Ross O'Brien The Investment Biker

Episode Transcript

Speaker 1 (00:00):
Welcome to the Carolina Podcast Network. This week we sit
down with Ross O'Brien, the investment Biker.

Speaker 2 (00:05):
Erica DeLong here with Ross O'Brien the investment biker, which
everybody knows you as, but you're also the founder of
Art Moto Festival, which has grown to be this really
big deal and people were talking about it from all over.
But you are a serial entrepreneur, the go to person
with lots of nuggets of information for people like myself
and those listening where we're like, teach us, tell us

(00:26):
what to do in this life. Right.

Speaker 1 (00:28):
So welcome, Thank.

Speaker 2 (00:29):
You, Erica.

Speaker 1 (00:29):
It's great to be here. I really appreciate it and
I'm hoping to learn from you too. I'm kind of
new to Raleigh, so this is a new experience for
me too.

Speaker 2 (00:36):
Okay, So where did you migrate from? Welcome to North Carolina.
Are from me, Thank you, Molly.

Speaker 1 (00:41):
So I was in Florida before, okay, and then in
New York before that. So I'm what has been referred
to as a halfback, is that, right, people, which I
think is a term of endearment. But a New Yorker
that moves down to Florida and then half the way
back and stops enrolled.

Speaker 2 (00:54):
Okay, yes, I haven't heard it called that before. Like,
my husband's from Boston, so we call them a masshole.

Speaker 1 (00:59):
Okay.

Speaker 2 (01:00):
I'm the only actual North calen A native on my street.
So everybody's moving here, but we love it because you're
intelligent and bringing a lot of business to our area,
so we're appreciative.

Speaker 1 (01:09):
Well, I got to tell you, the community has been
just extraordinary. I'm so happy here and it's been almost
four years now, and I didn't know what to expect.
I actually moved here, never setting foot in Raleigh in
my entire life. So also, I have a business partner
who moved out here, and it was sort of after
the pandemic and things were shifting in my business and
had an opportunity to kind of be a little more virtual.

(01:29):
So I decided I would come up here. And one
of my employees actually moved out to Ashville. So my
first trip up here, I literally got on the back
of a motorcycle rode to Raleigh. That was my very
first time ever being here. I got my apartment just
sight unseen, went back incredible, picked up my dog, drove
out to Ashville to go visit my friend out there,
and then they lost my furniture, so I lived in

(01:51):
a hotel in Ashville my dog for three weeks before
I actually.

Speaker 2 (01:54):
Came here, which is not a bad thing. Ashville is incredible,
even as they are rebuilding from Hurricane Helen, which has
been like in the your mark. It's an incredible community
and it's beautiful and perfect for by riding.

Speaker 1 (02:04):
So it's world class. That's one of the things that
I've enjoyed the most about it. My partners enticed me
to come down to Florida because they said, oh, you
can ride your motorcycle every day, but they lied to
me because all the roads are flat and straight, all
the drivers are ninety years or older, and it rains
every day at two o'clock. So it's literally the worst
state for motorcyclic.

Speaker 2 (02:21):
Yeah, my in laws moved down there for the villages,
so the Bengo every day living their best life.

Speaker 1 (02:26):
Right.

Speaker 2 (02:26):
Okay, So now you're here in Raleigh and we've got
Art Moto Festival, which how many years.

Speaker 1 (02:31):
Now, so this is going to be our second year.
So we just started it last year.

Speaker 2 (02:35):
People are already talking about it like it's been around
for a decade. It's incredible how like the word got
out so quickly.

Speaker 1 (02:40):
It's it's crazy how it really took on a life
of its own. I was fortunate enough to be able
to start to really indulge in some of my passions
motorcycle motorcycling being one of them, and just wanted to
meet some more people in the community. I've really enjoyed
the people in Raleigh. I was blown away with the
world class artists musicians that we have here and just
really felt like this was a cool place and for me,

(03:01):
getting on the back of motorcycle is the best way
to go get to know somewhere, right. So I started
calling around and worked with the Landloader it's at Smoky Hollow,
and said, hey, I want to do an art motorcycle show.
That kind of just made it up and said, oh,
this would be something that I'd want to go to,
and got really connected with the community here where there
was a real gap there wasn't a big show that
was going on. We ended up having twenty twenty five

(03:24):
world class collector bikes there. We paired them all with
local artists. We auctioned off the art for charity. We
raised money for the Motorcycle Relief project that supports veterans
and first responders. We had like three thousand people show
up for our first event.

