Fresh out of Bucknell University in 2010, I envisioned myself starting my career at a big-name corporation somewhere in New York City or Boston. Instead, I went into insurance and then recruiting and marketing—all in independently-owned agencies and start-up companies. My entrepreneurial bosses have taught me so much about the heart and soul of business. I saw first-hand how a few people with a mission can build something monumental. Working at a young company is full of surprises, good and bad. If you’ve been considering making the jump to start-up life, here’s my checklist for you.
Get the family on board.
At Blue Signal, we say, “Entrepreneurs work 80-hour weeks to avoid the 9-to-5 life.” Freedom from bureaucracy comes at the price of work-life balance. Startup hours are long, unpredictable, and inconvenient. Everyone has to be on board to fix unexpected problems. A good work-life balance is consistently at the top of the list of what today’s top job candidates want, but start-ups are far on the other end of the spectrum. Employees sacrifice precious family time in order to keep the company above water.
Start-up life is hard on the whole family. It means taking calls at all hours and never being able to leave your cell phone at home, even for an hour. It means bringing home your laptop on weekends and holidays. It means work emergencies in the early morning and late at night. It means spending more time with your coworkers than your spouse. It means missing out on time with friends. It means trying to explain to your kid why you have to miss their important event because of work. And even after you put in those long hours, you still aren’t guaranteed a pay raise—or even a steady job.
It’s only fair to your loved ones to get them on board before you make the leap. After all, you’re going to need their emotional support in order to sustain the lifestyle.
Learn to be a bureaucracy champion.
Red tape and bureaucracy are the hallmarks of big companies—in fact, it’s the reason many professionals jump ship and go to a start-up. But don’t join a start-up just because you work better in a chaotic environment. Organization and a process-oriented mindset are even more important in a start-up, because a start-up’s goal is to eventually set up red tape and bureaucracy as it grows.
Getting in on the ground floor of a young company is a delicate balance between thriving in chaos and also hating chaos enough to cut through it and create organization and efficiency. If you have poor time management, a disorganized work style, or struggle with deadlines, a start-up is not the place for you.
No more complaining.
Be honest with yourself on this one. If you like to vent by complaining, start-up life is going to be a hard road. In a start-up culture, everyone has the power to bring the company down. That leaves no room for excuses or slacking. It also means no complaining about working harder or better than a colleague. Believe me—it will happen. Sometimes you will end up pulling someone else’s weight. One day, that same colleague may end up covering for you in the same way. Just like in the military, there is very little room for complaining. Make sure your personality can take the daily realities of what start-up life is like.
Working at a start-up means focusing on the moment, with one eye on the future. Unlike a corporation, it does you no good to brag about the amount of face time and the quantity of hours you put in at the office. What matters is cold, hard results. Without results, the bills don’t get paid, and neither do you. Keep your focus on results, and the start-up life will quickly develop you in your weak areas.
Forget the ping pong table.
See point #1 – start-up hours are long. Perks like a ping-pong table in the lobby are usually distractions that most employees have no time to take advantage of anyway. Instead of trying to gauge how much a start-up company is bucking the trend (espresso machines, on-premises yoga, quirky Twitter account, or whatever), look at how the company is positioned to close real gaps in the market. Beware of fake perks, like “unlimited vacation time,” which usually means employees are too busy to take much time off. And if you do see employees crowded around the ping-pong table, beware—that company’s work ethic probably isn’t great.
The best reason to join a start-up is for the opportunity to develop soft skills and make a difference in a company’s goals. Joining a start-up for the perks is like getting married just for the wedding cake. Focus on what you can give to the company, not what the company is going to do for you.
Look for the boring stuff.
While you’re busy ignoring the ping pong table, pay attention to the boring stuff, like their balance sheet. Forget YoY growth. Really. “Fast-growing” is a totally meaningless statistic. Pay more attention to whether the company is managing its costs well. Ask yourself whether the leadership is organized in such a way that they can scale and still produce successfully. For instance, some owners are technical experts in the product and have to be involved in every sale, which means they don’t have time to run the company if it gets much bigger. Some start-ups set wild goals that have no grounding in reality. Others run purely on instinct and don’t track any of their key numbers.
