This is the last episode for 2024. To make it special, it’s a supercut of all the unconventional advice from every single guest that was on the show this year.

#87 - A Wrap-Up Of 2024 Unconventional Career Advice

Today, I'm thrilled to be joined by Asia Orangio, the brain behind DemandMaven, a growth agency dedicated to helping SaaS companies and their founders reach new heights. Asia's unique approach blends data-driven strategies with deep empathy for customers, making her a sought-after expert - from bootstrapped businesses to some of the most established companies.

#86 - The Only Real Way To Know Is To Talk To People - Asia Orangio (CEO, DemandMaven)

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.

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

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.

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

Jennifer Wong is a seasoned engineering manager who started her journey in civil engineering. The fast pace of the tech industry drew her in, and she stuck with it for years since making that call. In this episode, I chat with Jennifer about her transition from a non-traditional career path into software, reasons to take on management instead of being an individual contributor, and why taking the road less traveled in terms of career progression might just be the recipe for long-term growth and success.

#83 - Don't Take The Easy Path - Jennifer Wong (Engineering Leader)

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.

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

In episode 81, Den Delimarsky chats with Kirupa Chinnathambi, a product manager at Google who has built his own personal brand in what is now known as kirupa.com. Kirupa is a talented web developer, designer, writer, and packs so much knowledge in his blog that you can learn how to create great web-based experiences on that content alone.

#81 - Making A Career Out Of A Hobby - Kirupa Chinnathambi (Product Manager - Google)

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.

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

We often talk about promotions and growth, but the moment the conversation shifts towards paths to staff or executive positions, the advice goes blank. There is very little actionable information out there that can tell you how you can get to the highest echelons of leadership. To get a clearer picture on this topic, I sat down with Lena Reinhard, a seasoned executive with an extensive track record at CircleCI, Travis CI, and more.

#79 - How To Get Promoted To Tech Executive - Lena Reinhard (VP Engineering, CircleCI, Travis CI)

One's journey from their early career to working at startups in Silicon Valley can take many forms. Some folks take the more traditional route of joining a company right after college. Others get tired of their corporate life and decide to try something different. Katie Fujihara, an engineer and a technical program manager amalgam, decided that her journey to the heart of "startup land," San Francisco, would be an impromptu one - she just packed up her bags and set out on an adventure.

#78 - I Left Hawai'i To Work In Startups, With Katie Fujihara

For today’s episode, I had the privilege of sitting down with Rachel Andrew, arguably one of the more influential folks in the world of web development. With a career spanning over two decades, Rachel has left an indelible mark on the web developer community. From her groundbreaking work on CSS to her role as co-founder of Perch CMS (she spent 20 years as a freelancer and a business owner), Rachel’s contributions have shaped the way we build and interact with the web.

#77 - Write About The Things You Learned, With Rachel Andrew (Google)

One of the things that is a bit taboo to talk about, both in the tech industry and outside of it is money. People just aren't comfortable discussing openly the hard decisions that go into things like seeking funding, investing money into things that save you time, and scaling your own abilities with the help of, you guessed it, cold, hard, cash. Saron Yitbarek, entrepreneur extraordinaire behind CodeNewbie and podcasts such as Command Line Heroes, generously accepted my invitation to chat and talk about all these things, and more. And of course, we talk about Saron's latest project - Big Cash Money 2024, something for folks that want to max out their income beyond just their salary.

#76 - Be OK Talking About Money, With Saron Yitbarek

In this episode of The Work Item, I had a conversation with David Khourshid, founder of Stately.AI. You might know him as @DavidKPiano on social media. Today, we're breaking new ground around unconventional paths of building an engineering career, entrepreneurship, and leveraging your audience as the potential first customers for your product. And of course - we talk a bit more about state machines (David is also the developer behind XState) and lessons learned from launching and growing a startup in the midst of a pandemic.

#75 - From Pandemic Pastime To Real VC-Funded Startup, with David Khourshid

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.

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

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.

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

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.