Speaker 2 (03:36):
That's so awesome.

Speaker 1 (03:37):
Became a really.

Speaker 2 (03:38):
Cool area that you're doing it in because that's new
and thriving, but a lot of people. That's a cool
spot for events.

Speaker 1 (03:43):
It was great and we actually outgrew it. So we're
doing it this year at Tobacco Road, which is the
Harley Davison. Yeah, it's going to be great. But it's
been a really fun way to get to meet the city.
I've gotten to know a lot of the guys in
the Motorcycle Police Union, become friends with them, and just
it's incredible all these people that are here. And it's
one of those things where as you said, I've been
an entrepreneur my whole life, and that's sort of entrepreneurial energy.

(04:05):
Is like, all right, well, if nobody's doing it, I
guess I'm the guy that's going to do it. Yeah,
And people have responded really positively to it.

Speaker 2 (04:10):
And there's going to be music obviously, all kinds of
things going on. It's family friendly. Where can people get tickets?

Speaker 1 (04:16):
Yes, family friendly music, all day art festival. We've got
some exotic cars coming as well, charity art Auction. You
find out all the information at artmoto dot com and
we're even raffling off a bike this year that people
can win too, So we kind of covered all the
bases and it's cool. We've got a whole team now.
Some people are super excited about it, so I'm hoping
that this will be the year I kind of get

(04:37):
to show up and enjoy it a little bit too.
But it's been an amazing experience.

Speaker 2 (04:41):
Well, as this is your baby, though, you're always going
to be like, Okay, it's all of this handled. That's
part of the deal when you're like the creator of.

Speaker 1 (04:47):
This well and that comes with its own dynamic too
as well.

Speaker 2 (04:49):
Right, And I'm excited, So I'll be there along with
my buddy e Why we're going to be m seeing
the event. So it's going to be really cool. Can't
wait to come out. My family's coming out, So it's
going to be a great day. But art Moto where
you get the tickets.

Speaker 1 (05:01):
Armotor dot com, the general admission is free, where we
have over one hundred vendors this year. It's going to
be in that entire street from the dealership all the
way around to the Weld and Halston. So we've got
face painting for the kids and we'll have some pumpkins there.
It's going to be a lot of fun.

Speaker 2 (05:18):
Yeah, Okay, talking about you, all right. So Ross O'Brien,
they call you a half back because you're down in Florida, back,
you know, to New York and back and now. But
you landed here in Raleigh and you are a you know,
serial entrepreneur. What advice do you have for people that
are looking to also become an entrepreneur?

Speaker 1 (05:35):
Yeah, great question. So I started my journey when I
was fourteen bussing tables in a restaurant at home in Canada,
so I'm actually from other places, not just New York
and Florida, and then opened a restaurant when I was nineteen.
It was just afflicted with this entrepreneurial energy ever since
then and started companies in technology space and digital media
and my venture capital fund that I started. I have
two funds that I've started invest in, largely in healthcare

(05:58):
and predominantly life sciences developed So it's been a bit
of a winding path and I think that's where I
would sort of start with advice for other entrepreneurs. Is
what you think it will be when you start is
not what it will be, right, And a lot of
it has to do with just being resilient. Right, the
amount of companies that I've had to shut down, the
amount of failures that I've had, the you know, financial
catastrophes for pursuing my dreams and my passions. Right, you

(06:20):
said earlier about our motive, it's like it's your baby,
You've fall in love with these things. But I learned
more from every one of those failures along the way
that over time becomes a creative to building, you know,
an approach to entrepreneurship that is I find unique to everyone.
So my job now is to find other entrepreneurs. And
I found a real sweet spot and working with entrepreneurs

(06:40):
who are sort of non traditional, right, So you don't
hear a lot of venture capitalists that are riding around
on motorcycles starting festivals. And there's a lot of founders
that I've had a lot of success with that are
either you know, veterans or people that don't normally have
the same pathways into you know, higher education, covered in tattoos, whatever.
None of that matters to us. It's really, you know,
do you have something important to say? Do you have

(07:00):
something that needs to be in the world that isn't
there already, and if you're uniquely positioned to do that,
we want to partner with you.

