Mastermind Talks: Losing it All with a Family to Feed and a Quarter Million in Debt. How One Founder Bounced Back - with Jayson Gaignard

If you made 22 times the nation average income would you be 22 times happier than the average person? Today's guest did and he wasn't. After building a company to $6 million/year and losing it all in less than 18 months he learned that money and happiness scale very differently. He not only lost it all, he went a quarter million in debt all while having a wife and 6 month old at home.

Jayson Gaignard is the founder of Mastermind Talks, an annual invite only event designed for elite entrepreneurs. He started Mastermind Talks after a failed business left him a quarter million in debt and a ton of questions about what to do next.

In this interview Jayson shares how that experience completely shifted his perspective on what's important in life and business. HINT: it's not getting rich.

In This Interview You'll Learn...

  • why Jayson dropped out of high school
  • how he built a company to $6 million/year
  • how he lost it all and ended up a quarter million in debt
  • why making 22 times the national average income didn't make him 22 times happier
  • why his network is his most important assett
  • the difference between being rich and being wealth
  • how he built up a network of rockstar entrepreneurs


Show Notes

Podcast transcript:

Andy: Welcome everyone to another episode of Starting
from Nothing, the Foundation podcast where entrepreneurs share
with you how they built their businesses entirely from scratch.
Today, we have with us Jayson Gaignard on the show.
Jayson is the founder of Mastermind Talks, an annual invite-only
event designed for the elite entrepreneurs. He started Mastermind
Talks after a failed business left him with $250,000 in debt and a ton
of questions about what to do next. I asked him to come here and
share the story of how he answered those questions and why they
led him to connecting entrepreneurs with each other.
But more importantly than all of that stuff, sometimes you just meet
someone and you just vibe with them. You know, like, they’re just a
really good person and they just have this aliveness to them. I felt
that with Jayson ever since we started emailing back and forth. I
don’t know why dude but … it’s really cool. Thanks for coming,
Jayson: Well, I’m glad I was able to transcend that
through email.
Andy: Yeah. It’s crazy.
Jayson: I’m pumped, man. I’m really pumped.
Andy: I think part of it is coming … you came highly
recommended from a handful of people as well.
All right, dude. Mastermind Talks is absolutely incredible, but take
us back to the moment when you’re in 11th grade and tell us about
how you could possibly make the decision to drop out of high
Jayson: Well, I’ve always … I was always a terrible student. I
had a really strong work ethic ever since I was a small kid. Like the
typical entrepreneur journey, I had paper routes and I have snow
shoveling business up in Canada and stuff like that. I always had
that entrepreneurial bug. Around grade 11, yeah, I’m terrible student
and I came across a quote, “Never let your schooling interfere with
your education,” which is a quote by Mark Twain.
Andy: Yeah.
Jayson: I’ve kind of lived by that with most part. Honestly …
at the time, I was working … I had a part time job but I was working
40 hours a week through school. I would skip school sometimes a
week or two at a time just to work. Because I thought … I found
school to be rather pointless at the time. I made the decision. Yeah. I
was about grade 11 or early grade 12, to just leave. Maybe just … I
was terrible at Math, I was terrible at few things and I wasn’t getting
any better at it. I just kind of decide to jump in to the workforce to a
certain degree.
Andy: How do you make a decision like that that is so
against the grain, and I’m sure, most people on your life are like,
“You’re crazy. What are you thinking? What are you doing?” but
I’m sure you felt there’s truth. You’re just, like, this is the path for
me. How were you able to stick through that?
The reason I ask this question is … because there’s a lot of people
listening who feel like they’re alone. They might be a first-time
entrepreneur; nobody else in their family is one. They know they
want to do something but everyone else seems like they’re pulling
against them. How do you know when you have that truth that you
have to follow it?
Jayson: Well, initially I didn’t know. All I knew is I wasn’t a
good fit for school. I didn’t decide to start a business right out of
high school, initially, even though I had those kind of
entrepreneurial traits; when I was younger. I became actually like a
car mechanic. I love cars at the time and I became automotive
performance mechanic so I kind of pursued my passion that way.
Andy: Yeah.
Jayson: What happened one day, oddly enough, was … I was
satisfied with what I was doing. I wasn’t making a ton of money
financially but I remember calculating the average lifespan of a
Canadian male which was 81 years or some like that and I multiply
that by 365 days.
Andy: Yeah.
Jayson: I took my age at the time and multiplied that by 365
days, and when I found out that basically I lived 6500 days out of
the 28,000-year allotted, in essence if you live a full life expectancy.
Andy: Oh, man.
Jayson: It really created a sense of urgency … which I never
thought before. Because when you’re 17, 18, when you think of 80
years from now or 60 years from now, it’s so far away.
Andy: Yeah.
Jayson: Think of your life in a prospective of days, it was an
eye-opener for me and I quit that day because I knew I was not
going to … that path I was on, I was not going to kind of change the
world per se. That was actually where I really made that decision
and then I got into … car sales for a month because I was never
without work. I started business right out after that.
Andy: Cool. Tell me about the business you started.
Jayson: First one was a personal concierge business. I was in
car sales; I did that for a month. I was pretty successful. I was pretty
good at sales. But what happened was, one day an entrepreneur
came in to buy a car. Oddly enough … owned a very successful
business and … he took three days of work to buy a car. I’m, like,
the money doesn’t make sense, right? He was just one of those
people who was driven on getting a deal. The amount of time that
was taking him to search for the deal was not worth it but he wanted
a deal. In theory, you could pay somebody to do that car shopping
for you, and probably get you a better deal based on their network. I
decide to start a shopping business and then that kind of transformed
into a personal concierge business which was a budding industry at
the time.
Andy: Did you tell him about the idea?
Jayson: No. Actually, after I sold him the car, I thought about
it over the past three days. When you’re in car sales, there’s a lot of
down time. You have to call opportunity, think about things.
After that, I kind of came up with that thing. One of our
philosophies for the business was, if it was legal and moral it would
save you time; we take care of it. We decide to do a ton of the
different stuff. I dress up in a tux. Every time people would see me,
stuff like that. It was a good business. It was a good business in the
sense that I was young at the time and it was a new industry. It was
a nice angle for media. I was able to get a lot of media attention.
Andy: Oh, wow.
Jayson: Because of that. Because of my age at the time and it
was a budding industry. They were looking to cover somebody in
that industry so it was a nice angle. That worked out. But I learned
quickly that press doesn’t equal profits all the time. It didn’t do
much for my bank account and then … Because we had that
philosophy that it feels legal and moral and would save you time, we
take care of it. A lot of people, when they thought of the word
concierge from a position perspective, they thought of hotel
Andy: Yeah.
Jayson: When they thought of a hotel concierge, they thought
of concert tickets. So people started coming to us for concert tickets
and wed’ always …
Andy: Hold on. Hold on. Hold on. Before we get in to the
transition, I want to go back to …
Jayson: Sure.
Andy: When you had the idea.
Jayson: Yeah.
Andy: So, this guy comes in, you’ve got all this down time.
You’re like, “Oh, I’m going to start this concierge business or this
personal service business.” What did you do after that?
