The Story Behind the Squid
How a podcast for a leadership legend became the catalyst for something bigger.
WiseSquid was born from a simple ask: help a mentor launch his podcast. What I didn't expect was that it would turn into a platform that could help every Substack podcaster do their best work.
It Started with Dr. Duncan
Dr. Rodger Dean Duncan is one of the foremost experts in organizational leadership in the world. He's consulted for Fortune 500 companies, written best-selling books, and maintained a Forbes column interviewing thought leaders for years. He also happens to live in my hometown, and growing up, he was one of those important adults who had a deep influence on me.
When Dr. Duncan mentioned he wanted to start a podcast, I knew I could help. What I didn't tell him right away was that I actually had some expertise in this area. One of the most successful podcasts in the world, Entrepreneur on Fire, was in its early days when John Lee Dumas worked with me to launch his first ebook. Through that process, I learned a lot about podcasting from someone at the top of his game.
When Dr. Duncan sent me his first list of 20 guests, I about died. New York Times best-selling authors. Celebrity CEOs. At one point he casually mentioned, "Have you heard of this man named Guy Kawasaki?" Yes, Dr. Duncan. Everyone in tech knows Guy Kawasaki.
Why Substack?
We landed on Substack for a reason that anyone in digital marketing understands: your email list is the only audience you truly own. If you're a TikTok influencer, your audience belongs to TikTok. Instagram followers? They're Instagram's. But an email list? That's yours.
Substack threads this needle beautifully. There's a website, there's a podcast mechanism, but it all comes back to email. And it makes pushing out an RSS feed dead simple so you're on Apple Podcasts, Spotify, and everywhere else your listeners might be.
The Problem I Had to Solve
Right away there were bumps. Substack doesn't make it easy to know all the structured data you can include with an episode. Open Graph metadata, Twitter cards — the stuff that makes your links look professional when shared — was a mystery.
I was also responsible for creating all the assets: quote graphics, story images, audiograms. It started as a completely manual process. Descript for transcription. ChatGPT for extracting quotes. Canva for graphics. Each tool left something wanting, and I was spending hours per episode on busywork instead of helping Dr. Duncan make great content.
So I started coding.
It began as a local tool to keep asset generation organized. Over time, I replaced Descript with APIs. Replaced Canva with programmatic templates. Built custom code for audiograms with animated waveforms and synced subtitles. Created a system that could extract quotes, let me pick the best ones, and generate everything automatically.
Guest Guides Changed Everything
One of the most important ways to help your podcast grow is having guests share their episodes. If your content is great, your guests probably have bigger audiences than you do. That's the point.
But asking guests to share is one thing. Making it effortless for them is another. So I started creating guest guides: beautiful HTML pages with all the assets, ready-to-post social copy, and email templates. Send your guest one link, and they have everything they need to promote the episode to their audience.
The internal team got guides too — with structured data ready to paste into Substack, visual assets, and copy for every platform. What used to take hours now takes minutes.
What WiseSquid Does
Upload your MP3 and a guest headshot. WiseSquid transcribes the episode, identifies speakers, and extracts the best quotes — short ones for graphics, longer ones for audiograms. You pick the winners (because you, the human with taste, know what deserves to be shared).
Then the magic happens: branded square images, story images, audiograms with animated waveforms and synced subtitles. Internal guides with complete Open Graph data. Guest guides with everything your guest needs to share.
Ten minutes per episode. That's it. The rest of your time goes back to making your podcast incredible.
Want to work together?
I'm looking for Substack podcasters who want to make WiseSquid even better. You focus on the content. Me and the squids will handle the rest.