Speaker 2 (07:07):
What is the percentage where it's like companies end up
failing after a while, and you said you learn from
those failures. Some people give up because after what two years,
they don't necessarily succeed and so they just walk away.

Speaker 1 (07:16):
Yeah, I mean, I'm going to make up the numbers
right now, but it's something like seventy percent of businesses
don't make it past two years, you know, twenty five
percent past five. You know, my company's twelve years old now,
which puts us in that sort of rarefied error. But yeah,
it's it's very much about what are those obstacles that
are put in front of you, Which is why it's interesting,
It's why this analogy of motorcycling has become so important

(07:36):
to me at this stage of my career. I've written
some books on venture capital and been involved in trying
to be really of service to entrepreneurs and taught entrepreneurship.
And what I'm finding is that the things that I
learn on the road are very translatable to the things
that I had to learn the hard way through business
and entrepreneurship, meaning that it's not what you plan it
will be. I love this quote, no plan survives first

(07:58):
contact with the enemy. That we can have all these intentions,
but the reality is is we can't control what we
can't control. And so if you're willing to see beyond
those and recognize that these are not impediments to your
ultimate success, but rather you know, trials and tribulations to
developing a skill set and some tools in order to

(08:18):
do something that's really important. Resilience has become really one
of the number one factors that I look for in
the founders that I pack.

Speaker 2 (08:24):
I call it a pivot queen. So things right in
radio and I'm like, pivot queen, It's okay, we'll just
pivot and go this way. And that's not a problem.
Like you learn and keep moving.

Speaker 1 (08:32):
It's part of it. I mean, nobody told us that
you know, you're supposed to drop out of Harvard and go,
you know, start an app in Starbucks, You're going to
be a billionaire. Like that is so rare. The reality
is is that you know, there's this great book called
Burn the Business Plan that talks a lot about what
are the what are the characteristics of successful entrepreneurs And
it's not what you think it is. You know, the

(08:54):
average age of an entrepren a successful entrepreneur is actually
forty two. The average war experience of a successful entrepreneurs
that they've typically worked for someone else for ten years
before they've even started their own business. And these ideas,
that ideas matter. Right, Yes, you've got to have the
inception of something that is important that drives you, but

(09:16):
it's really about getting into those trenches. And you can't
predict what's going to happen. Nobody has a crystal ball, right,
So even as investors, I mean, a third of the
investments that we make are going to go to zero,
but that's the reality of the landscape that we're in.
Then the other third of those could be you know,
stratospheric in terms of their outcomes. That makes up for
all of the losses. But it's really about having some

(09:38):
perseverance and resilience. And I've found, despite how much I
enjoyed higher education and getting my MBA for me, there
is no substitute for just you know, blood, sweat, and
tears of being in the trenches, of working on things, the.

Speaker 2 (09:52):
Boots on the ground, getting your hands dirty, and pivoting
yes and pivoting. So I'm in the category of like
I want to one day. I've been doing radio since
I was an nineteen I've wanted to run a business
since I was I can't even remember. My husband's like,
you know how much work that takes, and I was like, yes,
but I don't know what I want to do. So
it's like I need I just want somebody to throw
an idea and then we can run with it, because

(10:13):
like I know, I could run it, but I don't
know the idea to start it. What do you have
to say for those people like you know you have
it in you, you just don't know where to start.

