Freelance to Founder Podcast Art

Real freelancers. Real growth.

Freelance to Founder is a unique weekly podcast featuring coaching calls co-hosted by Clay and Preston, two freelancers-turned-business-builders. Instead of typical interviews, each week a new freelancer calls in to talk with Clay and Preston with one goal in mind: overcoming the feast/famine cycle and scaling their service business. The highly acclaimed, top-rated podcast is a weekly dive into what it really takes to go from freelance to founder.

In partnership: Millo, Dripify, Podglomerate

New shows every Thursday. Subscribe with your favorite.

S16 E10 — 54 min

Delegate without Sacrificing Quality

On today’s show: how can you delegate without upsetting clients or sacrificing quality? It’s a problem today’s guest Michael is facing in his young freelance business. He’s been working for himself for a while, but can’t seem to solve the delegation piece.  So, with a little role playing, ....

17 min

[SHORT] Fixing an Invoice Mistake

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. In this SHORT: Have you ever sent the wrong amount on ....

S16 E9 — 58 min

Can Your Business Run on Autopilot?

On today’s show, we chat with Carey from PodcastFastTrack.com where his business has taken off over the years. Carey is a bit further along in life than many of our guests and is contemplating retirement.  But instead of just selling his business, he wonders: can he just hire the right people to  ....

15 min

[SHORT] When To Hire a Project Manager

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. On today's show, our friend Chris calls in with a que ....

S16 E8 — 55 min

Should You Scale With a Business Loan?

On today’s episode, Clay and I dive deep into one question: should you get a business loan to grow your freelance business or agency? I’ve never taken out a loan for my business. And Clay recently decided to. So we go back and forth answering questions like: When’s the right time to get a loa ....

S16 E7 — 55 min

Perfectionists Can Scale Too—Here's How

On today’s episode, we have a coaching call with Eva—a branding expert from Portugal. Eva has gained some nice traction on Instagram and delivers her clients a highly customized service when it comes to her entire on-boarding process. But her attention to detail and propensity for perfectionism  ....

17 min

[SHORT] Should I Give Up Files for Free?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. Today's question comes from our Free Mastermind Group ....

S16 E6 — 51 min

Crushing Through Cultural Barriers

On today’s show, our guest Nouman slams us with more questions than any guest before and we do our best to deliver some good answers. Nouman has quickly grown his agency from 3 partners to over 20 employees in just a couple years. But most of Nouman’s clients still come from Upwork or Fiverr and ....

14 min

[SHORT] Can I Put In-House Work in My Portfolio?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. This episode's question came in via email. Nico works ....

S16 E5 — 52 min

Gold Mine of New Clients—Are You In?

On today’s show: are you leaving money and clients on the table? If you’re not tapping into the gold-mine we’re going to talk about on today’s show, then you’re probably missing out. It’s one of the best-kept secrets to blowing up your lead pipeline with new clients and tons of high-payi ....

15 min

[SHORT] HELP! Client Spouse Getting in the Way

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. Today's question comes from our FREE Mastermind Group ....

S16 E4 — 55 min

The Power of Client Trust

Today we’re joined by Chad who’s working on building his agency in Utah, USA. Chad works with clients all over the world. They hire him because they like and trust him.  But what’s a freelancer to do when it’s time to pass the client trust along to your team? That’s the question we answer ....

17 min

[SHORT] I've Lost My Passion, Now What?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. In today's SHORT, Rachel Stoneking, from our free Fac ....

S16 E3 — 54 min

Is Scaling Your Business Really Worth It?

On today’s show: is scaling your business really worth it?  It’s a question that makes you think. I mean, if you’re making pretty good money working as a solopreneur, what are the advantages to growing your business? And do those advantages outweigh the headache and stress of hiring, training ....

18 min

[SHORT] Should I Make This Big Leap Into a Different Industry?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. In today's SHORT, Preston asks Clay for advice in reg ....

S16 E2 — 50 min

Mastering Stress-Free Delegation in Your Business

On today’s show: How can you confidently delegate to your team, knowing things will actually get done the right way? It’s a tough question. That’s because, as a solopreneur it can be easy to want to do everything yourself. But soon you’ll find that mentality burns you out and holds back your ....

13 min

[SHORT] Does Niching Down Waste My Skills?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. In today's SHORT, we'll answer a question that comes  ....

S16 E1 — 54 min

Drumming Up More Attention

Have you ever thought: “if I can just get the attention of more people, I could close more clients and grow my business” That’s where we find today’s guest, Jay. He’s a web developer and SEO expert in Kentucky USA. And Jay’s only been freelancing for a few months. He’s off to a great s ....

11 min

[SHORT] Selling Old Files to a Client

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. In today's SHORT, we'll answer a question that comes  ....

S15 E10 — 41 min

Should You Charge for Deliverables or Results?

On today’s show, Clay and I are on our own to discuss something we’ve seen a lot of freelancers and agency builders struggle with.  The question…? When selling your services which is better: focusing on deliverables or results? After a quick discussion, the answer we come up with might surpri ....

13 min

[SHORT] What Does Your Freelance Pricing Say About You?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. In today's short, I want to answer one of the most co ....

S15 E9 — 50 min

When to STOP “Doing Everything”

Have you ever wondered if you’re doing too much in your business? For those of us who are multi-talented, it can be hard to know when to stop doing everything in our business. That’s just one question we tackle with today’s guest, Grant. As he explains it, one of his biggest problems is he has ....

18 min

[SHORT] Are Proposals Really Worth Your Time?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. Today’s question comes from our free Mastermind gro ....

S15 E8 — 61 min

Are You Ready to Hire Your First Virtual Assistant?

On today’s show: maybe you’ve heard expert advice saying you should hire a VA—a virtual assistant. You might have even heard that advice from us, on this show. But what exactly should you hire a VA for? And is hiring a VA really worth the money? Those are two questions we explore on our coachi ....

12 min

[SHORT] Best Software for Getting Paid Faster?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. Today’s question comes from our free Mastermind gro ....

S15 E7 — 44 min

Give up Control to Build a Successful Business

On today’s show: are you a bit of a control freak? Being hesitant about giving up control in your business is normal. We’re all nervous to hand off work to contractors sometimes. But if you never hand off smaller tasks, you never free yourself up to be a founder in your own business. That’s wh ....

16 min

[SHORT] Should I hire a CPA or use a tax software?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. Today’s question comes from our free Mastermind gro ....

S15 E6 — 47 min

The Power of Saying “No” to Clients

On today’s show: Have you ever noticed just how liberating it can be to tell your clients “no”? In the early years of your freelance career, you feel almost obligated to say “yes” to any request your clients make. After all, they’re the ones paying your bills.  But every “yes” to a  ....

11 min

[SHORT] Client Pays Every Month, But Doesn't Call Me...

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. Today’s question comes from our free Mastermind gro ....

S15 E5 — 62 min

Pivoting to Passive Income

On today’s show: have you ever wanted to pivot your freelance business into something a little more passive?  In this episode, we chat with our old friend Will Gibbons who came on for a coaching call a couple of years ago. Since his coaching call, Will has pivoted into a more passive business mod ....

13 min

[SHORT] When Sub-Contractors Don't Deliver

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. Today’s question comes from our free Mastermind gro ....

S15 E4 — 66 min

Breaking Free from Agencies as Clients

On today’s show: how can you stop using agency work as a crutch & build your own rolodex of high quality clients? It’s something we chat about with our first ever guest duo, Shelby & Kristina. They’re two comedic video marketers doing really fun work out of Hollywood, California. In the wake o ....

18 min

[SHORT] Impressing big-brand clients

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. On today's show, Chris calls in with another question: ....

S15 E3 — 62 min

Getting More Established Clients

On today’s show: When you’re just getting started, taking on any clients just to pay the bills is almost a given. But there comes a time when you need higher-paying more established clients. That’s the situation today’s guest, Brittany, finds herself in. Brittany has been freelancing on the  ....

15 min

[SHORT] How do I find product/market fit?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. On today's show, Chase calls in with a question: What' ....

S15 E2 — 50 min

Landing Big Clients (like Walmart) w/ Elna Cain

On today’s show: how do you go from small, one-off clients to more reputable, big-name brands? It’s a question I pose to Elna Cain, my guest on the show today. Elna is a freelance writer who has worked with big brands like Zapier or Walmart. And in this episode, Elna and I unpack exactly how she ....

14 min

[SHORT] How do I pitch a retainer?

You're listening to our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. On today's show, Dwaynia calls in with a question: How ....

S15 E1 — 58 min

Riding the Rollercoaster

On today’s show: do you ever feel like freelancing and entrepreneurship are just one crazy roller coaster ride?  Well in my conversation today with two friends Darryl and Micah, we talk all about how to convert the roller coaster of business from something negative and scary, to something positiv ....

