The Freemium Formula: Converting Fear Into 10X Growth/Bill Macaitis - Slack, PLG, Pivots ~ Spark of Ages Ep 42 - Spark of Ages

Episode Transcript
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Rajiv Parikh (00:05):
Welcome to the Spark of Ages podcast.
Today we're sitting down withBill Macaitis, a true legend in
the SaaS world, who's been amarketing mastermind behind some
of the most explosive growthstories in tech history.
Bill's resume reads like agreatest hits album of hyper
growth companies.
He was the CMO and CRO at Slack, helping turn it into one of

(00:27):
the fastest growing businessapplications ever.
Before that, he was the CMO atZendesk, guiding him through
their IPO, and Bill served asSVP of marketing at Salesforce.
We're talking about a guy who'sbeen involved in five highly
successful tech exits.
That's not luck, that's pureskill.
These days, bill is just notresting on his laurels.

(00:47):
He's a growth and marketingadvisor for AI and SaaS
companies and runs SaaS CMO Pro,where he shares his expertise
with the next generation ofmarketing leaders.
He's become the go-to guru forproduct-led growth, a PLG.
Bill's core philosophy keep itbeautifully simple and always
put the customer at the centerof everything you do.

(01:08):
Before getting into tech, billgraduated from the Geis College
of Business at the University ofIllinois, Urbana-Champaign,
where he graduated with honorsand made the dean's list.
Some of the key takeaways youcan expect from this episode
We'll talk about product-ledgrowth as an enterprise strategy
, the importance of acustomer-centric approach and

(01:28):
beautifully simple software,holistic marketing metrics
beyond the funnel and, finally,the imperative of continuous
learning and adaptation.
Bill, welcome to the Spark ofAges.

Bill Macaitis (01:39):
Oh man, Thanks so much for having me.
That was crazy.
I think it's the first timeI've ever been introduced with
saying that, I made the Dean'slist and I think it was like one
semester I got straight A's.
That was pretty much it incollege.
The rest it was a little up anddown, but that was fun to bring
that in there.

Thanks so much, we had to find some nugget about
you that people don't know about, and that's what we found.

My mom will be happy that that was published.

Yes, this this is a podcast for your mom, good
deal.

Thank you, sir.

All right, let's start with one of the favorite
things you like talking about,which is PLG, and you've said
before that the PLG initiativeis one of the hardest things
you've ever done, which isinteresting, since the three
last companies that you talkabout so much and that you've
helped build success for arethose types of companies.
So what I'm interested inlearning about here is the
technical and organizationalhurdles.

(02:26):
So what are the most overlookedemotional or cultural
challenges that leaders andteams face when trying to pivot
an entire organization towardsPLG?
And then, how do you fosterresilience during that
incredibly profound shift?

Yeah, yeah, it's a tough motion, right.
You know, we had a lot ofsuccess with it at Slack,
zendesk, salesforce, and when Ikind of wrapped up those tours
of duty, I was like, what do Ido next in life?
And I was like, you know,become a VC?
And I'm like, oh, there's amillion of those.
But at least when I was goingthrough my operator journey
there weren't as many advisorsthat could come in and help out.
So that's what I do now withtheir go-to-market grow faster.

(03:02):
And I say it's hard because fora lot of companies that have
gone down the SOG path orsales-led growth path, pivoting
to a PLG motion is verydifficult.
It's difficult on a number oflevels.
I think one is just evengetting what product-led growth
is right.
Maybe we start there right.

Yeah, yeah, that's great.
That's actually a great way togo.

Yeah, because I think a lot of people there's
just a lot of misinformation orpeople think different things,
right?
Like I worked with one companywho was like hey, we've made a
ton of progress on PLG, we havea trial, and I was like, okay,
like that's great, that's likeone element of it, but there's a
lot to it.
So like, philosophically, theabout it is PLG is this idea

(03:46):
that people are spending moreand more of their time in the
product itself.
It's that simple, right.
And then how do you infuse yourmarketing into the product,
your sales instead of product,your support, your success into
the product?
Right, and that's where it gets, you know, a little more
complicated, right, because nowyou're going down high velocity
motions.
You're doing things likeproduct qualified leads.
You know you have freemiummodels, different pricing and
packaging.
You're thinking about theadoption.

(04:07):
You're thinking about howsimple it is to use.
You're thinking about thingslike net promoter score.
How many people are actuallyusing the product, like DAU.
So it's a wide area and it'sdifficult because, especially if
you've done the SOG path andespecially if you're a couple
series up there right, so ifyou're in series C, d, e, f,
whatever it is right A lot ofthe culture is built around the

(04:28):
traditional sales model, whichis all right.
Let's do outbound, you know,let's bring in a lot of leads,
let's hand them all off to salesand marketing will run away and
you know, hopefully we'll hitour quarter.
And like the PLG model, it'sjust so different, like there's
totally different metrics.
Like I said, there's thingslike DAUs, you know, product
qualified leads, net promoterscore very different than a

(04:49):
traditional SLG company.
You know, I think culturally, alot of people worry about some
of the key tenants of PLG, right.
So freemium I'm a huge advocateof freemium, like you kind of
did a nice intro with the Slacksalesperson, this but before I
did 15 years on the B2C side andI've done almost 30 years of
online startups and every singleone I've had a freemium model
right.
And so for me it's like oh yeah, of course you do.

(05:09):
There's all these benefits,higher growth, and it's not.
But for a lot of people freemiumis scary.
It's like, oh, what does thatimpact my quota, you know?
Oh, my God, like I can nolonger sell there.
They keep pushing me up market.
There's just a lot of likefears around it and once you've

(05:31):
already invested in a certainmodel, a sales and growth model.
It's very hard to pivot.
Now the new SaaS and AIstartups like it's amazing like
73% of them have adopted POG, solike that is the dominant model
coming out.
But for a lot of companies thatare pivoting to it, it's a
tough one.
And it's tough from just allthe different elements you need
to do.
But just really culturally,like I found like that's the

(05:54):
hardest thing.
You really have to get, youknow the board behind it, you
have to get the C-suite behindit, the founders behind it,
sales behind it, productmarketing there's all these
teams that really have to buyinto it if it's going to be
successful.

Is this one of those things where you have to
be more top-down led, where it'scoming from senior management
and then they have to create aseparate group that goes off and
does this, or have you found it?
Sometimes it's bottom-up orit's engineers wanting to build
something or it's a group offolks wanting to do something on
their own?
As part of this, when you'retalking about it, you mentioned,

(06:27):
like there's you know, series,you know CEF.
Those companies are pretty faralong and they've built a level
of ARR and growth Otherwise itwouldn't be at that level.
So for them it must be hard,because there's an ingrained
culture, to shift to Earlier.
I guess they're in moreexperimental mode and they're
willing to try new things.
What are some couple key pointsthat you find that stick out

(06:47):
for you on that?

So one to kind of answer your question, I
probably worked with, you know,30 plus different startups on
either building PLG for thefirst time and doing it the
right way, or pivoting to it.
And I would say, you know, froma pattern recognition
standpoint, I will say the onesthat have the hardest times are
the ones that are further, likeI said, in the series C, d, e, f
type size, but also the onesthat just assign a tiger team to
it, like that.

(07:13):
That's the one that I find likehas the hardest time.
You know, I found one companythey were struggling with their
POG motion and I'm like walk methrough, what have you done so
far?
And they're like well, we haveone guy working on it.
You know he's, he's remote,he's over here.
We have another thousand peoplesalespeople doing this.
And I'm like, well, you knowthat's that's going to be tough
too when you just have oneperson one speedboat and one

(07:34):
tanker.

Right, yeah, totally.

