All Episodes

June 2, 2021 30 mins

Send us a text

Matt Olpinski is a successful UI + UX designer and developer who teaches thousands of freelancers how to get more clients, raise their rates, and create a better life for themselves. 

In this episode, Matt discusses in depth how to operate as a freelancer. Matt shares how he accidentally fell into the world of freelancing and how you can find clients through your personal network by letting people know what it is that you do. Matt also reveals how he transitioned from being a full-time freelancer to running his agency and how he built his own lively community – The Freelance Institute. Key points covered throughout the episode include:

  • Matt’s leap into full-time freelancing.
  • Communicating with clients and delivering value. 
  • Learning from conversations and evolving through feedback.
  • Useful resources for operating your business. 
  • Freelance transformation - the shift from freelancing to running an agency. 
  • How to position yourself and scale your business. 
  • Finding the right people to work alongside.  
  • How to develop and grow a thriving community.
  • Advice on finding your first 10 customers.
  • Unlocking the power within your personal network.

Matt holds over ten years of industry experience and has worked with renowned world-class brands such as Facebook, Coca-Cola, PayPal, Porsche, and Google, to name but a few. 

Matt’s Freelance Institute is a community for freelancers and remote workers, where you can receive the best freelancing advice by talking directly to experienced freelancers, including Matt in a private community focused on helping you learn the business of freelancing. 


Connect with Matt Olpinski:

http://mattolpinski.com/ 

http://madebymatthews.com/ 

http://www.linkedin.com/in/mattolpinski/ 


The Freelance Institute – A community for freelancers and remote workers. 

http://mattolpinski.com/community/ 
 

Connect with First 10 Podcast host Conor McCarthy: 

http://www.first10podcast.com  

http://twitter.com/TheFirst10Pod 

http://www.linkedin.com/in/comccart/ 


Resources:

The Blueprint by Brendan Dunn 

http://brennandunn.com/

http://www.goodreads.com/book/show/17607204-the-blueprint  


Useful business tools: 


A proprietary business communication platform: 

http://slack.com/ 


A visual collaboration tool:

http://trello.com/ 


A community platform for creators:

http://circle.so/ 


Produced in partnership with podlad.com

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Matt Olpinski (00:02):
Your first client could be just one connection
away from the people that you'reactually talking to. So I think
everyone nowadays they want tojump on these job board
websites, and I think there's alot of missed opportunity with
with personal networks.

Conor McCarthy (00:21):
Hello, listeners, and welcome to the
first 10 podcast. I'm your hostConor McCarthy and in each
episode, I interview BusinessBuilders on their first 10
customers, who they were, howthey found them, how they talked
to them, and what effect theyhad on their business so you can
learn what worked and whatdidn't. When I'm not recording
this podcast, I help BusinessBuilders find their first 10

(00:41):
customers and grow theirbusinesses. I do that with one
to one coaching and a series ofonline workshops. So please do
check out my website atConorMcCarthy.me for more
details, and to sign up to mynewsletter. I hope you enjoy
this show. My guest today isMatt Olpinski. Matt started his
freelancing career kind of byaccident, he was building
websites for friends and familyand one day realized that he was

(01:03):
doing the work of a freelancer.
And he realized that it was alife that he really enjoyed, and
he wanted to grow into it more.
So he started selling hisfreelance services, or as he
puts it, quote, 'operating as afreelancer'. And the rest, as
they say, is history. And that'swhere we spend most of our time
on this episode, it's talkingabout what it looks like to
operate as a freelancer,We cover about the journey from

(01:23):
taking his work from being aside hustle to being a full time
job, all while having a safetynet of a consistent income
before we made the big leap. Andalso a bit switching into the
mindset of being a professionalfreelancer, and what that looked
like when he started pitchingthis to his clients. Matt has
also successfully transitionedfrom being a freelancer into
running an agency. And we talkedabout the reasoning behind that,

(01:46):
and what it's taken to get thatup and running. Lastly, as if
Matt wasn't busy enough, helaunched an awesome freelance
community called the freelanceInstitute, when he saw that the
help he was providing toindividual freelancers could be
amplified within a communitysetting. This is a great
episode. And Matt is verygenerous and shares a ton of
great insights for freelancers.

(02:07):
So please do enjoy this episodewith Matt Olpinski.
So Matt Olpinski, first of all,thank you very, very much for
taking the time to be here withustoday.

