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The Business of Freelancing
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The Business of Freelancing

Author: Panel: Reuven, Margaret, Kai, Meg, Jeremy, Erik

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If you're a freelancer, then you're not just an expert in your field. You're also a business owner, responsible for everything from bookkeeping to marketing to customer satisfaction to business development.

On the Business of Freelancing, our panel of experienced freelancers discuss the issues that they have encountered while building up their business — and give you practical, actionable advice to take your career to the next level. We also invite expert guests to provide their opinions and perspectives on how you can better succeed in your freelance career.
37 Episodes
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In our final episode, our panel talks about scaling up, whether you should and how to do it:Pros and cons of scalingWhat you can do to prepActionable quick tipsPanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource or something else that they're enjoying & recommend you to check out:Erik: Business Profit 101: A Primer for Freelance Software Developers - DaedTech, The All-In-One People Platform for Payroll, Benefits, HR (gusto.com)Reuven: Workona Tab ManagerNever miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
In this episode, our panel talks about how to improve your career when you're working on your own:Career development for freelancers vs employeesWhat is career development, really?Self-evaluation – taking time to be deliberate about your practicePanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource or something else that they're enjoying & recommend you to check out:Erik: E-Myth Revisited, HS CommunityReuven: Tim Harford’s e-mail adviceNever miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
In this episode, our panel talks about knowing when to fold, knowing when to stop freelancing, and try full-time.:Advantages of a full-time jobHow often should you ask yourself this question/evaluate whether to keep going?Signs that you need to do something differentPanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource or something else that they're enjoying & recommend you to check out:Erik: TropicalMBA, Hit Subscribe CommunityReuven: Live from Pivot MIANever miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
In this episode, our panel will be discussing everything you need to know about handling conflict with clients:Sources of conflictHorror storiesTactical conflict management best practicesAvoiding conflictsPanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource or something else that they're enjoying & recommend you to check out:Erik: The No Asshole Rule (Book)Erik: This guide to measuring web performance.Reuven: Lying for Money (Book)Never miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
In this episode, our panel will be discussing everything you need to know about Customer Service and Client Retention:Why is customer service relevant?UpsellingBest practice & morePanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource or something else that they're enjoying & recommend you to check out:Erik: a free CRM software | Cobra Kai, the show | A Post about Grafana and Prometheus that We Did RecentlyReuven: WeCrashed podcast | Machiavelli for WomenNever miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
In this episode, our panel will be discussing everything you need to know about accounting & finance:What does business finance involve in the early days for a freelancer?Should you pay someone to help?  If so, when, and for what?Taxes, and morePanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource or something else that they're enjoying & recommend you to check out:Erik: FreshBooksErik: This post we did for DevZero about cycle time in agile.Reuven: Bad Blood: Secrets & Lies in a Silicon Valley Startup | The Shrink Next DoorNever miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
In this episode, we will be discussing everything you need to know about pricing with our guest, Jonathan Stark.GuestOur guest this week is Jonathan Stark — He is a former software developer who is on a mission to rid the world of hourly billing. He is the author of Hourly Billing Is Nuts, the host of Ditching Hourly, and writes a daily newsletter on pricing for independent professionals.LinksValue Pricing BootcampHourly Billing Is NutsPanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they're enjoying & recommend you to check out:Thinking in Bets by Annie Duke (Jonathan)Crumbl (Erik)Because Internet by Gretchen McCulloch (Reuven)Never miss an episodeSubscribe wherever you get your podcasts
In this episode, our panel will be discussing everything you need to know about contracts and negotiating over them:When does negotiation begin (in the sales/marketing pipeline)?What is negotiation like with different kinds of companies?What might you negotiate?Dealing with contractsRe-negotiation for future engagementsTips and tricks/best practicesPanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource or something else that they're enjoying & recommend you to check out:Erik: ClickUp, Convolutional Neural NetworksErik: this guide we did for Testim about software testing.Reuven: Anything written by Patrick McKenzie. Check out his website: Kalzumeus Never miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
Once you're done with marketing, how do you actually start the sales funnel with a client? Today, our panel takes a deep dive into everything you need to know about sales.PanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource or something else that they're enjoying & recommend you to check out:Erik: E-Myth, Sales blog post, the practice of BDD.Reuven: You're using your dishwasher wrong, Matt Levine: Bloomberg Opinion ColumnistNever miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
In this episode, our panel takes a deep dive into marketing for freelancers. All your questions will be answered:What is marketing?Where does marketing stop and sales begin?What are the prerequisites for marketing?What do we do for marketing?Best ways for getting started PanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource or something else that they're enjoying & recommend you to check out:Erik: Mario Graphic (scroll down for Mario), my article, managing workflows in SlackReuven: Data Detective (Tim Harford), Twitter advanced search + saved searchNever miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
Episode SummaryWe talk with Philip Morgan, coach & author of 'The Positioning Manual for Indie Consultants', about specialization & positioning - building a defensive advantage around your business by cultivating rare & valuable expertise.LinksPhilip Morgan ConsultingThe Positioning Manual for Indie ConsultantsGuestOur guest this week is Philip Morgan — He helps indie consultants build an expertise moat through experiential learning. He's got a lot of hands-on experience with:Hybrid revenue models that blend digital products with services,Writing and publishing books that have generated in excess of $100,000 in direct revenue,Using publishing to cultivate a strong point of view, expertise, and authoritySmall-scale research.PanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they're enjoying & recommend you to check out:Electric Bike (Philip)HitSubscribe Community (Erik), This Article about User Acceptance Testing (Erik)Beginners: The Joy and Transformative Power of Lifelong Learning (Reuven)Never miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
In this episode, our panel takes a deep dive into preparing your freelance practice and discusses:Their stories of how they got started What they would do differently, and The things to keep in mind when you're actually starting up your practicePanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they're enjoying & recommend you to check out:Books - The Lean Startup, Profit First (Erik)Articles - This article about cycle time in software development (Erik)Keyboard - The CODE Keyboard (Reuven)Never miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
Freelancing 101