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

Kent C. Dodds is a developer, educator, community organizer, and above all, a person that is passionate about making the world a better place by giving as many folks as possible the opportunity to learn web development. I sat down with Kent to chat more about his career, what bootstrapped his interest in programming, and what his takeaways from building his path as an entrepreneur are.

#71 - Going Solo As A Developer Educator, with Kent C. Dodds

Today, you're in for a treat as I sit down with Kenneth Auchenberg, a seasoned product manager - you might know him from his work at Microsoft on Visual Studio Code as well as on developer tools at Stripe. He is also a developer and overall a very nice person to know.

#70 - Building a Career In Developer Tools, with Kenneth Auchenberg

In today's episode, I sat down with Shyvee Shi, a seasoned product leader with a wealth of experience in steering products from conception to market success. Shyvee has been at the forefront of industry trends, contributing significantly to the evolution of product management practices.

#69 - Product Management In The Era Of Generative AI, with Shyvee Shi

In this episode, we're exploring the nuances of executive coaching, demystifying the process and shedding light on how individuals can break through the barriers that often hinder their career growth.

#68 - Why You Need An Executive Coach, with Eric Nehrlich

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

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

Carlos and I dive deep into the product management field, discussing the differences between PM categories, what it means to become the best PM one can be, and what the outlook is for the next five years for those that want to break into the field.

#66 - Becoming The Best Product Manager You Can Be, with the CEO of Product School, Carlos Gonzalez de Villaumbrosia

Learn about finding the balance between your passions and incentives in the tech industry, career seasonality, positive community impact, and recipes on measuring your growth and sustainability.

#65 - Data, Impact, and Sustainability, with Jane Yang

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

#64 - Diving Into Industrial Design, with Anson Cheung

If you want to be intentional about your career and become a multidisciplinary professional, this conversation with Adrienne Tacke is for you.

#63 - Beyond Just Engineering Skills, with Adrienne Braganza Tacke

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.

#62 - Building Sustainable Practices, with Jason Fried

In this episode, I am chatting with Cedric Chin - the founder of the CommonCog blog and business series. You might've read some of Cedric's writing on career moats before.

#61 - Career Moats And Beyond, with Cedric Chin

When we choose our career path, we often try to optimize for one specific bucket - you're a product manager, or a project manager, or a UX designer, or any other variation of an expertise area in tech. Sam Saccone defies the expectations of a single role and instead believes in being a "plumber" - doing whatever work is necessary to enable others to do their own version of great work. I sat down with Sam to learn more about his path to a Senior Staff Engineer at Google, what it means to brute-force your way through problems, and what the best avenues are to become a force multiplier for your team.

#60 - Defining A Force Multiplier, with Sam Saccone

Leaving your full-time job behind and starting your own business based on your own brand is a somewhat scary proposition. And yet, this is exactly what Donny Wals, a prolific iOS developer and technology teacher, is doing. In this episode I sat down with him to talk more about his work, what was his thinking in going solo, and what one needs to learn quickly in an ever-changing technology space.

#59 - Building On Your Own, with iOS Developer Donny Wals

Working on games is hard. It's even harder to go from an engineer to a founder of a game studio that is able to produce two blockbuster titles in a row. In today's show I chat with Moon Studios co-founder Gennadiy Korol about his work on Ori (if you're near an Xbox or a PC - the game is worth your time), learning the complexity of graphics engineering, and navigating the uncertainty that comes from starting a zero-to-one effort where you have nothing to fall back on.

#58 - Becoming a Game Studio Co-Founder, with Moon Studios' Gennadiy Korol

If you are a web developer, chances are that you used CodePen more than once. You're also probably very familiar with CSS-Tricks for, well, more than just CSS tricks. The man behind these experiences, Chris Coyier, actually started his journey some time ago with a programming language called Turbo Pascal - many steps removed from web development. I sat down with Chris to talk more about his career, lessons in getting CodePen out into the world, and so much more.

