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Get inspired! Real stories, advice, and revenue numbers from the founders of profitable businesses ⚡ by @csallen and @channingallen at @stripe Get inspired! Real stories, advice, and revenue numbers from the founders of profitable businesses ⚡ by @csallen and @channingallen at @stripe

Transcribed podcasts: 277
Time transcribed: 11d 5h 6m 45s

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What's up, everyone? This is Cortland from EndyHackers.com. Today, I'm sitting down
with Brennan Dunn, the founder of Double Your Freelancing. How's it going, Brennan?
I'm good. How are you, Cortland?
I'm doing excellent. Super excited to have you on the show. We got a chance to talk briefly
at MicroConf a few weeks ago. Can you tell people who are listening a little bit about
yourself and what it is that you do?
Yeah. My main business is DoubleYourFreelancing.com. It happened by accident, which I guess we'll
get into. What I'm doing nowadays is I'm helping creative freelancers understand the
business behind their business. I'm helping them with pricing, with getting clients, with
pitching, and all the stuff that people wish we didn't have to do but is part of what comes
with running your own independent freelancing business.
It's really interesting because I think there's a ton of parallels between the types of things
that freelancers maybe avoid doing naturally but that they need to do and that the founders
of internet businesses also avoid doing that they maybe need to do. Just a couple examples.
This comes from my history as a freelancer too. I never wanted to reach out and find
clients. Then as an entrepreneur, I never wanted to reach out and find customers or
ever just pricing. As a freelancer, I never really wanted to raise my rates and I was
scared people weren't going to pay me the rates that I probably deserved. As an entrepreneur,
I always kept my prices way too low and I could have easily doubled or tripled those
things.
I think a lot of the things that you're teaching people are super just broad business skills
that are useful for everybody. I'm really excited to get into it.
I was going to say most of the people in my audience actually, it's funny, the majority
of them are self-identified freelancers but most do want to end up selling products.
The interesting thing is that a lot of them, what they end up doing in their own consulting
business like setting up a sales pipeline and automating a lot of that along with getting
pricing rate and everything else directly translates into their product business. It's
kind of like all they're really going from is high-touch sales to low-touch sales but
for the most part, all the other stuff maintains. It's not as different I think as a lot of
people think. It's just a different type of fulfillment. It's not software, it's manual
and otherwise it's high-touch sales typically versus show up at the website, plug in the
credit card and go.
Exactly. It's just a lot of overlap between the two. Can you talk about your career as
a freelancer? How did you get into freelancing? Do you still do freelancing right now?
Yeah, so I started back in 2006. I guess you could say I'd done freelancing without really
knowing it. Earlier than that I was just kind of had day jobs or when I was in college and
always kind of did building websites and stuff on the side but in 2006, it became a little
more official. I went out on my own and I started actually working with Bay Area startups
who needed help with their Ruby apps. I was doing that remotely and I had no idea what
I was doing. I just became kind of like an augmented member of their team. I priced according
to what the equivalent hourly rate of their in-house personnel were charging or were getting
paid I should say. I did that for a while and then in 2008, I got to the point where
I had enough referral work that I could either turn away work or grow a team. I decided to
grow a team. Again, not knowing anything about managing a team or managing people or anything
like that. A few years later, we had gotten to 11 full-time employees. We were doing a
few million a year in revenue. We had a brick-and-mortar office here in downtown Norfolk, Virginia.
It was by all accounts successful but the issue was I had a lot of friends who were
running these SaaS businesses and I was building effectively web apps for my own clients because
we were doing a lot of work for startups who needed us to build their MVP and whatnot.
I wanted to do it myself. I wanted to have a lot of people pay me a little bit of money
instead of a few clients paying me a lot of money. I started an app called PlanScope
and I realized it was really difficult to run an agency and a software company simultaneously.
I exited the agency to focus full-time on PlanScope. PlanScope is a project management
and it's a project management that I built for small agencies and freelancers, so people
like me. Like a lot of new-time SaaS founders, I really struggled to sell it. I really struggled
to get it in front of people. I had read about content marketing and I was reading up on
that and I started creating articles about freelancing that had nothing to do with project
management but that helped the target demographic. That ended up doing really well and I got
people who showed up, read a lot of my content but didn't care at all about the software.
They just wanted the content and eventually that led to me writing an e-book which was
as an engineer was really hard for me to do because I thought the e-books were all BS.