I do find, like the ones that have a lot of
success from just a practicalstandpoint, is one, you know,
starting to use PLG metrics.
We talked about that like PQLdaily active users, product
qualified leads, and that's adifferent model, right?
So the old model was you wouldjust someone come in, fill out a
form and they go straight tosales.
And the new model you get themstraight into the product, you

(07:56):
wait for some certain thresholdsof product activity and then
the sales goes in.
Right, so it's a qualified andit's product.
And so I found it's best toadopt some of those metrics and
then best to really have this asa company-wide initiative.
Right?
Because really to make itsuccessful, you have to have
product focusing on it, you haveto have marketing focusing on
it, you have to have salesfocusing on it Right?

I think you've talked about this in some of
your videos.
You just can't take yourexisting product and say oh you
know, go play with it Right,cause usually most enterprise
level products have trainingassociated you have customer
success associated, yeah, awhole onboarding process, and
now you're basically saying putit in the damn product.

I'll put it another way.
Most enterprise products suck.
They're really hard to use.

I got to tell you from my experience, when we've
when we've tried to do itinternally, where we've taken
our tools and we've started withan enterprise product.
I have a pretty good sizemarketing team that does the
work.
If the interface sucks, theyjust won't use it Totally.

Right.

I can't force them , like other companies that have
big operational teams.
They just won't use it.
They'll just find other waysaround it.

Yeah, and that's a huge, huge part of a POG
motion too, and why some ofthese later companies have a
hard time pivoting into it isthat typical enterprise sales
motion is all about features.
I need this feature, thisfeature, this feature, this
feature, big feature, rack ofthings.
Totally right, we look great onour checklist right.

So what if the feature sucks?

Yeah, and the more features you add, the
harder it is to use, right?
So you know you have thisreally hard to use product and a
big part of a POG motion ismaking it simple and easy to use
, right.
So I advocate for things likehey, after someone onboarded
with you, give them a littlelike, hey, how easy was it to
use a thumbs up, thumbs down?
Right, yeah, if you have 17%thumbs up, ok, our quarter next

(09:37):
goal is to get that up to 30%and then the 40%, whatever.
It is Right but Right.
But a very different model likeproduct is used to building
features and a POG motion.
You're trying to make it simple, easy to use.

So one of the things you have to do is you
have to instrument the product.

Absolutely.

So if you're not in the product itself like
you're talking about, havingthose thumbs up, thumbs down
capabilities in the product,which is not an enterprise thing
If you don't have, then you'rejust not.
And then, off of that, ifyou're doing it well, you're
actually kicking off campaignsand notifications to totally
other insights.

Teams are working cross-functionally.
So a lot of times, too, likethis isn't just product right
Like a lot of time at Slack, themarketing team spent a ton of
time in the product right andyou know, what we would do is we
would rewrite all the back enddeveloper dialogue and prompts
that they wrote and make it morefun and easy to understand.
We would put in Easter eggs.
We would, you know, religiouslygo through the onboarding flow,

(10:27):
the signup flow for a lot ofenterprise companies, like the
signup feature, like was builtlike 11 years ago, right, and
none of the execs have gonethrough the signup process in a
decade, right, and they justthey don't know, like, and they
don't realize, like how hard itis to learn this totally new UI
and taxonomy.
And I think ultimately, likeyou know, kind of getting down

(10:48):
to the brass tacks.
It's like having these teamswork together, you know, having
it be a company-wide initiative,having the right metrics,
having an advisor or justsomeone who's done it, you know
that can come in and help themwith that.

So how do you make that flip happen?
Because now you're saying theentire company has to work on
this together.
A lot of times your productdesigners are probably not the
right people, or they need orthey have to be open to help
from someone that knows this wayof doing this, this more
Duolingo style or entertainmentstyle way of using a product.

Yeah, b2c style right.

Yeah, how do you think about that when you're
coming in in that situation?
Is this a senior level person,you know, getting crap from the
the board saying this issomething you got to look at, or
they've gone to some events,that they've seen some things
and said, wow, compared to thesefirms, I'm falling behind.
Or is it something more organicthan that?

Yeah, I think the impetus usually comes from the
board.
Right, the board is like saying, hey, if we want to go IPO, we
need this level of capitalefficiency, this level of growth
.
We're not there.
We think PLG can helpaccelerate that, or even just
more capital efficient.
Right Like I work with someorgs and it's like my God
they're using like humansalespeople to sell to $5,000

(11:56):
and less ASPs.
Right, and it's like the uniteconomics are just so hard to
make that model work.
Right Like you need a highvelocity of that.
So usually pressure from theboard comes in.
I think the CEO or the foundersthen, you know, want to try to
move something like this.
Right, so sometimes I'll bringan advisor like myself.
But even the DNA of the company, though.
Right Like I'm a big fan oflike hey, hire some B2C people.

(12:17):
Right, cause, like they kind oflive and die by that.
Like you can't have a consumerapp that's super hard to use.
There is no model where you canhave 10,000 customer success
people training every singleperson to use your app.

Right, it just doesn't work, right yeah.

Or even, like you know, it was funny like Stuart
and I from Slack he was thefounder there we both had a
gaming background Right, and sowe kind of understood, like in
these, even these enterprise wasoriginally going to be a gaming
.
It was going to be a game,right.

He comes from blogger right, which is a very
much very much of a consumerblogger flicker consumer.

And so we we spent a lot of time making, you
know, slack fun to use, right,because if it's fun, people use
it.
So we spent a lot of time onlike hey, like our most
successful integration you'dfind this hilarious.
It wasn't like HubSpot orMarketo or Salesforce, it was
Giphy, like everyone wanted touse, like the automated Giphy.
We had a message loading of theday.

(13:12):
You know we had an emojisupport.
That was huge, you know.
It was like all these funthings that matters, right.
If your product is like justpainful to use, it's not fun at
all, of course people aren'tgoing to use it, they're not
going to recommend it, they'renot going to talk about it.
So like it's a very differentplaybook.
And that's just why I say likeit's a little bit hard, right,
like if you're going to, youknow, go down that path.

You're saying, when you're going to do this,
you better really commit.
Yeah, and you have to align theteam, you have to change your
metrics and how this works, andI'll tell you.
Here's something interestinghow did I get my company to move
off of emails and other chatapplications to Slack?
I couldn't get people to move.

Oh, it's hard.

CEO of a couple hundred person company should be
able to get shit done.
So no, what we did was in oneof our larger offices every day
we have a snack in the eveningsthat people go to the cafeteria
to eat, and we found that thatworked better than giving out
free lunch, free dinner, becauseeverybody had such weird diets.
So I said we are not going tosend out another email about
this.
You're going to put this onSlack.

(14:18):
And so they every day wouldpublish that on Slack.
And then the other thing theydid was for birthdays.
They created a celebrationchannel and then you get
celebrated on your birthday.
So that drove adoption morethan company-wide announcements.
Team-based, client-basedinitiatives that's what worked.

Isn't that funny.
Yeah, it's the little thingsand I mean you hit it on the
head right, like half the stuffwith PLG or really any new
initiative, right, like AI is ahuge one.
How would you embed AI in thecompany?
It's more of a changemanagement exercise.
I found it's less hard figuringout, like what do you do with
PLG and the steps.
It's a little difficult, buthey, I can lay it out pretty
easily.
Like what's more challengeslike how do you transform a 300

(14:58):
person organization, a 5,000 to10,000 person organization, to
really like buying in andunderstanding, like how this can
still help out your growthrates and be more capital
efficient.

So you totally.
You led me right to my nextquestion, which is all about AI,
right?
So you're obviously a fan of AI, I'm sure you're using it even
as part of your advisory service.

Yeah, absolutely.

Doing all these amazing content pieces that
you're doing, and you've talkedabout PLG landmines.
So what are PLG landmines like?
Poor onboarding, lack ofproduct stickiness, internal
misalignment that AI, in itscurrent and near future state,
is uniquely positioned to solveor significantly mitigate,
perhaps in ways that traditionalmethods don't or cannot.

