​

​

​Podcast, YouTube, Blog​

Dear founder,

​

Sometimes, you have to pivot. And that's harder than it seems: old assumptions are deeply ingrained, new frontiers look scary.
​
But right now, Podscan needs this. And today, I'll share what happened, why I'm changing direction, and where this will go.

​

🎧 Listen to this on my podcast.​

​

​

Looking back at 2024, it's been a year of significant transitions, learning curves, and unexpected opportunities. The biggest professional shift was the launch of Podscan, a podcast alerting and data platform that has become my main focus and quite possibly the most ambitious project I've tackled so far.

​

The genesis of Podscan is actually quite interesting. It started as a marketing play for another project, Podline, a podcast voicemail tool I had been working on throughout the winter of 2023. I needed a way to reach podcast creators to market Podline, and in classic developer fashion, I built my own solution.

​

Little did I know that this marketing tool would eclipse the original project entirely. Podline itself ended up serving as a technological preview for Podscan – it already handled voice transcription for voicemail messages, making them searchable and visible on the website. These core technologies would later become crucial components of Podscan's infrastructure, just at a much larger scale.

​

What makes Podscan fundamentally different from my previous ventures is its inherent scale. Most SaaS businesses grow gradually - you onboard customers one by one, and your infrastructure needs scale with your user base. Podscan turned this model on its head. From day one, we needed to process every podcast out there. When a customer wants to track their mentions, they expect to find them everywhere, not just in a subset of shows. This meant dealing with millions of podcasts right from the start.

​

This reality check led to one of my biggest mindset shifts of the year. Despite being a committed bootstrapper, I realized that some businesses simply require a different approach. The infrastructure costs would be substantial before revenue could catch up.

​

Fortunately, I found a bootstrapper-compatible funding solution through the Calm Company Fund in March. This funding has been instrumental in helping establish a steady operational baseline while we work toward profitability.

​

Another significant change was my approach to building the business. Instead of trying to do everything myself, I brought on Nick as my designer, business strategy consultant, and customer outreach specialist - essentially an almost-co-founder. His work on website design, email workflows, and customer interviews has been invaluable, allowing me to focus on the technical challenges of building a system that processes over 50,000 podcast episodes daily.

​

This was a dramatic departure from my previous "I can do this myself" mentality, where I'd often dismiss tasks I couldn't find time for as unimportant. Nick has helped me realize that sometimes you need someone else thinking about different aspects of the business while you focus on your core challenges.

​

The technical complexity of Podscan has been staggering, particularly around what I've come to call "data fidelity" - a concept I never thought much about before this venture. The open podcast ecosystem is built on RSS feeds, but these feeds come in countless variations. Some include transcripts, others don't. Audio files might be MP3s, videos, or even JPEGs. The data is often incomplete, confusing, or duplicate. Add to this the challenge of interfacing with closed ecosystems like Apple Podcasts and Spotify, and you've got quite the technical puzzle. The quality of this data is crucial for our customers in podcast analytics and market research, but automating quality control at scale has been one of our biggest challenges.

​

I'm incredibly fortunate to have started this venture during the age of large language models and AI systems. Podscan simply wouldn't have been possible as a solo founder three or four years ago.

​

Two technological advances made it feasible: automated transcription using OpenAI's Whisper for speech-to-text, and instruction-based language models for data processing. I've integrated various AI models - from open-source options like Llama and Mistral to cloud services from OpenAI and Anthropic.

​

The experience has been mind-blowing, especially when the AIs themselves help write code to interact with other AI systems.

​

This deep dive into AI has transformed my development workflow and led to an interesting shift in my podcast interview strategy. I've started specifically seeking out guests who can help me understand the technologies I need for Podscan.

​

Whether it's experts in prompt engineering, marketers with deep industry knowledge, or specialists in feature flags, I've been strategically using my podcast to learn from experts while sharing those insights with my audience. The learning curve with AI has been steep - each new model version requires different approaches to communication and data structuring, different context windows, and different ways of extracting reliable information at scale. But the results have been worth it, as our system becomes more stable and reliable every day.

​

One significant realization this year was about the limitations of personal branding for B2B SaaS. While building in public and maintaining a personal brand worked well for my books and courses, it hasn't scaled the same way for Podscan. When you're selling to agencies and marketing departments rather than individuals, you need different approaches. This insight has led to a recent pivot toward more scalable outreach mechanisms like SEO and content marketing. It was a hard lesson to learn - that the same strategies that worked for selling books and courses one at a time wouldn't work for a B2B SaaS product.

​

The highlight of my professional networking this year was attending MicroConf in Atlanta. I got to meet so many fellow founder nerds, and even ran into a few Podscan customers. It was probably the most rewarding conference experience I've had, even compared to my previous speaking engagements there. The connections and relationships built within the community have been invaluable.

​

I'm already booked for next year's event in New Orleans, and I've realized I need to expand my conference circuit to include podcast industry events. Being present in the podcasting community, meeting agencies and marketing departments face-to-face, has become a clear priority for growing Podscan's presence.

​

On a personal level, turning 40 prompted me to take my physical health more seriously. Inspired partly by Peter Levels' tweets about fitness, I established a regular workout routine and made significant dietary changes - cutting out sugar, focusing on hydration, and staying active throughout the day.

​

The impact has been remarkable, not just physically but in terms of my energy and endurance for work. This improved physical condition has been crucial for maintaining the energy levels needed to tackle Podscan's challenges.

​

I've also been more intentional about reading, though I tend to do it in bursts - sometimes devouring a book in days, then not reading for weeks. It's part of my attempt to create a life where different activities balance each other out, not necessarily happening simultaneously but maintaining a healthy equilibrium. This approach to balance has been crucial as I juggle the demands of Podscan with my media business, which I've had to scale back from two episodes per week to a more manageable schedule.

​

Looking ahead to 2025, I'm excited about Podscan's trajectory. It's not just the biggest business I've built, but also the most complex and impactful, judging by our customer interactions and their downstream effects. The integration of AI into development workflows will only become more crucial, and I'm ready to embrace that future.

​

2024 has been transformative - from launching Podscan to embracing AI, from personal health improvements to strategic business pivots. It's been a year of learning that some rules are made to be broken, whether they're about bootstrapping or doing everything yourself. Sometimes the best path forward is the one you least expect.

​

​

If you want to track your brand mentions on podcasts, please check out podscan.fm — and tell your friends!

​

​

Thank you for reading this week’s essay edition of The Bootstrapped Founder. Did you enjoy it? If so, please spread the word and ​share this issue on Twitter.​

If you want to reach tens of thousands of creators, makers, and dreamers, you can ​apply to sponsor ​an episode of this newsletter. Or just reply to this email!

​