Ep.30: Freelancer To Founder While Putting Family First with Preston Lee


Today, I'm really excited to share a conversation I had with Preston Lee.

He is the founder of, where he and his team have been helping freelancers grow their solo business for over a decade. And he's a freelancing parent. 

He has built businesses. He works from home. He balances work and family life. He doesn't work 40 hours a week, just like me. And he also co-hosts the Freelancer to Founder podcast, all about how to scale up their service-based business beyond just themselves so that they can have exponentially increasing income. 

His advice has been featured by Entrepreneur, Inc, Forbes, Adobe, and lots more. He's a dad to three kids and he loves to cook and play Legos. So do I, a lot of his story really mimics some of mine. He's going to share his story with you today on how he got started with freelancing and turned it into his full-time career. And now he's helping freelancers. He's coaching freelancers and providing freelancers a way that they can find success as well.



Thanks so much for having me. I really appreciate it.



I'm excited to talk to you today about what it's like to be a freelancing parent. A lot of our audience are freelancing parents and they're trying to navigate the transition from being an employee to freelancing, or maybe they've just got married. They're starting a new family. They haven't had a lot of career experience yet, but they are considering freelancing but a lot of the momentum, a lot of the pressure, is pushing them towards the traditional route of building up their career. I'd love to know a little bit about your story and introduce you. Introduce yourself to us and tell us a little bit about what were some of the turning points for you. Just summarize what your career has been like getting to where you are now, where you've been involved in different businesses and you're doing that thing.



Yeah, sure. So let's start with where I am now, and then I'll tell you how I got there. So I currently run a website called millo, and it's at and we help freelancers. Our whole mission is just to help freelancers, grow their business, be more satisfied in their business, be more fulfilled in their work and find more flexibility in their life and work. And it's a blast. We have a small team of people. We produce a podcast called Freelance to Founder. We have the blog obviously, that we publish multiple times a week and then we have lots of other things as well. All of this took a long time to build because I built it mostly on the side. So if we rewind boy, uh, 11 years, maybe now 12 years, I was a student at university and I was freelancing, putting my wife and myself through our last year of college.

So as a freelancer, I was doing some web design, some graphic design, and really that was how I was paying for our last year of college that we had together. 

During that time, I was also, as an experiment, as a student, I was just blogging. I was kind of learning about the whole blogging space and how it all worked. And I was blogging about my experience as a freelancer. Over the years I started noticing people really were enjoying like the, how to's and the in-depth look at what it takes to really make your freelance business succeed. So I started publishing more and more of that and found other people interested in that. We started publishing a lot of that kind of content as I continued to freelance, I continued to grow this thing, but I also got a full-time job, out of college.

So I was moonlighting. I was side hustling. You asked about turning points. There was a turning point where I got a job that I had to commute on a train about 40 minutes, one way each day. So it was about an hour and a half give or take. I just like worked on the business, between work and home.

So I'm very, very devoted to my family. They come first ahead of my business and ahead of everything else. I would work all day and then I would side hustle for 40 minutes, then I would come home and it was all dad and husband time. 

And so I did that for a lot of years, changed jobs a few times, got some promotions, some raises, I was making pretty decent money. Then I was working at a tech startup and they ran out of funding, lost a couple of big clients and let about half the company go. 

So, at that time I talked to my wife and we decided I was going give it a shot to go full-time with my solo business. That's what I've been doing the last few years. I have a small team. That's awesome. And we, like I said, we just serve freelancers. I still do some freelancing myself. My team is all made up of freelancers, contractors, so they do their own freelance work on the side. And then we partner with other experts who have grown massive freelance businesses to share just what we've learned along the way with other freelancers who may be getting started, or may be trying to figure it out.



Wow. Well hearing you talk it's, it's almost like hearing my own story and it was just really weird experiences after I graduated college. I commuted 40 minutes on a train to a full-time job. I ended up getting let go from that full-time job because they downsized and to cut half of the employees. I mean, it literally is like a lot of the same points.

I was freelancing on the side and eventually decided to transition when I realized that, "Hey, I just got let go and I can't, this employee thing is not as secure as I thought it was." 

