Do You Make These Mistakes? 6 Questions to Guide Your Next Business

What do Jay-Z, Winston Churchill, and Oprah have in common?

All of the names listed were considered failures early in their careers: Jay-Z couldn’t get a record label to sign him. Winston Churchill ruined his political career and was deemed a political outcast after his mistakes during Gallipoli. Oprah was not only fired from her first job, but was also told that she wasn’t fit for television.

Looking back, it’s hard to imagine these renown figures as anything but successful. Now, Jay-Z is known as one of the best rappers alive and is worth about $1 billion according to Forbes. And did I mention that his wife’s name is Beyonce? Churchill probably won’t sell any rap albums, but he is credited with saving the British Empire from complete defeat during World War II. He’s also remembered as one of the greatest orators ever produced. Finally, we have the infamous t.v show host and philanthropist, Oprah. Need I say more?

The most important part of any journey is to learn from your past experiences by reflecting, then correcting course. 

In this article, I’m going to share stories from several of my failed ventures that have taught me valuable lessons and put me on the right path. Collectively, these failures have shown me how to ask the right questions when I’m jumping into something new.

1. How can I test this idea?

Some people believe that if you build it, people will come. In my experience, this couldn’t be further from the truth. One of my early attempts as business was a book geared towards teachers on how to become more efficient. I thought for sure it would be a hit because I saw so many of my fellow teachers struggling with all sorts of things. This idea mostly failed, however, because I didn’t do any market research outside of this observation. In retrospect, I should have surveyed teachers at my school (at the very least) and elsewhere to see if they viewed this as a need. Maybe it was, but perhaps I needed to package it differently. In the end it was a bust, but the experience was invaluable.

I learned that before jumping into any venture, it’s important to test the waters. This can be done by sending emails, conducting surveys, looking at data online, and even placing ads. Based on the responses you get, you will know whether to pursue it or not before you spend your time building.

2. Is it just about the money?

Wait. Isn’t the whole point of business to make money?

Yes, but it might not be the right long term fit. Of the many ventures I’ve tried, two come to mind for this example. In both, I learned my lesson by testing the market before jumping in. I started a landscaping company as well as a website design business. Although I actually made money with both, I hated every minute.

It was great to have money in my pocket, but I noticed that for me, it was about more than just money. For me, in order to sustain success long term I needed to be passionate. Some people are driven by money, if so please ignore, but if you’re like me you should consider the next question.

3. Does this make me jump out of bed in the morning?

Knowing my personality, I’ve found that I can’t stay with something if it doesn’t make me happy. What I’ve found is that there’s a difference between a good cause and a passion. One of my startups was a course designed to train student athletes and prepare them for college athletics on and off the field. It never went anywhere, but not because there wasn’t a need. It wasn’t something I really cared about, so when it came time to put in extra hours, travel, do sales calls, etc. I just lost all my steam. It felt like life was being sucked out of me and I wasn’t willing to keep doing those things because I didn’t care enough about the product. In my opinion, selling isn’t hard if you like what you’re promoting. In contrast, I felt disingenuous trying to promote something that didn’t make me happy, even if it was a good product.

Some people will probably comment that I should’ve hired that part out if other parts were working. It honestly might’ve been a good idea, however in my heart I feel that the business would’ve failed down the line because I never wanted to go above and beyond for it. 

Before you commit, make sure that it’s something you can do around the clock, think about all the time, and love every second of it.

4. Is this the right partnership for me?

This one applies to relationships and business. In anything that you do, choose your partners carefully. In connection with my idea to sell a program for student-athletes, I also had the bright idea of partnering with a friend of mine’s gym to train athletes. My role was simple, help the kids prepare for the academic side of college while my friend and a third partner trained the athletes. It seemed like a perfect marriage of skills, but boy was I wrong.

The partner who I wasn’t as familiar with owned a majority of the company, so it felt like I didn’t have a say. He would make changes and both my friend and I would just roll our eyes. We never addressed the problem head on until it came too late. I learned that communication is crucial. Make sure you lay out all expectations, discuss roles in depth, and genuinely trust the person you’re partnering with.

5. Do I have good systems for hiring and outsourcing?

If you want to expand your business, you have to have good systems for hiring and outsourcing. By failing to put in the time upfront to get this right, you are guaranteed to fail. Case and point: The Social Teacher. This was my billion dollar idea to make a LinkedIn for teachers–in case you’re wondering, I’m not a billionaire. The problem with this business was that I always chose the cheapest option when hiring. When building the website this led to almost having my credit card information stolen by a rogue coder who decided to hack me.

Yes, that actually happened.

Another really fun part of this adventure was interviewing and hiring interns. At the beginning, I didn’t have anything set up for them to do, I just thought it would be cool to have them. They were super flaky and never panned out…except once.

When I finally learned from all of my horrendous decisions, I found that creating detailed guides on how to do things was crucial. In addition, I made interns and future coders perform tasks for me to prove that they were competent and timely. Perhaps the only positive of this venture was developing a relationship with an intern who then went on to Columbia grad school and now programs video games for a major corporation. It took a lot of practice, but if you make the right hires, you can grow exponentially and free up more of your time.

6. What is the single most important thing I can do right now?

It took me several attempts at business to realize that I should focus on One Thing, just like Gary Keller recommended. My problem wasn’t necessarily focusing on one thing at a time, it was deciding what was most important.

Many times, the single most important thing will evolve as your business grows and has new needs. Generally speaking, however, your one thing should be to figure out what will make you money and put all your effort into that. This could be acquiring users, making sales calls, finding tenants for rental properties, it all depends on the business. The commonality with each of the aforementioned examples, however, is that the one thing provides revenue. Without getting paid (or getting funding) your company can’t survive.

Final Thoughts

Success is only the tip of the iceberg. Beneath the surface, there’s plenty of hard work, internal struggles, and mistakes. Hopefully, by learning from my life lessons you’ll be able to get to your final destination with a few less bumps in the road.