Maria Shriver

Three of the Biggest Mistakes I’ve Made as an Entrepreneur

By Julie Wainwright

Follow @therealreal

As a CEO, I read articles on leadership and profiles of corporate executives and founders every week.

I’m always looking for new nuggets of gold, hoping to avoid their mistakes and embrace their key success tactics.

Most articles seem to parrot a good self-help book or state the obvious, but still offer a good re-enforcement of key issues we all face.

Seldom are these articles written by women, though. That shouldn't surprise anyone -- there are very few female CEOs.

I believe women can offer a slightly different take on entrepreneurship than men and therefore, I was excited when I was asked to write this column.

Here are my top mistakes and key learnings after 25 years in various corporate leadership positions, mostly in the technology world.

1) Do not let others define you.

Here is what I have been told to my face as I progressed through out my career:

In my teens and 20’s: “You are too pretty to be in business” – Said by my second boss, a woman. “Don’t worry, you aren’t that pretty...better focus on your grades.”- Said by my friend, Stu.

In my 30’s and 40’s: “You are one of the top tech business women in the SF Bay Area.” – said by a reporter. “You are one of the best marketers I have ever met.”- Said by a reporter. “Your company is noted as one of the worst disasters, ever.” – said by several reporters.

In my 50’s: “You are too old to start a company.” - said by a male venture capitalist in his 30s. “You haven’t really done anything for the last ten years, your past experience is irrelevant.” - Said by a recruiter. “Your idea for The RealReal is genius.” – said by a reporter. “Don’t thank me, I didn’t want to invest in your company. I’m the one who voted against your company.” – said by a senior partner in a venture capital firm that invested in my company.

You get the idea. I’m either pretty or not so much, a cheater or a genius, on the top of the pile or digging out from the worst disaster ever.

Now, here’s the mistake I made. I actually bought into the bad bits in my 40s. After I closed down Pets.com, one of the first ecommerce sites in the world, I read the bad press and started owning it. I had failed equaled I was failure in my mind. I fell into a depression that plagued me for over two years.

Do not let others define what you are, ever. I had to re-learn that lesson. Once I did shake off the negativity, nothing could hold me back.

As an entrepreneur, you will be told by many people that you will fail. Or you might be told how amazing you are. Do not let these comments soak into your psyche. The negative will kill you faster than the positive, but the positive ones will blind you to the truth of the business and ultimately wound you and your business deeply.

Be true to yourself and your process. Use objective measurements to evaluate your business results and review your work against those goals.

2) Learn from the past and move on.

There will be another win in your future, probably another loss and hopefully many more times at bat. As I mentioned above, after Pets.com, I embraced the failure of the company and did not move past its failure for a couple of years.

It didn’t help that I had the press and various web bloggers constantly commenting on Pets.com. The company became the icon for dotcom 1.0 implosions, the poster child for failure and I internalized this.

I felt like a freak at social events. I had men who wanted to date me because I was infamous in my own little world and I had reporters follow me out of the hairdresser to ask me taunting questions. It was surreal and ugly and forced me into a more insular life.

So, as my great grandmother might have said if she was still alive, “You had reason to be miserable, but suck it up and move on.”

I couldn’t see past my failure and then oddly enough, sports started to save me. I started studying the baseball players’ statistics of the San Francisco Giants. Winners barely broke a success rate of 30% and if they did they were considered rock stars.

And, guess what? The SF Giants were (and are) amazing. Women and men who play sports know that you have to show up to win, that consistency over time can make you formidable and that you can’t win the next game if you are still beating yourself up about the previous game.

3) Take care of yourself along the way.

Starting and running a business is all-consuming. You have customers, employees and competition to worry about all of the time.

The technology is never quite right, the business always needs improvements and there is never, ever enough time in the day. Figuring out how to keep yourself healthy and somewhat balanced is one of the hardest things you can do.

I always let myself get subsumed by my businesses and not until the scale groans or the dark circles under my eyes look like I’ve had them tattooed onto my face, do I stop and recalibrate.

I never do this right, but I am getting better. I now set my own goals each month and review them. I am trying not to get side tracked by interruptions and priorities that do not match to my short term and long-term goals. My process is mostly working.

These life lessons along with deep operational experience lead me to start a new business 18 months ago, TheRealReal.com.

The RealReal.com, a luxury designer consignment store, online only, is already the second largest reseller of luxury items outside of eBay. Employing over 100 people, the company is dynamic, fun and always challenging.

Starting your own business is tough, there is no doubt about it. It is also rewarding and the most creative endeavor you may ever face.

Remember to listen to yourself and your customers and then just make it happen. The worst that will happen is that you will learn amazing things about yourself and others.

The best is that you will learn amazing things and then have the opportunity to keep going down that path.

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Julie Wainwright has over 30 years of business experience with deep experience in business to consumer businesses. She is a noted pioneer in e-commerce and has over 10 years experience as a CEO including her role as CEO of Berkeley Systems, Reel.com, Pets.com and now, The RealReal.com. Additionally, she has served on the boards of Wizards of the Coast ($150M gaming company), Baker and Taylor ($800M distribution company) and many nonprofits including the San Francisco Art Institute, Magic Theatre and The Headlands Center for the Arts. She is also an adviser to several start-ups and Springboard Enterprises. She graduated with honors with a BSGM from Purdue University.