To get an idea of their perspective on their financials, here are some questions to get the conversation going. They should know their numbers well enough to brag about them. Pay attention to what they say and omit. Beware of any company that makes a big show of secrecy about their finances.
- Are their financials in order?
- Do they have clear, realistic goals? What goals did they achieve last year?
- How are they funded? Does this source of funding make sense?
- What metrics do they track?
- Do the company leaders have P&L experience?
- What happens when the money runs out?
- What were their earnings last year? What do they expect this year?
- What is their cost of customer acquisition?
Check your ego—somewhat.
Start-ups demand two contradictory things: big ego and no ego. On the one hand, you need enormous confidence, vision, imagination, commitment, and internal motivation. On the other hand, you have to work long, stressful hours in close quarters with other strong personalities and deal with regular setbacks. Conflict is inevitable. Grudges and backbiting will doom a start-up much faster than bad market conditions. In a start-up, your business is everyone’s business, and bad blood spreads quickly through small companies. Start-ups already have a huge set of market challenges to figure out. You might as well not entertain drama within the team as well.
On that same note, set your personal expectations way lower than your vision. For every Mark Zuckerberg, there are thousands of hopeful entrepreneurs still slaving away at their project in their garage. Keep your focus on the company mission, not on making billions of dollars and buying a private island in the Caribbean.
Get used to being a science experiment.
In a start-up, everyone is learning the best way to do things. Each colleague will bring a different background and set of experiences, and they won’t always jive. Not only that, many start-up owners are first-time managers, and they have to grapple with many huge tasks, from setting goals, to keeping team morale high, to making all major decisions, to paying the bills, to disrupting major markets. Insisting on the old way of doing things is not a helpful tactic for anyone involved.
Start-ups do a lot of experimenting with customers, pitches, processes, management styles, and more. This includes the employees. Be flexible. Sometimes even a bad idea can inspire a game-changer.
Work your heart out, but prepare to fail anyway.
Everyone at my last company loved their job, but the company grew too fast and ended up letting people go during a very difficult time. Life isn’t fair, and start-ups reflect that. Sometimes, even when everyone works hard and gives their all, things don’t work out. A major client cancels, a key deal falls through, supplier costs spike, or unfriendly legislation passes in an important market region. While it is possible to be the victim of a lay-off whether you work for a big corporation or a small start-up, start-ups have a high failure rate, and you can’t always predict it ahead of time.
On the bright side, a high failure rate is a sign of a healthy market, and a healthy market is full of opportunity. Many of the biggest and best companies are started by people who have experienced major failures. People who have weathered failure often have a better work ethic and a richer perspective on life than people who have never taken risks. The founders of Tesla, Facebook, and AirBnB each built hugely successful multibillion-dollar companies out of start-ups, and they all went through failure before hitting the big-time. Keep your timeline short and realistic, and have a plan B.
Practice reinventing yourself.
Working for a start-up is an opportunity to reinvent who you are as a professional. This is a chance that many fast-tracked corporate professionals never have. In a small company, each employee has much more of a stake. This responsibility takes courage and flexibility. Each person has the chance to work on a wide range of responsibilities and develop new skills that they would never have access to as part of a large team. If an experiment fails, there is often a chance to tweak the plan and try again down the road.
Be willing to open up your focus, instead of laser-focusing on one niche area. If your goal is to develop highly specialized industry skills, make sure that it relates directly to the start-up’s niche, because you likely will need to juggle many varied responsibilities as an employee.
Start-up life is challenging, but it will teach you things you can’t learn anywhere else. It is a place where your voice is heard and your work is critical. When you succeed, you know that it was directly tied to your hard work. There are many reasons not to join a start-up. The risk of failure is high, the hours are long, and the work is hard. But the fact that millions of people take the chance is proof that the risk is worth it.
Time for a career change? Read our guide here.