Speaker 1 (10:21):
I love, I love this conversation. So for me, it's
a bit of a spectrum, right, So I'll get to
the answer in a bit of a secutest way. But
the first thing for me is always starts with the idea.
Is interesting, but it's what Edison said, it's you know,
ten percent inspiration in ninety percent perspiration. So the ideas
kind of matter. But I'd rather back a founder with

(10:41):
a mediocre idea that's got a track record that can
be really successful operationally in execute. Right, then it's really
deciding what is your intention. Now, we use this term
entrepreneurship as if it's sort of all encapsulating, but really
there are all kinds of different forms of entrepreneurship. So
again going back to that book, I referenced the number
one indicator of whether an entrepreneur will be successful and

(11:03):
the type of business they choose is not what I
was surprised by. This is actually to buy and run
a franchise. So we don't think about owning a bunch
of subways as being entrepreneurial. Right. We get very caught
up in these oh I'm going to go start Twitter
or whatever it might be. But that is a sure
fire way to have independence and entrepreneurial success in your
career because you don't have to come up with the

(11:24):
idea for subway, you don't have to come up with
the systems, you don't have to come up with the brand.
You can really execute. So I always like to ask
the founders, like what is the purpose and the intention?
And for me, it kind of goes through a spectrum.
It's are you trying to generate wealth and create wealth.
Are you trying to create generational wealth? And that's not
a bad thing at all, But there are sometimes different
businesses than just hey, I want to be independent and

(11:45):
I want to run my own my own company. And
I will tell you the biggest fallacy for anybody going
in entrepreneurship to say, oh, I just want to be
my own boss is total. You know what, I have more.
You have to answer to a lot of people. I
have more bosses, I have investors. There's more accountability with
higher stakes being an entrepreneurship than there is just oh

(12:05):
I don't want to work for somebody else, So that's
usually a red flag for me.

Speaker 2 (12:09):
Me it would be generational welk, I would like to
create wealth for my family so that way my grandkids
can have a nice little place set in the backyard.
You know, I think about that. Do I go out
and buy a laundry mat? You know that's going to
create money or a.

Speaker 1 (12:20):
Car wash, And that's very entrepreneurial, right. It may not
be the same type of entrepreneurship that certain investors in
or certain things that other people do, but it doesn't
mean it doesn't have merit and the thing that always
gets lost in this conversation is founders lose sight of
the fact that your first investor is you. So they're
always talking to me, coming to me because we have
money that we can invest, right and that's the big

(12:42):
unlock for growing a company, And they lose sight of
the fact that they're the ones who took the risk
on themselves first. And it's usually friends and family and
it's you know, so you're if you made a choice
with your family and your husband say I want to
go do this, then you're making a decision to put
your time and resources behind something that's got higher risk
to it, you know, So you're taking the risk in

(13:02):
the business before you're asking anybody else to. So you
really need to think about it from that kind of
disciplined rigor of okay, does this have success and viability?

Speaker 2 (13:12):
You know.

Speaker 1 (13:12):
I've known people that have literally become billionaires by investing
in storage units you know too, and.

Speaker 2 (13:20):
Made the right choice, and now they're doing very well
and then creating more and more businesses because of the
money that came in from that. You know.

Speaker 1 (13:27):
As I said earlier, I'm from Canada originally, but I
choose to live in the us, because I have yet
to find any country that is more conducive for entrepreneurial
energy than it is here. And so I am actually
one of those people. I have a choice. I can
live sort of a lot of places. I choose to
be here because there's this incredible entrepreneurial energy. There's very

(13:48):
low barriers of entry to starting companies and filing an
LLC and all that, And there's a real economic vigor
behind creating sustainable you know, economics for you and your family.
And there's so many differ diferent businesses that you can
get into that, if executed well, can be highly successful
and achieve those goals. And if generational wealth is an objective,

(14:08):
a lot of people think about, Okay, do I ever
want to sell this business? Well? Maybe not, right? Am
I creating a cash flowing business? Like we all talk
about these IPOs and things like that. That's only one part
of our entire stack of the economy. And it's okay, Well,
do I want to build something that I can pass
along and bring my kids into the business one day
and then they can learn entrepreneurship and they can run it.

(14:30):
I think all of that is on the table here
and I firmly believe that, in particular in times of disruption,
which clearly we're in now and look I moved here
after pandemic, talk about massive disruption, there is always opportunity,
And I firmly believe that entrepreneurship is that innate talent
in people that can solve all of the world's problems.

