Now that I’m running my own company and no longer speak on behalf of Microsoft or anyone else, I feel like I can speak a little bit more freely about some of the things I’ve observed about people at startup companies over the past couple of years.

I worked with close to a hundred companies in some capacity as a Startup Developer Evangelist – some much more closely than others, but nonetheless had a chance to live vicariously a lot of different companies in different markets run by different types of teams with different types of people on them.

Regardless of all of those differences, there’s one thing that a lot of these founders had in common: the less disciplined and experienced founders manage to waste a lot of their time and energy on things that are counter-productive and others that are actively self-destructive.

Here’s seven really unproductive habits that I want to call out in particular.

1. Attend and spend money on countless “startup” events without goals or regard for opportunity cost

My father, an experienced serial entrepreneur, offered up a single rule for me to heed above all others when I started working at Microsoft: “guard your time, jealously.”

Your time is at a premium, particularly during a pre-funding / pre-launch stage – you can’t afford to waste it on things that don’t provide value in some way. The first thing I’ve skipped since going full-time on MarkedUp? Every event that is non-essential; my evenings and weekends are reserved for production deployments or blowing off steam.

There’s consensus among many people in the startup community that “meetings are pointless” – and that’s often true of internal meetings. So what are events?

They’re external meetings – there’s nothing special about a tech event that makes it magically productive. You have to weigh the costs of going against what you could be doing instead, which most startup founders do not.

Be honest with yourself about the value you want to get out of an event – if you’re going there to work a room and generate leads, then it’s probably worth it. If you’re going to go because you just want to “network” and don’t have any real sense of purpose about it, then don’t bother. Go talk to customers instead.

2. Waste enormous amounts of time on “omnidirectional” networking with no real purpose and promise of value in return

Corollary to time wasting behavior #1 – networking with no real purpose.

Networking when done right takes a lot of time – it’s not as simple as collecting up a truckload of business cards at a conference, carpet bombing those poor saps with LinkedIn requests, and watching your stock rise.

What networking should be about is:

  • Seeking out potential business partners, mentors, advisers, co-workers, investors, etc…
  • Qualifying the ones who are interesting;
  • Establish your credibility (so they can qualify you;) and
  • Finding mutual benefit in working together.
    The process of building credibility and qualifying takes time – so, why spin up a bunch of threads with people who aren’t the right fit to help you accomplish your goals? Just so you can say “oh, I know X” at one of those stupid events you should be avoiding?
    Pick your battles – if you’re going to go through the trouble of networking, do it like you mean it and mean it when you do it. Don’t be that clueless person in the middle of an event handing out business cards to people who don’t need you and you don’t need.
    Figure out who you need and pursue those people.

3. Buy crazy expensive booths at startup conferences

Take it from a guy who’s had to work booth duty for a company who can afford the big ultra-delux booth at TechCrunch Disrupt: the booths are worthless.

Unless you’re demoing something tangible that will get people’s attention (MakerBot being a really good example,) you’re better off spending that money on literally anything else.

MarkedUp won a free booth spot at LAUNCH conference due to our performance at Startup Weekend Los Angeles, and we happily signed up. The booth traffic we got was modest – the real value we got out of the event was talking around and working the room.

Every startup should probably try this once – it’s like touching a hot stove or oven: everybody needs to do it one time to know not to do it again.

4. Chase top-down media coverage and press way too early

How many entrepreneurs do you know who’ve stated “getting covered on TechCrunch” as a PR goal?

This is going to sound kitschy but it’s true: the secreting to getting covered by a giant tech blog like TechCrunch is not to try.

Don’t waste time trying to pitch under-developed stories to writers swamped with a glut of press releases from professional PR firms – build something unique and interesting, build interest organically, and the story will start to sell itself.

You’ll still have to put some effort into managing your messaging and top-down marketing at some point, but it’s absolutely the wrong place to start. Your pitch won’t seem like a quixotic / desperate marketing goose-chase to the bloggers if you’ve executed well and have some momentum.

Getting top-down PR for your startup is just like raising money – the conversation starts with a vision and the close comes with traction.

5. Fretting over equity when your company isn’t worth anything

It’s a good thing when an entrepreneur takes the ownership of their company seriously – avoid anyone who doesn’t. However, taking it too far and being miserly with equity during a stage when you’re cash poor and equity rich is both naive and counterproductive.

If you can find a great CTO / biz dev person / designer / product person who believes in your idea enough to be willing to work without pay for months in the name of getting equity, you should be mind-blowingly thrilled.

Congratulations: you’ve just met a really talented person with super high risk tolerance and a tremendous amount of passion for your company’s vision; that’s like wandering the Sahara for days only to stumble upon an oasis with a 5-star resort in the middle of it.

So why screw up a beautiful thing by trying to lowball the person over a few percentage points of ownership interest in your company?

Ditto for early investors and advisors – if you find some competent angels and advisors who are really passionate about your work and are able to put a little bit of money in, err on the side of equitability.

There will come a point where the equity is worth more than the cash, and it will become obvious when that is the case and you’ll be right to preserve the ownership interests of the other stakeholders as much as possible.

6. Dismissing friends and family who commit the crime of “caring about you”

When I reached out to friends who worked at startups over the past couple of years, I was occasionally dismissed with a sentence along the following lines “I’m sorry, I’m just not available – you just don’t know how hard it is to work at a startup.” I’m certainly not the first person to be told that.

I try to have a sympathetic ear as often as I can, but every time I hear this it thoroughly pisses me off because (1) everyone has to deal with grinds and long nights and (2) stress is no excuse to be dismissive to family or friends (people who care about you.)

I’m no stranger to 12-14 hour days – I worked plenty of them at Microsoft and my first startup before that. And being human, I sometimes did a poor job of getting back to people in my life who wanted to hear my voice. That’s one of my biggest regrets over the past couple of years. But even under a great amount of stress, I don’t surrender to exhaustion and say something stupid and hurtful to one of my friends or family members who wanted to check in on me.

You need the help of a lot of other people to pull off a startup successfully. I screwed this up in a major way with my first startup. However, caving into pressure and pushing your friends and family away takes you from neglecting your relationships to actively doing harm to them.

If you’re going to take on something as arduous and demanding as a startup then have the maturity, class, and discipline to bear it like an adult, rather than a child out of his or her depth.

7. Sacrificing nearly all social, physical, and personal needs in the name of “getting it done”

You can push yourself to a large volume of work over a short period of time – you can cram 80 hours into a work week if you can try. But you can’t do it forever.

You know what a successful entrepreneur needs?

They need to work out and get sleep so they can maintain their stamina and energy level. They need to go out with friends and blow off steam. They need to go out on dates. They need “me” time to collect themselves.

Creating a balanced life takes discipline – I dropped the ball on this epically at Microsoft. I starting changing my behavior before I left Microsoft and it’s made me more effective and productive.

When you feel the pressure around any product launch or fund-raising activity and start sacrificing everything else in the name of “getting the job done” all you’re really doing is panicking with a long fuse. Burying yourself in work indefinitely isn’t a virtue – it’s surrendering away the life you’re trying to improve in the first place.

And ultimately it’s a self-fulfilling prophecy: if you keep burning the candle from both ends too long, you’ll eventually fail.

8. Writing cathartic blog posts when you should be reaching out to customers and closing Github issues

Shit. I need to get back to work.

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