Matt Olpinski (02:20):
Of course, thanks for having me.

Conor McCarthy (02:21):
So do you want to go back in time and tell us
about how you got started inbusiness?

Matt Olpinski (02:26):
Yeah, I'd love to. Um, so when I first started
freelancing, I didn't know thatI was freelancing. It sort of
started by accident, I was afreshman in college. And I had a
friend who was in my major, andhe was doing work on the side.
So basically, I saw peoplepaying him the different

(02:48):
different companies paying himto create websites, which is
kind of what we were in schoolfor. So I was like, well, that's
great to get paid for whatyou're learning to do in school
while you're in school. So I waslike, let's, you know, that'd be
great. So we started doing thattogether. And my first time
clients were really, from mypersonal network, people that I

(03:09):
knew, those are my, my personalfirst 10 clients were just
people that I knew it was anonprofit organization that gave
me a college grant, a lawyer,like a family lawyer, that my
mom, you know, recommended. Allvery personal, personal, you
know, connections, and then alsoprojects that I had kind of
working with that friend, duringlike, kind of, you know,

(03:32):
freshman year of college. Sothose were, those are my first
first time clients all came frompretty much word of mouth and
direct network referrals.

Conor McCarthy (03:40):
Okay, yeah.
Sounds like some kind of lowhanging fruit as if they were
they're almost waiting to havethe websites built.

Matt Olpinski (03:45):
Yeah, exactly.

Conor McCarthy (03:46):
So what was your main learning in that time about
either the kind of the businessof creating websites or the
business of being a businessperson, if you know what I mean?

Matt Olpinski (03:55):
I didn't know that I was even being a business
person. The concept of theconcept of, of the business of
freelancing never really evencrossed my mind. It was like, I
know, I know how to do and it'sfunny, because I was actually
still learning how to do it.
Right. I was early in college.
So this is my first experience,even doing websites, you know,

(04:17):
designing websites, buildingwebsites. And what I realized
early on was that when I was incollege for design, not not
development, so what I learnedearly on was that when someone
asked for a website, they didn'twant Photoshop files, they
wanted a working website. So Ilearned how to code and started
coding these, you know, simplemarketing websites. I didn't
know they were simple at thetime, because again, I was very

(04:39):
early on, but these very simplemarketing sites and people were
paying me to do it. And I didn'treally think much beyond that. I
don't even I don't even reallyremember the word freelancing
really coming up much in any ofthe conversations that I had
spread to mine, or in any of theconversations that I was having,
you know, outside of that. So Ididn't even really understand
what I was doing. It was justlike people were willing to

(05:00):
paying money to have websitesand I was willing to do them.
And that was money I could makein school without having to have
like an on campus job orsomething. So that was how it
all got started. And I neverreally thought much beyond that.
And I never even once I realizedthat I was freelancing, you
know, years down the road, thatit never even occurred to me
that that's what I wanted to dofull time, my trajectory in

(05:21):
college was still to, you know,graduate, get a full time job at
some design agency, and workthere full time. And if I if I
wanted to still freelance Onnights and weekends for, you
know, extra money, but that wasthat was the extent of it. So we
can get more into the transitionof how I became a full time
freelancer. But that's that'ssort of how that happened in the

(05:42):
beginning.

Conor McCarthy (05:42):
Okay. So interesting, because, you know,
so I get the impression you didthis for a number of years, you
just basically, you, quote,unquote, did the work you just
that was it, you did it, therewas no kind of tag or label of
Freelancer? But was there wasthere a moment where you said,
I'm gonna wrap this at afreelance package and sell it
officially?

Matt Olpinski (06:00):
Yes, there was a moment, because that was pretty
much the same moment that I wentinto freelancing full time. So I
was doing freelancing allthrough college on the side
nights and weekends, graduated,got my, you know, expected job
at a design agency, and workedthere for three and a half
years, and was still doingfreelance work on nights and

(06:20):
weekends, because I reallyenjoyed it. And it was extra
money. And, you know, why not? Iwas getting better at it. And I
had the time to do it. So Ifigured, you know, why not. And
then there came a point where,but so I want to add on to that
a little bit, what what collegewhat college design teaches you
is to have a portfolio website,right, have a portfolio website,