I did that. It ended up working really well and I wasn't getting slammed with refund requests
instead people were saying like this is really good and then I started getting testimonials
and people writing in who I'd never even talked to saying you've literally changed my life
I don't know you but here's what happened. One thing led to another I created additional
courses and workshops. Now that's my main business and we run two conferences a year,
one in the US, one in Europe. We just crossed over 10,000 customers and we've got an audience
out of about 40,000 people. It's doing really well and last year beginning of 2016 I once
again realized it was really hard to run two companies so I sold PlanScope so I could focus
on Double Your Freelancing. Double Your Freelancing at first was a content marketing initiative
for my SaaS. It ended up exploding in success so I then realized I wasn't able to build
and support the SaaS the way I needed to considering all that was needed of me on on Double Your
Freelancing side. So are you full-time on Double Your Freelancing or do you do any consulting
on the side of that? No I mean I occasionally do just because I'm big automation geek so
most of the business is now fully automated so I do occasionally consult but not much
and I've actually just started a new SaaS called RightMessage which is my official entry
back into the world of software and I'm trying to do a lot of what I've done manually on
my own website so I've done a lot with automatically changing the copy and the content of my website
depending on kind of like what you do or what stage your business is in and what you want
for me. I've been doing a lot of that but more manually and a lot of people written
in saying can you make this easy for me to do so I'm basically we're almost ready to
ship the first version of this new new SaaS that I've been working on for the last few
months. Cool and just for some context I know you're pretty transparent with revenue numbers
can you talk about how successful Double Your Freelancing has been in terms of revenue
and also PlanScope? Yeah so DYF and I just ran the revenue report over the last year
did about 900,000 so it's pretty nice in the sense. That's huge. Yeah I mean it doesn't
it's cool because it you know it just it works right I mean I'm able to there's very minimal
support I've got a full-time assistant who handles a lot of the frontline support but
for the most part I'm able to focus on kind of creating new content upgrading my courses
and making them better and and everything else but also getting to play with a lot of
the fun things that I've been really geeking out on like you know automation and personalization
and just really focused on how can I how can I make it again my mission for last year has
been if I were to go into a coma this should still work so I've been doing a lot with doing
things like observing behavior on my site and then when they hit certain things or when
they reach certain thresholds to automatically pitch them on certain products of mine and
it's just been it's been steadily climbing over the last few months and yeah it looks
like we're on track for probably at least one and a half million this year yeah that's
that's huge especially considering how small your team is I mean you're basically a team
of just one person it's just me and then I've got yeah I've got a full-time assistant on
retainer and then I've got a few people who helped me but it's pretty much just me although
we do have a kind of like a daily coaching offering called the expert roundtable which
is where I've got consulting coaching friends of mine who are pretty authoritative in whatever
niche they work in who make themselves available for a coaching call daily and that's a that's
kind of our only other expense outside of my admin assistant and a few random freelancers
who I hire on project basis so it strikes me that you've done a lot of oscillating between
freelancing and then a product business and product business and freelancing at the same
time and then freelancing you know into teaching a course and then now back into a product
business are there any similarities and parallels you've you've carried between all those disciplines
that you found are helpful across every one of them yeah I mean I think so the mistake
I made with my agency was all of our business was transactional so we didn't have any recurring
revenue with plan scope I got a my first taste of kind of you know subscription revenue it
was really nice but it was really hard to grow and the issue that I had and the thing
I learned about growing plan scope was it was a habit-based app meaning I had to get
people to change their habits for it to work for them so with project management software
especially mine which is very very opinionated about how you should work it was really hard
to get people to convert and when we did get them to convert because they're freelancers
there wasn't a direct correlation between signing up and getting some sort of ROI so
you know I learned a lot then and I learned a lot about kind of the business of running
a higher scale software business you know with with with consulting with an agency you're
very intimate with your clients and you've got a lot of overhead very little margins
though typically with software was the opposite so virtually no overhead and but a lot of
lot of support a lot of you know I had to get okay with the idea of like not bending
over backwards for literally everyone who joined or who was a customer now with double
your freelancing it's largely a transactional revenue business so like the agency it's typically
one-off sales but it's at very high volume comparatively so I've again it's like I've
learned from PlanScope about high volume I learned from the agency about kind of how
to do a lot of these one-off sales and how to how to build a bit a proper business I
mean that was really my first business and now with you I have I'm learning how to predictably
generate a lot of one-off sales and now with the new SaaS I'm taking all that collected
knowledge and I'm working on how can I have a highly scalable business finally that has
predictable monthly subscription revenue so it's kind of like each business even though
they're very distinct and both in model and even audience I've learned from each some
core concept that I've applied to the subsequent business and that's been I mean that's you
know I'm very big on just experiment does it work yes if yes great keep doing it otherwise
figure out why it didn't work and try something new so yeah I mean that that's I don't know
if that answers your question but that's been kind of like my that's how they've all tied
together in terms of like how I've gotten to where I am now but yeah it's it's it's
been quite the interesting ride yeah one of the things that I found interesting listening
to several other talks that you've given and going to double your freelancing is how similar
some of the lessons that you teach to aspiring freelancers and existing freelancers are to
the lessons that people want to learn when they come to Andy hackers so a good example
is just the importance of basic business knowledge like sales and marketing understanding why
customers buy the thing that you're selling and especially why businesses buy things is
almost exactly the same between freelancers and entrepreneurs and it's funny because I
think that we all go through life as consumers with that exception right we all buy things
and then the second we become creators right the second we are freelancers and we're selling
ourselves and our skills are selling a business solution or the second we become entrepreneurs
and we're trying to sell you know a sass product or service to customers it's like there's
a switch where we're just suddenly unable to understand why consumers or businesses
buy things and so it's interesting to see you know the advice that you give to freelancers
about okay here's how you should actually structure your marketing copy right here's
how you pitch your skills and your offerings to businesses in order to get them to pay
you the rate that you deserve rather than you know doing the the default thing that
most people do that's you know just listing you know in the case of an entrepreneur just
listing their their products features or in the case of a you know a new freelancer just
just listing okay here's the languages that I'm going to use etc and doing what you said
you did earlier on which is pricing yourself relative to that company's existing employees