It's great to know that there are others out there that have very similar stories. With you prioritizing your family throughout this whole thing it's easy to give into the temptation to say, wait, this is all for them, I'm going to just push them aside for a couple of years. I'm going to work 80 hours a week and by then my kids are grown up. It's very easy to fall into that trap.

And it seems like you've always kept your priorities straight in what is most important to you. That's definitely something to be, to be admired. Do you feel like there was a lot of pressure throughout that transition to maybe drop those priorities? Was it difficult at times of, "Hey, I'm not earning enough money, but I've got family needs." How did you play that tug of war?



Yeah, I mean, I'm certainly not perfect at it. I, you know, certainly sometimes I still prioritize work over family in small moments, but like in the grand grand scheme of things, in the grand picture, I always try to prioritize my family over my work. I think I could be making a lot more, in my business if I worked longer hours, you know. I've heard on your show, you talk about working, I don't remember, you said like 25 hours a week or something. That's about what I'm doing too, is like maybe 25 or 30 hours a week and it's great.

I could work 40, 50, 60 hours a week and probably make a lot more money. And so, you know, I think that's always the balance. It's like, yeah, I could make more money, but for what? For me, it's just always been like, it's just always been about how do I balance the time I spend at work, with the time I spend with my family.

I remember when I was younger, I read an obituary about Charles Schultz, the guy who created Charlie Brown and the Peanuts. In short, his daughter basically said, like, we never knew our dad had a job. 

And I just, I read that like, when I was like 15 or something, I just remember falling in love with that idea that he was so around, he was so available that his kids had no idea that even really had a job. It's kind of fun because now my kids, every once in a while, will say like that I don't have a job or they'll say like, "well, if dad got a job," or something, and they don't realize that even though I'm, you know, working a lot throughout the day, they can come down to our basement where my office is. They could say hi, anytime they want, like, I often pause to play or watch a TV show or something. So it's just fun to find that balance. It's not always perfect. Sometimes I just have to say, guys, I got to work or guys, I have a call right now. Right? And it just has to happen but it's fun to try to find that balance, for sure.



Yeah, it is. And it's an ongoing pursuit to find that balance because yeah, there are moments where I have to. 

I have a five-year-old son, I have a two year old and my wife's pregnant with our third. And it's, uh, there are times when I have to, especially the five-year-old,where I've got to tell him, "Ok I'm focusing on this. I am working for the next hour and I can't break away." And there are times when I'm a little more flexible and I can break away. 

What I do is I have a certain amount of hours that I really commit to every week, unless I'm specifically taking time off. Because I know if I put in those amount of hours, it's going to result in me producing the continued results that I need to produce. But I'm, you know, somewhat flexible on schedule, but I've noticed that when I stick to a consistent schedule, it's much easier on my family.

My son, who doesn't quite know how to tell time yet, it's amazing how, when four o'clock hits, which is usually when I end my work day, he just knows that, okay, ready to play it's time. Even though he doesn't know how to tell time. It really helps the family in that way. 

I like how you brought up how it is this, you know, it's not always pretty, and it's not always just easy going. And sometimes you have to keep telling your kids over and over again why you're doing what you're doing, and they don't fully understand the economics of it. I do admire that you're really trying to make that balance work. It's something that I've always wanted to do since being a kid.

My dad, he was there, he had a normal job, but he was there, as a normal dad is on the weekends evenings. But I knew that he wanted to be there even more.



I think, you know, my dad was the same way. He's a fantastic father. I think he would have liked to be around more. And I think what happens sometimes-I don't know that this happened with my dad necessarily, but I see it all the time. I think it happens to all of us to an extent, and that is you start out saying, "I'm going to work for my family." 

Like you mentioned earlier in the show, right? You start going to work, thinking like, "this is for my family, this is for our, you know, our livelihood. This is for our home." Like I have to pay for our home. I have to pay for groceries. Like, there's all these things, and it's my job. Often as men, we feel like it's our job.