AI is transforming every single
element of businesses right nowand I am a full fan of it, right
, and I think it's incrediblypowerful.
There's still a lot of hiccupsnow that anyone will see it'll
hallucinate or just maybe not godown the right path, and you
know part of choosing the rightmodel and the right base LLM but
I do think it's going to helpevery area right.
Including PLG like a huge thingthat allows now is more

(16:00):
different pricing models, right.
So I mentioned I'm a huge fanof freemium.
A big model that is becomingmuch more common now is
outcome-based pricing right, andthat's being kind of enabled by
AI in a PLG model to where youbasically say, hey, we're all
getting in charge on asuccessful outcome for your
business, right.
So if you're in customersupport, for instance,

(16:22):
historically it was oh you'd payfor you know per seat how many
you know customer support agentsyou had, or maybe it's just
some giant licensing fee and youcan't do that as much anymore
if you have a whole bunch ofnon-human agents.
Non-human agents right, so itforced like we had to evolve,
right.
And so now you're seeing, hey,it's being priced per successful
resolution right so IntercomSalesforce resolution right so
Intercom Salesforce a bunch ofthe pure AI companies are

(16:45):
adopting towards that.
I think that's a really coolthing.
I think another cool thing thatAI is enabling is
personalization at scale.
In the past it was justimpossible to provide the level
of personalization and thatcould be on the outreach side,
that could be on the onboardingside, that could be within the
product itself.
But AI is enabling huge amountsof advancements there the
targeting, the content, thevideo, just every single element

(17:11):
.
Right, Like.
It's hard for me, as a formerCMO, to think of any individual
team I had that is not being,you know, completely changed in
how they do their work.
That's right, and the power ofit.
So, yeah, I'm a huge fan and Ithink this, you know, movement
is here to stay.

So, yeah, so like you, I sat with some of one of
my clients.
It's a pretty good size.
I think it's like series E orF1 integration firm who will be
nameless.
Amazing people have.
Some of them have been on theshow and they.
That was the number one topicof conversation when we were
talking about AI and agentic AIis what do I do with the pricing

(17:40):
model?
It's a huge issue and evenoutcome is hard.
We're trying to do this with us, which is we have outcome for
our services right In a sense,like I deliver a website or I
deliver this content or Ideliver certain results for the
campaigns that I run, but somethings are by the hour and I
think AI gives us theopportunity to actually charge

(18:02):
based on an outcome and asuccessful outcome and finding
that well and verifying it, andthere's a lot of opportunity
there and I love your pointabout personalization.
I mean this, I think, is thegreatest opportunity for
marketers to truly go toone-to-one marketing.

Absolutely.

Marketing and sales in many ways merge,
because a lot of times themarketer creates the strategy
and creates the headline and thethrust of what they're supposed
to do, and then sales executesit.

But if I have, a bunch of agents doing it.
Yeah, yeah, there's a lot oflike, what's going to happen,
right, like I've always thoughtkind of philosophically like
marketing is just kind ofautomated sales.
Yeah, you know, we build thesecampaigns, we're doing a lot of,
you know, advertising,messaging, high velocity type
stuff.
But I mean it's going to befascinating, right Like.
I think the pessimist in me islike, oh my God, like every
single job in white collar landis like going away, except for

(18:54):
maybe some generalists that knowhow to run all this stuff
together.
The optimist in me because Ihave a daughter and I want her
to grow up in a, you know, agood world is that, like man,
the barriers to entry tocreating new businesses are just
tumbling down and you know shewill have access to you know,
hey, she's not a legal expertGreat, she's got a legal agent,
right.
Or she's got a sales agent or amarketing agent or hr, all

(19:16):
these ones.
And not only that, the pricesare coming way down, right, with
all this new competition, yeah,um, and the iting more
efficiently.
So I'm hoping that it spurs awhole bunch of new businesses
and new landscape.

But I know, every time a new technology comes,
it's always scary, righteverybody's always scared, but
they were scared during theinternet, right when the
internet first came out likeeverything changed I think it's
this thing where we can'tenvision the unknown and we have
to just trust economics andtrust that people have to buy
things.
Robots can buy things, butrobots can't.

Yeah, they can't go on vacation.
Not everyone has $10,000 towork with a lawyer, right, or
can hire expensive sales.
I think it's a good thingoverall.

I know we're going a little bit away from
marketing, but when my son wasgraduating from law school, his
dean of the law school said oneof the things AI.
There's a concern that we'llget rid of lawyers, but actually
legal filings will be easier todo for folks that don't have
easy access to lawyers, so nowthey can actually get, they can
redress their grievances throughthe legal system in a way that

(20:21):
they couldn't.
So maybe AI can help changethings for the better in ways
that we just haven't thought of.

Yeah, democratize it Definitely.

Okay, so going a little bit away from AI, but
kind of staying with it.
This is a hot topic among CMOs.
Right that a lot of them haveobjectives where they have to
source leads.
Right, or even source MQLs.
You know John Miller reallywell.
He'll go crazy over that right.
He's like I created.
You know, with Marketo Icreated this machine where

(20:48):
marketers turn into MQLgenerators, when really
marketers are supposed to bemuch more about building a
market right and much more aboutdriving the overall system,
working hand in hand with sales.
So in a PLG world, are therespecific product-led features or
experiences that help marketersand sales work more effectively

(21:09):
together?
How do they integrate in this?

Yeah, yeah, it's a great question, right, and I
know, john.
Well, we just did a big B2Bindustry marketing benchmark
survey and so we were.
You know it was fun to kind ofpublishing that.
But yeah, I think, ultimately,like you know, these teams can
and should work together.
I think, like, fundamentally,like how B2B splits up marketing
and sales is just based offlike a 30 year old relic go to

(21:33):
market model that's gottenreally old and dusty and it
hasn't been updated.
And, look, I think marketersshould be focusing in every
single stage of the journey,right From prospect to lead to
opportunity, to close business,to expansion, to going in new
product lines, right, like everysingle element of that

(21:54):
marketing could be in therehelping out, right, and also
sales, too, right.
Like I think they have a partof that journey.
These teams need to worktogether.
I think the PLG model is a muchmore efficient model, right, so
we talked about that earlier.
Like this old model where youcome in as a visitor, you just
see some form that you want toaccess piece of content.
You fill out the form.
All of a sudden sales startscalling you way too early.

(22:17):
You're not ready.
It's a bad experience when thenew model is like hey, you come
in, create this tent, they landthere, they go straight into the
product.
Maybe there's a freemium model,very low friction.
They're experiencing valuequickly.
Now you have a concept of aproduct qualified lead.
All right, it came from thiscompany.
We historically sell well intothis vertical.
They've passed this usage.
Hey, now sales is going toreach out much easier sell.

(22:39):
You know they're already usingthe product, they like it.
You have some internaladvocates already there.
But you know that just meansthat these teams need to work a
little bit differently and worktogether.

Right.
Are these metrics like sharedmetrics then?

I do, yeah, I'm I'm a big advocate and I think,
john as well as like of havingshared metrics Right.
So I think when, when youcreate a model where marketing
is just in charge of like leadsand then sales in charge of the
rest, it just creates friction.

It's just warfare.
It's open warfare between eachother.
Yeah.

Put them on the same goal.
Now you could argue it's afunnel based goal and that's
fine.
I would argue, funnel basedgoal.
So when I say funnel basedbased, I'm like leads pipe, closed
business.
Funnel-based goals, in my mind,encourage very short-term
behavior.
Right, we have to hit next week, we have to hit next month.
It encourages you to lockeverything down, use bad sales
tactics, promise features thatdon't exist.

(23:27):
Right, just do whatever you canto get the sale right.
Like I think it's a little bitsmarter to think more long range
.
So in the product like growthworld you are thinking about
daily active users, are peopleactually using the product?
Do people actually like theproduct?
You know?
Are they past a certainthreshold?
But I also think, like, likebrand stuff right.
Like, hey, what is aided recallsentiments share voice.