Jayson: After that … so I started that business and I got a part
time job selling car parts, oddly enough. I was doing those both at
the same time. So, I was building up the business and I was doing
the car part stuff and it was a hell of a balance.
Andy: Who is the first person you reached out to? Where
did you get your fist customer from? For that business.
Jayson: For that business? Honestly, it was my accountant.
The guy who likes to have my business and stuff was my first
customer. Honestly, till this day, if I didn’t have him initially, I
probably would have quit.
Andy: How did you get him as a customer?
Jayson: I was looking to kind of open up a business, to
actually register the business and somebody referred me to him and
I met with him. He just became a friend who just started using me
for certain things. Like basic errands and stuff like that.
Andy: Yeah.
Jayson: Yeah, but I did all kinds of stuff that were failed
attempts at marketing. I remember once I created these fortune
cookies with a message inside and I delivered them at Christmas, by
hand, to a thousand houses …
Andy: What?
Jayson: Didn’t get a single call.
Andy: Wait, wait.
Jayson: There’s a bunch of stuff I did which fell flat on
its face.
Andy: Okay. This is really cool. I love hearing the story
because it’s … anyone could do this. I think a lot of times people
think they need some crazy business idea or something that’s
revolutionary. You’re just solving problems for people. You know?
Jayson: Yeah. Absolutely. As we became … a society busier,
we want to offload a lot of this kind of stuff; those errands and that
kind of stuff. That’s why the business model made sense …
Andy: Yeah.
Jayson: … but I was not passionate about it at all.
Andy: How did you charge?
Jayson: It was on hourly basis. We charge … I think it
was $60 an hour.
Andy: Mm-hmm.
Jayson: And then they could buy a package of time and stuff
like that. Yes, that was kind of the format of it. Because of that, it’s
extremely hard business to scale … the human capital, right? I hate
dealing with …
Andy: (Laughs)
Jayson: I hate employees with a passion. Yeah.
Andy: This is super fascinating.
So, your first employee was the accountant, where did … at what
point … How big did this business grow to?
Jayson: Well, I was still … one of the interesting parts of it,
which may be a benefit to your audience is I was working part time,
like 25, 30 hours a week and then I was working on the business. I
was still barely making ends meet. And at the time I’m like, you
know what, I should start a third business or a second business in
essence. In essence, did do three things in order to make more
Andy: Yeah.
Jayson: I run remember thinking to myself I’m like, that’s
ridiculous. I already have a perfectly good business. If I actually
focus on it, something … it should go off. It should go well.
So, I quit the part time job which was scary at the time and then
after that our sales went from $5,000 a month to 8,000 to 12,000, to
20,000, 30,000. Every month, month after month for four years,
they went up.
Andy: This concierge business.
Jayson: Yeah. After a few months, it pivoted into the ticketing
business which is where we really start to make money.
Andy: Yeah.
Jayson: But taking that step … and actually I’m a firm
believer of where focus goes, energy flows.
Andy: Yeah.
Jayson: If you’re able to focus 100% on your business, you’ll
find a way. You’ll find a way. I experience that first hand, it was
tough to do; tough decision to make to leave that part time income
which was secure, to start a business full time. [I set one up
00:10:51] month after month.
Andy: When you decided to leave that business, how much
money were you making in the concierge business?
Jayson: We’re doing probably $5,000 in revenue so we’re
probably … I was probably netting 12, 1500 bucks a month; at the
time. Wasn’t enormous but I was living very lean. I was living like a
bachelor apartment and that’s all I got.
Andy: SpaghettiOs.
Jayson: I was fasting a lot … (Laughs)
Andy: (Laughs)
That’s a really tough decision, you know? I think a lot of people
struggle with when is the right time, do I pull the trigger and pursue
something full time. I think there’s a big lesson in having the model
figured out. It sounded like you had the model figured out in terms
of getting people on board and making money, you should need
more time and energy to scale it.
Jayson: For sure. Yeah. The biggest thing now is the piece of
advice I give to anybody is just surround yourself with other people
who’ve done it. Afterwards, I had mentors come along who really
change my mindset around certain things that were game changers
for my business. Initially, if I know somebody who wants to get into
business and they’re serious about getting to business, their main
focus should be hanging around other entrepreneurs or other people
who are trying to get into business as well.
Andy: Yup.
Jayson: That’s by far. I never had access to that and who
knows if I didn’t take the plunge where I’d be. Yeah, that’s the first
biggest thing now. What I would have done different, or piece of
advice I give myself back then would be … yeah, just seek other
people. And there was no back then or anything like
that, there’s a much more … it’s much more of community you can
kind of join and they’re easy to find and that kind of stuff.
Andy: Oh, this is going to be fun. I can’t wait to … We’re
going to … I want to hear more about the ticket business and then I
want to hear about … You’re probably one of … assuming, one of
the most connected people around and I want to hear about how you
got to that point, especially when you started without anyone to
really help you.
Jayson: Yeah.
Andy: Let’s talk about how … how do you make the shift
into … getting into ticket sales?
Jayson: Well, one of the interesting things was … Well, I
guess first one of the points was that I was kind of following the
money to some degree. Because most of our sales started becoming
from the ticket side of the business so I started to kind of just do
more and more in that; after awhile became kind of evident.
It’s funny because just talking about this, I remember … I was
featured … somebody was featured in a magazine, a really
prominent local magazine on how to get money from the
government. I reached out to him and I said, “Hey, I don’t know if
this applies to my business but I love to chat,” and he brush me off.
He’s like, “I don’t have time to talk. It doesn’t apply.” I’m like,
“Okay. Fine.” The following month, I was featured in that same
magazine on like a four-page spread. This guy saw it and he’s like,
“I remember you trying to contact me last month. Do you want to do
dinner?” We did dinner and he became, in essence, my first mentor.
Initially, I remember we’re doing maybe 10, 15,000 dollars a month
and he’s like, “Picture a day when you’re doing a $100,000 in a
month,” or something like that. I’m like, that’s impossible. That’s
where other people’s business is. I could not ask that number of any
I forgot about that for a few years until one month we may … we’re
starting to do, like, consistently five, 600,000 dollars a month and
I’m like, shit! I remember the days when 80, 100,000 dollars a
month was like … so far beyond my grasp that … it was funny to
think. But in essence, he was one of the core people who kind of
push me and said, “Listen, you have the ticket side of things going
really well. You should focus on that.” I was married to the other
side of the business. I like the aspect to the other business. At least I
thought at the time. I was very naïve and stuff like that that’s why
mentors are … I attest a lot of my success to … surrounding myself
with the right people.
Andy: Yeah.
Jayson: But that eventually became such a big aspect side of
the business that people just kept on coming to us for tickets so then
we pivoted and became a ticket kind of wholesaler in essence.
Andy: Beautiful. How old were you when you started this
Jayson: So, I would have started that concierge business
initially when I was 18 and then probably pivoted when I was about
19, 20.
Andy: Okay. So, 18 … say, a year of doing the concierge
stuff. In a year, how big did the business grow to?
Jayson: It wasn’t huge. I think we’re maybe doing … it was
probably doing $30,000 a month; 25, 30,000 a month. I had one
employee. I had a hard time hiring people because everybody had to
hire or would have hired were older than me. That was a really
tough thing for me; really tough pill to swallow. In hindsight, it
didn’t grow as fast as it should have. There’s a ton of things I did
wrong but I guess … yeah, I guess the figure would probably be
around $30,000 a month.
