January 20, 2025 • 12 mins
Ever wondered if dedicating most of your working hours to a single client is a smart business move? Join host Treasa Edmond and guest co-host Sarah Greesonbach, founder of B2B Content Studio, as they unravel the complexities of managing long-term client relationships, especially within the unpredictable realm of startups. Sarah shares her wealth of experience in high-impact marketing content, and together they highlight the potential risks and the importance of contract flexibility. The discussion is packed with personal stories and essential advice on maintaining a consistent marketing strategy to ensure you're never left scrambling for new clients when circumstances change.
About Our Guest
Sarah Greesonbach is the founder of B2B Content Studio and a seasoned expert in B2B marketing content. With over a decade of experience writing for Fortune 100 brands and top executives, Sarah specializes in transforming complex ideas into clear, compelling content. She has worked with industries ranging from SaaS and HR tech to retail and higher education, helping businesses showcase their unique value to prospective customers.
Links You Might Want
Check out B2B Writing Institute and sign up for Sarah's newsletter
Connect with Sarah on
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Treasa Edmond (00:00):
Welcome back to Boss Responses.
I've loved talking to every oneof my guest co-hosts for Boss
Responses, but recording theepisodes for this week was a
truly special experience.
If you've ever had theopportunity to talk with Sarah
Greesonbach, you'll understandthat her special blend of humor,
knowledge and off-the-wall funmakes every conversation one to
(00:20):
remember.
I hope you get to experience alittle bit of that this week,
because I had a blast recordingthese.
Sarah is the founder of B2BContent Studio and an expert in
crafting high impact marketingcontent for top tier brands.
She started her career as aghostwriter for Fortune 100
companies and has spent the lastdecade helping B2B companies
(00:42):
uncover their unique value andturn it into content that
connects, which is a phrase Iuse as well, so I love that
commonality that we have.
For today's episode.
We're going to discuss therisks of taking on a long-term
client that has the potential tocompletely dominate your
schedule, and we both share afew stories and lessons that
we've learned along the way.
(01:02):
Let's get into it.
If you're a freelancer,business owner or anyone who
deals with clients, you're inthe right place.
I'm your host, Treasa Edmond.
I've been dealing with clientsand running my business for
nearly two decades and in thattime I've dealt with my share of
doubt, imposter syndrome andnot knowing what to say when a
(01:23):
client asks a question.
I wasn't ready for.
I created this podcast toempower you with the boss
responses you need to grow yourbusiness.
Each week, my guest co-host andI will bring you five episodes
packed with practical insights.
Monday through Thursday, weanswer your questions, and
Fridays we dive deep to explorehow our co-hosts embrace their
(01:46):
role as the boss of theirbusiness.
Welcome to Boss Responses,sarah.
Thank you for being here withus this week.
I really appreciate it.
Thank you for having me Allright.
So today you're answering ourfirst question, and it is from
Claire.
All right.
So today you're answering ourfirst question, and it is from
Claire.
Claire says I've freelanced asa web developer for three years,
(02:08):
mainly working on short termprojects.
Recently, a tech startupreached out about a year long
contract to overhaul theirentire website infrastructure Go
Claire.
The fee is excellent and wouldprovide pretty stable income.
The problem is it would requireabout 80% of my client hours.
I've heard horror stories offreelancers losing their main
(02:29):
client and then struggling torebuild their business.
How can I evaluate whether thisclient is worth the risk?
What do you think, sarah?
Sarah Greenback (02:37):
I promise we will actually answer the
question, but first I just haveto tell Claire to not worry
about it, because startups don'treally finish the things that
they have to do, especially ifit takes a year.
(02:58):
Yeah, Not only because thatstartup is going to change its
positioning at least three timesover the course of the year,
but at least half the marketingteam is going to leave and be
replaced at that time as well.
Treasa Edmond (03:10):
So just as a first take, yeah, I made a note
the hazards of startups, sowe're on the same page there.
Sarah Greenback (03:17):
Yeah, and so I'd say, though, if we're, you
know, let's assume everything isjust fantastic and you really
want to go for this, I think,when it comes to evaluating the
risk, it is half communicatingwith that client and creating
either a contract or a timelinethat gives you lots of outs.
So, setting it up quarterly,setting it up like a one month
(03:38):
plan, two month plan, that kindof thing, so you can really
easily exit if they need to oryou need to.
And then the horror story isthat the freelancer it's not
that they lost their main client, it's that they stopped
prospecting and then, when theirmain client stopped, they
didn't have anything.
