{"id":47727,"date":"2026-01-26T09:43:08","date_gmt":"2026-01-26T08:43:08","guid":{"rendered":"https:\/\/www.freelancermap.com\/blog\/?p=47727"},"modified":"2026-01-30T12:44:43","modified_gmt":"2026-01-30T11:44:43","slug":"podcast-episode-17-rich-wilson","status":"publish","type":"post","link":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/","title":{"rendered":"Why Enterprises Struggle with Freelancers &#8211; Episode 17 with Rich Wilson"},"content":{"rendered":"\n<p>What\u2019s really stopping enterprises from working with freelancers? Is it trust, process, or simply&#8230; vocabulary?<\/p>\n\n\n\n<p>In a recent episode of <em>The Independent Workforce<\/em>, we sat down with <strong><a href=\"https:\/\/www.linkedin.com\/in\/richlwilson\/\" target=\"_blank\" rel=\"noreferrer noopener\">Rich Wilson<\/a><\/strong>, CEO and Co-Founder of <strong><a href=\"https:\/\/gigged.ai\/\" target=\"_blank\" rel=\"noreferrer noopener\">Gigged.AI<\/a><\/strong>, to talk about the <strong>past, present, and future of freelance collaboration<\/strong> \u2014 especially inside enterprise environments. <\/p>\n\n\n\n<p>Rich is no stranger to the space. From his early days as a recruiter at Allegis Group to advising tech leaders at Gartner, he\u2019s been in the trenches of hiring, contracting, and now, platform building.<\/p>\n\n\n\n<div class=\"wp-block-group has-background\" style=\"background-color:#f5f5f5\"><div class=\"wp-block-group__inner-container is-layout-constrained wp-block-group-is-layout-constrained\">\n<figure class=\"wp-block-embed is-type-video is-provider-spotify wp-block-embed-spotify wp-embed-aspect-16-9 wp-has-aspect-ratio\"><div class=\"wp-block-embed__wrapper\">\n<iframe title=\"Spotify Embed: \ud83e\udd11 How Hiring Contractors Saves You Money And Time | The Independent Workforce | Rich Wilson\" style=\"border-radius: 12px\" width=\"624\" height=\"351\" frameborder=\"0\" allowfullscreen allow=\"autoplay; clipboard-write; encrypted-media; fullscreen; picture-in-picture\" data-src=\"https:\/\/open.spotify.com\/embed\/episode\/7qag8CbeZ1L43j2IheVrBY\/video?utm_source=oembed\" src=\"data:image\/svg+xml;base64,PHN2ZyB3aWR0aD0iMSIgaGVpZ2h0PSIxIiB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciPjwvc3ZnPg==\" class=\"lazyload\" data-load-mode=\"1\"><\/iframe>\n<\/div><\/figure>\n\n\n\n<p class=\"has-text-align-center\"><strong>Enjoyed this episode?<br><\/strong>Subscribe now on <a href=\"https:\/\/www.youtube.com\/@freelancermapinternational6860\" target=\"_blank\" rel=\"noreferrer noopener\">YouTube<\/a>, <a href=\"https:\/\/creators.spotify.com\/pod\/profile\/freelancermap\/\" target=\"_blank\" rel=\"noreferrer noopener\">Spotify<\/a> or <a href=\"https:\/\/podcasts.apple.com\/us\/podcast\/the-independent-workforce\/id1840173073\" target=\"_blank\" rel=\"noreferrer noopener\">Apple Podcast<\/a><\/p>\n\n\n\n<p class=\"has-text-align-center\"><a href=\"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/The-Independent-Workforce-podcast-episode-15-John-Winsor.pdf.pdf\">\ud83d\udce9 Download the full transcript <\/a><a href=\"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/The-Independent-Workforce-podcast-episode-17-Rich-Wilson.pdf\">\ud83d\udce9<\/a><\/p>\n<\/div><\/div>\n\n\n\n<p>What followed was one of the most <strong>raw, real, and practical conversations<\/strong> we\u2019ve had about the shift towards independent work \u2014 and the mindset changes companies need to make if they want to thrive in this new world.<br><\/p>\n\n\n\n<h2 class=\"wp-block-heading\">From Burnout to Blended Talent<\/h2>\n\n\n\n<p>Rich\u2019s journey started in recruitment \u2014 \u201cplugging in Windows XP machines,\u201d as he laughed \u2014 and evolved into building <strong>enterprise-scale contractor programs<\/strong>. But after 12 years, burnout hit hard.