Freelance Cake

Austin L. Church
  • 5.0 (14)
  • ENTREPRENEURSHIP
  • UPDATED BIWEEKLY

This podcast helps ambitious freelancers get better results with less effort. We reveal the specific beliefs, principles, and practices that give you better leverage. Every episode contains no-hype, non-expiring ideas that you can use right away to make the freelance game more profitable and enjoyable.

  1. 5H AGO

    How Josh Cantrell Creates Demand with LinkedIn, Referral Partners, and Better Thinking

    Josh Cantrell didn’t set out with some polished master plan. He got fired. What could have become a long, discouraging detour ended up becoming the first step in building a self-employed career with more ownership, more leverage, and more intention. In this conversation, Josh talks through the evolution of that journey. Early on, he did what many freelancers do. He said yes to whatever paid. Alongside marketing work, he flipped storage units, ran an eBay store, and DJ’d weddings to keep the lights on. Over time, though, he realized he didn’t just need more work. He needed a clearer way to create value. That’s where frameworks entered the picture. Josh shares how discovering StoryBrand gave him a structure he could lean on, not just to do better work, but to explain his reasoning, package stronger offers, and shift client perception. Instead of feeling like he was winging it, he had principles. Instead of selling tasks, he could sell outcomes. We also dig into the mindset shifts that came with experience. Josh talks about moving from scarcity to abundance, from thinking the world was small and stingy to realizing there’s plenty of opportunity out there. He explains how raising his standards changed his behavior, financially and professionally, and why standards often shape results more than motivation does. Another major theme in this episode is relationships. Josh has become increasingly intentional about building what he calls IRPs: ideal referral partners. Rather than relying on random lead gen or posting into the void, he focuses on real conversations with people who already know the kinds of clients he wants to serve. We also talk about LinkedIn, but not in the eye-rolly, “optimize your content funnel” kind of way. Josh uses LinkedIn as a conversation starter. He posts consistently, follows up with people who engage, and looks for chances to turn digital attention into human connection. That approach has led to podcast invites, referral relationships, and new opportunities. And beneath all of it is a simple but important truth: Clarity comes before amplification. If your message is muddy, more marketing just means you’re mumbling into a louder microphone. Josh explains why great content starts with great thinking, and why helping prospects believe the right things may matter just as much as writing the right words. If you want to specialize, strengthen your positioning, create more demand, and build a business with better leverage, this one is worth your time. Key Points Josh started in survival mode. After losing his job in 2017, he pieced together income through freelance marketing, weddings as a DJ, an eBay store, and whatever else kept the lights on.Confidence followed competence. Early “imposter syndrome” had less to do with being broken and more to do with lacking reps, clarity, and proof.Frameworks changed the game. StoryBrand gave Josh a structure for making decisions, justifying recommendations, and packaging higher-value offers.His business evolved slowly but meaningfully. He moved from general marketing services into messaging, positioning, copy, and later more strategic engagements, including fractional CMO-style support.His mindset shifted from scarcity to abundance. Instead of treating every lost client like a verdict on his worth, he learned to see the market as big, generous, and full of opportunity.He now works from standards, not hope. Revenue standards, relationship standards, and service standards all shape how he shows up and how he grows.Ideal referral partners are a major growth lever. Josh aims to build relationships with peers and adjacent experts who already serve the kinds of clients he wants.He treats LinkedIn like a system, not a stage. Post consistently, follow up with engaged people, start real conversations, and see where the thread leads.He’s prioritizing documenting over performing. Lived experience, experiments, humor, and observations from real life make better content than sterile “5 tips” posts.A dream client already believes messaging matters. Josh does best with B2B companies selling something expensive, complex, or confusing that understand clear messaging must come before louder marketing.The deeper opportunity is belief change. Great content does not merely attract attention. It upgrades thinking. It creates demand by putting a fire in people’s minds about better ways to solve old problems.Notable Quotes “Confidence comes as a result of competence.”“If we’re spending money on marketing, but the message isn’t clear, we’re just mumbling into a microphone. We’re just louder.”“When you’re creating demand, it’s about putting a fire in someone’s mind about opportunities and possibilities and new ways to solve old problems.”Resources Mentioned Follow Josh Cantrell on LinkedIn: https://www.linkedin.com/in/joshcanCheck out his website, Signal Brandworks: https://signalbrandworks.com/Join the Freelance Cake Community: https://www.freelancecake.com/community

