kind ofmindset.
That was also instilled in me.
So, yeah, small town and dayafter graduation I could not
(02:44):
wait to get out of there.
I moved to Long Island and thenI moved all around after that.
But yeah, overall had a really,you know, very thankful.
I grew up in a great placelittle lake and a ski resort.
I love the outdoors because ofthat.
But I live in Santa Barbara now, and you couldn't pay me enough
money to move back to thewinter, so Santa Barbara is
(03:07):
beautiful too.
Speaker 1 (03:08):
I mean, I'm in LA, it's a little more city out here
, but I believe me, I've been toSanta Barbara so many times and
I love it out there it isbeautiful.
So I mean, with with you movingaround where you graduated and
you started moving around, whatwas that like?
Cause I mean, each place you'removing to, you're essentially
looking for new work, you know,and so forth.
So what was that mindset Like?
(03:28):
Why did you want to kind ofmove around and kind of venture
all the way out to Santa Barbara?
Speaker 2 (03:35):
Yeah, that's a great question, I think you know.
Looking back, I think I Idefinitely love new things.
I really do have a deep senseof adventure.
I'm actually not sure wherethat came from.
It's not like I traveled allaround the world as a kid or
anything, but I just get antsy,would get antsy and be like want
(03:57):
to go somewhere else andthere's so much more to do and
so much more to see and why notjust try another place.
So that kind of came out bymoving around and then I think
later it came out and starting,you know, career shifts and
business shifts and stuff likethat.
But I think it really was justrooted in like this excitement
(04:19):
to try new things and always beon a new adventure.
And I I still a little bit likewe're leaving for Belize in
three days.
I absolutely can't wait.
I have a thing where I try totravel to a new country, at
least one new country every year.
I just love traveling and so Ithink.
But ultimately I think it waskind of that, you know, looking
(04:39):
for something new and exciting.
Speaker 1 (04:42):
Oh, I mean that's awesome, though, because getting
to see the world and even justaround the country and I was
talking to someone about thisbecause I mean born and raised
in LA and until becoming anentrepreneur and joining
Business Masterminds and us,doing quarterly meetups and all
that kind of stuff and travelingto other states there's a
different way of life, evenwithin the United States, that
(05:04):
you don't realize unless youactually visit, right Cause I
mean you think I'm being bornand raised in LA.
You think everything is likefast paced, you know hustle and
bustle and all that kind ofstuff.
And you go to Montana and allof a sudden we're at a
restaurant and I was like, allright, come on.
Like let's like I've got thingsto do, like but it's.
(05:26):
And then, but it's like in themovies where you know the the
waitress is walking around andintroducing herself to each
person and have a conversationwith each person, and I'm like
like, oh my goodness, like comeon, like this is, this is taking
forever.
But then at the same time yourealize that maybe you should
just slow down and, and you know, kind of appreciate the day,
right.
So I think that's so awesomewith, like you traveling and
(05:46):
everything, because you get tosee different cultures, you get
to see different ways of lifeand it really opens up your eyes
to be able to walk in someoneelse's shoes.
So, speaking of walking insomeone else's shoes and living
a life that is not necessarilyfor everyone, because it's not
the easiest path, what was yourintro to entrepreneurship?
Speaker 2 (06:08):
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 reallywanted to do that and I learned
how to sew.
And then, even in college andright after college, I had a
little art studio and I wasmaking, you know, leather
handbags and doing trunk shows.
(06:29):
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 acorporate job, which was great,
super fun.
Some would call the dream job ofworking at Burton Snowboards
(06:51):
and getting 60 days on themountain and traveling to Asia
and working with the team ridersSuper fun job.
But it wasn't enough, which iscrazy, and I just was like I
don't know, I have this idea andI can totally do it.
Why can't I?
You know why not?
And so quit my job and peoplethought I was crazy.
(07:12):
But that was the first realjump 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, andeven, you know, actually right
after college too.
I did a business plan coursewomen's economic ventures here
(07:33):
in Santa Barbara.
I went through their program soI definitely had this like
desire to be an entrepreneurbefore I actually took that leap
, you know, after Burton.
Speaker 1 (07:42):
So what was that first entrepreneurial venture?
Was that the Bon Affair?
Speaker 2 (07:46):
Yeah, so that was my wine company and I did that for
9, 10 years, yep.
Speaker 1 (07:50):
And so with that, unless I'm mistaken, you started
that during the 08 recession.
Speaker 2 (07:57):
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, thatwe're in a recession and I am.
I've told my whole friends andfamily that I'm going to start
this company and now it's likesheer determination I have to
(08:19):
make this happen.
But I had a lot of thingsworking against me for sure.
Speaker 1 (08:24):
Yeah, so what was the confidence I mean not even the
confidence what was the mindsetthat you had to adapt or develop
to essentially become anentrepreneur, and especially in
such a crazy time, that reallyallowed you to grow into the
(08:45):
person that you are today?
Speaker 2 (08:45):
Yeah, I think it's.
You know I lived by the wordspatience and persistence.
I kind of had this awarenessthat, like I don't, I don't know
what I don't know, I don't knoweverything.
I know that I have a lot I needto figure out, but I do think
(09:07):
that my that seven years I spentin product management and
product development.
The whole seven years I wasjust spending figuring things
out.
You know, how do we make this?
How do we get this to cost less?
How do we make this moresustainable?
Like, how do we find a newfactory?
So I had spent seven yearsbasically learning how to figure
(09:28):
things out.
And then I just applied that to, you know, a business venture.
And I think that's one of thebiggest things.
If you can just learn how tofigure things out and it's
interesting I kind of think thatthat's just something everybody
knows how to do.
But I've learned since thatit's not, and it can be a skill
that's learned, or some peoplejust have more of an inclination
(09:48):
to do that on their own.
But if you can just approachthings with a I'm going to just
do whatever it takes to figureit out.
It's amazing how much you canaccomplish.
You know, it's crazy.
Speaker 1 (10:08):
No, that is true, right, I mean, there's a
solution to every problem, butit's just your willingness to
find that solution and havepersistence and patience too,
because, again, solution numberone might not be the real
solution, right, so it takes alittle bit of time, but how?
So?
You said you were in that for70 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 leadingup to kind of how I pivoted out
of it, but I ended up justclosing it down.
It was the hardest decisionI've ever made in my life and I
could look at it, you know.
I realize now like it.
One, you know, frame ofreference is that I quit and
(10:48):
gave up on that company.
But how I truly see it is thatI actually opened myself up to a
completely different life,started a family my husband and
I had put off having kids.
I'd put my entire personal lifeexcept for gay married on hold
to run that company and gotextremely burnt out and realized
(11:10):
the dream wasn't the dreamanymore 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 withand that wasn't what I wanted.
And it was a huge pivot toreally get what I truly want in
life, which is, you know,business ventures, flexibility,
(11:34):
time with my family, financialfreedom.
Those are the things I trulycare about, not like this ego
drive of growing this hugecompany.
