What's the best thing you're absolutely guaranteed to get out of being an entrepreneur?
Freedom, probably. Pride that you had the guts to take a chance. Sometimes, money.
But the best thing you're guaranteed to get? It's the stories. Start a business, and you may succeed or fail, but you will walk away with the funniest, most bizarre stories you'll be telling for the rest of your life.
I've experienced this myself--and I've interviewed literally thousands of others who have as well. That's also part of what makes writing for a place like Inc.com so much fun.
With that in mind, I asked hundreds of entrepreneurs for some of their observations about the weird and funny things we all experience in startup world. If you become an entrepreneur, here are some of the stories you can be sure you'll wind up with.
(By the way--I'll bet you have some great stories of your own. Tell us about them in the comments.)
1. The times you did a crucial phone call in a really weird place.
Entrepreneurs hustle, doing business wherever they can. Sometimes that means taking calls and doing deals in the weirdest places. My best personal story? It's from when I started my first company--a magazine and Web 1.0 destination for graduate students--and I closed a major advertising deal during a 15-minute break in the middle of the Massachusetts bar exam.
Everybody has these stories. Larry Gadea, CEO of Envoy, says he often has to "take calls with investors and hold meetings in the server room," even though it's filled with loud fans as background noise.
Sounds like a story he'll be telling for years.
2. The times you became your company's IT staff, especially if you're completely non-technical.
It always happens in any early startup--there's probably one person who gets stuck having to fix everyone else's computers, figure out the phones, etc.
"Every company I've worked for always has someone who isn't IT but has people constantly coming up to him to solve their technical issue. They're so nice and willing to help, they usually spend most of the time fixing co-workers' problems instead of handling their own work," says Tal Siach, founder of Walyou.com.
Come to think of it, I've worked at startups where the opposite thing happened--we had real CTO-level people, making really CTO-level salaries, who got roped into figuring out why the printers wouldn't work and ensuring that new employees got their company email addresses. Maybe not the best use of high-priced talent, but it's what you do.
3. The times you got busted trying to hide how tiny your startup really is.
There are a lot of ways this happens. One of the most common is when you're saving money on office space, so you work out of gloriously unglamorous digs that you'd never invite a client to. Or maybe you're sitting on your couch in your underwear, while trying to project the image that you've got a Manhattan penthouse with a breathtaking view of the city.
"I have to keep both of my dogs on my lap during business calls and interviews so I can stop them from jumping and barking when packages are delivered or someone is walking down the street two blocks away!" says Zaida Khaze, founder of Wiggletot. "Who knew Chihuahuas have the best hearing of all dog breeds?"
4. The times you had to share quarters with some really strange other startups.
Speaking of office space, I once had a media startup that scrimped and wound up renting the back part of a real estate valuations company, just so my co-founder and I would have a place to work together. They were old school; we were the guys shooting Nerf hoops during our brainstorming meetings.
Craig Bloem, founder and CEO of FreeLogoServices.com, talks about sitting in the office one evening around 6 p.m. only to realize they were sharing space with some kind of band--"a ukulele, piano, and singing."
Fortunately, he says, they were pretty good.
5. The times you...well, let's just call it your "bathroom story."
I'm not sure I have a "bathroom story," but I heard from several entrepreneurs who said they sure did: "The men's toilet/restroom resembles a war zone...well, you know the rest," says Mark Pollard, founder of Mighty Jungle.
I have to say, though, for pure vividness of description, Kristopher Jones, founder and CEO of LSEO.com, wins the prize:
"The worst part of working in a crammed startup space is when you've got to go No. 2. At the LSEO office it's called the 'walk of death,' and every noise from the single-person bathroom vibrates through the office. The smell lingers for hours," says Jones--who somehow still has a company.
6. The times you realized you're a master at balancing free trials.
"In order to avoid paying for certain services (email marketing, online surveys, conference lines, etc.), startups will often take advantage of free trials. Once the free trial expires, they create a new account under a different email address," explains
Sophie Knowles, founder and CEO of PDF Pro.
7. The times everyone hated your company.
Being an entrepreneur means developing a thick skin. You'll get rejected many more times than you succeed.
"We knew we had developed a terrific new wellness device. So when those who tested it complained, we were pretty surprised," recalls Anlynn Liu, co-founder of Lifestone, a Boston startup that has created a portable, health-tracking wellness device designed to measure your vital signs.
"Some people did not know how to use the device," he says. "Others were using it incorrectly. Some people didn't like our packaging. It was a surprise, but also a learning experience."
In the end, "We took all those complaints and criticisms seriously, made the fixes necessary, and the monitor evolved into a better product," he adds.
8. The times you realize you've developed an ironic self-awareness.
"Nobody wants to pay full price for a service, but we expect others to pay full price for ours," remarks Russab Ali, founder of SMC Digital Marketing.
9. The times you scrounged and made do, especially for things like office furniture.
"We all use our own laptops. For better ergonomics, some people use empty boxes to make them eye level, but the cleaning lady keeps throwing the boxes away on us," says Jen Seitz, content manager for Boatsetter.
10. The times you couldn't figure out the most mundane technology.
"Everyone's an engineer, yet no one can figure out how to connect to the darn Apple TV," says Adelyn Zhou, co-founder of TopBots.
Similar story at Reverb, says Tyler Hanson, a data scientist: "Working on a floor full of brilliant developers, yet no one knows how to work the espresso machine."
11. The times you realize you're kinda working for free food and booze.
Fun fact: The first time I ever tried sushi was about 20 years ago, when an investor ordered it during a presentation I was giving. I had to eat to be social, and I couldn't really ask questions, so I had no idea what anything I was about to put in my mouth would taste like beforehand.
Of course, a lot of companies seem to pay people in snacks. Karen Calonico, events manager at Revel Systems, calls it "the free lunch 15. Free lunches and snacks are great, until you look in the mirror a few months later."
12. The times you got screwed because of your bias for other startups.
Nobody understands an entrepreneur like another entrepreneur. So startups look out for each other--and sometimes you can get burned as a result.
Scott Paladini, founder and CEO of Bear Mattress, talked about how his company had used a startup to handle its payroll. Then, the other startup went under.
"You're like, 'Crap, we should have used ADP from the start,'" he says.
OK, I know there are a thousand others. What are your best startup stories--especially the ones you think every other real entrepreneur will wind up experiencing? Let us know in the comments.