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

Shirley Wu is back-to-back on The Work Item - we previously talked about her unexpected career in data visualizations, but for this episode we're switching things up a little bit and instead focus on building long-term career advantages based on Shirley's experience. This is an especially important topic in the era of AI, where folks have a lot of uncertainty about their career tracks and what it means to build durable moats that can survive the industry being upended by new tools and approaches to getting things done. Shirley's experience is particularly relevant here as an independent studio owner - she's someone who has years of experience to lean on flying solo and seeing how one can establish their own reputation and image in the space.

So, get this - how many times did you have one of your tweets go viral? Now, how many times did a tweet go viral for a project that you built around something that you really enjoy? And out of those times - how many times did a tweet go viral because Lin-Manuel Miranda himself retweeted you? Can't say that I am a member of that club, but luckily I know someone who is - Shirley Wu. Shirley is, what I describe her as, a wizard of data visualizations. If you look through her work, you'll quickly realize that she's not just presenting the data, but rather paints a story around it. Whether it's for people of the pandemic, an analysis of Hamilton lines (that's the project I alluded to earlier), or a myriad of other projects, her work is truly second to none. In this interview, I wanted to learn more about what sparked her interest in this field, whether the sudden visibility was a reward for hard work or instead added more pressure to produce more highly-visible projects, and of course - how to find your unique voice in a sea of people that do similar things (the Internet, if you didn't know, is truly vast).

We're often operating under the false illusion that the career track we have now is the career track that we somehow have to follow under any circumstances - it's easy to snap to common conventions around progression, where you work, and how you work. But what if there's more to the "choose your own adventure" track that we do not know about? To get to the bottom of this question, I sat down with Lenn Pryor, a seasoned executive who used to work at many well-known companies, but decided to carve out his own niche where he found both joy and professional satisfaction. It's a risky bet that paid off, and I was keen to learn more about how he justified it and what decision points helped him navigate the overwhelming ambiguity. What I really enjoyed about recording this episode is that the learnings are broadly applicable no matter what role you are in or are looking to jump into.

Every year, millions of students try coding for the first time through Hour of Code. But most people don't know that the technology powering those experiences is ran by someone who didn't really have a plan to become a CTO. In the fourth episode of this season of The Work Item, I am talking with Simon Guest, CTO at Code.org. Simon walks me through how he actually became a CTO (not the LinkedIn version we commonly see), and what skills helped him succeed despite the fact that there was no pre-charted path he could follow. You'll be surprised to learn just how much serendipity and having the skills in the right place at the right time play a role in strapping one's career to a rocketship. We also talk about the future of coding, whether AI is truly going to make engineers obsolete, and what we can do to build a good career moat that sets us up for long-term success. And of course, if you've ever wondered what it takes to move into technology leadership, this conversation will give you a very realistic picture of what that path looks like.

In this week's episode, I sat down not with one, but two brilliant guests - the duo behind the brand-new venture known as SaaS Marketing Gym, Lianna Patch and Colleen Schnettler. As coaches and community leads for SaaS founders, they offer a refreshing counterpoint to the doom-and-gloom narratives trending on YouTube and other social channels about AI rendering software businesses obsolete. Through Lianna's conversion-focused (and delightfully humor-filled) copywriting expertise and Colleen's technical background, they're equipping SaaS founders with marketing strategies that prove software businesses aren't just surviving the AI revolution—they're positioned to thrive alongside it. What made our conversation so compelling was their evidence-backed optimism (a rare treat, I know) about the future of SaaS. While tech pundits predict AI will replace traditional software services, Lianna and Colleen articulate exactly why human-designed software solutions remain vital and how founders can use AI as an enhancement to what they're building rather than a replacement. Our discussion covers both the challenges of the current landscape and the surprising opportunities AI creates for SaaS companies that want to ride the wave. We talk about their origin stories and how they continuously evolve their skills to stay ahead of the curve. I guarantee you that you'll walk away with immediately actionable tactics and insights regardless of your company stage, and perhaps most valuably, a renewed confidence that SaaS remains a business model with staying power.

Chief Technology Officer - a few people I've talked to in the past year expressed some degree of interest in reaching, what seems like, the pinnacle of an engineering career. That three-letter title carries weight in boardrooms and across the industry alike. But beyond the fancy business cards and the seat at the executive table, what does it actually mean to hold the technical helm of an organization? Is it the promised land of pure architectural decisions and strategic vision, or something messier, more complex, and perhaps more rewarding in unexpected ways? Today, we're peeling back the curtain on the CTO role with Taiwo Oyeniyi, who'll share his journey from engineer to executive. Rather than relying on generic career advice or job descriptions, we'll hear firsthand about the transition, the challenges, and the realities of the position. Taiwo will explore the skills that matter most (spoiler alert: they might not be the ones you're cultivating now), the hurdles he faced along the way, and how the role has transformed his relationship with technology.

User research is an underappreciated art - we in tech are so used to being immersed in an ocean of quantitative data that we can forget that on the other side of the screen are real humans who want to solve very specific problems. And often times, their problems are extremely hard to put a number on. Why did they abandon their cart right before checkout? What made them start creating a new newsletter but then abandon it but come back a month later? Not everything can be answered with a SQL query against the telemetry database. Marisa Morby, a Principal Researcher at Observable, sat down with me to help me better understand what it means to be great (not just good) at user research, and how that can help produce a whole new range of unexpected product insights. And Marisa definitely knows what the impact of great user research can be on the product - she previously worked at such notable companies like Netlify, Gatsby, and Accenture Song, where she honed her skills and UX instincts.

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 - Kent C. Dodds, Jerod Santo, Rob Walling, Adrienne Tacke, David Khourshid, Saron Yitbarek, Rachel Andrew, Katie Fujihara, Lena Reinhard, Miriam Suzanne, Kirupa Chinnathambi, Craig Hewitt, Jennifer Wong, Jason Lengstorf, Michael Kennedy, and Asia Orangio. This turned out so well, that I will be definitely re-visiting the format in the new year. I hope you have a successful and adventure-packed 2025, with plenty of room for career growth. See you next year!

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. Whether you're a startup founder or a seasoned marketer, I promise you that her insights will challenge your thinking and inspire quite a few new ideas. In this conversation, Asia shares her journey from marketer to founder, unraveling the lessons she's learned while scaling SaaS companies and guiding others to do the same. We'll explore her philosophy on growth, the common mistakes founders make when trying to identify their growth levers, and the power of understanding your audience on a deeper level. This really ended up being a masterclass in sustainable growth and customer-first business foundations.

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.