<\/p>\n\n\n\n<p>\u201cI was really burned out. I hadn\u2019t spent enough time with my family, and I realized I was running on empty. That\u2019s when I stepped back, got curious about AI and data, and later, joined Gartner.\u201d<\/p>\n\n\n\n<p>It was there that the future became clear. While advising CIOs and tech leaders, <strong>every conversation \u2014 no matter the topic \u2014 eventually came back to one thing: talent<\/strong>.<\/p>\n\n\n\n<p>That\u2019s when the idea for Gigged.AI truly took shape: <strong>a platform designed to help companies fill skill gaps fast<\/strong> \u2014 using internal employees, freelancers, and even AI agents.<\/p>\n\n\n\n<p class=\"has-text-align-center has-text-color has-background has-link-color wp-elements-49ce5c979d98996cda50352e7a8691e1\" style=\"color:#ffffff;background-color:#5202ff\"><strong>Are you an experienced IT freelancer?<\/strong><br>Join our growing network of specialised professionals and access exclusive opportunities with leading companies.<br><a href=\"https:\/\/www.freelancermap.com\/registration?ref=blog-com-podcast-rich-wilson\"><strong>&gt; Create your freelancer profile<\/strong><\/a><\/p>\n\n\n\n<h2 class=\"wp-block-heading\">The Real Barriers Aren\u2019t What You Think<\/h2>\n\n\n\n<p>So, what\u2019s stopping enterprises from hiring more freelancers?<\/p>\n\n\n\n<p>You might think it\u2019s trust. Or quality. Or maybe even budget. But according to Rich, the real reason is <strong>language<\/strong>.<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p>\u201cFreelancer, contractor, consultant \u2014 they all mean different things in enterprise. Not because the work is different, but because the <strong>budget categories<\/strong> are. The moment you say \u2018freelancer,\u2019 it triggers the wrong internal process \u2014 and that\u2019s where things get stuck.\u201d<\/p>\n<\/blockquote>\n\n\n\n<p>In other words, it\u2019s not that companies don\u2019t want to work with independent talent. It\u2019s that they <strong>don\u2019t know how to classify it<\/strong>, which affects how quickly they can buy and move forward.<\/p>\n\n\n\n<p>\u201cIf you want to get through procurement, you have to speak their language. Sometimes just changing one word \u2014 from freelancer to consultant \u2014 gets the deal moving.\u201d<\/p>\n\n\n\n<h2 class=\"wp-block-heading\">Don\u2019t Compete with Agencies. Compete with Inefficiency.<\/h2>\n\n\n\n<p>Gigged.AI\u2019s strategy has evolved over the years \u2014 moving away from chasing high-volume gigs to focusing on <strong>high-value, enterprise-scale projects<\/strong>.<\/p>\n\n\n\n<p>\u201cWe\u2019re not trying to be the next Fiverr or Upwork. We\u2019re focused on quality, not quantity. Fewer gigs, but with real impact.\u201d<\/p>\n\n\n\n<p>This shift required not only a change in sales strategy but a <strong>repositioning of their competition<\/strong>. Gigged.AI doesn\u2019t aim to replace recruiters. In fact, Rich believes <strong>recruiters are more important than ever<\/strong> \u2014 just not in the traditional sense.<\/p>\n\n\n\n<blockquote class=\"wp-block-quote is-layout-flow wp-block-quote-is-layout-flow\">\n<p>\u201cThe recruiter role is evolving. It\u2019s less about sourcing and more about managing relationships \u2014 becoming that trusted advisor who ensures everything runs smoothly.\u201d<\/p>\n<\/blockquote>\n\n\n\n<p>Instead of competing with platforms or agencies, Rich set his sights on a different target:<\/p>\n\n\n\n<p>\u201cWe started competing with large consulting firms \u2014 the ones charging $2,000 a day for work that an independent expert can do just as well, if not better, for a third of the price.