Why You Should NOT Leave Your work to Become an Entrepreneur

Why You Should NOT Leave Your work to Become an EntrepreneurUnknown

 
I went to a recent Ellevate Network event, at which we hosted a pretty prominent entrepreneur, who runs a VC-funded start-up that’s gaining some real traction. In other words, she’s “living the dream.” Someone in the audience asked her whether it was fun to be an entrepreneur.

She paused.

Her answer? “No. Not really.”

I can relate. In addition to owning the Ellevate Network, I’ve recently announced a Series A raise for a new business, Ellevest. This is a to-be-launched digital investment platform for women. These after a career at big companies. And not a handful of days goes by that someone doesn’t ask me “Aren’t you having so much fun?”

The truth is that being an entrepreneur is harder than running Merrill Lynch. (And I’m not just saying that; I actually ran Merrill Lynch.) It’s the hardest thing I’ve ever done.

Sure, it’s great not to have to attend the Operational Risk Committee meeting and sit through the page-by-page review of the 226-page deck. I can’t tell you how great.

But for those of you thinking of leaving your big-company job to be an entrepreneur, here’s why you shouldn’t:

Raising money can be humbling. Really humbling. None of us likes being told our baby is ugly…..again and again and again. “But, hey, keep in touch.”

B2B sales are humbling….and take longer than you can imagine. No, your phone calls aren’t returned as quickly as when you worked in your big company job. You expect that. The more interesting insight to me has been how often people try to be nice and end up stringing you along. They don’t recognize that a “fast no” is ok; it’s the “slow no” that kills you.

And even a “slow yes” can put you out of business. I worked with one guy at a big bank who loved a start-up so much…and encouraged them so much…that the start-up ran out of money and shut its doors as all of the approvals for doing business with them were working their way through the system.

So sometimes a “fast no” can even trump a “slow yes.”

Hiring people is hard. Hiring people is always hard. But at a start-up, the stakes are so much higher. That’s in part because there are simply fewer people, so one has to be more thoughtful about making sure there aren’t any holes in the start-up team’s skillsets (and that includes filling in the founder’s “flat sides”). That’s why, for me, team diversity is so important.

And is it just me?? Because I’ve found, amongst entrepreneurs, some of the most talented people I’ve ever worked with, by good measure; they love the rush of entrepreneurialism and would never thrive in the constraints of a big company.

And then there have been some others. I’ve come across a couple of screamers. By that I mean, people who scream. At work. A lot. The screamers are filtered out of big companies pretty quickly. So watch for people who’ve bounced around a lot, and particularly watch for people who receive less-than-effusive recommendations. And always, always do back-channel reference checks.

Hiring people is hard, Part 2. If you come from a corporate background, many of your contacts won’t fit your job descriptions and needs: the jobs pay less cash than what big company folks are making, the jobs may be broader than what they are doing , and parts of the jobs can be more junior.

(An example: I’m copyediting and have been building earnings models. Not something I would have thought I would be doing at this stage of my career. I happen to love both of those things and find them relaxing. But that may be a personal quirk.)

I had this issue at Ellevest. As we began to hire, you would have thought I would have known a lot of Chief Investment Officers….and I do. But it took me the better part of a year to find our Chief Investment Officer because I wanted one who had the experience and analytical grounding….but then was able to, and wanted to, approach the puzzle of women and investing in a creative way.

Office space. When I speak to young-entrepreneur-hopefuls, I hear what they think the office environment will be like. Start with a bit of time in a shared workspace; then move into your own offices with exposed brick walls, a foosball table and beer on tap; and then you’re a billionaire.

For some, perhaps. Right now, at my start-up, we’re in a space that’s so small I can’t get out of my chair without slamming into the back of our lead designer. At some point, we may fuse into the same person.

And everybody’s a critic. If your idea is truly innovative, you’re going to hear from the naysayers. After all, if it were such a good idea, someone would have already done it, right??

Oh, and it’s terrifying. Something I never thought about in my big-company job: cash flow. When your business has billions of dollars in revenue, you can make a lot of mistakes and still have a viable business. But in a start-up, make a few hiring mistakes (it takes several months to find the right person, a couple of months to figure out they’re not the right person, a couple of more months when you try to coach them and give them the opportunity to become the right person, then another couple of months after you part ways to find the next right person)….oh, and the work they’re supposed to be doing doesn’t get done in that period of time….well, do that a few times and you’re out of money.

Being an entrepreneur is the only time in my career that I’ve lost sleep (and I was on Wall Street during the financial crisis.)

There is a lot of paperwork…and taxes….and regulations…. I can’t tell you the number of people who tell me they slipped up on some of the paperwork needed for their company. It’s one of the no-fun parts of being an entrepreneur that nobody talks about.

You can’t coast. You know those days at the office when you used to come in and didn’t really do that much? You don’t have those days as entrepreneur. If you don’t do much, then not much happens. And remember what I said about cash flow? Yeah….that.

This last paragraph is the one in which I am supposed to say that, even with all of this, I wouldn’t trade being an entrepreneur for anything. And, for me, that’s right. But the failure rate for entrepreneurs is high, so I had to be very, very honest with myself about my, and my family’s, willingness to take on this professional risk.

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