Last week I had the opportunity to attend the DFJ CEO Summit in Half Moon Bay, California. It was a wonderful event featuring over 150 CEOs from every type of company you can imagine. I was privileged to share war stories with CEOs in all stages of funding, from those who just closed their first round to those who had billion dollar exits.

The experience inspired me to reach out to some other CEOs to capture their thoughts and share them with my readers. I asked a small set of entrepreneurs to answer two questions:

1. What is the biggest business mistake you have ever made?
2. What advice would you give to a first time entrepreneur?

I am going to provide the answers to the first question today, and the answers to the other later in the week. I know many of you are entrepreneurs or have entrepreneurial aspirations. Hopefully this guidance will help you along your way.


Q: What is the biggest business mistake you have ever made?

Tim Draper

Partner at DFJ

“The mistakes I have made have been for what I have not done, not what I have done. We have passed on or not offered high enough valuations for some great companies.”

Gary Vaynerchuk

CEO of Vaynermedia and Author of Crush It

“I don’t really look at mistakes the way a lot of people do because I don’t care as much about the money as other people do.  The process is what really excites me, so even if I do something and it doesn’t end up being financially successful, the learning experience and the fun I had always make it worth it.

Because of that, the only things I would really consider mistakes are opportunities I didn’t take.  I’m known a lot for Twitter and I saw in early ’06 how much of a game-changer it was going to be, but I never invested in it.  That’s looking like a mistake now.  Even that mistake, though, was a process that I learned from.  Now I’m investing in internet start-ups that I really believe in, so it’s possible that not investing in Twitter opened up greater opportunities in the end.”

Chris Brogan

President of New Marketing Labs and Author of Trust Agents

“My biggest mistake was (and still is) saying yes too much. I accept too much. I take on too many things. I get worried that I’m going to miss out on something. ”

Tony Hsieh

CEO of

“Hiring too quickly and firing too slowly.”

Andy Beal

Founder at and author of Radically Transparent

“Forming a business partnership and moving forward on someone’s word–and not a written contract. I learned, the hard way, that however nice or sincere someone appears, you should always cross every “t” and dot every “i.” People change, business circumstances change, and people’s memories can get fuzzy, but a written contract never lies. Even if it feels awkward to put things in writing, always do it!

Gal Trifon

CEO of Eyeblaster

“My more significant mistakes are related to hesitations in making changes in malfunctioning areas. I was never sorry for actually making changes, just for waiting too long to do so.”

Micah Baldwin

CEO of TakeComics

“The biggest business mistake was believing that I could do it all. When starting a business, there are usually one or two people, and everyone wears every hat. Yet, as the company grows, it becomes too difficult to do it all. For me, I was uncomfortable with allowing anyone but me manage the books (after all it was my money!) and pay the bills. So what happened? Bills went unpaid, taxes were done wrong, and overall it was a big mess. The best entrepreneurs believe they can do anything, but understand that the best course of action is to not do it all. Trust others, and your business will grow faster and bigger.

Marcelle Turner

CEO of MindComet

“The biggest mistake I’ve ever made as a business manager or entrepreneur is allowing myself to become too far detached from the day-to-day operational aspects of the business. Having trusted management partners is critical, but having to rely solely on their interpretation of data or situations (especially in siloed departments) can be detrimental to both you and your valued team. Having a firm understanding of daily activities (bank balances, staff sentiment, sales pipelines, etc.) takes nominal effort once you get used to it, and will allow you to collaborate with your team across multiple disciplines to make more informed, holistic decisions.

How about you? Do you have some knowledge to share with other entrepreneurs? Please drop some knowledge in the comments.

Ted Murphy

Ted Murphy

Ted Murphy is an American entrepreneur. He is currently the Founder, Chairman, and Chief Executive Officer of IZEA, a technology company that provides software for influencer marketing.


  • digijoe says:

    Golden insights… One thing Tony from Zappos said at the PubCon keynote is that his other biggest mistake was not firmly instilling the company culture at Zappos until 2-3 years down the line. He fixed it pretty quickly thought – now Zappos is probably the utlimate model for setting company culture.

