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Published on:

30th May 2025

Cold calling, ads, SEO... none of it worked

In this podcast, Ray reveals the real reason marketing strategies like cold calling, LinkedIn outreach, and paid ads fail for MSPs—and the mindset shift you need to make any of these strategies actually deliver results.

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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

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Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

Transcript
Speaker:

Hey Ray, do you think cold

calling will work for me?

2

:

Um, well, how about paid ads?

3

:

Like do you think paid ads would work

for us or about, how about LinkedIn?

4

:

Like if we're doing some content

and some prospecting, do you think

5

:

we could make LinkedIn work for us?

6

:

I get questions like this all the

time, and you know, from MSPs, from

7

:

other business owners who are trying

to make really good decisions about

8

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where to invest their time, their

focus, their money, their energy, but.

9

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They're asking the wrong question

because if you're in a B2B market

10

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and someone and I, and, and I mean

anyone and your entire industry is

11

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landing clients through a particular

strategy, then the answer is yes.

12

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Yes, it works.

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Cold calling, paid ads,

LinkedIn, all of it.

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Like the, the real question

is will you make it work?

15

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And that is really where

the game is won or lost.

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Because the truth is, most business owners

they, you know, dip their toes into new

17

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strategies without a real commitment

to making that strategy work, right?

18

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Like they're looking for the thing

that works instead of looking for the

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thing that they're going to make work.

20

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So they, they try cold

email for a few weeks.

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They throw up a landing

page and run some ads to it.

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They, uh, hire an SDR and let

them run for a couple of months.

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And you know, when they aren't blowing

up their calendar with new appointments

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and new clients in a really short period

of time, like they don't get the instant

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results that they're looking for.

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They just declare like the

whole strategy of failure.

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But most of the time it's

not the channel that failed.

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It's not the strategy that

failed, it's the approach.

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Um, and I'll, I'll, I'll

share a story with you.

30

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I was, uh, I was speaking.

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In Dallas at a, at an IT

event, uh, here recently.

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And I, I was talking to a guy named

Mark and, you know, Mark's got a

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$5 million MSP and we're talking,

and he knows that I have a, I

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have an SDR accelerator for MSPs.

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So we've got a program where we'll help

you find the right SDR, we'll help you,

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you know, manage them, train them, coach

them, and get them, you know, booking, you

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know, good appointments on your calendar.

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And as we're, you know, we're just talking

about the SDRs in general, and he, and

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he's like, well, you know, SDRs just,

they just don't work for my business.

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They never have.

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And you know, he, he went on to

tell him, he's like, you know, I've,

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I've hired a few over the years

and, you know, it's really, it's

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the same thing every time, Ray.

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It's a, it's a flop.

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Like, and he, he was convinced.

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That his business was different,

his market was different.

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And while we could see, you know,

success stories all over of people

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leveraging SDRs to book more meetings

and get more sales, like, it was

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just like, that doesn't apply to me.

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And I was curious.

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So like I, I started asking some questions

and I was like, well, like I'm curious

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Mark, like when you were looking.

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To hire SDRs, like what were

you actually looking for?

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Like, what were you looking for

in a new SDR to, to make sure

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it was like the right person?

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And he kinda shrugs and he is like, well,

you know, I mean it's it's entry level

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Ray, like, it's just, I was just really

looking for, for someone inexpensive

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to make some phone calls for us.

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And I was like.

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Okay.

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Um, I was like, well,

what were they pitching?

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You know, like, were they,

were you offering like a free

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cybersecurity assessment?

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Were you doing like a free

training for, for employees?

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Like on phishing?

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Were you like even a piece of content?

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Something?

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Nope.

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Uh, it was, he's like, no, like we were,

it was a 30 minute meeting with me.

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And I said, okay, and I'm, but

I'm, you know, I'm thinking, well

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that's, that's not a clear offer.

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That's like, there's no real hook to that.

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There's no real perceived value to that.

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Like unless somebody wanted to meet with

you or is exactly at the right time,

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right moment, like just pure serendipity.