Of course it's shared between whoever decides to take on that responsibility. At least in our family, I was kind of raised that it's the man's job to take care of the family and provide for the family, make sure that we're set. Right? Particularly financially. So you start off that way, but then after a while, it's like, oh man, promotions at work are so alluring and making more money or getting the praise at work, all these things start to mix themselves in. And if you're not careful, then you don't realize that you start working more for you than you're working for your family.

Then after a while, like you said, before you know it your kids are grown up, you've been working all this time and it's kind of like retirement. You just, you work and work and work and work so that at 65, you can have some freedom. When in reality, you've worked your whole life instead of finding, yeah. And you are 65. It's a lot harder to, you know, travel and take on new hobbies and try new things. So there's a lot of freedom of flexibility that comes from working for yourself, or even building a side hustle freelancing.



So what do you believe are some of the benefits of freelancing?

Why is freelancing one of the best ways to achieve that type of balance?

 Because as far as I've seen, I know that there are some companies around the world that are experimenting with 30 hour work weeks, 25 hour work weeks where they're paying them the same salary, but having them work less. I know that friends, I have family who have typical employee jobs. I mean, they'll admit that out of the 40 hours they work, there's at least 10 of those that are not productive, that you really can accomplish more in less time. And I know you had mentioned, Hey, if I worked 40, 50 hours a week, I could earn a lot more money. I've had so many moments where I'm like, oh, we could move through these financial goals we have even faster if I worked 40 to 50 hours a week. 

Then I have the second thought of maybe not, that if I didn't have the balance that I have, if I'm not meeting my family's needs, outside of the financial side, I feel as if that would cause me a lot of underlying stress that might actually affect my success. That maybe I would work 40, 50 hours a week but I'm not actually earning anymore. That, you know, if I crunch some numbers, I would totally be earning more, but then I don't know. I do want you to talk,



There's a point of diminishing returns, most definitely. Right?



Yeah, but I'd love you to talk a little bit about just those that are considering. Just imagine that somebody's tossing around the idea of freelancing and they've heard, you know, pros and cons and they want the type of life where they can work 25, 30 hours a week. They can have more time with their family, but is it worth it to pursue freelancing to have that? And is that one of the only ways at this point, at least in today's uh, the way that we work that is most common.



Yeah. Yeah. Those are good questions. So, uh, like I said, I've been in the freelancing space for, I mean, I've been a freelancer myself for 12 years plus.

Then, you know, been helping and coaching freelancers for another decade or so. I've begun to see freelancing, like solo freelancing- just you not working with anybody else- as a bit of a stepping stone. 

Lots of people make it work as the only thing that they do. Right? I use freelancing kind of as an umbrella term for working for yourself and being your own boss.

I think freelancing for sure is the quickest way to escape, you know, corporate life because everybody has skills that they can potentially monetize, right?

Whatever you're good at at your day job, you could potentially quit today and find people who want to pay you for that on a freelance, or client basis, and get paid to do that work.

Now, your job changes dramatically from just doing that thing all day to doing that thing part of the day, and also finding clients, sending invoices, getting paid, running a business. Right? So that changes, but it's much quicker to, I guess, get out of the rat race as you might put it, and start freelancing than it would be to build a tech startup or something. Or become an influencer or some of these other options that you hear about, like, they take a lot of time. Whereas freelancing, you could potentially within a month or two, have a nice book of business, and start bringing in revenue right away. 

So I think that's one reason that I lean toward freelancing as a way to either build side revenue or eventually transition to full-time revenue.

However, like on Freelance to Founder podcast, we talk to freelancers about scaling. About getting past just you and just trading hours for dollars, because the only way to make more money as a freelancer, if you just charge by the hour, the only way to make more money is to work more hours, right? You can raise your rates, but only to a point, and then people stop hiring you. Then you can raise your hours, but only to a point, and then you burn out or you don't have any time for family, which obviously that's the whole point of this show. 

So it's like, well, what are the other options? 

  • On Freelance to Founder we explore those options in terms of like, can I hire someone? 
  • Can I hire subcontractors? 
  • Can I offer recurring revenue services where I know exactly what I'm going to make month after month after month for the next 24 months so that I can then make some of those business growing decisions.