So what is on your to-do listis to keep prospecting
(03:58):
throughout that relationship andmake sure that you can move
right into some other projectsonce it's over.
Treasa Edmond (04:04):
Yeah, yeah, that's a big thing.
And do you know what I've beenburned in this situation?
The bad kind of burns, thehorror story that Claire has
heard?
Is there a good burn?
Yes, there is.
We'll have to talk about thatlater.
Yeah, I'll come back to thatclient who was about 80% of my
(04:27):
client hours and I had to letthem go because they were
incredibly toxic and it was oneof those things that I put off
and I put off and I put off andthen I couldn't put it off
anymore, so I had to let them goand all of a sudden nothing.
So I had to scramble to fill inthose hours and luckily I have
(04:50):
a really good referral networkto where.
That was fairly easy to do andI never stopped marketing.
That's my rule ever, ever, ever, always.
Market, always, keep thatclient funnel coming in and then
do what you need to do.
If you have to scramble, you'reready, you're ready, that's all
it is.
Sarah Greenback (05:09):
Yeah, and I think this hints a bit at what
we'll talk about in a couple ofdays.
But one thing people don'trealize is that to continue
marketing, sometimes that takessome emotional boundaries to not
get your hopes up.
People think that you onlymarket when you are available
and ready to take on a job.
But what?
You're actually doing ismarketing, so that people are
(05:31):
aware of what you do and who youare.
Yes, because it's going to takesix to 12 months for them to be
ready for a project.
Treasa Edmond (05:38):
And there's a difference between marketing and
prospecting.
Oh yes, it's huge Prospecting isactively seeking active clients
.
Right now, marketing is keepingthat funnel open so that you
have potential clients in thewings and you're building out
your calendar when it comes tolong contracts.
And let's go back to thestartup issue I usually prefer
(06:03):
not to work with startupsbecause they are Is crap shoot
the right word, sarah?
Yeah, they can be problematicand it's not their fault.
It's the nature of the beast.
They are in flux, they arefiguring out what works and part
of that process is doingdifferent things every three
months, apparently.
Sarah Greenback (06:25):
Truly.
This is my understanding, forsome people that really is
thrilling and exciting and thenthey learn to charge enough for
it that it was worth it and itworks out.
I have perhaps two friends thatdo thought leadership for
startups and they're just builtdifferent, Like they really
enjoy that kind of changingdirections or they have enough
(06:46):
boundaries in place that whensomeone changes directions it
doesn't affect them and haveeverything come crashing down.
But I do think you want tochoose startups, you don't just
want to jump on that if that'sthe first opportunity that pops
up.
Treasa Edmond (06:58):
Exactly, and I will do writing and ghost
writing and thought leadershipand all of those things for
startups, because it can be kindof hit or miss, it's fine.
I don't have to have a regularrelationship with them to do
that.
I will not, however, do contentstrategy for a startup, because
that's a huge commitment of mytime and effort, and I only do a
content strategy for a clientif I can help them succeed, and
(07:20):
I can't guarantee that with astartup, because they will
change their entire direction inthe next year at some point.
But because of my burn, becauseof the client that I had to let
go, who was 80%, and I was, youknow, in a situation where I
did have to fill my time then mynew rule of thumb is no one
client can take more than 50% ofmy client hours, and I was
(07:44):
talking to someone a few weeksago that their rule of thumb is
30%, I think.
So no more than 50% of myclient hours for one client.
So if we could scale that down,that might be a possibility.
Web developer is much differentfrom writing, though, and that
is everything has to build oneverything, and it matters if
(08:05):
they make a change.
So when it comes to evaluatingwhether they're worth the risk
I'd really look at.
Can you handle this mentally,more than work related?
Because there are going to bechanges.
It's going to require that yourestart everything you do at
some point.
Are you willing to work withthat and are you willing to just
live in the flux that isstartup world?
(08:27):
I think those are even moreimportant than is this client
worth the risk of the 80%?
Sarah Greenback (08:34):
Well, and I feel pretty darn dumb because I
missed the web developer part,because I was so focused on the
year long part, and I would saythat even adds even more of a
red flag, because for a startupto look for web development
(08:54):
support for a year, what theyneed to be doing is either
hiring a web developer, so youmight be at risk of actually
being hired on in what theythink is a full-time capacity,
and that could be problematicfor you but also illegal for
them, depending on where theyare and then also they should be
looking at hiring like anagency that can take on this
project at a really mature leveland a really high fee.