#57 - From Turbo Pascal to CodePen, with Chris Coyier

If you ever played any of the Halo games, you probably know that there is a _wealth_ of data being exchanged between the game and Halo services. This includes stats and so much more. If you've ever wanted to use those stats, you also probably ran into HaloDotAPI - a Halo API wrapper for Halo Infinite and Master Chief Collection. Behind all of this work is one individual - Alexis, or Zeny_IC (on both Twitter and Xbox Live).

#56 - Reverse Engineering The Halo API with Alexis from HaloDotAPI

What does one need to do to make open-source code more approachable? How do you figure out which teams to join for maximum positive impact on your communities? And how do you build communities? These questions and more are the topic of my conversation with Monica Powell, software engineer extraordinaire, who also happens to be a GitHub Star - an exclusive group of contributors recognized for their outstanding work in the open-source software space!

#55 - Open Source and Web Development, with Monica Powell

Carola Nitz is a seasoned engineer who has been involved in a variety of complex projects - from VLC, to Apple Maps, and now working at Netflix on their iOS app experience. She also started her career by learning medical computer science - what a way to jump in! In this episode, we're learning about her career, what helped her be successful, and how she thinks about the importance of jumps between projects and companies.

#54 - From Apple to Netflix, with Carola Nitz, Sr. Software Engineer at Netflix

There are a few things in your engineering career that you should focus on relentlessly, but few as impactful as finding yourself a guide through the journey, as well as develop a set of complementary skills that can help accelerate your own trajectory. I chatted with Nicole Zhu, Senior Engineer at Vox Media, about the importance of mentorship, peer feedback (or any feedback, for that matter), and how skills that are not directly related to writing code can be more helpful to success than you anticipate.

#53 - Find Your Mentor And Complementary Skills, With Nicole Zhu, Senior Engineer At Vox Media

I don't talk about data science enough on this show. To remedy that, I brought in a remarkable analytics and data science expert - Nick Wan, who is a director of analytics for the Cincinnati Reds. Yes - the baseball team. We chat about his track from academia to working for a sports team, and how to build a career outside your typical FAANG (or is it MANGA) scaffolding.

#52 - Grow Your Career in Data Science, with Nick Wan, Director of Analytics for Cincinnati Reds

Vicente Plata is doing way more than one would expect from an engineering leader - not only is he an engineering manager, but he also advises startups and communities, is deeply involved in various mentorship programs, and is someone who is always eager to help. In this episode we sit down to chat more about his aspirations, how he balances time between all the responsibilities, and what someone working in tech can do to accelerate their career on an exponential trajectory.

#51 - Finding Your Engineering Passion, with Vicente Plata of 500 Startups LatAm, Shopify, and More

Today I chat with a good friend, mentor, and an all-around great person - Isaac Hepworth. Isaac is the person you should go to if you want to learn more about what it means to be achieving excellence in the product management space. We chat about the role of a problem solver, what it means to be a PM across different companies and titles, and what one can do to better prepare for an industry that changes by the day.

#50 - Problem And Product Management, with Isaac Hepworth

Despite starting a career in product management at one of the big companies, I've never considered to do the same job but working for the government. Not because I didn't want to. Mainly, because I did not know that was even an option. As it turns out - it is, in fact, an option, and a pretty impactful one at that. To learn more about this career trajectory, I chatted with Adrianna Tan, Director of Product Management for the City and County of San Francisco. She shares her journey as a founder of startups and non-profits, an avid hiker and an advocate for an open web, and how it all combines in her work.

#49 - Product Management in Government, with Director of Product Management for the City and County of San Francisco, Adrianna Tan

This is the brand-new start of the third season of The Work Item podcast, and to make the kick-off even better I sat down with our good friend of the show, Dan Shaw, to learn more about their career. Dan shares the story of bootstrapping a Developer Relations arm at PayPal, wisdom around career decisions, and much more in this episode.

