6 Entrepreneurs Tell Us Their Biggest Mistakes

Vinay Patankar
February 10, 2014


Richard Branson Business Mistake 1

Ely Delaney

Automated Marketing Architect

“not building systems from the beginning”

The biggest mistake that I made and that I see from the hundreds of other small business owners I’ve met over the years is around not building systems from the beginning.

I know that when I started my first business, it was all me. I did everything in the business so I didn’t feel the need to document things.

Then I moved into an office, hired staff and was on the move for huge growth. Problem was – even though we started in the right direction, the train derailed pretty fast. My employees were running me, not the other way around. I thought that by giving them the freedom to take control they would help us grow. Instead, I ended up running like crazy, working insane hours fixing a ton of mistakes and ended up hating my company.

Now, giving employees some freedom is great. Let them be creative, but document everything first. Give them a baseline of what’s expected and how things should be done. Then, let them use their creativity to improve on what you’ve already systematized.

That way everyone is on the same page. You know what to expect and they know what’s expected of them.

Even if you’re a solopreneur and aren’t sure when you’ll start hiring your team, document and systematize now. You’ll improve your own productivity and when you’re ready to hire someone you’ll already have your company procedures manual ready for them.

It will save you a ton of time, energy and money…. and I can’t forget… massively lower stress levels!

Erin Pfiffner


“not marketing ourselves”

Ask any of our founding partners and they’ll tell you the biggest mistake Citrrus (@citrrus) made was not marketing ourselves. We were doing great things but didn’t tell anyone about them. A small business can’t survive on referrals and cold-calling alone – we know firsthand as we started struggling in 2013 because that’s what we were doing. Now in our 5th year, we just started focusing on marketing using budget-conscious “Growth Hacking” techniques ( and are seeing massive early returns. Had we been doing this all along, we wouldn’t have been in the trenches. Luckily, we recognized this in time and have fully embraced marketing. As our CEO Jason LaFollette (@jlafollette) puts it: “It doesn’t pay to be humble. You gotta get out there, build your reputation, and be confident in telling others what you are good at.”

Nicole Flores

Studio Savoie

“spending the majority of a startup budget on a professionally designed website”

Being on both sides of the question, the one mistake I see most is spending the majority of a startup budget on a professionally designed website. When it comes to a business website, content is king. A neat, easy to navigate, do-it-yourself site is fine for a bootstrapping business. Plus, re-branding is a fabulous marketing opportunity.

John Drabkowski

Lightning Marketing Group

“trying to “cheat” your way into better search results”

I am the owner/operator of an online ticketing company located in North Miami Beach, FL. My company’s website, Tons Of Tickets, unfortunately, had to be shut down after about 4 years in business. The site received a Google penalty that was caused by an Indian SEO company we regretfully hired to better our online marketing exposure.

From my experience, trying to “cheat” your way into better search results can be one of the biggest mistakes a new online business can make. The use of “black hat” SEO strategies are too risky when it comes to developing a successful company online. It proved to be the demise of the entire Tons Of Tickets domain.

After regrouping and restrategizing, we re-opened the company under a new domain, Red Hot Seats, about 6 months later. Since re-opening, our marketing strategies have avoided the use of “black
hat” SEO companies. Instead, we use other effective marketing techniques like press release branding, social media marketing, and content-based marketing. Through plenty of research and sheer determination, our company has made a comeback in the online ticket industry.

Mark Lenneville

Uniformed Services Health professional Placement (USHPP)

“not firing a relative earlier”

My biggest mistake was not firing a relative earlier. When we hired him, this was the best thing we could have done. He was bright, progressive, insightful, creative and fun to be around because he was always full of energy and enthusiasm for the business and for life. This changed as he got more into the business, went through a divorce and suffered at actually producing in the business. His true personality surfaced. He showed that he was not a team-player, seemed to thrive of creating conflict, was unreliable and lacked the attention to detail necessary to sustain the business as an employee. He was great at helping to get the business started and lousy at keeping it going. We tried to motivate him to “get on board,” but we soon learned this was not going to happen. Two years later, the pain in letting him go was terrible for the business and the family, but it was a decision that was long overdue. We should have let him go earlier, but we failed to do this.

Jeet Banerjee

“launched without a revenue model in mind”

I’m a 21-year-old serial entrepreneur, digital marketing consultant, author, public speaker, and change-maker. I started my first business in high school and sold it two years after growing the business to 15+ employees. Here’s my answer to this question:

When I started, we were so excited about the product that we completely forgot we had to build a business. We launched without a revenue model in mind and that ended up costing us a lot. We got over 12,000 users in a few short weeks and they went unmonetized. Not only that, but we had no idea of testing our monetization ideas and it took us almost 8 months until we finally nailed down our revenue model. Our lesson was simple, plan and prepare properly with everything you know because you don’t know how fast things might play out.

What are some mistakes you have made as a business owner?

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Vinay Patankar

CEO and Co-Founder of Process Street. Find him on Twitter and LinkedIn.

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