Speaker 2 (14:52):
Okay, And then so when it comes to economy, the
highs and lows of our economy, obviously you say, just
go for it if you know you have it in
you and you can figure it out, Like it doesn't
matter what time or what we're dealing with here in
our world, Like, just go at it and figure it out.
Maybe it's the best time to purchase because.

Speaker 1 (15:07):
It's a low totally. I mean, I don't mean to
sound ignorant to you know, people that are going through
financial challenges and there's a lot of problems. But I
got my securities licenses and started working in finance right
after the two thousand and eight financial crisis. You know,
I raised my first fund right on the back of

(15:27):
that from really wealthy investors that I had relationships with.
And you know, there's always a way to uncorrelate your
strategy your business life from the macroeconomics and the macro trends,
and when things are not going well, that means that
something has to fill that gap. Great example is we
invest a ton in life sciences investing, so we do
a lot of our life sciences innovation, so we do

(15:49):
a lot of technology transfer with universities and spinouts, and
there's a complete uncertainty and stopping of funding for research.
Punchline is is we're seeing a lot of the wealthy
family offices, the people that have and the organizations that
are closest to some of these disease states so epilepsy
or autism or Alzheimer's are filling that gap, right, And

(16:14):
so we're finding new ways to say, okay, well if
that's not going to happen over there, and this was
the incumbent way we were doing it. Yes it's bad.
Yes it's going to be a real problem for advancing
science and a real problem for innovation. But that doesn't
mean that it stops. Because you know, who doesn't care
what's happening in the macroeconomy is Alzheimer's.

Speaker 2 (16:30):
It doesn't stop.

Speaker 1 (16:31):
It's agnostic to where we are, you know, culturally or economically.
So it really goes back to that conversation we just
had on perseverance and resilience, and it's that mindset of saying, Okay,
well this is the playing field that I've got a plan.
Is this too important to fail at? And if it is,
then I have found there's always a way to solve.

Speaker 2 (16:51):
Is there somebody that inspires you? Maybe you hit a
brick wall at times and your creativity feels flat. Is
there somebody that you turn to for inspiration or that's
been a mentor to you.

Speaker 1 (17:00):
Yeah, I mean not just one person. There's you know, individuals.
I have found a real solace in literature and reading
all kinds of and in particularly it's funny that you
just mentioned sort of creativity. So I've found a lot
of inspiration from creative people that you know. And you're
in the radio industry, so you know, I'm a huge

(17:21):
fan of like Tom Waits and you know, Bob Dylan
and these you know, classic songwriters, And I look at
that sort of the way in which they approach their
creativity was almost ignorant of sort of what was happening.
It's what they had to do. They had to do
their thing. So I get a lot of inspiration from that,
and then I'll dig in a lot too, you know,

(17:42):
what are their biographies and try to understand the people
behind them and to bring it back to motorcycling. That's
what I love about motorcycling as an artistic medium, not
just as a machine. It comes down to the artists
and the people behind it. So I think about entrepreneurship
then that same way as who are the people that
are driving this innovation? Who are the people that they
learned from? You know, we're all standing on the shoulders

(18:03):
of giants to use you know, these quotes, But there
is something deeper there when you get into the human
experience and the people behind it, whether it's art, creativity,
or entrepreneurship. So I didn't give you an answer in
terms of one person, but.

Speaker 2 (18:16):
It's collective, Like, yeah, you lean on a lot of people.
I do too, Like you know, there's a lot of people,
a lot of avenues that you go to to get
that inspiration or to get yourself out of that lull.