    55 min

  2. FEB 27

    How Much Is Enough? Fear-Proof Freelancing + Non-Icky LinkedIn DMs with Rachel Bicha

    Should freelancing feel easier by now… or is the hard part kind of the point? In this episode, Austin talks with Rachel Bicha (content strategist + founding Freelance Cake Community member) about building a freelance business that’s sustainable because it’s intentional. Rachel shares how her offline community gives her the psychological safety to do things that scare most freelancers—like DMing interesting people on LinkedIn without feeling weird about it. They unpack the “safety net” Rachel built before going full-time (six months runway, ~50% income on the side, and real boundaries), plus one of her most underrated tools: defining “enough” with minimum and maximum income targets, seasonal goals, and even the occasional sabbatical. You’ll also hear why Rachel’s marketing works: it’s relationship-based, rooted in hospitality and curiosity, and designed to connect with real humans (not “leads”). And yes—print is back. Rachel closes with the whimsical monthly print newsletter she sends out, featuring everything from zines to bingo cards to advent calendars. If you’ve ever struggled with fear, overworking, marketing that feels misaligned, or wondering whether your work actually connects with real humans… this conversation is for you. Key Points Why hard things matter: sometimes friction is the feature — remove it and you remove meaning.Rachel’s path into freelancing: in-house → side freelancing → full-time, plus the mindset shift that made it possible.Managing fear with systems: she waited until she had ~50% of income on the side + six months runway.Defining “enough”: minimum + maximum income targets, seasonal goals, and saying no even when it’s tempting.Avoiding overbooking: tracking time, setting boundaries, and using reflection to notice patterns before they become problems.Relationship-based marketing: hospitality + curiosity beats transactional networking (and feels better, too).LinkedIn outreach that doesn’t feel gross: curious DMs, “owning” the cold pitch, and writing like a real person with real fingerprints.Confidence vs. risk tolerance: Rachel isn’t “confident” — she’s willing to look foolish and survive a flop.Print is back, baby: analog trust, finite media, and why tangibility matters more as the internet gets weirder.Dream client sweet spot: small teams/startups building a repeatable marketing engine through experiments.Notable Quotes “I don’t think I ever really got less scared… I have a lot of systems… that help me feel like things aren’t going to crash and burn.”“I want my marketing to feel like… hospitality… a nice, open, cozy space.”“I would not describe myself as somebody who has a lot of confidence… but I have a high degree of risk tolerance.”Resources Mentioned Follow Rachel on LinkedIn: https://www.linkedin.com/in/rachel-bicha-44080/Check out Rachel’s website: RachOnTheWeb.comSubscribe Rachel’s email newsletter: https://the-creative-side.kit.com/signupSubscribe to Rachel’s print newsletter: https://rachelbicha.notion.site/welcome-to-the-creative-sideJoin the Freelance Cake Community: https://www.freelancecake.com/community

    47 min

  3. JAN 16

    Trust, Verify, and Match Access: Believing People’s Actions with Marc Hyde

    Entrepreneurs love promises. Results come from patterns. Austin and Marc unpack why “actions speak louder than words” is more than homespun wisdom—it’s a working rule for choosing partners, clients, and collaborators without becoming cynical. Expect candid stories (including an investor publicly dressing down his assistant), red flags to watch for, and a dead-simple rubric: Lead with trust. Watch what people do. Match their access with their actions.Key Points Start people at zero, not negative-100. Assume positive intent, then trust but verify.Look for “tells”: delayed follow-ups, ghosted meetings, partial replies to multi-question emails—micro-signals of reliability (or not).Match access to actions: expand access when people keep promises; restrict it when they don’t. No drama required.Finish with integrity: if you’re in a misfit engagement, complete the contracted work cleanly or use a “cancel without cause” clause—then exit.Reset boundaries mid-project (response windows, meeting cadence, content handoffs) to “right the ship.”Automate your judgment with rules (e.g., no tight turnarounds for brand-new clients; no work without deposit). Stick to them.Reliability beats charisma: premium pricing and long-term trust ride on doing what you said, when you said.Self-audit matters: don’t become the person others can’t count on—communicate early, renegotiate timelines, and keep small promises.Notable Quotes “Start everyone at zero—then trust, but verify.”“If they react badly to your rule, they just showed you who they are.”“People will tolerate a lot—except unreliability.”Resources Mentioned Learn more about Marc Hyde: https://marchyde.com/Check out Marc's other website: Christian School WebsitesLearn more about Freelance Cake Community (for advanced freelancers): https://www.freelancecake.com/communityGet 1:1 Strategy Session with Austin: https://www.freelancecake.com/freelance-business-coaching