#48 - The Story of Working In Developer Relations, with Dan Shaw

The end of 2021 is almost here, and it's time to wrap up the second season of The Work Item. And what better way to do that than to invite a good friend on the show to talk about their journey through the past 12 months? In this episode, I am chatting with Mayuko Inoue about all things 2021, the best choices in comfort foods, McDonalds french fries, thoughts on the content creator career path, and more. We wanted to make this episode very informal, yet informative. To borrow Mayuko's intro to her own podcast, Muko's Corner (which you should subscribe to) - sit down, get cozy, grab a cup of tea, and enjoy the show!

#47 - 2021 Reflections, Creativity, and More, with Mayuko Inoue

The myth of the superhero programmer - we often hear about it, but it's rarely the reality. Being a superhero on a team takes more than just technical chops, and that's one of the topics that I chat about today with Senior Developer Advocate at Microsoft - Christina Warren. You might've seen Christina before on This Week on Channel 9, or even back in the day - at Gizmodo and Mashable. This episode ended up being less of a career chat and more of a friendly exchange about the latest happenings and what we can learn from them. Yes, we even talk a bit about the re-released Grand Theft Auto: The Definitive Edition.

#46 - From Journalism to Developer Engagement, with Christina Warren

The decision to join a startup or a big company is not an easy one, as one has to consider many factors that go beyond just the financial side of things. In this episode, I talk to Jennifer Kim, a seasoned startup advisor with a lot of experience dealing with these kinds of decisions and more. Jennifer also specializes in the people part of the startup equation - arguably, one of the hardest ones. We chat about the current challenges startups encounter in this space, why it's important to build a diverse workforce, and what one individual can do to be a changemaker in their company's culture.

#45 - Startups, Growth, and A Quest to Build People-focused Companies, with Jennifer Kim

You've probably heard of the many types of PM - project managers, product managers, and even program managers. But did you also know that there is a PMM - product marketing manager? I wasn't quite sure what the responsibilities of one would be, so I reached out to Isaac Levin - Principal Product Marketing Manager at Elastic, and asked him to talk about his work.

#44 - So What Is Product Marketing, with Isaac Levin

Developer Advocacy is a relatively new field, but when it comes to knowing how to navigate it, Brian Douglas' knowledge is second to none. As Director of Developer Advocacy at GitHub, he is at the forefront of a lot of the developer engagement efforts - from understanding the pain points of those that use GitHub, to advocating for new initiatives and programs. I sit down with Brian to learn more about what it takes to be a great developer advocate, how one can break into the field, and how you measure success in the role. Suffice to say - it was a packed conversation and we needed more time and maybe even a future follow-up to cover everything.

#43 - Ins And Outs Of Developer Advocacy, with Brian Douglas

Whether you are new in the tech industry or are a veteran developer, chances are that you've used a product that Jeff Atwood worked on. I'm talking about Stack Overflow and Discourse, of course. When it comes to building communities and fostering good conversations, Jeff took an unusual position - steer the conversation towards finding the best in people, argue ideas and not people, and ultimately, contribute to a world that's just a bit better. How does it all work? Jeff elaborates in this episode.

#42 - Building The World You Want To See, with Jeff Atwood

Despite what your LinkedIn feed might tell you, a career in FAANG is not the only way to grow in tech. Or even get started in tech, for that matter. There are many variables in play that can help you determine what career track to pursue, but none more important than the answer to your own "Why?" That's why today I am talking to Chloe Shih, a product manager and content creator, about her journey to a product manager role, struggles along the way, and the realization that work in Big Tech might not be all that interesting or impactful.

#41 - Why Big Tech Is Not For Me, with Chloe Shih

Management, and especially engineering management, is way more than just telling others what to build. Talking to Amro Mousa, an engineering manager at Twitter, it becomes evident that a key ingredient to a good team is empathy. In this episode, I learn from him on what the best way is to lead with empathy in a team, and how one should think about the management track as a potential avenue in their career.

#40 - Engineering and Team Empathy, with Amro Mousa

In the sea of shiny technology objects (I am talking frameworks, tools, libraries, and many others), Dan Shaw has been pretty opinionated - focus on delivering value to the customer first, and tools second. In this episode, I sit down with Dan to learn more about this approach, and how he applied it in his career and work with the Node.js community - after all, he’s known as the Godfather of Node.js.

