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October 31, 2024 45 mins

Rob Ray, a 25-year MSP veteran who transformed from accountant to industry titan by breaking every conventional sales rule.

In this value-packed episode, James discusses Rob's exact strategies to build one of the largest MSP communities and why traditional business growth methods are failing in today's market.

He shared his unexpected strategies that turned regular clients into fierce advocates. 

A must-listen for MSP owners, sales leaders, and tech entrepreneurs who want to build lasting industry influence.



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Episode Transcript

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Speaker 1 (00:00):
I want to sell a product that you could actually
use.
I want to sell a service thatyou could actually take
advantage of.
I'm going to make you money,save you money, something along
those lines.

Speaker 2 (00:07):
Rob Ray, the brilliant mind that helped build
thriving MSP communities forthe last 25 years.
What put you in a position tooutperform everyone else, even
in?

Speaker 1 (00:17):
that early stage, you always got to put yourself in
the mindset that we serve them.
Okay, we're not peers, right,we're not buddies, we that we
serve them.
Okay, we're not peers, right,we're not buddies, we serve them
.
That is our community.
We don't survive unless theysurvive.
You know, I think those aresome of the things that you can
do in order to establishyourself as part of this
community.

Speaker 2 (00:36):
And how do you build resilience in your own mindset
to keep fighting the good fightand be out there and getting
yourself through those toughdays?
You know what it is, rob, thankyou so much for joining me
today.
It's a great honor.
It's a great privilege to haveyou on the podcast Battlestars
of a Sales Leader.
You have been a mentor and anidol throughout my career For

(00:58):
the last decade.
When we first got together, whenI joined Datto Down Under, you
were the first person at Dattothat I met and I watched what
you did and I was blown away athow you were able to just
transform an industry and createthis incredible community and,
yeah, super impressive thatDatto wasn't the first one that
you did and it's not the lastone.

(01:19):
Appreciate you with Pax8 today.
So, as part of this discussion,we'd love to tap into your
mindsets and the strategies,your philosophy of how you've
successfully gone off and builtmultiple communities.
Before diving into all of that,you've been in the industry for
25 plus years.
Thinking back to even when youwere at school, did you think
that you were going to begetting into tech and did you

(01:40):
think that you were going to begetting into some sort of sales
role?

Speaker 1 (01:43):
Absolutely not.
And, by the way, it's anabsolute honor to be here with
you, my friend, and doing thisagain.
So thank you for the invitationand I'm equally happy to be
here.
No, absolutely not.
You know it's.
You know, when you're youngerand you're going through school
and you've got different ideasas far as what you want to do
with your life, and it changesall the time.

(02:04):
And by no means was I the beststudent, so it wasn't like I'd
have my pick of the litter oranything like that.
And also, you know, unliketoday, you know only like the
really really smart kids wouldgo on to college or university
and then the rest of us wouldtry to figure out how we were
going to struggle through therest of life.
You know my goal ultimately Idid end up going to university.

(02:27):
I ended up starting to go touniversity.
I wanted to be an accountant ofall things, which is the exact
opposite role of what I do today, and I'm super glad that that
kind of didn't work out.
But that was the goal.
But you know, I discovered thispassion for sales kind of at an
early age.
I was working for a bank, for afinancial institution, and, um,

(02:50):
this is back in the days whenyou know you would go into a
local bank branch to transact,like right before, just as as um
, bank machines were coming out,atms were coming out and uh my,
my boss had tasked me with um.
It's a little bit of a longerstory, but I wanted a bet, I
wanted a bigger job, I wantedbigger money.

(03:11):
And he said, uh well, you haveto get into sales in order to do
that.
So there were rolling everybodyinto these banking plans, like
that per month fee that youwould pay for a banking plan.
He said if you can convert morepeople to this banking plan,
I'll give you a sales job whichwill ultimately pay me.
I don't know, it was like anextra dollar, a dollar a pay or
a dollar an hour kind of thing.
And ultimately it worked.

(03:32):
I mean, I went out, I grindedit out, I was the top person,
not only in the branch but inthe region, but kind of
discovered this passion forsales and then just kind of
continued that way, focusing inon that piece there yeah, your
initial, your why was I want togrow and I want to make more
money?

Speaker 2 (03:47):
and then you were given an opportunity and you
read you're more successful.
Can you think back to what putyou in a position to outperform
everyone else even in that earlystage?
Like what did you dodifferently to everyone else?

Speaker 1 (03:57):
you know it's, you know, and then you you kind of
discover this, this like forsales, and you know it's sure
it's a little I mean in theinitial stages it's kind of
money motivated but thenultimately you figure out that
you know you actually enjoythese types of things and you
know there's always like there'slike those two types of sales
where it's like typicallysalespeople are thought of in a

(04:21):
very negative light.
Right, we're just trying topitch something, we're just
trying to sell you something.
I've always kind of turnedaround and focused on the
relationship sales aspect of it,where I want to sell a product
that you could actually use, Iwant to sell a service that you
could actually take advantage of.
I'm going to make you money,save you money, something along
those lines.
So when you convert it over tothe relationship sale and kind
of focus your energy around that, it takes away from the whole