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You, you happen to call.

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Um, that's not like a, that's,

that's not a great offer, frankly.

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Right.

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So, and I was like, okay, well, I

mean, were you doing any marketing

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when you had them calling?

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Were you doing any, you know,

any, any emails, any direct

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mail, anything like that?

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And he's like, nah, we actually, we

tried some emails before and, you

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know, nobody really opened emails.

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Like the, you know, the, the

open rate was something like 20%.

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And I figured, you know, if 80%

aren't opening, it's not worth it.

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He said, the.

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We did direct mail for a little while

and you know, we, nobody called us back.

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So we know nobody's really reading those.

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And I'm like, okay.

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And I'm just going through the

checklist in my mind, right?

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Like, what are the things that

an SDR needs to be successful?

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And I was like, okay, well what about

like the data that they were calling?

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I'm like, where were you getting the data?

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Did you have that, you know, cleaned?

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Like where, what was the source

of that, that, that list that

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they were basically calling?

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He's like, well, it was

a, it was from ZoomInfo.

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And I said, okay.

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Did you.

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Did you have that cleaned or verified or

like what work did you do to it before

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you loaded it up and started dialing?

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And he said, well, none.

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I said, okay.

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I said, okay, mark.

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I said, tell you what, what's,

when you were listening to

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calls, like, what did you hear?

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Why, why weren't they

booking appointments?

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Like, what was the reason they said no?

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Like, were you, was it not enough time?

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Was it not compelling offer?

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Like, what was it?

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And he said, well, we didn't really,

we didn't really do the call coaching.

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He said, I'm, you know, I'm not,

like, I don't have your background.

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I'm not a sales manager.

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So I wouldn't, I wouldn't know what

to change in the script if we did,

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you know, and I, and you can probably

guess where this is going, right?

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Like I, you know, as we, as we're talking.

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I can see just by the questions

that I'm asking him, I can see

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Mark start to like rethink.

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Hmm.

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Like maybe I should have done

some of these, or maybe I should

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have rethought some of these.

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And it wasn't like, I don't say this.

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To like, to, to paint

market a in a bad light.

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I say this because I see this a lot.

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Like this is actually really common.

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And it wasn't that SDRs don't work, right?

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It was that his approach

to doing it didn't work.

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And as we, you know, as we, as we

have, you know, a few more minutes

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of conversation, I said, okay,

well what did you do instead?

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Right?

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Like, you just, so you, you

abandoned that strategy.

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What did you do instead?

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And he said, well, you know, we've

done like a little bit of content.

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Uh, we've, we've dabbled in some, some

SEO we've, you know, done some, you know,

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some pay per click for, with, with Google.

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And I said, okay, any of

those, like a home run?

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None.

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He said, no, we haven't had

really any luck with any of 'em.

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And this is like tried and true.

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Like I, this again, I, I hear this

and see this all the time and it's,

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the strategy isn't the problem.

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Like Mark had gone through multiple

strategies and he'd kind of

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just like written each one off.

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Well, that one doesn't work for us.

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That one doesn't work for us.

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That one doesn't work for us.

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But the problem wasn't the

strategy itself, it was how

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he engaged those strategies.

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It was how he deployed those strategies.

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It was his patience and, um,

you know, the, the focus and the

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consistency and the iteration.

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Like he tried, it didn't work initially,

and he abandoned it and he, he never

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really committed to any one of these

things and he didn't stick around

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long enough to learn the thing.

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To be able to identify why isn't

this working so that I can start

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fixing it to make it work and build

something that will actually scale.

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And that's, that's exactly what I see.

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Countless MSPs, I'm telling you.

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And, and other businesses like jump

from strategy to strategy to strategy.

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I call it the perpetual pivot.

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Right?

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And it's like you're, you're

just hoping that the next one's

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gonna be the silver bullet.

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But the thing is, winning

strategies are not found.

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They are built.

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Like, and lemme say that again.

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Winning strategies are not found.

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They are built.