and just saying okay you know here you're paying for my time and my time as a developer
is worth X amount that you're paying your other developers so I think it's just been
really interesting to see some of those similarities I mean I think one of the best things that
I learned when running the agency was when I finally realized that no one was paying
us for code or design or you know whatever it is we were doing they were paying because
they thought that by commissioning somebody to write this code that their business would
be better right like that they would ultimately get some sort of return on investment and
I think a lot of us myself included when I started just thought that my job was to kind
of swing the hammer for them so they needed a Ruby developer so I am here to write Ruby
at this much an hour and you know a lot of the advice I give on pricing it isn't about
like just you know here are some like psychological tricks on how to convince people to pay you
more it's a lot it's more than that it's beyond that what I'm really trying to do is I'm trying
to help people ultimately deliver a better product because the product is more aligned
with the actual need that somebody has right so in the case of consulting instead of just
saying oh you need a website redesigned I can reskin your website try to actually figure
out like why why do they why do they want their site redesigned like what why are they
firing their current website like what is it about the way things are that sucks so
bad that they've seeked out somebody like you and figure out exactly what is it they
really need do they need to generate more leads are they looking to get more sales like
what is the objective they have and then ultimately the purpose of the work you do say the redesign
is with that end in mind so the redesign will be better because you know exactly why they're
winning redesign versus kind of the default thing that a lot of us do which is well let's
talk about what it'll look like let's talk about you know how many pages will have it
you know all these different kind of things that ultimately don't matter but what I've
come to realize is for people like you know us we're engineers it's more comfortable for
us to talk tech it's more comfortable for us to talk about the thing that we know best
the thing we've studied for years and gotten really good at it's a little harder to switch
gears and talk about how what it is we do can benefit a business but once we're able
to do that whether it's through like selling software or selling consulting everything
changes to that point because you're able to then focus on like so for you know the
kind of consulting I do now I mean what it includes is me writing copy setting up automation
stuff for them and doing some light front-end development but in in talking with my clients
none of that ever hits the surface like I don't sell that and you know I'm not advertising
myself as a copywriter slash developer slash can use drip on your behalf kind of consultant
yeah it took me a long time to really internalize the lesson that that you're saying right now
which is that you need to actually understand what your customer is hiring you for you need
to understand what problems they want solved and how valuable those problems are and then
end up pricing yourself relative to like the value that you're delivering versus other
things and I think you know to your point that we're developers and we you know are
very comfortable around the skill set that we've developed and not comfortable around
other things I think that's true across almost every profession so my girlfriend for example
does sex and relationship coaching and she teaches other people how to do it and they'll
gain all these skills by taking her course but at the end of the day they still have
to learn how to market and sell their skill set right it's not just about having that
particular skill set and it's the same with developers it's the same with designers etc
so I think there's something to be said for teaching people how to market themselves and
teaching people how to look at things from a customer's perspective and understand the
value that they're delivering and it's not despite you know us buying and understanding
like why we buy things to a degree it's not easy to be on the other side of the equation
and actually figure out how to price ourselves yeah I was gonna say I mean not to go too
much on the tangent but if you really think about it like the if somebody ends up hiring
somebody like you or I they've already a few things have already happened they've first
off they've realized they have some issue that needs to be fixed second they've realized
that it can be fixed and third they've realized that it can be fixed by working with somebody
like us and you're asking you're putting a lot of like weight on that buyer to go through
that entire process and eventually come to the realization that oh I need a higher Brennan
to do XYZ for me and for everyone who could benefit from me very few people actually make
it through that gauntlet so you know it's it's in our interest I think to when they
do get if they do get to the end of that gauntlet if they do realize okay what we need is a
web developer you're already at that point commoditizing what it is you're selling and
the same is true of like when I was doing project management software if I'm waiting
for people to realize that they have a project management problem I've already lost in a
way right like I've already you know I mean I'm missing out on so much and at that point
they're looking and they're comparing feature set and they're comparing what it is it does
you know the the technicals of the product in this case and you know the example I give
like so for my new startup right message it's website personalization software well how
many people actually know that's possible relative to how many people could benefit
from it very few and that's why what we're doing from the beginning with our messaging
in our marketing is to look at people who demographically fit with who could you know
the kind of people who could benefit from our software and meeting them there and then
preparing them to become customers of ours over time and systematically and automatically
and then by that time now they're the ideal client or so that they're ideal customer of
ours and you know the same is true of consulting it's the same with products I mean it's it
at all the thing that we should be fighting against is backing ourselves into a commoditized
corner and the way to do that is to again the best way to do that that I've seen is
to meet somebody where they are now and lead them and condition them for lack of better
way of letting it to be that perfect customer that ideal customer who fully understands
now you're basically helping them you're kind of you know I went to school for the classics
and we've read a lot of Plato and one of the things that Socrates got named as was
a philosophical midwife so his goal like what he did was he helped people feel like get
to the philosophic awareness that he wanted them to get to through the right conversation
through the right teaching through the right education and you know with products or services
or whatever it is you're selling the same same can be true that the same should be true
in that you're kind of that midwife bridging that gap from where they're right now to where
they need to be in order to be a customer of yours is interesting that you talk about
avoiding commoditization by meeting the customer where they are it's kind of like you're going
to hire up the funnel right so you're not targeting customers who already know exactly
what solution they want and they're just picking from you know a handful of competitors you're
trying to get them before they've made that decision and then essentially educate them
as to why why what you're providing solves their problem is that accurate that's exactly
it yeah because again if you're being comparison shopped at that point I think in a lot of
in a lot of times you've pretty much already lost I mean then the that's when you need
to then compete on pricing or on something like that and again you don't want to be in
that position where the clients have realized what it is they need and they just need a
quote-unquote vendor to to give it to them so let's say because there's a bit of a trade-off
here let's say you're starting a company and you're in a very well-known segment and people
already know exactly what solution that they're looking for the thing that you have going