15 min

[SHORT] Should I hire a project manager?

Big news today! We're excited to share our brand-new Freelance to Founder SHORTS, 5-10 minute episodes answering one (or two) questions from listeners like you. To submit your question, visit FreelanceToFounder.com/ASK and we'll feature you on an upcoming episode. On today's show, our friend Chris c ....

S14 E11 — 57 min

How to Find Referral Partners

On today’s show: we all know client referrals can be a great way to grow your business. In fact, most service businesses still identify word of mouth marketing as their #1 source for new clients. But if you never know when that next referral is coming, it can be a bit nerve-racking. Today’s gues ....

S14 E10 — 55 min

The Power of Productizing

Have you ever wanted to say goodbye to writing custom proposals or charging low rates by the hour? If so, today’s your lucky day. Clay’s on leave today which leaves me to chat with our expert guest, Tyler Gillespie. Tyler has grown and sold multiple productized businesses—including one he grew ....

S14 E9 — 59 min

The #1 Reason You’re Not Making Progress

Have you ever felt like you don’t know where you’re going in your business? It can be debilitating and frustrating. Not only that, but it can leave you spinning your wheels and wishing you knew what to do next to finally get some traction. That’s the situation we find today’s caller in. Her  ....

S14 E8 — 62 min

Who wins? Employees -vs- Contractors

On today’s show: Are you still debating whether you should build your business with full-time employees or independent contractors? For Josh, a former side-hustler who recently quit his job to pursue his business full-time, the question is a tough one. That’s because Josh’s business is thrivin ....

S14 E7 — 55 min

Hiring the Best Freelancers

On today’s show, have you ever thought: if I could just find the right person to hire, I could scale up my business. That’s how Virginia from Argentina feels about her unique content marketing company. The challenge? Virginia’s company develops content around witchcraft and spiritualism—so s ....

S14 E6 — 53 min

You’re a Strategist, Get Paid for It

On today’s show: have you ever wished you could actually get paid to do things like write up a proposal or send a pitch? Well, today’s guest, Austin Church reveals how he built a system to sell strategy to his clients—allowing him to get paid for a lot of the work many of us do before ever clo ....

S14 E5 — 62 min

“Risking” Money on Paid Ads

On today’s show: when’s the right time to spend money on paid advertising? If you’re not sure when or how to approach paid growth as a freelancer, you’re not alone. Our guest today, Jason, is a pastor who sells a course focused on addiction counselling and recovery. Jason has had early succe ....

S14 E4 — 66 min

Will you sink or swim?

On today’s show: what would you do if you suddenly had to start making full-time money from your business tomorrow?  In this episode, that’s a question we pose during our coaching call with Kate—a very talented motion graphics designer living in Orange County California. Kate has been buildin ....

S14 E3 — 50 min

Hate “Networking”? Do this.

On today’s show: do you keep hearing how important networking is, but you really just don’t enjoy it? In this episode, we chat with Morgan, a freelancer from Chicago. Morgan can see the potential in networking with local clients, but can’t quite figure out how to enjoy it. So, Clay and I start ....

S14 E2 — 61 min

Client Referrals: Dangerous or Powerful?

On today’s show: if you get most of your clients from referrals, is that a good thing? Or is your business at risk of failing? You’re about to hear a coaching call with Dwaynia who’s calling in from Alabama in the USA. Dwaynia has a great writing business going. She’s working with clients sh ....

S14 E1 — 66 min

The Power of Automation

On today’s “best of” episode which originally aired in Oct 2020, Preston has a one-on-one conversation with James Rose. James is a total rockstar when it comes to automating tasks in your business. In fact, as you’ll hear by the end of this conversation, in order to accomplish everything Jam ....

S13 E12 — 46 min

Powerful Lead Generation Strategy for 2022

On today’s show, it’s Clay’s birthday, so he has the day off, but I have a great conversation with Yash who built an agency from 2 people to over 55 employees in just a few years.  Now, Yash is building a tool called ClientJoy—helping thousands of freelancers and agency-builders take contro ....

S13 E11 — 55 min

Scaling without Sacrificing Personality

On today’s episode, we have a coaching call with Eva—a branding expert from Portugal. Eva has gained some nice traction on Instagram and delivers her clients a highly customized service when it comes to her entire on-boarding process. But her attention to detail and propensity for perfectionism  ....

S13 E10 — 62 min

Our Mega Productivity Episode

Today is our mega-productivity episode. It’s nearly an hour of our best tips, tricks, tools, and advice for getting more done and making more money with less time and effort. That’s the dream right: keep growing your business without working yourself to death. And in today’s show, that’s ex ....

S13 E9 — 58 min

To Retire Early, Hire These People

On today’s show, we chat with Carey from PodcastFastTrack.com where his business has taken off over the years. Carey is a bit further along in life than many of our guests and is contemplating retirement.  But instead of just selling his business, he wonders: can he just hire the right people to  ....

S13 E8 — 53 min

Spend Money to Make Money?

On today’s show, our guest skipped out, so Clay and I hit record to discuss something we see a lot of business builders get wrong: marketing budgets. You know that phrase, “you’ve got to spend money to make money”? Well, you might have thought: "that’s not necessarily true. I get referrals ....

S13 E7 — 63 min

Charge Like a Founder—Not an Employee

Today we have a coaching call with Joseph, a digital nomad working in Mexico. Joseph is building his Wordpress development company on the side of his day job with dreams of becoming a full-time entrepreneur. But there’s one major thing standing in Joseph’s way. As you’ll hear him explain duri ....

S13 E6 — 56 min

When You're Too Busy to Scale

On today’s episode, we have a great conversation with Will Gibbons—a product rendering guru who works with huge brands like Pelaton, 3M, Vizio and more. After a year of working for himself, Will is facing perhaps one of the best problems you can ask for as a freelancer: He’s got too many clien ....

S13 E5 — 53 min

Crushing it with Cold Outreach

On today’s episode, we have a coaching call with Mohcine who’s building a facebook ads business from Morrocco. Mohcine has had some great success getting jobs on Upwork, but he’s ready to diversify his marketing and has decided to go with cold outreach for starters. Clay and I give Mohcine eno ....

S13 E4 — 53 min

If We Had to Start Over from Scratch...

Today, I (Preston) got a text from Clay. "I just let my entire team go." It took me completely by surprise, but also got me thinking about what it would take to start all over. On today’s episode, Clay and I answer the question: “what would we do differently if we had to start freelancing from s ....

S13 E3 — 55 min

Getting Clients to Trust Your Team

On today’s show, we’re joined by Chad who’s working on building his agency in Utah, USA. Chad works with clients all over the world. They hire him because they like and trust him.  But now, Chad is beginning to hire some freelancers to help get the work done in his business and he's wondering ....

S13 E2 — 66 min

Filling Your Lead Generation Gap

On today’s show, we chat with Kendrick who is building a video production agency in Atlanta, Georgia, USA.  Kendrick’s a talented videographer with a highly-skilled team, but he’s feeling stuck when it comes to building a process to generate new business on a regular business. Kendrick and h ....

S13 E1 — 58 min

The Power of Personal Brand

On today’s episode, we have a coaching call with Denise, a freelancer from South Carolina, USA.  Denise works in higher education and is happy with the way her freelance business is going. But after finding some early success in e-learning thanks to Covid and other factors, Denis is ready to bran ....

S12 E12 — 51 min

A Flood of Questions (Can We Keep Up?)

On today’s show, our guest Nouman slams us with more questions than any guest before and we do our best to deliver some good answers. Nouman has quickly grown his agency from 3 partners to over 20 employees in just a couple years. But most of Nouman’s clients still come from Upwork or Fiverr an ....

S12 E11 — 51 min

Are High-Ticket Clients Enough?

On today’s show, we have a conversation with Rachel Cooke who designs high-ticket training experiences for massive clients. Rachel’s business is doing well. She’s happy with the amount of money she’s making and where her business is headed.  But she doesn’t necessarily like the fluctuatio ....

25 min

Should Managers Code?—Introducing 'Compiler', an original podcast from Red Hat

To listen to more episodes or subscribe to Compiler, click here. Technology can be bold. But it can also be complicated. Compiler breaks down the big questions about tech and the tech industry in this new original podcast. On today's bonus episode, I share with you a brand new podcast called 'Compil ....

S12 E10 — 42 min

The Freedom of Being "Out of the Loop"

Looping yourself out of every aspect of your business can be a bit terrifying. But it's also incredibly liberating. Hear why on today's show. On today’s show, I talk with Joe Babi who’s building his own SEO agency. Not long ago, Joe found himself overworked and missing out on important life even ....

S12 E9 — 53 min

Getting Agency-Quality Leads (w Big Budgets)

How can you get agency-level leads (big budgets, long timelines) when you're just a freelancer? On today’s show, we chat with Ilias a Shopify developer from Morocco. Ilias has been freelancing for over two years and thinks it might be time to move from freelancing to building an agency. He hits us ....