That just wasn't cutting it forme anymore, I guess.
Speaker 1 (11:46):
No, I mean, it makes sense.
I mean we all have those pivotsand there's, no, there's no
correct pivot, you know, in lifeit's whatever fits you or
fulfills you in the moment, aswell 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 yourlife on hold, but what was the
(12:09):
next career chapter in your life?
Speaker 2 (12:12):
said you put your life on hold.
But what was the next careerchapter in your life?
Yeah, so I took a year.
I was pregnant and basically Ihad gone out to raise another
round of funding and I was likesick as a dog.
And that's when I was just likeyou know what I just.
This is so not the top priorityanymore.
So I took a year off spent withmy son newborn.
That was a whole nother likewhoa.
This is not easy either.
I don't want to be a stay athome mom, that's for sure.
(12:34):
I love him to death, but I loveworking and I don't want to not
work.
So I.
But I also was like I don'tever want to have my own company
again.
I will be totally happy justcollecting a paycheck.
I don't need to have my ownbusiness.
But in the back of my head andI did say out loud to my husband
a few times but if I ever dostart another business, it'll be
(12:55):
a service-based company.
I'm not doing consumer productsagain.
So I ended up just getting ajob as a VP of sales and
marketing with a music companyhere in Santa Barbara.
I did that for five years andthen I realized I overcorrected.
I was like I don't want to workfor someone else.
So I was like, okay, this isn'tsustainable either.
(13:16):
I need way more flexibility.
It was fun, but I just realizedI 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 abeing the boss and having that
flexibility to having a boss isdefinitely not an easy
transition, you know, and unlessyou disagree.
Speaker 2 (13:43):
Well, I think for certain people it's not.
I think for me the reason itworked is because I had so much
respect and appreciation forwhat it is like in that CEO
founder role that I didn't buttheads with them because I saw my
job as supporting their vision.
(14:03):
Right, it wasn't my company, Iwasn't responsible for payroll,
I didn't have the luxury to callthose shots of what the vision
and direction should be.
So in some ways I think I waslike a great employee because I
fully respected how hard it isto be in that CEO you know
founder role and I saw my roleas VP of sales and marketing to
(14:28):
ultimately support their visionand then execute it.
But I do think some people getin there and they, you know it
can be a different situationwhere they feel like they know
better or they have their ownway of wanting to do it.
But unless you are in that CEOfounder role like you, just you
know that is the benefit thatthey get for putting in all
(14:49):
those painful, long hours andtaking 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 youhave the creativity, you know
how to build, but you don't haveto have as much of the stress.
But there comes, you know, somegive and take with that.
You know, if you're a creative,creative type and you want to
(15:14):
do it a certain way, it's likesometimes you gotta, you know,
know that you can't go that wayIf the person above you is
telling you, hey, that's notwhat we want to do, Right, so
there's there's there's pros andcons, but again, it just
whatever pivot works best foryou at the time.
I do, before we get too faraway from it was Bonifera.
Was that the company that youwere 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 toShark 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 mastermindsweren't as common or prevalent
as they are now.
So the MBA was kind of a veryexpensive way to network, but it
(16:09):
took me.
So I started pitching investors.
It took me 18 months of nonstoppitching hundreds of investors
to raise the first half millionfrom non-friends and family.
I did a friends and familyround and then I raised a half
million in convertible notesfrom non-friends and family and
that was enough to get usstarted.
(16:30):
The total raise was going to be2 million, but we got the first
tranche of 500,000 and went todo our first production run and
we lost a hundred thousanddollars worth of inventory.
It was devastating.
There was only one bottler thatwould take us on because of all
these licensing requirementsThen.
A lot of those are not issuesnow, but they were out of
(16:52):
business six months later.
So devastating place to bewhere you've put your heart and
soul into.
Investors have put their trustin you and then you lose
$100,000 and you have noinventory.
So basically we had to put aton of money into licensing,
legal all that.
We launched a direct toconsumer website.
(17:12):
So basically we were going torun out of money a lot sooner,
weren't hitting the milestoneswe needed to hit to get that
next one and a half million.
So I was like, you know, this is, this is not good.
We're potentially going to endup doing a down round if I, you
know, raise more money and Ican't get the valuation up.
(17:32):
So I had an advisor who keptsaying you should go on Shark
Tank, you should go on SharkTank.
And I was like, oh, I don'twant to go on that show.
And then I was going to meethim for lunch one day and I was
like I have to just apply beforeI go meet with him so I can
just tell him I did it and hecan stop bugging me.
So I applied for the show andthen, you know, a few months
(17:53):
later and got a call and I waslike, oh my God, now I actually
have to like, do this.
So jumped through all the hoopsand you know they said I'd been
accepted to the show and Ipracticed like crazy, you know,
to be um to get on there.
I list, I watched every episode, I wrote down all the investor
(18:14):
questions and I got up there andit was all ready to pitch.
I'm in the dressing room andthe producers came in and they
said we're so sorry, you're notgoing to get to pitch today.
We don't know if you'll getanother shot.
I was like devastated.
I'm like, oh my God, I justwant to like get it out at this
point.
So I went home and then a fewdays later I got a call and they
said you know, there's a 50-50chance you'll get to pitch
tomorrow.
Do you want to come up?
(18:45):
And I was like kind of goinginto it like this is I'm so
thankful for the opportunity.
This is like just a cool lifeexperience.
I'm going to try to just enjoyit as much as I can.
And I went out there and it'sit's pretty brutal.
They're all firing questions atthe same time.
You know, trying to throw youoff.
I was in there for about an hourand they edited it down to 10
minutes but ended up getting thedeal with Mark Cuban, which was
(19:10):
amazing and super cool, likesuch a great guy.
I can't say enough good thingsabout him.
He was like, actually involved,had contact with him.
He had a whole team of peoplethat supported us.
But what happened is, you know,we went from.
You go from where you're kindof just begging distributors,
begging retailers to take yourproduct when nobody knows about
you, and then you get all thisexposure and it's just a shot in
(19:30):
the arm and now everyone'scoming to you and it's so hard
to say no, right, because you'vejust been like so you want to
take advantage of all theseopportunities.
So the big, big lesson learnedwas growing too fast without the
right resources is recipe forburnout and very, very
challenging.
Mark was financing inventoryruns for us but he just doesn't
(19:53):
do further equity investments.
It's kind of his rule of thumb.
So I ended up.
It's very challenging inalcohol to be profitable and
this was kind of carving out anew category.
This was before White Claw cameout.
It was like an all natural,healthier, lighter wine spritzer
no preservatives, no sugar anddistributors are like why would
(20:14):
anybody want this?
Why?
So it was a very expensivething as a small brand to try to
educate an industry and an endconsumer on a new product
category.
So there was a lot of factorsinvolved like market timing,
lack of resources, trying to gotoo far too fast.
I think if I had launched itfive years later, as the
(20:37):
category had started to already,you know, be carved out, it
could have been a differentstory, 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, alcoholoptions.
