entrepreneur Podcast Episodes

Discover the collection of The Work Item podcast episodes with the entrepreneur tag. Go to the Episodes page to listen to the latest releases, find interesting guests, or navigate through the history of the show.

#85 - Building A Business From Python Expertise - Michael Kennedy (Founder, Talk Python Training)

November 14, 2024

If you are listening to this show, you have likely heard of a programming language called Python. And if you are a Python developer, you've likely heard of a podcast dedicated to this programming language - Talk Python To Me. It was started by none other than Michael Kennedy, a Python Software Foundation fellow who managed to turn his expertise into a viable bootstrapped business. In this show, we talk about ways to plan a training business from scratch, what tactics worked best to grow a podcast audience, and how to make sure that you have a viable idea before you quit your day job.

#84 - Tools Do Not Matter - Jason Lengstorf (Founder, Learn With Jason)

October 31, 2024

If you've been immersed in the tech world for some time, you probably have heard one specific YouTube channel mentioned more than once - Learn With Jason. It's a project started by Jason Lengstorf, a former VP of developer experience at a web tooling startup (he was a head of developer relations prior to that too), that is aimed at helping everyone navigate the always changing landscape of developer tools and frameworks. Which, by the way, according to Jason do not matter.

#82 - Stop Building SaaS Landing Pages - Craig Hewitt (Founder, Castos)

July 12, 2024

Craig Hewitt, the founder of the podcasting platform Castos, comes from generations of entrepreneurs, and his own journey builds on the experience and stamina of those that came before him. In this show, we chat about best practices for hiring developers for your bootstrapped startup, finding the right approach to deliver hard news, and how to ensure that your relationships aren't hurt as you embark on the entrepreneurship treadmill.

#80 - Web Development Is Theatre - Miriam Suzanne (CSS Working Group, OddBird)

June 12, 2024

One of the things that Miriam Suzanne realized early in her developer journey is that web development is a tool - she wanted to build a website for her theater company and ended up building a career and a company around it. And not just that, but she also joined the CSS Working Group - the official standards body that determines how the CSS stack evolves. In this show, we talk about her early discovery of the power of the web, how she joins creativity with technical prowess, and how CSS is really like poetry written in the browser.

#74 - Books, Remote Work, and Q&A, with Adrienne Tacke

March 15, 2024

Welcome back to The Work Item. Today we're exploring the ins and outs of remote work, writing, and community engagement with a show veteran, Adrienne Tacke. I'm delighted to welcome Adrienne back to the show, especially considering that since our last recording we received quite a few follow-up questions. Just like last time, Adrienne brings a wealth of knowledge and experience to our discussion, especially when it comes to remote work culture. And today, we're adding a new twist: a dedicated Q&A segment where Adrienne will be addressing your burning questions directly.

#73 - Put The Passion Aside And Go For The Market, with Rob Walling

February 12, 2024

If you’ve ever listened to Startups For The Rest Of Us (which, by the way, is approaching seven hundred episodes), you might already be familiar with the energetic host of the show - entrepreneur, bootstrapper, and podcaster extraordinaire Rob Walling. Rob and I chat about his early days as an employee, the transition from the more traditional path of working for someone to starting his own business, building MicroConf, and how the trifecta of skill, hard work, and luck can help folks be on a more predictable path to success.

#72 - Give People What They Came For, with Jerod Santo

February 5, 2024

Today I got the pleasure to chat with Jerod Santo, the Managing Editor at Changelog Media. Picture this – a podcast that not only uncovers the intricacies of Jerod's career but also shares some unconventional lessons learned from his work. From navigating the ever-evolving tech landscape to spearheading Changelog, Jerod brings a wealth of experience that transcends your typical engineer expectations and taps into the heart of what it means to build a sustainable developer community.

#67 - Building Design Communities, with Grace Ling, UX Designer at Electronic Arts, and Founder of Design Buddies

December 21, 2023

Grace Ling is a UX designer at Electronic Arts and the founder of the Design Buddies, one of the world’s largest design communities.

#64 - Diving Into Industrial Design, with Anson Cheung

December 12, 2023

Anson Cheung worked as an industrial designer with brands like Lyft, Google, Roku, and HunterDouglas. We sat down to learn more about his career.

#62 - Building Sustainable Practices, with Jason Fried

October 23, 2023

Jason Fried is the co-founder and CEO of 37signals, the company behind Basecamp and Hey. I chat with Jason about his path to entrepreneurship, the lack of value in a lot of meetings, and generally building sustainable practices that enable businesses and their employees to thrive.