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    • Please join me in welcoming Preston D Lee from the podcast Freelance to Founder for a Panel here on Cake! Preston Lee is the co-producer of 'Freelance to Founder' a podcast where he helps tell the real stories of freelancers and solopreneurs who have scaled their businesses to be much bigger than themselves. This season, show host Brandon Hull shares the stories of millionaire podcaster AJ Harbinger, freelancer-turned-agency-builder Chelsea Baldwin, freelance expert Paul Jarvis, and lots more. You can listen to this season and all previous seasons by searching "Freelance to Founder" wherever you get your podcasts or visiting

      Welcome Preston!

    • First of all, I run a site for freelancers called Millo where we've been blogging for about a decade. So I love working with freelancers and entrepreneurs. And I'm a huge podcast listener myself.

      When podcasting really starting gaining a resurgence 4 or 5 years ago, I noticed a couple of things: first of all I loved some of the more popular Narrative-driven shows like This American Life. Secondly, I noticed that the majority of new and old business shows focused primarily on tech startups with millions in funding and most of them were produced strictly in an interview format.

      I decided I wanted to take the more narrative style I liked so much and combine it with telling stories of small companies—usually bootstrappers or freelancers who have grown their business to be bigger than just themselves.

      That’s how the show was born and it’s been quite a ride. We’re in the middle of Season 6 right now and we’ve had some incredible stories to tell—both with people you’ve heard of before and others who are quietly building businesses that support themselves, their families, their lifestyles and their passions.

    • Congratulations on making six seasons of the show - Freelance to Founder has clearly struck a chord with the podcast-listening community. Do you get responses or messages from listeners letting you know how much the show has inspired them?

    • Thank you so much! It's been a really fun ride for us. The show host, Brandon Hull has been with me for the last 5 seasons and now we've partnered with The Podglomerate which has started a whole new era. It's been a blast.

      To answer your question: Absolutely. We hear from people on twitter (@milloteam) and get e-mails as well. What I love most is when someone tells us they finally had the courage to take the leap into working for themselves or felt inspired to begin working ON their business instead of just IN their business after listening to the show.

    • It's so hard to just pick a few! We've tried really hard to make sure each guest has a story worth telling (and they're not just doing the podcasting circuit in order to sell more books or something).

      There are a few classics that are really fun to listen to. Zooming all the way back to Season 1, I’d recommend our very first episodes—it’s still one of my favorites—with Courtney Brown of My Cents of Style (S1 E1).

      We’ve also had some really action-packed, value-jammed episodes with experts like Brennan Dunn of Double Your Freelancing (S3 E1) and Chris Do from The Futur (S4 E1). Other big names you might recognize include Andrew Warner from Mixergy (S5 E6), Cynthia Johnson from Bell + Ivy (S4 E3) or Author & Freelance Expert Paul Jarvis (S6 E2).

      As a full-time blogger myself I personally really love the blogging episodes including Susie Bulloch of HeyGrillHey (S6 E4) or Courtney Slazinik of Click It Up A Notch (S5 E5).

      See... I warned you. Ha ha. Hard to pick...

    • You’ve had some really interesting guests, like season 6.4’s episode featuring Susie Bulloch of million-dollar barbeque blog Hey Grill Hey - and one of the questions you asked her was “Why be comfortable?” Is that a question that’s often asked of your guests, pushing themselves to the next level?

    • We actually have a very in-depth process for preparing questions for each of our guests. One thing we wanted to get away from was the more scripted interview approach to business podcasts that we were seeing (and continue to see) everywhere else.

      There may be a few questions we repeat when needed, but we try to steer clear of a prescribed set of questions when we talk with our guests.

      It's one of a few ways we're trying to stand out from so many other business interview shows. I think it's helping.

    • Each path is definitely unique, but the more stories we tell, the more we find common threads. These aren’t big secrets either. Successful entrepreneurs—including the ones we talk to—tend to take calculated risks, work extremely hard, pivot when something goes wrong, learn from their mistakes, listen to their customers and push forward with optimism and passion.

    • Freelancers are lifelong learners, and you hear in various episodes of the podcast the resources that these people are creating to empower and educate others.

      Besides the podcast, what are some of the best resources you’d recommend to freelancers or those who want to learn how to freelance more and maximize their time?

    • Oh, man. can be really hard to narrow it down.

      There are so many incredible resources for freelancers made available today—way more than when I started freelancing over a decade ago. Freelance to Founder is part of a larger blog for freelancers we manage called Millo. At Millo, my team and I try to keep this running list of tools for freelancers updated and accurate with only the best tools we’ve found and used. We also constantly update this list of freelance job sites for freelancers who need to find clients fast.

      In addition to that, I’d recommend you read/watch content from Sean McCabe, Brennan Dunn, and Ryan Robinson, among others. As well as follow companies like AndCo, Freshbooks, and Bonsai for the latest trends and developments in freelancing.

      I also believe accountability is a HUGE factor when you're working for yourself. There are a few communities I'd recommend looking into. For example, we've got a free Facebook Group called Millo Mastermind. There are also a couple Slack communities for freelancers (here and here) I'm a part of that really pay off.