So anyway, yeah, that was theShark Tank story, but again,
can't say enough good thingsabout the show and you know Mark
(20:58):
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 andpitching your peers is one thing
right, and it could already beget.
You can get nerve wracked, youknow, just stepping on stage in
front of your peers, yourcolleagues, let alone like just
an audience.
But when you're in front ofsuch like high profile
individuals, you know, on theshow, what was that like?
Did you know that feeling rightwhen you actually saw them all
(21:23):
you know, lined up ready tobasically 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 ofit for sure.
Um, I think that's why anybodywho's gone on the show that I've
coached afterwards.
It's like you have got topractice and be so dialed.
It's so different than anyother pitch Because you can't
(21:52):
rely, yeah, the nerves just rampup and the adrenaline and so
you just have.
It has to be like muscle memoryat that point responding to
questions and the pitch itself,because I remember the producers
are like you know, we're goingto hit record and even if you
pee your pants, we're not goingto stop recording.
So anything spare game once wehit record, you know.
(22:12):
So you're like it is definitelyhigh pressure, but I don't know
it was fun.
Somehow I got, I did a greatjob and, you know, got a good
edit and pulled it off.
But I put a lot of time andeffort 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 andknowing that you know, you said
it's, you know like an hourlong of of Q&A and back and
forth, it's like, man, it justseems like it is five, 10
minutes, and so I can't evenimagine that pressure.
So that's a win just in yourlife book of being able to do
(22:50):
that.
Yeah it's fun.
So I mean, now you'vetransitioned from the Bonifera
and you transitioned from beingan entrepreneur.
Was the next step your realestate, your rentals, or was
there something in between those?
Speaker 2 (23:06):
Yeah, no.
So, um, when I had the, the jobat the music company um, covid
hit 2020 and we went to rent aplace in Paso Robles for a week
and it had a pool and I you knowwe're everybody was dying to
get out of their house.
We were cooped up with atoddler and I was crunching the
(23:31):
numbers.
I'm like, wow, these guys arekilling it with what we're
paying here and we're drivinghome and we're always looking at
real estate.
Anyway, I had bought a triplexin my early 20s.
I fixed up each one, so I'vealways been in tune with real
estate.
My parents used to renovatehouses and had rental units and
stuff like that.
So after that trip, there was aproperty on the drive home.
(23:54):
My son had to pee.
We pull off on the side of thehighway and I said to my husband
I said there is a house rightover there that's for sale, that
has a pool.
Can we go look at it in thislittle town, little wine country
town?
And so we drove by it and Iwent home and I crunched the
numbers and the next day we putan offer in and we hired a
(24:14):
management company because I wasworking and they were so
horrible, I can't even tell you.
The customer service, likeeverything was just so bad.
They were renting it for supercheap and I was like this is not
going to work and my husband'slike you should do it, you
should do it, and I'm like Idon't have time to do it.
And then finally I was like,okay, I'll do it.
So I pulled the like wake up at4am, set up all the software.
(24:38):
We knew we wanted to keep buyingrental properties, buying
rental properties.
So I like set up the you knowto be able to manage like 100
properties, went kind ofoverboard but started managing
it myself and I was like,actually this is kind of fun.
I like the hospitality side ofit.
I love creating a greatexperience for people.
And I was like actually I couldjust do this and it kind of
(24:58):
checks that it's a service basedbusiness.
I love the real estateinvesting side and kind of going
back a little bit even to that,always looking, you know, sense
of adventure.
The fun thing with real estateis there's always a new deal.
There's always you can belooking for new deals.
You know development projects,renovations, it's like there's
(25:19):
always something new, but it'sstill within the same bubble.
So I ended up quitting the joband started doing this full time
and then got this pretty wellset up to give myself a lot of
time and flexibility and startedthe podcast.
So that's kind of how thatturned out.
Speaker 1 (25:40):
Okay, so that was actually my next question, but
before I ask that, so how manyreal estate properties or rental
properties do you guyscurrently have?
Speaker 2 (25:49):
now, if you don't mind me asking, yeah, so we own
three and then I manage another30.
And most of those are in Stowe,Vermont.
So 24 properties in Stowe,Vermont, 3,000 miles away, and
the rest are here in SantaBarbara.
And we bought a property inVermont because we go back there
(26:12):
every summer, Because, hence,growing up in New Hampshire,
most of my family is in Vermontnow and so the numbers just
worked really well.
There we saw this gorgeousplace 18 acres.
It had seven lots alreadypre-approved through the state
to develop and we were like thisis a great spot.
So we bought that and then itjust kind of word of mouth,
(26:35):
started growing the rental sideof it or the management side of
it there and set up my team, youknow, and it was definitely
some growing pains at firstbecause of time zones and you
know again, learning a newbusiness, it's not easy Again,
you don't know what you don'tknow at the beginning, looking
back, like I would have hadthings way more dialed in
(26:57):
earlier in certain areas, youknow, but you just kind of keep
evolving and fine tuning untilyou 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 threehouses, but three homes, but
you're also managing otherpeople that are doing the same
as well, right?
Speaker 2 (27:18):
Yeah, so these are either just second homeowners,
where they vacation there acouple times a year.
They're all larger luxuryproperties and we just so we
manage the whole property forthem.
We, our maintenance team, takescare of all the maintenance,
our turnover team, guestrelations, booking, marketing,
all that stuff.
So it's yeah, it's a servicefor homeowners who want to rent
(27:41):
their house when they're notthere.
Speaker 1 (27:48):
Okay, I mean that's awesome.
And then you said you startedthe podcast after this company
was already started and it's theSeed Money Podcast, right?
And so what was the idea behindstarting the podcast and what
was the purpose for the initialstart?
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 hadso many mentors over the years
and so many people helped me inthose 10 years of starting Bon
Affair like just gave their timeto help me learn how to raise
(28:22):
money.
You don't just know that stuff,I mean, you can read about it
online but you really needpeople who've been through it to
point out some of the thingsthat can go wrong to help you
avoid some of the commonpitfalls.
It's not an easy thing to do togo out and raise money and
(28:45):
there is so much passion behinda person who has an idea and is
committed to going out to getfunding to launch their idea.
You have to be so passionateabout what you're doing and so
excited and committed anddedicated and I just love that
passion.
I think it's so inspiring andit's just needed to make the
(29:08):
world go round and we need moregood entrepreneurs, and so it
was kind of my way of givingback.
I was like I love that earlystage process.
My story isn't of raisingmillions and millions and
millions of dollars, but it'sraising money against all odds,
like I had no revenue.
I had no experience in theindustry.
It was in a recession.
(29:29):
I'm female and a very male,especially then in 2008, even
more so.
So I feel like you know, I justhave so much to give and I love
talking about that stuff.
So I started the podcast as away to just give back and help,
(29:51):
and I'll review people's pitchdecks.
I've started taking on someone-on-one coaching clients who
just they're so busy in theircompany They've got maybe a
million in revenue.