Right.
So.
So now you're, now you'regetting into Brett, so these are
soft PLG sorts of metrics,right so?
so when I when I'm doing the PLGit's not just, it is daily
active users, product qualifiedleads and, of course, I'm sure
you would say this is for myideal customer profile right,
because sometimes PLG leads youto get a customer that you

(24:09):
actually won't get revenue from.
I'd love to hear your point ofview on that, because I ran into
that situation in my owncompany.
But then takes you to the softones that you're talking about,
like brand affinity.
Or is it share of voice?
Are we still in the share ofvoice?
Aided unaided Are we stilldoing that?

You know there's a whole host of brand metrics
out there.
I would just say this A lot ofcompanies that I've worked with
on the B2B side are trackingzero brand metrics.
Yeah, right, and I just thinkthat coming from the consumer
side, like hey brand, is kind ofa long term leading indicator.
Right Again, if you only focuson short term demand gen, you're
not building up any type ofaffinity, you're not building up
awareness.

(24:47):
A really common thing thatstartups will come to me is the
founder will go like hey, I loveour product.
We've got like 15 customers,but no one knows about us
product.
We've got like 15 customers butno one knows about us.
Right, like you know and hey,that's that's kind of an issue
of sometimes the metrics there.

It's the hardest way to walk into, the hardest
way to grow Like I mean, you gotto go in and explain who the
hell you are and and they'recoming in skeptically and, as
you know, Bill, like now intoday's world, where people
expect to interact with theirproduct, their consumer products
, they like to find you beforethey find them.
I think what for?

exactly the last.

Forrester event.

They're saying depending on whether you're a
Gen X, millennial Gen Z, you'regoing between 60 and 80% of
people who find you before youfind them.
Oh, I've heard that even 80, 90%, you know, depending on the,
you know the analysts puttingthat out there.
So, yeah, I mean this, theentire buying model has changed,
right, and I think, at the endof the day, kind of

(25:38):
understanding how thesedifferent models you know,
product led growth, sales likegrowth there's also like product
led sales which I like andthat's I'm a big advocate of is
like, hey, get them in, get theminto the product, right, and
obviously you have to do yourhomework, do the right ICP, do
the right marketing, so you'rebringing in the right people but
then, like you know, you scoreit and then sales reaches out to
them, right, but sales doesn'treach out to everyone because

(25:58):
salespeople are very expensiveand you want to only have them
reach out to the right ones.
Much shorter deal cycle.
Now the, the people that don'tbuy.
I'm actually like I have apretty strong point of view on
this.
So I've done a couple of videoson SESCMO pro.
By the way, if anyone wants towatch these videos, just go to
CMO procom and you'll, you'llsee all of them.

I'm a big advocate .
I love, I love what you've done.
You've made it super easy forpeople to understand.
You've done a great job withyour YouTube shorts that then
lead you to these somewhatlonger and then much longer
episodes, which are chock fullof great information.

Thank you so much man, like I try to make them
simple and fun, right.
You know just anyone that canwants to learn about this stuff
here.
But anyway, like I'm a big, soI've done a really long video
just on freemium because I'msuper passionate about it.
And the best way that I like tothink about freemium and people
coming in that maybe aren'twilling to pay is that it kind
of goes back to the earlierdiscussion with the POG and the

(26:51):
board.
Right, the board investors,wall Street, wants capital,
efficient growth engines.
Right, they want fast growingcompanies that have the right
margins, that are profitable.
So you have this spectrum of howdo you achieve this growth?
Right, and there's some oldschool models which is like
we're going to just do outboundsales.
There's inbound sales, there'soutbound marketing campaigns,

(27:12):
there's inbound marketing, seocontent and there's like PLG and
word of mouth.
Right, the more you go downthat spectrum, the more capital
efficient it gets.
Now freemium is a really goodexample of it's kind of a
mindset.
So at Slack, we had millions offree users, right Like 10
million free users, and somepeople look at that and go, oh
my God, I have 10 million peoplethat I have to pay bandwidth

(27:33):
for and support and there is acost associated with everyone
that's free users.
I looked at it as like wow, mymarketing team at Slack is 10
million.

Like I have a 10 million strong marketing team,
especially if they're using it,right yes, not just listed or
signed up If they're actuallyusing it.
This is freaking amazing.

Yeah, absolutely Right.
And so I always looked at it aslike hey, because sometimes
when you get the pricing andpackaging, like, I never liked a
free trial because it'sbasically saying, hey, we have
all these free marketers, but atsome point we fire them Right,
you hit the 30 day trial, youcan no longer use the product,
you're all fired Right and inlieu of that.
So if you don't have a freemiumplan, what a lot of times will

(28:11):
happen is it's like OK,marketing, we need you to go get
10 million DAUs.
Okay, I can do that, I can runmy YouTube ads, I can run my
billboard ads, I can do all this.
But hey, that costs someserious dollars.
So let's compare those dollarsversus the dollars of the
bandwidth, the support costs forthe free user, and usually it's
significantly less.
So I like the freemium modelsfor those that want to like

(28:33):
dominate their category, likereally win the awareness battle.
That's huge battle for it.
Also, what you'll find is likeSMBs are historically super
price sensitive.
A lot of SMBs just aren't goingto pay you regardless, but
there's a ton of SMBs out thereand they move jobs, they move to
different companies, they havefriends of different company
sizes, right.
So, like I always was on themodel of like, have a freemium

(28:54):
model, get the awarenessbenefits but then sell to the
enterprise and that's where youmake your money right On these
higher plans.

And then would you do that as part of your
segmentation or your reporting,saying, okay, yes, I have 10
million and I know of this I'mgoing to get a much smaller
amount that actually pay and acertain amount that.
Then you know, we did this witha bunch of clients of ours and
then a certain amount is goingto be enterprise, and so you're
presenting this model and thenyou're showing it with multiple
lenses.
One is just pure demand gen forenterprise, but the other one

(29:23):
is brand awareness, theirmobility to other places, their
word of mouth association, maybesales velocity.
Right, you could probably do itthat way.

Yeah, sales velocity, and also it does
having a freem mail.
On a weird way it opens up alot of land and expand for
enterprises Right.
Like when we were at Slack, wewould constantly have the
scenarios where some teams likeIBM and Southeast Asia, the
design team, started using usRight and then it started to
spread on the free plan, then itspread to another team, another
team, another team Right, allon free plans and eventually

(29:54):
like, oh well, we want toupgrade, we want to have one
bill, we want to haveconsolidated reporting, we want
to have SSO for all these teamsright Admin settings.
So then they come to you, thenthey come to us, right, or we
would reach out to them too.
Sometimes it could be eitherscenario there.

So now we're talking about this with the
disruption of AI.
So you have this wholesituation Like you talked about.
I mean, chatgpt is a classicChatGPT Cloud Gemini classic
examples of pure freemium-basedstrategies where it's pretty
expensive to generate an image.
Right, I think we saw thatthing about ChatGPT saying hey,
maybe chill out on the what isit called Ghibli generation.

Studio Ghiblis.

How should companies rethink their
long-term go-to-market strategy?
How should companies rethinktheir long-term go-to-market
strategy so they're looking tobuild resilience, adaptability,
relevance, where go-to-marketfunctions may be completely
redefined by AI, it's more thanshort-term gains.
What does a future-proofgo-to-market look like from your
perspective.

I don't know if there's any future-proof
go-to-market.
I mean, I always try to look atit as like.
For me, go to market is alwaysevolving and improving and
adapting and iterating.
Right, like, if you're a CTO,you get fired.
If you're like you know, we'rejust going to use the same
coding language we did 20 yearsago C++ that's great, we're
going to use it everywhere.
Right, they're like what?
But a lot of times they go tomarket Literally you hire this

(31:22):
person, they're like we, we'regonna use the same classic
go-to-market model I've beenusing for the last 30 years.
It works, damn it, it'soutbound, right, I don't like,
hey, I love product like growth,I love product like sales.
I have freemium models.
But it's always iterating, it'salways evolving.
And I will say you seecompanies that have adopted the
right go-to-market model, like acursor, for example, you know,
on the dev side with ai, youknow brilliant, 100 million and
just like I.

