How Hard Times Lead To Success and What To Expect


All too often we see others make it big time without witnessing the struggles it took to get there.  We assume successful people were just destined to get there.  “Anomalies.”  “Good luck.”  “Geniuses.”

I started selling on eBay when I was around 14, totally against my parent’s wishes. I was naively optimistic, and that worried my parents.  But I was so sure I could do well, and that ‘prophecy’ turned out to be self-fulfilling. I did pretty great for a 14-year-old, simply performing arbitrage across several marketplaces.

But things haven’t always gone so well for me.

Fast forward a few years and through a couple other projects. I was a year or two into school and had just completed my first internship in a “real” career. I hated it. To be honest, I was quite immature about the whole thing, but nonetheless…

That experience in corporate America drove me to try and carve my own path. Soon after, I started a business with a friend, having plans to raise seed funding first and later some venture capital.

Now, this business was sort of forced. We tackled one of the most apparent problems to us at the time. There wasn’t much planning to it.

That problem (in our eyes) was bar cover. We were big drinkers at the time; going out several nights a week (NOT a good ingredient in the ‘recipe for success’). At first we thought it would be cool if bar cover started at $1 early in the week and slowly ticked up to $5 as the night approached. Patrons would be rewarded for committing to going to that bar early in the week, and the bar would get a sense for what kind of crowd would show.

Well, we immediately went out and talked to potential users and bar owners (one of a handful of things we actually did right), as well as advisors in the area. We quickly found that the value proposition was really just the ability to pay cover on your phone (rather than in cash), and see drink specials in-app. There wasn’t strong evidence that this was a great idea either, but again, we sort of forced it.

So we found one developer and hired that guy right away for $100/hour. Didn’t know what we were doing but fortunately, he was actually quite talented, and patient too.

Our first iteration sucked. Regardless we signed on a couple bars and got a few hundred downloads. We had a ‘launch’ night and no one showed up!

It was clear that the redemption process for the covers was not intuitive at all. So we fixed it. We also had built this service naively thinking it would kind of sell itself. Surprise-surprise. It didn’t. But we got better on the marketing side over time.

A couple months go by and we push out an update. Spending way too heavily on marketing, we managed to gather 2,000 users and generated $5,000 in sales over the next couple months. We threw promo events that had people lined out the door an around the block.

That was cool. But the other 5 bars who promised to sign on after we ‘beta tested’ didn’t sign on. Without promo events, our sales might hit 5-10 covers on a weekend night with a $.99 up-charge.  Our margin was only 8%, a measly $.52 per sale.

Frustrating.  Then our programmer took a job in Seattle. The only guy in the area who could write code in our app’s languages.

All the while I was drinking too much, taking 18 credit hours, working as an apartment leasing agent 30 hours a week, trying to mend a relationship with my girlfriend, and raising an 80 pound (unexpected) dog in my 4th-floor apartment.

I broke down. We called it quits. Rock bottom, for me. Depressed for several months. In my mind, we had failed. I also lost $5,000 (significant for me at the time).

I kept going through the motions of life. Still going out and drinking, spending money I didn’t have. Watching Netflix and playing video games in all of my spare time. Dropped a couple classes.

Fortunately, the story landed me interviews with about 12-15 great companies. Every single one I wanted rejected me but the very last one, which had 3 rounds. I was surprised to pass the first, as I had a severe cold, but it reinvigorated my confidence for the moment and I killed the second and third.

That didn’t stop the depression and anxiety by any means. I traveled to a city away from all of my friends to work for the summer. I spent a lot of time alone, including at work as it was a field sales role. But management at that company was amazing. I met a lot of positive, inspiring people and learned a ton that summer.

That summer served as an excellent reflection period. It wasn’t pleasant to reflect on that failure and issues in my personal life while also spending so much time alone. But it was healthy, I think, in the long run.

After that internship/summer I wasn’t fully ‘alright’, but the entrepreneurial itch just wouldn’t leave me alone. I got back into the online space (drop shipping, affiliate marketing) back at school and profited $1,000 in my first month. Not a lot, but it was the fastest I had ever profited. The rest is history.

I learned a lot in those 6 months and the following reflection. A lot more than $100,000 in tuition and 4 years in the classroom could ever teach me about business, or myself.

The hardest part was the overwhelming amount of uncertainty. The right decisions were never clear; the path was so ambiguous. This paralyzed me. 90% of the hundreds of hours I put into this project were spent in a state of what I call analysis paralysis. Frozen by indecision.  It was very uncomfortable.

These days, I’ve learned to accept and even chase those uncertainties. Getting out of your comfort zone usually means tremendous opportunity for improvement. You learn make the best decision you can without thinking too hard, moving on to the next, and fix things as you go.

If you’re looking to start a business or you’re in the trenches as you read this, just know that there is never a ‘right answer’.  What should I sell?  Does this logo look good?  How can I market this?  These are questions experts face daily, just like you.  We don’t allow the absence of a ‘correct answer’ to stop us, rather we do the best we can and move forward.  Hindsight is 20/20, so fix it later.

Show up every day and give it your best effort.  If you can manage to improve just 1% each day, that daily 1% will compound.   You will be 1.01^365 =  37.78 times better than when you started, just 1 year later.

So, move fast and break things.