Episode 20: Anne Gentle


Show Notes:

After writing a traditionally published book, Anne Gentle, self-published her second: Docs Like Code.

“No one else is doing this, I better write this down.”

A product manager at Cisco, Anne used her side project as a way to experiment with the full scope of product management from writing, to selling, and marketing it.

Anne shares how she got better at self-promotion, why she hired a life coach and how she wrote her book while having a day job.


Episode 19: Zed Shaw


Show Notes:

Software developer and author Zed Shaw recently made the decision to start charging for his Learn Python the Hard Way book. He discusses why he made this decision after offering the book for free to the community for years.

“In many ways open source has conditioned me to not appreciate the value of what I do.”

Zed talks about the challenges of making money in open source software, the value of consistent practice and how he consciously switches mindsets for different phases of work.

Episode 18: Carla Hackett


Show Notes:

Calligrapher and hand-letterer Carla Hackett shares her journey translating an in-person workshop into a paid online course.

“Could this be a new path I take?”

After holding successful workshops in-person, Carla longed to serve more clients internationally. Carla tells us about the process, how she choose which currency to sell the course in for a global audience and when she starting promoting her new product. 

Hercules (L) and Benedict Cumberbatch (R)

Hercules (L) and Benedict Cumberbatch (R)

Episode 17: Kim Goulbourne

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Show Notes:

Often businesses and side projects are born out of a desire to solve a problem we have. That’s exactly what Kim Goulbourne was doing when she launched No Questions Asked. Kim created this community event while she had a day job.

“I need deadlines or nothing will get done. I have to be working towards something.”

Kim talks about how she lowered her out-of-pocket expenses through sales and sponsorships and how she plans to build more marketing into her schedule in the future.

What to read: Why your brain hates selling

Episode 16: Matt Wynne

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Show Notes:

Matt Wynne, the CEO and a founder of Cucumber Ltd talks about building Cucumber Pro, a product designed to solve collaboration problems and bridge communication in software.

“It’s harder than you think. It takes more resilience than you think."

Matt gives us a behind-the-scenes look at building a boot strapped product. He shares the mistakes they made with Cucumber Pro 1.0, why they eventually built code they knew they'd throw away and the importance of asking the right questions.

What to read: How learning to ask questions transformed my career

Episode 15: Nadia Odunayo

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Show Notes:

Nadia Odunayo is a software engineer and founder of Ignition Works, a consulting company but she's also a dancer.

“Always surround yourself with people who are better than you.” 

Nadia shares how breaking down her performance transformed it, the role of actionable feedback, what to do if you're stagnant when learning something new and how to know when to quit.

What to read: Wait, do that again! The secret to repeating your success


A post shared by Nadia Odunayo (@nodunayo) on

Episode 14: Jenn Schiffer

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Show Notes:

Web app developer, pixel artist and tech satirist Jenn Schiffer loves to build tools that facilitate the creation of art and lower the barrier to get new people into programming, especially young girls. 

"I built this for myself so I wasn’t concerned about getting it out there.”

During our chat, we talked about the origin of make8bitart.com, why she didn’t monetize the site despite thousands of daily visitors, when to add features to a project that doesn’t make money and her accidental promotion plan. We also talk about why naming is the hardest thing in computer science and I share my own naming story for the first time.

Episode 13: Sumi Tonooka

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Show Notes:

Sumi Tonooka is a jazz composer and pianists with a 30 year career spanning Philadelphia & Boston, to New York & Seattle. Sumi and I talked her experience of composing For Malala.

“You have to remember that you’re writing for human beings.”

We talked about the creative process, creating productive routines and how constraints can distill and be beneficial. She also shares Miles Davis’ advice to John Coltrane on how to know when to stop in the creative process. 

Episode 12: Owen Williams


Shows Notes:

Developer and journalist Owen Williams started his popular newsletter Charged because he was worried about the demise of Twitter and a longing to have a platform he owned.

"If I found myself needing a job, I could email the list with a nice message about emailing back and I think people would do that."

Highlights include: how creating a well-received newsletter can be a career changer, the best way to monetize a newsletter, whether your side project has to make money and how to build a paid product on top of a free one.

Episode 11: Seb Rose

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Show Notes:

Despite the idea that we think they should, careers don’t always progress in a linear fashion. The career of Seb Rose, a software developer and partner at Cucumber Ltd has taken many turns including serving as a pastry chef and builder. He’s also worked for himself as well as with large companies like Amazon and Google.

"Our challenge is to deliver value to the community around us and also to be happy in ourselves."

Seb talks the power of BDD, how he came to Cucumber and his thoughts on career.