The Media Treadmill

Easy to get on, hard to get off

Six years ago, I started Software Engineering Daily. My initial plan was to build a big enough podcasting business to self-fund other projects. This strategy made sense to me because I figured a media business was too hard to scale. The real scalable business is in software companies, so I should build a software company.

Within 12 months, I could pay for my own living expenses and have about $5k per month leftover to do other things. Thus began a dangerous road of trying to bootstrap software companies in parallel with running a media company.

First there was Adforprize, which failed because I was not tenacious enough, and did not try hard enough to raise venture capital (I mistakenly wanted to own more of the company).

Adforprize was super expensive because I made some very obvious errors: hiring too fast, using contractors, failing to validate the business against a market that I didn’t understand, etc, etc…not to mention trying to manage it while working full-time on Software Engineering Daily.

After losing $250k of my own cash on Adforprize, I decided to focus back on Software Engineering Daily, building out a home grown platform with a job board and subscription business, called Software Daily. We built out mobile apps to handle the subscriptions, and tried to drive traffic to Software Daily to turn it into a sort of social news site.

This was not a smart direction. Nobody wants to login to your social news site. And nobody wants to use a halfhearted jobs board. Network effects are incredibly hard to get going.

So, I tried something else. I teamed up with a few close friends and started Podsheets, a podcasting platform. The initial goal of Podsheets was to make it easier to start a podcasting business—similar to what Megaphone.fm has accomplished. But the project scope grew and morphed into something mushy and vague: simpler podcasting, but also with community management, and also with something like Zencastr built in.

This project was also mismanaged on my part. We had the market timing perfect (around 2017, pre-podcast saturation), and could have built almost any product in the space. If we would have just focused and executed, we would be raking in cash or exiting right now amidst the great podcast consolidation that has swallowed up Advertisecast, Glow.fm, Anchor, and Megaphone itself.

I should mention at this point that unwinding these businesses is incredibly costly, cumbersome, and time-consuming. I foolishly assumed that spinning up and down a business was like flipping a switch on a Heroku dyno. It’s much harder than that.

By the way: this whole time, I was still running the Software Engineering Daily podcast. It was still growing in revenues, still growing in popularity. I was using the cash flows to power these business ideas.

After three failures, I decided to take another swing with FindCollabs. My thesis was that there should be essentially a “higher level Github”, or a “Quora for projects instead of Q&A”. FindCollabs would be the place where people post their projects and find collaborators.

With a large podcasting audience of engineers and hackers listening to Software Engineering Daily, I figured I could crack the network effects problem and get enough people to try out FindCollabs and build their projects there.

There have been so many attempts at platforms trying to solve “founder dating”. Maybe someday this problem will be solved, but I couldn’t do it with FindCollabs. I tried several pivots—morphing it into an internal project management tool, then a hackathon product. But none of the problems I was solving were acute enough.

After 18 months of trying very hard to iterate and market FindCollabs, I stopped working on it in mid 2020.

Adding to these projects, I started writing a book in 2018. That book comes out July 6th, 2021, and I’ll be sharing more details about it in the coming months. The end result of this book is something I’m very proud of, but the amount of work that it piled onto my thinly stretched days was just too much. A good book is VERY hard to write (and I’m not even sure if mine is good).

On the bright side, Software Engineering Daily is doing better than ever. Revenues are high, and we’re keeping expenses low. I’m delegating more of the business to free up my time for other endeavors.

SE Daily is a media treadmill. 5 shows per week, 50 weeks per year, all kinds of different topics. It’s a grind, and it’s hard to scale, but I still love it. It’s a privilege to be able to survey the landscape of technology and choose where to delve into more deeply.

I’ve been pushing myself very hard, in all kinds of directions, for 6 years. I haven’t made exactly the type of success I’ve been aiming for, but I remain optimistic. I still think I can find a software company to start, and I’m digging around for new ideas every day.

Until then, I’m going to try to improve SE Daily, thinking about one of my favorite Quora answers around running a successful business:

The main thing I learned from my failure is: focus on doing one thing really well. Most of my failures came from lack of focusing on one core thing. It is better to do one thing great than ten things mediocre. Focus on the strength of your business, not your weakness. Doing one small thing really well trumps doing lots of big things poorly -- especially when people really care about that one thing. I wish I learned that lesson when I first started my career.

I’m going to continue to use Substack to share some of my thoughts and experiences, as well as to promote my upcoming book. If that sounds interesting to you, please subscribe!

And if this post resonates with you, send me an email or DM. Would love to hear from you.