search cancel

13 Startup Challenges (That Make The Rewards Even Sweeter)

by Matthew Ackerson



With near-overnight successes like Facebook, YouTube, Twitter, and Groupon dominating the headlines of the day, it’s time someone injected a bit of reality into the mix.


Everyone has heard exaggerated numbers like “90 percent of new businesses fail,” but few people have recorded specific examples of why getting a real business going (without VC money) is a monumental challenge.


Here are 13 real-world examples I came up with after reflecting on my entrepreneurial career to date:

  • All nighters. I’ve gotten better at this recently thanks to an app my team and I recently developed, but once in a while I stay up and work for 24 hours or more straight. Sometimes it’s by choice, other times it’s out of necessity or worry.
  • Killer stress. If I don’t have to stay up to work, many nights in the past I’ve had trouble falling asleep. It’s usually because I’m planning in my head what has to get done the next day; other times because I was fretting about the company’s cash flow. Most entrepreneurs have similar experience but won’t admit this because they worry they’ll look vulnerable or doubtful in the business’s future.
  • Bankruptcy. I’ve gotten close to bankruptcy in the past due to poor investment choices. Maybe it’s a big deal to admit this, I’m not sure. The truth is, it was an extremely rewarding and humbling experience. It was scary but it taught me how to hustle.
  • Unlimited patience. Clients will get mad at you, team members will make mistakes, and you’ll mess up too. For instance, in the past, a designer on PetoVera‘s team was very late with a project. I could have gotten angry or removed him, but instead I asked questions and realized that (a) he was doing an amazing job of designing the site, which took time, and (b) I should have blamed myself for not planning the project as well as I could have.
  • Living “poor.” After college all of my friends went and got jobs. Pretty much everyone I knew was and still is making more money than me. Meanwhile, since I don’t get a “regular salary,” I’m still counting the cost of that five-dollar foot long sandwich (plus tax).
  • Constant fear of failure. If you fail, all that hard work may seem like it amounted to nothing and you will fail publicly. The “haters” will have won and all those big ideas that you espoused will have been for naught. That fear is always present.
  • Pulling a “Facebook” doesn’t happen. Most of the time. Study those big success stories regardless.
  • People will hate on you. Once in while I get some dumb anonymous blog comment or someone tells me some pointless gossip about what someone else said about my company or me. It’s an unfortunate fact.
  • Most of your victories go unknown. For example, employees won’t thank you for systematizing your business and improving profits or efficiency. The only reward comes in the long run, from happy customers.
  • It’s always your fault. When something goes wrong assume it’s you because it usually is (even if it isn’t).
  • Your family won’t support you. I have a sign with a quote on it hanging in my room from one of my parents. It says something like “You seem lazy, you don’t seem very ambitious, you’re throwing your life away.” I use it for motivation.
  • You have to earn most of what you get. If I don’t wake up one day to make sales calls or go out networking, that is going to have a direct effect on PetoVera’s bottom line. On the upside, to quote Kevin McGovern, “The harder you work ,the luckier you get.”
  • Romantic relationships are tough to maintain. This is especially true when your business isn’t yet “established.”


But even after reviewing all those examples, I still love what I do. Here are 3 great reasons why entrepreneurship still rocks:

  1. You can work from anywhere (or at least you have the option to travel much more than the average person)
  2. You get all the upside.
  3. You build something big from scratch.

Can you provide any more examples, good or bad?

Matthew Ackerson is the founder of PetoVera to solve the universal problem of perfecting the process of making ideas real. As a student at Cornell University, he started three businesses, one of which won Cornell’s Big Idea Business Competition.



The Young Entrepreneur Council (YEC) is an invite-only nonprofit organization comprised of the world’s most promising young entrepreneurs. The YEC recently published #FixYoungAmerica: How to Rebuild Our Economy and Put Young Americans Back to Work (for Good), a book of 30+ proven solutions to help end youth unemployment.


Photo credits / /

Author : Guest Author

Share This Post On