Andy: But 30 grand a month as a 19-year old is a lot of
Jayson: Yeah. That would be revenue. I think I’d probably be
bringing home. I do bring home a comfortable salary of maybe four
grand a month; three, four grand a month.
Andy: Yeah.
Jayson: Yeah. Yeah. But it was a service-base initially.
Literally, I was on-call 24/7 for stuff. I did crazy stuff in that
business. I broke up with people’s girlfriends for them.
Andy: What?
Jayson: … crazy stuff. Yeah. It was cool [inaudible
00:16:41] but you’re always on call.
Andy: Tell me the story of breaking up with someone’s
Jayson: I had a customer once who basically dating a girl and
he said, “I need you to pick up a box and deliver her this box and
say I don’t want to be with her anymore.” I’m like, “All right, dude.
Whatever. As long as you paid me my 60 bucks an hour.” So, I
ended up … yeah, grabbing the box, going to this girl’s house. She
open the door, I was there in a tux, holding this box with her stuff.
Andy: Oh God.
Jayson: Unfortunately … I forgot the customer’s name,
“Unfortunately, Joe doesn’t think it’s going to go on any further.”
He gave me a little script and I just handed her the box and she’s
like, “Okay.”
We got in all kinds of crazy, crazy stuff. Even like watered … I
watered trees and I’d be dressed in a tux. Literally. I was nuts, dude.
Andy: Dude, this is brilliant. I love hearing the story
because it’s … it doesn’t take … you didn’t have any business
background or crazy marketing knowledge. You’re just doing what
was different and fun, it sounds like.
Jayson: Yeah. No, I was very … I’ll tell you one of the best
lessons I learned in regards to marketing was probably actually
when I was about ten, 11; when I started this lawn cutting business
and snow shoveling business. I’ve printed all these fliers; probably
500 fliers, deliver them … I delivered probably 420 of them. Never
got a response. It was just, like, we’re doing lawn cutting or
whatever the case may be. Feel free to give us a call. It ought to kind
of look very professional and polished.
Andy: Yup.
Jayson: And then the [inaudible 00:18:19], it’s not working.
What am I going to do? I’m just going to write, “Listen, I’m a 12-
year old guy. I’m trying to … just make some extra money,” blah,
blah, blah. I wrote a handwritten message in each one of these and I
handed out the last 80 and I got literally … there was like … it was
a 35% response rate. Because that openness and that vulnerability
that’s kind of tied around. Then a lot of people, when they start a
business, they always want that persona that they’re big and stuff
like …
Andy: Yeah.
Jayson: Right? Where … a lot of people don’t connect with
that. One of the things that resonates with me all the time, by far,
one of the most impactful quotes that I can think of when it comes
to marketing which is from 22 [inaudible 00:18:59] loss of
marketing …
Andy: Yup.
Jayson: Is what works in the military, works a marketing and
that’s the unexpected. Everybody is getting bombarded with
advertising with services and everybody’s trying to look
professional and played this game but you can breakthrough that
clutter by being open and vulnerable. People are genuinely willing
to help.
Andy: Yeah.
Jayson: That was kind of one thing.
One lesson I learned originally is that when you’re starting out,
you’re always trying to have that persona, not be yourself. I’ve
learned especially when I ended up in a bad financial situation last
year that vulnerability is huge, kind of that transparency … it’s
incredible. Definitely from starting from scratch, that’s kind of the
theme is definitely … kind of embrace that vulnerability and then
don’t be afraid of it because people will respond to it.
Andy: At some level, it’s your greatest asset.
Jayson: Absolutely.
Andy: I think we make business too complex at times. And
we get rid of like … the entire purpose of business is to just solve
problems and help people.
Jayson: Yeah.
Andy: I think we forget that.
Jayson: Yeah. No. Absolutely. Totally right, dude.
Andy: Okay. Nineteen years old, 20 years old, you start
making the pivot, start making the switch into selling tickets.
Jayson: Yeah.
Andy: What happens when you start making that switch?
Jayson: Well, we slowly … Just given the business model, we
were growing … pretty quickly financially. Like our financial
revenues. And we kept a small team. Because it’s just the model of
the business, we had a team of two, three people. Within no time we
were doing a million, a million and a half. That was kind of a nice
Andy: So, a million, a million and a half with two or three
Jayson: Yeah. What we were doing is we were wholesalers.
There’s two different aspects of the ticket business. There’s the
retailers which should be like the StubHubs and the eBays and stuff
like that. And then there’s wholesalers who provide the tickets. We
would buy tickets in bulk and then resell them through 4,000
affiliate sites including the StubHubs and the eBays and that kind of
stuff. So we were able to have a really small team and do huge
figures of revenue.
Andy: What are your margins on that?
Jayson: Usually about 20, 20 to 23 percent; especially
back then.
Andy: Yeah.
Jayson: Yeah, it was a good time.
It is funny though. One of the lessons I learned there was that … we
were doing … let’s say we’re doing a million and a half and we’d be
running it like … we’d net 300 grand or something like that. In
business, you always want to keep ramping up and ramping up and
then we do 3 million, so double in revenue but our profit will be 350
grand. All that effort was not worth it. You know what I mean? I’ve
changed my mindset quite a bit in business that … You have to
understand where that sweet spot is in your business. A lot of times,
it’s not worth that extra effort to go big. Just to kind of impress
people with numbers and stuff like that.
Andy: Yeah.
Jayson: You never know. It’s funny, my buddy James
Altucher told me something recently. He’s like, “You never know
somebody’s net worth until they go bankrupt.
Andy: (Laughs)
Jayson: It’s true, right? You can have $50,000 … or you can
have $100,000 a year business but you net a $100,000 …
Andy: Yeah.
Jayson: Or you have a $10 million business and you can be in
debt. Understanding that sweet spot in your businesses is a good
thing and being content when you reach it is not a bad thing. Which
is kind of counterintuitive to how business is; you always want to
grow it, that kind of stuff.
Andy: Wow. How big do this ticket business end up
Jayson: In the end we were doing about $6 million a year so
that was after, about four years with no outside investment. We
always just pour the money back into the business constantly.
Andy: Wow.
Jayson: (Crosstalk).
Andy: Twenty-two, 23.
Jayson: Yeah. I was about … yeah, about 20 … 23.
Yeah, 23, 24; roughly around there.
Andy: Wow. $6 million business. Then what happened?
Jayson: I was “living the whole life 4-Hour
Workweek.” I read Tim’s book. (Laughs)
Andy: Yeah.
Jayson: I guess 2008, 2009. I was living a good life. I had a
really small team at the time and was travelling the world. But with
all these money and all these free time, I was forced to answer some
tough questions like why am I here? Will I be remembered? How
many people will show up to my funeral? That’s been something
that’s kind of driven me constantly is how many people will show
up to my funeral. Because you got billion dollars in the bank and
your wife doesn’t even show up to your funeral, and that happens.
You know what I mean?
Andy: Yeah.
Jayson: Or you can be broke but have made an incredible
impact in the community. I’m always a firm believer that the true
measure of somebody’s … the quality of somebody’s life or their
impact is how many people show up to their funeral.