S12 E8 — 50 min

10 Low-Cost Marketing Tactics That Get Results

On today’s show, we share over 10 free or inexpensive marketing tactics you can use in your own business right away. And no, we’re not talking about posting on Instagram and crossing your fingers—these are real-world, high ROI marketing tactics we’ve used or continue to use to build our own  ....

S12 E7 — 63 min

Monetizing a New Skill from Scratch

On today’s show we catch up with Sara Noel, a freelancer with a pretty interesting journey. Sara didn’t study copywriting or marketing at school but now, she’s got a six-figure freelancing business doing just that: copywriting and marketing. In our conversation, Sara shares exactly what she di ....

S12 E6 — 59 min

Six-Figure Upwork Profile in 90 Days

On today’s show, Preston has a one-on-one conversation with freelance podcast expert Noah Tetzner who built a six-figure Upwork profile in under 90 days. Noah has studied the Upwork algorithm in order to find success quickly and together we discuss getting jobs on Upwork, achieving “Top-Rated Pl ....

S12 E5 — 54 min

How to Stay Motivated While You Grow

On today’s show, we chat with Mateo who’s calling in from Mexico. Mateo has been working hard as a freelancer and making pretty great money at it too. But even with all his success, Mateo still feels like he’s just trading his hourly work for a paycheck. He’s ready to go from freelancer to a ....

S12 E4 — 60 min

$100,000/mo in Recurring Revenue

On today’s episode, I’m digging into our show archives to bring you a conversation that most of you missed because we aired it so early on. If you haven’t heard this episode you’re missing out because it’s an early conversation between me and Clay about how he built his first agency to ove ....

S12 E3 — 56 min

Hiring Salespeople is Painful—Here's a Fix

Sales is one of your most important tasks as a business owner. But hiring for sales can be a nightmare. On this week’s episode, we talk with Jason Vance, a former web design freelancer who’s building his next company in marketing. Jason stumbled on a creative idea that led him to pivot and start ....

S12 E2 — 61 min

Getting Clients on LinkedIn

With millions of potential clients spending time on Linkedin, it's worth learning how to get it right. Today, we share our top tips for getting clients through LinkedIn. On today’s show, we have a coaching call with side-hustler Corey who’s building a web design business for physical therapists  ....

S12 E1 — 58 min

Growing Beyond Job Sites

Freelance job sites are a great way to get your foot in the door as a freelancer. But are they the best long-term strategy for growing an agency? On today’s show, we have a coaching call with Ron, who has been freelancing on Fiverr for over 10 years—and he’s done quite well for himself. Ron ge ....

S11 E11 — 56 min

Does Client-Hunting Keep You from Scaling?

New clients are often the lifeblood of a freelance business, but what if taking on new work is holding you back from growing your business? On today’s show, we give some coaching to Will Gibbons—a product rendering expert who works with huge brands like Pelaton, 3M, Vizio and more. After a year  ....

S11 E10 — 58 min

Can You Win at Business ... Without Burning Out?

On today’s show, we have a conversation with Corbett Barr from CorbettBarr.com. Corbett has had a huge impact on my life and business and, after a recent conversation with Clay about hustling and burning out, I knew I had to introduce them. That’s because Corbett is one of my favorite thinkers w ....

S11 E9 — 64 min

How to Unlock a Floodgate of Client Leads

On today’s episode, Caroline calls in from one of my favorite places on Earth: the Netherlands. Caroline is building a graphic and web design business and has already hired quite a few contractors. She gets a decent amount of work every month, but each new month leaves her with the frightening que ....

S11 E8 — 60 min

Getting More Clients (as an Introvert)

On today’s show, I’m joined again by my friend Matt Olpinski for our coaching call with side-hustler-turned agency-builder Jason Frostholm. After working on the side for years, Jason and his wife finally decided to take their freelancing full-time and build an agency together. That was right bef ....

60 min

Introducing 'Creative Elements'

After working with creatives for 10+ years, Clay and I know it can be hard making a living from your art and creativity. If your creative business needs a little boost, I suggest you listen to Creative Elements—a really great podcast from my friend Jay Clouse. Creative Elements is a highly produce ....

S11 E7 — 63 min

3 Ways to Finally Raise Your Prices

Today we have a coaching call with Joseph, a digital nomad working in Mexico. Joseph is building his Wordpress development company on the side of his day job with dreams of becoming a full-time entrepreneur. But there’s one major thing standing in Joseph’s way. As you’ll hear him explain durin ....

S11 E6 — 51 min

Should You Do Your Own Marketing?

Today’s coaching call is with Andy who’s calling in from Colorado, USA. And while Andy runs a business that Clay and I know virtually nothing about, he’s facing a question we have lots of answers to: Should Andy do his own marketing? He’s already working 40-50 hours a week in his business an ....

S11 E5 — 51 min

Revenue on Autopilot—Is It Really Possible?

Have you ever found yourself approaching burnout in your business and wondered: is there any way to generate revenue on autopilot? On this episode, Clay and I hit record on a rather personal conversation we were having about our businesses. The question is: can we make enough money on autopilot to  ....

S11 E4 — 58 min

Getting Press as a Freelancer (from the Editor of Entrepreneur Mag)

On today’s episode Clay and I are joined by the editor of Entrepreneur Magazine, Jason Feifer to talk about how to get press for your freelance business. Whether you want to get more visibility to your brand or attract new clients using earned media, this conversation with Jason will give you acti ....

S11 E3 — 39 min

Are You Attracting the Wrong Clients?

On today’s show, we talk with Mannat, a student calling from India with questions about her freelance business. Mannat is a typographer—she works with lettering and fonts. But everytime Mannat posts her work to social media, she gets packaging design clients and others reaching out who just don ....

S11 E2 — 50 min

Unleashing the Power of Local Clients

Today’s coaching call is with Keegan who’s calling in from Louisiana, USA. Keegan is building a web design business (something Clay knows a lot about) on the side of his day job (something I have tons of experience in). And while Keegan has a very clear picture of where he’s going, he’s not  ....

S11 E1 — 55 min

Hiring 50 Contractors in a Year (Whew!)

On today’s show, we talk with Karl who’s holding on tight while his writing business is growing fast.  After writing for a few highly technical development blogs, Karl’s business exploded and he now works with 50 writers to deliver articles for his clients. And while Karl is crushing it by so ....

S10 E12 — 59 min

Close 90% of Clients (without Proposals)

On today’s episode we chat with Brady, who is building a web design business from his home in northern Idaho, USA. Brady has already built up a small team of contractors and aims to get the business running almost on autopilot in the next 6-12 months. To do that, he’s got to first perfect his sa ....

S10 E11 — 52 min

Coaching at Scale

On today’s episode, we chat with Brendan—a sales consultant who wants to scale his business to something bigger. And while he finally started hiring people to help him scale, he’s still a bit unsure about a path forward. He’s working on a course for more passive income and he’s trying to t ....

S10 E10 — 50 min

How to Speak Your Clients' Language

On today’s show, we chat with Jon who’s a physical product designer and prototyper.  Jon’s got a highly technical business—which you’ll see as we chat with him on the episode today. That means that Jon is very smart when it comes to product design and 3D printing, but has a hard time tran ....

S10 E9 — 45 min

Should You Branch Out or Niche Down?

On today’s show, we chat with Christine, the founder of Bryant Creative Company. Christine has a nice freelance business where she works on graphic design and branding for her clients.  But over time, Christine has also begun to offer additional services such as web design—which, frankly, she d ....

S10 E8 — 62 min

Do You Have the Wrong Target Audience?

On today’s show we chat with Augusto who’s running a local branding and video marketing company in the United States. Augusto has chosen to target local latino businesses because he feels they’re underserved and can really use his expertise. But Augusto keeps hitting a wall: his target audienc ....

S10 E7 — 54 min

You've Been Lied to About "Work/Life Balance"

On today’s episode we chat with Adii Pienaar who recently published a book titled Life Profitability: The New Measure of Entrepreneurial Success. As someone who’s very motivated by the lifestyle that freelancing and entrepreneurship can offer, I was intrigued when I first learned about Adii’s  ....

S10 E6 — 61 min

Do Clients Treat You Like an Expert? or Employee?

On today’s episode, we have a conversation with Matt Essam who helps freelancers attract and find their dream clients. Have you ever felt like you are more of an employee than a partner when it comes to your client relationships? Maybe you feel like you don’t have any creative input on your proj ....

S10 E5 — 51 min

Collabs vs. Hiring

On today’s show, we check in with Margaret Ryland. Now, if that name sounds familiar, that’s because Margaret joined us originally on Season 8 to talk about her branding and design business. Since we last talked, Margaret has had some luck on collaborating with other creatives, but is still stru ....