They've never raised money andthey don't know how to put their
pitch deck together to make itcompelling.
They put a gazillion words on aslide and it's like nobody's
going to read all that.
So I love I mean I could justdo pitch decks all day.
It's so, it's fun for me.
I absolutely love doing it.
So, um, so that's why I startedthe podcast and I just kind of
(30:13):
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 yearor 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 ofbusiness too, because you could
be a great business owner and agreat entrepreneur, but pitching
and raising money, it's not.
It's, it's a whole separatesubcategory of business.
And I mean we, for for myactual business, like you know,
(30:43):
we do have an investor and eventhat one pitch, I mean that for
for my actual business, like youknow, we do have an investor
and even that one pitch, I meanthat was one of many, but that
one, it was still again samething with you Like there was no
revenue, there was, therewasn'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 eventhe information you're giving
out on that podcast is going tobe huge in such so niche down on
(31:06):
that.
So I mean the one question Iwould ask is when?
When should a startup decide tobootstrap it and figure it out
or try to raise money andoutside 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 wantto say before that the other
reason I started it is becauseso much of the content out there
on this topic are from thisSilicon Valley go big or go home
kind of VCs putting out content, and it's very much from the
investor perspective and itdoesn't cover that like human
(31:48):
side of what you're goingthrough when you're trying to
raise money and the challenge,the mental challenge there, and
so to how that applies to yourquestion, is that I think there
is this culture where people dofeel like I need to grow a huge
company.
Well, it's not as much anymore.
It used to be a lot worse likethis, but there's still this
(32:10):
culture of if I'm going to starta company, I need to grow it
big or I need to get it to acertain dollar amount.
Even a lot of the VCs now nowthey're looking more and more
for companies that can reachprofitability and be more
sustainable.
You know this like invest a tonof money into something and
then just have it flop a yearlater is, I think, getting old
(32:31):
right For everybody involved.
So, in terms of like when tobootstrap versus when to raise
money, I think there are certaincompanies that you can
bootstrap and there are certaincompanies, like consumer
products, where you just needinventory and you need marketing
dollars and you don't alwayshave that money, and so I think
(32:52):
a lot of it comes down to whatyour risk threshold is right.
So some people I mean somepeople like mortgage their house
to put it into their company.
I do not recommend doing that.
So the one thing I never did Inever personally guaranteed
anything.
I didn't get sued.
I wasn't in debt when mycompany ended, so I went out, I
(33:14):
put in what I was comfortableputting in and then I raised
money after that and I raised itfrom non friends and family
because I didn't want to putthem at risk.
So I'd say you know youbootstrap until you, for the
most important thing in thebeginning is really setting a
goal for your company thataligns with your personal goals,
(33:35):
right.
So if you are in your headgoing, I need to grow this to 20
million, like why, why do youwant to grow this to 20 million?
Like why, why do you want togrow that to 20 million?
What's the real reason behindthat?
And if you still want to growit to 20 million, then you
probably need to go out to raisemoney.
If you are growing it to justown your own company and have
more money and flexibility thatyou don't necessarily need to
(33:58):
grow it to 20 million and onceyou get investors involved,
you're just working for them,right?
You're not necessarily workingfor yourself as much anymore.
Now you're on their trajectory.
You have to hit certainmilestones.
So I think there's a lot offactors to that question of
bootstrapping versus, you know,raising money like the company
(34:19):
I'm working with right now.
They've been bootstrappingversus you know, raising money
like the company I'm workingwith right now.
They've been bootstrappingsince they started in 2016.
They were kind of successful inother areas before but you know
, still not paying themselvesand that's where it gets really
exhausting.
So when you're at that tippingpoint of like we just need more
(34:40):
money to get ahead and make thissustainable, you might need to
go out and raise more moneybecause typically bootstrapping,
you know you're cash strapped.
You're not paying yourself amarket salary, most likely, and
you can only do that for so long.
Some people can do that, are ina situation that you can do
that much longer.
Other people, you know, knowcan't do it for as long, so I
(35:01):
don't know if that was helpfulat all, but I think there's just
a lot of variables there andultimately it comes down to like
figuring out what your personalgoals and then deciding you
know how to incorporate yourbusiness goals with your
personal goals and letting thatbe the foundation for the
decision no, I think I mean thatanswered the question in detail
(35:23):
.
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 anylasting message for the up and
coming generations, right, shortor long.
But what is one message thatyou 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 aboutwhat other people are doing.
I think it's very easy tocompare yourself and feel like
you're supposed to do this,you're supposed to do that.
And it is the brave decision tonot follow that and to just
carve out your own path.
(36:07):
Maybe your path zigzags, maybeit's not, you know, like your
average thing, and that istotally okay.
There's no right or wrong wayto do it and you just have to,
like, go after what works foryou and just, I think, get
really in tune with what it isthat you want out of life.
You know what is it?
What are you?
(36:27):
Again, those personal goals areso, so, so important and should
be kind of your anchor foreverything 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 reallyfulfilling life.
So that's what I would say.
No, that's awesome.
It is true, Not everyone'sjourney, even to the same or
similar goal, is going to be thesame right.
Yours might zig and zag andmine might go just up and then
take a huge left turn right, andso that is so awesome.
Where can people connect withyou and where can they find your
(37:00):
podcast?
At?
Speaker 2 (37:02):
Yeah, so podcast is on all the podcast channels.
Just search Seed Money Jaylaand it'll pop up, and then
LinkedIn is the best spot toconnect with me.
I'm pretty active on there.
Speaker 1 (37:14):
Awesome.
Well, guys, that will be in theshow notes as well.
If you're watching on YouTube,it'll be in the video
description.
Make sure you guys go check outher show.
Make sure you guys check herout on LinkedIn.
But I just want to say, youknow, thank you so much for
taking the time out of your dayagain to you know, hop on and
drop so much knowledge ofbusiness and your experience of
business in such a cool, youknow, journey that you've been
(37:35):
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.
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 youthink you manifest.
So get ready to rise, cause weabout 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, onlypositive thoughts.
(00:20):
What is up, guys?
Welcome to another episode ofthe Mindset Cafe podcast.
It's your boy, devin, and todaywe got a special guest on.
We got Jayla Siciliano.
I saved myself on that one.
I told her I was going to gettongue tied a little bit on it,
but I'm excited to dive in.
The one thing that stuck out tome when I was looking into her
(00:45):
background is she's a Shark Takealumni, right.
But also there's some coolthings that she has her own
podcast that we're going to diveinto.
She is a real estate investor,she is a CEO and, honestly,
she's just a well roundedentrepreneur.
So we're going to dive into allof that.
But again, her podcast is theSeed Money Podcast.
So make sure you guys checkthat out.
(01:05):
But without further ado.
Jayla, thanks so much fortaking the time out of your day
to hop on the Mindset Cafe.
Speaker 2 (01:11):
Yeah, thanks for having me.
Great to be here.
This is fun to connect.