(04:43):
negativity of these differentyou know connotations around
what, what salespeople are andwhat salespeople kind of like or
what their motive actually is.
I genuinely believe that theproduct that I'm selling will
add value to you, or I don'twant you to buy it.
And I think if you go and kindof go in in that approach, then
you'll you'll succeed all daylong, but for me, you know to

(05:05):
answer your question, it wasmore about challenging myself
Can I do better than I did theprevious month?
Obviously, you know.
When it comes to sales, one ofthe great parts about it is the
fact that you have, potentiallyhave, peers around you that
you're competing against, andwhat other role in an
organization benchmarks youagainst like quantitatively
benchmarks you against otherpeople where you can say I am

(05:27):
better than you because I did Xright?
There's not many roles inorganizations where there's an
actual scorecard and you knowwhen you're focused on that,
looking at that and and can kindof prove to an organization
your success.
I mean, that's where it is, inall honesty, though, james, the
only reason why I ended up insales.
That's where it is, in allhonesty, though, james, the only
reason why I ended up in sales,because I had to drop out of
school, so I didn't finish myfinance degree.

(05:48):
I was, you know now would say,very blessed to have had a child
at a very young age.
It wasn't the plan.
You know you're supposed tofinish uni and then start having
children, but you know Iultimately had to leave school
in order to go and make moneyand I wasn't qualified to do
anything.
But you know, sales, sales isone of those roles where you can

(06:10):
kind of make a lot of money andnot have to have a degree or an
education to be able to do it.
You just have to have thatpersonality, that grind, that
want.

Speaker 2 (06:20):
And how many years were you in sales before you got
opportunity to step into peopleleadership, and I don't know if
it was a tipping point in yourcareer, but was there something
that excited you about actuallytransitioning to really driving?

Speaker 1 (06:34):
a sales team, logical step is to be managing people
right.
You come from an individualcontributor to a manager of
people and you know that's notalways the best thing.
I mean, I've had phenomenalsalespeople work for me over the
course of years, but they areabsolutely terrible people

(06:55):
manager.
And it's this whole idea isthat are you better as an
individual contributor, justtaking care of yourself, living
on your island, versus trainingand coaching other people?
And I think there's the otheraspect of it too, that you have
it set in your mind that youknow growing into a management
role and managing other peoplemeans you're ultimately going to
make more money.
That's not necessarily trueeither.

(07:15):
I'm actually a big proponentthat the you know top of your
top sales force should be makingmore money than the people that
are managing that sales force.
There should be more of amedium mark for that.
So you have to have you know,get away from the idea that it
is a it is, it's a naturalprogression to move from an

(07:35):
individual contributor to amanager, and also get away from
the idea that everybody's goodat people management.
Right, it is a completelydifferent skill set, and there
are days that I love it.
There are days that Iabsolutely hate it.
You know I just found a passionfor it and you know,
fortunately, through becomingkind of the best at the sales

(07:57):
role, they kind of default,promote you into it, which again
logically doesn't make anysense.
But you know that just happenedto be where my journey went.

Speaker 2 (08:05):
Yeah, it's an interesting point because you
often see that it is the topperson gets promoted and becomes
a sales manager and the realityis a lot of teams take a big
hit because all of a sudden thatbig revenue stream that they
had has now been depleted asthis top salesperson tries to
figure out how to motivate andinspire different reps.

(08:27):
But you were at CompaqComputers for a number of years
and then I think it was HPacquired them at the time and
then you transitioned into levelplatforms.
Was that the next step for you?

Speaker 1 (08:42):
There was a little bit of a journey there.
It was Compaq Computers, yes.
Yes was the first kind of roleat it, and the reason why
compact actually hired me,interestingly enough, wasn't
because of my technical skills.
As you know, james, I am nottechnical in any way whatsoever,
right, um?
But compact, what they werestruggling with back in the day
was they were kept putting andpromoting these technical people

(09:06):
into sales management roles andthey were missing the sales
management skills Great atunderstanding the tech and the
line card and everything thatthey can sell, but not so good
at managing the day-to-daypeople.
And it was an inside salesgroup.
It was kind of entry-levelsales, so it was a high-churn
group sales group.

(09:26):
It was kind of entry levelsales, so it was a high churn
group.
And that's where they insteadturned around and focused on.
We need a good sales manager asopposed to somebody that's
coming from the technical space.
So that's how I ended up in IT.
I did exit IT because when HPacquired us, I'm out of Canada
and the Compact Canada executiveteam.
Most of them were let go.
They started a payroll companyin Canada and asked me to join

(09:49):
them.
Knowing my sales background, itwas a phenomenal opportunity to
go and join a payroll companywhich, again, finance being a
little bit of my background, alittle bit of my passion went
over there.
That being said, I got bored.
I got colossally bored with itand needed to get back into the
IT space, because IT one of thebeautiful things about our space

(10:10):
is it's constantly changing.
There's always innovation,something's always moving
forward and a lot of industries,especially in the finance space
, things tend to stay the same.
They want them to stay the sameand predictable, and it's just
not as much fun.
So you know, it was kind ofcool to have the ability to come
back into the IT space andspecifically into the MSP space

(10:30):
when I came back, rather thangoing back into the hardware
side.