for you in that situation is that people are already searching for you so in terms of getting
in front of customers there's probably already online forums that exist where your people
are gathered around that particular challenge and you can talk to them there there's probably
popular keywords you can put in that actually have volume around them blogs that are based
around these topics versus the other end of the spectrum if you're going for something
that people might not be searching for if there isn't an clearly defined existing set
of solutions for you have to be a little bit more creative I think in finding customers
and educating them and letting them know exactly what it is that you're doing how do you think
about that problem how do you think about finding people who have this identifying customers
really in the first place and then letting them know why what it is that you're providing
helps them yeah so when I started scaling my agency we quickly ran an issue of having
now a lot of overhead because now we had employees and these employees were pricing and and so
on so I had to find a way to systematically bring in the revenue we needed monthly to
pay our bills the first thing I thought of the thing that I really wanted to make work
was the idea of kind of that finding that perfect unicorn marketplace which you see
this again I mean if you look at like Hacker News I mean monthly there's somebody with
their new freelancer marketplace that they're coming out with because we want this kind
of perfect world where there is an exact alignment between need and offering right where these
ideal clients are just thinking like I need somebody who does this this this and this
and I'm willing to pay exactly what they're worth and then they go to this mythical marketplace
and they find us and the transaction just happens and everyone's happy right that would
be great yeah that doesn't happen though I mean just look at people all you need to do
is go into like the subreddit for freelancing and type in up work and look at what comes
up to see why that's not a good model so to go back to my agency in order to do this we
had to figure out a way how could we get off kind of the luck bandwagon because you know
I mean most freelancers get clients through referrals and these referrals come from past
clients so the issue with that though is we could only create so many clients in a certain
window right like we can only we can't work with hundreds or thousands of clients a year
we can only handle a few so for referrals come from past clients we're limiting you
know our referral pool and what happens if I've got a $30,000 salary next month but we
don't get $30,000 in projects coming in I mean that's that's a big problem right so
one thing that we did and again we I just surrounded myself with people who are a lot
smarter than I was to make this happen we tried this we tried thinking about like why
do these referrals happen why do people refer stuff and ultimately it's because they got
something of value from us they benefited from us in some way so clients you know they
benefited from us by getting ideally a solution of their problems and now they're willing
to refer us when when the opportunity arises so we thought well what if we did something
like what if we just did you know they have all these groups like Chamber of Commerce
is or you know all these different kind of like meetup groups right that meet up that
are I mean out by you've got a ton of these right like these these monthly groups that
meet up that are focused on some technology or some entrepreneurs or something like that
so we basically did offline guest posts where we would go to like the Chamber of Commerce
and we'd say hey I saw I see you have like an education series that you're doing we'd
love to come in and talk about it really kind of like what do you do when you outgrow excel
because a lot of companies I mean they they just use Excel to basically power everything
but they don't actually know that custom software is within reach and could really benefit them
so we were going after people who by virtue of them being a member of this they may or
may not be kind of like a potential client of ours but the fact that they were in this
business community was all we needed so we want we did these you know we did our first
presentation we got like 80 people from that who ended up effectively opting in and again
we didn't have the terminology we had a stupid free MailChimp account we didn't know what
we were doing but we got like 80 people from that first chamber presentation we did we
were terrified to do who wanted to hear more and this ultimately set us off on doing a
lot of these kind of like business seminars which again were just offline webinars think
about it right I mean that's what a seminar is right and we would do these and there wouldn't
be like a call to action of like buy now or anything like that but what we would do is
we would hook people up who went to these on to this really basic stupid MailChimp drip
that would ultimately lead to a hey we'd love to hear what your next steps are here's Zach
who's the the sales guy that worked for me contact him right and we ended up getting
a lot of inbound requests but it was the interesting thing was it wasn't the people who attended
who would usually become clients of ours instead it would be people who attended would get
something of benefit of value from us and then refer us within their own network so
we ended up getting a lot of fortune 500s as clients we had no direct relationship to
these companies but there were people in our network who had benefited from us who then
got us inside you know in the doors of these companies we ended up working in 2012 with
Mitt Romney hired us we had no direct connection at all to that guy but somebody in our audience
and again we didn't even know to call it an audience or anything else at that point but
we were able to kind of the best way I've heard it put is we increased our luck surface
area by encouraging more referrals by having more volume of potential referral sources
and that was really a big eye-opener that is still something I do that to this day with
my online businesses it's the same formula you know but it's online it's more scalable
instead of the offline more the you know in-person events that we do at our office kind of thing
but that what that did is that allowed us to get away from this sort of wanting this
marketplace where people realized oh I need a web development company because again like
one of the things the big eye-opener for me was the first time I started going to local
networking events I remember I just when somebody would ask me like what I did I remember
saying I ran a Ruby shop and these are like southeastern Virginia good old boy kind of
business owners right and they're like I mean they must think I'm some jeweler something
right like they had no idea what I was talking about but that was really a big eye-opener
because you know a lot of these people could benefit from us but there was a disconnect
because we're selling you know you go to so many agency sites or consulting sites and
it's like we make ideas real or we're building a better web or something like that but if
people don't know that they you know is that resonating with the right kind of people I
mean it's gonna resonate with like the MVP crowd the crowd that already like listens
to startups for the rest of us and they get the stuff and you know it's gonna appeal to
a certain segment but is it appealing to everyone is appealing to the kind of people who could
best benefit from you you know I work best not with startups but I work best with established
businesses that I could go in and multiply whereas with a lot of startups who don't have
any revenue or don't have any traction you know multiplying by zero is kind of risky
so you know it was a really interesting eye-opener for me that there was you know describing
myself as a developer it's only gonna appeal to people who have realized they have a problem
that can be solved with the development and if we could go further back in time and help
people along that process you know ideally at scale that's ultimately what got us to
the point where we had you know a multi-month backlog of work for our team of 11 really
at any given time and that directly translated into what I do with the plan scope what I'm
doing now and so on yeah I like how you talk about not relying entirely on luck just waiting