#39 - Focus on Delivering Value, with Dan Shaw

From the early days - when we are growing up, to when we go to school, we tend to be involved in a lot of activities. From sports, to music, painting, coding classes. But as we grow up, we tend to specialize. One is a product manager, or a Python programmer, or even a doctor. According to my good friend Salman Ansari, this is where we have an opportunity to break out of the typical norms and become a polymath - a person with extensive knowledge in several domains. In this episode, I learn more about Salman's career, as well as his take on how someone can become a polymath.

#38 - Becoming a Polymath, with Salman Ansari

Last time I chatted with Jack, I had pages of questions I still wanted to ask - with this episode, I attempt to address that backlog. And the more I talked to Jack, the more I realized that the theme of his entire career is - "be a builder." As someone who started and worked at many startups, he sure knows first-hand how to do that well and in a way that is sustainable. Today, we talk about his work at Vimeo, what it means to collaborate with others, and how to build a network of folks that are there when you need them most.

#37 - Be A Builder, With Jack Zerby

There is a bit of a chasm between requirements for building open source projects and those that are designed to be closed. Not surprisingly, it also requires a different set of skills altogether if you want to do it right. To learn more about this, I sat down with Jenn Creighton, Senior Staff Open Source Engineer at Apollo GraphQL. Jenn has been building scalable web experiences at companies such as Ralph Lauren, Chartbeat, and ClassPass, and is now leading the work on one of the most interesting and active open projects out there.

#36 - Diving Into Open Source Engineering, with Jenn Creighton

I often hear about folks moving from engineering to product management and back. Others make the transition from marketing and sales to product management. In a first for this show, today I talk to Janine Co, a product manager who recently joined the Microsoft Teams team, who also happened to switch from following a pre-med path to one in product. What things did she consider when making the switch? What did Janine do to build a network from scratch? It's all in this episode.

#35 - From Pre-Med To Product Management, with Janine Co

There are thousands of blog posts, tutorials, and videos that tell you what engineering careers are about, how you should be thinking about your dream job, and promotion trajectory. In this sea of content, it's often hard to separate the common from the edge case. In this episode, I talk to Laurie Barth, a renowned technologist and Senior Software Engineer at Netflix.

#34 - Busting Career Myths with Laurie Barth

What lessons can you take away from a music degree and bring into engineering management? How do engineers work with folks in the newsroom at one of the biggest news organization on the planet? Nicole Tibaldi, Senior Engineering Manager at The New York Times (yes, _that_ The New York Times) is here to tell us more about these things, her work, career, and how to foster a culture where your team feels included.

#33 - Engineering In A News Organization And Beyond, with Nicole Tibaldi

Setting your sights high for a career in engineering management might be an appealing endeavor, but it also means that you will be making a lot of assumptions about future roles without really knowing what those roles are truly about. In this episode, I sit down with Camille Fournier - a veteran CTO, speaker, and entrepreneur, to learn more about ways to map out the path to becoming a CTO (or not).

#32 - Camille Fournier on Engineering Management Paths

Talking to Chad Fowler, you quickly realize what true leadership means. Chad has extensive experience leading large technical organizations such as LivingSocial and 6Wunderkinder, being a venture partner at BlueYard Capital, and now - helping make the Internet safer as Chief Product Officer at DEVCON. Did I mention that Chad also is a musician? In this episode, I talk to Chad about his work, lessons learned from music and travel and how those apply to life and career, and what is the approach to consider for one to carve out a path towards an executive role.

#31 - Lessons In Leadership, with Chad Fowler, VP of Technology at DEVCON

Folks often forget that engineering is inherently a very creative process. Monica Dinculescu found her own niche where she can build impactful things and do it in some of the most unusual ways possible. An excellent engineer, creative thinker, and fellow Eastern European by origin, Monica joins me today to talk about the things she learned as she figured out her career path.