Speaker 2 (10:33):
So you transitioned back into the IT side, into
level platforms.
You were, came in in the salesrole, sales leadership, also
business development as well.
And you know, I want to unpackthis a little bit, a little bit,
because a lot of businessesthink about their go-to-market
strategy and it's heavily aroundeven today it's hey, what's my
sales strategy, my marketingstrategy?
Am I product led?

(10:54):
Am I sales led?
Have I got some events that Igo to?
But there's a piece that I thinkis missing with many
organizations, whether it'sinside the IT channel, whether
it's outside, think is missingwith many organizations, whether
it's inside the IT channel,whether it's outside, is this
concept of community, thisconcept of ecosystem.
And I think that you werereally one of the pioneers of

(11:15):
that in the level platform, dave.
Where, like what was it?
You know, from your perspective, where you actually identified
this opportunity to create acommunity?
I don't even know if it wascalled community back then, but
really bringing together peopleand giving them a sense of
purpose and buy-in.
Talk me through what wentthrough your mind and how did
you devise that strategy thattook the business from

(11:38):
relatively small to prettysubstantial.

Speaker 1 (11:41):
Yeah, yeah, you know actually.
So you're absolutely correct.
It's kind of morphed over theyears and I'm sure you
experienced this back in yourlike Autotask Enable days, all
those things.
You know I was VP of sales atLevel, which is an old RMM
company discovered, or what wewere kind of working towards was

(12:03):
the idea that you know, thecommunity, like the people that
are in our space, they have atendency to talk to each other,
even though they tend to competewith each other.
They have a tendency to talk toeach other.
They tend to make buyingdecisions as groups as opposed
to is as individuals.
You know, if my competitor goesand chooses product A, I'm
going to go and choose product Bbecause I don't want to have

(12:26):
the same product in the samestack, so that there's like this
comparison of price rather thanyou know who's got a cheapest,
kind of thing.
We don't deal with any of that.
That most industries do Instead, like the fact that these
people all work together is veryit's a very unusual thing.
So you know, we startednoticing this and really
leveraging that, uh, back in thelevel platforms days.

(12:48):
You know, we didn't like yousuggested, didn't even quite,
quite call it community, we justhad to take advantage of how
the market was responding andhow we could continue to sell
stuff.
Um, our product was not thebest product in the market,
right, and rmm was an.
It was an emerging technology.
There were other products thatwere better.
There were other products thatwere cheaper.
You know, one of the thingsthat we took great pride in was

(13:10):
our relationship that we havewith our partners, and we had to
have this phenomenalrelationship because we weren't
going to win on price and weweren't going to win on tech.
That relationship build bytaking care of your clients, by
returning their phone calls, byanswering their phone calls, by
providing great tech support,those kinds of things.
Well, you hope that yourtechnical team fixes all the

(13:36):
problems in the background andthe price-wise it all kind of
comes back into line.
I think then, when I joinedDatto in 2013, and I'll give you
and I both worked for AustinMcCord for a number of years,
you know, I think that's wherewe can kind of give a little bit
of kind of a tip of the capthere to him, because he was the
one that kind of recognizedthat this could be a role in

(13:57):
itself.
And you know, when I joinedDatto, he's like I'm like, you
know, my forte is sales.
My forte is being VP of sales.
I know how to run salesorganizations, I know how to run
funnels, I know how to do allthose things that are necessary
to be successful.
And he goes I don't want you insales, I want you to build out
the community strong communityout there, and they were winning

(14:27):
business as a result.
These people wanted to be a partof this group and I think it's
a combination of a couple ofdifferent things.
It is the fact that our space,it in general, continues to
flourish, continues to bemassive amounts of opportunity
for growth, for sales, for, youknow, you see just even the
number of new vendors cominginto this space Like there's
just so much opportunity for,for people in this space to make

(14:50):
money that, when it comes to,you know, uber competitive
cutthroat, it just doesn't exist.
I think the other part of it,too, is, you know, we're in the
IT world, we tend to be a littlebit more introverted, we tend
to be a little bit more nerdy.
This is a group that acceptsthat.
This is a group that actually,you know, wraps its arms around
it and really relishes in it.

(15:11):
So you know we're all at.
You know the root we're all packanimals.
We all want to be loved andaccepted.
We want to walk in a room andwe want to know everybody in the
room is excited that you'rethere.
That happens in our space, ithappens everywhere in our space
and I think for you that happensin our space, it happens
everywhere in our space and Ithink, for you know, for those
particular reasons, this is whyyou know, I think our community
in our, in our, in our vertical,here, in our ecosystem, here, a

(15:34):
is super, super important, butb I mean I think that's the
reason why it exists in thefirst place and continues to,
continues to flourish for thosevendors, whether they're in the
the msp channel or even evenoutside of the MSP channel, that
may be listening if they'rethinking about what does it mean
to build a community level?

Speaker 2 (15:53):
what would you say?
The core steps are that backand say well, what does
community mean?
When we say this word community, what are the characteristics
of that, so that we actuallyunderstand what we're working
towards?

Speaker 1 (16:13):
That's a good one, because this is something that
we've all been trying to definefor a very long time.
You know what is the actualcommunity and it gets really
really hard to measure as aresult.
It's almost like, you know,marketing can be measured in
certain things like MQLs andSQLs and those kinds of like
activities, but ultimately, youknow, is the marketing message
the right one?