S10 E4 — 49 min

12 Mo. of Revenue in 30 Days

On today’s show, it’s just Preston and Clay. That’s because in early January, Preston asked Clay how things were looking for the new year and his response was something like: "I’ve already hit my 6 month revenue goal." Yeah, it was January 7th. NUTS! A couple weeks later—Before January was ....

S10 E3 — 52 min

Less Convincing, More Closing.

On today’s episode we have a coaching call with Shelley, who works in the music industry—which can be a tough gig right now, but Shelley is making it work. There’s just a small problem with her principal business—booking artists into venues. Getting clients to understand the value Shelley br ....

S10 E2 — 48 min

Are You Stuck in "Create" Mode?

On today’s show, we have a chat with Erica who, frankly, intimidates both Clay and me. That’s because Erica is working with some of the brightest people in the world to solve some of the biggest problems faced by humanity. But despite working with some incredible clients and solving some meaning ....

S10 E1 — 61 min

3 Ways to "Spy" on Your Ideal Client

3 Ways to Spy on Your Target Audience  On today’s episode, we have a coaching call with Nikolai—a freelance Webflow developer living and working in New Zealand. Nikolai’s entire freelance business completely turned around when he decided to focus exclusively on Webflow, showcasing the power o ....

S9 E14 — 67 min

Leader vs. Entrepreneur

On today’s episode, we have a great coaching call with Andrea, who’s growing her agency—helping companies get the most out of the popular marketing software, Hubspot.  Andrea has hired contractors to help grow her business in the past and just a month before this conversation, Andrea hired he ....

S9 E13 — 65 min

Are You Optimizing for Profit?

On today’s episode, we chat with Yusef who’s building his own small product design agency. Yusef’s got a lot going for him: he’s got great cashflow, he’s getting new clients regularly, and he enjoys the work he’s doing. But when it comes to the most profitable projects in his business, h ....

S9 E12 — 48 min

Getting Out of Your Own Way

In today’s episode, we chat with an up-and-coming agency-builder, Maddie. And during our conversation we come up against one of the most common issues hold many of us back: Getting out of our own way. The thing is, Maddie is extremely bright. She’s got a lot of great things going. And she’s go ....

59 min

Will Clients “Subscribe” to Freelancing?

On today’s episode we mix it up a bit with Craig Solid—a consultant in the healthcare space. Craig’s business is going well and he’s trying to figure out how to better serve his clients on an ongoing basis and potential find some subscription revenue as well. What we uncover is a potential m ....

S9 E11 — 58 min

Make Art, Make Money

On today’s show I (Preston) have a really great conversation with James O-Reilly, an indie artist who’s working on making the transition from freelancer to founder. James has had heaps of work come in over the last year which is good because he's making good money as an artist, but he’s not ex ....

S9 E10 — 24 min

Working From Anywhere (Remote Works Podcast Sneak Peek)

To listen to more episodes or subscribe to Remote Works, click here. On today's bonus episode, I share with you a fun podcast called 'Remote Work' from the team at Citrix. You know how, before Covid, only a relative few of us knew how great it was to work from anywhere? Well, Remote Works is on a mi ....

S9 E7 — 60 min

The Truth About Being a ‘Founder’

On today’s episode, we chat with Chase, a co-founder at Electric Eye. They help Direct-to-Consumer Shopify brands make more money. Like Clay and me, Chase started out as a freelancer, but over the last five years he and his business partner have grown their agency to eight employees. In this conve ....

S9 E6 — 53 min

Giving Yourself a $40K Raise + Investing in People

On this week’s episode, we check back in with one of our favorite guests from last season: Amy Kuo. Amy’s business is growing well and she even hired her first intern this year. But she still has a lot of questions about hiring and outsourcing. And since Clay and I believe whole-heartedly that p ....

S9 E5 — 51 min

Attracting the Best Projects

You'll be happier and wealthier if you can learn how to attract the right kinds of freelance jobs in your career. On today’s episode, I’m joined by a special guest coach, my friend Matt Olpinski, as we offer some coaching to Wyatt Hill.  Wyatt’s got a really unique situation: his boss allows  ....

S9 E4 — 51 min

Getting Clients to Treat You Like an Agency

On today’s show, I’m joined by a good friend of mine, Chelsea Baldwin as a special guest coach. Together, we coach Australian freelancer-turned-agency-builder Caroline. She has built up a nice freelance business and has begun to work with subcontractors to begin scaling her business. But she’s ....

S9 E3 — 59 min

The Power of Automation

On today’s episode, Preston has a one-on-one conversation with James Rose. James is a total rockstar when it comes to automating tasks in your business. In fact, as you’ll hear by the end of this conversation, in order to accomplish everything James automates in his business, he’d have to hire ....

S9 E2 — 35 min

Control Freaks Can Scale Too...Here's How

On today’s show, we have a really great conversation with Natalie, who has built a nice freelance design business but has also encountered some serious trouble when it comes to hiring. And even though Clay and I both know how critical hiring can be to your scaling success, we can also empathize wi ....

S9 E1 — 47 min

Crushing Your To-Do List

On today’s episode, we have a coaching call with Ignacio, who’s building a growing web design business in Guatemala. Ignacio’s business is doing well, but he knows if he wants to go from freelance to founder, he needs to get more organized.  So in today’s call, we coach Ignacio through how  ....

S8 E17 — 50 min

How I Finally Became My Own Boss

On today’s episode (the final episode in our eighth season) I want to turn the tables and share with you an interview I did with my friends Marc and Julia at The Clearing. I’ve done dozens of interviews over the years, but Marc seems to ask the perfect questions in this interview—leading to on ....

S8 E16 — 57 min

Should You Ever Turn Down a New Client?

Do you ever get the feeling you're attracting the wrong kinds of clients for your freelance business or agency? Today's guest faces the same question: "how can I turn down clients who aren't a good fit?" Paul Chris Luke spent his first few years out of college working at an agency doing digital mark ....

57 min

I Caught Covid-19 and Lost Half My Business. But Then....

Imagine catching the coronavirus and losing half of your clients in less than 48 hours. That's what happened to today's guest, Jim Huffman. Jim runs GrowthHit, a conversion-focused agency serving tech companies and startups. When Covid-19 hit the U.S. in March of this year, Jim got an email from one ....

S8 E14 — 67 min

Getting Clients via Affiliates, Social Media, or Email

On today’s show, we talk with Akshat Choudhary who runs a thriving business called BlogVault. Despite having over 10,000 customers and a growing team, Akshat’s not sure where to go next when it comes to getting more customers. That all-to-common problem leads us to a conversation on building an  ....

S8 E13 — 55 min

How to Scale When You Feel Too Busy

On today’s episode, we have a great conversation with Will Gibbons—a product rendering expert who works with huge brands like Pelaton, 3M, Vizio and more. After a year of working for himself, Will is facing perhaps one of the best problems you can ask for as a freelancer: He’s got too many cli ....

S8 E12 — 55 min

Fixing Awkward Money Conversations w/ Clients

On this week’s episode we have a heart-to-heart chat with Bri Earles, a freelance social media manager and virtual assistant. Bri has never had any trouble getting new social media clients. But whenever Bri thinks about having money conversations or raising her prices, she kinda freezes up—using ....

59 min

Cold Pitching vs. Content Marketing

On today’s call, we chat with Mihai Zamfir who has done some incredible work in building a presentation design company. Mihai gets a fair amount of new clients using sites like Upwork and other freelance marketplaces, but he’s ready to start finding better clients in more intentional ways. All o ....

S8 E10 — 56 min

You're a Bottleneck—and it's Killing Your Business

On this week’s episode, we talk with Jason Vance, a former web design freelancer who’s building his next company in marketing. In just 9 months, Jason has hired 9 employees for his marketing agency because there's a whole lot of work that needs to get done. But now Jason feels like he may be hol ....

S8 E9 — 41 min

An Audience is Not a Business

On this week’s episode, Clay and Preston have a heart-to-heart chat with Rodney Little, a UX/UI designer who wants to build an audience-first business. But Rodney, a side-hustler with a full-time job, has been kicking this idea around in his mind for a whopping five years—so in this episode, Cla ....

S8 E8 — 52 min

Do I Really Have to Be the CEO?

On today’s show, we talk with Spencer Blaiklok—a freelance animator who dreams of building something bigger. But, like most creatives, Spencer doesn’t want to give up the fun creative work in order to sit behind a desk or in meetings all day, hating his job. In this episode, Clay and I walk Sp ....

S8 E7 — 38 min

5 Triggers to Raise Your Rates

In today’s episode, Clay and I talk all about freelance pricing: what to charge, and when to raise your rates. We explore two very different pricing models and reveal 5 triggers you should watch for to signal it’s time to raise your rates. If you’ve ever wondered if you’re leaving money on t ....