 I think for me, the power really lies in like taking freelancing to the next level, where you're offering yourself in services. You're still working with clients, but you're really building more of a business, you're becoming more of a founder as opposed to just trading your time for money.



I'm really glad you brought that up. That's exactly the transition I'm in now. So I hit a point about a year and a half ago where I was like, okay, either I'm going to, I did a lot of consulting on video strategy and YouTube channels and various things for businesses. Video marketing has always been my freelance business.

I started out as a video editor. When I got to a point where I realized, okay, well doing this consulting, and in providing these services, I'm going to have to increase my hours to earn more money. I've increased my rate over a period of time as I got more and more experienced, but then it hits a cap where people are only willing to spend so much on a certain service and even, you know, doing different flat rate projects and various things but it got to a point where I realized I needed to start hiring people. 

And just like you I've hired freelancers. I don't have any employees. I love supporting freelancers. So I have a small team of a few freelancers that I was able to start offloading things to. One is just an assistant that helps with random business stuff, and then a writer, video editor. And I'm in the process of trying to build up that team. 

I'm right in that transition of turning into more of an agency. Which is why I love your show, that you're focusing on that, that scaling part, where, yeah, you're still in the kind of industry. You're not starting, like you said, you're not starting some tech startup. You're not trying to go and find a bunch of investors. You didn't invent some product, it's just, it's a service, but you're scaling your service by getting help. It really does, it really does help you to continue to increase that income and scale that way. You have to have that goal in mind. Unless, like you said, some people are okay to just solopreneur it for the rest of their life, but it is limited.



Yeah and I think particularly when you talk about like being a parent, you know, that can grow obviously, right? Like you have, you're expecting another child here soon. Anyone with a kid, or more than one kid, knows that those expenses grow, right? And so your expenses grow and your time actually goes down. So your available work time, I should say, actually goes down. 

And so if you're only charging, if you're only trading your hours for money, then that becomes a real problem. When if you want to grow a family as well, because with each kid, you seem to have a little less time to work. Then, you know, you seem to have a little bit more expense. It's the best, best possible thing that has ever happened to me is having a family, but the reality of it, the economy of it is, that. I have less time to work and I have more expenses. 

And so I have to find a way to now scale my business. Where I could maybe be a solo freelancer and support my wife and one kid, another kid comes along and maybe I'm going like, "Okay? How am I going to now support a family of four? I'm just trading my hours for money." And sometimes the math doesn't necessarily work. So that scaling piece is really important in terms of being a freelancing parent as well.



Definitely. Well, anyone listening, I encourage you to go and check out his podcast to learn more about how to do that scaling process. I wanted to ask you a little bit about what are some first initial steps that somebody ought to take? That they've never had a client before, they have some idea of what they could do as a freelancer. Maybe they've been doing some copywriting for a local business as an employee, and now they're thinking of freelancing. What are some of those first steps to take before they quit their job, to even know when to quit their job? That way they can get the process started leading towards their first client or two.



Yeah, for sure. So, I waited too long to start my thing full time. I needed that push, sometimes some people need a push by getting laid off or whatever.

I have a friend who got laid off like three times, and then he was kind of like, you know what, it was like three times in a few years and none of it, his fault. None of it performance-based, but it was just the companies didn't work out or whatever. And he was like, "You know what, I'm just going to do my own thing. Like, it just, I can't deal with the volatility of a job." 

I would say like, if you're working a job and you're ready to start freelancing, for me, like it's all about the runway. So I maybe had too much runway. 

When I say runway, I mean like how much money do you have in the bank to keep your current lifestyle going?

Unless you're doing it on the side, the day you quit, you're not going to have a book of clients that you can just turn to and start charging.

Right? So there's going to be a gap probably where you're spending a little bit of your savings. Uh, and until you can build up your revenue a little bit more, and you're making maybe what you were doing in your day job. 

That's also true if you've been side hustling, because what I saw was that we were making basically two incomes, because I had my side hustle money and then I had my day job money. And so I lost the day job, had the side hustle go full time, but there was a period between where we were making less actually overall, right?