(16:34):
Are people feeling it, arepeople understanding it and
they're responding to it?
And there's only so few waysthat you can kind of measure
that in order in a quantitativeway.
It's more of you know.
Gary Vaynerchuk's related it tomore of like having faith in
God.
You just have it right.
It just has to be there thatyou just kind of believe that
this is working and that thesethings are in place because

(16:57):
people are responding and you'regrowing as a result.
So you know it's hard when you,when you talk about what
community is you know if I'mgoing to define it.
I guess we've talked aboutreasons as to why it actually
exists.
If we're going to define it, Iwould suggest that it's more.
When you go to a Reddit, I knowas much as a lot of us will

(17:17):
shake our heads and roll oureyes, or go to a Facebook group,
when you have like-mindedpeople from all over the world
sharing information as far aswhat vendors are using, how
they're using them, how they'repricing them, how they're going
to market with them, and sharingthis in open forums like those
types of things.
I think that's done a ton ofevents globally and you see it.
You see it, when everybodywalks in the room and just kind

(17:47):
of there's this commondenominator that everybody just
kind of gets along, everybodyjust kind of shares, everybody
kind of, you know, has thisconversation.
I mean I think that's where youknow the, that community
engagement comes in.
So if you think about it from avendor perspective, is so
critical that you have a goodreputation amongst this group,
that you have a at least decentenough product or own, you know

(18:11):
the, the non-decent parts of it,with a, with a roadmap, and
here's what we're working on.
Transparency is a word that Ithink should be used more in our
space and I think vendors thatare focused on this and at least
recognize that there is thisaspect of this community here
and are transparent with thatcommunity, I think ultimately

(18:31):
are the ones that are going towin.
And you know you've mentionedthis a couple of times right
where you know I did it at level.
I brought it to data.
Pax 8 already had it.
I'm just kind of continuing torun with it.
You did the same thing withyour journey.
With it, you did the same thingwith your journey, and then you
know there's others in ourindustry that we've seen
continue to run in that, in thatyou know embracing this

(18:51):
community aspect, being outthere, shaking the hands and
kissing the babies and makingsure that everybody's happy and,
when they're not, like runningat it instead of going and
hiding.
And you know you got one shot atthis.
You know perfect example ofthis and James, you can relate
to this there's a very goodfriend of both yours and mine,
britt MSP, obviously out of theUK, and they used Datto back in

(19:17):
2013 when it was just kind ofnew, new, new, no-transcript

(19:47):
says I get it.
It's a completely differentteam.
It has completely beendeveloped, it's been completely
changed, the pricing's different, everything is different about
it.
But I can't go back because weall still have this bad taste in
our mouths associated with yourbrand from 10 years ago.
So you know, it's this weirdkind of thing where you know you

(20:07):
really, really have to takecare of everybody that you
possibly can out of the gate,because you potentially may only
have one shot at their business, not just now, but probably for
the eternity of your business.
Msps don't tend to leave andcome back to organizations.
They just tend not to.
They'll go and find somethingelse if they're unhappy.

Speaker 2 (20:28):
I want to take a step back, because you were talking
about community and how Redditand people, how they communicate
and talk about you almostbehind your backs.
But part of me thinks that thatis part of the community.
It's also a cause and effect ofhow you have created your
business and your brand.
And one of the things that Ialways admired about you and I
always have laughed at is I saidRob is the guy who will be the

(20:51):
last one at the bar until twoo'clock in the morning with
partners and he'll be the firstone doing the keynote at 8 am
the next morning.
And I don't know anyone else inthe world that can do that like
you can.

(21:23):
But one of the things that youdo when I've looked at how you
operate and I always try tolearn from the best um, you know
where I think I don't know.
You said we're pack, packanimals at heart, like we want
to be heard and loved and and Ithink that there's a lot of
underlying psychology in insales um, and it's how do you
make people they often say it'snot what you say, it's how you
make them feel and and creatinga forum of making people feel

(21:46):
collected and making people partof something bigger than they
are by themselves is is, from anobservation perspective,
something that I think thatyou've done incredibly well as
well, and it's not easy, and itdoes take a lot of time and
commitment and investment to getthere, but, like you said, the
the packs speaks speaks, or youknow the pack is spoken.

Speaker 1 (22:09):
if they really like something, then they'll go all
in with you as well yeah, no,you're absolutely right and and
you know this too, because I'vewatched you do exactly the same
thing um, people like to dobusiness with people they like,
and if you're not a likableperson, then, or if you don't
like people, if engaging withhuman beings just isn't your

(22:29):
thing, and that's fine.
There's a lot of people that, sothat people can relate to it.
They want to be a part of yourcommunity and there's a lot of

(22:56):
forgiveness that comes in that,which is things like you can
drop the ball, bad productrelease or you know a price
increase or something alongthose lines.
If you have a community wherepeople just enjoy doing business
with you, they'll pay a littlebit more.
There's a lot more forgivenessfor that, because you know it's

(23:17):
not a culture where it'sexclusively focused around tech,
even though we're in the techindustry, you know it has to
work, but you can make mistakes.
You don't have to be thecheapest.
They're not always looking forfor the absolute cheapest.
There's a lot of forgivenessthat goes into having a
phenomenal community wherepeople just kind of want to be
there.