S8 E6 — 54 min

Is Upwork Legit? + What You're Losing by Not Hiring

On today’s show, we have a nice long chat with Carl Smith. He’s been an in-house web developer for the past 20 years, but at the end of 2018, Carl finally launched a small business of his own—L&L Web Consulting. Carl saw some early success on Upwork, but when one client who was taking up 50 ho ....

S8 E5 — 44 min

Why You're Failing at "Finding a Niche"

On today’s episode, we sit down with Margaret Ryland, a brand and identity designer who started her own design business not very long ago. Margaret is working hard trying to figure out exactly what kind of client to target which has left her listening to and reading a lot of advice about finding y ....

S8 E4 — 57 min

Building a Business vs. Creating Another Job

Too many freelancers never actually build a business that works for them. Instead, they just build another job for themselves—trading one annoying boss for a dozen high-maintenance clients. Eesh. In today's episode, we sit down with Bobby Macey, founder of Macey Media. After side-hustling through  ....

S8 E3 — 56 min

Is Social Media Worth Your Time?

Auni Milne can close a deal with just about any client that comes her way. But getting new clients continues to be a struggle. Can being more active on social media help Auni improve her inbound lead generation? We explore that question on today's episode of Freelance to Founder. Leave us a review o ....

S8 E1 — 44 min

Be Yourself, Get More Clients

On today’s episode, we sit down with Amy Kuo—a former designer at Disney who after finding her passion for branding, and taking the leap into full-time freelance, wants to grow her own agency. We talk about one of Amy’s biggest hurdles: overcoming imposter syndrome—especially when trying to  ....

S8 E1 — 59 min

Clay's Fight to $100K/month in Repeat Client Revenue

Not long ago, Clay was a struggling freelancer working low-paying jobs to make ends meet. Just 4 years later, he had a thriving agency with 10+ employees and over $100K/mo in recurring revenue. In today's episode, you'll get to know Clay better and see why he's going to make an incredible co-host fo ....

S8 E1 — 2 min

We're Back on April 9 with All-New Episodes!

Freelance to Founder is back with all new episodes beginning April 9th. The critically acclaimed podcast for freelancers is getting a major upgrade with two new hosts and an all-new format. You can think of it as free, weekly freelance coaching from two guys who have gone through the process of scal ....

2 min

A Year-End Announcement from 'Freelance to Founder'

A quick update from the team at Freelance to Founder: Over the last few episodes, you’ve heard show creator Preston explaining that he’d be taking over as the new host beginning in January. Today's quick audio clip makes just a small adjustment to that announcement. Since many of you who listen  ....

62 min

Escaping debt and a cubicle to build a $150,000/yr business with Whitney Hansen

In today’s episode, we feature the story of Whitney Hansen, blogger, podcaster, and creative entrepreneur. If you enjoyed this episode, please leave us an honest rating on Apple Podcasts. • • • • • Add your voice to the show Starting next year, we want to add your voices to our conversat ....

70 min

WordPress freelancer builds $1M business in 6 months

In today’s episode, we feature the story of Adam Preiser - founder of WPCraft. If you enjoyed this episode, please leave us an honest rating on Apple Podcasts. Add your voice to the show Starting next year, we want to add your voices to our conversations on Freelance to Founder. Soon, we'll be tal ....

41 min

How Chris Do is Building a Multi-Million-Dollar Agency

In today’s episode, we feature the story of Chris Do - founder of the branding agency Blind. If you enjoyed this episode, please leave us an honest rating on Apple Podcasts. Complete show notes for this interview with Chris Do can be found on our website. Add your voice to the show Starting next y ....

68 min

Building a $30K/mo company with podcaster-turned-CEO, Matt Johnson

In today’s episode, we feature the story of Matt Johnson - founder of PursuingResults. If you enjoyed this episode, please leave us an honest rating on Apple Podcasts. Complete show notes for this episode can be found on Millo.co Add your voice to the show Starting next year, we want to add your  ....

68 min

How Ever Gonzalez Left His Day Job Behind to Host Events All Over the U.S.

Ever Gonzalez is the mastermind behind OutlierHQ, but his journey to success wasn't quite what you'd expect. Tune in to learn how Ever went from working long hours in the freight industry to doing work he loves so much he would do it for free. Important note: This is Brandon's last episode as the ho ....

65 min

How Tedd Evers Grew an All-Virtual Team of 10 People While Staying Profitable

In today's episode I introduce you to Tedd Evers, founder of Trip Tuner. How do YOU book your travel? Direct with airlines, through a service like Expedia or Travelocity? Through a travel agent? Well, 8 years ago, Tedd, an avid traveler himself, conceived of a more personalized travel 'shopping' exp ....

78 min

From the US Army & Wall Street to Finally Starting His Own Business with Michael Pratt

Offline, Michael Pratt is the CEO and Co-founder of Panamplify, a really cool reporting tool specifically for digital agencies to use with their clients, with features and design that will blow away what you've seen from most white label solutions out there. Michael started Panamplify only after run ....

53 min

How Two Friends Poured Their Hearts Into a Million-Dollar Business

In this episode, you're going to be introduced to Quilt. Founded by our primary guests today, Ashley Sumner and Gianna Wurzl, two women still in their twenties, who wanted to break womens' reliance upon our digital social networks to help members form real social networks. Quilt members and then you ....

80 min

How Shane Built an 8-Figure Business & Paid Freelancers $50 Million in the Process

Shane Snow has helped build Contently to a mid-eight-figure business. But the number he's most proud of? The $50 Million in freelance wages he's passed on to freelancers around the world over the last 7 years. That's because while Contently is a content marketing platform and service for huge compan ....

62 min

How to Reach $1,000,000 in Under 2 Years (with Almost No Experience)

Coworkers Reagan and Ryan worked together at a tech company, but their desire to start a direct-to-consumer fashion brand led them on an incredible journey. Now, less than 2 years later, these two entrepreneurs run Vaer watches, a direct-to-consumer watch company that's thriving. They've surpassed o ....

62 min

From charitable "underwear run" to building a $6,500 /mo. business helping startups and freelancers

Mat Sherman doesn't do anything the "traditional" way. That includes building his business which centers around two primary products: Publoft and Gigloft. In this episode, you'll hear Mat's story including his college charitable efforts organizing an "undie run," his time with famed Angel investor J ....

85 min

How to build a $450,000/year business when college fails you twice with Matt Giovanisci

School just wasn't Matt's thing. Like, ever. He hated school and, honestly, didn't do well in it. He gave college a try...twice, and it just wasn't for him—much to the disappointment of his father. But none of that slowed him down. Over 10 years ago, Matt started a blog all about swimming pool and ....

68 min

How Spencer built 200 websites that made $1/day (and then way more!)

Spencer Haws is an SEO master. He also knows scale. Because plenty of people have built singular niche websites and monetized them, but this is a guy you can safely follow and learn from at NichePursuits because he's built over 200 highly focused websites that do extremely well in Google. In this ep ....

67 min

How getting deployed to Bahrain forced Stephanie to build her business from scratch

Stephanie isn't what you'd call a "typical" online entrepreneur. In fact, she has had tons of success at multiple desk jobs. But when her husband was deployed to Bahrain, everything changed. A few years later, Stephanie is te author of Eating Like You Give a Damn, founder of a rapidly growing Facebo ....

82 min

How Scott quit his job after thousands of customers joined "Scott's Cheap Flights"

Before he ran Scott's Cheap Flights, Scott Keyes was a journalist who freelanced on the side. He loved the work, in fact. He wasn't tired of working. It wasn't due to extreme boredom, hatred of the 'cubicle life,' so to speak or anything along those lines, that caused him to start his own business.  ....

68 min

How to convince huge brands to become your clients: the 7-year journey of Springzy

Charlie Francus knew knew he'd be an entrepreneur one day. It took a little while for the right idea to fully germinate but about 7 years ago he finally launched his company, Springzy, and now works with some giant brands in the food industry. Springzy is a combination of software and service that  ....

68 min

How to build a $130K side-hustle in 6 months with Ben Tossell

Today's guest on Freelance to Founder is at the very forefront of the "no-code" movement: a new way of building tech-based companies without being a developer. He's the founder of Makerpad, an educational platform that features tutorials for how normal human beings who might otherwise meltdown if we ....

67 min

How this freelance web developer got 400,000+ students on Udemy

Today, we chat with Brad Hussey: who went from side-hustling as a freelance web developer to bringing in 400,000+ Udemy students and a nice steady revenue to go with it. What makes this episode special is Brad's humility. We've got an immensely talented web designer, a former aspiring Broadway stage ....

