
I’ve tried my hand at making it in the online space a number of times. I don’t know why, but I just feel drawn to creating things online. I love it because I enjoy the creative process and the idea that I can send my voice out into the cosmos and maybe make a difference somewhere. But I hate it because I can’t figure out how to make any money from it.
One of Many Ideas I’ve Tried
Here’s a list of some of the online business ideas I’ve actually started to at least some degree:
- Sidekick Law. The idea was that every business needs a trusty sidekick. This was a website on legal aspects of starting and running a business. I had short 10,000 foot flyover courses about choosing a legal entity, asset protection, contract formation basics, review of common contract terms, etc. I didn’t make any money from this.
- Porcelain Throne Books. I was going to publish short stories that were designed to be read in a few bathroom sittings. My first (and only) book was about pirates. It is called “Buccaneer Dan the Most Fierce and Good-Looking Buccaneer of All-time in a Quest for Treasure: Part I.” I did a promotion and gave away over 200 digital copies of the book, but I did not make any money from this.
- Star Wars Rookie. This was going to be a podcast going into the details of Star Wars on a step-by-step basis. I was going to talk about the history of star wars and the development of canon. I actually don’t know that stuff, so the concept was we would be learning together. After developing the idea, I watched The Last Jedi and decided I wasn’t actually all that interested in Star Wars.
- Cool Cat Crap. We got a cat and she was so much fun as a kitty. I thought it would be fun to have a website that was just about cool stuff you could get for cats. For some reason, I pictured samurai outfits for kitties. But it would also have all the more practical cat stuff. I didn’t even start the actual website for this, but I loved the idea.
- Law of the Brand. This was another legal idea. This was going to provide trademark services. The reality, though, was that there is almost nothing that I would like less than handling bureaucratic red tape for people. I just thought it might be fun dealing with branding and that creative side of business. I did a few trademark applications from a guest post I did, but I decided this was not something I could see myself doing.
- Dumbcases. I was going to blog about cases where businesses get sued for what may seem like dumb reasons. I was thinking about cases like the McDonald’s hot coffee case or the refusal to make a wedding cake case. I was going to break the cases down and follow them to see whether they were dumb after all. I actually think this one would be quite interesting. I started the website and did some write ups about the McDonald’s case, but I put it on the backburner to pursue other things. I wasn’t sure how I would make any money on this one.
- Dash Gardening. I developed high blood pressure and have been trying to keep it under control. Part of controlling high blood pressure is reducing your sodium intake. I found an easy way to reduce your sodium intake is to eat more whole fruits and vegetables. I started eating more vegetables and composting the scraps. This blog was going to be about gardening as a means to controlling hypertension.
- Go Sweet Fox. I literally had a dream that I was the “cheesecake guy” around town. It was such a fun dream that when I woke up, I thought, “Maybe I can be the cheesecake guy.” So I set out to figure out how to make the world’s best cheesecake. I succeeded in this and was going to blog about it. The problem is that I like my recipe so much better than most of the ones I find online. This makes it not that interesting to blog about. At the same time, I don’t want to run a retail store for cheesecake (well, sometimes I think it would be cool).
- Idaho Consumer Law. I did have a lot of success marketing my law practice online. I did consumer rights cases in Idaho. My website was one of the main ways people found me. But I didn’t make money online. I just used the web to market my services. For that reason, I count it as a good use of the web and developing a niche website that can rank on Google, but I don’t count it as an online business.
I still own some of these domains. Some I have let lapse. I also own a bunch of other domains that aren’t mentioned above because I’m sitting on them thinking that maybe one day I will use them.
But today, I’m sharing a story about an online venture I did try.
Small Business Stories: A Near Miss
The Idea
When I was a kid, I enjoyed reading Entrepreneur magazine. I just loved the stories. They read like a hero’s tale. You start with some nobody with just an idea. This person then faces a million obstacles, reaches a point where most people would quit, but then digs in deep and is able to persevere. They are just good stories.
I started listening to podcasts like “How I built this” and “Entrepreneur on Fire.” These podcasts are great, but I didn’t want to hear only about big, famous businesses like in “How I built this.” It seemed so inaccessible. EoFire also mostly seemed to recycle a lot of the people that were running the podcast circuit–Gary Vaynerchuk, Tim Ferris, Etc. I was tired of hearing from the same people. Plus, I just wanted to hear the stories. I liked the business daydream (and still do).
In 2013, I decided that I could start the podcast I wanted to hear. It would be a podcast about small business owners from the local places around the corner. I wanted to hear the story of the guy who started the local Filipino restaurant or the gal who built some product out of her garage. I thought these would be really interesting stories from people who weren’t trying to market themselves as a business gurus.
Getting Started
I started a website (using the same method I discuss here: starting a website for my blog in 5 steps). I also joined a podcasting mastermind class held by John Lee Dumas of EoFire. I will tell you what, he delivered.
He provided good, practical advise and laid out a strategy on how to position your podcast for success. The goal was to get to “new and noteworthy” by the staff of iTunes. Getting to be New and Noteworthy meant that iTunes would put your podcast on the front page of iTunes for at least a few days. That’s obviously a good thing for exposure.
Once I felt like I knew how to get a podcast going, I just started reaching out to business people I knew. I wanted to get at least one recognizable brand to hopefully draw attention. I reached out to Dollar Shave Club, who had just recently made national news headlines for their viral YouTube ad. Michael Durbin of DSC agreed! So he was my highlight guest. Another guest I was really excited about was Chris Vallone of Classic VW Bugs. He restores VW bugs and even did one for Jerry Seinfeld!