Speaker 2 (23:36):
And, just just to you know, we touched on.
We touched on kind of gettingto look at like, what does a
community look like for somecompanies that are?
You know they're, they've hadsome funding, they're
internationalizing and goinginto new regions and looking at
creating some form of communityin their different geographic
geographies, whether it's in theASEAN market, apac, europe,

(23:58):
north America.
If someone is launching into anew market, what are two or
three strategies that you canthink of that would help to
accelerate them building thatcommunity, and are there any
lessons that you've learned fromgetting it wrong?

Speaker 1 (24:13):
Oh, absolutely so.
I think a few different things.
Number one this does take time,right.
Think about it.
As you know, anybody that like,think of it as any relationship
that you've ever had with apotential partner or spouse.
You know you don't get marriedon the first date and I think
that a lot of well, most of usdon't.

(24:33):
But you know a lot, of, a lotof the relationships in this
space are built over the courseof time and you know, I think,
that longevity piece is is iscritical.
You need to keep showing up andkeep showing up and keep showing
up.
I see too many vendors comeinto this space, try to sell
something.
After three to six months it'snot working and they leave, and

(24:54):
part of the problem is is thathappens repeatedly, to the point
where in our space at least, inthe channel space, within
communities in particular,they're waiting to see if you're
going to leave.
They're waiting to see ifyou're going to be around for a
year, for two years, and onlythen do they tend to want to buy
something, and so so it's thisdance that kind of goes on for a

(25:16):
while where you need to bethere, you need to be consistent
, you need to keep showing upand then only then will they
will.
They tend to have a certainlevel of trust that they'll
actually start buying something.
So you, whenever I'm talking toa vendor or anybody that wants
into the space, my firstrecommendation is you've got to
give this time.
You've got to give this time.
Don't expect anything right outof the gate, very, very quickly.

(25:40):
I think that the other aspect ofthis is that word of mouth
right that your best salespeopleare always going to be your
clients or your partner, so thefaster that you can find these
partners as much as I just said,it takes time to find these
they're going to be the mostcritical part of this.
So make sure you take care ofthem, very good care of them,
almost an over-caring of them,because an MSP, or even anybody

(26:05):
in the channel in particular, ismore likely to make a buying
decision or factor their peersinto the decision more so than
ever.
And if you don't believe me, goto Reddit, go to Facebook.
You can see that people are allthe time trying to compare your
organization with others,trying to say, hey, I'm unhappy
with this company, I'm thinkingabout this one, and they go to
their local communities forfeedback rather than doing demos

(26:28):
and trying to do the researchon their own.
So make sure you've got a greatonline presence, a great person
presence, where you canactually have those level
conversations.

Speaker 2 (26:39):
What are some of the ways and I agree with you around
taking care and really goodcare of your clients, but what
are some examples of how you'vetaken care of clients over the
years that may inspire othersearly on the early on their
journey to to get some quickwins?

Speaker 1 (26:53):
you know what there's ?
Just, there's a coupledifferent things, um, if I, if I
see.
Well, so, first of all, uh, youalways got to put yourself in
the mindset that we serve them.
Okay, we're not peers, right?
We're not buddies.
We serve them.
That that is our community.
We don't survive unless theysurvive.
So you have to think of them.
You almost have to put them oneup from where you are, and I

(27:15):
see too many vendors talkingdown to them, and even when I
joined this space 25 years ago,I was told that we tell them the
way it's going to be that kindof thing.
I'm not a big fan of that.
We serve, we serve them and Ikeep that in mind.
So you know, you need to be very, very humble about the way in
which you do things, which meansif somebody goes online and

(27:37):
decides that you are the worstperson, you are the worst
company, you're the worst tech,I have a tendency to let them do
that.
I'm not going to defend that.
I'm not going to.
You know, I'll reach out andsay, hey, if you have problems,
I can help, let me go and fixthis problem, but I don't get
into situations where I getdefensive or argumentative.
Look, not everybody loves thecolor blue, right?

(27:59):
So you know you're not going tobe able to get everybody to
wear the color blue.
Some people hate the color blue, just understand.
I'm not saying this becauseyou're wearing blue, james, but
it's just.
You know the you just you'renever going to change
everybody's mind and you justhave to accept the fact that
there are people that are goingto get frustrated and they're
going to vent about you know.
You just got to let that go andnot get defensive, because that
makes things worse.

(28:20):
However, if they are asking forhelp, this ticket's been open
forever.
I can't get anybody to call meback.
You know things like that.
I'll jump in all day long, andyou got to look for those things
Because they're hoping nothoping, but they.
It's almost a little bit of atest to see how responsive you
actually are.
So be very proactive with thosetypes of things.

(28:41):
You know.
I think those are some of the.
You know at least the quick,early, cheap things that you can
do in order to establishyourself as part of this
community.

Speaker 2 (28:49):
Love it Through the last few years there's been
obviously external challengeshave gotten in the way and the
slow business has gone good andit's gone slowed down and teams
have grown and then we've had torationalize in places and it's
not always been easy.
You're a guy that's been on theroad for most of your life and

(29:10):
traveling.
How many days a week would youtypically travel?

Speaker 1 (29:16):
These days it's four to five days a week.
For sure, I try to be home onweekends and some holidays, but
yeah, it's a lot, it is a lot.
But again, that social aspectof what we do is super important
and I love doing it.