    55 min

  4. 11/07/2025

    Community as Advantage: How Positive Peer Pressure Fuels Freelance Growth

    Ever rolled your eyes at “You are the company you keep”? Same. But research (and real life) says proximity changes performance. In this solo episode, Austin digs into the research behind peer influence — from Greek philosophers to modern management studies — and shows how freelancers can use positive spillover to their advantage. Learn how intentional community gives solo freelancers leverage: more focus, better systems, smarter strategy, and less burnout. Hear stories from the Freelance Cake Community and learn why joining the right group might be the best business move you make this year. Key Points Positive Spillover is Real: Sitting near a high performer can increase your own performance by 15%.Community as Advantage: When you’re surrounded by people taking action, you’ll find it much harder to stay stuck or spiral into overthinking.Advanced freelancers need peers, not pupils: Once you’ve mastered the basics, you need people who challenge you—not just those asking for your advice.Freelancers can’t rely on osmosis: Without coworkers or office proximity, you have to choose your environment deliberately.Beginner vs. Advanced Needs: Free groups often serve beginners. Paid, private communities curate advanced freelancers who value time, accountability, and quality conversations.Beyond Advice — Real Momentum: The right group saves you from “meta work” (research paralysis) by giving you proven tools and templates so you can act faster.Bias Toward Action: When peers share wins, you’re inspired to take imperfect action too — and that’s how real growth happens.Notable Quotes “You’re in the splash zone, so make sure what you’re getting hit with is motivation, not mediocrity.”“Deliberately create an environment where invisible hands push you onward and upward.”“Who you surround yourself with matters. Your environment matters as much or more than your habits.”“Communities aren’t just about leads — they’re about leverage.”Resources Mentioned Kellogg School of Management Study on Positive SpilloverPhoebe Dodds’ 100 Connections Challenge on SubstackFreelance Cake CommunityCreator Science LabWeb Designer ProIf you’re an advanced freelancer ready to trade burnout for momentum, join a private, paid community that helps you level up faster. Visit freelancecake.com/community to learn more and apply.

    19 min

  5. 10/10/2025

    Growth by Subtraction: Less But Better

    Hitting ~$330K should've felt like a win. Instead, it revealed the real bottleneck: complexity. In this episode, Austin talks about how pruning services, projects, and obligations—less, but better—created the space for saner, more sustainable growth. You’ll get the tomato-plant metaphor (shoutout to Grandmother Martha), insights from Katelyn Bourgoin (“What should you stop doing?”), and even an Apple-style reset moment. Plus, Austin walks through a practical 7-step Subtraction List to help you focus on the work that actually moves the needle.  (Feel free to grab the free worksheet under Resources) What You’ll Learn Why “more” often makes things worseA simple metaphor to decide what to cutHow world-class companies used subtraction to winThe exact 7-step process to simplify your business nowThe 7 Practical Steps Take inventoryFind keepers (money, freedom, satisfaction, impact)Compare results (what to double down on / stop)Cut fluff (Do / Defer / Delegate / Delete + first actions)Make a Don’t List (keep distractions from creeping back)Create rules (avoid default yes—protect your best work)Record decisions (build confidence and course-correct faster)Resources & Links Grab the Subtraction List Worksheet: https://bit.ly/SubtractionListWorksheetApply to the Freelance Cake Community: https://freelancecake.com/communityKatelyn Bourgoin’s Twitter thread on subtraction: https://x.com/KateBour/status/1620795412641718318If this helped you, follow for more systems, strategy, and sanity for advanced freelancers and creators. Chapters 00:00 Hook — when “more” stops working 01:28 The $330K year (and why it didn’t feel like success) 04:22 Complexity: the sneaky saboteur 06:19 Grandma’s garden: prune for higher yield 09:11 What “growth by subtraction” really means 10:33 Focus beats variety (how to choose) 10:59 Example: Katelyn Bourgoin and “do less, better” 13:27 Example: Apple’s 2×2 and 97% cut 15:54 The 7 Steps: Take inventory → Record decisions 24:39 Summary & next steps 26:04 Invitation to the Freelance Cake Community