This runway idea is really important. We had like 18 months or something. It was way too much. I would suggest for anyone listening, like a good six month buffer is nice. 

So you have six months to kind of get your business off the ground, accounts for any emergencies along the way or unforeseen expenses along the way. So maybe a nice six month buffer, you know, if it costs your family 5,000 bucks to live month to month then you want to have $30,000 in the bank. What often happens is you quit your job, you start freelancing, and then you're like, "Wow, this is a lot harder to make money than I thought from scratch." And so then you just go back and get another job, and you're just back into the cycle. Instead, you have to give yourself some space and some time to make sure that that can actually work out.



Definitely. That's absolutely true. In my case, I definitely had a gap because I started doing some freelancing before I actually lost my job. Then when I lost the job, I definitely wasn't ready yet to replace my income. So there was, in my case, I was not prepared. I got into loads of debt just to live. And I didn't want to just go and find another job. I had already determined that it just wasn't the type of work situation that would work for me.

I spent the first year after I started getting clients and earning money, paying off that debt first, it's not like I could go get a bigger place to live or put money in savings. That runway concept is super important.

Where do you find work as a freelancer?

Obviously what you're involved in helps with that too as you can certainly talk about that as well. Where do you find clients in 2021?



Yeah. That's, that's the big question, right? In fact, that's the number one thing we get asked by our community. We, you know, have hundreds of thousands of people read the blog every month. And always when we do any sort of outreach with email or social posts or anything like that, we always hear back like the number one issue I'm facing is I don't know how to find good clients or any clients at all. 

We started a service called Solid Gigs where our team rounds up some of the best freelance jobs on the internet and then sends you the ones that match your criteria. So like if you're a writer and you want to work, you know, part-time or do part-time freelance work for big companies or whatever, there's all these criteria you can set and we'll send you the best ones.

However, this isn't a pitch necessarily for our product. There are lots of ways you can find your first clients or new clients, if you need to. For me, you know, we've talked to freelancers who work exclusively on sites like Upwork or sites like Fiverr, you know, there's a huge marketplace there. 

Sometimes those get a bad rep and it definitely depends on the industry. You know, I feel like maybe graphic designers can get a little slighted on some of those sometimes. It depends on what industry you're working in but sometimes those marketplaces can be a great way to just get revenue in the door quickly because they already have millions of companies looking for freelancers who have skills that you might have. 

Now, if you're not into the marketplaces like Fiverr or Upwork and you're not into a lead generation service like Solid Gigs, there are lots of ways you can find clients on your own. I do find it's a little slower going, unless you're really great at marketing. So if you're a marketer, like you already have a bunch of ideas, you don't need to listen to this section, I would imagine. But if you're not a natural marketer, if you don't know how to advertise and reach people and connect with people, book people and close a deal, I would suggest starting like joining groups where your clients might be hanging out. Facebook groups or LinkedIn groups connecting with your own personal network and saying like, "Hey, I'm doing this freelancing thing. I do graphic design," or you know, I do copywriting or whatever, "Do you know anyone that might need those services?", might need a photographer or might need whatever you do.

You'll be surprised, as you are vulnerable with people and you say like, "I'm starting to do this full-time," or, "I hope to eventually do this full-time, I'd love your support," people really will come out of the woodwork. 

You can obviously go to like community events. There's like chamber of commerce here in the US. There's Chamber of commerce in most cities where you can go and meet business owners. If you're doing like a D2D (Door to Door) thing, you can collaborate with people with other companies. 

If you're a wedding photographer, you might collaborate with wedding planners or event venues, right? To just tap into an existing flow of potential new clients. So there's lots of ways you can do it. 

The idea is to figure out where your clients are spending their time and then figure out how you can add value in that space to attract their attention. Once you have their attention and trust, then it's easy to just say, like, I'm a web designer, I'd love to help you increase your, your conversion on your website get you more customers and there'll be a win-win for both of us or something like that.



That's great. Well, thanks for that advice, Preston, that was very helpful in us knowing the different ways that we can find that first client.