So I think, to look at it theway they should, you should be
(09:17):
setting the timeline, not them,right?
That's kind of a whole red flagalready.
Treasa Edmond (09:23):
And I actually do have issues with that.
If I'm working with a clientlong-term, I set the scope of
the project, but it's with theirinput.
It's always with their input.
But you should be deciding howyou're doing the project and how
you're running your business.
Your client shouldn't reallyhave a set on that.
And the fee thing so anexcellent fee does not always
(09:45):
counteract the inconvenience ofworking in certain situations.
So that's just something tothink about.
Sarah Greenback (09:53):
I was also really curious what an excellent
fee is, because to me thatmight be a very different number
.
Treasa Edmond (09:59):
Yeah, and we're both writers, and even between
the two of us it might be a verydifferent number.
Sarah Greenback (10:03):
Yeah.
Treasa Edmond (10:04):
That depends on what you set.
But I personally, Claire, wouldsay be very cautious in this
situation, just across the board.
You have to evaluate it.
You do.
Is it worth the risk to you?
But I would definitely 100%recommend scaling it back so
that they didn't take up 80% ofyour client hours.
That's just me.
Sarah Greenback (10:26):
Yeah, and so I'm going to agree with
everything we've set up to nowand then also completely reverse
my position for the last minute, just in case Claire is like
you know what.
I've actually decided to takethis.
I'm just trying to figure outhow to make it work, and I'll
just disclose I've absolutelyleaned on an agency for more
than 50% of my work at differentperiods of time and it really
(10:48):
worked well for me.
It allowed me to take all of myprospecting time and marketing
time and channel it to somethingelse that I was trying to
switch to and shift to.
So, I think it can be donestrategically and it's not
necessarily the fact that you'regoing to tank your business
suddenly because you've madethis bad choice.
It's just making sure thatyou're protecting yourself.
To check in every three monthsAm I still prospecting?
(11:10):
Could I dig up some work rightnow if I needed to?
Am I doing these regularmarketing activities and then
taking a little time for myself?
Am I leaning into the benefitsof that stability Because you're
going to lean into that benefitand it's going to lean you away
from this other?
What's that called Like?
Treasa Edmond (11:30):
protecting and hedging your bets, leaning to a
different side of the spectrum.
Yeah, so you can do it.
You absolutely could do it.
You just want to make sure thatyou do it right and you go into
it with your eyes open,understanding where you're going
with it.
So control the process.
Do not let the process controlyou, and make sure you
understand all of the risks thatare inherent with a decision
like this.
Sometimes the risks are totallyworth it, absolutely.
(11:50):
All right, that is day one withSarah.
Come back tomorrow and we'regoing to talk about what happens
whenever you are working on aproject and it's much more
complex than you thought itwould be.
Welcome back to Boss Responses.
I've loved talking to every oneof my guest co-hosts for Boss
Responses, but recording theepisodes for this week was a
truly special experience.
If you've ever had theopportunity to talk with Sarah
Greesonbach, you'll understandthat her special blend of humor,
knowledge and off-the-wall funmakes every conversation one to
(00:20):
remember.
I hope you get to experience alittle bit of that this week,
because I had a blast recordingthese.
Sarah is the founder of B2BContent Studio and an expert in
crafting high impact marketingcontent for top tier brands.
She started her career as aghostwriter for Fortune 100
companies and has spent the lastdecade helping B2B companies
(00:42):
uncover their unique value andturn it into content that
connects, which is a phrase Iuse as well, so I love that
commonality that we have.
For today's episode.
We're going to discuss therisks of taking on a long-term
client that has the potential tocompletely dominate your
schedule, and we both share afew stories and lessons that
we've learned along the way.
(01:02):
Let's get into it.
If you're a freelancer,business owner or anyone who
deals with clients, you're inthe right place.
I'm your host, Treasa Edmond.
I've been dealing with clientsand running my business for
nearly two decades and in thattime I've dealt with my share of
doubt, imposter syndrome andnot knowing what to say when a
(01:23):
client asks a question.
I wasn't ready for.
I created this podcast toempower you with the boss
responses you need to grow yourbusiness.
Each week, my guest co-host andI will bring you five episodes
packed with practical insights.
Monday through Thursday, weanswer your questions, and
Fridays we dive deep to explorehow our co-hosts embrace their
(01:46):
role as the boss of theirbusiness.
Welcome to Boss Responses,sarah.
Thank you for being here withus this week.