#30 - Creativity in Code and Beyond, with Monica Dinculescu, Engineer Extraordinaire

From Pascal, to writing image processing code, if there is one word you absolutely can’t use to describe Ben Sandofsky’s career, it would be “uneventful.” He was one of the first mobile engineers at Twitter, had a stint helping build Periscope, and ultimately ventured into unexplored territory to finish a photo app he always wanted, that later became Halide. In this episode, I sit down with Ben to get a better understanding of the decisions he made in his career, and what were the critical turning points that made him start his own studio - Lux.

#29 - Building Things You Love, with Ben Sandofsky, Head of Development for Halide

Rebecca Murphey tried a lot of things on her way to becoming an engineering manager at Stripe - from journalism to advertisement, and even learning how to fly. In this episode, I sit down with Rebecca to learn more about her path, what were the important lessons learned in her non-tech career that helped her be an efficient engineering leader, and what aspiring engineering managers can start doing today to figure out if this career track is for them.

#28 - The Art of Engineering Management, with Rebecca Murphey, EM at Stripe

There is a certain air of mystery around careers in Human Resources (HR), and David Daniels, who is a veteran HR leader in tech, is here to bring some clarity about the work. David has extensive experience being in HR at Microsoft, Pinterest, and now - Snapchat. He shares his insights about going from education to leadership in some of the most prominent tech companies, fighting against the fixed mindset, and uncommon recommendations for folks wanting to get started with their careers.

#27 - How to Build a Career in Human Resources, with David Daniels

There is no single, well-defined path to becoming a product manager. There are more questions than answers when it comes to figuring out which skills are necessary, what books or blog posts to read, or which courses to take. Dan Olsen, the author of The Lean Product Playbook, former product leader at Intuit, Friendster, Box, and the US Navy (he worked on submarine design) shares with us some insights on what it means to grow as a product manager.

#26 - How to Grow as a Product Manager, with Dan Olsen

Jack Zerby is not your typical designer. His experience producing music, working at Pentagram and Frog, building startups, pitching to Gary Vee, and now - building tools for creators at Gumroad, puts him square in the middle of a very uncommon career path. In this episode, I chat with Jack to learn more about what motivated him to grow his career, how to break into design, how to make the transition from a big company to a startup, and what does it mean to build compelling narratives in deck form.

#25 - How to Build a Career in Design and Pitch Gary Vee, with Jack Zerby

Jess Lee is the co-founder of dev.to - a developer community that emphasizes the importance of a friendly approach to guiding folks through the tumultuous waters of software development. In this episode, we chat about Jess’ career, the journey to founding Forem - the open-source platform powering large communities, and her experience building successful distributed teams.

#24 - Building Communities with Jess Lee

Charlie Kindel is a tech industry veteran who helped bootstrap, grow, and manage teams that built home servers, phones, voice assistants, home automation software, and hopefully soon - space technologies. In this episode, we dive a bit deeper into Charlie’s approach to product ideation and design, discuss the importance of having a principled organization, and ask questions about his most recent adventure around space.

#23 - From Servers, Phones, and Voice Assistants to Space with Charlie Kindel

Paige Bailey is one of the few Artificial Intelligence (AI) and Machine Learning (ML) experts who is able to convey complex technical topics in an easy-to-understand and relatable language. Her Twitter feed is full of AI/ML paper recommendations, open source projects, and insights about the ever-evolving tech space.

#22 - Paige Bailey on Building a Career In Artificial Intelligence and Machine Learning

Mayuko Inoue made a bold step by defying the stereotypical career path of a software engineer, and became a full-time content creator. Her videos on YouTube answer some of the more salient questions that are almost never covered in your typical coding tutorials and overviews. What was behind this career decision and what were the lessons learned? How do you build a healthy community, and develop a good work-life balance? We talk to Mayuko about her personal take on the unique trajectory she's carving, as well as the lessons learned along the way.

