Last week, I wrote a post about when to “say when” as you pursue your place in the football world. It seemed to strike a chord, especially resonating with the 30-plus crowd, so this week, I thought I’d expand on it a bit, especially as it comes to the last point I made about being entrepreneurial.

You absolutely should be willing to start your own thing. It’s honestly not a lot different from pursuing a job in the NFL, or working atop a P5 football office, or anything else like that. It doesn’t take a genius; I’ve proven you can support a family, live semi-comfortably and follow your passion by going your own way without having any extraordinary gifts. Still, there are a few things I want to share based on my own journey.

• When I launched ITL in 2002, it was only after a mountain of market research and lots of positive feedback. Because of that, I was dumb enough to think our launch on Labor Day Weekend would be so big it would crash our servers. Instead, on Day 1, we got two subscribers. On Day 2, one of them wanted his money back. 
• Our initial subscription price was $250 for a nine-month subscriber cycle (we planned on taking the summer off). After our humiliating start, the week of our launch, I dropped the price to $45 (I announced it as a “sale”). We didn’t get to 20 subscribers until maybe December, even at that price point.
• For the first five years, we grossed about $5,000 a year. Keep in mind that I was hoping this would be my new profession by that time. Basically, I had a small side hustle instead of a new career, and I had no Plan B, professionally speaking. 
• Keep in mind that my “day job” at the Houston Chronicle was making me about $42,000 per year. At this point, I had a wife and two kids. 
• Things went so poorly that in 2007, when I got hired to run the Hula Bowl, I was elated, mostly because I could shutter ITL and move on with my life with some measure of honor. 
• When the Hula Bowl went on hiatus in January 2008, shortly after the game, the main reason I relaunched ITL is because I didn’t have any other options. 

So that’s the bad new. But there are also rewards.

• When I got laid off in 2009 by the Chronicle (I had gone back in 2008 to basically be a secretary), it was sink-or-swim time. At that point, my wife had “retired” from teaching to raise our boys. I suddenly had incredible focus. 
• The “new” ITL was $25/mo., which enraged a lot of people when I announced at the 2009 NFL Combine that we’d relaunch in the fall. I mean, I was mocked endlessly. But by around late November, most of my old subscribers had returned at the new rate. It was then that I realized I might have something. 
• We introduced the first elements of our exam prep program shortly after this. In a few years, we’d turned July — at one time a month I hoped my family could just pay its bills — into our most lucrative month. It still is, due to our study guide, practice exams and video series. 
• Today, I’m not rich or famous, but I’ve built a network of friends and associates that  “get me,” and that I get, as well. My family lives a good life and I have no complaints. I was born to do what I do now.

I don’t think all this happens without a decent idea, an ability to adapt, a will to survive, and God’s grace. In my case, it certainly didn’t happen overnight, but I started it at 33. Youngish, but not a baby by any means. Today, maybe you’re right were I was in 2002. If so, I hope you’re able to achieve the same measure of success.