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 during the show, Joseph is charging what he calls “employee” prices which just doesn’t give him enough cashflow to scale. Clay and I are up to the challenge as we spend the full second half of the episode tackli...
Nov 25, 2021•1 hr 3 min•Season 13Ep. 7
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 client requests coming in and too much work that needs done. So in this episode, Clay and I walk him through a few hiring, scaling, and management tips to help him go from freelancer to agency without losing con...
Nov 18, 2021•56 min•Season 13Ep. 6
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 enough great advice to fill 3 pages with notes about cold pitching to grow your business. ATTENTION: We Need YOU! We're currently casting new guests for our upcoming season and we want to feature your business...
Nov 11, 2021•53 min•Season 13Ep. 5
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 scratch today?” We think you'll be pleasantly surprised by some of what we share. Have a listen. ATTENTION: We Need YOU! We're currently casting new guests for our upcoming season and we want to feature yo...
Nov 04, 2021•53 min•Season 13Ep. 4
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: how can I get my clients to trust my team? Building trust in your team can help take some work off your shoulders and free you up to continue growing your business. But transferring trust can be fragile and...
Oct 28, 2021•55 min•Season 13Ep. 3
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 his former partner went their separate ways recently, leaving Kendrick without someone to handle all the business development full-time. So Clay and I walk him through a few options for filling in the lead gene...
Oct 21, 2021•1 hr 6 min•Season 13Ep. 2
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 branch out and grow other segments of her business. Throughout the call, we keep coming back to two critical themes: the importance of building your brand and the power of opportunity costs. If you want to bu...
Oct 14, 2021•58 min•Season 13Ep. 1
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 he’s unsure how to break into more legitimate, bigger clients—particularly in countries where cultures are so different. We talk about how to hire the right people, how to overcome cultural barriers, whe...
Oct 07, 2021•51 min•Season 12Ep. 12
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 fluctuation in revenue and not knowing exactly how much she’ll make in the coming months or years. So Clay and I walk her through a few ideas including how to diversify her product offering in a way that might bring in som...
Sep 30, 2021•51 min•Season 12Ep. 11
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 'Compiler', an original podcast from Red Hat. Becoming a manager can be a triumphant milestone of working life. It’s often a recognition of leadership and, in the tech industry, technical skill. Many argue t...
Sep 28, 2021•25 min
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 events. That’s when he realized he HAD to make a change. So over the last year or two, Joe has scaled his agency in a way that loops him out of his business more and more. Being okay with being "out of the lo...
Sep 23, 2021•42 min•Season 12Ep. 10
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 with a lot of great questions, including: "how can I find agency-quality leads?" Projects with big budgets, established companies, and larger scopes or timelines. Clay and I do our best to answer that ...
Sep 16, 2021•53 min•Season 12Ep. 9
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 businesses. Get your own on-air coaching call We'd love to feature your business and offer some free on-air advice for growing your business. To see if you're a good fit, click here. Leave us a review on Appl...
Sep 09, 2021•50 min•Season 12Ep. 8
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 did to decide on a skill, teach herself that skill, and then monetize her brand-new skill into a full-fledged business. Whether you want to learn a new skill to offer your current clients, or want to pivot to...
Sep 02, 2021•1 hr 3 min•Season 12Ep. 7
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 Plus” status (and why you want it), plus how to replicate his success even if you're just getting started on Upwork. If you’ve wondered if Upwork is worth your time—or your Upwork profile needs a boost, thi...
Aug 26, 2021•59 min•Season 12Ep. 6
On today’s show, we chat with Mateo Melgar 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 agency and build a business that makes money beyond himself. But being ready and actually feeling motivated and accountable are two very different things. So Clay and I help Mateo break down a few ways ...
Aug 19, 2021•54 min•Season 12Ep. 5
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 over $100,000/mo in recurring revenue. Those of you who are quick at math have already figured out that means over a million dollars in predictable, recurring income per year. And Clay started the whole thing as a...
Aug 12, 2021•1 hr•Season 12Ep. 4
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 a marketing agency late last year. Now, just 9 months later, he’s got 9 employees and a whole lot of work that needs to get done. But hiring the right salespeople is something Jason just hasn't figured o...
Aug 05, 2021•56 min•Season 12Ep. 3
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 and other health professionals. Among other things, we end up talking in-depth about using Linkedin to get more clients. Our guest co-host and my friend Chelsea Baldwin and I share some of our tried-and-t...
Jul 29, 2021•1 hr 1 min•Season 12Ep. 2
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 gets a ton of new business from Fiverr, but he’s worried about two things: first, it can be difficult to build long-term relationships with clients on Fiverr and second, if there was an algorithm adjustment o...
Jul 22, 2021•58 min•Season 12Ep. 1
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 of freelancing, Will is facing perhaps one of the best problems you can ask for: He’s got too many client requests coming in and too much work that needs done. So in this episode, Clay and I walk him thro...
Jul 15, 2021•56 min•Season 11Ep. 11
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 when it comes to balancing life with the hustle of entrepreneurship. Corbett’s insights lead us down a path answering questions like: what am I giving up by hustling all the time? Do I really need to promo...
Jul 08, 2021•58 min•Season 11Ep. 10
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 question: Will we get enough new business this month? With some good lead generation in place, a team working at about 20% capacity, and a desire to grow, she’s in a perfect place to make fast progress. To...
Jul 01, 2021•1 hr 4 min•Season 11Ep. 9
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 before the global pandemic. Now, after a year of eating into savings, they’ve used word-of-mouth to build up some good relationships and they have the beginnings of a solid client base. But, as any agency-bu...
Jun 24, 2021•1 hr•Season 11Ep. 8
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 produced narrative-interview show where Jay talks to high-profile, successful creators about how they built a business from their creativity. He’s had conversations with legendary marketer Seth Godin, Grammar ...
Jun 22, 2021•1 hr
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 during the show, Joseph is charging what he calls “employee” prices which just doesn’t give him enough cashflow to scale. Clay and I are up to the challenge as we spend the full second half of the episode tackli...
Jun 17, 2021•1 hr 3 min•Season 11Ep. 7
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 and he’s trying to figure out who to hire next, where to find them, and what tasks to assign them. It’s a common question for service-based businesses: should you focus on doing the work for current clients or ...
Jun 10, 2021•51 min•Season 11Ep. 6
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 finance a nice lifestyle without having to put in long hours every single week or—as Clay hopes—without really any work at all. Throughout the episode, I share how I’ve outsourced most of my daily task...
Jun 03, 2021•51 min•Season 11Ep. 5
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 actionable, real-world advice on getting featured by journalists and influencers. We also kick off the conversation chatting about the current state of freelancing and the future of freelancing in a post-pa...
May 27, 2021•58 min•Season 11Ep. 4
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’t match her target audience. This leaves Mannat asking “what exactly should I be posting on social media to attract my ideal client?" We walk her through a few key social media strategies that’ll also hel...
May 20, 2021•39 min•Season 11Ep. 3
