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
“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
“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
“Hiring too quickly and firing too slowly.”
Andy Beal
“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
“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
“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
“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.
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