So at the time, I didn’t like the answers I was giving myself. They
were not the answers I wanted per se. I came to the conclusion that
that year … I meet 22 times a national average income. It’s funny,
even though I was terrible at math, I did these all kinds of … these
populations that were game changers for me but … I realize I made
22 times a national average income. Now, it’s bothersome because I
realize I was not 22 times happier than the average male. I was not
22 times healthier. Two years prior, when I was 22, I had kidney
complications because of stress.
Andy: Wow.
Jayson: I found out kind of the hard way to some degree that
money and happiness scale very differently and really kind of
shifted my mindset. At the time … there was actually one time
where I didn’t have good mentors around me so I started to see
money as a source of pain. Consciously, I want to sell the business,
subconsciously, I started to sabotage it.
A few other things happened in and around then. One thing was is
that I knew that business was not going to be my last business or my
claim to fame. What I decide to do was take a lot of my money at
the time and reinvest it in the business and use it as a learning
platform and run under the model that conventional methods yield
conventional results. So, we were going to do stuff in our industry
that nobody else has ever done and either was going to work out
famously or was going to crash and burn. I was totally fine with it
because I knew I could kind of bounce back.
Andy: Yeah.
Jayson: What happened was we kind of tripled in staff
overnight, we opened two retail stores which nobody in that industry
does; everything’s online. We were kind of off to the races. One of
the things that happened was … the business grew faster than my
skill set. I’ve always been terrible in managing people.
Andy: Yup.
Jayson: It doesn’t mean I’ll be terrible forever but at least at
that time I was really bad at managing people and I had some bad
hires in the business. As I’ve started dealing with my own personal
issues and disconnecting from the business, these bad hires were
like a cancer and basically started killing the business. I was so
disconnected from it I didn’t care. They could drive it into the
ground; I didn’t want anything to do with it.
Andy: Yeah.
Jayson: I came to the realization that … when I was kind of
sabotaging it that I was totally cool with landing the business at
zero. Because if I landed at zero, I can start something new, it was
not a big deal. So we are going downwards, making that landing to
zero and then two things happened: one is that … as a business, at
least in that industry, we used to put a lot of things on credit cards.
One of the things you learn in business, you hear this from a lot of
experienced entrepreneurs, is extend credit whenever you can.
When business is good, extend as much credit as you can for rainy
Andy: Yeah.
Jayson: That’s something I never did. I heard it and I
understood it but I never did it. What happened was I used to put a
half a million dollars a month on one particular credit card company
and I kind of put all my eggs in one basket and I was good customer
of theirs for five months and all of a sudden they put my card on
hold. Almost like as a test for me to pay off the card. Usually, it
wasn’t a problem because the way the business model work is we’d
buy inventory and we’d sell it at the same time so we’d pay off
the credit card, it was just this money machine.
Andy: Yeah.
Jayson: When they did that, I put a little hiccup in that money
machine and I’m like, “You know what? I’ll figure it out. Not a big
deal. I’ve been through worst.” But then a week later, I got a call
from my merchant services provider and they said … they had a
reserve account. They consider my business to be medium risk so
they were holding a $100,000 of my money in a reserve account that
… in case went bankrupt or closed up shop overnight, they could
protect themselves or chargebacks.
Andy: Yup.
Jayson: This guy called on a Friday afternoon and he’s like,
“I’m just calling. Unfortunately, we assessed your account wrong,
initially, and we need to take more money for reserve accounts. So,
because of that, we have to put your account on a 100% reserve.”
Basically, eliminating my cash flow. Ninety-eight percent of my
business was credit card transactions and they were stopping that
overnight. Everything that I charge for … on credit cards, was going
into a reserve account and I could not touch it.
I remember the call with the guy because I’m like, “Listen dude, I
hope to God you’re trying to use me as an example because … I’ve
been through stuff in business before but if this happened to me two,
three years ago, I probably hang myself in the garage. You’re
cutting cash flow for a business where I have employees who I have
mouths to feed, I have a lease or leases and stuff like that.” He was
like, “Oh, no. We do this from time to time but I totally understand.”
I’m like, “No, no. You don’t understand. At 5:00 today, you can
disconnect from your work and get on with your family and that
kind of stuff.” I’m like … Monday was a holiday and I’m like, “Do
you know what a holiday is for an entrepreneur? It’s a work day
with no meetings.
Andy: Yeah.
Jayson: You don’t know what entrepreneurship is all about.”
That lasted for about five, six weeks where the cash flow stopped. I
was getting married at the time, I had a six-month old daughter and I
was literally … a couple of days away from completely being bonedry.
Like completely, completely.
What I did … which actually may be a benefit to your listeners is
that … So, I was dealing with a big bank. Every time I reach out to
them, they say, “Can’t do anything. Sorry. Can’t do anything.
Sorry.” Now, I was always dealing with the lower level guy.
Andy: Yeah.
Jayson: I’m like, how am I going to be able to crack this
business because I’m not getting past them. What I did was I found
out the email structure for the bank which was first name dot last
name, and then I created … Then I looked at everybody
who’s on the board of directors for the bank; everybody who’s the
top customer service person, who’s the Ombudsman for the bank,
who’s in the PR team. I emailed the guy and I CC’d everybody else
at the top level of the bank. In its title email I said, “XYZ bank is six
days away from making me bankrupt.” Because I was trying to
think of a copy title that would look good as like a news article or
some like that.
Andy: Oh, beautiful.
Jayson: … kind of give them that impression.
Andy: Yeah.
Jayson: In the letter or in the email, I just said, “Here’s the
facts,” you know what I mean? And I was not threatening at all. The
only thing I did say in the email as that … this is an opportunity for
your bank to be proactive instead of reactive because I’m not just
going to … let you guys going to do this to me and … whatever.
You’d have to kind of work it out. Then I got an answer within two
Andy: Wow!
Jayson: Because at first, initially, the guy I emailed, who I
was dealing with time and time again who was not giving me any
kind of leeway was like, he saw everybody who was CC’d above
Andy: Yeah.
Jayson: So it was like, “Fuck! I got to act on this right away.
So I don’t know [inaudible 00:30:43].”
Andy: (Crosstalk)
Jayson: But, he’s like … he started acting on it right away. A
supervisor got back to me, somebody … and the Ombudsman is
like, “If this doesn’t get resolved, let me know and I’ll deal with it.”
Then I got literally … some of the funds released after 48 hours
which was huge.
Andy: Yeah.
Jayson: But by then the damage was done and I was a quarter
million dollars in cash debt. There was a couple of weeks left of the
business in essence and it kind of wind out and then I “hit rock
bottom” to a certain degree.
Andy: Did that cause the business to fold?
Jayson: No. Like I said, I was totally fine at ending at zero so
I was kind of folding the business myself.
Andy: Yeah.
Jayson: What that did was put me a quarter million dollars in
cash debt because it eliminated … I couldn’t pay off credit card so
damage my credit.
Andy: Yeah.
Jayson: What happens when they put your money in the
reserve account, at least in Canada is … the only way you can get
that money is by closing that merchant services account and then
you have to wait six months.
Andy: Yup.
Jayson: And then they release it. The damage that happened
over that six months, I would have landed comfortably at zero, that
put me deep in the hole financially.
