In 1998, I took a position with a budding start-up named JuniorNet. It was the height of the dotcom boom and a new generation of entrepreneurs were attempting to change the business landscape forever. While at JuniorNet, we raised — and subsequently blew — more than $80 million. It was the quintessential dotcom story, which came to an abrupt end as the bubble burst. And yet, no matter how ridiculous those times were, they yielded some valuable lessons for today’s entrepreneurs.

Like many start-ups during those days, JuniorNet put a ton of effort into making the office fun. Plus, it was an online service for children, so all of the decor was meant to bring out the child in everyone. There were Nerf guns, medicine balls, slinkys, action figures, RC cars, and play sets in every room. The walls were brightly painted and the desks had fun little designs on them. There were video game consoles, projection screens, comfortable couches, fully stocked Coke and Snapple vending machines (free, of course), and enough bagels to feed an army.
And, for when we wanted to act like adults, there was a fully stocked bar, appropriately called the “nav bar.” We had everything — and did everything –that would make old-timers in large, traditional corporations roll their eyes.

The result of pepping up the office, and focusing so heavily on the culture and morale of the company was that people showed up to work happy every day. We worked late into the night (often sleeping in the office), showed up on weekends, and rarely used our allotted vacation time. Whatever time was “wasted” playing video games or goofing off paled in comparison to the extra hours the company got from its employees.

Was it excessive? Yes, of course. But that wasn’t why the company failed. We didn’t blow $80 million on making the office fun; we blew it on a terrible marketing plan, a worthless acquisition, an insane amount of legal costs, and the same idiotic things that other dotcoms were doing back then. We paid LaVar Burton a ton of money to be our spokesperson. Yes, the guy from Star Trek: The Next Generation and Reading Rainbow. In addition to the spokesperson salary, we paid for him and his family to fly first class to various events, yet I think he said a total of three sentences about the company at said events.

If only we had thought to get William Shatner instead.

In the years since JuniorNet went under, I’ve had the good fortune to work for a handful of start-ups; some successful, some not. I’ve worked with some brilliant people on causes that I believed in, but I’ve never been a part of the same culture that JuniorNet had. Unsurprisingly, I’ve never seen the same work ethic and camaraderie either. One start-up in particular took the exact opposite approach of JuniorNet. The office was cold and industrial-feeling. Consuming alcohol was forbidden. Kibitzing with a co-worker about non-work-related topics was frowned upon. There were virtually no company outings, except for a few times when we left the office only to talk about work the entire time we were out. Company parties were as fun as funerals.

As a result of this culture, there was constant bickering between employees, everyone was starved for vacation time, and the entire place would empty out at 5PM on the dot.

The lesson here is simple: By their very nature, startups are a grind. There’s a lot of work, and too few people to do it. You’re likely to suffer a lot of failure before finding the right path. Those failures eat away at morale and confidence, which, if not treated, can lead to the team imploding. Frowning upon your staff for blowing off steam between 9-5 not only tells them that work shouldn’t be fun, but it also insinuates that work should only happen between 9-5. Start-ups need to blur those lines. Instead of guilting people into working long hours, make them jealous for missing out on all of the fun.

Buy a ping-pong table, or invent a silly game. Ask someone to bring in an old video game console, or buy one for cheap on eBay. On Mondays, make the rounds and talk to everyone about their weekend. Hire a masseuse, manicurist, florist, yoga instructor, clown, etc. to come by the office for an afternoon. Give the company a surprise three-day weekend. Encourage the men to grow moustaches. Organize a potluck for Talk Like A Pirate Day. Bring donuts in on a random morning. Give $10 giftcards to iTunes at random times. Have a movie night in the office.

The dotcom infancy may be over, but the change in business culture it brought is here to stay. Embrace it and you’ll have a team that will counter any bump in the road with the humility, energy, and passion needed to make your startup a success.

One of the best parts of working at a startup is the intense collaboration. When there are only a handful of employees it’s impossible not to be involved in every aspect of the business. It’s not uncommon to see a programmer writing marketing copy, an intern working on a fundraising deck, and the CEO buying the toilet paper.

When you’re in a cramped office space, there are no closed-door meetings. Everyone is a part of every discussion. This is great if you have good chemistry. Fueled by adrenaline (and pizza and beer), you build off one another’s thoughts and come up with creative approaches to bulldoze any obstacle in your way. Decisions come fast and furious with good chemistry. But when you have bad chemistry, problem solving becomes individualized; egos trump common sense, and obstacles multiply exponentially.

