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The 13 Biggest Failures from Successful Entrepreneurs and What They’ve Learned From Them

Sep 5, 2013 8 min readLife Hacking
failure entrepreneur lessons learnt from failure

One of the great things about our focus on transparency at Buffer is that we get to help other people learn from our experiences.

We love learning from others as well, and since we got so much out of our round-up of counterintuitive advice, we wanted to find out even more about what other people have learned from experience. This time, we wanted to learn about the darkest moments of successful and famous entrepreneurs and what their lesson has been.

Without any further ado and in their own words, here are some of the biggest mistakes and lessons learned from 13 successful entrepreneurs.

1. “We wasted $1,000,000 on a company that never launched”

Hiten Shah, Co-Founder at KISSmetrics

failure entrepreneur lessons learnt from failure

My co-founder and I spent $1,000,000 on a web hosting company that never launched. We were perfectionist so we built the best thing we could without even understanding what our customers cared about.

We have now learned to spend smart, optimize for learning and focus on customer delight.

Hiten has since co-founded two wildly successful analytics companies with KISSmetrics and Crazy Egg

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

Robin Chase, Co-Founder of Zipcar

failure entrepreneur lessons learnt from failure

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.

Robin is the Founder and CEO of Buzzcar and also the founder and former CEO of Zipcar

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

Rand Fishkin – CEO of Moz and Co-Founder of

failure entrepreneur lessons learnt from failure

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.

Don’t be like us – use agile development, have lots of visibility into progress, and keep your team accountable to each other.

Rand Fishkin is the CEO of Moz and co-founder of

4. “I started too late. I toiled in a job I hated for a long time.”

Leo Babauta – Best-selling author

failure entrepreneur lessons learnt from failure

I started too late – because of fear of failure or a lack of belief in myself. I toiled in a job I hated for a long time, instead of starting a blog or building a business I loved.

Knowing what I know now, I’d have started a decade earlier. Not starting is the worst-case scenario.

Leo Babauta is a best-selling author and an entrepreneur


5. “I tried to do it all by myself”

Leo Laporte – Founder of the TWiT network

failure entrepreneur lessons learnt from failure

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.

Leo Laporte is the founder of the TWiT network and host of The Tech Guy and This Week in Tech

6. “If you’re not 100% excited, say no”

Tim Ferriss – NYT Best-selling author of 3 books

failure entrepreneur lessons learnt from failure

Committing to too many ‘cool’ opportunities and projects. I think it’s important, as Derek Sivers (founder of CDBaby) would say, to either say ‘Hell, yes!’ or a flat ‘no’ to things. They should be definitive and binary.

If you’re not 100% excited, it should be a decline.

‘Kinda cool’ will fill up your calendar and leave you wondering where the last year – or 10 – went.

Tim Ferriss is the best-selling author of The 4-Hour Workweek and an entrepreneur

7. “I’ve let growth exceed my own ability to fund my business”

Michael Hyatt – NYT best-selling author

failure entrepreneur lessons learnt from failure

In 1992, I made the mistake of borrowing money to fund my growing company. Unfortunately, I did not understand the difference between rapid growth (like cancer) and healthy growth (normal cellular reproduction). Eventually, our growth consumed our capital and the business failed. I learned an important lesson:

Never let growth exceed my own ability to fund it. If I am tempted to seek outside funding, it is a sign of a flawed business model.

Michael Hyatt is the New York Times Best-selling author of Platform and also a serial entrepreneur

8. “Spreading myself too thinly over too many projects”

Neil Patel – Co-Founder of KISSmetrics

failure entrepreneur lessons learnt from failure

One of the biggest lessons I learned was not to spread myself too thin. Like other entrepreneurs I love trying to do multiple things at once.

But once I learned to focus all of my time and energy into one business, I was able to make it grow faster than all of my previous businesses.

Neil Patel co-founded KISSmetrics and Crazy Egg

9. “I built a product without understanding the market or the users”

Sandi MacPherson – Editor-in-Chief, Quibb

failure entrepreneur lessons learnt from failure

Last year, I spent 6 months building a product I wouldn’t use very often, in a market I wasn’t familiar with, for users I didn’t understand – big mistake.

It made it extremely difficult to figure out why things were or weren’t working, and I ended up creating a product that no one wanted.

I could never become the product expert, which is what every founder/CEO needs to be.

Sandi MacPherson is the Editor-in-Chief of Quibb

10. “I made the big mistake of being a ‘parallel entrepreneur'”

Dharmesh Shah – Co-Founder and CTO of HubSpot

failure entrepreneur lessons learnt from failure

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.

Dharmesh Shah is a Co-Founder and CTO at HubSpot

11. “Protect your company culture”

Derek Sivers – Founder of CD Baby

failure entrepreneur lessons learnt from failure

Protect your internal culture, no matter what.

Once it turns nasty, it never goes back. Fire a rotten apple immediately.

Note from Belle: Derek wrote a great blog post about this which expands on how he felt after having issues with his company’s culture. Here’s a little snippet:

I cut two chapters out of my book because they were too nasty. They vented all the awful details about how my terrible employees staged a mutiny to try to get rid of me, and corrupted the culture of the company into a festering pool of entitlement, focused only on their benefits instead of our clients.

Afterwards, I spent a few years still mad at those evil brats for what they did. So, like anyone feeling victimized and wronged, I needed to vent – to tell my side of the story. Or so I thought.

So do you want to know the real reason I cut those chapters? I realized it was all my fault.

I let the culture of the company get corrupted.

I ignored problems instead of nipping them in the bud.

Derek Sivers is a best-selling author and entrepreneur

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

Noah Kagan – Chief Sumo, AppSumo

failure entrepreneur lessons learnt from failure

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.

Noah Kagan is Chief Sumo of AppSumo

13. “People really are everything in business”

Jesse Jacobs – Founder, Samovar Tea Lounge

failure entrepreneur lessons learnt from failure

One thing I’ve learned over 12 years running Samovar Tea Lounge is the importance of having the right people on your team.

It’s worth the extra effort to find the right investors, employees, and vendors who believe in your company’s mission and passionately desire to contribute to it – not just those who want to punch the clock or get their share of profits. People really are everything in business, and the people you align yourself with will either buoy you up or weigh you down.

Jesse founded Samovar Tea Lounges with the mission to enrich people’s lives

Image credits: 500 Startups, Urban Land Institute Washington, Businessweek, The Fetch, Return of Kings, Moz, Ribeezie, Zen Habits, BostInno, Derek Sivers,, Flickr

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