(06:42):
so that you can get in front ofdesign agencies so that they can
evaluate your work so that youcan get hired. And then once you
get hired, that's kind of it. Soyou're not you're not really
taught to have a businesswebsite, or, or a marketing
website, you're taught to have aportfolio site where you display
your work, and the strategybehind those two things is
pretty different. So up until Iwas well into my job at a design

(07:05):
agency, I still just had aportfolio website and never
clicked that I needed totransition, how I positioned
myself on the website. So oncethat clicked, the types of
freelance projects I wasgetting, were that shifted, they
were bigger, they were better.
And I was positioning myselfmore as a freelancer and a
business. And I was operating alittle bit more that way as

(07:28):
well. And that sort of propelledme into a scenario where it was
feasible for me to go full timefreelancing. And it caused me to
realize that maybe there's maybethere's more to this, like,
maybe this can be morelucrative. Maybe I'll enjoy this
more. And that was really thepoint where I said, Okay, like,
now that I have this, thiswebsite as like the foundation

(07:49):
of my career, that was what Iused to sort of go, you know,
full time freelance, so Okay,

Conor McCarthy (07:58):
okay, right. And so the first thing you said in
there, like use the phraseoperating as a freelancer, what
was there anything about that,that you can tell us more about?

Matt Olpinski (08:09):
I think it was, it was mostly a mindset shift,
more than anything, it was, itwas the way that I communicated
with clients, you know, I wastreating myself and thinking of
myself as a business, someonewho could deliver value, not
someone who could execute tasks.
So like, my mindset was, I'mconfident that I can do this for

(08:30):
you, and it's worth X amount ofdollars, versus I'm willing to
take any job just to get paid.
So So there and again, that wasthat was a, I want to say quote,
unquote, risk that I could take,because I had a full time job,
right, there was like, almost norisk. So the whole time, like I
got to experiment with, with howI positioned myself and what was

(08:51):
working and what wasn't andnavigating these, these new
conversations and adopting thisnew mindset. From a business
perspective, you know, I wasstill writing, I was still
writing proposals, I wasimproving my proposals. Most of
most of it was just positioningon the marketing side. And the
way that I the way that I washandling conversations with with
clients just just shifted alittle bit and think of when you

(09:12):
really get into the nittygritty, it was more competence,
higher rates, being able tostand behind things, being able
to communicate value to a clientand not just say, you know, when
people ask why, you know, whyare things this much money? It
wasn't? Well, that's the marketrate. It was, well, this is this
is how it affects your business.
And this is why it's worthwhilefor your business to be paying
this amount of money, becauseyou're going to get something

(09:33):
else out of it something greaterand value out of it, you know,
it's an investment, not anexpense. And there was there was
that the difference in how I wasable to communicate that is
really what changed.

Conor McCarthy (09:44):
Okay. Right. So, so many interesting facets to
that. I mean, would you say the,you know, narrowing in and
getting your positioningstraight, was that, did you try
a couple of differentpositioning statements for this
column, or did you just kind ofpick one and run with it?

Matt Olpinski (10:00):
I think I tried a few so my my process I guess for
updating my website andmodifying my website, which
again is really has reallyalways been the anchor of my
entire career has, well,basically what was going on was
i would i would adjust adjust itwhen I felt like I needed to
adjust it, there wasn't reallymuch of a plan, it was kind of

(10:22):
like, okay, I've had thistagline up on my homepage for a
while now. And I think I found away to make it better based on
what I was learning along theway. So then I would go in and
prove it. Or I had aconversation with a client that
made me realize I need to besaying X, Y, and Z somewhere on
my website instead. So I wouldjust make those changes kind of
as I got feedback. So it waslike this very iterative thing.

(10:45):
It wasn't like, you know, I hadone big moment where I just
realized everything needed tochange. And I nailed it and got
it right. And everything wasbetter. From there. It was just
sort of like experimenting. AndI tried not to change it too
often. Because I you know,obviously you need to give it
time to succeed or fail. Butyeah, there definitely went
through a few different, youknow, titles and taglines and

(11:08):
things like that, you know.

Conor McCarthy (11:10):
So apart from doing the actual work and
getting feedback from clients,and actually putting their
feedback to use? Were there anywebsites or books or resources
that you used to upskillyourself as a freelancer?