Andy: Oh, man.
Jayson: Yeah.
Andy: Merchant services … it’s just a completely messed
up industry. It’s so terrible.
Jayson: Yeah. We did.
Andy: We had some really big issues with them too. It’s
Jayson: Yeah. It’s interesting. Yeah. I don’t know … Too
many other providers at least in Canada and stuff like that but I
haven’t had a great dealings with them. And we had a track record
with them, like five years. We’re doing millions in a year. Hardly
any charge backs and that kind of stuff. It was just one person, one
service wrap or some like that, decide to put a big reserve and just
completely crush the business.
Andy: Wow. Oh man! So, that happens. You hit rock
bottom. Where do you go from there?
Jayson: That was one of the scariest parts in my life for two
reasons. One is that when you go from having a business that’s
doing half a million dollars a month in cash flow.
Andy: Yeah.
Jayson: And then that stopping. Anybody in business knows
that cash flow … a cash flow, if that stops, new business is a heart
attack and profits is like a cancer. You can fine tune it over time. As
long as you had cash flow, you can keep the business going.
Andy: Yeah.
Jayson: When I hit rock bottom, I had no cash flow coming in,
whatsoever. Like, zero. And being used $500,000, a million dollars
a month going through initially, that was a tough pill to swallow.
The second thing was … is that I remember getting back from
getting married and thinking to myself like, I knew mentally I had
what it took to pull myself out but I didn’t have the energy to
support myself. I didn’t have the energy to do it because with all its
added pressure because of all the debt and not being in business
anymore, it just took a toll on my health. That was the scary part of
my life because it was like having a Ferrari of a brand but no gas in
the tank.
Andy: Yeah.
Jayson: The first thing I had to do was get my health back on
track and get my energy up because you can’t do anything if you
don’t have the energy to support you.
I started kind of focusing on that, started waking up at 4:00 in the
morning to work and I became really, really structured as …
become very, very productive, very structured as how I run my days
and stuff like that, which was a real game changer for me.
How that kind of led into my business because initially I didn’t
know what I was going to do next, is about a month … so this
happened in August of last year, August of 2012. In October …
September, October, somebody gave me a ticket to go see Seth
Godin in New York. I’ve always been a huge fan of Seth but never
had the opportunity to actually see him in person.
At this little intimate seminar that he did, he was talking about the
most successful sales person he knows. I don’t want to botch the
story but in essence, what this sales person does is he kind of
connects his clients and he’s basically kind of trying to show that
the … there’s huge value in being the catalyst connecting other like-
minded individuals.
Andy: Yeah.
Jayson: When I heard about that I’m like there’s no group
more disconnected than entrepreneurs, right? Because they’re just
always working in their business, very rarely are they getting out. In
the tech scene, it’s a little more … they’re much more sociable than
kind of, I guess, traditional business which I’m used to.
Andy: Yeah.
Jayson: But, I’m like, there’s definitely something I want to
do here.
I decide to do these things called Mastermind dinners where I’d
invite 68 entrepreneurs who didn’t know each other and I just kind
of facilitate connecting them. Initially, the first one I did, I almost
canceled it two hours prior because I’m like, nobody’s going to see
value in this; they’re going to think I wasted their time; this kind of
stuff. And then …
Andy: Who is coming to the first one?
Jayson: Sorry?
Andy: Was anyone coming to the first one that our listeners
would know of?
Jayson: No. There are more … That particular group, now I
have more high-profile people but … I mean, that particular group
was more kind of local entrepreneurs.
Andy: Yup.
Jayson: No software or any tech guys in that particular one.
Like the one last night it was much more high-profile. Yeah. No,
regardless, I value people’s time immensely. So, whether they’re big
name entrepreneurs or not, I want to deliver every time.
Andy: Yeah.
Jayson: I just felt like they wouldn’t see value in it and they
think I wasted their time.
And ended up … I remember we did the intros and then … the first
15 minutes, one guy turned to another and so like, “You and I need
to talk.” They were pumped that they knew each other or they met
each other at this dinner. I just felt this instant kind of rush of energy
and clarity that this is something I want to do for a long period of
time. If not, the rest of my life.
The first dinner went off without a hitch. Literally, there’s no
facilitation needed. It went on for four and a half hours. It was great.
I started doing these dinners every week and I would pay for the
dinner. I was quarter million dollars in cash debt. I had very little
credit left and I was paying for these dinners; they are five, 600
dollars a dinner. But I just saw so much value being created. I didn’t
have a business at the time that was in alignment. I wasn’t
benefitting from it financially and I couldn’t see how I was but I
said, by connecting these people, I’ll get value some way somehow.
What happened was … I’ve been friends with Tim Ferriss for … or
I’ve known Tim Ferriss for probably about two and a half years and
I have an opportunity doing an event with him. I pulled the trigger
on that, I’m like … well, here’s my opportunity to do what I do in
these dinners but on the larger scale. Instead of having eight people
I’ll have 80 people or 100 people. That’s how Mastermind Talks
came to be.
Andy: Wow. You almost went through the phase of starting
from scratch all over again, like …
Jayson: Oh, absolutely. That was below starting from
Andy: Yeah. It’s actually even worst.
Jayson: Yes. (Laughs)
Andy: [Inaudible 00:38:02] … sounds awful. [Inaudible
00:38:07] I’m saying.
Jayson: One thing. One thing that I was telling myself at the
time, just going to give your listeners some prospective is that …
when I had nothing. I had nothing. I didn’t know if my car was
going to get repossessed, that kind of stuff. I said … I started really
investing my network because I said to my … time I’m like, the
bank can take my house, they can take my car but they can’t take
my network.
Andy: Yeah.
Jayson: That’s why I really started to focus on my network
more than ever and delivering value to people and stuff like that
because I knew they could take everything else but they couldn’t
take that. My network is what pulled me out, by far. I just …
through the matters, you never know the value of your network till
you really need it.
Andy: Yeah.
Jayson: I’ve been investing in my network to some capacity
for the past three years and when I needed it people stepped up. Or
at least the real people stepped up and it was …
Andy: Yeah.
Jayson: … a test. That’s what really pulled me up.
But yeah, in essence, I started from scratch again and I had all those
fears everybody has: the fear of rejection from customers or the fear
of failure and that kind of stuff. I remember when I was planning the
event, some people knew, some people didn’t. I had a landing page
where I had the website already up and running. I was going to
launch it on Facebook to tell everybody what I was up to. I
procrastinated on that for eight days. If I put this out there and it
doesn’t work out then people are going to judge me.
Andy: Yup.
Jayson: I was already successful in business but I had all these
fears come back and it was interesting.
Andy: Yeah.
Jayson: It was really interesting. In essence, yeah, I started
from scratch again last year.
Andy: If I was a quarter million dollars in debt and you’ve
got a wife and little girl, why an event like … that seems like it’s not
going to get you to the position where you need to be.
Jayson: No, not at all and that’s the thing. My wife, a God
lover, my wife knew that I would not do anything out of money
Andy: Yeah.
Jayson: That’s why I got [inaudible 00:40:09] last business
because it was not in alignment with who I was or who I want to be.
She knew deep down … I rather live in a shelter and do what I want.