\u201d<\/p>\n\n\n\n<p class=\"has-text-align-center has-text-color has-background has-link-color wp-elements-ae5c9923ce795c9093c10db1657685f6\" style=\"color:#ffffff;background-color:#5202ff\"><strong>Looking to hire specialised IT talent quickly?<\/strong><br>Browse <a href=\"https:\/\/www.freelancermap.com\/freelancers-directory.html\">70,000+ freelancers<\/a> or build a flexible global workforce.<br><a href=\"https:\/\/www.freelancermap.com\/registration?ref=blog-com-podcast-rich-wilson\"><strong>&gt; Get started as a company<\/strong><\/a><\/p>\n\n\n\n<h2 class=\"wp-block-heading\">Why Freelancers Still Get Overlooked<\/h2>\n\n\n\n<p>Despite the demand for skills, many highly experienced freelancers still get overlooked in enterprise hiring. Why? It comes down to <strong>trust and perception<\/strong>.<\/p>\n\n\n\n<p>\u201cThe funny thing is, most of the time, those big-name consultants companies hire aren\u2019t even full-time employees. They\u2019re independent too \u2014 just hidden behind a brand.\u201d<\/p>\n\n\n\n<p>But when freelancers build their own brand? That changes everything.<\/p>\n\n\n\n<p>\u201cYou\u2019re not just a freelancer \u2014 you\u2019re a business now. You need to talk about the value you bring, share your wins, and make it easy for companies to say yes.\u201d<\/p>\n\n\n\n<h2 class=\"wp-block-heading\">Building the \u201cBlended\u201d Workforce<\/h2>\n\n\n\n<p>So what\u2019s the endgame?<\/p>\n\n\n\n<p>Rich envisions a future where <strong>internal employees, external freelancers, and AI agents<\/strong> all sit within the same workflow \u2014 matched seamlessly to projects based on skills, not job titles.<\/p>\n\n\n\n<p>\u201cThe tech exists. The blocker isn\u2019t the software. It\u2019s the change management. It\u2019s helping people adopt a new way of working while they\u2019re already running 100 miles an hour.\u201d<\/p>\n\n\n\n<p>That\u2019s why Rich focuses on building <strong>small, focused pilots<\/strong> with departments like data or AI \u2014 places where skill gaps are clear and urgency is high. Once that proof of concept is successful, expansion comes naturally.<br><\/p>\n\n\n\n<h2 class=\"wp-block-heading\">Final Advice from Rich<\/h2>\n\n\n\n<p>For <strong>companies<\/strong>:<br>\u201cBe open to new models. You don\u2019t need to choose between recruitment agencies or consultancies. There are new options out there \u2014 flexible, fast, and just as reliable.\u201d<\/p>\n\n\n\n<p>For <strong>freelancers<\/strong>:<br>\u201cYou can\u2019t hide anymore. Build your brand. Post your project wins. Show people what you\u2019ve done and how you can help. That\u2019s how you get work now.\u201d<\/p>\n\n\n\n<p>Want to learn more or connect with Rich?<br>He\u2019s most active on LinkedIn \u2014 <a href=\"https:\/\/www.linkedin.com\/in\/richlwilson\/\" target=\"_blank\" rel=\"noreferrer noopener\">drop him a message<\/a>, he\u2019ll reply (eventually).<\/p>\n\n\n\n<p>Catch the full episode of <em>The Independent Workforce<\/em> with Rich Wilson on <a href=\"https:\/\/open.spotify.com\/episode\/7qag8CbeZ1L43j2IheVrBY\">Spotify<\/a>, <a href=\"https:\/\/www.youtube.com\/watch?v=nkYyRwLQ7fw\">YouTube<\/a>, or wherever you get your podcasts. And if you enjoyed it, remember to subscribe and share!<\/p>\n\n\n\n<p>The future of work isn\u2019t coming \u2014 it\u2019s already here. The real question is: Are you ready to work differently?