Matt Olpinski (11:24):
Yes, one of the resources that was very
impactful for me that reallymade a big difference for me
was, I think it was called theblueprint by Brendan Dunn with
Double Your Freelancing. So theBrendon and Double Your
Freelancing was really like thatlightbulb moment for me that was
like, wow, like, I read, I readthat book, the blueprint, and it

(11:46):
really changed my perspective onon positioning, it was like, you
know, the clients investing inme versus, you know, just
looking at my work as anexpense, being more confident,
providing value, all of those,all of those things like and
once that that moment happened,once that kind of clicked in my
head, I was able to run with it,you know, more or less on my

(12:08):
own. But that was that wasdefinitely a resource that
completely changed the way Ithought about my positioning and
how I treated myself operatingas a business and, and all that
great stuff.

Conor McCarthy (12:20):
Okay, really interesting. Yeah, because the
positioning, I mean, you deal alot now with freelancers and
positioning must come up a lot.
Are there any other kind ofbuckets that come up that you
you had to figure out yourselfthat, you know, give advice on?

Matt Olpinski (12:35):
Oh, man, um, you know, I don't know if I have
any, any one bucket per se, inparticular, I think it's more
like, everyone's got a differentopinion on things. So like, a
lot of people will tell youlike, the best thing you can do
is like niche down and be morespecific, right be like that's,
that's the the general generallyaccepted advice is like, Be as

(12:55):
specific as you possibly can beabout what you offer and who you
offer it to. And for me, whatalways seemed to work really
well was being a little bitmore, a little bit more generic.
And I've gotten a little morespecific over the years, but it
was basically like, I'm a UI, UXdesigner for web and mobile, and
I can design and develop reallygood websites. And I know, the
UX side, and I know, the UIside. And I can also code them

(13:19):
as well. So you know, bonus foryou clients. I can all you don't
have to go hire a developer. Sothat and that always worked for
me. So for me, that worked. Idon't know if that would be
necessarily advice that I wouldgive to other people saying that
this will also work for you. Butso I think when I have these
conversations with people, I trynot to be too prescriptive with,

(13:41):
with what I'm what I'm saying,and and sort of learn about
their specific situation andwhat may or may not work for
them. Because it may bedifferent than what works for
me.

Conor McCarthy (13:52):
Okay gotcha. And was there a moment? I mean, it
sounds like you, you had asteady stream of work coming in.
And then suppose you got intothe, quote, operating as a
freelancer mode. Was there amoment where you had to take on
people to help you do the work?

Matt Olpinski (14:07):
I'm only getting into that more recently.

Conor McCarthy (14:09):
Okay, what's that like?

Matt Olpinski (14:11):
Yeah, so the so the timeline on that was in
2015, I went full timefreelance. And I wouldn't
necessarily say that the workwas that the new work coming in
was steady, what the actuallythe main way that I sustained
myself for the first coupleyears was through a really long
term, like retainer agreements.
So I would work with one client20 hours a week for six months,

(14:32):
and then we renewed thatcontract for another six months,
and then another six monthsafter that, and then I have a
different client, or a coupledifferent clients that were
fixed projects that wereshorter, shorter term, kind of
alongside that and like theother 20 hours a week. And then
once that long term contractended, I ended up having another
one with a different client thatended up being renewed for like

(14:53):
three years. So it was it was,you know, an in between, I
wouldn't say that the theadditional work coming in wasn't
necessarily steady. But I didhave at least one thing that
grounded me along the wayfinancially. So that there was
there was some steady income inthat regard. But the the steady
influx of new work, you knowthat I don't know if it was

(15:14):
necessarily a steady influx ofnew work. And then in 2018, I
repositioned again into a smallagency versus a freelancer. So
my freelancing site became ablog and a resource center for
freelancers. And I have aseparate site now for my
company. And that has furtherhelped me grow and expand and

(15:34):
take on even bigger projectswhere I can subcontract parts of
it and it sets a differentexpectation with the client.
When I feel like when clientswork with a freelancer, they're
expecting to work with afreelancer and not to have the
freelancers subcontracted toother freelancers, when you have
a company or a small agency, theexpectation is that you're not
going to be the only one workingon this, I'm expecting that

(15:55):
there's probably more peopleinvolved. And I'm okay with
that. So and that's, that'sreally what I wanted to start
getting towards. So that was oneof the big reasons why I shifted
to a company versus freelanci

Conor McCarthy (16:08):
That's yeah, that is really interesting and
makes a lot of sense. From theclient perspective. I was it was
it uh, how was it transitioningfrom I do all the work to I
outsource right delegate or Ishare the work.