Speaker 1 (01:15):
Definitely, and so I want to dive.
I like to rewind, you know,right out the gate, and before
we dive into all of youraccolades and all your ventures,
what was your bring up likeright?
Because this is what connectspeople and kind of lets it
resonate.
You know where you're currentlyat to.
You know where you started from.
(01:35):
So what was your childhood like?
What did your parents do?
What was that backstory like?
Speaker 2 (01:41):
Yeah, so I grew up in a small town in New Hampshire
and my dad had his own businessa small business land surveying
company.
My mom just basically was stayat home mom and did his
bookkeeping and worked for himhere and there, and so I grew up
seeing my parents were home allthe time, flexibility, plenty
(02:03):
of time to take vacations and dostuff like that.
But I also kind of on the flipside of that grew up with, you
know, my dad being one of thoseentrepreneurs 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.
(02:24):
You can have flexibility, youcan be passionate about what you
do, love what you do, besuccessful.
But I also had to shift some ofthat you know, do it, do
everything yourself kind ofmindset.
That was also instilled in me.
So, yeah, small town and dayafter graduation I could not
(02:44):
wait to get out of there.
I moved to Long Island and thenI moved all around after that.
But yeah, overall had a really,you know, very thankful.
I grew up in a great placelittle lake and a ski resort.
I love the outdoors because ofthat.
But I live in Santa Barbara now, and you couldn't pay me enough
money to move back to thewinter, so Santa Barbara is
(03:07):
beautiful too.
Speaker 1 (03:08):
I mean, I'm in LA, it's a little more city out here
, but I believe me, I've been toSanta Barbara so many times and
I love it out there it isbeautiful.
So I mean, with with you movingaround where you graduated and
you started moving around, whatwas that like?
Cause I mean, each place you'removing to, you're essentially
looking for new work, you know,and so forth.
So what was that mindset Like?
(03:28):
Why did you want to kind ofmove around and kind of venture
all the way out to Santa Barbara?
Speaker 2 (03:35):
Yeah, that's a great question, I think you know.
Looking back, I think I Idefinitely love new things.
I really do have a deep senseof adventure.
I'm actually not sure wherethat came from.
It's not like I traveled allaround the world as a kid or
anything, but I just get antsy,would get antsy and be like want
(03:57):
to go somewhere else andthere's so much more to do and
so much more to see and why notjust try another place.
So that kind of came out bymoving around and then I think
later it came out and starting,you know, career shifts and
business shifts and stuff likethat.
But I think it really was justrooted in like this excitement
(04:19):
to try new things and always beon a new adventure.
And I I still a little bit likewe're leaving for Belize in
three days.
I absolutely can't wait.
I have a thing where I try totravel to a new country, at
least one new country every year.
I just love traveling and so Ithink.
But ultimately I think it waskind of that, you know, looking
(04:39):
for something new and exciting.
Speaker 1 (04:42):
Oh, I mean that's awesome, though, because getting
to see the world and even justaround the country and I was
talking to someone about thisbecause I mean born and raised
in LA and until becoming anentrepreneur and joining
Business Masterminds and us,doing quarterly meetups and all
that kind of stuff and travelingto other states there's a
different way of life, evenwithin the United States, that
(05:04):
you don't realize unless youactually visit, right Cause I
mean you think I'm being bornand raised in LA.
You think everything is likefast paced, you know hustle and
bustle and all that kind ofstuff.
And you go to Montana and allof a sudden we're at a
restaurant and I was like, allright, come on.
Like let's like I've got thingsto do, like but it's.
(05:26):
And then, but it's like in themovies where you know the the
waitress is walking around andintroducing herself to each
person and have a conversationwith each person, and I'm like
like, oh my goodness, like comeon, like this is, this is taking
forever.
But then at the same time yourealize that maybe you should
just slow down and, and you know, kind of appreciate the day,
right.
So I think that's so awesomewith, like you traveling and
(05:46):
everything, because you get tosee different cultures, you get
to see different ways of lifeand it really opens up your eyes
to be able to walk in someoneelse's shoes.
So, speaking of walking insomeone else's shoes and living
a life that is not necessarilyfor everyone, because it's not
the easiest path, what was yourintro to entrepreneurship?
Speaker 2 (06:08):
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 reallywanted to do that and I learned
how to sew.
And then, even in college andright after college, I had a
little art studio and I wasmaking, you know, leather
handbags and doing trunk shows.
(06:29):
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 acorporate job, which was great,
super fun.
Some would call the dream job ofworking at Burton Snowboards
(06:51):
and getting 60 days on themountain and traveling to Asia
and working with the team ridersSuper fun job.
But it wasn't enough, which iscrazy, and I just was like I
don't know, I have this idea andI can totally do it.
Why can't I?
You know why not?
And so quit my job and peoplethought I was crazy.
(07:12):
But that was the first realjump 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, andeven, you know, actually right
after college too.
I did a business plan coursewomen's economic ventures here
(07:33):
in Santa Barbara.
I went through their program soI definitely had this like
desire to be an entrepreneurbefore I actually took that leap
, you know, after Burton.
Speaker 1 (07:42):
So what was that first entrepreneurial venture?
Was that the Bon Affair?
Speaker 2 (07:46):
Yeah, so that was my wine company and I did that for
9, 10 years, yep.
Speaker 1 (07:50):
And so with that, unless I'm mistaken, you started
that during the 08 recession.
Speaker 2 (07:57):
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, thatwe're in a recession and I am.
I've told my whole friends andfamily that I'm going to start
this company and now it's likesheer determination I have to
(08:19):
make this happen.
But I had a lot of thingsworking against me for sure.
Speaker 1 (08:24):
Yeah, so what was the confidence I mean not even the
confidence what was the mindsetthat you had to adapt or develop
to essentially become anentrepreneur, and especially in
such a crazy time, that reallyallowed you to grow into the
(08:45):
person that you are today?
Speaker 2 (08:45):
Yeah, I think it's.
You know I lived by the wordspatience and persistence.
I kind of had this awarenessthat, like I don't, I don't know
what I don't know, I don't knoweverything.
I know that I have a lot I needto figure out, but I do think
(09:07):
that my that seven years I spentin product management and
product development.
The whole seven years I wasjust spending figuring things
out.
You know, how do we make this?
How do we get this to cost less?
How do we make this moresustainable?
Like, how do we find a newfactory?
So I had spent seven yearsbasically learning how to figure
(09:28):
things out.
And then I just applied that to, you know, a business venture.
And I think that's one of thebiggest things.
If you can just learn how tofigure things out and it's
interesting I kind of think thatthat's just something everybody
knows how to do.
But I've learned since thatit's not, and it can be a skill
that's learned, or some peoplejust have more of an inclination
(09:48):
to do that on their own.
But if you can just approachthings with a I'm going to just
do whatever it takes to figureit out.
It's amazing how much you canaccomplish.
You know, it's crazy.