#21 - Mayuko Inoue on Building a Content Creator Career Path

Our first episode of the year is with the one and only Scott Hanselman. We tried to come up with a catchy title, but the entire episode could be summarized in one word - intentionality.

#20 - Scott Hanselman on Intentionality

Den and Courtny reflect on the year we just went through, and discuss our plans for 2021.

#19 - Wrap Up Episode For 2020

Right before the Thanksgiving break, we are releasing a fresh new episode with Megan Risdal, Product Lead at Kaggle. Megan took the multi-talented route to the career she has today, and enjoys every bit of it.

#18 - Megan Risdal on Building a Career at the Intersection of Data Science and Product Management

In a surprising twist, this week we chat with Christos Matskas on two topics - transitioning from consulting life to a corporate life, as well as about building identity tools and services in the cloud.

#17 - Christos Matskas on Going From Consulting to Corporate and Building Identity Tools

This weekend we go outdoors with Bill Kenney, co-founder of Focus Lab, a branding agency that is entirely remote. We talk to Bill about the importance of a good brand and what distinguishes professionals from amateurs in the field.

#16 - Bill Kenney on Building Brands That Last

We sit down to chat with Tarun Gangwani, Senior Product Manager at Sanity.io. Tarun is a seasoned PM with tons of expertise to share about the product management domain.

#15 - Tarun Gangwani on Innovation, Navigating Product Decisions, and Building Growth Engines

In this episode of The Work Item we interview Richard Lander, Principal Program Manager on the .NET team at Microsoft. Richard does a deep dive on communication, being a generalist vs. specialist, and growing one's career.

#14 - Interview with Richard Lander

In this episode of The Work Item we interview Amanda Silver, Corporate Vice President, Developer Division at Microsoft. We discuss the process of building great developer tools, the human element in product design, and career advice for the long run.

#13 - Interview with Amanda Silver

In this episode of The Work Item we interview Christina Weng, product designer at Facebook, about building a career in user experience design from scratch.

#12 - Interview with Christina Weng

We're back after a week-long hiatus with an interview. This time, we chat with Eric Martel, Director of Artificial Intelligence and Machine Learning at Eidos-Montréal.

#11 - Interview with Eric Martel

In this episode of The Work Item, we interview Sara Chipps, Director of Public Q&A at Stack Overflow. Sara is also the founder of JewelBots, a company that provides electronic building kits for young inventors.

#10 - Interview with Sara Chipps

In this episode of The Work Item, we interview Philipp Cannons, CEO and founder of PMFIT.AI - a startup that aims to accelerate product success. Philipp talks about his experience starting a business from scratch and building a deep understanding of large organizations.

#9 - Interview with Philipp Cannons

In this episode of The Work Item, we interview Charmaine Lee, product manager intern at Microsoft, and a friend of the show. Charmaine talks about her experiences breaking into tech, building projects for fun, and being engaged in local tech scenes.

#8 - Interview with Charmaine Lee

In this episode of The Work Item, we interview Dan Fernandez, VP of Product for Developer Services at Salesforce. Dan, a tech veteran, talks about product management, skill stacking, and building great developer experiences.

#7 - Interview with Dan Fernandez

A conversation with Matt Swanson, a software engineer at SEP, on engineering best practices, design systems, and managing complexity.

#6 - Interview with Matt Swanson

A virtual fireside chat with Jin Yang, VP of design at CapitalOne. We discuss leadership, building great teams, and wrap up the show with food place recommendations.

#5 - Interview with Jin Yang

In this episode, Courtny Cotten and Den Delimarsky chat with Clint Rutkas about PowerToys - a fantastic set of utilities for Windows power users.

#4 - Interview with Clint Rutkas

In this episode, Courtny Cotten and Den Delimarsky chat with April Speight, Senior Developer Advocate at Microsoft, about social media, writing Python books for kids and more.

#3 - Interview with April Speight

In this episode, Den and Courtny are talking about their career starts..

#2 - Career Starts

In this episode, Courtny Cotten and Den Delimarsky talk about what it takes to work remotely, along with some tips and best practices.

Episodes