Andy: Yeah.
Jayson: Than just either work for somebody else; which was
scary too because you’re hitting rock bottom and you’re an
entrepreneur, you realize you’re unemployable. You cannot work
for somebody else.
Andy: Totally.
Jayson: I could not grasp working for somebody else. I’d
rather have a bullet between the eyes. That was kind of a scary thing
as well. Yeah. That was kind of [ahead 00:40:39] at the time.
Andy: Yeah. You’re doing this because this is your highest
value thing that you can add to the world, is the way it sounds.
Jayson: Yeah. What we talked about before getting on air here
is that … I had a conversation with somebody last night. I’m like,
you can be rich or you can be wealthy, right? You can pursue, create
online product launches and stuff like that just to make a buck.
Andy: Yeah.
Jayson: You can build something long term. You have that
choice every day. Every entrepreneur has that choice. Ninety-five
percent of entrepreneur is they build their businesses but they don’t
care about learning industry, they don’t care about their customer.
Andy: Yeah.
Jayson: At the expense of their health, their family, their
relationships, it makes no sense. Unfortunately, it takes … a lot of
them hitting “rock bottom” to wake up. Sometimes it happens …
I’m grateful, so grateful this happened when I was 26, 27.
Andy: Yeah.
Jayson: Instead of being 40, 50 or 60 and my daughter doesn’t
talk to me or I’m divorced for the third time and that kind of stuff.
Andy: Yeah.
Jayson: My wife was very, very supportive and kind of
[inaudible 00:41:47] because she knew. She knew I could pull out. I
plan stuff a little more long term now than I would before. I’d be
more focused on the money before and that kind of stuff. Like I say,
she’s fairly supportive. And there’s a quote I always think about is
that a man’s loyalty is tested when he has everything. A woman’s
loyalty is tested when her man has nothing. She stuck with me
through … in my darkest days.
Andy: How important has that relationship been to you?
Jayson: Well, my wife helps me with Mastermind Talks now
which was kind of a sticky thing.
Andy: Oh, cool.
Jayson: Yeah. There’s a lot of people who kind of shy away
from getting their spouse involve in their business and I was very
hesitant about it as well because …
Andy: Yeah.
Jayson: … that could put a lot of pressure on relationship.
But, she’s absolutely fantastic with the high-touch stuff.
Andy: Yeah.
Jayson: I’m much more big picture. Because we have that
contrast, we work together extremely well. One of the highest … I
guess one of the best things that people appreciate about the event
that we had was extremely high touch. I attribute that to kind of
having her under my wing to some degree.
Andy: Beautiful, man. It’s crazy. I’ve brought this up
before. A lot of entrepreneurs … I think a lot of them feel like they
don’t have time for relationship, but that can be the catalyst for the
most amount of growth. It can actually catapult your business
forward farther which is really interesting I think.
Jayson: For sure. Having a relationship is like amplified
emotion. You know what I mean?
Andy: Yeah.
Jayson: The highs are highs and the lows are lows.
Andy: Yeah.
Jayson: But that is the journey of an entrepreneur to a certain
degree. You know what I mean?
Andy: Yeah.
Jayson: … we live for. If you don’t have that in your life …
It’s one of those things like every time I have a success, the first
person I want to share it with is her. You know what I mean? That’s
always the thing. If I didn’t have her and I was just solo guy, it’d be
a whole different dynamic that I’d be missing out on.
Andy: Yeah.
Jayson: Like I said, it’s definitely not all peaches. You know
what I mean? Marriage and stuff like that is a difficult thing but …
like I said, in order to have real contrast in your life, the highs and
highs and lows and lows, there’s no other way to do it.
Andy: Totally.
Jayson: But there’s also a time where you have to make
sacrifice as well. During my teens, when people were partying,
going to clubs and stuff like that, I was working. I didn’t have any
girlfriends barely from the age of 18 to 22.
Andy: Yeah.
Jayson: Not because I was not desirable or something like
that. I was working all the bloody time. Because of that, I made
those sacrifices initially so that I can be in a position where I am
today to some degree.
Andy: Yeah. Tell me … let’s talk connecting with people.
Jayson: Yeah.
Andy: This is clearly one of your zone of genius activities;
just from interacting with you. I think there’s a lot of people who
listen. I grew up in a town of 600 people in Iowa, in the middle of
nowhere, and I feel there’s a lot of people … maybe not in major
cities or if they are in a major city, they’re not really connected to
anyone of influence or any mentor in their life. When you said you
started investing in your network and hosting these dinners and
three years later you’re connected with … some … just the biggest
influencers around the world. How did you make that transition and
what … what were the things that you did that made people want to
connect with you and really standout?
Jayson: People that necessarily want to connect with me; I
just want to deliver value to them. The people I was reaching out to
were not … they weren’t seeking me out. You know what I mean? I
was trying … always figure out ways: how can I deliver value to
people? How can I be … From there, slowly kind of creep in to their
lives a little more and more.
I’m very conscious of my network. I have my whole network
mapped on like a mind map. I have three people in my network
which … I’m very, very conscious of who’s in my network, who I
want to bring closer and who I want to push a little further back.
Andy: How do you break the tiers up?
Jayson: Tier one. Tier one in the mind map would be people
who … I’d say, like, I would be able to call them to drive me to the
airport. I have that kind of a close relationship with them.
Andy: Yeah.
Jayson: Tier two is somebody I could reach out to and they
would give me … they’d give me advice or input or something like
that over Skype or a phone call. Those kind of things. Tier three is
somebody I know a little bit but I have to work at that relationship a
bit in order to get comfortable enough to bring them to tier two.
Andy: Yeah.
Jayson: And it could be also somebody I know through
somebody else or whatever the case may be. Usually every six
months I … I should do it actually sooner, not now, because my
network is going pretty rapidly. But every few months, what I’ll do
is I’ll look at the map and I’ll keep adding people to it as I meet
them and then I’ll see … if there’s anybody who I keep in my tier
one who doesn’t necessarily serve me anymore or that I can’t serve
them, or I can’t focus on them right now. It’s not beneficial, so
maybe I’ll consciously move them to tier two and then bring some
people from tier two to tier one.
Andy: Yup.
Jayson: Those kind of things. It’s good to just see your
network as a whole. [Inaudible 00:47:19] that quote. There’s a
bunch of incredible quotes in regards to network. There’s “You’re
the average of the five people you spend the most time with” by Jim
Andy: Yeah.
Jayson: There’s one by John Wooden that not that many
people know about which is a friend of mine told me who was
mentored by John Wooden for 12 years and was that, “If you show
me your friends, I’ll show you your future.” Which is one of the best
quotes I’ve ever heard in regards [inaudible 00:47:42] many people
know about it.
But being conscious of that because you can’t … Most people, when
they think of connecting, they collect. Right? They collect contacts,
they collect business cards, they … so they think if they like
somebody or they become friends on Facebook or they connect on
LinkedIn that that’s an actual contact, right?
Andy: Yeah.
Jayson: When it’s really not. You can really only have a set
group of people that you can go deep with every once in a while. So
I just keep trying just kind of switch it up so that I can go deep with
several people.
Andy: Beautiful. How do you get in touch? If you’re
reaching out to somebody with influence for the first time, how do
you go about that?
