ifindkarma. elegance is refusal.

June 20, 2011

11 Reasons Why Starting a Company is Hard …

In books we find we are not alone.
       ~ Carl Sagan

In stories we find we are not alone.
     ~ Jonathan Nelson


I’m giving a pariSoma talk to the Hackers and Founders Co-op Startup Class of 2011 tonight. And like Paul Graham, I found it helpful to write down what I’m going to say.

Like Evan Williams’ startup advice, I want to say something positive and useful.

My main message is that it’s important to have a network, because you can trade notes with other people who are doing similar things. This is why we started 106 Miles — so that any founder, engineer, or friend who joins us at our meetups will have a network to exchange knowledge and connections, and listen and learn.

That said, if I could tell entrepreneurs one more thing, I would say:

Being a first-time entrepreneur is hard.

Come to think of it, actually…

It’s hard starting a company even if you’ve done it before.

I’ve done it three times, and it’s still hard.

Off the top of my head here are 11 reasons why.

1. Having a great idea at the right time is hard. Big ideas are hard, and timing of ideas is hard. Being excellent is really hard but truly important, since nobody can steal an idea.

2. Designing an excellent and simple product is hard. User experience is hard to make excellent, and user interfaces are hard to make simple. Product-market fit is extremely hard.

3. Developing something people want is hard. Prototyping is hard, and iterating is hard. Minimum viable product definition is hard, and figuring out what people want is hard.

4. Getting traction is hard. Users are hard to satisfy. Attracting and retaining great users is hard, and attracting great content and quelling bad content is hard. Network effects are hard.

5. Keeping the damn thing up and running is hard. Technical operations are hard. “The Cloud” means some computer somewhere out there that you don’t control is going to go down at the worst possible moment.

6. Implementing a scalable business model is hard. Revenues are hard. Not all advice comes in three words. Although there is a lot of three-word startup advice, that matters not. Revenues require continual improvement of sales knowledge and the market, and that takes time, patience, and unbelievable tenaciousness.

7. Building a great team is hard. Finding a great co-founder is hard, and hiring is hard. Even if you read a lot about hiring, it’s hard. And sweet sassy molassy, managing people is hard. And being tough is very hard.

8. Raising seed money is hard. Angels are hard to understand. And finding a great fit between investor and entrepreneur is hard, very hard.

9. Raising venture capital is hard. Venture capitalists are hard to understand. Once upon a time you could
raise money with just a great idea. Then you needed a great idea and a great team. Then you needed a great idea, great team, and great prototype. Then you needed all those things and great traction. Now you also need a great business model, great revenues, great press, and if it’s not too much trouble, make the world a better place, too.

10. Turning away all the free advice is hard. People are unpredictable, and making decisions is hard. But it’s better to make any decision than no decision. Furthermore, the right people make all the difference in the world.

11. Managing your emotions is really fucking hard…      
Ben Horowitz said it best. Also, not quitting is quite hard.

If it were easy to start a company, everyone would do it.

But it’s not easy. And not everyone does it.

It’s hard. Really, really hard.

There’s a great analogy here: starting a company is like you’re 106 miles from Chicago, you have a full tank of gas, half a pack of cigarettes, it’s dark, and you’re wearing sunglasses. Hit it!

Here are 11 things you can learn to navigate those rough waters, ripped lovingly from a long Quora answer I once wrote about mistakes entrepreneurs make. 

  1. Learn the difference between important and urgent.
  2. Learn the difference between working smart and working long.
  3. Learn the difference between an opportunity and a problem.
  4. Learn the difference between lucky and smart.
  5. Learn the difference between focus and activity.
  6. Learn the difference between publicity and reality.
  7. Learn the difference between prepared and over-prepared.
  8. Learn the difference between output and throughput.
  9. Learn the difference between managing up and managing down.
  10. Learn the difference between managing expectations and just riding the roller coaster unmanaged.
  11. Learn the difference between knowing the path and walking the path.

Remember, you can do it. But it’s hard:

Keep your eye on the ball,
Your head above the clouds,
Your ear to the ground,
Your shoulder to the wheel,
Your nose to the grindstone,
Your finger on the pulse,
Your feet on the ground, and
Your head on your shoulders.