I really appreciate it.
Thank you for having me Allright.
So today you're answering ourfirst question, and it is from
Claire.
All right.
So today you're answering ourfirst question, and it is from
Claire.
Claire says I've freelanced asa web developer for three years,
(02:08):
mainly working on short termprojects.
Recently, a tech startupreached out about a year long
contract to overhaul theirentire website infrastructure Go
Claire.
The fee is excellent and wouldprovide pretty stable income.
The problem is it would requireabout 80% of my client hours.
I've heard horror stories offreelancers losing their main
(02:29):
client and then struggling torebuild their business.
How can I evaluate whether thisclient is worth the risk?
What do you think, sarah?
Sarah Greenback (02:37):
I promise we will actually answer the
question, but first I just haveto tell Claire to not worry
about it, because startups don'treally finish the things that
they have to do, especially ifit takes a year.
(02:58):
Yeah, Not only because thatstartup is going to change its
positioning at least three timesover the course of the year,
but at least half the marketingteam is going to leave and be
replaced at that time as well.
Treasa Edmond (03:10):
So just as a first take, yeah, I made a note
the hazards of startups, sowe're on the same page there.
Sarah Greenback (03:17):
Yeah, and so I'd say, though, if we're, you
know, let's assume everything isjust fantastic and you really
want to go for this, I think,when it comes to evaluating the
risk, it is half communicatingwith that client and creating
either a contract or a timelinethat gives you lots of outs.
So, setting it up quarterly,setting it up like a one month
(03:38):
plan, two month plan, that kindof thing, so you can really
easily exit if they need to oryou need to.
And then the horror story isthat the freelancer it's not
that they lost their main client, it's that they stopped
prospecting and then, when theirmain client stopped, they
didn't have anything.
So what is on your to-do listis to keep prospecting
(03:58):
throughout that relationship andmake sure that you can move
right into some other projectsonce it's over.
Treasa Edmond (04:04):
Yeah, yeah, that's a big thing.
And do you know what I've beenburned in this situation?
The bad kind of burns, thehorror story that Claire has
heard?
Is there a good burn?
Yes, there is.
We'll have to talk about thatlater.
Yeah, I'll come back to thatclient who was about 80% of my
(04:27):
client hours and I had to letthem go because they were
incredibly toxic and it was oneof those things that I put off
and I put off and I put off andthen I couldn't put it off
anymore, so I had to let them goand all of a sudden nothing.
So I had to scramble to fill inthose hours and luckily I have
(04:50):
a really good referral networkto where.
That was fairly easy to do andI never stopped marketing.
That's my rule ever, ever, ever, always.
Market, always, keep thatclient funnel coming in and then
do what you need to do.
If you have to scramble, you'reready, you're ready, that's all
it is.
Sarah Greenback (05:09):
Yeah, and I think this hints a bit at what
we'll talk about in a couple ofdays.
But one thing people don'trealize is that to continue
marketing, sometimes that takessome emotional boundaries to not
get your hopes up.
People think that you onlymarket when you are available
and ready to take on a job.
But what?
You're actually doing ismarketing, so that people are
(05:31):
aware of what you do and who youare.
Yes, because it's going to takesix to 12 months for them to be
ready for a project.
Treasa Edmond (05:38):
And there's a difference between marketing and
prospecting.
Oh yes, it's huge Prospecting isactively seeking active clients
.
Right now, marketing is keepingthat funnel open so that you
have potential clients in thewings and you're building out
your calendar when it comes tolong contracts.
And let's go back to thestartup issue I usually prefer
(06:03):
not to work with startupsbecause they are Is crap shoot
the right word, sarah?
Yeah, they can be problematicand it's not their fault.
It's the nature of the beast.
They are in flux, they arefiguring out what works and part
of that process is doingdifferent things every three
months, apparently.
Sarah Greenback (06:25):
Truly.
This is my understanding, forsome people that really is
thrilling and exciting and thenthey learn to charge enough for
it that it was worth it and itworks out.
I have perhaps two friends thatdo thought leadership for
startups and they're just builtdifferent, Like they really
enjoy that kind of changingdirections or they have enough
(06:46):
boundaries in place that whensomeone changes directions it
doesn't affect them and haveeverything come crashing down.
But I do think you want tochoose startups, you don't just
want to jump on that if that'sthe first opportunity that pops
up.
Treasa Edmond (06:58):
Exactly, and I will do writing and ghost
writing and thought leadershipand all of those things for
startups, because it can be kindof hit or miss, it's fine.
