Fear and Loathing in My Second Startup

Written by Jason Glaspey

Six and a half years ago I started a company that would become my first success. In less than two years, it allowed me to support my family without any other income.

The business was a simple meal planner called Paleo Plan. It was my 6th attempt at an online business. After several years of fizzled ideas and false peaks I had finally quit my job and truly become my own boss.


Note from Chase: This is an article from a Jason Glaspey, a guy I’ve taken a lot of great business advice from over the years. When Jason talks I listen, and this sincere story from him is no exception. Enjoy!


When I started Paleo Plan I was in the shadow of one of those fizzled ideas. After 18 months on that project we still hadn’t shipped, failing to earn even a dollar of revenue.

With that failure fresh in mind I decided I’d try to build Paleo Plan in just three weeks. I did it.

All in, I spent under $1500 to get it going. Unlike the other projects, this one stuck. We got traction, we learned from our audience, we made improvements and, 5 years later I felt tremendous pride and confidence, knowing we’d helped thousands of people improve their health.

That was last year. I was at the helm of my first successful company, and I was getting anxious to start something new. I love to build far more than maintain, and the majority of big problems that I was good at solving had been solved.

So I sold a majority ownership in Paleo Plan and stepped back to invest more time in my next project. I wanted to prove to myself that my previous success wasn’t a fluke or merely an issue of good timing, to see if I could build another successful company from scratch.

When I launched Paleo Plan I didn’t feel tremendous fear or anxiety because it cost so little in time and resources to start it. I’d already failed on several other attempts, so that didn’t scare me. I also was running it as a side project for the first year before it grew to a point that it demanded I treat it like a real venture. In many ways, with that company, I was able to escape the internal demons that can paralyze many entrepreneurs. I had landed on my feet with a functioning company—never giving those demons a chance to tell me I was a failure.

So, last June, when I first vocalized what would come next, I had all the confidence in the world. My new venture—I called it Factory, the name stuck—was obviously going to take more time and capital to get going than my previous company. I knew that going into it, and I was prepared to put out the money to move us forward anyway. We were starting a digital publishing company, and I was convinced we had the right team, the right products, and the right strategy to make things people loved enough to pay for. I even knew how we’d get loads of traffic. It seemed all I had to do was make a few ebooks and everything would start falling into place.

By the way, a couple key differences this time were, 1. my family was already relying on me to be the bread winner, so I wouldn’t have 18 months to see if this would work and I could earn a full income. And 2. I was bootstrapping the company with my own savings, paying salaries, invoices and contractors from my own coffers. Despite this severely increased risk, I had so much confidence from my previous success that I just plowed forward.

But it didn’t quite work out the way I imagined it.

Our first book was a few weeks late. Not a big deal. I was prepared for that to happen. But then we launched and some partners I was sure would be on board with promoting it were a little hard to convince.

It was my first product under this new company and I didn’t have any sales numbers to back up my assertions. The relationships I was counting on were new as well, so despite my previous success they weren’t rushing at the chance to partner with me. At Paleo Plan, it was a totally different market and a totally different type of product, so even though the practices of selling digital content were the same, I had to start all over again with convincing people to trust me (or even just answer my emails).

Soon, we had some issues with our second author, and we had to painfully decide to end that relationship and start from scratch without her. Not a huge financial loss, but it cost us time and a bit of our momentum, as well as some optimism. We were now 2 months behind on our second project.

We’d also made a few small tweaks to our business plan as we went along, which is normal. Our biggest change, however, came when we decided to focus early efforts on one core demographic, building a marketplace just for them, selling both our own content and others’. I still believe it was the right decision, but it meant another 2-3 months before we were in a position to make any revenue progress… which is pretty damn scary when you’re already months behind in revenue and paying for every idea out of your own pocket.

Our first product was selling well, but we were so far from paying our bills that, at times, I became overwhelmed with this fear: I had made a huge mistake. “Our savings account will be diminished. None of these ideas, nothing we’re trying will work.” It wasn’t just a sense of responsibility, it was sharp moments of complete paralyzation based in fear.

Soon, I found myself dreading the office, or worse, almost purposefully not getting anything done when I was at my desk. I found myself actively hoping an email would come in so I would have something to respond to, some urgent but unimportant task to do instead of the things that I knew I should be working on. I’d get wrapped up in Quora posts for an hour or more as I educated myself on all kinds of inane information. I didn’t immediately recognize it, but I had slipped into a type of fear-based depression. And at the end of each day, I’d be completely dejected and disappointed in myself as I walked downstairs to see my family, trying not to let them see how much I felt like a failure.

Then I got a tiny glimmer of hope… and it was huge.

I talked to my wife about how I was feeling. She was patient, listened to me and I was incredibly thankful for how understanding she was. She didn’t make me feel bad or add to my stress, she simply asked what she could do and reminded me that she supported me. It didn’t conquer the fears, but it was a huge help.

Then something weird happened. Sitting on my couch one night I had an idea. Nothing big, just a thought that might help us grow in a tiny little way. It wasn’t much at all, but it had an energy to it, like it was somehow refreshing my attitude. It reminded me that I wasn’t a failure, that I had good ideas, that we were going to put some great things in a lot of people’s hands. It reminded me that I could be optimistic… I just had to be patient.

That small moment with an even smaller idea made a monumental impact on my attitude moving forward. I came out of my funk and I haven’t looked back since. I never would have guessed that it would have made such an impact, but I’m thankful it did.

The idea, by the way, was that in addition to making products to sell, we should also invest in making products that would be free. A tiny idea, nothing important, but it shifted my thinking. It was a way we could show we were in it for the long haul, that we were committed to doing good work. We knew our content was so damn good that we could afford to give some away. That was the company I wanted to build, and this simple little idea reinvigorated my vision. Confidence in the other products resurfaced, I set the fear aside (and the Quora threads) and got back to work.

Don’t be afraid of fear. Acknowledge it and move on.

My biggest takeaway, especially for you Fizzlers out there, is that it’s okay to be scared. It’s okay to occasionally have doubts. We’re pioneers forging new roads and trying new things, and we’re proving to ourselves and everyone else that we have what it takes. Even with success in my past, starting a company continues to strong-arm me into more vulnerability, uncertainty and fear than almost anything else I’ve experienced.

After the success of my first company, I never expected to be afraid again. I thought I was beyond it, I thought I’d just roll right into another success. It wasn’t just cockiness. I trusted myself more after that success. However, the playing field leveled very fast when things weren’t going how I expected, and I became just another player in the game.

I now more fully respect the job of being an entrepreneur. It’s like the ocean — you don’t just run into pounding surf willy-nilly. The same is true with what you’re trying to build… the waves will come. Don’t lose heart.

If the fear, uncertainty and doubt come charging in on you, I can only say this:

  1. Allow things to take time.
  2. Allow yourself to make changes, big and small, to your business plan.
  3. You’re not alone.
  4. In the end, the only thing that assures failure is if you start to believe it enough to quit.

Please, if you read this and find any of it useful, let me know in the comments below. I’d love to hear if my struggle helped you.



Jason Glaspey is the founder of Factory, a publisher designed for independents and the digital age. He’s currently building The Startup Library, a digital library for startups and the entrepreneurs that make them happen.

Image above adapted from Francisco de Goya y Lucientes, 1815.

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