Now… try to get something done. 


In summary: Activate your network, work smart, work hard, open yourself to opportunities, close off some opportunities, overcommunicate, underspend, hang in there, stop things that aren’t working, collaborate, and listen.



  1. Ear to the ground WHILE feet on the ground is like an advanced Twister move.

    Comment by Anonymous — June 20, 2011 @ 11:48 pm

  2. Wow, Adam. That rocks… hard. πŸ˜‰ Lucky students at Hackers/Founders. You have an uncanny ability to inspire with words. It’s very neat.

    Comment by Juliana Clegg — June 21, 2011 @ 12:06 am

  3. Thank you Juliana!It may be a struggle, but that’s why it’s up to us to make it a worthwhile struggle.

    Comment by Anonymous — June 21, 2011 @ 2:44 pm

  4. I had heard different translations of the Latin proverb "Fortes fortuna adiuvat" so I looked it up and sure enough there are several: http://en.wikipedia.org/wiki/Fortune_favours_the_bold"Fortune favors the bold, Fortune favors the brave, Fortune helps the brave, and Fortune favors the strong are common translations of the Latin proverb "Fortes fortuna adiuvat" (or "Fortuna audaces iuvat")."I do prefer "fortune favors the bold" best so that’s my translation going forward…

    Comment by Anonymous — June 22, 2011 @ 2:26 pm

  5. "focus and activity" with just the right amount of "important and urgent" goes a long way … i’d also submit that knowing the difference between patience and procrastination is key when building a startup … πŸ™‚

    Comment by Anonymous — June 22, 2011 @ 3:19 pm

  6. Great post, Adam. I???d add a #12:#12 And telling your spouse ???it???s starting to get hard" and that???s why I gotta to keep doing it??? is hard???oh, and you can get your mind out of the gutter… πŸ™‚

    Comment by David Zilberman — July 14, 2011 @ 2:53 am

  7. Just saw this today, and it’s awesome."It’s hard starting a company even if you’ve done it before."I’m on my second turn at the wheel as founder, and it’s just as hard the (second|third|fourth) time as it is the first time around. You touch on some of the key reasons for this in your piece — the world changes, the rules change, and you have to figure out which of your experience still applies vs. what you need to set aside and learn anew.I couldn’t help but chuckle (and twitch a little from founder PTSD) as I read #9. The bar keeps going up, doesn’t it? I’ve gotten great intros to well-known angels who then declined a meeting because what I was working on didn’t have a significant force-for-good component.

    Comment by TrevorFiatal — August 3, 2011 @ 10:32 pm

  8. This is a timeless post. Just read, thanks. Spot on.

    Comment by rekatz — August 4, 2011 @ 4:28 am

  9. ha, David nailed it.. as if 11 steps weren’t hard enough factoring in the ole lady makes it real HARD. Great post Adam, always appreciate the messages

    Comment by Barspace — August 4, 2011 @ 6:43 am

  10. I do like David’s #12, too. Friends, family, spouses (spice?)…. They don’t understand unless they’ve done it before.Trevor, I’m glad it made you chuckle. :)rekatz, I appreciate that you called it timeless!And, more conversation about this topic here:http://106miles.net/convo/137/11-reasons-why-starting-a-company-is-hard

    Comment by Anonymous — August 7, 2011 @ 8:56 pm

  11. See also Tara Hunt’s "So You Wanna Do a Startup, eh?"http://www.slideshare.net/missrogue/so-you-want-to-do-a-startup-ehAnd "Lies, Damned Lies, and Startups":http://www.slideshare.net/startupfest/lies-damned-lies-and-startups-8655909

    Comment by Anonymous — August 7, 2011 @ 8:59 pm

  12. See also Kevin Dewalt’s "Lean Startups are Hard":http://kevindewalt.com/blog/2011/08/05/why-lean-startups-are-hard/

    Comment by Anonymous — August 7, 2011 @ 9:01 pm

  13. "Building a company is just as hard as it’s ever been." ~ Sarah Lacyhttp://106miles.net/convo/120/building-a-company-is-just-as-hard-as-its-ever-been-sarahcuda

    Comment by Anonymous — August 23, 2011 @ 3:56 pm

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