Speaker 1 (18:28):
And you know what I've found really interesting is as
time goes on, you can sometimes revisit some of those
assumptions and the thinking of younger you and maybe it
was flawed. I think that's one of the biggest things
that I see as kind of a gap and sort
of how you're approaching these and when when I was teaching,
et cetera, is this sort of reluctance to say, oh,

(18:49):
I made a mistake, right, So I've learned as much
from my mistakes, more from my mistakes than I did
from my failures, which I said earlier. That goes as
well for the people that inspire me, that that I follow,
that I try to learn from and try to absorb,
you know, from their success, because they do think success
leaves clues. And at a certain point, it's just having
this confidence or acceptance that hey, I'm not going to

(19:13):
get everything right, but that's okay. The best thinking we
have at this moment is the best thinking we have,
but it doesn't mean it's the best thinking tomorrow. And
then to be able to pivot, you see a word
from that and say, okay, well I can learn from
that and I can re imagine how I'm going to
think about these things going forward. So you know, whether
it's finding you know, spiritual literature or whether it's finding
entrepreneurial literature or creative literature. There are so many clues

(19:35):
in those things if we just put down our phones
and take some time to absorb what's happened prior to
us taking on these journeys.

Speaker 2 (19:43):
And community is always a big thing. I have found
like giving back to the community really adds to your
success and fulfillment and so art moto. The festival is
like a community event. How important is community to you? Oh?

Speaker 1 (19:56):
It's everything. I mean, this was the big transformation that
I experienced coming to Raleigh. I was just thrilled and
quite taken aback with how welcoming people were here. And yeah,
I love it. But there's a sincerity to it. Yeah right.
I didn't feel that in Florida for sure. And that

(20:18):
sincerity and that openness allowed me to be a little more,
you know, to unguarded in my you know, willingness to
just learn myself and learn a new place and learn
a new community. And I found so many communities here
that are doing so much for each other, in service
of each other and not in service of themselves. It's

(20:38):
almost this sort of like selflessness to it. So, yes,
we raised interesting last year. When we did. You mentioned
the hurricane in Nashville, We worked with Tobacco Road and
sent two tons of supplies out there right after the hurricane,
because it was October last year that we did the event,
and just pulled that together in a few weeks, because
we took the time to put our hand up and

(21:00):
say it's not about me. I'm not here to take
something from you. I'm not here to monetize something. I'm
not here. I'm here to do something so we can
all benefit from it. And in a matter of weeks
we pulled together two truckloads sent them out there. You know,
it's horrific, but this is these kinds of communities, whether
you ride motorcycles or not. I mean that that's there
for all of us to do. And I think this
is a great This is one of the big things

(21:22):
of why I think that the festival is becoming so
successful for us and we'll be so big this year,
is it's so diverse in its nature, the people that
we're bringing together, and that's what we want right now,
I think is and that's what I've found in Raleigh
is a place where I can show up as this
weird motorcycle loving you know Canadian and you know I, well,

(21:42):
maybe I'm trying to embrace the weird. I don't know,
but I think it's I think it's so wonderful to
see different communities come together, whether it's law enforcement, whether
it's minority communities, whether it's a creative community, and then
have this center point where we can celebrate not only
our differences, but the fact that we do enjoy living

(22:05):
in a creative, culturally diverse community. I couldn't see myself
being anywhere else at this point.

Speaker 2 (22:11):
Well, that's awesome. We're glad to have you. Artmoto dot com.
Come check out the festival. It's going to be amazing
second year now. And of course, where can people reach you,
the Investment Biker or Alsobrian, what's the best way for
somebody to reach out if they had questions?

Speaker 1 (22:26):
Yeah, thank you, Erica. And are we going to put
you on a motorcycle in the fourth Yeah, I'm down.

Speaker 2 (22:30):
For I actually want to purchased one probably, but then life.

Speaker 1 (22:33):
We've got plenty, We've got plenty of bring your helmets, Okay,
so yes, artmoto dot com for the festival. Come check
us out. It's free. Register for tickets, register to win
the bike, the Investment Biker. I do some publishing and
writing through the website just I biker dot VC Okay,
so I for Investment Biker, Ibiker dot VCVC for Bench

(22:55):
Capital h and we've moved some of that over to
our YouTube channel, which is just the Investment Biker Okay.

Speaker 2 (23:01):
Love it well, It was so great to sit down
with you.

Speaker 1 (23:03):
To this was a lot of fun. Thank you. I
really appreciate you having me. Thanks for listening to the
Carolina Podcast Network.