What I Learned From 250 Podcast Episodes — The Bootstrapped Founder 251

The 3 biggest lessons from 250 episodes.  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌

Dear founder,

This week, I celebrated the podcast reaching 250 episodes with my most recent interview with Amanda Goetz. Just last week, the podcast hit 250,000 overall downloads.

These are numbers I never expected to reach. And here I am, still enjoying creating new episodes and interviewing people every week. Today, I want to reflect on the podcast’s history and its importance in building my media business.

Fumble Beginnings

My newsletter, podcast, and blog are three different aspects of the same goal. Everything I do involves writing, and writing is where it started for me. It wasn’t a conscious choice against podcasting or making videos and for writing. It was just the only thing I could think of doing after selling my SaaS business.

I drafted a few articles, started a blog, and shared my stories with the fledgling Twitter audience I was starting to build. Over the past two and a half years, that content creation effort has taken various forms, like making YouTube videos, recording podcast episodes, or writing a weekly newsletter.

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And, since I am a naturally lazy person, I had to establish a highly effective process to keep doing these things for more than just a few weeks. After a few blog posts, I set up the newsletter so that I had a weekly deadline for the next article. When a reader told me they had dyslexia, I started the podcast. And eventually, I turned on a camera while I recorded the pod. That’s a lot of stuff, but it all works together.

I made it fun. Setting up a structure for my work helped me find relevant ideas, formulate thoughts, and present them cohesively to my readers, viewers, and listeners.

After 250 episodes, I’ve learned some important lessons. So, let’s dive into a few of them.

Validation Isn’t Just for SaaS Businesses

One key aspect of my work is finding pre-validated topic ideas within myself and my community. Most of my solo episodes and articles come from topics I’ve recently discussed or read about on social media. I never start with a blank slate; instead, I focus on what’s already being discussed and add my unique perspective to the conversation.

This doesn’t mean I am always chasing the latest hype: many of the topics I find interesting end up in a massive backlog of title ideas and early-draft articles. But for every major topic I talk about, I know where it’s coming from. I often even save the Tweet URL or Hacker News discussion link for that particular idea so that I can reference and use it for research when I choose to dive into that topic.

I learned this from my own early-stage software business validation efforts. The best way to find a critical problem in the wild is to listen to people complain and help each other in their communities. Not every complaint is a reason to start a business trying to solve it, and not every conversation is a good topic for an article. But looking at any such exchange as an opportunity to contribute something helpful will quickly surface amazing themes for you to dive into and then share your insights back to the community.

Tools Work Better Than I Do

Another important lesson is that all of this only works when I focus on what I enjoy most: thinking and writing. There are parts of the content creation process that just aren’t as enjoyable, like creating thumbnails for videos or checking transcriptions for errors. To save time and energy, I’ve found tools and people to help with these tasks.

In the content creation process, there are three parts: ideation, contemplation, and creation. I prefer contemplation, the middle part, so I use tools to speed up ideation and creation. For example, AI-based tools help me draft ideas and identify relevant community conversations. Tools like Syften give me insights into topics that interest me, while ChatGPT helps explore potential topics. Tools like this can be writing and research assistants, and I use them a lot during the ideation part or writing.

For the contemplation stage, I use Audio Pen to record my thoughts on a topic, which condenses them into something manageable for drafting later. Once I have a draft article or episode outline, I turn it into a fully-fledged piece of content for the week by expanding my sketch of a draft into an actual piece of text written by me, a human.

Retain Control Over the Creative Streams

I mentioned earlier that I’m somewhat lazy when it comes to doing the repetitive stuff. But I’m not trying to outsource everything. Particularly not the parts of the post-production process that themselves are potential idea generators.

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For my interviews, I still edit them myself because the process can spark new ideas. Even though one person of the two or more in the conversation is me, I find that listening to the chat again during editing brings up thoughts that didn’t occur during the recording. Thoughts that are (yet again) founded in an existing conversation that already matters to people. Great topic validation here.

Once the interview is edited, the video file rendered, and the podcast audio file created, I use AI-based tools for writing descriptions and highlighting parts of the interview. To get an accurate transcript, I use various tools and have people check them for accuracy. This is just cleanup.

I enjoy the thinking, structuring, and drafting parts of my work and don’t use tools for those tasks.

The act of writing is very important to me. After all, it’s at the core of all I do. Every week, I spend at least one full day doing this. Consistently enjoying this part of my work is one reason why I continue doing it.

Pivot Towards Connection

Finally, a learning that I can see clearly in my metrics. One significant change in my podcast was starting to interview people from my audience and those I look up to. After 160 or so episodes, this shift brought new perspectives and helped grow my podcast in terms of viewers and monetization opportunities.

Solo shows are great, and they allow creators to leave traces of their ambition. But as a solo creator, all the audience growth is driven by you. But when guests share your episodes with their audiences, it introduces new people to me and my prior work every week. The effect of this was immediate.

Involving others in conversations makes it easier to grow an audience over time since new guests bring new listeners with them. It also spices up the variety of topics that the show is about. New people, new ideas, new angles.

And when you do that every week for a few years, you find ways to make it interesting every time. I certainly started feeling more confident after a few episodes, and I know that I can go into a conversation feeling relaxed and prepared.

Ah, yes, preparation.

Having a consistent pace and release schedule allows me to prepare for weeks when I don’t feel like working by pre-recording interviews and articles. The fact that I have. over 50 articles pre-drafted in a database, ready to go when I need one, makes me sleep very calmly at night. I know that I can record an interview in an hour and edit it in two. I’ll never run out of interesting people to talk to or interesting ideas to talk about.

That’s what a consistent process and the experience of doing it a few hundred times can do for you.

Where to Go From Here

With 250 podcast episodes under my belt, I hope to continue for at least another 250 episodes. There are so many more things to share and people to empower.

I want to say thank you to everyone who’s read, viewed, or listened to anything I’ve said, to sponsors who’ve supported my podcast, to guests who shared their expertise, and to everyone who’s interacted with me along the way. Your support is greatly appreciated.

Here’s to reaching the next milestone of 500 episodes together!


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Bootstrapped SaaS Exit Planning — The Bootstrapped Founder 243

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