      Of course, there are conversations happening around business and freelancing here on Cake as well that I can't wait to dive into. 😃

    • Well, as I mentioned, we've been running Millo for 10 years (celebrating 10 years this month actually!) So, over that time we've made a lot of really great connections.

      But in addition to our own network, we also try to listen to other podcasts, read lots of content online, and pay attention to who freelancers/solopreneurs are talking about. Then we'll just reach out and ask if there's any interest. We get a pretty positive response—and it seems to get a bit easier the more you've had more notable people on the show.

      Also, our partnership with the Podglmerate has connected us with some cool people and helped us grow which improves visibility and our ability to find cool stories.

      We do try to focus on a mix of well-known guests and guests without a large following or reputation since our goal is also to provide realistic inspiration as well. There are thousands of people running really cool small businesses—but they don't bother to build a personal brand online.

      I love it when we find those folks.

    • In the case of Paul Jarvis’ episode 6.2 of this most recent season, I was reminded of Elaine Pofeldt’s book “The Million-Dollar, One Person Business” - his story is such an extraordinary one, and Paul’s even written his own book, Company of One! He didn’t want a byproduct of success to be growth - he wanted to continue to freelance without the desire to grow. Is that a common wish for freelancers, and if so, why do you think that is?

    • Yes. I've read Paul's book and it's absolutely amazing. A must-read for anyone who is their own boss.

      Honestly, I've seen both sides of the aisle on this one. There are lots of freelancers who simply enjoy the work they do and don't want to be ordered around by someone else. Writers, designers, consultants, marketers, etc etc. The list goes on forever. These people are most content when they're working in their business. When they're doing the work that pays the bills, so to speak. Their perfect-world scenario is to design or write or whatever day in and day out.

      Then there are freelancers who start off thinking they want to spend all their time designing, marketing, writing, illustrating. After a while, they realize they enjoy building their business as much as (or more than) they enjoy doing the actual work of their business. These freelancers tend to hire more quickly and build systems into their freelance businesses.

      We'll soon have Brian Casel on the show who talks about about systems and processes that allow freelancers to "productize" their businesses and remove themselves from it almost completely.

      Both Brian and Paul are entrepreneurs who I admire colossally. Neither approach is necessarily better than the other. Each one simply satisfies the wishes of the person who's building it.

      My belief is, regardless of what kind of work you do, you should be able to build a business that makes you happy. There are as many different ways to do that as there are entrepreneurs on this planet.

    • For episode 6.1, with AWeber’s Tom Kulzer, he discusses how email was beginning to emerge as a communication platform and how he saw an opportunity there. Identifying unique opportunities seems to be one of the universal constants among the amazing guests on Freelance to Founder! Would you have some advice on getting started with looking for your niche?

    • Sure thing. One of my favorite authors of all time is Chris Guillebeau. In his book, The $100 Startup, he shows this diagram (below). He stresses the importance of finding convergence between what you love to do and what people actually need.

      If you love to eat pizza so you decide to be a freelance pizza eater, it probably won't work out since there are very few people who are looking to hire a contractor who can regularly eat their pizza.

      But if you love to write and you see there's a need for freelance electrical engineers, you'll hate yourself for only catering to the market.

      As per Chris's advice: find the convergence. It's where you'll thrive.

    • With Chelsea Baldwin on episode 6.3 sharing how she started as a world traveler, getting “hooked on the expatriate life” - that seems like a popular lifestyle for freelancers. Do you find that the Freelance to Founder podcast resonates with the international community?

    • Yes, definitely. Overall our listenership on the podcast and our readership on the blog are quite a diverse group geographically. With only about 50% of them actually accessing our content from the U.S. With the growing demand for less expensive labor and growing resources like Fiverr and UpWork, we're also seeing a lot more freelancers in developing countries around the world take advantage of the availability of freelance work. It's an incredible time!

    • We've got a few great episodes left. Today we released an episode with AJ Harbinger who co-founded the Art of Charm and has brought in millions in revenue primarily through podcasting as a lead generation tool.

      We've also got my friend Pam Capalad who's building a quick-growing company called 'Brunch & Budget' plus the episode I mentioned with Brian Casel and more that I won't spoil. ;)

      You can stay updated on iTunes, on our website (get email updates), or wherever you listen to podcasts.

      And if you anyone reading has any recommendations for future season guests, I'd love to hear your ideas too!

    • Thanks for having me! It's been a real blast.

      If you enter your email on this page or subscribe in your fav podcast player, we'll be sure to update you every time we publish a new episode of Freelance to Founder.

      Otherwise, you can subscribe to our blog here and we'll send you insanely helpful business tips every week from contributing experts. For example, inspired by my 10-year anniversary as a blogger, I wrote up 16,000+ words on how to start a blog that actually makes money. We're experimenting this year with way more long-from content like that and finding it's really helping people a lot.

      I'd love to connect more here on Cake or you can find me on twitter too.

      Thanks again! All the best.