Freelancing 101

2022-08-3044:43

Welcome to the first episode of season 3! In this episode, our panel takes a deep dive into freelancing:What does it mean to be a freelancer? Is it for you?PanelistsErik DietrichReuven LernerPanel PicksIn each episode, the panel (and guest) share their picks: a book, app, service, resource or something else that they're enjoying & recommend you to check out:The E-Myth Revisited (Erik)This article about release management in ITIL (Erik)High Conflict: Why We Get Trapped and How We Get Out (Reuven)Never miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
Episode SummaryHow can you grow your business as a freelancer? Our panel discusses the different paths to grow your business, hiring a team, climbing the value chain, and aligning your growth goals with what you want out of your business.PanelistsErik DietrichMarg ReffellKai DavisMeg CumbyPanel PicksEach episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they're enjoying and recommend you check out:JonathanStark.com for insight on pricing, value-pricing, productized services (Erik)Passwordless authentication (Erik)Noko - time tracking software (Kai)Blue Snowball USB Microphone (Meg)The Code Of The Extraordinary Mind by Vishen Lakhiani (Marg)End of Season 2Thanks for listening to this season! This is the last episode of Season 2. We'll be back in January 2021 with Season 3.Never miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
Episode SummaryWe talk with Brian Casel, entrepreneur and creator of ProcessKit and Productize & Scale, about how to create systems that bring order to your business and how to productize your services.LinksProcessKitProductize and ScaleGuestOur guest this week is Brian Casel — an entrepreneur and product designer who has built multiple self-funded businesses since 2008. Brian runs ProcessKit, a process-driven project management software for client services. He's also Productize & Scale, a community where client services founders learn and grow with productized services.PanelistsKai DavisMeg CumbyPanel PicksEach episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they're enjoying and recommend you check out:Guide to new client onboarding (Brian)Smartless - podcast (Brian)Quickbooks Online - Canada; United States; Choose your country (Meg)Audiobooks Norse Mythology and American Gods by Neil Gaiman (Kai)Never miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
Episode SummaryThinking about using YouTube for marketing, promotion and audience growth? Our panel talks about our experiences using this channel and what we'd recommend for people considering adding this channel into the mix for their business.PanelistsMarg ReffellReuven LernerErik DietrichKai DavisPanel PicksEach episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they're enjoying and recommend you check out:Fathom Analytics - an alternative to Google Analytics for people who don't need all the complexity (Reuven)YouTube for Bosses - Course by Sunny Lenarduzzi (Marg)Sunny Lenarduzzi YouTube Channel (Marg)Cathrin Manning YouTube Channel (Marg)TubeBuddy - browser plugin to help you optimize your videos as you upload them (Erik)DaedTech's YouTube channel (Erik)Plutora's YouTube channel about software delivery (Erik)Descript - high-quality AI-powered transcripts (Kai)Never miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