<\/p>\n\n\n\n<figure class=\"wp-block-image size-full\"><a href=\"https:\/\/www.freelancermap.com\/registration?ref=blog-com-podcast-rich-wilson\"><img decoding=\"async\" width=\"1024\" height=\"300\" data-src=\"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2025\/10\/build-flexible-teams-with-freelancers.png\" alt=\"Build flexible teams with top freelancers. Sign up to freelancermap now\" class=\"wp-image-47322 lazyload\" data-srcset=\"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2025\/10\/build-flexible-teams-with-freelancers.png 1024w, https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2025\/10\/build-flexible-teams-with-freelancers-300x88.png 300w, https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2025\/10\/build-flexible-teams-with-freelancers-768x225.png 768w, https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2025\/10\/build-flexible-teams-with-freelancers-720x211.png 720w, https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2025\/10\/build-flexible-teams-with-freelancers-580x170.png 580w, https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2025\/10\/build-flexible-teams-with-freelancers-320x94.png 320w\" data-sizes=\"(max-width: 1024px) 100vw, 1024px\" src=\"data:image\/svg+xml;base64,PHN2ZyB3aWR0aD0iMSIgaGVpZ2h0PSIxIiB4bWxucz0iaHR0cDovL3d3dy53My5vcmcvMjAwMC9zdmciPjwvc3ZnPg==\" style=\"--smush-placeholder-width: 1024px; --smush-placeholder-aspect-ratio: 1024\/300;\" \/><\/a><\/figure>\n","protected":false},"excerpt":{"rendered":"<p>What\u2019s really stopping enterprises from working with freelancers? Is it trust, process, or simply&#8230; vocabulary? In a recent episode of The Independent Workforce, we sat down with Rich Wilson, CEO and Co-Founder of Gigged.AI, to talk about the past, present, and future of freelance collaboration \u2014 especially inside enterprise environments. Rich is no stranger to [&hellip;]<\/p>\n","protected":false},"author":3120,"featured_media":47736,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_kad_blocks_custom_css":"","_kad_blocks_head_custom_js":"","_kad_blocks_body_custom_js":"","_kad_blocks_footer_custom_js":"","footnotes":""},"categories":[3008,4189],"tags":[],"class_list":["post-47727","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-news","category-podcast"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v23.4 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Why Enterprises Struggle with Freelancers | TIW Podcast<\/title>\n<meta name=\"description\" content=\"What\u2019s really stopping enterprises from working with freelancers? Is it trust, process, or simply vocabulary? Expert Rich Wilson clears it up.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Why Enterprises Struggle with Freelancers | TIW Podcast\" \/>\n<meta property=\"og:description\" content=\"What\u2019s really stopping enterprises from working with freelancers? Is it trust, process, or simply vocabulary? Expert Rich Wilson clears it up.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/\" \/>\n<meta property=\"og:site_name\" content=\"Freelancer Blog\" \/>\n<meta property=\"article:publisher\" content=\"https:\/\/www.facebook.com\/freelancermapInternational\/\" \/>\n<meta property=\"article:published_time\" content=\"2026-01-26T08:43:08+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2026-01-30T11:44:43+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/youtube-rich-wilson-contractors-vs-big-consulting.jpg\" \/>\n\t<meta property=\"og:image:width\" content=\"1280\" \/>\n\t<meta property=\"og:image:height\" content=\"720\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/jpeg\" \/>\n<meta name=\"author\" content=\"Stefania Volpe\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:creator\" content=\"@freelancer_INT\" \/>\n<meta name=\"twitter:site\" content=\"@freelancer_INT\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"Stefania Volpe\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"5 