Speaker 2 (29:29):
I do love doing it, that social aspect of what we do
is super important and I lovedoing it.
I do love doing it.
So, and how do you, how do youbuild resilience in your own
mindset to keep fighting thegood fight and be out there and
getting yourself through thosetough days.

Speaker 1 (29:40):
You know what it is.
I'm, I'm, I'm in a bar.
Surprise, I'm in a bar inDenver, Colorado, and I have
this guy that comes over to mean MSP and he comes over to me
and he says you know, we youprobably don't remember me, but
we met about 10 years ago andyou gave me some advice that

(30:00):
completely changed my life.
It completely changed mybusiness.
And he said, and he, what hedid, was he actually FaceTimed
in his partner, his businesspartner.
And, as he says to his businesspartner, he says you're not
going to believe who I'm sittingwith.
And he shows, he shows mesitting there and he's like holy
crap, that's Rob Ray.
Like you're not going toremember this, but we met 10

(30:21):
years ago and, and they're,they're honest, I, I, I'm pretty
good with faces.
I can usually tell if I've metsomebody before, but trying to
remember the name if we've metonce in 10 years is actually
really hard.
However, the fact that theysaid you know what?
Both of us are millionairestoday because of a piece of
advice that you gave that we ranwith, and I'm like that's like,
it's such a humbling experience.
I don't believe it.

(30:42):
They're the ones that had to doall the really hard work.
All I did was just reiteratesomething stupid that I probably
heard from somebody else, andthey just kind of listened to it
and ran with it.
But in all honesty that is.

Speaker 2 (30:54):
Do you?

Speaker 1 (30:55):
remember what the piece of advice was it was.
It was actually moving, tryingto move away from one-time
revenue to recurring revenue.
It was something along thoselines.
It was something about thetransformation of, of managed
services, firing bad clients.
You know that, that kind ofstuff.
It was something along thoselines in In yours, in yours, in
my mind, because you know weboth come from that PSA or RMM.
This was advice that we wouldgive out every single day, right

(31:16):
?
So in our mind it wasn'tanything life breaking,
revolutionary.
Let's write a book about it.
It was literally probably someof the most basic stuff.
But again, james, and you knowthis, us vendors we kind of sit
there and wait for everybody tocall us and buy our crap, rather
than us going out and providingeducation and providing support
and having conversations abouttheir businesses that maybe have

(31:36):
nothing to do with ourbusinesses.
It's being again part of thatcommunity.
It's trying to find ways inwhich you and I get an
opportunity to talk to tens ofthousands of msps or vendors
every single year from aroundthe world.
Right, there is strength inthat knowledge.
Why not share that witheverybody that's out there?

(31:56):
Yes, you're going to have somepeople that are going to say
don't care, you're wasting mytime, you're just trying to do a
bait and switch, trying to getme to buy something.
But in essence, you know whenand it happens more often than
not when somebody comes and saysyou changed my life and I know
we're not talking about you knowlife critical things but making
money, running a successfulbusiness, growing a business

(32:17):
providing employmentopportunities for other people
who could do those same thingsfor their families, like when
you look back at this at the endof the day, especially in the
industry that we're in, that'sgrowing like crazy.

Speaker 2 (32:28):
These are big wins.

Speaker 1 (32:29):
So you know, when I'm sitting in that hotel in
Detroit, Michigan, on my 15thday on the road and I haven't
seen my wife or my kids and Ihate my life, those are the
things that kind of come up forme, which is there's a purpose
to all of this and it's beyondjust making money and selling
more of my stuff.

Speaker 2 (32:47):
I've really picked up some of the key things around
community.
It's around delivering highquality service.
It's around really helpingpeople to grow their business
and really being proactive andgoing out there to look at where
there may be an opportunity toimprove things.
Here's a question for theorganization and vendors that
are on the way up.

(33:08):
They've got, maybe, thetraditional go-to-market,
they've got sales, they've gotmarketing, they've got digital,
they've got some events, butwhat is, from your experience, a
pivoting point in theirstrategy where they should
really create a KPI or a jobdescription for?
someone to go out there andfulfill all of these things that
you're doing, and what does aKPI or success look like if

(33:32):
someone is going to start togive this responsibility to
someone like yourself?

Speaker 1 (33:36):
You talk about hiring a channel chief.

Speaker 2 (33:38):
Yes, I guess the channel chief is the end goal,
but there's a lot of companiesthat may not have necessarily
the budget to have a dedicatedperson solely in channel chief
type role.
Maybe they do.
Yeah, is what is your opinionon when?
When should you get that person?
And if you can't afford adedicated person, how do you
begin to compartmentalize thatrole and responsibility and

(34:00):
determine success?