I don't have to have a regularrelationship with them to do
that.
I will not, however, do contentstrategy for a startup, because
that's a huge commitment of mytime and effort, and I only do a
content strategy for a clientif I can help them succeed, and
(07:20):
I can't guarantee that with astartup, because they will
change their entire direction inthe next year at some point.
But because of my burn, becauseof the client that I had to let
go, who was 80%, and I was, youknow, in a situation where I
did have to fill my time then mynew rule of thumb is no one
client can take more than 50% ofmy client hours, and I was
(07:44):
talking to someone a few weeksago that their rule of thumb is
30%, I think.
So no more than 50% of myclient hours for one client.
So if we could scale that down,that might be a possibility.
Web developer is much differentfrom writing, though, and that
is everything has to build oneverything, and it matters if
(08:05):
they make a change.
So when it comes to evaluatingwhether they're worth the risk
I'd really look at.
Can you handle this mentally,more than work related?
Because there are going to bechanges.
It's going to require that yourestart everything you do at
some point.
Are you willing to work withthat and are you willing to just
live in the flux that isstartup world?
(08:27):
I think those are even moreimportant than is this client
worth the risk of the 80%?
Sarah Greenback (08:34):
Well, and I feel pretty darn dumb because I
missed the web developer part,because I was so focused on the
year long part, and I would saythat even adds even more of a
red flag, because for a startupto look for web development
(08:54):
support for a year, what theyneed to be doing is either
hiring a web developer, so youmight be at risk of actually
being hired on in what theythink is a full-time capacity,
and that could be problematicfor you but also illegal for
them, depending on where theyare and then also they should be
looking at hiring like anagency that can take on this
project at a really mature leveland a really high fee.
So I think, to look at it theway they should, you should be
(09:17):
setting the timeline, not them,right?
That's kind of a whole red flagalready.
Treasa Edmond (09:23):
And I actually do have issues with that.
If I'm working with a clientlong-term, I set the scope of
the project, but it's with theirinput.
It's always with their input.
But you should be deciding howyou're doing the project and how
you're running your business.
Your client shouldn't reallyhave a set on that.
And the fee thing so anexcellent fee does not always
(09:45):
counteract the inconvenience ofworking in certain situations.
So that's just something tothink about.
Sarah Greenback (09:53):
I was also really curious what an excellent
fee is, because to me thatmight be a very different number
.
Treasa Edmond (09:59):
Yeah, and we're both writers, and even between
the two of us it might be a verydifferent number.
Sarah Greenback (10:03):
Yeah.
Treasa Edmond (10:04):
That depends on what you set.
But I personally, Claire, wouldsay be very cautious in this
situation, just across the board.
You have to evaluate it.
You do.
Is it worth the risk to you?
But I would definitely 100%recommend scaling it back so
that they didn't take up 80% ofyour client hours.
That's just me.
Sarah Greenback (10:26):
Yeah, and so I'm going to agree with
everything we've set up to nowand then also completely reverse
my position for the last minute, just in case Claire is like
you know what.
I've actually decided to takethis.
I'm just trying to figure outhow to make it work, and I'll
just disclose I've absolutelyleaned on an agency for more
than 50% of my work at differentperiods of time and it really
(10:48):
worked well for me.
It allowed me to take all of myprospecting time and marketing
time and channel it to somethingelse that I was trying to
switch to and shift to.
So, I think it can be donestrategically and it's not
necessarily the fact that you'regoing to tank your business
suddenly because you've madethis bad choice.
It's just making sure thatyou're protecting yourself.
To check in every three monthsAm I still prospecting?
(11:10):
Could I dig up some work rightnow if I needed to?
Am I doing these regularmarketing activities and then
taking a little time for myself?
Am I leaning into the benefitsof that stability Because you're
going to lean into that benefitand it's going to lean you away
from this other?
What's that called Like?
Treasa Edmond (11:30):
protecting and hedging your bets, leaning to a
different side of the spectrum.
Yeah, so you can do it.
You absolutely could do it.
You just want to make sure thatyou do it right and you go into
it with your eyes open,understanding where you're going
with it.
So control the process.
Do not let the process controlyou, and make sure you
understand all of the risks thatare inherent with a decision
like this.
Sometimes the risks are totallyworth it, absolutely.
(11:50):
All right, that is day one withSarah.
Come back tomorrow and we'regoing to talk about what happens
whenever you are working on aproject and it's much more
complex than you thought itwould be.
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