The 7 deadly sins of startups

Pride. Greed. Lust. Envy. Gluttony. Wrath. Sloth.

You’ve probably heard of the Seven Deadly Sins, but I bet you’ve never wondered how they apply to starting a company. The answer: surprisingly well!

Over the years, I’ve talked about the seven habits every company should try to avoid and the seven (non-biblical) virtues each company should strive for. Done right, they will help founders focus, save time and avoid some common — and painful — mistakes.

For the purpose of this post, I’ve paired each sin with its closest corresponding virtue.

Sin No. 1: Lust (don’t focus on what other companies have)

As a founder, you have to pay attention to your competitors. Just don’t let that attention turn into lust for what they have — whether it’s a flashy marketing campaign, a fancy office or a killer staff.

Executive lust: Lusting after leadership can be especially tempting. So your competitor hired a rockstar executive who seems to be doing all the right things. It’s easy to think you need your own COO, or CRO, or CCO right now — and they need to be just like the person filling that role at the other successful company that looks nothing like yours.

Think carefully about what you need, why and what role that person will play day in and day out. What strengths and weaknesses do they have? What gaps do you need to fill? And what matters most to your customers and your business? It’s also important to think about your stage and your go-to-market model. When it comes to personnel, one size never fits all.

Virtue No. 1: Patience (know who you are and improve over time)

Think long-term. Have you ever heard the saying, “everyone overestimates what they can do in one year and underestimates what they can do in 10 years”? It’s true. There really is no such thing as an overnight success, and building something great takes time and a lot of patience.

Seek first to understand, then to be understood. The best CEOs I have ever worked for are tremendous listeners. They take everything as a learning opportunity. And they listen to understand and learn, not just to reply. Think about every interaction, especially with customers, as a learning opportunity.

Don’t get ahead of yourself. I recently talked to a founder who had taken a lot of VC funding and thought she had to hire a super-senior field sales team, because that’s what companies do when they have a lot of funding. There was just one problem: She didn’t know if her company was going to have a direct sales model, a self-service model or a hybrid. Could she really sell to enterprises? Was her target SMBs? She hadn’t answered those questions yet. First things first. Think carefully about what you need to do and then figure out how to do it.

Wash, rinse, repeat. Repetition isn’t exciting, but it is important. Are you bored of saying the same thing again and again and again? Are you tired of having to repeat some version of the same thing time and time again to employees, customers, users, investors, social media and the press? Good. Very good. Smart people hate repeating themselves, but people (including me) have the attention span of a gnat. We all need to hear the same message over and over before we have any clue you are even talking. Think about how many times you’ve seen the same commercial and still have no idea what it was for — or how many times you’ve heard someone’s name and still can’t remember it. This doesn’t mean you have to say the exact same thing in the exact same way. As a founder, you can and should keep things interesting and fresh. But you have to be consistent with your core messages and what you stand for. Repetition (made interesting and relevant) is critical.

Sin No. 2: Gluttony (you can’t do everything)

Don’t try to be all things to all people. It’s ugly and impossible. If you’re a company that makes Cheetos, you really shouldn’t try to make lip balm. Recognize when it’s a good idea to leave something to the experts.

Think carefully about your target audience. What are you truly great at? What can you truly be the BEST at? Even the broadest technologies began by targeting a smaller audience. Facebook started with college kids. Apple focused on designers. Salesforce was all about salespeople. VMware was made for developers. All of them moved to a broader audience, but only after their initial success with a narrower one.

Virtue No. 2: Focus (stick to the plan)

Begin with the end in mind. What outcome are you shooting for? You may not get exactly what you want, but without a clear goal, you don’t stand a chance. If you’re starting a conversation with a customer, partner, investor or reporter, know what you’d like to get out of it. You might even want to write down the three things you will get across no matter what you’re asked. Don’t settle for avoiding a disaster. What would make an interaction great — for you and, more importantly, for the people you’re talking to? If you know, you’re halfway toward making it happen.

Don’t make stuff up. No one knows everything about everything. But as a founder, you probably know more about your topic than anyone in the world. Show them. If a customer, VC, investor or reporter asks you a question, make sure your answer includes what’s important. If you don’t like a question or don’t know the answer, don’t ramble. Pause, answer the question itself (quickly, without fluff) and then tell your audience what you want to tell them. Maybe it’s, “We do XYZ, but we find most customers care about ABC. We were surprised initially too, but here is a story/example of a real customer and why it matters.” Or, “We thought that metric was the key as well, but it turns out what’s really important is ABC and here’s why. We were in an internal meeting when we discovered something surprising…” Or, “I really don’t know much about that. I have read as much as you all have. But what I do know is how our customers are reacting today…”

Sin No. 3: Greed (bigger is not always better)

A lot of money and attention can make you very stupid, especially early on. Don’t lose sight of why you started your company — whether it’s to serve someone else, or to make something better. Running a company is hard and it’s easy to let it become your whole world. Stay focused on the problem. No one is as smart (or dumb) as their stock price or valuation.

Think carefully about scale. If one is good, isn’t one hundred better? Not necessarily. More employees are not always better; bigger teams are not always better; more offices are not always better; more features are not always better. Instead of scaling because you can, scale because it makes sense. Understand who a team will serve, what job someone will do, why you need that new office.

Virtue No. 3: Temperance (there’s power in moderation)

Take a breath. You know the feeling when everyone on your team is super-excited and caught up in doing something BOLD or CRAZY? Sometimes it is a great idea, but sometimes it’s just a bad idea caught up in group think. Step back, hold off on sending that email, tweeting that tweet or saying that thing. See if it still seems like a good idea when things are calmer.