 For me, I got my start on Upwork. Well, my very first client was just a local client that I found through networking, but Upwork really helped me to gain momentum. As I built a portfolio I was able to find clients elsewhere. I still have clients on Upwork and I have clients that come through LinkedIn. 

A lot of it is online networking that I've, that I've done. I went to some networking events and it was just too for me in trying to find the right people that a lot of times it was like, "Oh, I'm not looking for that." Sometimes those relationships led to somebody who was looking for something. 

Your service, I think, is really cool that essentially you're scouring all these different job posts and job sites and then compiling them together for people. So I definitely encourage anyone listening to go check out Solid Gigs. Is there anything else you wanted to share with our audience to close this up?



I got to tell you this cool story. So like I said, we often tap into like freelancing experts to share with our audience ways that they're growing their freelance business. Years and years ago, we had this contributor write a story about this client getting tactic, right?    He had to actually stop doing it because it was working so well. So maybe this is a fun gem to wrap up with. So he would go to conferences and big events where lots of his clients, potential clients, were going to be. His only purpose of going to the event was to find new clients. And he was a web designer. Uh, oh, that's a lie. I'm sorry. He was a copywriter. And so he wore like a black shirt and on the front, it just said "copywriter". There was no branding, there's no website. There was no call to action. Nothing that you might traditionally think an advertisement needs to have. It just said on the front of his shirt, what he did. Right? He went to this conference and you just, people just were approaching him and like, "Hey, I need a copywriter. I need a copywriter." He ended up getting so many clients, like I said, he had to stop wearing that shirt places. 

So fast forward a couple of years we had a reader. So his name was David, the one who submitted the original story and people loved it. People ate it up. A couple of years later, fast forward a couple of years, and a guy named Clay was reading the blog. And he was like, "that's a pretty good idea". So he started doing this in Little Rock, Arkansas.

Well, Clay took that idea and got so many clients from it that he ended up building an agency that made over a million dollars a year, has 20 plus employees. All from wearing a shirt that said web designer.

Clay is now the one that co-hosts of Freelance to Founder with me. So he shares his ideas and experiencing growing his agency. He eventually sold his share in the agency, is now growing a different business, but he grew it from zero. Well from him, I guess from one to like 22 or 24 employees, something like that. Over a million dollars a year in revenue, and recurring revenue by the way. He figured out this month to month thing that he could charge his clients and it all came from this t-shirt idea. 

So, you know, if you don't have any clients or you need to find more clients that could it to be a way to do it as COVID starts to calm down a little bit, depending on where you live in the world. You can start going to more conferences, more events wear a shirt that says what you do and be ready to pitch your services to people who seem interested.



That's a great story! Thanks for sharing that. Even just wearing that shirt as you're out and about, not even at a specific conference or something, you just never know.

 Well thanks Preston, thanks for sharing so much value with us today on how to one go from a Freelancer to a Founder, also how to balance those priorities of being a parent and having a family and pursuing this freelancing thing. You really taught us some really golden principles today. Also very good how to advice on how to get this thing going. So, thank you.



I'm glad it's been helpful. I appreciate being here.



I'm glad you got to hear this conversation today that I had with Preston. I hope that it brought a lot of value to you. I hope that as a freelancing parent, you now realize that with his testimony and my testimony and everyone else's testimony that you hear that this is possible.

You can freelance as a parent and you can earn more money than you're currently earning in your employee job. You can work less and you can spend more time with your family. You can, on one income, provide the lifestyle that you want. And you can have that work-life balance that everyone really wants and that you and your family deserve. 

If you want to learn more from Preston, go to or Solid Gigs and follow his podcast, Freelance to Founder, and definitely read his blog. We can learn a lot more about how to be a successful freelancer. So be sure to subscribe to the podcast if you haven't already. It's on Apple podcast, Stitcher, all the main ones. 

Go to to get show notes, go to YouTube if you want to watch this. If you're already on YouTube, then head over to and you can listen to the podcast. You can read the transcript.

 I will see you in our next conversation all about how to be a successful freelancing parent.

Freelancing Resources From Preston:
Freelancer to Founder Podcast:
Solid Gigs:


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