The Elusive Work-Life BalanceEpisode SummaryWe talk about the struggles we face with the ever-present puzzle of balancing work and life as freelancers and indie consultants and the strategies and mindsets we've developed to have some modicum of balance in our lives.PanelistsMeg CumbyJeremy GreenMarg ReffellReuven LernerPanel PicksEach episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they're enjoying and recommend you check out:Taking a walk! (Reuven)Twitter Thread on teaching online (Reuven)Having / picking up new hobbies (Jeremy)Undone (TV series)2-pack 10-Inch Pro FlapJack Studio VILTROX 2000LM Bi-Color LED Studio Edge Round Light with Stand Kit (Marg)Track the habits that help keep you balanced (e.g. in Notion) (Meg)Never miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
Episode SummaryWhere can you find leads in the short term if you're in need of work now? What are strategies you can use to find better quality leads? We answer those questions and share resources to help you on your journey to building leadflow and a sustainable business.Links MentionedThe Brain Audit by Sean D'SouzaGet Clients Now by C. J. HaydenUltimate Sales Machine by Chet HolmesThe Positioning Manual by Philip MorganGet More Leads by Kai DavisFix This Next by Mike MichaelowiczThe One Thing by Gary Keller and Jay PapasanRange by David EpsteinPanelistsKai DavisMarg ReffellMeg CumbyPanel PicksEach episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they're enjoying and recommend you check out:The Brain Audit: Why Clients Buy (and Why They Don't) by Sean D'Souza (Kai)The One Thing (Marg)Freelance Camp (Meg)Never miss an episodeSubscribe wherever you get your podcastsJoin the newsletter
Episode SummaryWe talk with Alex Hillman about lessons for freelancers and indie consultants from his recently released book, the Tiny MBA. Alex drops a lot of wisdom in this episode about how to tackle and unpack some of the issues we face with money psychology, playing the long game of business, and more.Links MentionedTiny MBA30x500Indy HallStacking the BricksGuestThis episode we talk with Alex Hillman. For more than 10 years, Alex and his business partner Amy Hoy have run Stacking the Bricks, where they teach creative people how to bootstrap their own businesses and become sustainably independent. Alex is also the co-founder of Indy Hall, Philadelphia's first coworking space. He's always thinking about the intersection of people, relationships, trust and business. Find Alex on Twitter at https://twitter.com/alexhillmanPanelistsKai DavisMeg CumbyReuven LernerPanel PicksEach episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they're enjoying and recommend you check out:Badass: Making Users Awesome by Kathy Sierra (Meg)How to Get Rich: One of the World's Greatest Entrepreneurs Shares His Secrets by Felix Dennis (Kai)Lulu - online self-publishing and print-on-demand company; Lulu Xpress - their express print-on-demand service (Alex)Land of the Giants podcast (Reuven)Make Me Smart podcast (Reuven)Never miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
Episode SummaryToday we'll be discussing sales and marketing and how to use marketing to improve the sales experience as a freelancer.Links MentionedCold Email PodcastSales 101 for Freelance Devs — Avoiding the Pain You’re About to Experience (Erik Dietrich blog post)PanelistsErik DietrichMeg CumbyMarg ReffellReuven LernerPanel PicksEach episode, the panel (and guest) share their picks: a book, app, service, resource, or something else that they're enjoying and recommend you check out:The 90-Minute Guide to Building Marketing Funnels That Convert by Keith Perhac (Meg)TIL about DevOps at Scale (Erik)Apply to be an author on Hit Subscribe - for people in app dev space (Erik)Flu: The Story of the Great Influenza Pandemic of 1918 and the Search for the Virus That Caused It by Gina Kolata (Reuven)Hunting an Invisible Killer - Science Vs podcast (Reuven)Never miss an episodeSubscribe wherever you get your podcastsJoin the newsletterHelp the showAsk us a questionLeave a review
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