Speaker 1 (10:08):
No, that is true, right, I mean, there's a
solution to every problem, butit's just your willingness to
find that solution and havepersistence and patience too,
because, again, solution numberone might not be the real
solution, right, so it takes alittle bit of time, but how?
So?
You said you were in that for70 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 leadingup to kind of how I pivoted out
of it, but I ended up justclosing it down.
It was the hardest decisionI've ever made in my life and I
could look at it, you know.
I realize now like it.
One, you know, frame ofreference is that I quit and
(10:48):
gave up on that company.
But how I truly see it is thatI actually opened myself up to a
completely different life,started a family my husband and
I had put off having kids.
I'd put my entire personal lifeexcept for gay married on hold
to run that company and gotextremely burnt out and realized
(11:10):
the dream wasn't the dreamanymore 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 withand that wasn't what I wanted.
And it was a huge pivot toreally get what I truly want in
life, which is, you know,business ventures, flexibility,
(11:34):
time with my family, financialfreedom.
Those are the things I trulycare about, not like this ego
drive of growing this hugecompany.
That just wasn't cutting it forme anymore, I guess.
Speaker 1 (11:46):
No, I mean, it makes sense.
I mean we all have those pivotsand there's, no, there's no
correct pivot, you know, in lifeit's whatever fits you or
fulfills you in the moment, aswell 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 yourlife on hold, but what was the
(12:09):
next career chapter in your life?
Speaker 2 (12:12):
said you put your life on hold.
But what was the next careerchapter in your life?
Yeah, so I took a year.
I was pregnant and basically Ihad gone out to raise another
round of funding and I was likesick as a dog.
And that's when I was just likeyou know what I just.
This is so not the top priorityanymore.
So I took a year off spent withmy son newborn.
That was a whole nother likewhoa.
This is not easy either.
I don't want to be a stay athome mom, that's for sure.
(12:34):
I love him to death, but I loveworking and I don't want to not
work.
So I.
But I also was like I don'tever want to have my own company
again.
I will be totally happy justcollecting a paycheck.
I don't need to have my ownbusiness.
But in the back of my head andI did say out loud to my husband
a few times but if I ever dostart another business, it'll be
(12:55):
a service-based company.
I'm not doing consumer productsagain.
So I ended up just getting ajob as a VP of sales and
marketing with a music companyhere in Santa Barbara.
I did that for five years andthen I realized I overcorrected.
I was like I don't want to workfor someone else.
So I was like, okay, this isn'tsustainable either.
(13:16):
I need way more flexibility.
It was fun, but I just realizedI 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 abeing the boss and having that
flexibility to having a boss isdefinitely not an easy
transition, you know, and unlessyou disagree.
Speaker 2 (13:43):
Well, I think for certain people it's not.
I think for me the reason itworked is because I had so much
respect and appreciation forwhat it is like in that CEO
founder role that I didn't buttheads with them because I saw my
job as supporting their vision.
(14:03):
Right, it wasn't my company, Iwasn't responsible for payroll,
I didn't have the luxury to callthose shots of what the vision
and direction should be.
So in some ways I think I waslike a great employee because I
fully respected how hard it isto be in that CEO you know
founder role and I saw my roleas VP of sales and marketing to
(14:28):
ultimately support their visionand then execute it.
But I do think some people getin there and they, you know it
can be a different situationwhere they feel like they know
better or they have their ownway of wanting to do it.
But unless you are in that CEOfounder role like you, just you
know that is the benefit thatthey get for putting in all
(14:49):
those painful, long hours andtaking 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 youhave the creativity, you know
how to build, but you don't haveto have as much of the stress.
But there comes, you know, somegive and take with that.
You know, if you're a creative,creative type and you want to
(15:14):
do it a certain way, it's likesometimes you gotta, you know,
know that you can't go that wayIf the person above you is
telling you, hey, that's notwhat we want to do, Right, so
there's there's there's pros andcons, but again, it just
whatever pivot works best foryou at the time.
I do, before we get too faraway from it was Bonifera.
Was that the company that youwere 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 toShark 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 mastermindsweren't as common or prevalent
as they are now.
So the MBA was kind of a veryexpensive way to network, but it
(16:09):
took me.
So I started pitching investors.
It took me 18 months of nonstoppitching hundreds of investors
to raise the first half millionfrom non-friends and family.
I did a friends and familyround and then I raised a half
million in convertible notesfrom non-friends and family and
that was enough to get usstarted.
(16:30):
The total raise was going to be2 million, but we got the first
tranche of 500,000 and went todo our first production run and
we lost a hundred thousanddollars worth of inventory.
It was devastating.
There was only one bottler thatwould take us on because of all
these licensing requirementsThen.
A lot of those are not issuesnow, but they were out of
(16:52):
business six months later.
So devastating place to bewhere you've put your heart and
soul into.
Investors have put their trustin you and then you lose
$100,000 and you have noinventory.
So basically we had to put aton of money into licensing,
legal all that.
We launched a direct toconsumer website.
(17:12):
So basically we were going torun out of money a lot sooner,
weren't hitting the milestoneswe needed to hit to get that
next one and a half million.
So I was like, you know, this is, this is not good.
We're potentially going to endup doing a down round if I, you
know, raise more money and Ican't get the valuation up.
(17:32):
So I had an advisor who keptsaying you should go on Shark
Tank, you should go on SharkTank.
And I was like, oh, I don'twant to go on that show.
And then I was going to meethim for lunch one day and I was
like I have to just apply beforeI go meet with him so I can
just tell him I did it and hecan stop bugging me.
So I applied for the show andthen, you know, a few months
(17:53):
later and got a call and I waslike, oh my God, now I actually
have to like, do this.
So jumped through all the hoopsand you know they said I'd been
accepted to the show and Ipracticed like crazy, you know,
to be um to get on there.
I list, I watched every episode, I wrote down all the investor
(18:14):
questions and I got up there andit was all ready to pitch.
I'm in the dressing room andthe producers came in and they
said we're so sorry, you're notgoing to get to pitch today.
We don't know if you'll getanother shot.
I was like devastated.
I'm like, oh my God, I justwant to like get it out at this
point.
So I went home and then a fewdays later I got a call and they
said you know, there's a 50-50chance you'll get to pitch
tomorrow.
Do you want to come up?
(18:45):
And I was like kind of goinginto it like this is I'm so
thankful for the opportunity.
This is like just a cool lifeexperience.
I'm going to try to just enjoyit as much as I can.
And I went out there and it'sit's pretty brutal.
They're all firing questions atthe same time.
You know, trying to throw youoff.
I was in there for about an hourand they edited it down to 10
minutes but ended up getting thedeal with Mark Cuban, which was
(19:10):
amazing and super cool, likesuch a great guy.
I can't say enough good thingsabout him.
He was like, actually involved,had contact with him.
He had a whole team of peoplethat supported us.
But what happened is, you know,we went from.