    28 min

  6. 08/08/2025

    From Slinging Words to Selling Expertise: A 1 on 1 Coaching Case Study with Josh Monen

    What if you feel stuck not because you lack skill but because you’ve snapped on a pair of golden handcuffs? What if you want to go a new direction but can’t afford to lose the retainers you finally stacked up?  This new Freelance Cake episode with Josh Monen is the first one to drop in over 18 months, and I can’t wait for you to check it out. In it, Josh Monen opens up about his transition from senior copywriter who was booked out but working way too much to fractional CMO with productized offers, more time off, and a business closely aligned to the life he wants. Josh didn’t need more clients. He needed different ones. He didn’t need more ideas. He needed a clear roadmap with action steps he could put in his calendar. During our one-on-one coaching engagement, Josh put in the work. Listen to the full conversation. Key Points Booked out, but stuck: Josh was making good money and fully booked, but felt directionless and burnt out. He didn’t need more clients — he needed clarity. Desire for leverage: He wanted to evolve from copywriting into productized services, consulting, and fractional CMO work to create more time freedom. Indecision as the real bottleneck: His core problem wasn’t lack of opportunity — it was overthinking and analysis paralysis. Coaching helped him move from ideas to decisions. Created two scalable offers: Through coaching, Josh developed Funnel Insights and Funnel Blueprint — strategy-first services that led to $30K+ client engagements.From executor to advisor: By leading with strategy and positioning himself as a fractional CMO, Josh changed how clients viewed and engaged him. Lifestyle improvements: He now protects weekends, takes unplugged vacations, and feels more aligned with the freedom-focused business he originally wanted. Real ROI from discomfort: Investing in coaching created “point-of-no-return” momentum and helped him stretch into higher-leverage work. Notable Quotes “I was booked solid with copywriting and making good, consistent income — but more of my thing was like, ‘Where am I going with this?’ I felt like I kind of plateaued and was in maintenance mode.” “If you’re making good money but don’t have time to enjoy it — what’s the point?” “From that very first call, I was blown away. I even told my wife — ‘This guy really listens.’ And that’s rare. That’s one reason I hired you.” Resources Mentioned Book a strategy call with Austin: https://bit.ly/1-on-1-coaching-podAustin Church on How and Why to Sell Strategy Engagements to Your Clients [Ed Gandia podcast]: https://b2blauncher.com/episode267/Josh Links Josh’s podcast, The Way Of Kings: https://podcasts.apple.com/us/podcast/the-way-of-kings/id1743034411Website: www.JoshuaMonen.comX: @JoshMonenListen, rate, and subscribe! For specific beliefs, principles, and practices you can use right away to make the freelance game more profitable and satisfying, subscribe to Freelance Cake podcast on Apple Podcasts or wherever you listen to podcasts!

    35 min

  7. 01/26/2024

    Conversations, Not Confrontations: Learning the Art of Negotiation with Wudan Yan

    In this episode, Austin L. Church talks to journalist, freelance writer, and coach Wudan Yan about the art of negotiation. The driving force behind The Writers' Co-op, Wudan tells the story of her transition from journalism to freelance narrative writing and sheds light on the two different cultures with their sets of norms. Wudan goes on to share how her upbringing and academic background provided very little preparation for the freelance world where negotiation is often necessary.  When teaching freelancers and consultants how to negotiate, Wudan frames back-and-forth as a dialogue or conversation, not a confrontation.  Her personal journey and insights prove that negotiation can be a fulfilling and rewarding aspect of the freelance journey, even if it doesn’t come naturally to you.  If you’ve ever felt uncomfortable during a negotiation or felt like your skills are lacking, you’ll be glad you found this episode.  Key points Wudan’s Journey from Science to Narrative Writing (01:53)Negotiating a raise for the first time (17:44)Wudan's negotiation journey montage (25:37)Negotiating rush projects and rush fees (25:51)The importance of a conversational approach in negotiations (28:43)One simple yet profound tactic to become a master negotiator (36:58)Notable Quotes “You're never going to get what you don't ask for, and you can never get more than the maximum of what you're asking for.""Negotiating is a conversation. If both you and I are setting really hard boundaries around things, there's no meeting in between.""Ask questions that invite a response.”Resources & Links Business Redesign Group Coaching Program$300K Flywheel for Freelancers & ConsultantsThe Writers' Co-opJim Dethmer: Leading Above the LineConnect with Wudan Yan on Instagram and LinkedIn This episode of Freelance Cake is brought to you by CrowdHealth Healthcare in the US is complicated, confusing, and highly personal. Insurance premiums, deductibles, and copays can get really expensive, especially for freelancers and consultants who don’t have an employer paying for anything. Over the last 7 years, my family has saved $60,000+ in premiums, deductibles, and other out-of-pocket medical expenses that we would have paid with our previous insurance policy. Healthcare crowdfunding has been a game changer for us. If you live in the U.S. and you haven’t already explored what CrowdHealth has to offer, take the time to educate yourself. And if you decide you want to give them a try, go to www.joincrowdhealth.com. You can use promo code FREELANCECAKE during sign-up to save $99 per month for 3 months. Listen, rate, and subscribe! For specific beliefs, principles, and practices you can use right away to make the freelance game more profitable and satisfying, subscribe to Freelance Cake podcast on Apple Podcasts or wherever you listen to podcasts!