Matt Olpinski (16:19):
It's been slow, slow, for a couple reasons. One,
one, because I am sort of atthat that point right now where
I don't have so much work comingin that I can like, constantly
be delegating to other people,there's seasons where I'll have
enough time to do all the work.
And then other seasons where Imight need to hire one or two

(16:40):
people for miscellaneousprojects, and then a different
project, that'll be like 12months long, and I need I need
to subcontract someone for likea year. And so it's been partly
that. And it's also been partlythat, I'm just so used to doing
all the work. It's been hard,it's hard to trust other people
completely sometimes. So I'mstill learning how to, to how to

(17:01):
do that effectively, and how togrow and how to scale and I'm
also wrestling with whatdirection I even want to take
the company, you know, do I wantto eventually be hiring people
full time? Do I want to justkeep it, you know, kind of where
it is now? And maybe justsubcontract more, but then do I
get into like a managerial rolewhere I'm not doing as much
work? And I'm just sort ofmanaging things? And is that

(17:22):
really where I want to go? SoI'm just sort of trying to
navigate, you know, what, whatdirection I want to go. And
until I have a more clear visionon what that is, I'm just kind
of taking it one day at a time.

Conor McCarthy (17:35):
Okay, interesting. Yeah.
I hope you are enjoying thisepisode and that theres some
actionable and insightful advicethat you can take to your
business. Helping you identifyand create those First 10
Customers is what I do, so ifyou like what you hear on this
podcast and want moreinformation, including a bunch
of free resources on how to findyour first 10 customers and grow

(17:55):
your business, check outfirst10podcast.com or find me on
Twitter @TheFirst10Pod. Also,podcast reviews are more
valuable than you would realize,and Id really appreciate if you

(18:24):
could take 2 minutes to jump oniTunes and leave a review of the
First 10 podcast. Thanks. Nowback to the show.
I was gonna ask you about like,how do you find good people? And
I know you're still on thatjourney. But do you have any
tips for freelancers who arelooking to partner or delegate,

(18:47):
etc. Any tips on hiring?

Matt Olpinski (18:51):
Well, the one the one way that I've been able to
do that, as I actually started,I'll plug this real quick
because it's it's actually whatworked for me I started the
community for freelancers,because I run a newsletter and a
blog and a lot of people writein and they ask really good
questions, and I was answeringthem. And I was, I found myself
wishing that more people couldbe participating in that

(19:12):
conversation and and getting thevalue from the answers that you
know, or the question andanswers that were being asked
over email kind of privately. Iwas like, this would be really
helpful for other people too. SoI started this community and met
a whole bunch of really greatpeople through there really
talented designers anddevelopers and marketers and
copywriters, and people likethat. And then a lot of them

(19:33):
I've hired maybe like, five orsix different people for various
projects over the last two orthree years from from that
group. So I say look for lookfor communities, online
communities for freelancers,online is a great way to network
with other people who you knoware available for subcontracting
or who have projects that theyare subcontracting.

Conor McCarthy (19:55):
Okay, interesting. Yeah, I mean, let's
talk with community for a secondbecause it is I think you've
you've done a great service herein taking, what were private
communications that were stillfull value, like real questions
that freelancers have, and kindof going. Let's put this out to
the world. So, yeah, well, wasthere again, was there a moment
where you said, I'm gonna starta community? And this is what
it's gonna look like?

Matt Olpinski (20:14):
I think so. Yeah.
So there was one conversation inthis sort of built up. But there
was one one particular momentwhere I said, okay, I've been
answering a lot of emails thisweek. And there was, I remember,
there was one person who emailedme. And she said, I am trying to
transition from televisionproduction to UX design, What

(20:34):
tips do you have? and you know,it's like, that is such a
specific thing. Like, there'sFirst of all, there's no way
you're gonna find an answer tothat on any blog, or anything
like that. And, and thetransition from one thing to
another is so unique for everyperson, like it's not just a
matter of one industry toanother. It's, there's all kinds
of factors that play into whatwould make a transition like

(20:55):
that successful. And I was like,man, I can give you my best
advice. But I really wish therewas some other people in this
conversation who might be ableto weigh in, because I'm just I
only have one perspective, whenyou can ask a question and a
whole bunch of people cananswer, it's, it's better for
you. And we're all communicatingwith each other. So I said, You
know what, I think I think Ishould start a community for
freelancers where we can alltalk about stuff like this, and

(21:17):
other people can weigh in. Andso that was that was when I
decided to start, it's calledthe freelance Institute. That's
when I decided to start thefreelance Institute. And it
started as a slack group. Andthat went pretty well, for a few
years, we recently transitionedto a different platform called
circle, which is a little moreconducive to the types of
conversations things don't getlost as easily. And it's, it's

(21:38):
been really nice to haveconversations there. So that's
sort of where we're at. Yep.

