The original name for Tech Cocktail LLC was Freedom Jump LLC because that's how my cofounder Frank Gruber envisioned entrepreneurship. Finally, I'm free! I can fly! Down with the corporate grind and gray cubicles! Little did he know.
As entrepreneurs, we've experienced all-nighters, red-eye flights, running out of money, vacation-skipping, bootstrapping, negotiating, firing employees, and stress-induced illness. We may be free, but it's more of a Wild West style of freedom than the content, peaceful freedom of civilized society. Still, I wouldn't trade it for anything.
In talking to thousands of entrepreneurs over the years, we've heard a lot of these behind-the-scenes, gritty, honest stories about what entrepreneurship is really like. Here are some of our favorites.
Tony Hsieh, CEO of Zappos: Culture Is Key
During the Internet boom in 1996, Hsieh cofounded LinkExchange, an early ad network. At first the founders hired friends who wanted to be part of something exciting, but then LinkExchange got funding and started hiring very fast. They hired "any warm body who was willing to work for us and hadn't done more than six months of jail time," Hsieh recalls in the book Delivering Happiness. By 1998, the company had grown to over 100 employees. "One day," recalls Hsieh, "I woke up after hitting the snooze button on my alarm clock six times. I was about to hit it a seventh time when I suddenly realized something. The last time I had snoozed this many times was when I was dreading going to work at Oracle. It was happening again, except this time I was dreading going to work at LinkExchange. This was a really weird realization for me. I was the cofounder of LinkExchange, and yet the company was no longer a place I wanted to be at."
Dina Kaplan, cofounder of Blip: Everything Is Scary
Kaplan struggled with crippling fears early on but didn't realize it. Overwhelmed and overloaded by work, she was afraid to hire employees because she feared she didn't deserve them and would be a bad manager. Kaplan never invited her entrepreneur friends to hang out, because she feared they didn't really like her. When Facebook COO Sheryl Sandberg emailed her asking to meet up, Kaplan didn't reply because she worried about wasting Sandberg's time. This all led to panic attacks, and Kaplan becoming afraid of simply walking down the street -- which she eventually overcame and now speaks about conquering her fears!
Sean Percival, cofounder of WittleBee: Passion Doesn't Last Forever
Sean Percival was the cofounder and CEO of WittleBee, which offered subscription boxes of kid's clothes. He eventually stepped down because they had a cash flow issue and he was starting to lose his drive and passion. In the last quarter of 2012, Percival had tried to push through a Series A round, but investors just weren't interested. They were running low on cash, they cut staff, and things looked bleak. Percival created a parody Twitter account called @SeriesACrunch to vent, with tweets like "Andreessen passed on us but they did invest in a message board for rap lyrics. Now I've got 99 problems and apparently a pitch is one." That was one of his coping strategies, but the burden was just too much. "My personal spirit and energy took a massive hit, from which I frankly never fully recovered," he says. "It was the stressful on-again, off-again nature of our fund-raising that took a huge toll. The ups and downs can become so extreme in some cases that [it] quickly becomes unhealthy."
Tara Hunt, cofounder of Buyosphere: Failure Is Crippling
After three years and $325,000 in funding from angels, friends and family, Tara Hunt knew it was time. She had dreamed of building Buyosphere into the destination to find fashion from real people, but her dream hadn't taken flight. She and her team had to get new jobs. "My dream was dashed. I was broke. I felt like a joke. I disappointed the friends and family who had invested in me. I didn't know what I wanted to do with my life anymore. I hadn't made a fall-back plan," she writes. Hunt had lost her identity. She became somewhat of a recluse, because all her old friends and old haunts reminded her of her pain and failure. "I felt numb. I was in a state of numb for 6 months. I tuned out everything. I didn't want to hear about struggle or success or anything that was going on in the startup world or tech community. I unsubscribed from everything. Every group, every list, every newsletter. I stopped talking to people who mattered in my life during my startup/tech days," she recalls.
Sheila Marcelo, CEO of Care.com: Even CEOs Don't Know What They're Doing
At Care.com, first-time CEO Marcelo once had to deal with an employee who posted a profane comment on a public blog post. In a Thursday meeting, she and some other executives decided that the comment went against their company values, and they fired that person. She apologized for the situation to the whole company on Friday, but she felt troubled the entire weekend. Something wasn't right; she had been too hasty. So she called the fired employee, asked them to come back, and had to stand up in front of everyone on Monday and admit her mistake.
Lori Cheek, founder of Cheek'd: Every Mistake Is Money Down the Drain
Cheek'd is a New York-based dating startup that got on the cover of the New York Times Style section, which garnered lots of visitors and crashed their website. But even worse was a glitch on the backend that went unnoticed until after the fact. Cheek'd is a subscription-based business and unfortunately their developer didn't flip the switch to store credit card information. Cheek shared that, "With hundreds and hundreds of new signups, we lost nearly $30,000 in revenue from this simple mistake. I joke now that our London-based web developer is lucky that he didn't live in America at the time."
Juan Diego Calle, CEO of .CO: Acquisitions Aren't All They're Cracked up to Be
From 2003 to 2005, Google and Yahoo! were embroiled in an acquisition process with TeRespondo, the AdWords of Latin America. At one point, Google and Yahoo! were trying to poach TeRespondo's largest partner, UOL. So TeRespondo CEO Juan Diego Calle did the only thing he could think of. "I remember chasing our partner -- one guy in that company -- around the West Coast from Mountain View all the way to Pasadena while he talked to our competitors, to Google and Yahoo!" recalls Calle. "I was chasing him from location to location -- literally, I was after him from hotel to hotel -- and making sure that at the end of the night after he was done having these conversations with my competitors, that I would end up having a drink with the guy at the bar." Throughout the process, Calle says, Google and Yahoo! both tried to poach TeRespondo's employees, too. He worried that they were just showing interest in order to figure out what he was doing and then copy it. "We were defending ourselves from these two monsters trying to enter our market," he says. But TeRespondo survived, finally getting acquired by Yahoo! in 2005.
While starting up is not all rainbows and unicorns, you can make it fun by embracing the rollercoaster for what it is and enjoying the ride.
Note: Jen Consalvo is the cofounder and COO of Tech Cocktail, a hub for the creative class offering tech-startup-focused news, events, and resources. Tech Cocktail's Frank Gruber has a new book titled "Startup Mixology" (Wiley, July 2014), a step-by-step guidebook to starting up. You'll find even more harsh reality stories in the book, along with tips for staying sane and celebrating positive moments along the way.