    48 min

  8. 01/12/2024

    The 4 Stages of Freelancing Explained | Part 2

    In this continuation of “The 4 Stages of Freelancing,” Austin L. Church explores the last two stages: Lifestyler and Diversifier. After they’ve navigated through the Moonlighter and Hustler phases, freelancers reach a level of maturity where challenges become more complex. Meanwhile, opportunities for growth and personal fulfillment expand. Austin highlights the motivations, challenges, mistakes, and questions at each stage, as well as the key breakthroughs and financial goals. Are you a Lifestyler eager to earn the same or more while working less? Or are you a Diversifier interested in creating new revenue streams?  Regardless, this episode will help you figure out where you currently are in your journey and what to focus on next.  Key points Lifestylers overview (01:53)The motivations for Lifestylers (04:35)The mistakes for Lifestylers (05:27)The questions for Lifestylers (07:23)The main breakthrough for Lifestylers (7:56)The main financial goal for Lifestylers (08:16)Diversifiers overview (10:35)The motivations for Diversifiers (12:35)The challenges for Diversifiers (13:49)The questions for Diversifiers (17:07)The main breakthrough for Diversifiers (17:46)The main financial goal for Diversifiers (18:08)Notable Quotes "We freelancers and consultants can get so fixated on winning the next project, staying ahead of bills, and achieving financial stability that we inadvertently become creative workaholics.""The last thing any freelancer should do, any consultant should do is blindly copy someone else."Resources Listen to The 4 Stages of Freelancing Explained | Part 1Read the full post hereBusiness Redesign Group Coaching Program$300K Flywheel for Freelancers & ConsultantsThe Ladders of Wealth Creation: A Step-by-Step Roadmap to Building WealthThis episode of Freelance Cake is brought to you by CrowdHealth Healthcare in the US is complicated, confusing, and highly personal. Insurance premiums, deductibles, and copays can get really expensive, especially for freelancers and consultants who don’t have an employer paying for anything. Over the last 7 years, my family has saved $60,000+ in premiums, deductibles, and other out-of-pocket medical expenses that we would have paid with our previous insurance policy. Healthcare crowdfunding has been a game changer for us. If you live in the U.S. and you haven’t already explored what CrowdHealth has to offer, take the time to educate yourself. And if you decide you want to give them a try, go to www.joincrowdhealth.com. You can use promo code FREELANCECAKE during sign-up to save $99 per month for 3 months. Listen, rate, and subscribe! For specific beliefs, principles, and practices you can use right away to make the freelance game more profitable and satisfying, subscribe to Freelance Cake podcast on Apple Podcasts or wherever you listen to podcasts!

    21 min
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5
out of 5
14 Ratings

About

This podcast helps ambitious freelancers get better results with less effort. We reveal the specific beliefs, principles, and practices that give you better leverage. Every episode contains no-hype, non-expiring ideas that you can use right away to make the freelance game more profitable and enjoyable.

Information

  • Creator
    Austin L. Church
  • Years Active
    2022 - 2026
  • Episodes
    20
  • Rating
    Clean
  • Copyright
    © 2022 Freelance Cake
  • Show Website
    Freelance Cake

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