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Every one of these things

could work if you stick around

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long enough to learn them.

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Iterate, optimize and

make them work right.

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And, and you know, the thing is,

most of these strategies, if you do

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the math on some of these, you can

see 10 x returns right from you.

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Get a great SDR on the phone, give

'em a good list and, and offer and,

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and know, turn them loose with some

coaching, you can 10 x the investment.

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Right.

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Same thing with cold email.

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You know, like we and I, we've done

this, like you can do cold outreach and

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you can make that thing 10 x itself.

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You could do the same thing with paid ads.

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Like it's, most of these strategies

have a pretty significant ROI associated

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with them, but you don't get a really

big ROI like a 10 XROI from something

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that's gonna be plug and play.

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Right, like you get 10 XRI from

something that you got directional,

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you know, like strategy, but you're

gonna have to work at it, right?

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And you get that from structure, from

consistency, from iteration and from doing

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the work that most people avoid doing.

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Right.

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And, and when we talk about hard

work, most of the time we, we quantify

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it in terms of the number of hours

that are being worked, and we don't

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look at the qualitative component.

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Like hard work to me is actually doing

the stuff that most people avoid doing.

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Right, and it's this.

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It's saying, okay, I'm going to

stick with this and I'm going to

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do the things that are necessary to

make this damn thing work because

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everybody else is gonna abandon it.

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And like, for example, business owners

like who win at outbound, right?

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Like outbound's not easy.

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You know, but it, oh, it's insanely like

valuable to be able to build a client

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acquisition system to go get your own

clients, like cash is oxygen in your

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business, and the ability to go generate

your own sales without having to rely on

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an agency, without even having to rely

on algorithms and all of those things.

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If you can build outbound in your

business, it is insanely valuable.

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But people who win at outbounds,

they're not running perfect

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playbooks outta the gate.

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Right.

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Like they just go into it and say,

I'm gonna make this thing work.

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And they, and then they build the systems.

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They build the systems like, okay,

we're gonna get a good offer.

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We're going to figure out

how to dial in the list.

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We're gonna figure out how to get the

right people and get them trained up.

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We're going to get the right scripts

and build a good playbook for 'em.

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We're going to build the right systems

to coach them, to give feedback

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to, to iterate all of these things.

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And I would say that probably

the most important thing.

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For somebody that's gonna be effective

at outbound is they're just gonna

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go into it with the expectation

that I'm talking about, like the

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expectation that it's going to

take a minute to figure out, right?

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Like they're not gonna bounce

as soon as things get bumpy.

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They're not gonna get 30 days

into this thing and be like.

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Well, you know, we didn't 10 x

that, that investment like Ray said.

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So we're out, like we're gonna go try

the next thing and the next thing and

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the next thing and the next thing.

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'cause they all have the same learning

curve that's associated with it.

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Right?

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Um, like, so the people that will

win at this, like they're gonna

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solve one small problem at a time and

they're gonna trust that by treating

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it like the scientific method.

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If I keep doing this, if I keep tweaking

this and just finding the next constraint,

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fixing it, success is inevitable.

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Right.

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Like that mindset, that expectation

is what it takes to really succeed.

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And it's, and it's really what separates

the winners from everyone else.

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So, you know, if you're

saying, okay, Ray, I got it.

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Like how do I, how do

I make this actionable?

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Well, one, like pick your channel, right?

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Like pick your channel, pick your

strategy, whether it's gonna be cold

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email, whether it's gonna be cold calling,

whether it's gonna be paid ads, whether

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it's gonna be direct mail, whether

it's gonna be LinkedIn, whatever it is.

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Like they can all work.

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So.

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Pick the strategy, pick the channel,

and then two, commit to the long game.

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Right?

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Say like, I would say 12 months, like

say, I'm going to focus on this channel

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and I'm going to give it 12 months

because I'm committed to making it work

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and I know it can work, other people

are doing it, so I'm gonna commit to it.

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But at minimum, I would say six.

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Six months.

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Right?