Conor McCarthy (21:44):
Yeah, Okay cool, like, the word community, as, as
you know, as I see, it's beenthrown around a lot at the
moment. And and sometimes it canfeel like an add on to when you
see certain some companies kindof going on this community. What
what makes a good community?

Matt Olpinski (22:00):
Oh boy, I think I'm still learning that myself.
But I can speak to is, you know,obviously, engagement. I mean,
you want people to be engagedwith each other, you want good
conversations, I'd rather have asmall community with really good
conversations than a bigcommunity where people feel
lost, and like, no one's reallynoticing them. So I think I
think that's a big part of it. Ithink the community managers and

(22:23):
community leaders like like,prompting conversations and
things like that are veryhelpful, especially for
communities like mine, what Ican speak to is, I noticed very
clearly there was sort of twodifferent types of communities
there is individuals likemyself, and this was a decision
I had to make was, there'scommunities where an expert will

(22:44):
create a community, like yousaid, as an add on to something
else, maybe they have otherproducts that they're selling.
And then there's also thisprivate community where you can
talk to this person, andeveryone joins, hoping to talk
to that person, they don'treally join, hoping to talk to
each other. So So there's that.
And then there's othercommunities that are sort of
like independent, were theremaybe a few people running it,
but it's mostly just everyonegets to connect with each other.

(23:06):
And that's really what I wantedto create. I didn't want to
create a community where I wasbasically doing the same thing
over, you know, Slack, because Iwasn't the email, I wanted to
create it. Where people aren'tjust joining for me, they're
joining for community they'rejoining, to network with other
freelancers where I don'tnecessarily need to be involved

(23:27):
every single day for there to bevalue being provided to the
members, you know what I mean?
Like there can be conversationshappening between people,
without me that are that arevery valuable. So yeah, that's,
that's that's sort of thedifference that I observed.

Conor McCarthy (23:40):
Yeah, that's really interesting. I heard it
described recently as being, youknow, an audience. If you think
of like an audience at aconcert, they're waiting for the
main act to show up. And thenit's almost like everyone's
looking in one direction,they're looking at the main act.
But a community is morehorizontal, everyone's talking
to each other. And it shouldn'tlead Matt to show up to, to help
people engage.

Matt Olpinski (24:00):
Right. And part of that was scalability, like
I'm doing a whole bunch ofdifferent things, right? Like,
I'm running my company, I'mrunning a newsletter, I'm
running a blog. So starting thecommunity, and having everyone
looking at me was, you know, notsomething I thought we could
scale very well. Yeah. Like, andthere's, you know, once you get,
I don't know, I don't know whatthe number is, but let's say a
few 100 people in there, thatwould be incredibly overwhelming
for me to always feel like Ihave to be in there answering

(24:22):
questions. So I decided to go adifferent route and just create
an independent community that Istarted for freelancers, where
you can join and ask questions.
That's really the main, the mainfunction of the community and
there's lots of topical spacesin there, like getting clients,
portfolio websites, financialmanagement, client
communication, emailcommunication, all these

(24:43):
different topics. And the goalis really to have new
freelancers with lots ofquestions, ask those questions,
and get responses from lots offreelancers. It's been really,
really valuable. So there's veryunique questions that come up.
It's not just like how do I getmore clients but if you can Tell
us more about you specifically,and what's going on in your own
career. And we can sort ofnavigate that, right? There's

(25:06):
lots of follow up questions andback and forth. And what I found
is that rather than just readinga blog post that may leave you
with more questions thananswers, you can actually talk
to people about your uniquesituation. It's less generalized
advice. And it's much morespecific and tailored to you.
And that's been really valuablefor people. So that's really why
I started it, it's not atraining platform, it's not,

(25:26):
you're not going to get coursesand educational content sort of
delivered to you on demand, it'sgoing to be more interactive and
engaging. And I think thatthat's something that I
certainly wish I had when I wasnew to freelancing, it's just
other freelancers to askquestions to. Because there's so
many things you don't know, as anew freelancer, it's like, where
do you look? And sure, you cangoogle stuff. But it can be hard

(25:48):
to find, you know, even then,what's the right advice? Right?
Like, you find three or fourdifferent articles that all say
different things. So which whichone do you follow? So that's,
that's really why I started it.
So it's a place wherefreelancers can can learn can
learn from one another.

