Me and Cheddar founder/ex-Buzzfeed President on the hard beginnings for an entrepreneur

Are You Ready to Leave Your Job to Start a Business? Get Ready for These 5 Sucky Things to Happen.

Betty Liu
4 min readSep 6, 2016

According to various news reports and studies, the U.S. is on the cusp of an entrepreneurial boom. Where is this coming from? From the very same people who drove some of the longest bull runs in stock market history: the Baby Boomers.

Entrepreneurial cheerleaders say the 76-million strong are turning their mid-life crises into mid-life businesses. While I’m sure this is true, the fact is it’s very tough to leave a corporate job to start your own company. The older you are, the better paid you are likely to be. You’re set in your ways. You have a routine, not to mention probably a pretty sturdy mortgage payment, kids in college or about to go to college and all the other expenses life throws at you. Entrepreneurship is not for the faint of heart or the skinniest of wallets.

While you can partly take care of the financial situation, what some people aren’t entirely prepared for is how diminishing it can be to go from “man/woman in the fancy suit” to “scrappy entrepreneur.” The shock is, I’m told, enormous from the people who’ve done it.

Scott Kurnit is one such person — he left a cushy job in media to start About.com and people thought he was crazy. Watch his tips below on 10 essential things you need to know if you’re going to take the plunge.

I’ve spoken to enough entrepreneurs who’ve gone through this process to know that at least these 5 things are true:

1. You realize you have to do everything-and that means, everything. People in companies have a wide support network. They have assistants, interns, junior employees, who absorb a lot of the impact of tedious tasks. Not so when you start a company. Mario Gabelli, a billionaire investor, recounted in my book, Work Smarts, how he was licking his own stamps and designing his own stationary (he copycatted someone else’s) when he first started his fund.

2. Decision-making speeds up and they all feel like do or die. In a big company, it’s okay to take a while to make decisions. Things have to go through committees. If you take a little longer to make a strategic decision, nobody punishes you for it. Not so in a startup. Stalling on decisions can cost you time and money; sometimes the only way to get an edge on the bigger guys is to move faster and be more nimble. At the same time, making the wrong decision early on can cost you plenty down the road. Again, if you scare easily, this might not be the thing for you.

3. People dismiss you. When you lose the title, you lose the friends. That sucks but it’s the truth. Almost everyone I’ve talked to who’s left a big job says the same thing: All those people you thought would be there for you aren’t and some of the people you never expected to be there for you…are. Jay Margolis, who left many big retail jobs in his long career at brands like Tommy Hilfiger, Liz Claiborne, and most recently, Cache, says you become “invisible.” As he told me in my podcast, Radiate, Jay said when he left Express and before going to Cache, “you don’t get calls and you just wonder.” Is it because people are small-minded? Listen to what Jay believes in our conversation on iTunes and SoundCloud.

4. A 25-year-old might know more than you. At a big company, you’re like the big hot shot with the answers to everything. At a little startup, you might be desperately chasing down that college grad who has the right skills for your business. Suddenly you’re eating humble pie because you don’t know anything about a new area. You’re tweeting and look like a fool doing so. You might be yapping weird social media jargon you know nothing about. Welcome to a whole new, uncomfortable world.

5. Capital is your #1 concern. Forget that you’re worried about how you pay your own bills, what about paying your company bills. Entrepreneurs are never out of fund-raising mode and they almost always feel like they’re about to go under, even if they’ve raised a ridiculous amount of money. At that point, they’re celebrating every little revenue victory that comes in-10 paid subscribers today? Yay! More than one entrepreneur has told me he or she has had to dip into their savings to make payroll. Balancing that weight on top of having to grow your business can seem like a nightmare. You’re constantly moving from crisis to big picture to focusing on trees vs the forest and then vice versa. It can make your head spin.

However, if still after reading this you’re hankering to become an entrepreneur, remember this. Every single one I’ve spoken to-and there have been more than a dozen-have said it’s all worth it to be your own boss and build your own business. One in particular who was nearly broke when his company went public said he wouldn’t change one single thing and he’d do it all over again.

Are you ready to be that crazy?

If you liked this article and want more content to help you become a better manager and leader, join the Radiate community by clicking here. And for a limited time only, join our “Radiate with Us” experience and win a rare opportunity to have an exquisite private dinner with Chef Thomas Keller at Per Se in New York City. Don’t miss this incredible chance — enter here!

--

--

Betty Liu

Executive Vice Chairman, New York Stock Exchange. @BloombergTV alum! I love scaling people connections. www.nyse.com/insights