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#article\",\"isPartOf\":{\"@id\":\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/\"},\"author\":{\"name\":\"Stefania Volpe\",\"@id\":\"https:\/\/www.freelancermap.com\/blog\/#\/schema\/person\/efa89a55da25a71300f23186650f8a11\"},\"headline\":\"Why Enterprises Struggle with Freelancers &#8211; Episode 17 with Rich Wilson\",\"datePublished\":\"2026-01-26T08:43:08+00:00\",\"dateModified\":\"2026-01-30T11:44:43+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/\"},\"wordCount\":978,\"commentCount\":0,\"publisher\":{\"@id\":\"https:\/\/www.freelancermap.com\/blog\/#organization\"},\"image\":{\"@id\":\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#primaryimage\"},\"thumbnailUrl\":\"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/youtube-rich-wilson-contractors-vs-big-consulting.jpg\",\"articleSection\":[\"News\",\"Podcast\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/\",\"url\":\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/\",\"name\":\"Why Enterprises Struggle with Freelancers | TIW Podcast\",\"isPartOf\":{\"@id\":\"https:\/\/www.freelancermap.com\/blog\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#primaryimage\"},\"image\":{\"@id\":\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#primaryimage\"},\"thumbnailUrl\":\"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/youtube-rich-wilson-contractors-vs-big-consulting.jpg\",\"datePublished\":\"2026-01-26T08:43:08+00:00\",\"dateModified\":\"2026-01-30T11:44:43+00:00\",\"description\":\"What\u2019s really stopping enterprises from working with freelancers? Is it trust, process, or simply vocabulary? Expert Rich Wilson clears it up.\",\"breadcrumb\":{\"@id\":\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#breadcrumb\"},\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/\"]}]},{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#primaryimage\",\"url\":\"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/youtube-rich-wilson-contractors-vs-big-consulting.jpg\",\"contentUrl\":\"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/youtube-rich-wilson-contractors-vs-big-consulting.jpg\",\"width\":1280,\"height\":720},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"Home\",\"item\":\"https:\/\/www.freelancermap.com\/blog\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Why Enterprises Struggle with Freelancers &#8211; Episode 17 with Rich Wilson\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\/\/www.freelancermap.com\/blog\/#website\",\"url\":\"https:\/\/www.freelancermap.com\/blog\/\",\"name\":\"Freelancer Blog\",\"description\":\"Tips &amp; Practical Advice for Freelancers and IT professionals\",\"publisher\":{\"@id\":\"https:\/\/www.freelancermap.com\/blog\/#organization\"},\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\/\/www.freelancermap.com\/blog\/?s={search_term_string}\"},\"query-input\":{\"@type\":\"PropertyValueSpecification\",\"valueRequired\":true,\"valueName\":\"search_term_string\"}}],\"inLanguage\":\"en-US\"},{\"@type\":\"Organization\",\"@id\":\"https:\/\/www.freelancermap.com\/blog\/#organization\",\"name\":\"freelancermap.com\",\"url\":\"https:\/\/www.freelancermap.com\/blog\/\",\"logo\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\/\/www.freelancermap.com\/blog\/#\/schema\/logo\/image\/\",\"url\":\"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2025\/02\/freelancermap-black-logo@4x.png\",\"contentUrl\":\"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2025\/02\/freelancermap-black-logo@4x.png\",\"width\":1044,\"height\":145,\"caption\":\"freelancermap.com\"},\"image\":{\"@id\":\"https:\/\/www.freelancermap.com\/blog\/#\/schema\/logo\/image\/\"},\"sameAs\":[\"https:\/\/www.facebook.com\/freelancermapInternational\/\",\"https:\/\/x.com\/freelancer_INT\",\"https:\/\/www.linkedin.com\/company\/freelancermap-gmbh\/\",\"https:\/\/www.instagram.com\/freelancermap_int\/\"]},{\"@type\":\"Person\",\"@id\":\"https:\/\/www.freelancermap.com\/blog\/#\/schema\/person\/efa89a55da25a71300f23186650f8a11\",\"name\":\"Stefania