  • Chris Brown says:

    My biggest mistake was trusting someone with too much responsibility over the business accounting. No matter how well someone seems to be doing their job, ALWAYS meet at least once a month to go over the books with them to make sure things are going the way you are being told.

  • Kathy Rees says:

    If you don’t have time to read Gary’s new book Crush It, you can get the cliff notes here

  • Mahmud Ahsan says:

    Thanks for such a nice interview!

  • […] in business Yesterday I did a post that featured eight entrepreneurs who answered the question what is the biggest business mistake you have ever made? Today I am sharing the second part of the series, with a follow up question for the same group of […]

  • Steven Hess says:

    The biggest mistake that I made in my new business was not trusting the people I hired. I preferred to conduct all of the financial matters, but it is unrealistic once the company grows beyond a certain point. As the head of the company, my advice is to hire people to do most every job and you can devote all of your time checking over them and keeping the company organized. Although this will be unlikely to cause the collapse of a company, for the stress level that comes with trying to do everything, it is not worth it. Get an accountant for money, a janitor for cleaning, a secretary for all of the numerous jobs that a secretary does at her desk.

  • JKrishna says:

    Very useful post for a new enterpreneur like me. The different posts on mistakes made by so many established enterpreneurs will act as guide. Knowledge about these mistakes will help people like me from repeating them. As I have learnt a good lesson about entering into prtnership agreement. I have recently entered into a partnership agreement and as the person is well-known to me for several years, no written contract has so far been made.But reading this post has opened my eyes. I will make a written agreement to avoid future hazards. A contract in writing will go a long way in saving me. Thanks a lot for the esson I learnt.

  • Big Bob says:

    I didn’t have just step by step manual to success. My It is my BIG mistake. So knowledge is power. Learn more – it is key to be successful.

  • hubdawg says:

    I was young and naive and wanted to start a business. I read a lot of self help books lots of articles manuals etc. I took their advice because I had no money and rounded up a group of my like minded friends who believed in my idea. We all pitched in , all different ways. Most wanted to put some money in. Some wanted to help. In the end three years later I was the only one left holding the bag. Everyone else ran up all the bills and passed the buck to me and basically lost interest and vanished. I would have ot say I think it was a huge mistake to enlist friends.

  • I’m sure that not getting help early on from others and seeking their seasoned advice led me to understand more fully the value of coaching and why I became a Life and Career Coach.

    The old expression, “no man (or woman) is an island” I have experienced and because of doing things alone I made start-up mistakes. This saying hangs around in my consciousness to remind me there are folks who have been there, done that and I don’t have to figure it out myself.

  • […] person. Of course he is born in this earth only but somehow lucky (or brainless or shameful or biggest mistake or whatever) to manage all these things. After reading fully, try to predict […]

  • maxw says:

    It is always good to know that other people make mistakes, too. Thanks for the insights! Therefore I want to share my biggest mistake, although it is very similar to the one from Micah Baldwin. I always thought I can do everything on my own just when I work hard enough/acquire the knowledge and so on. That didn’t work out. It’s no shame to let other people handle specific tasks for you when you don’t have the time, energy or knowledge. So don’t worry when you are at the point where you have to find people who should work for you. There’s a reason why they do this job and you don’t – because they can.

  • TG says:

    What a post. I liked it very much. When we look at rich people, we just despise them and say bad names to them without trying to understand what it takes to reach at the top. They only reach at the top that are capable of fighting against the odds. All the above-mentioned entrepreneurs have learned from their mistakes and that’s what made them successful. Entrepreneurship is not about doing something new but it is all about learning new things and growing, keeping your main goal in front of you. Indeed, it was an interesting post. Thanks for the information.

  • Biggest mistake = business dealings with family without legal contracts.

    Andy Beal hit the nail on the head – get it in writing, no matter who you are dealing with or how much you feel you can trust them. Life changes…

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