I didn't even know about cursor till I last
visited my operations team andthey're like, oh yeah, and
before I was like, hey, how'sthat get github, uh, copilot.
They're like, oh, we've already, we have that in cursor.

And totally here's the context by which you
use either yeah, it's amazinghigh velocity freemium model.
A lot of these startups, too.
I just started working withanother ai startup that you know
.
They're in the lean model, leanmodel.
So they're like hey, they onlyhave 13 people, 20 million ARR,
right.
So you really have to thinkabout.
Like, hey, how is what is thecapital efficiency of these
different models?
And they do make a hugedifference.
Like the go-to-market model youchoose has huge, huge

(32:09):
implications.
The pricing and packaging youuse premium product, like growth
, like there's all thesedifferent elements that can just
really make it.
And I think I'm a big believer.
Like, hey, adopt the AI tools.
Now, the pricing, the adoption,the personalization these are
ones that are just going to giveyou force, function,
improvements and essentiallymake that go to market.
Just modern, best of breed,moving forward.

Totally agree.
It's like learn or die, right,get in or get wiped out.
So I'm with you 100% on this.
All right, bill, this wastremendous amount of insight.
You've packed so much into areally short amount of time, so
now it's time to really testyour skills.
We're going to go to the sparktank.
So let me lay it out for you,Bill, Welcome to the spark tank

(32:51):
where business legends facetheir ultimate test, and today
we're putting decades ofstrategic thinking to the
crucible.
Today we're thrilled to haveBill Macedus join us, a man
who's been studying businesslonger than most people have
been alive and has the trackrecord to prove that all that
childhood fortune magazinereading actually paid off.

(33:11):
Tonight we're putting all thataccumulated business wisdom to
the test with the ultimate pivotpoint challenge.

Wow Okay.

We're going to drop you into the most crucial
decision moments in businesshistory, those make or break
crossroads where companieseither soar to legendary status
or became a cautionary tale in atough Harvard Business School
case study.
Here's how it works I'lldescribe a famous company at a
crucial decision point, withoutnaming them, and you'll need to
identify the company and predictwhat they should do next.

(33:42):
Then we'll reveal what actuallyhappened, to see if your
strategic instincts match upwith business history.
So, bill, are you ready toprove that your business pattern
recognition is as legendary asyour growth track record?

This is crazy.
I've never done this, but let'sdo it, man, this sounds fun.

All right.
Well, that's why we had youhere, bill, just to set you up
for this.
All right, here's scenario oneYou're running a scrappy
software company when the mostpowerful name in business calls.
They're secretly building theirfirst personal computer and
desperately in need of anoperating system.
The giant offers you a choiceSell them the operating system

(34:19):
outright for immediate cash thatwould solve all your money
problems or demand ongoingroyalties for every machine sold
.
This hardware giant has neverfailed at anything, but personal
computers are unchartedterritory.
What's your move?
A sell the operating system fora large lump sum.
B license the operating systemfor a royalty on each computer

(34:40):
sold.
C decline the deal and focus onyour own hardware ambitions and
this is if you're reallythinking for.
D open source your operatingsystem to build a community and
attract more partners.

All right.
Well, if my history is right, Ibelieve this is Steve Jobs and
Apple being approached by BillGates from Microsoft, and I'm
pretty sure they went C, whichwas a pretty gutsy decision at
the time, but obviously playedout well, with an integrated
hardware and software offering.

How about if I play a part of it back to you?
And see if you change youranswer.
You're a scrappy softwarecompany when the most powerful
name in business calls they'resecretly building their first
personal computer anddesperately need of an operating
system.

Is this Microsoft and IBM?
Oh, my God, okay, and so theyoh, I thought it was because you
said it was a cool softwaresystem.
So I thought it was the GUIthat Apple had.
Oh, I got you, I got you here,License right.

Yeah, there you go .

Boom, and a deck of corn was born.

Yeah, that's right and is just ridiculous today.
So the company is Microsoft.
Bill Gates, I think.
He bought DR-DOS for $64,000,then said he had it.
He with his good buddy PaulAllen then said he had it.
He with his good buddy PaulAllen went out and they sold it
to IBM and they had the IBM PCand he chose to license the OS

(35:56):
to IBM MS-DOS to IBM rather thansell it outright.
And it allowed Microsoft tolicense the OS to other PC
makers as well.
Ibm did not restrict them, eventhough they wanted to, fueling
a meteoric rise and dominance inthe software industry.

That's a good one , two fueling a meteoric rise
and dominance in the softwareindustry.
That's a good one, yeah, okay.

So Bill Gates and Paul Allen at the time, all
right.
So here's number two.
This one's going to be a littleharder.
You're leading a tech startupthat assigns three word
addresses to every three squaremeters on earth.
After launching in threecountries, the results are mixed
.
In Mongolia, nomads find ituseful, but don't pay.
In Germany, automakers licenseit for their navigation systems,
but growth is slow.
In the UK, adoption is nearzero, despite marketing aimed at

(36:38):
consumers and businesses forvehicle breakdowns and accidents
.
With cash running low, you mustchoose a survival strategy A
double down on Mongolia,refining the product for nomadic
communities.
B focus on Germany's autoindustry, betting on luxury car
partnerships.
C pivot to emergency servicesin the UK, positioning it as a

(36:58):
life-saving tool.
Or.
D abandon all markets and opensource the technology.

I feel confident saying doubling down on the
market in Mongolia.
I don't think I've ever heardthat in any Harvard business
case success story, so I'm goingto rule out that one.
This has got to be around likegeofencing or geotargeting or
some tech there, so I'm guessingit's more on the.
They probably went with theluxury automakers for maybe the

(37:23):
mapping side of it.
I'm guessing I don't reallyknow who this is, but that'd be
my best guess.

I thought this was hard.
I wouldn't have been able toguess this one that easily, so A
.
I think you're, I'm going toexclude A Willingness to pay is
going to be-.
We're going to double down onMongolia.
Sorry if anyone's from Mongoliahere, right?

now, but you just don't normally have that listed
in the top software market.

The future Genghis Khan is there, right.
So the future Genghis Khan isthere, right.
So there you go.
And then, so let's choosebetween B and C.
So focus on Germany's autoindustry, betting on luxury car
partnerships.
Pivot to emergency services inthe UK, positioning it as a
life-saving tool.

All right, I could see C too.
I mean, I was torn between Band C here.

And I'm not going to expect you to know the
company, because that was hard,I didn't even know it.
But but I will say the answeris the company's called
What3Words.
So What3Words is a proprietarygeocode system designed to
identify any location on thesurface of the earth with a
resolution of approximatelythree meters.
It is owned by What3WordsLimited, based in London,
england.
The system encodes geographiccoordinates into three

(38:23):
permanently fixed dictionarywords, and they chose… London,
I'm assuming, and they choseLondon.
I'm assuming, targetingemergency services.
A national TV campaignshowcasing how the system saved
lives led to adoption by police,ambulance services and outdoor
rescue teams Makes sense.
That's a pretty cool solution.
This pivot transformed theminto a critical infrastructure
tool, which you could argue.
I think it's a fair argument tosay go after automakers,

(38:45):
because that's a long-term wayof being successful or something
immediate which is emergencyservices, but now you're going
after government which is alsohard.

So this was a tough one.
We talked about tiny spec,which was Slack the game, before
it pivoted to a businessmessaging platform.
So sometimes pivots are theright way to go, yeah.

Well, this is all about pivots, so here we go.
Next one you're CEO of ahundred year old textile
manufacturer.
Sales are collapsing, factoriesare closing and bankruptcy
looms.
A disgruntled investor who owns49% of shares proposes a
radical plan Shut down textileoperations immediately.

(39:24):
Use remaining capital toacquire an insurance company.
So search your mind for somehistory.
This will, this will okay.
Okay A accept the plan, bettingon his investment acumen.
B rejected and seek agovernment bailout for textiles.
C counteroffer keep textilesrunning part-time while
diversifying.

(39:45):
D liquidate everything anddistribute cash to shareholders.