Volpe\",\"image\":{\"@type\":\"ImageObject\",\"inLanguage\":\"en-US\",\"@id\":\"https:\/\/www.freelancermap.com\/blog\/#\/schema\/person\/image\/\",\"url\":\"https:\/\/secure.gravatar.com\/avatar\/2e79925dc33f03350c0b2316f3925a82?s=96&d=mm&r=g\",\"contentUrl\":\"https:\/\/secure.gravatar.com\/avatar\/2e79925dc33f03350c0b2316f3925a82?s=96&d=mm&r=g\",\"caption\":\"Stefania Volpe\"},\"description\":\"Stefania joined the international team at freelancermap in 2020. She loves marketing, the digital world, foreign languages and meeting different cultures. She moved from Italy to Germany thanks to an exchange program at the university and worked as marketing manager for several startups. Now she focuses on helping freelancers and IT professionals to find jobs and clients worldwide at www.freelancermap.com.\",\"sameAs\":[\"https:\/\/www.freelancermap.com\/\",\"https:\/\/www.linkedin.com\/in\/stefaniavolpe\/\"],\"url\":\"https:\/\/www.freelancermap.com\/blog\/author\/stefania-volpe\/\"}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Why Enterprises Struggle with Freelancers | TIW Podcast","description":"What\u2019s really stopping enterprises from working with freelancers? Is it trust, process, or simply vocabulary? Expert Rich Wilson clears it up.","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/","og_locale":"en_US","og_type":"article","og_title":"Why Enterprises Struggle with Freelancers | TIW Podcast","og_description":"What\u2019s really stopping enterprises from working with freelancers? Is it trust, process, or simply vocabulary? Expert Rich Wilson clears it up.","og_url":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/","og_site_name":"Freelancer Blog","article_publisher":"https:\/\/www.facebook.com\/freelancermapInternational\/","article_published_time":"2026-01-26T08:43:08+00:00","article_modified_time":"2026-01-30T11:44:43+00:00","og_image":[{"width":1280,"height":720,"url":"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/youtube-rich-wilson-contractors-vs-big-consulting.jpg","type":"image\/jpeg"}],"author":"Stefania Volpe","twitter_card":"summary_large_image","twitter_creator":"@freelancer_INT","twitter_site":"@freelancer_INT","twitter_misc":{"Written by":"Stefania Volpe","Est. reading time":"5 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"Article","@id":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#article","isPartOf":{"@id":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/"},"author":{"name":"Stefania Volpe","@id":"https:\/\/www.freelancermap.com\/blog\/#\/schema\/person\/efa89a55da25a71300f23186650f8a11"},"headline":"Why Enterprises Struggle with Freelancers &#8211; Episode 17 with Rich Wilson","datePublished":"2026-01-26T08:43:08+00:00","dateModified":"2026-01-30T11:44:43+00:00","mainEntityOfPage":{"@id":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/"},"wordCount":978,"commentCount":0,"publisher":{"@id":"https:\/\/www.freelancermap.com\/blog\/#organization"},"image":{"@id":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#primaryimage"},"thumbnailUrl":"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/youtube-rich-wilson-contractors-vs-big-consulting.jpg","articleSection":["News","Podcast"],"inLanguage":"en-US","potentialAction":[{"@type":"CommentAction","name":"Comment","target":["https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#respond"]}]},{"@type":"WebPage","@id":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/","url":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/","name":"Why