There are so many critical decisions to make in the first six months of a startup. Designing your brand, constructing your mission statement, defining your audience, picking a fundraising strategy, developing a marketing plan, choosing a technology platform, etc. And don’t forget about the small, yet plentiful, decisions. Do you send a Christmas card or holiday card? Should job applicants send an email to jobs@ or careers@? Should you bold the opt-out link in your e-newsletters? Do you give away pens or keychains? Should you get a foosball table, or will that scare away investors?

When you have a bad chemistry, these decisions take forever. One person thinks you should send a Christmas card. Another says no, just send a holiday card. Another suggests sending one card to Christians, and another one to everyone else. How about a red and green card that says “Happy holidays!” Or maybe you just do a New Years Eve card to avoid the conflict. After debating for a few days, everyone is worn down and you decided to do nothing. Now, I’ve never heard of startup that blamed their failure on a bad Christmas card, but I have heard of plenty who said they ran out of money before being able to execute on their plan.

The thing with startups is that it’s super easy to become opinionated when you’re dealing with unchartered territory. If someone thinks the logo should be red, not blue, they can point to all of the successful companies with a red logo. Those who like blue can do the same. It’s easy to google your opinion on virtually any topic and come up with supporting “facts”. Yet, for your startup, there are no facts. Nobody can dig up that data from ten years back, when a red logo was been tested and sales declined by 20%. You have no precedents; everything you do is a test. You can try to mimic other successful companies, and avoid mistakes of failures, but ultimately, you have to make hard decisions about your company – even if that means taking a shot in the dark.

When you make a bad decision — and you will make plenty of them — fail fast. Recognize when something isn’t working, figure out why, then change course appropriately. The costly failures occur when egos or ignorance prevent your startup from being responsive to what the market is telling you. And yes, chemistry plays a critical role here as well. Admitting a mistake is easy when you have good chemistry. You’re rewarded for fixing a problem. But when you have bad chemistry, it becomes your mistake. You were the bastard who won that epic logo argument, and now we have to redesign it (or worse, go on pretending that it’s fine). You fucked up and if you continue to fuck up, you will be banished from the island forever.

You know what happens when that type of blame game begins? Everyone becomes scared of making deicions, as it may cost them their job. They stop weighing in on the discussion, waiting for someone else to screw up so that they can call them out on it.

Game over, before it even began.

What’s your management style? I hear that question often. Truth is, it’s constantly evolving and varies from job-to-job and employee-to-employee.

My first management opportunity came when I was 19 years old, working full time while getting my BS at Syracuse University. I ran an R&D lab staffed by a dozen-or-so students. I’m not sure how I got the position, but I was too young to question whether I deserved it or not. The world was my oyster and my ego was massive.

It wasn’t a total train wreck. In fact we got a lot accomplished, won some awards, got some great press for SU, and all went on to lead successful careers. I’m still in touch with nearly everyone I worked with back in that lab, with the exception of one person. Let’s call him Frank. Frank taught me my first real management lesson, and probably the most important one.

One week, during an all-hands meeting, I asked Frank to present the work he had been tasked with completing the prior week. Frank nonchalantly replied that he didn’t do the work. There were some new team members in the meeting, including Frank, and I didn’t want them thinking this was acceptable behavior. I went on a ten minute rant about how there was no room for apathy or laziness on our team; how it was unprofessional and detrimental to our success. I singled Frank out. I wasn’t yelling, or swearing, or pounding my fist on a table, but I was undoubtedly beating Frank up. I had used this tough-guy management style in the past, and it had always seemed to inspire the team, or at least scare them straight. Yet, in this case, as I was wrapping up my rant, Frank’s face turned bright red, he began to cry, and he stormed out of the room.

Frank never returned. He quit the team and never spoke to me again.

The first lesson I learned that day: beware of calling someone out in a group setting. That’s something that should only be done in the rarest of circumstances. I’ve used that tactic less than five times in my now 15-year management career. When and why to use it is probably worth its own blog post.

The second, and most valuable lesson I learned that day was that everyone is unique. Chances are that the same management strategy that works for one person, won’t work for the next. As a manager, your most important job is to learn how to motivate each employee. Some are motivated by a kick in the ass, others require a gentle pat on the back, others are motivated by recognition of their work, or creative freedom, or financial gain, or job security, or collaboration, or one-on-one communication. The list goes on.

If you can figure out what motivates each and every member of your team, you’ll earn their respect and get the most out of them. That alone won’t make you a great manager, but it’s certainly a good start.