You go from where you're kindof just begging distributors,
begging retailers to take yourproduct when nobody knows about
you, and then you get all thisexposure and it's just a shot in
(19:30):
the arm and now everyone'scoming to you and it's so hard
to say no, right, because you'vejust been like so you want to
take advantage of all theseopportunities.
So the big, big lesson learnedwas growing too fast without the
right resources is recipe forburnout and very, very
challenging.
Mark was financing inventoryruns for us but he just doesn't
(19:53):
do further equity investments.
It's kind of his rule of thumb.
So I ended up.
It's very challenging inalcohol to be profitable and
this was kind of carving out anew category.
This was before White Claw cameout.
It was like an all natural,healthier, lighter wine spritzer
no preservatives, no sugar anddistributors are like why would
(20:14):
anybody want this?
Why?
So it was a very expensivething as a small brand to try to
educate an industry and an endconsumer on a new product
category.
So there was a lot of factorsinvolved like market timing,
lack of resources, trying to gotoo far too fast.
I think if I had launched itfive years later, as the
(20:37):
category had started to already,you know, be carved out, it
could have been a differentstory, 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, alcoholoptions.
So anyway, yeah, that was theShark Tank story, but again,
can't say enough good thingsabout the show and you know Mark
(20:58):
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 andpitching your peers is one thing
right, and it could already beget.
You can get nerve wracked, youknow, just stepping on stage in
front of your peers, yourcolleagues, let alone like just
an audience.
But when you're in front ofsuch like high profile
individuals, you know, on theshow, what was that like?
Did you know that feeling rightwhen you actually saw them all
(21:23):
you know, lined up ready tobasically 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 ofit for sure.
Um, I think that's why anybodywho's gone on the show that I've
coached afterwards.
It's like you have got topractice and be so dialed.
It's so different than anyother pitch Because you can't
(21:52):
rely, yeah, the nerves just rampup and the adrenaline and so
you just have.
It has to be like muscle memoryat that point responding to
questions and the pitch itself,because I remember the producers
are like you know, we're goingto hit record and even if you
pee your pants, we're not goingto stop recording.
So anything spare game once wehit record, you know.
(22:12):
So you're like it is definitelyhigh pressure, but I don't know
it was fun.
Somehow I got, I did a greatjob and, you know, got a good
edit and pulled it off.
But I put a lot of time andeffort 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 andknowing that you know, you said
it's, you know like an hourlong of of Q&A and back and
forth, it's like, man, it justseems like it is five, 10
minutes, and so I can't evenimagine that pressure.
So that's a win just in yourlife book of being able to do
(22:50):
that.
Yeah it's fun.
So I mean, now you'vetransitioned from the Bonifera
and you transitioned from beingan entrepreneur.
Was the next step your realestate, your rentals, or was
there something in between those?
Speaker 2 (23:06):
Yeah, no.
So, um, when I had the, the jobat the music company um, covid
hit 2020 and we went to rent aplace in Paso Robles for a week
and it had a pool and I you knowwe're everybody was dying to
get out of their house.
We were cooped up with atoddler and I was crunching the
(23:31):
numbers.
I'm like, wow, these guys arekilling it with what we're
paying here and we're drivinghome and we're always looking at
real estate.
Anyway, I had bought a triplexin my early 20s.
I fixed up each one, so I'vealways been in tune with real
estate.
My parents used to renovatehouses and had rental units and
stuff like that.
So after that trip, there was aproperty on the drive home.
(23:54):
My son had to pee.
We pull off on the side of thehighway and I said to my husband
I said there is a house rightover there that's for sale, that
has a pool.
Can we go look at it in thislittle town, little wine country
town?
And so we drove by it and Iwent home and I crunched the
numbers and the next day we putan offer in and we hired a
(24:14):
management company because I wasworking and they were so
horrible, I can't even tell you.
The customer service, likeeverything was just so bad.
They were renting it for supercheap and I was like this is not
going to work and my husband'slike you should do it, you
should do it, and I'm like Idon't have time to do it.
And then finally I was like,okay, I'll do it.
So I pulled the like wake up at4am, set up all the software.
(24:38):
We knew we wanted to keep buyingrental properties, buying
rental properties.
So I like set up the you knowto be able to manage like 100
properties, went kind ofoverboard but started managing
it myself and I was like,actually this is kind of fun.
I like the hospitality side ofit.
I love creating a greatexperience for people.
And I was like actually I couldjust do this and it kind of
(24:58):
checks that it's a service basedbusiness.
I love the real estateinvesting side and kind of going
back a little bit even to that,always looking, you know, sense
of adventure.
The fun thing with real estateis there's always a new deal.
There's always you can belooking for new deals.
You know development projects,renovations, it's like there's
(25:19):
always something new, but it'sstill within the same bubble.
So I ended up quitting the joband started doing this full time
and then got this pretty wellset up to give myself a lot of
time and flexibility and startedthe podcast.
So that's kind of how thatturned out.
Speaker 1 (25:40):
Okay, so that was actually my next question, but
before I ask that, so how manyreal estate properties or rental
properties do you guyscurrently have?
Speaker 2 (25:49):
now, if you don't mind me asking, yeah, so we own
three and then I manage another30.
And most of those are in Stowe,Vermont.
So 24 properties in Stowe,Vermont, 3,000 miles away, and
the rest are here in SantaBarbara.
And we bought a property inVermont because we go back there
(26:12):
every summer, Because, hence,growing up in New Hampshire,
most of my family is in Vermontnow and so the numbers just
worked really well.
There we saw this gorgeousplace 18 acres.
It had seven lots alreadypre-approved through the state
to develop and we were like thisis a great spot.
So we bought that and then itjust kind of word of mouth,
(26:35):
started growing the rental sideof it or the management side of
it there and set up my team, youknow, and it was definitely
some growing pains at firstbecause of time zones and you
know again, learning a newbusiness, it's not easy Again,
you don't know what you don'tknow at the beginning, looking
back, like I would have hadthings way more dialed in
(26:57):
earlier in certain areas, youknow, but you just kind of keep
evolving and fine tuning untilyou 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 threehouses, but three homes, but
you're also managing otherpeople that are doing the same
as well, right?
Speaker 2 (27:18):
Yeah, so these are either just second homeowners,
where they vacation there acouple times a year.
They're all larger luxuryproperties and we just so we
manage the whole property forthem.
We, our maintenance team, takescare of all the maintenance,
our turnover team, guestrelations, booking, marketing,
all that stuff.
So it's yeah, it's a servicefor homeowners who want to rent
(27:41):
their house when they're notthere.
Speaker 1 (27:48):
Okay, I mean that's awesome.
And then you said you startedthe podcast after this company
was already started and it's theSeed Money Podcast, right?
And so what was the idea behindstarting the podcast and what
was the purpose for the initialstart?
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 hadso many mentors over the years
and so many people helped me inthose 10 years of starting Bon
Affair like just gave their timeto help me learn how to raise
(28:22):
money.