around for people to you know find your business in fact you said you're increasing your luck
surface area right so you're actually going out and talking to people about what it is
that you do and about the problems that they have and how they can solve them efficiently
and you're really just being proactive and going after clients and I know that when I
was a freelancer that's the exact opposite of what I did I just sat around and if people
reached out to me then that's great I would have a job and if they didn't then I would
just go weeks without having a job and it turns out that all the best jobs that I got
as a freelancer were a direct result of some sort of thing that I'd put out into the world
for free some project that I worked on that was popular and somebody said hey I want that
to solve a similar problem for my business and I never really caught on to like maybe
I should you know find a way to do that as a matter of course you know as a an actual
routine part of my strategy I just let it continue to be luck and I think a lot of people
do that with their businesses right if you have a product business you can end up falling
into the same exact trap where especially as a developer you put your head down and
you write code for months and months and months and you never actually think about okay well
who are my customers and what are their problems and what is an effective way for me to get
in front of them and describe how they can solve their problems ideally using a tool
like mine or to get in front of their friends who will then recommend them to me so again
I think this is a great example of a parallel between you know a way that freelancers or
agencies operate that also applies to entrepreneurs you know another thing that you said at the
end was how much your business really not relied upon but but really was structured
to help existing businesses grow which is very parallel to the fact that if you're starting
a business that probably you're going to make more money if you sell to other businesses
who actually have more money because then you're not multiplying by zero right like
you're if you're targeting consumers it's very difficult to find a problem that consumers
are going to pay you a lot of money for because there's not that many consumer oriented solutions
that are going to make individual people a lot of money versus if you're targeting a
business and you have a product or a service even just as a developer right a single as
a single developer the service that you're offering can help any business probably double
or triple or even 10x their revenue right because they need your development skills
if you can price yourself according to the revenue that you're going to help them generate
then you can end up charging a lot more and that goes for product businesses and for just
individual freelancing services so I think that's a lesson that a lot of people could
stand to benefit from even though it's very attractive to target consumers with their
product business you're probably not going to make as much money I mean I've got a funny
story about that so before you know I use I use drip now for email marketing but I used
to use infusion soft and I remember the day I signed up for infusion soft they actually
have a $2,000 setup fee so just to get set up you have to pay $2,000 so I paid that gladly
I knew what the software could help me do I was moving off MailChimp and I was really
optimistic and motivated to transition to what something that I thought would be much
better for sales so I paid this paid $2,000 for the software later that night I was laying
in bed flipping through the app store and I remember balking at a 99 cent game thinking
like I'm not gonna you know here I just paid two grand for soft business software wearing
my business owner hat and now I'm at night in bed wearing my consumer hat and I'm like
who's gonna pay a dollar for this right and but you see this a lot you see you know people
who find the quote unquote sexy business that's like the next social network or the next this
or the next that and and they really do struggle I mean some of them do well you know you see
the unicorns that just take off and even if they don't ever make any money they get aqua
hired and they're happy but it's just yeah you're right it's it's so much easier to go
after and say like businesses pay for things if they can either make more money or lose
less money ultimately you know becoming more profitable so if you can help them generate
more sales generate more leads generate something like that that businesses want that's great
and likewise if you can help streamline internal operations make it so they don't need to be
passing the emailing the excel file back and forth around the office all day which is what
a lot of companies still do yeah I mean there's there's a ton of opportunity in the B2B space
but yeah you're right it's not as sexy but it's it's one of those things where you can
multiply by existing revenue or something existing and demonstrate you know an increase
yeah I think you just have to redefine the meaning of sexy from appealing to people in
a way that that's fun and interesting to having a business that succeeds and makes you lots
of money sexy then the targeting businesses is very sexy right I think going back to your
point about how you were you were able to actually reach out to customers and find clients
by doing these kind of real life webinars across all of your businesses really you've
had amazing customer acquisition strategies for double your freelancing for example you
put out a staggering amount of content that's really high quality and you also have this
whole personalization piece where pretty much anybody from any walk of life can go to your
website and whether they're a designer or developer or some other sort of freelancer
they get funneled to just the right advice for them right or whether they're an individual
or running an agency they get funneled to you know the perfect content for them which
is something I'm jealous of because indie hackers does do a terrible job at this I just
put it all on the front page and say all right go for it hope you find what you're looking
for can you talk a little bit about how you think about content and what you've learned
about content marketing and actually being able to you know attract customers and readers
and write things that people find appealing and distribute it online yeah big can of worms
um so yeah that's a lot with yeah I mean so there's a few things right there's the let's
talk about free content so let's talk about just blog articles or you know stuff that's
on your site freely available there's no email opt-in or anything like that my my basic strategy
is a series of upsells so if somebody is reading an article of mine on my site I'm asking for
their attention right like so that's the the purchase price is however many minutes of
their time and I have a lot of that partly to appeal to Google because I get a lot of
organic traffic these days where I've really put a lot of effort into thinking like what
conversations are people having currently with Google and how can I intercept them so
like very few people are going into Google typing in like pricing course or or something
like that but they are typing in like frustrations about working with clients or about getting
underpaid or about like you know never having enough money or something like that and what
that's allowed me to do is realize that what they really need is they're thinking that
if they charge more their cash flow issues will go away like that's really the it's not
about for everyone it's not about having a better standard of life or about buying an
amazing car or boat or something like that for a lot of people it's just about getting
away from the ups and downs of running a freelancing business so I would I did a lot of work keyword
research and stuff into coming up with content that is evergreen meaning it's not the benefit
of working and helping people with consulting is sales marketing tactics pricing tactics
I mean they don't really change day to day they're pretty perennial so I you know I've
created a lot of this kind of acquisition content these this content where I'm asking
for attention and then what I've been doing a lot of recently is personalized called actions
depending on a lot of different factors so wherever you come from what articles are you
reading and so on so if somebody's reading a lot on proposals it's pretty safe to say
like that's what they're struggling with right now is closing proposals so the call to action