Enterprises Struggle with Freelancers | TIW Podcast","isPartOf":{"@id":"https:\/\/www.freelancermap.com\/blog\/#website"},"primaryImageOfPage":{"@id":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#primaryimage"},"image":{"@id":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#primaryimage"},"thumbnailUrl":"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/youtube-rich-wilson-contractors-vs-big-consulting.jpg","datePublished":"2026-01-26T08:43:08+00:00","dateModified":"2026-01-30T11:44:43+00:00","description":"What\u2019s really stopping enterprises from working with freelancers? Is it trust, process, or simply vocabulary? Expert Rich Wilson clears it up.","breadcrumb":{"@id":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#breadcrumb"},"inLanguage":"en-US","potentialAction":[{"@type":"ReadAction","target":["https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/"]}]},{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#primaryimage","url":"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/youtube-rich-wilson-contractors-vs-big-consulting.jpg","contentUrl":"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/youtube-rich-wilson-contractors-vs-big-consulting.jpg","width":1280,"height":720},{"@type":"BreadcrumbList","@id":"https:\/\/www.freelancermap.com\/blog\/podcast-episode-17-rich-wilson\/#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/www.freelancermap.com\/blog\/"},{"@type":"ListItem","position":2,"name":"Why Enterprises Struggle with Freelancers &#8211; Episode 17 with Rich Wilson"}]},{"@type":"WebSite","@id":"https:\/\/www.freelancermap.com\/blog\/#website","url":"https:\/\/www.freelancermap.com\/blog\/","name":"Freelancer Blog","description":"Tips &amp; Practical Advice for Freelancers and IT professionals","publisher":{"@id":"https:\/\/www.freelancermap.com\/blog\/#organization"},"potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/www.freelancermap.com\/blog\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"en-US"},{"@type":"Organization","@id":"https:\/\/www.freelancermap.com\/blog\/#organization","name":"freelancermap.com","url":"https:\/\/www.freelancermap.com\/blog\/","logo":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.freelancermap.com\/blog\/#\/schema\/logo\/image\/","url":"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2025\/02\/freelancermap-black-logo@4x.png","contentUrl":"https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2025\/02\/freelancermap-black-logo@4x.png","width":1044,"height":145,"caption":"freelancermap.com"},"image":{"@id":"https:\/\/www.freelancermap.com\/blog\/#\/schema\/logo\/image\/"},"sameAs":["https:\/\/www.facebook.com\/freelancermapInternational\/","https:\/\/x.com\/freelancer_INT","https:\/\/www.linkedin.com\/company\/freelancermap-gmbh\/","https:\/\/www.instagram.com\/freelancermap_int\/"]},{"@type":"Person","@id":"https:\/\/www.freelancermap.com\/blog\/#\/schema\/person\/efa89a55da25a71300f23186650f8a11","name":"Stefania Volpe","image":{"@type":"ImageObject","inLanguage":"en-US","@id":"https:\/\/www.freelancermap.com\/blog\/#\/schema\/person\/image\/","url":"https:\/\/secure.gravatar.com\/avatar\/2e79925dc33f03350c0b2316f3925a82?s=96&d=mm&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/2e79925dc33f03350c0b2316f3925a82?s=96&d=mm&r=g","caption":"Stefania Volpe"},"description":"Stefania joined the international team at freelancermap in 2020. She loves marketing, the digital world, foreign languages and meeting different cultures. She moved from Italy to Germany thanks to an exchange program at the university and worked as marketing manager for several startups. Now she focuses on helping freelancers and