You don't just know that stuff,I mean, you can read about it
online but you really needpeople who've been through it to
point out some of the thingsthat can go wrong to help you
avoid some of the commonpitfalls.
It's not an easy thing to do togo out and raise money and
(28:45):
there is so much passion behinda person who has an idea and is
committed to going out to getfunding to launch their idea.
You have to be so passionateabout what you're doing and so
excited and committed anddedicated and I just love that
passion.
I think it's so inspiring andit's just needed to make the
(29:08):
world go round and we need moregood entrepreneurs, and so it
was kind of my way of givingback.
I was like I love that earlystage process.
My story isn't of raisingmillions and millions and
millions of dollars, but it'sraising money against all odds,
like I had no revenue.
I had no experience in theindustry.
It was in a recession.
(29:29):
I'm female and a very male,especially then in 2008, even
more so.
So I feel like you know, I justhave so much to give and I love
talking about that stuff.
So I started the podcast as away to just give back and help,
(29:51):
and I'll review people's pitchdecks.
I've started taking on someone-on-one coaching clients who
just they're so busy in theircompany They've got maybe a
million in revenue.
They've never raised money andthey don't know how to put their
pitch deck together to make itcompelling.
They put a gazillion words on aslide and it's like nobody's
going to read all that.
So I love I mean I could justdo pitch decks all day.
It's so, it's fun for me.
I absolutely love doing it.
So, um, so that's why I startedthe podcast and I just kind of
(30:13):
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 yearor 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 ofbusiness too, because you could
be a great business owner and agreat entrepreneur, but pitching
and raising money, it's not.
It's, it's a whole separatesubcategory of business.
And I mean we, for for myactual business, like you know,
(30:43):
we do have an investor and eventhat one pitch, I mean that for
for my actual business, like youknow, we do have an investor
and even that one pitch, I meanthat was one of many, but that
one, it was still again samething with you Like there was no
revenue, there was, therewasn'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 eventhe information you're giving
out on that podcast is going tobe huge in such so niche down on
(31:06):
that.
So I mean the one question Iwould ask is when?
When should a startup decide tobootstrap it and figure it out
or try to raise money andoutside 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 wantto say before that the other
reason I started it is becauseso much of the content out there
on this topic are from thisSilicon Valley go big or go home
kind of VCs putting out content, and it's very much from the
investor perspective and itdoesn't cover that like human
(31:48):
side of what you're goingthrough when you're trying to
raise money and the challenge,the mental challenge there, and
so to how that applies to yourquestion, is that I think there
is this culture where people dofeel like I need to grow a huge
company.
Well, it's not as much anymore.
It used to be a lot worse likethis, but there's still this
(32:10):
culture of if I'm going to starta company, I need to grow it
big or I need to get it to acertain dollar amount.
Even a lot of the VCs now nowthey're looking more and more
for companies that can reachprofitability and be more
sustainable.
You know this like invest a tonof money into something and
then just have it flop a yearlater is, I think, getting old
(32:31):
right For everybody involved.
So, in terms of like when tobootstrap versus when to raise
money, I think there are certaincompanies that you can
bootstrap and there are certaincompanies, like consumer
products, where you just needinventory and you need marketing
dollars and you don't alwayshave that money, and so I think
(32:52):
a lot of it comes down to whatyour risk threshold is right.
So some people I mean somepeople like mortgage their house
to put it into their company.
I do not recommend doing that.
So the one thing I never did Inever personally guaranteed
anything.
I didn't get sued.
I wasn't in debt when mycompany ended, so I went out, I
(33:14):
put in what I was comfortableputting in and then I raised
money after that and I raised itfrom non friends and family
because I didn't want to putthem at risk.
So I'd say you know youbootstrap until you, for the
most important thing in thebeginning is really setting a
goal for your company thataligns with your personal goals,
(33:35):
right.
So if you are in your headgoing, I need to grow this to 20
million, like why, why do youwant to grow this to 20 million?
Like why, why do you want togrow that to 20 million?
What's the real reason behindthat?
And if you still want to growit to 20 million, then you
probably need to go out to raisemoney.
If you are growing it to justown your own company and have
more money and flexibility thatyou don't necessarily need to
(33:58):
grow it to 20 million and onceyou get investors involved,
you're just working for them,right?
You're not necessarily workingfor yourself as much anymore.
Now you're on their trajectory.
You have to hit certainmilestones.
So I think there's a lot offactors to that question of
bootstrapping versus, you know,raising money like the company
(34:19):
I'm working with right now.
They've been bootstrappingversus you know, raising money
like the company I'm workingwith right now.
They've been bootstrappingsince they started in 2016.
They were kind of successful inother areas before but you know
, still not paying themselvesand that's where it gets really
exhausting.
So when you're at that tippingpoint of like we just need more
(34:40):
money to get ahead and make thissustainable, you might need to
go out and raise more moneybecause typically bootstrapping,
you know you're cash strapped.
You're not paying yourself amarket salary, most likely, and
you can only do that for so long.
Some people can do that, are ina situation that you can do
that much longer.
Other people, you know, knowcan't do it for as long, so I
(35:01):
don't know if that was helpfulat all, but I think there's just
a lot of variables there andultimately it comes down to like
figuring out what your personalgoals and then deciding you
know how to incorporate yourbusiness goals with your
personal goals and letting thatbe the foundation for the
decision no, I think I mean thatanswered the question in detail
(35:23):
.
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 anylasting message for the up and
coming generations, right, shortor long.
But what is one message thatyou 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 aboutwhat other people are doing.
I think it's very easy tocompare yourself and feel like
you're supposed to do this,you're supposed to do that.
And it is the brave decision tonot follow that and to just
carve out your own path.
(36:07):
Maybe your path zigzags, maybeit's not, you know, like your
average thing, and that istotally okay.
There's no right or wrong wayto do it and you just have to,
like, go after what works foryou and just, I think, get
really in tune with what it isthat you want out of life.
You know what is it?
What are you?
(36:27):
Again, those personal goals areso, so, so important and should
be kind of your anchor foreverything 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 reallyfulfilling life.
So that's what I would say.
No, that's awesome.
It is true, Not everyone'sjourney, even to the same or
similar goal, is going to be thesame right.
Yours might zig and zag andmine might go just up and then
take a huge left turn right, andso that is so awesome.
Where can people connect withyou and where can they find your
(37:00):
podcast?
At?
Speaker 2 (37:02):
Yeah, so podcast is on all the podcast channels.
Just search Seed Money Jaylaand it'll pop up, and then
LinkedIn is the best spot toconnect with me.
I'm pretty active on there.
Speaker 1 (37:14):
Awesome.
Well, guys, that will be in theshow notes as well.
If you're watching on YouTube,it'll be in the video
description.
Make sure you guys go check outher show.
Make sure you guys check herout on LinkedIn.
But I just want to say, youknow, thank you so much for
taking the time out of your dayagain to you know, hop on and
drop so much knowledge ofbusiness and your experience of
business in such a cool, youknow, journey that you've been
(37:35):
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.
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