Speaker 1 (34:02):
yeah, so that's so.
It's a.
It is a great question and andand I'm I'm agreeing with you
Not everybody can.
So having you know we've talkeda lot about this how
personality is so important inthis, and having an individual
that can relate back to yourpotential customers, prospects,

(34:22):
partners, having somebody thatcan actually you know and is
interested in doing that thereare so few and far between right
in doing that.
There are so few and farbetween right.
You know, probably in the MSPspace alone, there's maybe
identifiable 30 or 40 peoplethat can actually do this, which
means you're going to pay apremium to hire somebody that
can come in and do that.
There are fractional operationswhere you can actually hire a

(34:44):
company.
We all know a couple of thoseright, james, who can come in
and potentially help with thosekinds of things or have the
leverage and experience,knowledge, connections.
I mean that's, in essence, whatyou're paying for before,
ultimately, you have to find,and particularly find, an
individual that can potentiallydo this.
The other option is findsomebody that you can grow into
this position.

(35:05):
I mean, we've been hiringpeople.
You know what I find.
You know we've been hiringpeople.
You know what I find, you whatI find, if, if so, so the best
people I find for thisparticular role I don't know
where this trend comes from orwhere this tree comes from is
somebody that's really, really,really enjoys sales, somebody
that's been doing a sales role,and they can go through the
entire sales process.

(35:25):
But you know what's the finalstep of the sales process?
The final step is asking forthe business, and that has a
tendency to be some of the moredifficult conversations, because
human nature says that we fearrejection.
We don't want to be rejected,we don't want to get kicked in
the teeth, we don't want peopleto say no to us.
We want to be loved and admiredeverywhere we go, wherever we

(35:47):
go, all the time.
So we avoid situations that putus into situations where we're
going to get rejected and in thesales process there's going to
be a point where you're going tosay, are you ready to buy?
And there is opening that doorwhere somebody goes no, so
you've got that rejection piece.
So there's a lot of reallyreally good people that are out
there at taking a sale rightthrough the entire process, but

(36:10):
really bad at asking for thebusiness.
They want the, instead theprospect to come to them and say
, all right, I'm ready to buy.
So they never actually askedthe question.
Instead, they just wait andkill them with kindness and
phone calls and emails, waitingfor them to be the ones that say
, okay, I'm ready to buy, ratherthan us asking for that

(36:30):
business.
What I find is the best peoplefor this role are really good at
the entire sales process, butmaybe miss that one final step,
which, in my mind, is actuallyokay, because what is our job?
Our job is to get peopleinterested in our organizations.
It's to get people interestedin what it is that we're doing,
the journey that we're on.

(36:51):
Why do you want to be part ofour community?
Why are we the cool vendor inthis space and why do you want
to be part of all this?
And then I'm going to hand itover to somebody that's going to
say, all right, let's get youon to buy something, or let's
get you a certain product oronboarded or those kinds of
things.
So even if you have somebody inyour organization that you find
like and we see this all thetime really, really nice people,

(37:12):
but they're, you know, butthey're just not hitting their
numbers.
You know, maybe those are ourideal candidates to be the ones
that are out there shaking thehands and kissing the babies as
long as they're passing thoseleads back over for somebody to
actually close.
There will be a point where youknow all this is so necessary
and a lot of times it's usuallythe founder or one of the senior

(37:33):
executives that kind of has tostart it.
Pax 8 is very similar.
One of the most identifiablepeople at PAX 8 is our president
, which is my boss, and when Ifirst met him he was channel
chief of this organization.
I now work for him.
But you know he's now evolvedand moved and hired enough
people and can afford to hireenough people that he doesn't
need to do that anymore.
But sometimes that person isthe identifiable person that

(37:57):
goes out.
You know Artie Bellini was thewas the first person out doing
ConnectWise meetings.
Or Austin McCord was the firstperson out doing ConnectWise
meetings.
Austin McCord was the first oneout doing those Datto meetings.
So sometimes it does need to bea senior leader or the creator
of that tech to start, but thenultimately you'll find enough
success that you can bringsomebody else in to do that.

(38:17):
And how do you quantify success?
Dollars, revenue generation.
You know there has to be acertain amount of revenue
generation.
Ebita, of course, is always,always the great measurement.
But you know you don't need tofocus necessarily on that part
of it until you're starting toget really serious about raising
money or selling the company.
But how do you measure success?

(38:38):
I would you know.
I would suggest it's it's gotto be, it's got to be revenue.
Right, it has to be.
My wife runs a small businessthat she started probably about
four or five years ago.
She's up to about fiveemployees Right now.
Every dollar that she getsshe's investing back into this
business.
So right now she's at a netzero revenue.

(38:59):
We're not losing money, butwe're not also making money on
it.
She is paying herself, which Ifind that a lot of
entrepreneurial small businessowners have a tendency to ignore
.
That's super important thatthey do pay themselves as part
of this, but the fact that she'srunning at zero, we're okay
with that right now.
There will be a point wherewe're going to turn it into a
profit, but right now it's justkind of investing as much as we

(39:21):
can into the business to grow itwhen you think about looking
forward to it.

Speaker 2 (39:26):
you've got an incredible name of what you
built for yourself and yourcareer so far.