Man, our listeners, nailing all these.
I'm going to go this is aBerkshire Hathaway Warren
Buffett thing and I'm going togo A that he knows his stuff.
I could be wrong here.
I actually think a fascinatingparallel before you answer is
really the cash cow dilemma thatGoogle has right now.
Right, are you just going toshow the answers or are you
going to continue to show links?
Right, and they are caught inthat classic innovators dilemma

(40:11):
of what do they do, right?
But anyways, all right, we'llgo back here.

I think you're right on with today's challenge
and we should note that, becausethe choices they make today
will dramatically impact theirfuture.
You're right.
It's Berkshire Hathaway.
There's a famous investor.
His name is Warren Buffett,young guy at the time, chose A.
He terminated textiles,acquired national indemnity
insurance and transferredBerkshire into a holding company

(40:37):
for investments like Geico,dairy Queen, so many others.
The pivot created one of themost successful conglomerates in
history.

He's got a pretty good track record.

Yeah, he's pretty damn good, and he just recently
stepped down at what 92 or 4 orsomething I know, I know Just
incredible Still living in thesame house.
It's a crazy story, same housedrives the same car, but does
like to fly net jets because heowns it.
So, all right, I have aninteresting one for scenario
four.
Okay, yeah, you're leading astartup building encryption

(41:12):
software for handheld devices,so this is another pivot.
The dot-com boom is in fullswing, but your core product is
not gaining traction.
Few customers are buyingsecurity software for devices.
Meanwhile, you notice a surgein online auctions, especially
on a new site where buyers andsellers struggle to exchange
payments quickly and securely.
Your team proposes a radicalpivot Abandon handheld security
and instead build a digitalwallet to let people send money

(41:34):
by email.
This would mean a completeoverhaul of your business model
and a leap into the unknownworld of online payments.
Okay, what?

would you?

do A stick to your core.
Double down on handheld devicesecurity and wait for the mobile
market to mature.
B seek a merger with anotherstruggling fintech startup to
pool resources and survive.
C license your encryptiontechnology to bigger software
firms and exit the consumermarket.
Or D pivot to digital payments,launching an email-based money
transfer service for onlinebuyers and sellers.

Well, I'm going to guess this is a D, this is
PayPal.
I could be wrong here, butthat's the direction I'm going.
First of all, you're talkingabout eBay here, or maybe we're
going down the crypto path, butyeah, I could be wrong here, but
that's the direction I'm going.
First of all, you're talkingabout eBay here, or maybe we're
going down the crypto path, butyeah, I'm going to go PayPal on
this one.

Totally nailed it, bill.
So the company is PayPal,originally Confinity, founded by
Max Levchin, peter Thiel andLuke Nosen.

Yeah, there's a mafia.

There you go, and of course, we know Elon Musk
eventually made his way intothat with xcom.
So they yes, they chose X.
They pivoted digital payments,launched PayPal.
A lot of people send money viaemail.
There was a massive pain point,as you're talking about, for
eBay users, right?
Ebay eventually bought them.
Paypal became the defaultpayment platform for online
auctions, leading to its IPO in2002 and acquisition by eBay for

(42:44):
$1.1 billion that same year.

Cool history.

It's amazing.
Fun game, yeah, fun game.
So your point on Google?
So this is a point where theymake their money by providing
links to others.
They are providing to theconsternation of many firms that
are trying to get their SEOresults.
They have AI overviews at thetop.
They now push, they put theirads in between and they push
organic results way to thebottom.

(43:08):
That's their response to it.
Or they could just like ChatGPTand OpenAI, just provide a damn
good answer.

For me.
I think they're missing theboat on this one.
I know they're trying totransition softly, but I think
that's really hurting theirbrand, because the problem is
all the people that still go toGoogle and, by the way, I don't
think they've rolled that outuniversally.
I think they're doing it verygeographic and segment wise.
So a lot of people are stillgetting the same old frustrating
experience and they're tryingwhether it's, you know, claw,
chatgpt, perplexity and they'rehaving a much better experience

(43:37):
it's a 10x better experience andthey're losing, I think, a lot
of people.
I mean, I just think they knowthe direction it's going.
You just need to show theanswer.
You can still show thecitations and there is, like you
said, a whole AI optimizationthere.

What do you do with hundreds of billions of
dollars of revenue profit?

You know, you say , hey, we're focusing on the
long run, right, like that'swhat founders are supposed to do
is look beyond this three month, one year hurdle and look
towards the long run.
Look, I think ChatGPD has got apretty good valuation right,
and they're just showing theanswer.
Right, and they've evolvedtheir business model to include
subscriptions right, and they'veevolved their business model to
include subscriptions right,which is a natural evolution.
There they're selling toenterprises.

I even saw them the other day when I asked about
traveling somewhere.
There's like do you want us tobook it for you?
So just like.
Google allows you to getcommissions by sending you to a
booking service.
They're starting to do the samething.

I feel like Google has like it's in parallel
to our earlier conversations.
They've used SLG for so longand it's been really successful
and a new go-to-market model hascome out.
It's better, but they're kindof like just well, let's just
put two people on this and dipour toes in and I get it.
It is literally like theclassic innovator's dilemma.
This is like what HarvardBusiness Review everybody writes

(44:47):
about, right, and there's ahuge shareholder pressure not to
let profits go down or revenuego down in the short run.
But I just think anybodywatching this like there will
come a point very soon probablywhere you know Chet Chibiti is
going to eclipse enterprisevalue of Google.
Close behind them will beAnthropic and Perplexity.
And it's just like anyonewatching that follows the space

(45:09):
knows it.
What about Gemini?
I think Gem.
Like anyone watching that isfollows the space knows it.
What about gemini?
They have, I think, gemini.
So the gemini is great, butthey hide it like it's hard to
get to.
Like I want to just use it too.
Like I'm an early adopter, Ilove this stuff.
Like it's not.
I don't just go to googlecomand I have access to gemini.
Like I have to go to their labsproduct and turn things on.
It's not that simple right, makeit hard right, yeah, and so
like so my team uses acombination of these different

(45:29):
tools, depending on what makessense for what we're trying to
do.

If it's a coding tool, it was actually Cloud and
now it's Gemini, because Geminihas gotten better there.
Openai for many of the broadquestions.
I mean, we're just using alldifferent tools depending on
what's better, and I think thegame is about abstracting them
from the user.
Like don't give people a choice, you kind of give them what's
best.
But, like you're saying, thereprobably will be a convergence
where technical teams may not bedoing that anymore.

(45:54):
The better tools will figurethis out and they personalize,
they have memory, they havein-context memory they know what
you've done, so they keep youcoming back.

Yeah and I want that.
And the sad thing is likeGoogle has the distribution
right.
So many like anthropicopen-ended.
They don't have that right, butthey have the distribution.
But they're clinging on to theold model.
Like I think there's going tobe business case studies in the
future that are like oh, theyhung on to it way too long.

Well, for all those who invest in stock, I
think Google's around 16 to 18price to earnings ratio, which
is really low compared toMicrosoft.
Microsoft's much better.
So right now, people arebetting that they're going to
have a tough time.
So you can make a bet on Googleright now by a long-term call
option if you think that's theway, or don't go the other way.
So it's a very this is anamazing question to ponder and I
love your hot take on it, bill.

All right.

Here's some questions about you.
So did you always know youwanted to work in technology Was
?
There a specific moment orproject that sparked your
passion.
How'd you discover it?
What got you sparked?

I always loved tech.
I had a Commodore 64 growing upfor those old enough to kind of
remember that.
And I love technology, I lovesoftware.
I tried coding a game once.
I had like a big paper manualand literally started writing
the code Back then you had towrite it in assembly.
Yeah, assembly, and I hit runand it was like syntax error
line 13.
I fixed the syntax error, line47, syntax and I said you know

(47:18):
what, I'm not good at thisdeveloping stuff, but I still
love tech and I love softwareand I was so into it and you
know, I was at U of I when theweb browser started coming out
and Marc Andre I was at U of Iwhen the web browser started
coming out and Mark Andreessenalso was from there and so I was
just like I just want to be inthe business side somehow.
I don't know how or what, butyou know I did that and we did a
startup right out of college isin the gaming space.

