Welcome to the latest edition of The Entrepreneur’s Tech Stack. I’m your host, Simon Owens. For those who don’t know me, I write a media industry newsletter you should definitely check out.

Today’s featured entrepreneur is Maya Chupkov. In October 2021, Maya launched Proud Stutter, an interview podcast about changing how we understand and talk about stuttering. Within a year of the show’s debut, it was nominated for an Ambie Award, and it’s turned her into a sought-after advocate in the space. To date, Maya’s been featured in over 70 media outlets, including KQED, NPR, KTVU-TV, and ABILITY Magazine. Her show was named on The Guardian’s Top 5 Podcast of the Week list and was featured on Apple Podcasts as New & Noteworthy. In addition to her paid speaking engagements, Maya also monetizes Proud Stutter through a mixture of foundation grants, donations, and a merch store.

Maya walked us through the products that are absolutely essential to her business:


Scheduling guests can be one of the most time consuming parts of podcasting. Calendly is a scheduling tool I use for both my full time job and my podcast. It makes it extremely easy for scheduling podcast interviews and for people to schedule time on my different calendars (I have three!). I am able to pick different time blocks (15 mins, 30 mins, 1 hour, etc) for intro meetings and longer client meetings. I also love the Zoom integration feature, which includes a Zoom link when guests and colleagues book. Overall, it is super user-friendly on both sides. It is totally worth the money due to how much time it cuts from my admin responsibilities.

Pinpoint Google 

Pinpoint from Google is a free platform that stores and analyzes documents, emails, audio files, handwritten notes, and more. While this tool is part of Google’s Journalist Studio, many of the tools are useful regardless of what field you’re in, including for podcasters. Pinpoint has a fantastic transcription service for audio files, which I use to transcribe my podcast episodes. The transcriptions come out fairly accurate compared to other transcription services. Transcription services are expensive so it’s nice to have a tool like Pinpoint that is free and reliable.   

Swell AI 

I have tried almost every AI tool for podcasters out there, and Swell AI is by far my favorite because of the quality. I use Swell AI to help me write blog posts, social media posts, and other forms of content for my podcast episodes. I don’t use Swell AI for all my episodes (I’m still on the free plan which allows for 1 upload a month). For the episodes I do use it for, Swell AI creates the first drafts of show notes, episode titles, summaries, social media posts, and email newsletters. It saves me a ton of time because I’m not producing everything from scratch, but still able to edit each first draft to fit my voice. 

Canva Pro

Canva Pro is my most-used platform. I use it every single day. Because Proud Stutter is a nonprofit, I am able to use the pro membership for free. I use it to create graphics, promotional assets, media kits, episode artwork, event posters, and social media marketing content. I also use Canva’s amazing selection of slide deck templates. I have been getting more speaking engagements, and Canva’s templates allow me to create engaging and interactive slide decks where I can integrate audio and video. The huge collection of templates comes with a giant library of elements for sprucing up slides.


Squadcast is a remote recording service that records locally and then uploads to the cloud. It’s designed really well and the recording quality is excellent, especially compared to Zoom. There are a ton of podcast recording software platforms out there, but after trying all of them, Squadcast is my favorite because of the audio quality, price, and the customer support. SquadCast has also really thought carefully about user experience and I can’t think of anything that would make it easier/faster right now. I also love how quickly it renders the audio tracks for download after the interview ends and that it combines videos after the session is over. I use Squadcast for all of my podcast interviews and guests rarely have questions about how to use it.

Adobe Podcast

Adobe Podcast is a free, AI-powered audio, recording, and editing platform. I use the Enhanced Speech tool, which gets rid of background noise of certain audio tracks with high levels of background noise. Many of my guests are not able to be in quiet environments and do not have the equipment to ensure the best sound on their end. Since all my interviews are remote, Enhanced Speech allows me to upload certain audio tracks to help ensure professional audio quality. This frees up my time so I can focus more on interviewing and production.

Want to be featured in a creator spotlight like this one?

Each interview is heavily featured in front of my 14,666 newsletter subscribers, and I share it out to my 70,472 social media subscribers.. Go here to contact me and tell me a little more about your business. 


Simon edits an industry newsletter that covers everything from the Creator Economy to traditional media. He also hosts The Business of Content, a podcast about how publishers create, distribute, and monetize digital content.

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