Jayson: That’s tough because it really depends. I usually try to
go through somebody else.
Andy: Yup.
Jayson: It’s incredible. When you’re in our network,
everybody’s accessible.
Andy: Yeah.
Jayson: You know what I mean? It’s no longer six degrees of
separation, it’s one degree of separation or two degrees.
Andy: Yeah.
Jayson: That’s the benefit of going deep with people too.
Because if you’re collecting people on LinkedIn and trying to see
who they’re connecting with, that’s usually not who they’re really
connecting with; they’re connecting with other people.
Basically … there’s different ways but I’ve done everything from …
like personalize videos; I use those a ton. I’ll give you an example.
Yesterday I sent out a personalize video to Adam Grant and Jonah
Berger. The reason being is because I love their books; they were
game changing books for me. I’m always trying to put myself in the
… from a marketer’s perspective, always try to put yourself in your
prospect shoes.
Andy: Yeah.
Jayson: When I’m trying to connect with somebody, I’m
always trying to put myself in their shoes. It came from a genuine
place. Contagious is one of the greatest books I’ve ever read of all
time in regards to marketing. All I did was … if you’re an author,
you’re spending all this time writing this book. The core reason
you’re writing this book is you want somebody to pick it up and
really utilize it in that kind of stuff. How often do they get that
feedback loop? Right?
Andy: Yeah.
Jayson: They get some Amazon reviews and stuff like that but
they never get something genuine.
Andy: Yeah.
Jayson: So I started … if I find something helpful, whatever,
I’ll film a video and say, “Thank you for all your hard work.” And
just say, “This is how I applied what you use. It’s a game changer
for me and this is why. I just want to thank you for that,” and that’s
it. Leave it at that. One of the things is just planting … I always
believe in planting seeds before you can kind of reap. Right?
Andy: Yup.
Jayson: A lot of people reach out to people and then say,
“Hey, can you help me with this? Here’s my business plan, do you
think I’m going to succeed?” I’m like, “I don’t know you.”
I always want to hang around incredible people. The one thing, as
well, which a lot of people overlook is, a lot of people go for the
Tim Ferriss’s and the Jonah Berger’s and that kind of stuff, or the
Brian Kurtz’s.
Andy: Yeah.
Jayson: I’m a firm believer that amazing people become
increasingly amazing over time. There’s a ton of people like you
and I.
Andy: Yeah.
Jayson: People blow us per se as far as success, who you just
meet them, you know they’re going to be incredible people. You
just invest in them. You just invest in them. There’s a hell of a lot of
less noise when people are that level than when they are Tim
Andy: Yup.
Jayson: And everybody is trying to get their attention. Right?
I look at that. Who are some amazing people? I don’t care what their
title is. I’ll reach out to them on a genuine level because I’m truly
grateful for something they do, whatever the case may be. If they
want to get back to me and reply, great; if they don’t, no biggie but
there’s also people in my network who are up and comers.
Andy: Yeah.
Jayson: Who are completely going to blow it out. One
example is … you probably know Joey Coleman, right, from
Andy: Yeah. We host a little mastermind here …
Jayson: Yeah. Yeah. Joey Coleman, like, on the
speaker [circ 00:51:26] …
Andy: Incredible.
Jayson: Well, not that well-known, right?
Andy: No.
Jayson: And I was actually ... Joey’s watching this, I wasn’t
… I didn’t know how he’d do on my event because we had 15
speakers and was the best talk as voted by the audience. I’ve never
seen Joey speak. I’ve been friends with him for a few years but
never heard him speak and he was up against Ryan Holiday and Dan
Martell …
Andy: Yeah.
Jayson: Stuff like that. Dude, he crushed it man. He killed it.
He won first place and he had twice the amount of votes of the
second place winner. Tim Ferriss was 9th.
Andy: Wow.
Jayson: He just completely crushed it. Now … he slowly …
Then I got him on to CreativeLive; pushing him to do his book. I
know Joey in two to three years is going to blow up.
Andy: Totally.
Jayson: He’s going to be hot stuff. And that’s not why … I’m
really friends with him now but it’s all about … Again, everybody is
looking for those top tier people. There’s a ton of amazing people
who are just not … haven’t been found yet. Just invest in these
Andy: I first met Joey at … we were speaking at
Underground [inaudible 00:52:26].
Jayson: Yeah.
Andy: He spoke there and he wanted there too. He did his
talk … I don’t know if he’s the same for you but … but First 100
Days. Yeah.
Jayson: Yeah.
Andy: He just did his thing in Creative Live. We’re actually
buying that and giving it to our team to implement for our customers
this year. For anyone listening, it’s basically … his philosophy is
that … if you can … The first hundred days of your customer
experience is what determines if someone will be a customer for life
or not. He just takes you through a process of how to create that first
100 days and make it remarkable. Yeah. His talk is amazing.
Jayson: It just comes down to genuinely wanting to connect
with people who are awesome. Joey, if he wasn’t doing First 100
Days and if he didn’t have traction with that, I know he’s an
amazing person. You know what I mean?
Andy: Yeah.
Jayson: If he goes to be somebody of high-profile one day,
great. But if not, I want to be connected to him.
Andy: (Crosstalk)
Jayson: I know a ton of people who are not big, big names.
They may become big names or they may not but it doesn’t matter.
They’re amazing people.
Andy: It’s really interesting. I like what you said about how
people are one degree away at this point.
Jayson: Oh yeah.
Andy: I think if you’re really … if it’s natural for you and
you really want the network, three years. I think three years of really
investing in it. Maybe like five total but … It’s like this. You reach
this point where everything becomes easy.
Jayson: And it grows exponentially.
Andy: Yeah.
Jayson: That’s what I came to … I thought about the other
day is that my … I have so many people in my network now and the
reason being is because I had those few guys and every time I create
a genuine connection they have …
Andy: A couple more.
Jayson: (Crosstalk) Exactly. Every time … their connections
get bigger and bigger and bigger. It’s one of the wisest investments
you can make.
Andy: Yeah.
Jayson: Nobody thinks like social currency. When I did my
event, actually, be a 100% honest and I told this to the guys in my
mastermind group and stuff like that. The core reason I was putting
on the event was for our social currency. If I can put a hundred
incredible people in the room and break even, then I’m set. I had no
financial goals around it; I just want to break even. Anybody in the
event space, you alluded to it earlier, events are very tough business
to make money on, right?
Andy: Yeah.
Jayson: Usually it’s the first four you lose money on. It’s not
the smartest business to make money. But I saw so much value that
I could potentially create and a by-product of that now is that …
now with that and the mastermind group I started, stuff like that,
now, I can support myself and do what I totally love, which is
hanging around entrepreneurs and just connecting amazing people.
Andy: There’s something so brilliant about the positioning
too. What happens when you bring that group of amazing people
together and you’re the curator of it?
Jayson: Yeah.
Andy: It’s like automatically you have this … this elevated
status among that group of people. I’ll tell you what. Social capital
is the most valuable capital you can have.
Jayson: Well, I mean and like I said, if I were to go
broke again tomorrow.
Andy: Yeah.