(47:39):
We sold that and did a bunch ofothers on the consumer side.

But yeah, what got you into doing startups like
that early?
Usually, like you know thething that your parents would
say go make some money first,establish yourself first.

I don't know.
They were just very supportiveof me, like I always knew I
wanted to be in business.
I always wanted it Like I was anerd.

Were you reading Fortune Magazine at 12 or
something?

I was, yeah, I was reading Fortune, forbes,
wall Street Journal, businessWeek, I just geeked out on that.
I was such a nerd back then.
Oh, I still am a nerd now.
But whatever I like that, Ilike business and it's okay to
like it, bill I relate to you.

I don't usually share this very much, but now
it's everywhere.
My father used to bring homethe Wall Street Journal,
business Week, fortune Magazineand Time.
Magazine, and that would be myweekly and daily reading.
Yeah, yeah.

I think our parents were smart.

Those are my heroes, by the way, the business
folks who were engineering theturnaround.
Those are my heroes.
So what I love about thebusiness magazine is, unlike
news news is always the tiltnegatively, yeah Whereas
business magazine at least itused to be about these amazing
stories of turnaround and thesenew leaders that are confronting
the problem.
And then, in the middle of thegreat turnaround, Absolutely.

Yeah, there's so many amazing stories.
I still like one of my favoritethings now is like I'll get an
economist on a long flight andjust read it.
You know cover to end and yeah,there's still so much greater
for me, I think, just like youknow, just being curious and
always learning, I think likeit's awesome, like I said, gold
markets is always changing.
There's always going to besomething new Like you can't
just rest on.
You know what worked last year,a decade or three decades ago.

You've gone from being a kick-ass CMO to a
content creator, so was there aspecific pain point that got you
to that point to move from oneto the other and start SaaS CMO
Pro?
Was there a trigger that madeyou decide you needed to be when
delivering this as publiceducation beyond private
advisory?
There's a lot of folksthroughout the Valley that do

(49:34):
this, that they hit it, theyprovide advisory, they get on
boards and they're known rightor, like you, they may become
venture partner or ventureadvisors, but you decided to
turn this into a business whereyou go public and I've seen your
episode where you invested aton into building your own
studio and talk about what painpoint.

Yeah.
So, first off, don't build yourown studio.
It took me forever to do and,although I can go, fancy camera
angles and, you know, do allthis.

I saw this great movable stuff that's that's
awesome.

It was such a time.
It took me like a year and, forthose that do want to have a
video on it, if you want to geta good camera, it's a great
video.

I saw it.
It was awesome.

But I think for me there were two things, like
one, philosophically, I justknew when I was an operator,
like I just wanted to learn, Iwant other good sources and I
kind of wanted to give backright and just help people out.
And so all my videos, all mycontent is totally free, whether
it's shorts or long form stuff.
I just wanted to help peopleout.
That would be my aspirationalgood story.
The the lazy bad story was Ikept getting asked the same

(50:34):
questions by founders and CEOs,like how does freemium work, or
what does PLG, and I'm just likeI will make this video once and
not lose, just like send him alink afterwards.
Yeah, send the link this is howto do it.
Just watch this video, right,like I just sent someone that
was wanted to work with me.
I sent like 12 videos.
I'm like here's like literallylike a ton of info and if you
still want to work there, great.
So yeah, I was like justanswering questions that have

(50:54):
been answered again, but I justthink it's super fun.
I just like I love go to market.
I really do right, like I don'tneed to do this.
I just because I love doing itand I love working with other
founders and even, like it wasinteresting in the past, when I
do my advisory stuff, I'dusually do like series b and
above, and now I've starteddoing like a and even seed round
, because there are so many coolpure play ai companies that are

(51:14):
coming out that are gettingthat good product market fit but
want help with theirgo-to-market or want to help
grow faster, want help withtheir marketing and, and for me
that's super exciting.
If you're a student of businesswhich I know you are as well
this is an amazing time rightnow.
Everything is changing and justto be a part of that is super
gratifying and rewarding.
For me that's fantastic.

I can totally see that in you.
So how do you apply rigorous,data-driven go-to-market
principles that you use formulti-billion dollar companies
to your own content creationstrategy for SaaS, cmo Pro and
your YouTube channel?
So are you tracking creatormetrics, content, qualified
leads for audience retention onvideos, personal brand

(51:57):
attributions Are you optimizingyour own content funnel in a
similar way that you did foryour product launch?
A lot of times when you createyour own content, you kind of
want to do it and move away fromit, or do you actually want?
It took me a long time to wantto look at and watch myself
again.

Totally Well.
I so my dad was an engineer andI always kind of came up, was
brought up in more of like a youknow measure stuff.
I can hear him now like measurethree times, bill cut once
right, that's how you don't makea mistake.
And so I always kind of hadthis measure thing.
And when I got into business, Ialways hated the ivory tower
thing where and I saw us a lotof companies and even ones I

(52:33):
worked at, where it'd be a bunchof execs sitting in a you know
nice high floor in their ivorytower and they were debating
like what should go on thehomepage and we should use this
messaging or this image or thisone.
And I'm like why are wedeciding?
Why don't we just test this andlet the users answer?

Do two or three versions and test it.

Totally right and so, like I've always just tried
to be open minded, like, hey,put stuff out, test it.
So yeah, there's all thiscreator type stuff right With.
You're looking at engagementand across all the different
channels.
So that's been reallychallenging for me is when I
went out, I tried to be channelagnostic.
So I'm doing stuff on TikTokand I'm doing stuff on LinkedIn

(53:10):
and doing stuff on YouTube andall these different ones and
it's a learning experience,right.
You learn and you're like thatworked boy, that bomb, that
totally didn't work there.
Like I got to make my introshorter and not just, you know,
wax on and I saw.

I saw one thing in just just the evolution on your
YouTube shorts.
You went from having the musicin the background to not yeah,
and frankly, it played so muchbetter when you took it out,
because you're a compellingspeaker in and of yourself and
you do add in these little videothing video shorts as part of
it.

And it was tough for me, cause, like I filmed a
bunch of my content at thebeginning and then I did a mass,
like I worked with editors andAI tools and and I have a.
So I have a big chunk ofcontent that, like I've already
finished and I'm still releasingand I have another bunch that's
like revised Right, and one ofthe things I found in business
is people don't they don't wantit over-edited Right.
It actually like over-edited, Ithink smells like it's

(53:57):
corporate Right and so sometimesjust like a simple, authentic
or even just holding like aniPhone walking around, hey guys,
like here's how POG works LikeI think can perform better.
So it's all.
These are learning experiences,you know, and I think it's just
come with open mind and youknow you can still improve.
And I asked my daughter whatworks too.
That helps.
How old is your daughter?
She's 15 now, and so she'salways like dad you're, oh my

(54:17):
God, like that was cringy.
What are you doing?

You have the perfect audience for it.
That's great.
All right, here we go.
I have a bunch of quickquestion answers.
More about you.
So what's something you thoughtthat you'd figure out by now,
but are still completelyconfused by Women?

That's something my dad would say I love you,
honey, amy, you're the best.

But it keeps you.
It keeps you together.
It does Otherwise you would getbored.

I'm still keeping up my toes, still trying to
figure out.
Does she want my advice rightnow, or does she just want me to
listen to what happened?
Right, I think I'm learningthat, like usually, I give the
advice.
I'm like no shut up, bill, justlisten and you'll be better
Listen till they ask All right,great answer.

What's a question you wish people would ask more
often and what's a question youwish they'd stop asking?