S7 E15 — 63 min

How Emily quit her day job to illustrate for big brands as a full-time freelancer

Getting paid to do work you love and building a profitable business out of it is every entrepreneur’s dream. And today’s guest on Freelance to Founder has been able to make that dream into reality, hiring her husband in the process. In this episode, we interview Emily Mills, author of The Art of ....

S7 E14 — 63 min

From founder to freelancer: How Louis Nicholls has flipped the script for success

In this episode, you’ll hear the story of Louis Nicholls, founder of ‘Sales for Founders’, where he teaches sales skills for a mostly tech founder audience. What makes Louis' story so different is that it’s a 180-degree flip from our typical script. Louis went from co-founder of Gymhopper.co ....

S7 E13 — 80 min

From aspiring actor to transformational public speaking trainer

25 years ago, Michael Port earned his MFA in acting from NYU before working in TV, film, and theater. Now, at the Heroic Public Speaking Headquarters in NJ and for organizations around the world, he teaches non-actors what actors know about how to give better performances both onstage and off. Micha ....

S7 E12 — 65 min

From struggling teacher to 6 figures with John Sowash

John's story is the entrepreneur's story through and through.  A teacher for years, loving the job but struggling financially, he started to do a little consulting on the side, focusing on technology in the classroom. Until life presented him with a crossroads.  John decided to go all in - and now ....

S7 E11 — 65 min

From unemployed to an 8-figure exit with Chris Cobb

In this episode, we interview Chris Cobb of Armstrong Transport. His story is very different from many we’ve told on Freelance to Founder. Our guest built his business with a dwindling cash reserve and with no knowledge of the business he was getting into. Only trust in his own work ethic, $15,000 ....

S7 E10 — 62 min

From struggling commercial pilot to 6-figure podcaster

This is our interview with Eric Cacciatore, founder of Restaurant Unstoppable - a restaurant business podcast that enjoys a loyal audience and generates over six-figures in revenue. If you enjoyed this episode, please leave us an honest rating on iTunes. After working towards a career as a commercia ....

S7 E9 — 69 min

How to build a 7-figure blogging business around your passion with Will Hatton

This is the story of Will Hatton, founder of TheBrokeBackpacker.com and a jack-of-all-trades turned blogger/entrepreneur who converted his passion into a 9-business empire making 7 figures in revenue. If you enjoyed this episode, please leave us an honest rating on iTunes. Will’s multiple ventures ....

S7 E9 — 68 min

WordPress freelancer builds $1M business in 6 months

Adam Preiser was enjoying an early retirement in his 30's. That was until he started experimenting with YouTube—showing non-developers how to rapidly build sophisticated websites with WordPress. If you enjoyed this episode, please leave us an honest rating on iTunes. It all started with one video. ....

S7 E8 — 61 min

Escaping debt and a cubicle to build a $150,000/yr business with Whitney Hansen

Today, we talk to Whitney Hansen, who is a personal finance coach and host of The Money Nerds, a Plutus award-winning podcast. As an adjunct professor in personal finance, she teaches overwhelmed millennials how to accelerate paying off debt and be financially independent. Some of her accomplishment ....

S7 E7 — 49 min

How a hobby turned into a six-figure business for Krista Stryker

Today, you'll hear the story of Krista Stryker, founder of 12 Minute Athlete. Krista is living a comfortable life. She's married, lives in Los Angeles, California. She’s got her own fitness app, an incredible YouTube channel. Blogs for days on healthy living and activities featuring High Intensity ....

S7 E6 — 66 min

From “failure” to a $43,000/month business with Baird Hall of Wavve

In today’s episode of Freelance to Founder, you'll hear the story of Baird Hall, founder of Wavve.co. If you've seen these cool social videos floating around that feature short excerpts of podcast episodes, with a neat audiowave bouncing to the beat of the voices in that excerpt, there's a pretty  ....

S7 E5 — 56 min

Why Copyblogger co-founder Sonia still freelances on the side of her multi-million-dollar business

In today’s episode of Freelance to Founder, you’ll hear the story of Sonia Simone, co-founder and Chief Content Officer of Copyblogger. If you enjoyed this episode, please leave us an honest rating on iTunes. Copyblogger is a massive business that’s gone through quite an evolution over the yea ....

S7 E4 — 69 min

From Video Editor to $2M in Annual Revenue with Chris Ronzio

Today, you'll hear the story of Chris Ronzio, founder of Trainual. We're talking to someone who was at the `15-month mark when we interviewed them. And he's built his business to the $2 Million level in annual revenue. But when you learn about his why, and his how, it feels much more doable and unde ....

S7 E3 — 60 min

15 Months to hit six figures with freelance copywriter & stay-at-home mom, Allie Smith

This is episode number 50 of freelancetofounder and today you’re going to hear about Allie Smith, solopreneur, expert copywriter and founder of Creative Gangsters.  If you enjoyed this episode, please leave us an honest rating on iTunes.  Allie helps multiple 6 and 7 figure entrepreneurs connect ....

S7 E2 — 66 min

Passing $1 Million in her first year with one-woman company Aether Beauty

In today’s episode, we feature the story of Tiila Abbitt - CEO and founder of AetherBeauty. If you enjoyed this episode, please leave us an honest rating on iTunes. Tiila is in her first year of starting her own beauty brand, Aether Beauty, having served for years as an expert product developer at ....

S7 E1 — 67 min

Building a $30K/mo company with podcaster-turned-CEO, Matt Johnson

Welcome to a brand new season of Freelance to Founder and a new era for the show where we embrace a new, more casual and long-form approach to sharing our founder stories. In today’s episode, we feature the story of Matt Johnson - founder of PursuingResults. If you enjoyed this episode, please le ....

S6 E10 — 31 min

Building seanwes from freelance to 7 figures with Sean McCabe

This episode tells the story of Sean McCabe, founder of seanwes. Sean freelanced as a hand-lettering specialist, but ultimately turned the lessons he learned from that niche into a successful 7-figure online business. If you enjoyed this episode, please leave us an honest rating on iTunes. Complete  ....

S6 E9 — 40 min

From 3rd-grade teacher to six-figure blogger with Courtney Slazinik

A great story of a military wife. An extremely busy and motivated wife and mother who decided to mix her two passions - education and photography - into a highly successful business that she can run, and needs to run from anywhere. Complete shownotes for this episode can be found on Millo.co   This ....

S6 E8 — 30 min

From freelancer to 7-figure agency with Shannon DeJong and House of Who

In this final episode of season 6, we feature the story of Shannon Dejong - an Entrepreneur, artist, speaker, and CEO of boutique agency House of Who. Years ago, she thought she’d be an actor on a stage or writing poetry for a living. The first part of that is definitely true today as she does pe ....

S6 E7 — 37 min

Over $500K/year working just a few hours a week with Brian Casel of Audience Ops

We interview Brian Casel: entrepreneur, product designer, writer, trainer at flagship training program Productize, host of ProductizePodcast and Founder of AudienceOps, a done-for-you content marketing service. Brian Casel has an expert entrepreneur's eye for turning products into services and vice  ....

S6 E6 — 31 min

From summer camp teacher to over $300,000 in revenue with Pamela Capalad of Brunch and Budget

In today’s episode, we’re in New York City to join Pamela Capalad, a certified financial planner who’s blended her expertise in financial planning with her passion for educating and serving people of color, while leading a hip-hop-based financial education for children as well. You’ll hear h ....

S6 E4 — 36 min

From freelance writer to million-dollar BBQ blogger and a Guinness Record with Susie Bulloch of Hey Grill Hey

When grown-ups used to ask Susie Bulloch what she would be when she grew up, she didn’t stand a chance of guessing correctly. That’s because, as Susie puts it in our most recent episode of Freelance to Founder, “The business we’re in didn’t even existwhen we were kids…this just wasn’t  ....

31 min

BONUS: From stay-at-home mom to multi-million-dollar brand with Courtney Brown

This episode, we tell the inspiring story of Courtney Brown—a solopreneur who, in the height of the mommy blog craze, decided blogging wasn't for her and built a mult-million dollar fashion business instead. Subscribe for new episodes at http://freelancetofounder.com. Sponsors Gusto: Making payrol ....

S6 E3 — 31 min

From freelance writer to $300K/year with Chelsea Baldwin of Copy Power

Chelsea Baldwin has been at it building a successful copywriting business, all the while sustaining her travel lifestyle - travelling the world throughout Southeast Asia, South America and India, while building a business with over $300K in annual revenues. She gained expertise in building content w ....

S6 E2 — 26 min

Paul Jarvis: From web designer to six-figure “company of one”

For this epiosde, we head to an island. Well away from the major city - off the mainland of British Columbia, Canada. A young man has grown from an unfortunate, bedridden condition in his youth to one of the most creative, one-man businesses around. He’s done it by embracing the same counter-cultu ....