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And then number three is,

you know, just look at that.

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And during that six months, you're only.

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Focus, your only job is to just find and

uncover all of these, the obstacles that

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are standing in your way to getting the,

the, the numbers that you want, right?

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So as soon as you start, you get

a few weeks in and you're like,

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okay, we're doing cold email

where nobody's opening the emails.

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Okay, are they getting delivered?

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Cool.

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If they're not like, let's, let's

look at, let's look at that.

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If they're getting delivered and

they're not getting opened, then

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let's look at the subject line.

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If they're getting delivered and

they're getting opened and they're

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not getting converted, just work

piece by piece by piece, and.

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And then four, I would

say like, get support.

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Like if you need it, if you're like,

if you want to fast track this, like

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if it's a game of learning how to

iterate piece by piece by piece.

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One thing that I've learned, uh, is,

that's a shortcut for all of these

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things is basically go out and find

somebody who's done it or who's

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doing it really well, or who I know

knows how to do this, has some like

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a track record associated with it.

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And hire them to teach me how to do it.

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How can I fast track this?

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Like, that's what we do.

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Like the, the SDR accelerator

that we have for, for MSPs.

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What we do is we, we've identified

all the things that we know are

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necessary to succeed, right?

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Like there's, there's a recruiting

process, there's a training com

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component to it, there's a, you

know, onboarding, there's a, uh,

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script component, there's a, you

know, uh, coaching and, and support.

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And we've put all these things

into that program to fast track it,

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but even if it's something else.

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Right.

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Like it's whatever that is,

go find an agency, go find a

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partner, go find another, I don't

know, another business, right.

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In a or another business in a

different market, and see if you can

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find a way to get the lessons without

having to get the scars, right.

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So it's like, you know, my, my best

advice is like, if you are, you know, I'm

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picturing like staring out at my backyard.

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Like if you're, if you're

standing at the pool and you're

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kinda like dipping your toe in.

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You know, like, I'm gonna try this,

I'm gonna try this, I'm gonna try this.

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And you're waiting to find a

strategy that just feels right.

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Like, oh, hey, this hit

right, it's not gonna happen.

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Right.

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They just, um, another way of looking

at this is, um, you know, it's like

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when we, when we think about people

who are overnight successes and you

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actually peel back and you go, holy cow.

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You know, like an overnight success

in music and then you realize.

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Wow.

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They have been playing in

bars for free for years.

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They have been hustling in, you know,

music clubs and they have been doing

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this, and they have been doing this, and

then it looks like an overnight success.

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Like, just think about it the same way.

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Right.

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And now it doesn't, it

doesn't have to take years.

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But you get, you get what I'm saying,

like the overnight success is not

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necessarily the overnight success.

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So you don't, you're not necessarily

like just dipping your toe in the

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water to find the thing, like that's

not being strategic, that's gambling.

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Right.

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And that's like, that's like looking

for and crossing your fingers

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that you're gonna get the one hit.

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Wonder like winning strategies

can all work, but only if you're

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willing to make them work.

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So pick one, commit to it, solve

the small problems along the

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way, and then just keep going.

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Until you get the

breakthrough that you want.

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That is the best piece of

advice that I can give you.

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And it's me speaking from experience,

and it's me speaking to myself, frankly,

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like as I have the same tendency, like

we are impatient, we wanna move quickly,

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we want to get results instantly.

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But that impatience can

also be a huge liability.

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So best advice, I hope it helps audios.

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About the Podcast

Repeatable Revenue
A podcast for MSPs and B2B business owners who want to scale sales.

Repeatable Revenue is hosted by Ray J. Green, an investor, entrepreneur, and strategic growth advisor to MSPs and B2B businesses. He's led national small business for the U.S. Chamber of Commerce, run turnarounds as a CEO for private equity groups, and advised 100s of MSPs and B2B businesses on how to build sales teams and scale sales from Cabo, where he now lives with his family.

This podcast is a collection of interviews, lessons learned, and other infotainment to help you build your business... and the best version of yourself.