that they see will be focused on closing more proposals and then I get people into a an
email course that helps address that specifically now in a way I'm upselling you know they just
read a bunch of content or one piece of content and I'm now upselling a free email course where
I'm asking now for both more attention and in this case an email address so contact information
and that's now now they've been upsold effectively the email course so they go through that I
do a lot of personalization again where at the point of opting in I ask them what kind of work
they do so now I know that they care about proposal closing more proposals they're a web
designer and I also ask throughout the course I have these worksheets where I ask them other
questions like how long have you been freelancing what is your goal like what do you need to get
from this course and I take all these factors and I start to slowly change the downstream content
to be based off of that so by the time they get to basically what I do is I look at I wait for them
to hit a certain threshold of engagement where once I know that they are hitting all the right
factors that show like they're really serious about what the free email course is helping with
which is pricing theory now it's time to present to them my premium course on pricing that gives
them all the notes more turnkey gets them all the templates and stuff that they need to to get
started with this then they get a personalized automated pitch that compounds everything I know
about them so far tweaks all the the pitch copy and the sales page copy so if you go to the sales
page you know and I know you're a designer who helped once help with the proposals you know
you've been your solo let's say or you run an agency let's say all the copy will be about
design agencies and it will be about how the product will help you close more proposals because
ultimately at the end of the day people want products built just for them that's why talk
people talk about niching and like you know you gotta go deep with it on a niche or something
like that and all I've done is I made the niche the funnel I made the niche the marketing the
copy and everything else and I've kept a pretty much general product right so the product can
help writers it can help designers can help developers can help all these different types
of people who have different reasons for wanting the product but I've niched down the funnel and
that's just it's worked brilliantly in terms of ROI it's just been like in terms of lines
of code written for payoff it's probably like the most valuable code I've ever written it's
funny because what you're talking about like niching is is one of the perennial challenges
that I see people going through where on one hand it's really good advice to pick a niche
if you pick a niche that you understand your customers a lot better because they're more
similar to each other and they have specific problems that you can then identify and solve
versus going super broad then okay it's like how do you even write your marketing copy right how
do you make it appealing when you're trying to appeal to all these different people who don't
necessarily have the exact same problems and you know a good example would be somebody creating a
task management app and saying this is a task manager for everyone which really means it's for
no one right because it doesn't who's gonna use that right that doesn't solve any specific problems
versus saying okay you know this is a task manager for developers that's gonna help you keep your
code base clean or something where okay well now you're solving this very valuable problem for a
specific group of people you know where they hang out etc and your solution is I mean I guess it's
the same for freelancers too right you can say hey I'm a you know developer which sounds great
because you can solve anyone's problem which is very different than saying like hey I'm like a user
interface a user experience expert is gonna help your company improve your user experience and
convert more you know leads or convert more visitors into paying customers where what you
do is a lot more limited but now it's so much more specific that companies can actually understand
how you're gonna help them grow their bottom line and then what you've done with double your
freelancing is kind of the best of both worlds where rather than just going super deep you've
kept it broad but then inside your website you just attacked all these small niches by
by personalization and and allowing your website itself to kind of like evolve and flow and change
based on the individual profile of the visitor I mean you know to be honest it came from when
I was running plan scope and I had onboarding I asked the same questions like are you solo or
agency or I knew this based on the plan they chose and then I also asked them what kind of
work they did you'd go into the app you sign up for a trial of the app and then you would get you
know the onboarding would be tailored to you you'd get like demo projects about design if you were
designer you get demo projects about you know for development projects you for if you were a developer
but that makes sense because that's a web app right like you log in you sign in and then this
is your data likewise you go on Facebook you know I'm not gonna see your friends I'm gonna see my
friends because it's it's scope to me it's scope to my user account so I thought well what if wait
what if I took the same concept of like what if I traded an opt-in or an email click you know click
from like an automation email back to my site as an authentication event because you can include in
that payload like the new the you know basically the subscriber ready of the new opt-in or if it's
prefrontal if they haven't opted in yet what if I just use local storage or cookies even to track a
lot of this stuff and then what if I could also treat like my email marketing app as a data store
and record like what they're reading and what kind of content they're engaging with and so on what
they bought and then finally what if I could just do the stuff I did my rails app but on my WordPress
blog like what why not like it's just if then statements right yeah I mean that's basically
all I've done is I've just treated my blog my marketing site as a sass I report on it the same
way I did with plant scope I you know have a lot of this on the fly customization that you know
it's a kind of a lot of us assume our website our content is static but it doesn't need to be because
at the end of the day like you know I mean it's it's funny when I started getting into WordPress
for the first time and I do all this stuff with like custom call to actions and stuff
people would write in saying like what plugin are you using and I like well it's just some
JavaScript and CSS and HTML like it's not I don't know it's not a plugin it's just you know the end
of the day WordPress is serving up HTML to the browser so you know I mean it's just it's that
realization that I can do that kind of stuff on what's historically been seen as a static thing
a thing that needs to appeal to everyone and speak to everyone well why can't we just do what we do
in our in our software in our web app stuff and do that on our sites on our marketing sites on our
our blogs or whatever else we've just gotten used to content being the static thing and
I wonder you know in the future like five ten years from now if everybody's going to be doing
this you know every single piece of content will be personalized based on kind of a profile that
people have and I would love to talk more about that but some people from Twitter have asked some
very interesting questions and I would fear miss not to actually ask you those questions
before we run out of time here one of the biggest things that
nd hackers readers want to know and that people who really want to get into starting
businesses want to know is how they can get started as a contractor and the reason I think
that's important to people is because if you want to start your own online business
you need time to do that and it's very difficult to find that time when you're working a full-time
job nine to five forty hours a week every week versus if you can be a freelancer which is what
I was doing before I started nd hackers you're a little bit more flexible with your schedule
and you can maybe work two or three days a week you know or you can work
on weekends and then it's been the week building your project so let's say I'm an entrepreneur