Well, the idea seemed to work in that people tuned in to the podcast. I even made it on the #2 spot on the New and Noteworthy front page.

My first week had over a thousand downloads. It kept growing and within a couple months, I was getting about 5,000 downloads per episode.
It was very exhilarating to have my voice out there and to see that people were tuning it. Everything was very exciting.
Behind the Scenes
I didn’t really have a solid plan for what I was going to do to make money from the podcast. I just kind of assumed people would reach out to ask me for help or sponsors would come flocking. It was an “if you build it, they will come” philosophy.
Even though I was getting podcast downloads, I was not getting much traffic to my website. I put out lead magnets–offering people something to entice them to head to your website–with very little success. I would ask people to write in to let me know what they wanted to see or if they had businesses they wanted to hear from in their area. I had very little interaction.
Meanwhile, I had a more-than full-time job as an attorney. Not only was I an attorney handling a full caseload, but I was helping with some of the business management issues at the firm too. I was supposed to be billing a certain volume per month and assisting with the management. And then I added this podcast on top.
I was waking up at 4:00 am to work on the podcast until 7:00 am, when I had to get going to work. I had to schedule interviews during lunch breaks.
This was also just after my firm had been hit by the ripple effects of the housing market crash. I wasn’t making very much money because we had a lot of debt to service. Work was not particularly supportive of the podcast because, candidly, it did occupy a lot of my available emotional bandwidth and it didn’t necessarily help the firm in a meaningful way.
I kept at it for as long as I could but eventually my productivity at the office really began to dip. I was far too focused on Small Business Stories. I couldn’t help it. It all felt so exciting and I was very much enjoying being able to express myself creatively and having my voice out there. I also believed in what I was doing–sharing inspirational stories of how people got their dreams started, overcame challenges, and found success.
End of the Season
One of the most challenging parts of the podcast ended up being finding and coordinating with guests. It turns out that I didn’t personally know a lot of business owners. As a result, I was doing a lot of cold calling or cold emailing. I tried to network with business groups as much as I could: chamber of commerce, alumni groups, LinkedIn groups, etc.
This all took time.
It eventually took up so much time that something had to give. And that something was my billable hours.
Once my billable hours dropped, I was asked to stop the podcast.
I was kind of okay with it because I was tired and maybe a little burned out. I was also out of episodes to air.
I agreed to stop the podcast to get my billable hours up. In the meantime, I was thinking of ways to make room for it. I really didn’t feel like I was ready to give it up, I just had to recalibrate.
So I announced that I was ending the first season of episodes and that I would be back with season 2 in “the Fall.”
Recalibrating
I knew if I was going to bring back Small Business Stories I had to find a way to take some things off my plate. I thought I could pass the torch of the firm’s administration issues to someone else. In many firms, attorneys take turns taking the laboring oar of administration. I thought my turn was up.
Things had also picked back up on the financial end of things. I thought I could buy some time by reducing my salary in exchange for fewer billable hours. This would open up time for Small Business Stories.
During this time, I also moved to a little “farmhouse” in Southeast Idaho. I’m not going to get into that too much here.
But the end result was I had some physical space and had bought some more time to work on the podcast. I was going to come back and figure out how to make it work.
Coming Back for Season 2!
After about a six-month break, I was able to bring Small Business Stories back. This time, however, I knew I would not be eligible for the New and Noteworthy bump (because the podcast was no longer new). I also switched to a once-a-week format.

Fortunately, people seemed to tune back into the show. I was very happy with the downloads and the numbers kept improving.
Just as before, though, I still couldn’t get much interaction. People weren’t going to the website in any meaningful numbers; nor were they responding to my calls to action.
I did get one local business that was interested in hearing my ideas for improving their business. So I thought I might be able to do some coaching. But nothing really came of that.
The End of an Era
I have mixed feelings about the way my podcast ended. While I loved the podcast and I loved being in that space, I did not love setting up interviews and I wasn’t sure how much I was really reaching people.
However, I was sure that I was running out of money and therefore running out of time.
I made a last-ditch effort to figure out how to right the ship by hiring a business coach–one of those online personalities that explain how they have the secret to unlocking financial freedom. My thought process was that even though I knew they were likely overselling their ability to help people, they were in the online space so they must have at least some good advice and technical know-how. I basically put a significant amount of what savings we had to bank on myself figuring this out with the help of the online “guru.”
I didn’t figure it out…
With my back to the wall, I made the decision to lean in on my legal training and I started my own law practice. In doing so, I closed Small Business Stories for good. It just didn’t fit into the equation and, frankly, ended up being a money pit and time drain.
At one point my domain was set to expire. I thought for a moment about renewing it and giving it one more go.
I let it lapse.
Lessons Learned
It’s now been many years since I did that podcast. Oddly, I’ve never taken the time to sit down to think about what I should learn from my podcast experience. It was all just a whirlwind.
I mostly remember how exciting it felt and how proud I felt to be putting those stories out there. I know it was also challenging and frustrating at times, but that’s not the feeling I have from it.
Maybe I should have tried to be more proactive in getting sponsorships. Maybe that would have helped. I’m not sure.
I probably should try to glean some great lessons out of it. If I had, I would be able to tell you what that lesson is. Hopefully I’m not just making the same mistakes again with this project. I actually think I may be making even worse mistakes because I’m not even sure what my niche or message is right now.
Maybe…”Don’t overthink things?”
Even if I can’t point to a specific lesson, I look at it like I tried something, I had a good time, and I enjoyed the journey. I wish it worked out better for me, but it’s a chapter of my life that makes up a part of who I am now.
I’m hoping that that doesn’t mean I’ve become a guy that doesn’t learn lessons.