S6 E1 — 33 min

From 0 to 100k customers with AWeber's Tom Kulzer

For our first episode of season 6, we take you into rural America. It was 1998, and a young wireless modem salesperson was looking at ways to automate his follow up with potential customers via email. So, he learned how to write a script in a programming language called Perl that would make this pos ....

40 min

BONUS: Chris Do - From immigrant childhood to millions in revenue and winning an Emmy

After his family immigrated to the U.S. from Vietnam, Chris Do never imagined his artistic interests could eventually propel him into a successful life-long career. Now, years later, he's an Emmy Award-winning designer growing an agency that works with some of the biggest companies in the world.   ....

3 min

The Elephant in the Room…

We're excited to announce our partnership with 'House of Who' to bring you a brand new podcast called ArtistCEO - a podcast by women, about women in business... *** This show is a part of the Podglomerate network, a company that produces, distributes, and monetizes podcasts. We encourage you to v ....

S5 E8 — 42 min

From plumber to $4 Million business with Stuart Draper of Stukent

Stuart Draper once worked as a plumber for his brother-in-law. Now he’s the founder of a $4 Million business providing a digital marketing curriculum to university professors and their students. Makes total sense, right? Well, maybe not. But it makes for a great tale.  *** This show is a part of ....

S5 E7 — 33 min

From feeling stuck at a day job to $500K/year with Brittney Castro of Financially Wise, Inc.

After feeling stuck at her corporate finance job, Brittney Castro broke out on her own to start her own financial planning firm. Now she works tirelessly on growing her personal brand making $500K/year.  *** This show is a part of the Podglomerate network, a company that produces, distributes, a ....

S5 E6 — 33 min

From zero business plan to million-dollar podcaster with Andrew Warner of Mixergy

When Andrew Warner started Mixergy, he had just come away from a $40 Million business sale and was anxious to help aspiring entrepreneurs thrive. Despite starting with zero business plan in mind, today Mixergy is a healthy 7-figure business and in today’s episode, you’ll see how it all unfolded ....

S5 E5 — 43 min

From 3rd-grade teacher to six-figure photography blogger with Courtney Slazinik of Click it Up a Notch

We have a super founder to introduce to you today. A great story of a military wife. An extremely busy and motivated wife and mother who decided to mix her two passions - education and photography - into a highly successful photography business that she can run and needs to run from anywhere. This i ....

S5 E4 — 35 min

From freelance web designer to topping the Product Hunt charts with James Rose of Content Snare

On today’s show, we’ve got an Australian software developer, who’s just over 1 year into his biggest endeavour yet. While he’s successfully built and sold one company in the past, he’s right now growing his latest creation - Content Snare. And it’s been an emotional rollercoaster - even  ....

S5 E3 — 43 min

From PR Manager to highly successful SaaS consulting business with Kaleigh Moore

What if you discovered that your best bet for growth, success and even peace of mind was to change gears from building a big company to establishing a strong healthy personal brand? Meet Kaleigh Moore, freelance copywriter and former founder of Lumen Ventures - Now, a prolific content creator, podca ....

S5 E2 — 38 min

From freelance developer to millions in revenue with Hotjar’s Marc von Brockdorff

As a kid, Marc von Brockdorff was obsessed with the idea of having an online business. He’s continued to overcome startup struggles by building and testing various online products and businesses - including working as a freelance developer. Today, he’s the co-founder at Hotjar, one of the web’ ....

S5 E1 — 41 min

From college dropouts to power couple growing two agencies with Reliable PSD’s David & Lou

On today's show, we introduce you to David Tendrich and Lou Levit, partners in business and in life. In 2009, they both decided to leave college to start their own freelance business. Now, this power couple have grown from just the two of them to over 20 employees and thousands of dollars in revenue ....

S4 E6 — 40 min

From answering customer support calls to building a successful lifestyle business online

Justin Jackson was a shy kid growing up. Of course, you might not guess that from his twitter profile where he self-identifies as an internet stuntman. After taking his first real job as a customer service rep, Justin quickly learned there was more out there for him. Today, he's a lifestyle entrepre ....

S4 E5 — 39 min

From "checked-out employee" to full-time freelancer & blogger with Sarah Morgan of XO Sarah

After seven years of working in a cubicle, Sarah Morgan realized she had a major problem: she hated her job. Her biggest fear was that she'd wake up one day and realize she had worked her whole life at a job she didn't enjoy. That's when she decided to take her freelancing full-time and has since bu ....

S4 E4 — 32 min

From web designer to building Freshbooks to a multi-million-dollar company with Mike McDerment

Mike McDerment had the entrepreneurial bug early on. In second grade, he built a video game and told everyone he was going to sell it. Today, Mike he's the CEO of Freshbooks—a tool for freelancers with nearly 2 million active users.  *** This show is a part of the Podglomerate network, a compa ....

S4 E3 — 35 min

From “terrible student” to building a multi-million-dollar agency with Cynthia Johnson of Bell + Ivy

Cynthia Johnson wasn't exactly a perfect fit for public school—after being homeschooled she found the entire thing a bit restrictive. But the same autonomous, adventurous, entrepreneurial mindset that may have caused trouble in school, helped her build a multi-million dollar agency and personal br ....

S4 E2 — 37 min

From "nerdy kid" to building a $45,000/mo business from scratch in less than a year with Jake Jorgovan of Lead Cookie

Jake Jorgovan has started a lot of businesses—from recording punk rock bands in his basement as a teenager to designing websites for multiple clients. But Jake recently learned that if he wanted to scale to something bigger than his own expertise, he had to rethink everything.  *** This show is  ....

S4 E1 — 43 min

Chris Do: From immigrant childhood to millions in revenue and winning an Emmy

After his family immigrated to the U.S. from Vietnam, Chris Do never imagined his artistic interests could eventually propel him into a successful life-long career. Now, years later, he's an Emmy Award-winning designer growing an agency that works with some of the biggest companies in the world.   ....

S4 E1 — 3 min

Season 4 is coming with Chris Do, Cynthia Johnson, Justin Jackson, Sarah Morgan and more!

We're just a week away from Season 4 of 'Freelance to Founder' and we've got some incredible stories coming your way this season—from Emmy-winning designer Chris Do, to entrepreneur Cynthia Johnson, "internet stuntman" Justin Jackson, full-time blogger Sarah Morgan and lots more!  *** This show  ....

S3 E9 — 3 min

BONUS: Andy quit his job...now what? Listen to the trailer for our new podcast, 'My Freelance life'

From the company that brings you 'Freelance to Founder' comes an all-new weekly podcast called 'My Freelance Life.' The show tells the story of Andy, a desk-jobber-turned-full-time-freelancer. In this quick episode, you'll hear the trailer for the all-new show. *** This show is a part of the Podgl ....

2 min

A quick message for listeners of 'Freelance to Founder'

A quick message to everyone listening to 'Freelance to Founder' from co-producer and Millo founder, Preston. *** This show is a part of the Podglomerate network, a company that produces, distributes, and monetizes podcasts. We encourage you to visit the website and sign up for our newsletter  ....

S3 E8 — 36 min

From flailing freelancer to a $500,000/month "unlimited design" business with Russ Perry of Design Pickle

After realizing he wasn't cut out for freelancing or agency life, Russ Perry built a multi-million-dollar business on the back of a crazy idea: sell unlimited graphic design services for unbelievably cheap.  *** This show is a part of the Podglomerate network, a company that produces, distribute ....

S3 E7 — 29 min

From struggling design blogger to building a huge six-figure business with Tom Ross of Design Cuts

Tom Ross used to be a design blogger getting hundreds of thousands of views every month. But he quickly realized almost none of those visitors really cared about him, his brand, or his business. That's when Tom pivoted to build Design Cuts—a decision that would lead him to build one of the most en ....

S3 E6 — 30 min

From 8-yr-old computer whiz to selling his company to Stripe with Courtland Allen of Indie Hackers

When Courtland Allen was an 8-year-old tinkering with computers and teaching adults around him how the machines worked, he probably never imagined that many years later he would build a small company that would eventually be acquired y tech giant, Stripe.  *** This show is a part of the Podglomer ....

S3 E5 — 33 min

From college dropout to $828,000 in monthly recurring revenue with Nathan Barry of ConvertKit

When Nathan Barry dropped out of college a few years ago, he never dreamed he'd soon be running a company that generates over $800,000 every month in recurring revenue. But that's exactly what has happened. And in today's episode we learn how he did it.  *** This show is a part of the Podglomerat ....

S3 E4 — 29 min

From quitting law school to building a copywriting empire with Joanna Wiebe of Copy Hackers

Joanna Wiebe thought law school was the right path for her. But after a day—yes, literally one day—she realized she made a terrible mistake. Since then she has built one of the most well-known copywriting brands on the internet: Copy Hackers.  *** This show is a part of the Podglomerate netw ....