in this position I want to quit my full-time job and I want to do some contracting to support
myself as I start a product business and I'm a developer what route would you recommend for me
to get into that yeah I mean the first thing I would do if you don't have a lot of availability
during the day because you're full-time salaried is I would really the best thing you can do early
on is to just build your network I mean it sounds trite and overused but it's true just going out
and letting people know what you do and how you can help I mean because again like what you if
you don't have a client base you don't have any potential referral sources yet so if you can do
things like one thing I really love the concept of is like going to existing events like networking
events or any of these kind of things that happen in any decently sized city virtually almost every
night going to one of these events getting to know people doing a lot of listening and really
getting to hear like hear people out what are they ask them questions about their business and
ideally how it intersects with kind of what you do so if you're a developer I'd ask people about
like what kind of so tell me about like technically what kind of technology do you have in place at
your company get them to talk get them to tell you a bit about kind of behind the scenes stuff
and ask them questions about like so what you know what kind of sucks about the way things are
I mean this is a lot of this stuff I did early on locally where I realized like a lot of people
were really struggling with excel I didn't even know like people really used it on a like people
can go crazy with with spreadsheets and I didn't know that because I never really have used
spreadsheets so you know I learned that I listened to what they were saying I built up this network
and I was able to do a lot of follow-up and just say hey you know I was thinking about what you said
have you thought about doing this this or this so you know spend the time to build up your network
give people find ways of delivering value I mean this is going to be value you're delivering
individually through a conversation but it's a start I mean ideally you want to eventually get
to more scalable ways like you do a seminar or an online thing or you have more evergreen things
like content you push on your site your new consulting site you know stuff that is always
kind of there working on your behalf but I mean that's one way the other big thing is I mean
you're you've got your time limited probably because you probably don't want to be working
on it and then drumming up work all night honestly for a lot of new people I would say like look for
people who probably already have existing projects right who are have already gone down that funnel
and have realized they have a problem it can be solved and they can be solved by hiring a developer
go after that you're not going to get the kind of value pricing that you want early on but could be
enough to initially support you so you can jump make the jump and quit that you know your job and
do this full time I'd also ask you know your current employer when you decide to quit I mean
you've got a lot of domain knowledge most likely and you know their setup you know their infrastructure
there's probably a good chance especially if they're going to need to go and find somebody
like you and go through the whole recruiting process and onboarding if you can just stick
around for a few months and you know now they're effectively your first client I mean that's the
kind of stuff I would do if I was full-time salaried at the moment and wanted to start my
own business start there and then progressively kind of build it do more of a focus on building
up your audience and stuff what I would also do is if you do plan on building a product like a
you know a software company I have the audience of that business can be similar to
what you're doing on a consulting basis that's even better so if you want to eventually start
like an A-B testing company do A-B testing consulting do some sort of optimization stuff
like that so that you're not you're you're gonna learn a ton you're gonna learn a lot about this
audience their needs how they describe stuff and everything else but you can eventually
set up like productized offerings that you sell to this audience and then slowly swap them out with
software you could slowly build so I have a friend who does metrics analytics so he
looks at companies and looks at kind of metrics deficiencies and so on
and helps him improve like organic traffic I mean it's a it's a broad thing he does but he built
this SaaS called metrics watch that is now he's getting consulting clients through that because
people come to that SaaS wanting you know it's just metrics analytics so you know it'll basically
look at your metrics and contact you when like hey you're getting a spike in referral traffic
so people come in through that but then he's within the app he's able to actually upsell his
consulting by saying hey you're you're getting a lot more this is your current you know organic
traffic over the last week would you like to look into figuring out how you could get even more
organic traffic if so click here and then it goes through this whole contact process and for those
who come to him directly for consulting if they don't qualify he can then down sell them on the
SaaS so it's much better than going after audience one and then having a building a SaaS that you're
starting over from scratch with the new audience ideally if you can have the two be over overlapping
that that's a good thing yeah i think this dichotomy between selling or basically targeting
people to solve a specific problem versus a very general problem is important because
it's important to learn how to do as well because as a developer working in a company who wants to
get into consulting let's say i go to one of these events and i start talking to people well the way
that i'm going to know how to sell my skills right now is it's probably just a ruby developer or as
a javascript developer or front end developer and i can say hey you know do you need anything coded
i can code that for you i might not know how to do the value-based selling yet where i could tell you
or i could identify a specific set of problems that are shared between different people and then
pitch myself as the person who can help you get off of using excel spreadsheets etc where i can
sell for more and you know develop my own personal brand so how do people learn what they're good at
and what value they can provide and what the market actually needs i mean i would look at
first off do you have any sort of unfair advantages to have you worked in a business for instance that
gave you a lot of insights into the you know oil natural gas industry um have you do have you done
a lot with maybe to go back to ab testing maybe you your developer who knows a lot about ab testing
because you've had to do that in your day job or it's a hobby of yours i mean these are the kind of
things that can make you pretty unique in in the market but ultimately i mean my big thing is
i'm very reticent about encouraging people to go and say like plant their flag as a
web developer for hire because at that point again you're only going to appeal to people who
know they need a web developer which is a limited subset of people on top of that the people you do
get will generally be price shopping you against other web developers and what's going to happen
when you're wanting to charge 100 an hour because that's what you need to stay afloat in the bay
area and they come back to you and say well you know there's this guy i found on Upwork in Pakistan
who's eight dollars an hour why should i pay you and it's that's a really hard argument to and
that's a really hard question to answer right so you know that's why i'm big on like just get away
from the stuff that happens inside the factory altogether just focus on like what problems can
i solve i mean it doesn't take as long as you are pointed in the direction of knowing that people
are not wanting to pay you gobs money for code but instead there's something else at play
just doing the due diligence to figure out exactly what it is that they really need and then
using code to solve that i mean if you do that you're going to be better off than like 90 percent
of the competitors out there right because everyone else is so focused on the tech and if
you can say how can i leverage this tech to achieve a certain business end and what is
