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Why Failed
The Biggest Failures From Successful Entrepreneurs

Top 5 Biggest Failures From Successful Entrepreneurs And What They’ve Learned From Them

1.“I made the big mistake of being a ‘parallel entrepreneur’”


dharmesh shahDharmesh Shah – Co-Founder and CTO of HubSpot

Here’s my biggest mistake: After having bootstrapped a reasonably successful software company ($10M+ in revenue) I mistakenly thought—Hey, I’ve got a team in place, the company doesn’t really need me, and I’m sort of bored and want to do something new. So, I made the big mistake of being a “parallel entrepreneur”. Trying to head up two different startups at the same time.

This was a huge mistake at many different levels. Turns out, startups are an all-consuming thing. You can’t be all-consumed by two companies at the same time – it just doesn’t work.

My original startup team (the team I had recruited personally) felt abandoned. My new startup (the one I angel-funded) didn’t feel enough pressure to find product market fit and get revenues.

So, my advice: Don’t do what I did. Don’t ever, ever, ever try to ride two horses at the same time.

It does’t work, and you’re going both a disservice. Even with complete, total focus, most startups fail – to divide interests across them basically guarantees failure.

2.“One of the biggest mistakes we’ve made at Moz was to build “big bang” projects”


ran-dishkin Rand Fishkin – CEO of Moz and Co-Founder of

One of the biggest mistakes we’ve made at Moz was to repeatedly build “big bang” projects that required many months of development time without much visibility into progress. It’s sad because it actually worked a number of times, before we fell flat on our faces with a recent project that started in Q4 of 2011, was initially supposed to roll out in July of 2012, and has now been delayed until (fingers crossed) September of 2013. Missing something you budget and plan for by more than a year is really bad news in the startup world.

3.“We built the website first and asked our customers about it later”

Robin Chase Story

Robin Chase, Co-Founder of Zipcar

Get to your customers as fast as possible & learn from them to build your product.
With my second company, GoLoco – social online ridesharing – we spent too much money on the website and software before engaging with our first customers. This meant that part of our learning was undoing our first guesses.


4.“I tried to do it all by myself”

Leo Laporte Story

Leo Laporte – Founder of the TWiT network

My biggest mistake was trying to do it all myself. As a founder I felt like I knew everything I needed to know about media, content, even the technology involved to reach my audience. And I did. I just didn’t know anything at all about making a viable business: finance, marketing, advertising, and human resources.

After a few years of rapid growth my company had stalled out, and I was spending more time fighting fires than I was doing the stuff I loved (and that made us money).

Hiring a business partner then giving her full scope to do her job felt a little like giving up my company but it was a vital step toward success.


5.“I put myself before Facebook, it cost me $100,000,000”

Noah Kagan Story

Noah Kagan – Chief Sumo, AppSumo

When I got fired from Facebook, it was my entire life. My social circle, my validation, my identity and everything was tied to this company.

As the company grew, I wasn’t able to adapt. One of the reasons why was that I was selfish.I wanted attention, I put myself before Facebook. I hosted events at the office, published things on this blog to get attention and used the brand more than I added to it.

Lesson learned: The BEST way to get famous is make amazing stuff. That’s it. Not blogging, networking, etc.

Source : bufferapp

Swathi K


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