6 Ways To Run Your Company Into The Ground

David Powers
6 min readFeb 10, 2018

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If there’s something that every entrepreneur is bound to experience, it’s failure. Many world renowned entrepreneurs say failure is critical to ultimate success. To lay it out pretty bluntly, I can claim that I’m definitely in the running for what most would consider to be a complete failure.

That car pictured above is what I’d consider my life to be. Within the last year alone I’ve dropped out of college, failed as a CEO x2, and butchered countless work and personal relationships. It’s been an incredibly tough year, and as I’ve worked through these speed bumps, I’ve realized it can be very difficult to determine what is bringing your company to it’s knees when it’s happening.

“Do not be embarrassed by your failures, learn from them and start again.” — Richard Branson

These factors can hide themselves and blend in with commonly small issues, making it seem like everything is alright. Hindsight is 20/20.

Using my experiences over the course of the last year, I’m going to break down six of the ways that I mindlessly ran two different companies into the ground. I’m doing this to help you learn what to look for while you’re building your own empire. No bullshit, no filters. Let’s go.

1. Stick with the idea you started with.

In a sense, you need to stick with an idea if you want it to pan out. What’s difficult is discovering when you need to bite the bullet and pivot. This can mean sometimes scraping the entire idea, starting over, and rebuilding. It’s incredibly easy to get caught up in the, “lets give it one more month” ideology.

While you’re building your company, it’s difficult to admit to yourself that maybe this isn’t going to pan out, we should probably see if there’s an easier way to reach our end goal.

I think time and time again about different avenues we could have taken with both of my business’. That media company I helped start? What if we stopped writing altogether and figured out how to turn all of our content into podcasts? What about videos? Maybe we should have pushed to host live events?

Being against change is the easiest way to fail. You need to be nimble on your feet. There’s no reason why I shouldn’t have put in the work to at least test each of those options. Fail fast, and don’t be afraid to take a leap of faith when it might feel right.

2. Think you know what the customer wants.

Owning a service business, it was very easy for me to simply say that I could just throw myself in my customers shoes and determine if they’d be happy with the product. This is an expensive mistake to make.

Even with the media company, we constantly struggled with which types of content our customers liked the most. We had data, we completed surveys, but I believe we didn’t have nearly enough face to face conversations(this is completely my fault).

It shouldn’t matter how big your company is, success is dependent on whether someone will pay for your product. What’s the only way you can guarantee you’ll have a customer? Go talk to them. Figure out what they like, and more importantly, what they hate.

Use that data to your advantage, make changes, and go back and have another conversation.

3. Have blind trust in your employees.

During my time running The Hum, the company grew insanely quickly. Within four months we had five committed employees. Everyone had their own things, and everyone showed passion for what they were doing. So what happened, why did we slow the pace and lose focus?

I failed to act as the bumpers(leadership) that helped the bowling ball(company) steer away from the gutter(failure) and hit the pins($$$). The mistake I made was thinking the team would be able to get a strike without my help nuzzling the ball gently from time to time.

It’s easy to assign tasks and to develop large goals, but what’s not straight forward is working with each team member individually to set smaller, quickly obtainable goals. This takes almost daily, and definitely weekly meetings. This not only helps break down the daunting task they might have been assigned, it helps you see what issues they are facing and gives you an opportunity to work with them to solve these problems before they become roadblocks.

4. Develop only a basic revenue path.

There’s something about chasing your dreams that makes the money seem pretty irrelevant. The idea that you get to wake up everyday, decided your own schedule, jobs, and priorities can be both a blessing and a curse.

When you’re first getting started in your first business, it’s easy to get ahead of yourself and tell yourself that you understand how you’re going to make money, without actually putting in the work to talk to others who have had to go through the same experience.

Starting a media company? Cool, we know we’re going to make money off ads, but realistically that’s not even close to as easy as it seems. It took The Hum almost 4 months to finally approved and get ads on the site, then the remaining time, we made a whole $46. Fuck.

Do yourself the favor and make you path to revenue the most researched part of your project. Future you will thank you.

5. Let your personal life limit your ability to be a good leader.

Okay, dropping out of school and starting your company sounds pretty cool in theory. Trust me, I’ve been there. You know what really sucks? Dropping out of school to run your two companies, then having them die and becoming flat broke in 6 months.

For me, my relationship with money and school was never the smoothest. I was lucky I was able to skirt my way through 3/4’s of my college career and get by on the small salary I was paying myself with the screen-printing business and help from my parents. When that all fell apart, I was left broke.

I’d be lying if I said being broke didn’t play a huge factor in my mental health during the last 4 months of running The Hum. The constant stress sucked the life out of me, and I was lucky I had such supportive co-founders (who were also my roommates (don’t do this)).

Before you take a dive into the deep end, make sure you get your personal life in order. It will ultimately make your path that much less stressful. Entrepreneurship can suck the life out of you, so start with as much in the tank as you can.

6. Give the customer what they ask for.

This one may seem pretty straight forward, but in reality we live in a world that thrives off overconsumption. People are no longer happy receiving just what they asked for. In order to stand out and thrive, you need to consistently give the customer more than they are expecting.

One strategy I used with the screen printing business that worked wonders was to print a sweatshirt with whatever design was requested and give it to the person who placed the order. I’d say at least 1/3 times I did this, I would have an order for sweatshirts or with another design within 6 months. It’s all about that ROI.

If you want to slowly fade away into the background, focus on giving the customer what they ask for. Want to thrive? Go the extra mile, it’s worth it.

In conclusion

Running your own business can be a confusing, complicated, life changing experience. It’s something that is really difficult to be taught, and the best way to go about learning it to just go for a swim yourself. If you decide to take the leap and want to avoid subconsciously running your company into the ground, avoid these 6 things.

  • Stick with the idea you started with.
  • Think you know what the customer wants.
  • Have blind trust in your employees.
  • Develop only a basic revenue path.
  • Let your personal life limit your ability to be a good leader.
  • Give the customer what they ask for.

If you liked what you’ve read, give me a follow and check out my socials. My twitter game is fire.

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David Powers

Engineering Manager at Advanced.Farm, Former Co-Founder and CEO at The Hum, Former Owner at Bleed True LLC, Management Engineering Student at @WPI