that business end and what does it mean i'm forget about the whole like value pricing everything
value pricing everything else i mean you can and you should do that but starting out i would just
say like you can increase your levels of success by just focusing on like basically removing the
risk of hiring you so if i hire a web developer they can technically succeed but they can still
fail in terms of delivering what i need and that's something a lot of us really don't internalize
that well is that we can technically build a functioning web app that is by all mean the by
all indications complete and well built and everything else but it could completely fail
to achieve the business ends that they need and the more we can do to focus on what is it they
really need and where are they now and how can we help them get from here to there and what does
that mean scope wise what does that mean in terms of what we're going to be building that's what we
should be focusing on because you do that and you're going to be much lower risk and you're going to
honestly have an easier time selling people you're going to come in as a partner as an ally from day
one instead of just a hired gun and you're going to go you know it's going to be a better project
overall because you're going to be delivering ultimately a better product if you stay focused
on that outcome yeah i like the way that you put that that you can be a web developer if they're
hiring you as a web developer you can succeed at being a developer and yet fail at accomplishing
their actual business objectives and so if you pitch yourself as someone who comes in to hire
to you know directly target those business objectives then it's a lot easier to you do
risk yourself right you're someone who they can look at and say okay this person's actually here
to solve the actual problem that i want which is getting more customers or converting more leads
etc rather than just writing code and then hoping that that code eventually you know it's easy
objectives the last thing that i want to ask you about is what is the next step after that is it
important for someone who wants to be a freelancer or consultant to develop a personal brand and
create a website and a blog and start producing content or is it more important for them to
continue just going to events and talking to people how do they move to the next level
i mean events don't really scale that well if you tend to have a very i mean what i would do is i
would optimize to have recurring revenue that is you know these kind of retainers that are more
value-based where they're not retainers of time you know it's like for instance my friend nick
who runs draft revised he does monthly ab testing as a service there's no indication of how many
hours he puts in each month it's just he gets like 15 people paying him a few thousand a month
and that's his revenue and if one drops great it's not that big of a deal he just needs to find
a replacement but it's not the likelihood that all 15 will will cancel and one month is relatively
low and he's not all that hamster will need to go and find you know customers or anything else he
just he has his mrr at like multi-thousand dollar chunks at a time right um so i would optimize for
that i would also over time i would look at ways to a lot of the sales processes overcoming
objections and educating people about like why does they might need really need to hire somebody
like you so if you can delegate a lot of that uh educational stuff to automation uh that's all
the better so maybe go on podcast your guest post create your own content and then lead people into
a funnel that ultimately ends with a sales call that's good too and the last thing that i would
focus on would be i call it road mapping but it just it's paid discovery which is before trying
to get somebody on like a you know tens of thousands of dollars engagement uh have something
that's less pricey that's you know fixed scope fixed price that you could sell first that could
be kind of like a you know what i do so you know for instance i do a lot of big automation stuff
when i do consulting work but before doing that sony needs to pay me six thousand dollars to put
together a road map where i'm digging into their business their existing you know customer
evaluations how they get clients now and so on and i put together a personalized plan of action for
them as a report and i i do all this for them up front and it's a way of kind of qualifying people
who can then pay 10x or more of that to hire me outright for a consulting gig so it allows them
to go from in my case zero to six thousand before needing to go from zero to a hundred thousand
which is a much safer jump it's kind of like a you know it's it's i'm basically just selling them
something cheaper first before the trust is really established and i've seen that in my
own business i have a nine thousand dollar course that i can drive all the paid anonymous traffic to
that i want and it would get no sales but the people who buy that have gone through the
three hundred dollar course derived a ton of value from that and then are now moving on to
this more immersive more high touch course um as a result of having experience that win as a result
of working with me so it's the same kind of thing how can you give something i mean i've seen people
do two three hundred dollar road mapping sessions where it's an hour skype call where they dig into
their business they look at what's possible and so on and they treat that as a separate
preliminary engagement that needs to happen first and then from there the deliverables really the
proposal so the client gets this deliverable which is really a proposal and they're looking
at it as a report instead of a pitch and then they're basically upsold the implementation
engagement uh from that initial road mapping engagement so that's the third thing that i would
do so yeah i mean there's just a lot and there's a lot of parallels with that in products right
like you know obviously optimized for subscription revenue find ways to systematically generate
qualifying then convert leads and finally if you're going to do if you've got some sort of
you know product business especially find ways of having a kind of like a stepladder approach where
people start off maybe small in the internet marketing world they might call it like a trip
wire product and then deliver value from that and then basically upsell them on the bigger
more immersive more expensive uh you know products i wish i could say that this is a good place to
end but man there's so much i want to talk about and unfortunately you're out of time
i think you know you've got such an incredible breadth of experience across you know you're
running your agency and doing product businesses and and basically being an educator online and i
think i would love to have you back on the show at some point in time because i feel like you
could talk for an at just like an hour about automation an hour about content marketing and
an hour about uh you know engaging customers and doing sales and all these different topics so if
you're up for it sometime in the future we'll have to have you back on the show i'd love to yeah
anyway can you talk uh tell people where they can go to find you
and find more about what you've written online yeah so my main website is double your freelancing
dot com uh that's where you can go and see a lot of what i talked about if you want to dive deeper
into or you just want to see an example of a personalized automation sequence you can go to
free print free pricing course dot com and that just redirects to a landing page on double your
freelancing but that's that's kind of like my main entry point for a lot of people and if you're
interested on the personalization side of things i'd encourage you to check out write message
r-i-g-h-t message dot i-o um or you can also go to brennan dot com which is my personal consulting
site if you're into that kind of stuff all right thanks so much for coming on the show Ben and i'll
see you later yeah thanks korland if you enjoyed listening to this conversation you should join me
and a whole bunch of other nd hackers and entrepreneurs on the nd hackers dot com forum
where we talk about things like how to come up with a good idea and how to find your first paying
customers also if you're working on a business or a product of your own it's a great place to
come and get feedback from the community on what you're working on again that's
www dot nd hackers dot com slash forum thanks and i'll see you guys next time