Sin No. 4: Sloth (don’t be lazy)

Skip the buzzwords. Words like “scalability,” “optimization” and “disruption” end up sounding like white noise without specifics and substance. Try to scrub buzzwords from your talks and materials and see what you have left. It’s a great way to force substance, details and specifics. You can always add one or two buzzwords back in later, but no more!

Longer isn’t better. Mark Twain said, “I didn’t have time to write you a short letter so I wrote a long one instead.” It’s easy to ramble and trust that others will figure out what’s important. Editing is just as, if not more, important than creating.

Don’t lean on other people. A good conference is an important stamp of approval, but you shouldn’t rely on them to come up with your messaging and be your translator. Work to understand who the audience is and what they care about. If they’re asked about your speech/presentation/Q&A later, what are they going to remember? What story or example will they be able to repeat?

Virtue No. 4: Diligence (put in the work)

Know your shit. A tremendous amount of power and satisfaction comes from knowing what you’re talking about. Put in the time, go deep into something, and you’ll be able to share it with confidence.

Ask for help. That said, you don’t need to know everything. It’s impossible. Asking for help — from experts, your team, your friends — is great. They can be older, younger, more senior, or more junior. Great experts can come from anywhere.

Sin No. 5: Wrath (keep your temper in check)

Don’t get into silly fights. Unless fighting is a calculated part of your strategy — and you plan to continue fighting as part of your brand — don’t do it. This includes fighting with reporters who may get tiny details wrong about your product, or competitors who say something disparaging offhand. It also includes sinking low on Twitter because you are tired or want to show your team you are standing up for them.

Let it go. Elsa was right. Letting something go does not mean rolling over when people attack the most fundamental parts of who you are or what you do. But getting up in arms over silly, small things is a waste of energy. Be thoughtful about what is and isn’t worth it.

Virtue No. 5: Empathy (it’s not about you)

Think win-win. Customers, investors, press and partners don’t work for you, so you have to think about what they’re trying to do. What problem are they trying to solve? Instead of focusing on what YOU want, focus on what THEY care about and how you can help them reach their goals.

Stay connected. Being busy and successful can distance you from your customers and the problems they are trying to solve. Work to stay connected to your teams, to your customers and to your partners. There are a million reasons not to, but it’s crucial to long-term success.

Sin No. 6: Envy (don’t try to be like someone else)

Don’t try to be like other people. Some of the worst presentations or launches I have ever seen involved people trying to be like someone else. A bunch of them were wannabe Steve Jobs moments. It was not pretty. Be the best, most interesting version of yourself, understand what your customer cares about, be in tune to what is relevant and learn from others. But do not try to be like Steve Jobs.

Don’t try to be like other companies. You’ve been working really, really hard, but so have your competitors — and now they’re the ones getting the accolades and traction. It’s not fair. But “fair” is the only four-letter word a startup founder shouldn’t use (go nuts with the other ones, as long as there are no children nearby).

Comparing yourself to others can easily turn to envy — and envying someone else’s anything is a giant waste of time. Having a sense of urgency and focus is useful and necessary, but envy is destructive. It can lead to rash decisions (usually in reaction to what someone else has done) and cutting corners. Chances are you will rise or fall because of what you do, or because of something like the global economy — which is out of your control — not because of another company. No one has to lose for you to win.

And envy is not inspiring. Your job as a leader is to convince other people to follow your vision and passion — not someone else’s.

Virtue No. 6: Fortitude (be strong)

Everyone struggles. From the outside, every successful company looks like they’re headed “up and to the right.” But it’s almost never that way on the inside, where setbacks and mistakes happen all the time. It can be tempting to take the easiest route, especially when you’re under pressure. But sometimes you have to move back to go forward. Rewrite, redo, reorg. Doing it can be time-consuming and difficult, but if the change is important, it can make all the difference.

Leading when things are tough. Leadership matters more when times are hard. Competition, layoffs, bugs, execs leaving, controversies — these are the times when your teams need to hear more from you, not less.

Sin No. 7: Pride (…goeth before a fall)

Success has many fathers, but failure is an orphan. It’s tempting to take credit for the “wins” and blame the “failures” on the market or the competition. The truth is usually somewhere in between. Learn from what you do and what happens to you.

Keep things in perspective. You are never as good or as bad as the press (or VCs or Twitter) says you are. Good press can easily go to your head, and bad press can take it all away in one fell swoop. Focus on what’s important and don’t get distracted by who’s up and who’s down, because tomorrow will be different.

Virtue No. 7: Humility (know what you don’t know)

Try to understand the critics. You can’t argue with trolls, but not everyone who disagrees with you falls into that category. No matter how annoying someone is, ask yourself if they have a point. Can you learn from them?

Seek feedback from others. I’m talking about real feedback, not just the good kind. Feedback can be an amazing gift that pushes you to get out of your own way. Take time to look back at what you did, why you did it and how it worked out.

Admit when you get it wrong. Everyone gets something wrong sometimes. A simple, honest apology can be incredibly powerful, and admitting when you made the wrong call or say the wrong thing can give you a lot of credibility.

Like the actual seven deadly sins, it may be impossible for founders to avoid ALL of these pitfalls — or consistently model the seven virtues. But hopefully, this list will help you and your company stay out of startup purgatory.

Have some sins or virtues of your own? I’d love to hear them.