IT professionals to find jobs and clients worldwide at www.freelancermap.com.","sameAs":["https:\/\/www.freelancermap.com\/","https:\/\/www.linkedin.com\/in\/stefaniavolpe\/"],"url":"https:\/\/www.freelancermap.com\/blog\/author\/stefania-volpe\/"}]}},"taxonomy_info":{"category":[{"value":3008,"label":"News"},{"value":4189,"label":"Podcast"}]},"featured_image_src_large":["https:\/\/www.freelancermap.com\/blog\/wp-content\/uploads\/2026\/01\/youtube-rich-wilson-contractors-vs-big-consulting-1024x576.jpg",720,405,true],"author_info":{"display_name":"Stefania Volpe","author_link":"https:\/\/www.freelancermap.com\/blog\/author\/stefania-volpe\/"},"comment_info":0,"category_info":[{"term_id":3008,"name":"News","slug":"news","term_group":0,"term_taxonomy_id":3008,"taxonomy":"category","description":"<span data-sheets-value=\"{&quot;1&quot;:2,&quot;2&quot;:&quot;News about the freelancer industry, the IT freelancer market, events and about freelancermap GmbH&quot;}\" data-sheets-userformat=\"{&quot;2&quot;:4865,&quot;3&quot;:{&quot;1&quot;:0},&quot;11&quot;:4,&quot;12&quot;:0,&quot;15&quot;:&quot;Roboto&quot;}\">News about the freelancer industry, the IT freelancer market, events and about freelancermap GmbH<\/span>","parent":0,"count":39,"filter":"raw","cat_ID":3008,"category_count":39,"category_description":"<span data-sheets-value=\"{&quot;1&quot;:2,&quot;2&quot;:&quot;News about the freelancer industry, the IT freelancer market, events and about freelancermap GmbH&quot;}\" data-sheets-userformat=\"{&quot;2&quot;:4865,&quot;3&quot;:{&quot;1&quot;:0},&quot;11&quot;:4,&quot;12&quot;:0,&quot;15&quot;:&quot;Roboto&quot;}\">News about the freelancer industry, the IT freelancer market, events and about freelancermap GmbH<\/span>","cat_name":"News","category_nicename":"news","category_parent":0},{"term_id":4189,"name":"Podcast","slug":"podcast","term_group":0,"term_taxonomy_id":4189,"taxonomy":"category","description":"The Independent Workforce by freelancermap - a podcast where we speak with CEOs, recruiters and industry leaders to learn how they work with independent talent: the wins, the challenges, and the lessons learned!","parent":0,"count":25,"filter":"raw","cat_ID":4189,"category_count":25,"category_description":"The Independent Workforce by freelancermap - a podcast where we speak with CEOs, recruiters and industry leaders to learn how they work with independent talent: the wins, the challenges, and the lessons learned!","cat_name":"Podcast","category_nicename":"podcast","category_parent":0}],"tag_info":false,"_links":{"self":[{"href":"https:\/\/www.freelancermap.com\/blog\/wp-json\/wp\/v2\/posts\/47727"}],"collection":[{"href":"https:\/\/www.freelancermap.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.freelancermap.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.freelancermap.com\/blog\/wp-json\/wp\/v2\/users\/3120"}],"replies":[{"embeddable":true,"href":"https:\/\/www.freelancermap.com\/blog\/wp-json\/wp\/v2\/comments?post=47727"}],"version-history":[{"count":9,"href":"https:\/\/www.freelancermap.com\/blog\/wp-json\/wp\/v2\/posts\/47727\/revisions"}],"predecessor-version":[{"id":47739,"href":"https:\/\/www.freelancermap.com\/blog\/wp-json\/wp\/v2\/posts\/47727\/revisions\/47739"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.freelancermap.com\/blog\/wp-json\/wp\/v2\/media\/47736"}],"wp:attachment":[{"href":"https:\/\/www.freelancermap.com\/blog\/wp-json\/wp\/v2\/media?parent=47727"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.freelancermap.com\/blog\/wp-json\/wp\/v2\/categories?post=47727"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.freelancermap.com\/blog\/wp-json\/wp\/v2\/tags?post=47727"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}