6 Business Struggles Entrepreneurs Face & How to Avoid Them

My first business venture failed, so later in college, I started working with a 2 man business as a bookkeeper. Because their business was so small, I wound up doing a lot of different type of work for them, and I discovered incredible similarities between the challenges they faced and the challenges I had faced in my business: In fact I started to realize that their challenges, my challenges and the challenges that entrepreneurs I connect with daily all have a lot of similarities. Since my first venture 12 years ago, here are some of the struggles I faced as an entrepreneur and what I have learned throughout the years:

  1. As a start-up, especially if you’re bootstrapped, you have a constant challenge of convincing would be customers that they should buy from you, before you can responsibly sign a contract with the supplier. And the supplier won’t typically agree to work with you, until they are confident that you have customers.
  2. When you start a business, you have more work than you can possibly complete, so prioritizing is incredibly important. So many entrepreneurs think that any time they spend not generating revenue is a waste, but if you don’t set aside some time to properly set up your infrastructure, you’ll later find yourself forced to deal with these issues, and by then it will be such a mess that it will take you exponentially more time to straighten it all out. Finances, project management, online storage organization, processes, insurance, corporate structure, etc. These are all things that must be done well in order to succeed.
  3. Properly selecting a partner is incredibly important. I’ve made a mistake on that in the past, but I was much wiser the last time around. For some people, it’s better to go it alone, but others need a partner. If you need a partner, make sure you’re careful about who you partner with.
  4. I would also recommend finding local organizations that support entrepreneurs. is a national organization with a local presence in many cities around the country, but many cities have their own groups that are specific to that single city. In Austin, we have Austin Technology Incubator, Tech Ranch, Capital Factory, lots of Industry Meetup groups, etc. There are also many non-profits out there that help microbusiness. A friend of mine started one in New Jersey called Rising Tide Capital; if you can something similar in your area, I highly recommend reaching out. It can only help.
  5. Always be learning and find your passion. If you constantly immerse yourself in learning opportunities and keep an eye out for something that excites you- not just for the money- you will be successful.
  6. If you start a business that you’re passionate about (which I recommend) you’ll have the opportunity to solve problems or add value to the world through your business. You’ll finally be able to do something about all of those things you wished you could change, but were unable because you couldn’t do it alone.

This is a contribution is an excerpt from an interview Leo Welder, founder of, an interactive website that helps entrepreneurs and small business owners face the tough challenges of starting and developing your own company. 

Image courtesy of David Castillo Dominici /


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  1. Many great ideas. Thanks for sharing!
    I'd like to add something that Kevin Koym at Tech Ranch said: The BEST source of capital is a paying client. Ge serious about sales, and the profit and mission will be fulfilled.

  2. I donno really! I started a business few years back with a partner and it was running quite well. But then after few months, business tent to happen! I am using the word business because it started on a friendly note but later on money making. more profit, who’s profit became an issue. I second all other thoughts, but would like to differ with this one. Go alone if you are serious about your business and get the best out of it. It hurts because not everybody is passionate about your dreams, may be only you are!
    Anyhow, Thanks for sharing great wisdom 🙂

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