Jayson: To the extent I was, if not worse. I have a stronger
network now to pull me out of it faster than ever. Every time you
connect somebody and they get value, that shines back on you every
I had somebody recently who connected me. I went to Costa Rica
with my wife and I put it on Facebook and the guy’s like, “Oh, I’m
going to connect you with a friend of mine in the same town. Really
cool entrepreneur. You’ll love him.” I’m like, “Cool.” I connected
with them. We had … end up having lunch three, four times. Really
cool guy but now I think of the guy who connected us every time.
Andy: Yeah.
Jayson: We can create so much value from me, just
connecting me with this cool person. I do this all the time on other
people but this is actually one of the first few times I really kind of
felt it to a certain degree what other people feel when I connect
Andy: Wow. Awesome stuff, man. This is so great. I’m
having a blast on this interview.
Jayson: We can go as long as you want bro.
Andy: Let’s talk about leaving friends behind.
Jayson: Yeah.
Andy: I read this quote one time that … it said like, every
… great leaders outgrow their peer groups every seven years.
Personally, I think it’s more like every three or four.
Jayson: Yeah.
Andy: But what happens when you do that and you know,
like, the relationships that were amazing at one point but they aren’t
necessarily serving you anymore. How do you handle letting go?
Jayson: It depends. Seven years, I totally agree. It’s way less
than that.
Andy: Yeah.
Jayson: Some people may … some outsiders look at me who
are in the corporate world, sounds like after like … you’re leaving
people behind; you’re a jerk or some like that. It’s not bad at all. It
depends. Initially when you come in to the world, you connect with
people based on proximity. Right? You’d go to school with a bunch
of kids …
Andy: Yeah.
Jayson: … different values, different goals, different futures.
The reason you connect with them is just because you’re on the
same place, same time. What a lot of people do is obviously they
kind of stay within that pack and that first group is one of the … is
the only group I’ve ever had to let go; because I never consciously
picked them to begin with. That was kind of the one thing. I knew if
I want to get to the next level, I’d have to hang around people who
are at the next level. Like if I could attribute my success to one
single thing, because I’ve always hung around people who were two
or three steps ahead of me.
Andy: Yeah.
Jayson: Always, consciously, kind of found those people and
hung around them. Naturally, the other people would drop off.
There’s good people in the corporate world, you know what I mean?
Not all of my friends are entrepreneurs. Most them are because they
have the same values and that kind of stuff but good people are good
people. One of my philosophies is that … if you go to school, you’re
growing all the way up until university or some like that, right? A
lot of people stop growing once they leave school.
Andy: Yup.
Jayson: In my eyes, they made the first decision to stop
growing. You made the second decision to continue to grow; to
keep that momentum, right? They fall behind. They made that
decision, right? You also made a decision afterwards but they made
the first decision. That’s kind of the way I look at it.
As far as … afterwards, when you’re kind of climbing the ranks as
an entrepreneur … Again, I don’t leave people behind per se. I
always judge people on how amazing they are and I’ll give you a
perfect example on how I pick the people from my event.
My event is invite-only. We had a hundred people in attendance, we
had 4200 applications. People who bought tickets for the event? I’d
hold a Skype phone call with them for 15 minutes; 15, 20 minutes to
assess if they are the right fit. If they were not the right fit, I would
refund their ticket. I ended up refunding $43,000 in paid tickets
from people who are not the right fit. Initially, I didn’t know that
this would pay off but the caliber, the people in the room … in the
end was incredible so it definitely was worth doing.
In the call I’d ask several questions like what’s … in order for your
business to jump to the next level, what’s the problem you need to
solve? If people are like, I have a hard time focusing, that’s really a
tier level one entrepreneur and I don’t necessarily want that at the
event. At the end of the day … at the end of every phone call, didn’t
matter how successful they were in business. I’d ask myself, would I
want to have dinner with this person?
Andy: Yeah.
Jayson: And if the answer was no, I’d refund their ticket.
Right? There’s people at the event who had $150,000 a year
business, there’s people who had $150 million a year businesses but
they were all amazing and I want to spend time with all of them.
They were that kind of caliber of people so I judge people based on
how amazing they are not … the size of their business and that kind
of stuff. You see that a lot in business events, right?
Andy: Yeah. Totally.
Jayson: … bigger business and that kind of stuff. But like I
said, you don’t know somebody’s net worth until they go bankrupt.
Andy: (Laughs)
Jayson: (Laughs) So that’s it. Because I tier all my network …
I don’t let people go. Unless they’d like their takers or some like
that or they shouldn’t have been my network to begin with or
whatever. I don’t let people go. I just push them a little further back
so I can bring … strategically bring other people closer.
Andy: Yeah.
Jayson: Because you only have so much bandwidth
every day.
Andy: Yeah.
Jayson: There’s also in the book Give and Take by Adam
Grant which kind of opened my eyes to [dormentize 01:00:33] and
kind of reactivating those contacts that you maybe … lost touch
over the past few years. I do these mastermind dinners, I did …
actually had … I did one last night while I was [inaudible 01:00:43]
with Dan Martell and Mike McDerment from FreshBooks and a
bunch of other cool tech guys.
Andy: Yeah.
Jayson: I also had 13 others going which are the first time
ever. I’ve never done other ones and I created these party host
packages so I was kind of showing other people how to do it. We
have 13 dinners going last night.
Andy: Holy shit!
Jayson: Yeah. It was really cool. Yeah, that’s kind of it. In
regards to reactivating … [Dormentize 01:01:09] is … so, there’s
people in your network that you lost touch with but you already
have that social capital in and it’s easy to rekindle those
relationships and it’s great to catch up, right?
Andy: Yeah.
Jayson: Every once in a while, I’ll just do a dinner of people I
haven’t connected with in a while. I’ll do dinner of six, eight people
and we’ll all catch up. Some people will be like … I got to move
you to tier one. You’re more awesome than you were last time. You
know what I mean?
Andy: Yeah.
Jayson: Or some people … it’s just good to kind of reconnect
and maybe we’ll check in again in a little while.
Those are kind of the two things. There’s certain people you have to
leave behind because they’re toxic. That definitely rubs off on you.
Then there’s other people who are not toxic but you have to be
conscious of your bandwidth and how much you can kind of devote
your time to certain people.
Andy: Beautiful, man. This interview has been incredible.
I asked Jayson ahead of this, I was like, “Is there anything you want
us to promote or like sharing anything?” He’s like, “No, man. I’m
just here to give as much value as I possibly can.” I respect that so
much. is where they can learn about the event that
you do once a year; if they’re interested in going. If people want to
reach out to you or connect with you personally, how can they get a
hold of you?
Jayson: Yeah. Like I said, I’m going to try it this way. I’m
going to put my … I’ll give you guys my email. If any of you guys
want to … to chat, I’ll chat with you guys on Clarity but shoot me
an email first. It’s Jayson, J-A-Y-S-O-N
Again, and I’ll find a way to

Andy: Beautiful. We’ll put all of that stuff in the show notes
Jayson: Cool.
Andy: Jayson, thank you, man.
Jayson: Awesome, dude. I look forward to connecting
to you in person.
Andy: Yeah. I know. I know. Me too.
Jayson: Thanks again for having me, dude.
Andy: Take care, man.
Jayson: All right. See you, man.
Closing: Thank you for joining us. We’ve taken this interview
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