I wish more founders would kind of like hey,
how can we update ourgo-to-market right?
How can we update our pricing?
How can we just improve it?
I just feel like for a lot offounders and I get it like most
founders in the Bay Area aretechnical founders, right, so
go-to-market is kind of new andI just I love working with

(55:26):
founders that are like, hey, wewant a more modern, clean,
go-to-market engine.
So, yeah, that's definitelysomething that's awesome.

What do you wish they would stop asking about?
That's a tough one, because youseem like a pretty open and
easy approachable person.

Yeah, I'm trying to think just something like
more around, like an old salesmodel, like this sales model
should work.
Like why does no one know aboutus?
Or I don't know?
Like usually I'm pretty openminded with all the questions
there's no bad questions, right.
And I get it Like if I was atechnical founder.
This is all new.
If I'm, if I'm the CEO, if I'mrunning technical stuff, I'm
going to ask a lot of like weirdor dumb questions might be
wrong or, in your case, youmight just openly think they're

(55:58):
wrong.
Well, we talked about thefreemium right.
I think people have a reallyharsh reaction to it and as a
marketer and a growth person,I've seen the incredible power
that it has, so I'd probably gowith that one.

(56:19):
That's a great one.

If you could have a 30-minute conversation with
any version of yourself in thepast, what age would you pick
and what would you want todiscuss?

Oh man, I would want to go back to, I think, my
10 year old self.
I remember riding my dirt bikeand I remember stopping in the
middle of the street andthinking like, wow, I wonder,
like what my life will be likeat like 50 or 51, like what I am
now.
And I would be fun to go backand talk to that person and just
be like, hey, you know, andhere's how it turned out, or
this worked or this absolutelydid not work.
It would just be a fun.

I don't know what's one piece of advice you'd
give yourself.
You're 10 years old, you're 50year old self.
You're a 10 year old that'sactually willing to listen,
which is actually 10 is a goodage for listening.
It's not because 14 is not agood age for listening.

Well, I watched a lot of like time movies and
back in history and stuff.
So I would say like, of courseI'd say, don't change a thing,
Otherwise I won't be here and Iwould have met my wife and my
amazing daughter.

Yeah, there's that movie.

Yeah, the butterfly effect right you know,
like make sure you get on thistrain or move to Denver at this
time, or do whatever.

Give them the comic book, like Back to the
Future.

No, if I had to give myself just always be
learning, right, like, just stayhumble, know what you know,
know what you don't know, andjust like hey, just always try
to be learning.

Do you have a favorite life motto?

Carpe diem.
You know, I, I, I end a lot ofmy videos that with that one and
I'm just a big believer in likethere's opportunities
everywhere and you know, likesometimes just just take it,
seize the day, right.
You know, just go out there.
Life is short, life is precious.
You know, my dad's beenbattling through cancer.
That's been really rough andit's like one of those things
like you just have to.
Every moment is precious right.

(57:49):
You just have to like seize theday, like don't don't waste any
days, just just go out there.

I love it.
What's something thatconsistently surprises you about
other people, either in a goodway or a bad way?

bad way.
I'm always surprised by thehumanity, the goodness of people
, like, maybe not surprised, butI think some people are like,
oh, there's just some people arejust bad or this or that.
And I always think, like youknow, there's just so many good,
humble, great people out therelike trying to do the right
thing.
And I even think with businessthat happens a lot too, right?
Like if we make that parallelwhere you know, if you give a
bad metric to someone andthey're just going to try to hit

(58:22):
it right, if you give marketersleads, they're just going to
stuff with as many leads as theycan.
But it was a bad metric, butthere's just good people, right?
So I think most people aretrying to do the right thing and
you know, as leaders and asbusiness people, if we can
support them and give them theright metrics, we can take them
down the right path.

You know, I think there's too much of this, like
you're saying us versus them andit's created a highly polarized
environment and instead of the,they're evil, they're awful,
they're stupid.

Maybe there's a.

Hey, let's understand why you have that
point of view Right and frankly,I see this a lot with college
kids and I thought college wassupposed to be a place where you
learn things and learn how tothink, and so there's some work
to be done, and I I'd love tosee, like you're talking about,
open yourself up to other folks.

Yeah, beginner's mindset Think they're good.

If you start off thinking they're pretty good,
you're probably less likely tolabel them.

Yeah, totally.

All right.
If you had to teach amasterclass on something that's
not your job, something you'regenuinely passionate about, what
would the course be called?

Soil structure and gardening.
I really nerd out on that.
I nerd out on a lot of things.
I just get into stuff.
But I love gardening If there'sany gardeners out there whether
you're talking about likeornamentals, edibles, just
across the board I love growingthings and I think it's like
super fun.
Yeah, I've got a bunch of fruittrees I'm growing right now and
I've dived way into avocadosand nightly temperatures and AB
pollination and, yeah, I lovegardening.
If anyone's geek out on that,hit me up on LinkedIn.

(59:49):
That's fantastic.

So thank you for that.
This was super helpful.
This was one of the bestsessions I've ever had.
Bill, you're a true pro and Ilove marketers who are super
innovative like you that are nowout there teaching and you've
opened yourself up so much to it, so I'd urge everyone to take a
look at Bill's YouTube channel,SAS CMO Pro.
Recently, Bill also, along withour friend John Miller and a

(01:00:12):
couple other folks, put out SASbenchmarks right.

Bill Macaitis (01:00:14):
SAS go to market.
Sas B2B marketing benchmarksB2B marketing benchmarks and I
think they can get to them ifthey, on LinkedIn, just ask you
Just ask me Hit me up onLinkedIn, say, hey, I want the
B2B benchmark report, orliterally, if anyone just wants
to chat, you know, like exchangeideas, linkedin is probably the
best place to reach me.
Or you can always go to my site, cmoprocom.

Rajiv Parikh (01:00:33):
Chock full of fantastic information.
He's very open and free withBill's offering, so loved having
you on the show, bill.

Bill Macaitis (01:00:45):
And look forward to hanging out with you over in
Marin.
Absolutely.

Rajiv Parikh (01:00:48):
Hey, it was such a pleasure talking with you.
I really enjoyed theconversation.
Thanks again for having me.
If you're a marketing orbusiness innovation geek, this
is the perfect episode.
Bill has really thought throughhis methodology, his way of
thinking, his belief system.
Coming from the gaming world andapplying those learnings, his
notion of product-led growth,freemium, and how that applies

(01:01:09):
to today's or even he talkedabout today product-led sales,
which I think is a reallyinteresting subject for people
to get into, and what I likeabout it is, with the channel
that he's created, you canaccess all that.
So our objective was to getthat extra out of him that you
couldn't get from all thoseplaces, and we got that today
and I really appreciate it.
Love his point of view aboutcarpe diem seize the day, grab

(01:01:31):
opportunities where they can be.
There's so many opportunitiesthat are out there.
He expressed real concernsabout what could happen in the
AI world and some of it is aleap of faith and it's hard when
you have that leap leap offaith and we're all dealing with
it.
I love his hot take on Googleand what they're missing the
boat on, and it's instructive.
This is one of those thingswhere you have to look and say

(01:01:52):
this is a time to mark and sayit's a great debate.
So thank you for joining ustoday.
It was such a thrill to havethis conversation.
I hope you enjoyed it as muchas me.
Thanks for listening.
If you enjoyed this pod, pleasetake a moment to rate it and
comment.
You can find us on Apple,spotify, youtube, our own

(01:02:14):
website and everywhere podcastscan be found.
The show is produced by AnandShah and edited by Sean Marr and
Laura Ballant.
I'm your host, rajiv Parikh,from Position Squared, an
AI-driven hopefully PLG-drivengrowth marketing company based
in Silicon Valley.
Come visit us at position2.com.
This is an effing funnyproduction and we'll catch you
next time.
Remember folks, be ever curious.

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The Freemium Formula: Converting Fear Into 10X Growth/Bill Macaitis - Slack, PLG, Pivots ~ Spark of Ages Ep 42

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.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}The Freemium Formula: Converting Fear Into 10X Growth/Bill Macaitis - Slack, PLG, Pivots ~ Spark of Ages Ep 42