S3 E3 — 30 min

From losing everything to building a massive podcast career with Michael O'Neal and 'The Solopreneur Hour'

How many people do you know making a good living as a professional podcaster? Probably not many. In today's episode, you'll hear the story of Michael O'Neal and learn what it takes to build a creative business of any kind as we hear how he became the host of a very popular podcast: 'The Solopreneur  ....

S3 E2 — 27 min

From financial analyst to million-dollar blogger with Michelle Schroeder-Gardner and 'Making Sense of Cents'

Just a few years ago, Michelle Schroeder-Gardner was a financial analyst with loads of student debt. Now her blog, 'Making Sense of Cents,' brings in over a million dollars annually.  *** This show is a part of the Podglomerate network, a company that produces, distributes, and monetizes podcast ....

S3 E1 — 29 min

From high-school web developer to teaching freelancers how to double their business with Brennan Dunn

Brennan Dunn started freelancing as early as high-school. Now, he teaches other freelancers what it takes to build a thriving business & he runs a couple of growing businesses himself.  *** This show is a part of the Podglomerate network, a company that produces, distributes, and monetizes podca ....

S3 E1 — 2 min

Season 3 is coming—and we've got Brennan Dunn, Michelle Gardner, Michael O'Neal and lots more!

We're back with an all-new season of 'Freelance to Founder!' This season, you'll hear the stories of incredible freelancers and solopreneurs like Brennan Dunn of 'Double Your Freelancing,' Michelle Gardner of 'Making Sense of Cents,' Michael O'Neal from 'The Solopreneur Hour Podcast' and lots more!  ....

S2 E8 — 27 min

From fortune 500 companies & failed startups to building a successful business on their terms - the story of Fizzle founders Corbett Barr & Chase Reeves

Our final episode for Season 2 brings you Corbett Barr and Chase Reeves, together, as co-founders of Fizzle.co.  We especially cover the mindset of a successful online business builder.  The perfect episode to wrap up an incredible season.  *** This show is a part of the Podglomerate network,  ....

S2 E7 — 31 min

From receptionist to designing for Google and becoming a bestselling author - the story of Sarah Cooper & the Cooper Review

Episode 7 introduces you to Sarah Chooper. Sarah is the hilarious author of the best-selling book, "100 Ideas to Look Smart in Meetings," a follow-up to her post with 10 ideas.  *** This show is a part of the Podglomerate network, a company that produces, distributes, and monetizes podcasts. We  ....

S2 E6 — 30 min

From college drop-out to building a massive social selling business — the story of Phil Gerbyshak

Episode 6 welcomes Phil Gerbyshak. As Phil left the Navy, he was quick to dive into the digital world. As his career moved along, so did his mastery of the web for ethical connections. He now teaches social selling as one of several founders of Vengreso.  *** This show is a part of the Podglomera ....

S2 E5 — 29 min

From project manager to highly sought-after hand-lettering instructor - the story of Becca Courtice

Episode 5 introduces you to Becca Courtice. She was a sports nut early in life, and a project manager after university, What does she do now? She has a highly successful, full-time business as a calligraphy instructor.  *** This show is a part of the Podglomerate network, a company that produces ....

S2 E4 — 34 min

From a Boeing cubicle to making videos for Pat Flynn, John Lee Dumas, Chris Ducker & more - the story of Caleb Wojcik

Episode 4 tells the story of Caleb Wojcik, who purposely avoided the self-employed path his father took...before ultimately being pulled into it after the corporate world let him down. Hear how he navigated from employee to employer.  *** This show is a part of the Podglomerate network, a compan ....

S2 E3 — 27 min

From kindergarten teacher to Kickstarter success & thriving mompreneur - the story of AshLee Winterrose

Episode 3 brings you AshLee Winterrose. AshLee and her husband were dealt a challenging blow while still in college, forcing her to become the primary family provider. Hear how she went from meager teacher's salary to budding entrepreneur.  *** This show is a part of the Podglomerate network, a  ....

S2 E2 — 30 min

From getting fired to building a thriving creative agency - the story of Clay Mosley and Rock City Digital

Episode 2 introduces you to Clay Mosley, founder of Rock City Digital agency in Little Rock, Arkansas. Clay went from self-proclaimed job hopper to creative visionary and CEO of an unorthodox agency in the Midwest.  *** This show is a part of the Podglomerate network, a company that produces, di ....

S2 E1 — 32 min

From washing windows to building a massive online brand — the story of Sean McCabe and the seanwes brand

Episode 1 tells the story of Sean McCabe, founder of seanwes. Sean freelanced as a hand-lettering specialist, but ultimately turned the lessons he learned from that nicheinto a successful online business.  *** This show is a part of the Podglomerate network, a company that produces, distributes, ....

S2 E1 — 4 min

Season 2 is coming in one week with Sean McCabe, Sarah Cooper, Corbett Barr & Chase Reeves, and more!

Here's what you can expect from Season 2 of Millo's first-ever podcast, 'Freelance to Founder.'  *** This show is a part of the Podglomerate network, a company that produces, distributes, and monetizes podcasts. We encourage you to visit the website and sign up for our newsletter for more in ....

S1 E8 — 32 min

From freelance designer to building a luxury fashion brand

Jeff was a freelance designer who started to notice it was hard to find quality t-shirts that he actually wanted to wear. So he decided to start his own design & fashion brand, Ugmonk. Now, Jeff sells luxurious high-end fashion basics and accessories to people with an eye for great design.  *** Th ....

S1 E7 — 30 min

From designing video games to getting hired by major brands to create custom illustrations & art

Ever since we was a little kid, Howard loved fantasy games like Dungeons and Dragons. But little did he know he'd grow up be hired by Dungeons and Dragons plus other huge gaming brands like Blizzard. Today, Howard does commission work for enormous brands and sells one-of-a-kind commissioned art.   ....

S1 E6 — 31 min

From cubicle-doomed to getting his brand featured on TODAY Show & in the Superbowl—the story of Michael Brown

Michael was an accountant with a dead-end job that wasn't making him happy. So he decided to purchase a small local coffee business. After attempting a unique online business model, he came within 2 months of complete failure. But after getting featured on the TODAY Show and in the Superbowl, his br ....

S1 E5 — 32 min

From college grad to sought-after photographer working with ESPN, Oprah, Time Mag and more - the story of CJ Burton

C.J. was a no-name freelance photographer who walked into the offices of Time Magazine to pitch his work...and got the contract. Years later, he has worked with brands like Oprah, ESPN, and Time Magazine.  *** This show is a part of the Podglomerate network, a company that produces, distributes, ....

S1 E4 — 30 min

A trip to Asia led this solopreneur to marriage and a business that empowers women in third-world countries - the story of Adrienne Thakur

Adrienne never expected a vacation to Nepal would lead to not only her eventual marriage, but the beginning of an art business that empowers female artists in Nepal.  *** This show is a part of the Podglomerate network, a company that produces, distributes, and monetizes podcasts. We encourage y ....

S1 E3 — 30 min

From one-woman designer to selling millions in client work - the story of Bianca Board

Bianca Board started out as a one-woman graphic design "agency" and has built a thriving Aussie web design business with 20 employees—bringing in millions of revenue along the way.  *** This show is a part of the Podglomerate network, a company that produces, distributes, and monetizes podcast ....

S1 E2 — 29 min

From pennies in royalties to selling high-end art direct to customers - the story of Nate & Greg Olsen

Greg was an artist getting paid pennies on the dollar in royalties for his religious artwork. But after his son Nate stepped in to help build a direct-to-consumer ecommerce business, profits soared.  *** This show is a part of the Podglomerate network, a company that produces, distributes, and m ....

S1 E1 — 33 min

From stay-at-home mom to multi-million dollar brand - the story of Courtney Brown

Episode 1 tells the story of Courtney Brown—a solopreneur who, in the height of the mommy blog craze, decided blogging wasn't for her and built a mult-million dollar fashion business instead.  *** This show is a part of the Podglomerate network, a company that produces, distributes, and moneti ....

S1 E1 — 2 min

Season 1 Trailer - Freelance to Founder

Season 1 of Millo's all-new podcast 'Freelance to Founder' is about to launch! Here's a peek at what to expect this season.  *** This show is a part of the Podglomerate network, a company that produces, distributes, and monetizes podcasts. We encourage you to visit the website and sign up for  ....

Show fewer episodes

Free on-air business coaching for freelancers.

On this show, real-life freelancers get 100% FREE on-air coaching to help them scale their business. And we want to chat with you!

Here's how to get on the show:


1. Book a time

Choose a time to get your free on-air business coaching to be included in an upcoming episode.


2. Tell us more

Tell us more about your business and your future goals by filling out this questionnaire.


3. Get ready

We'll email all the details you need to join us on the air. We can't wait!

Please select an episode...
00:00 00:00