failure entrepreneur lessons learnt from failureOne 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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Written by Belle Beth Cooper

Belle is the first Content Crafter at Buffer and co-founder of Exist. She writes about social media, startups, lifehacking and science.

  • Really inspiring stuff. What makes everyone on that list great is their ability to learn from mistakes. Neil Patel is working on a lot of things to this day, but looks like he knows how to manage much better.

    • Belle

      Thanks Vincent! Definitely agree with you there 🙂

  • Soluciones Web

    Very good post, really helpful. Thanks for sharing.

    • jaen

      my Aunty Eleanor recently got a year 2012 Mercedes E-Class Sedan only from working off a macbook… Find Out More


  • Amazing post!

    • Belle

      Thanks Niel! It was a fun one to put together 🙂

  • Andrew Mastrandonas

    Great post! I think I’ve seen a lot of what’s mentioned in my own work as an entrepreneur.

  • Guest

    Love this post especially this quote “If you’re not 100% excited, say no”

  • Excellent post Belle! “If you’re not 100% excited, say no” – Truth!

    • Belle

      Thanks Pauline! So glad you enjoyed it!

    • Casie [kay-cee; KC]

      I ABSOLUTELY need to adhere to this, “If you’re not 100% excited, say no.” mentality — it really SHOULD be that easy! Once I hit send…I’m writing that down on a sticky note and committing it to memory. Fantastic post, Belle!

  • michael

    This AMAZING! I love the research you did, the presentation and feeling. Every person teaches you something valuable about life, business and yourself. This is one of your best Belle Beth. Thank you.

    • Belle

      Wow, thanks so much Michael! So great to hear that you enjoyed this one, I definitely had a ball putting it together and learned a lot! 🙂

  • Grant Tilus

    Great job bringing all of these insights to live in one place. A perfect piece of content.

    • Belle

      Thanks a lot, Grant! Really glad you liked it.

  • Rick Gladwin

    Great post. As a business owner looking at new projects, I’m currently struggling with the “riding two horses” question. But it’s nice to think about all these projects and still feel 100% on board.

    • Belle

      Thanks for reading, Rick. Hope the post was helpful! 🙂

  • Przemek OLESINSKI

    Great REAL post.

  • Very interesting post: thanks for putting this together! I especially love: “I could never become the product expert, which is what every founder/CEO needs to be.”

  • Charli

    I have witnessed a couple of these fails first hand. Great article.

  • Valerie

    This was very helpful, as I just started a business and have absolutely no experience doing this sort of thing. Im creative and look through artistic eyes, the business side of things is new to me and a little scary. However I am enjoying everything I am learning and appreciate everyone sharing their experiences as it makes it a little less intimidating. I especially love that each business owner humbled themselves yet didn’t give up. Thanks for this write up.

  • Great article Belle. We’re not the biggest design agency in Cardiff but I feel proud to have taken the step, nearly 10 years ago to start a business, regardless of the risks and mistakes. It’s great to hear that even successful entrepreneurs make errors in judgement. Proof positive that we should all give it a go!

  • Shaan

    As a serial entrepeneur I can relate to most of those comments and having bought or starting businesses I knew nothing about you learn a little bit at every hurdle during the journey.there is no one who can say I know everything and that is why I am successful. I am still learning and still make mistakes but except that you will make mistakes and the journey becomes that much easier.Every business has different challenges and there is no written formula which tells you how to run a business.No degree in business management etc can prepare you for the real life learning experience.

  • Tshepo Mongale

    My biggest mistake was not managing cash-flow and put more time than necessary on ensuring the client gets the best. This back-fired on my face when I realized I can’t finish off a big project due to dried-up funds. This did not only cost me money but also trust from my biggest client.

    Don’t try, make it a point that all fields are taken care of. Most entrepreneurs unlike me fail because the focused on cash flow and let employees relations and product relevance slip.

  • aravis89

    Is one of the best posts that I read recently and believe I read many of them. In either case Belle great job, especially the tips by Leo and Tim was invaluable.

  • julian finlay

    ok queen i will give you an eye and an ear or two

  • Well done Belle, concise and powerful. Leo’s comment resonated the most. I started down my journey after being encouraged by a friend full of ideas and optimism. He has still not started in on any of them (2 years later) and works at the job I left to pursue my dream full time.

  • Lala

    This is an excellent post! Totally agree with the company culture! It is important to hire employees that have the best interest of the company at heart even when it gets tough.

  • Nawel Nanou

    Thank you for this awesome post, it’s really inspiring, I think everybody should use his failure to do better, and we should apply that in our daily lives. I’ve read so many blog about success on, this one should be included.

  • Guest


  • Nawel Nanou

    Thank you for this awesome post, it’s really inspiring, I think
    everybody should use his failure to do better, and we should apply that
    in our daily lives. I’ve read so many blog about success, this one is really awesome.
    Nawal Nanou, intern at

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  • Salar Lk

    Great post. I’m currently working on my own app and I’ve got to say its going to be a game changer. About the 100% excitement, I definitely agree and that’s only if you are sure that your app is going to be like no other. As a fresh business graduate, I know I still need a reliable financial plan. However, good luck to all the others as well ! 🙂

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