Speaker 1 (39:53):
But looking for the legacy that you want to be
leaving in the next few years,when you look back and say this
is my next big milestoneachievement, what stands out the
most in terms of something thatyou want to leave behind?
There's some, there's a okay,bear with me here, james there's
a, an incredible speaker that I, an incredible human being that
I met a number of years ago.
Um, now, I was born and raisedin canada and, uh, in in canada,
we have a Canadian footballleague, not football soccer, but
football, like Americanfootball.
Um, it's a second class sportin comparison to American
football.
Um, it's not overly I'm sure alot of Canadians will hate me

(40:15):
saying this, but it's not overlyloved in Canada.
Um, especially in Toronto,where we're used to having like
real high end teams, not not, uh, you know, kind of subpar teams
.
Um, anyway, he played for theToronto Argos for a number of
years and you'd think, okay,what is a stupid football player
going to say to you?
But he was actually one of themost intelligent, caring
individuals that I'd ever met inmy life and, um, beyond trying

(40:41):
and spending a lot of time withhim and ways that he impacted my
life, one of the things that healways said is kind of
resonated with me.
We are, we as employers, ascoaches, as managers, as mentors
, as as individuals.
Our goal, our legacy, should beto leave the world in a better
place than where it is when wecame in.
And you know the opportunitywhen.

(41:02):
You know when he, when he talksto managers or people that are
running businesses, you know hetalks about how our
responsibility is, you know, notjust to take care of ourselves
and our families and ourmortgages and our bills.
It is everyone that works foryou and all the people that they
care about.
Like you kind of have to havethat extension and that thought

(41:25):
that everything that we do inbusiness, we need to start
thinking about how it impactsall of those individuals.
You know.
So you have the people thatwork for you, but their partners
, spouses, husbands, wives,children you know they're almost
as important as your own fromthat perspective that you are
responsible for them.
And when you take thatresponsibility for them, it's
absolutely incredible what youcan build by caring about

(41:49):
everything and everyone aroundyou.
I'm a big believer that theuniverse is, you know, kind of
imbalanced and you give what youknow, give what you take out of
this and you know, I'mconstantly pouring more and more
into this universe and theuniverse arguably universe
arguably has taken very, verygood care of me and I'm I'm
ecstatic I lead a very, veryblessed life.
But I think it's because of thatbalance, like we continue to

(42:11):
push out into into the universe,share as much as you possibly
can, be sincere with everythingthat you're doing, care about
all the people around you thatbusiness will come to you.
People will recognize that,people will want to come and do
business with you, which willallow you to hire more people
and change more lives.
And, and you know, that's uh, Ithink you know, in my mind, at

(42:32):
the end of the day, if I havepeople that are, are, what's the
term?
It's saying like, uh, you know,be the, be the person that
people are saying nice thingsabout when you're not in the
room.
I think that's all I reallycare for at the end of all this.
I love it, rob.

Speaker 2 (42:48):
Well, look, thank you so much for taking the time
Just in closing.
For any aspiring leaders outthere that are on their journey
at the moment, they're lookingat how they can build their own
legacy, their own business,whatever that may be.
What tips or life lessons canyou share as a closing point?

Speaker 1 (43:08):
wow, that's a.
It's a big question, james, andthere's a million different
kind of things that kind offilter into it.
But give, just give, give asmuch as you can look for
opportunities to give.
You know, uh, the the universegives us these, these
opportunities where we cancontribute back to the greater
good.
You have to take advantage ofthem.
And again, I'm a big believerthat these things have a

(43:29):
tendency to come back and payoff, and I've seen it repeatedly
, repeatedly, repeatedly.
Where you do something kind forsomebody, whether they're an
existing customer of yours,whether they're giving you
dollars or not, and I, and uh,I'll leave it with this a
perfect story.
Um, we're in national tennessee, there's a hockey game that's
happening.
It's a really, really importanthockey game.

(43:50):
It's a playoff game and, uh,there's an msp there that is a
huge fan of the team that'scoming in and playing.
I particularly don't care aboutthem.
Um, so I have a set of veryexpensive tickets that I gave to
him and he's he was not acustomer of mine, but I knew he
was a fan of this team and likea massive fan, and I said no, no
, no, I want you to have thesetickets because I know you're a

(44:12):
fan.
I'm not interested.
I'm not going to get as muchpleasure enjoyment out of that
as you will.
And he's like.
He kept telling me I am notgoing to buy anything from you.
This is not you know.
Don't expect me to turn aroundtomorrow and start buying your
product.
I'm like.
It's not about that.
It's about you enjoying thisteam and getting more pleasure
out of this than I will.
Please take these tickets.

(44:33):
And he did.
And he did not buy anythingfrom me, probably for about five
years.
But you know what happened.
We became BFFs, best friends.
We have ongoing conversations.
He has long successfully exitedhis business and we continue to
have conversations to this day.
You know, we've always beenfriends as a result of these

(44:55):
gestures.
And again, you will find waysof making money and doing
business with these people overthe course of time just by being
kind, because you know peoplewant to rally around you and
want to see you succeed.
You live money and doingbusiness with these people over
the course of time just by beingkind, because you know people
want to rally around you andwant to see you succeed.
You live by this.
I know you live by this too I Ishare a similar philosophy.

Speaker 2 (45:11):
I'm a big advocate of the go-giver is trying to get
as much as you can and um, yeah,uh, do it selflessly.
But typically the universe umwill return something.
Um, not necessarily what, notnecessarily in the direction
that you thought it would comefrom, but typically it does come
back to you, rob, great.
Thank you so much.

(45:32):
It's been awesome to chat,great to see you again and
really appreciate your timetoday.

Speaker 1 (45:37):
Absolutely my pleasure, James.
Always good to see you, myfriend.
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