Conor McCarthy (26:07):
You pointed out there that you do a lot, do you
have systems in place to manageall the different parts of your
empire?

Matt Olpinski (26:16):
I wish I had something a little more concrete
to share. Not Not really, I haveI have to do lists and Trello
boards, but not much. Not muchbeyond that. What I what I have
sort of observed looking back iswhat will happen is I'll go
through a season where I have,you know, let's say for its for

(26:37):
the community, I have a visionfor like how I can improve it.
And I'll spend a few weeks kindof buckling down and like
improving it and doing all thethings related to that
improvement. And then that'll bedone. And then I'll look at my
company website and say, oh,there's a whole bunch of stuff I
could do over here. And thenI'll take a deep dive into that.
And then go work on that untilthat's done. And then I'll look
at my blog and my newsletter andsay, Oh, well, I haven't worked

(26:57):
on that in a while. And then bythe time I get done with all
those things, I'm back to thecommunities.

Conor McCarthy (27:00):
So it's circular process, circular process,

Matt Olpinski (27:04):
That tends to be what happened. I'm not
necessarily saying that that'sgood advice. But that's Yeah,
tends to be the pattern.

Conor McCarthy (27:11):
There's a kind of an organic kind of go where
you're needed aspect to it,which, which I appreciate it
like that. And just as a lastquestion, I'd like to ask all my
guests, what would you say tosomeone who's just starting out
to find their first 10customers?

Matt Olpinski (27:25):
Well, I can only I can only speak from my
personal experience. But I wouldsay leverage your network. I
think when I startedfreelancing, there weren't all
these, you know, gig platforms,there was not a lot online
available for freelancers,especially in terms of finding
new jobs. So I didn't reallyhave a choice but to leverage my

(27:48):
own personal network. In fact,there was one summer where my
friends and I went door to door,like all the old time like,
literally literally walking intobusinesses and saying, Hey, we
do websites, do you need one?
Wow. And that did not work, Iwould not recommend. But we did
it. And and it was just thatkind of work. It was just making
sure that you are being kind topeople and meeting people

(28:11):
everywhere you go and lettingthose people know what you do.
Like no matter where you go, ifyou go to like a birthday party,
or any kind of any kind ofevent. I know that's been
tougher recently. But any kindof event where you're where
you're around other peopletrying to, you know, work into
the conversation, like justletting people know what you do.
And and you'd be surprised howfar that really goes. letting

(28:33):
people know what you do andasking, asking even potentially
for work. If my first 10 clientswere just sort of word of mouth.
Because even if that personyou're talking to doesn't need
your service directly, they mayknow someone who does. So your
first client could be just oneconnection away from the people
that you're actually talking to.

(28:53):
So I you know that that workedreally well, for me just
starting out. I think everyonenowadays they want to jump on
these job board websites. And Ithink there's a lot of missed
opportunity with with personalnetworks. So I would say just
try to like communicate with thepeople that are around you. And
and see what happens. I thinkthere's, there's a lot of

(29:13):
opportunity.

Conor McCarthy (29:14):
That's, that's really amazing to have. And I
think you hit the nail on thehead there when you say that,
like when you Google thesolution or your questions or
whatever you do get tons ofinformation. But it could be
hard to translate that into yourspecific situation. Whereas in
communities that I'm part of Iknow it's amazing to reach out
to a person who's done it andget a very direct response. And

(29:37):
then you're in a properrelationship conversation. So
yeah, I'm a big big believer inthe power of communities. And
yeah, I do suggest listeners,check out the freelancer
Institute, because it's full ofreal people with real, real
answers to real questions.

Matt Olpinski (29:50):
Yep, exactly.

Conor McCarthy (29:51):
Matt, thank you very, very much for taking the
time to be with us. You've beenvery generous and sharing your
journey. I know people will bechecking out your website. And
all the links will be in theshow notes, etc. Thank you very
much for being on the podcast.

Matt Olpinski (30:04):
Thanks so much for having me. I appreciate it.
Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.