Underbelly: What startup
bloggers don’t tell you

November 9, 2009 | Jason Cohen



You have to wonder at these folks who blog so confidently about how to run little companies.

I mean, on the one hand Joel teaches us everything we need to know about customer service while being funny and telling stories. But has Joel ever screwed up? If so, he hasn’t said.

Or 37signals, a company run by geeks with a unique vision about why products (not just software) should be simple and beautiful. They even wrote a whole book about it. Inspiration in every paragraph. Love it! But read their blog and all you get is ultimatums — unwavering confidence that their way is gospel handed down from Mt. Sinai.

Shoot, I’m also guilty of blasting my patient readers to always be honest, never use the phrase “and more,” and how you should fearlessly pursue ideas, or maybe completely change them. Huh?

“Always” “never” “do” “don’t.” Such confidence! It’s a lot to look up to, a lot to emulate.

Aren’t you just like these perfect personas? You’ve got an internally consistent philosophy guiding every decision. Right?

You’ve always got the correct answer and never toss and turn at night.  RIGHT?

You don’t worry about competitors or worry about having shitty ideas or whether money will come through the door next month . . . uh . . . right?

I mean, can you imagine Joel fretting, wringing his hands, wondering how he’s going to make payroll, second-guessing his choices, wondering if maybe they should have added some feature, or frightened that a price-change could completely destroy the revenue stream?

Well, that’s it. I’m coming out of the closet. It’s not fair, and it’s not accurate.

Running a little company is frickin’ frightening. See if any of this sounds familiar:

  1. I don’t have the confidence or the stamina that I see in all those successful people that I admire. I can’t do this.
  2. There’s too much to do; it’s impossible. How does everyone else find the time?
  3. I don’t know anything about marketing/sales/accounting/software/Web sites/Twitter/blogging. These other people seem to know everything. I don’t know enough.
  4. How will anyone ever find out about me? The Internet is too big.
  5. I won’t be able to get revenue. The economy sucks.
  6. Why would anyone give me money when there are big established companies out there?
  7. My orders are supposed to have picked up by now, but they’re haven’t.
  8. Someone just said something bad about me on [insert social networking micro-universe]. Great, that’s easier to find than my own Web site.
  9. My Web site looks like ass. Everyone’s going to know I’m small.

This is just the beginning of the thoughts and emotions I had when starting Smart Bear in 2002. I could list another 100. You’re not alone. This is normal.

“So what?” you cry! “It’s normal. Fantastic. That doesn’t fix anything.”

Okay. Here’s mindset for dealing with all the examples above (in the same order):

  1. Their confidence is a façade. Strong statements are useful literary devices; hedging and vacillation are tedious. But these are not core statements they’ve known about from the beginning of time. Not a one of them has run their companies according to all those rules from day one. They figured it out in the course of running their companies, and then they talked about it. Big difference! You can figure it out too.
  2. There’s always an infinite amount of work. Remind yourself that no matter how hard you work, there’s way too much to do. Take a break and take care of yourself. Do a few concrete things every day. Realize that procrastination is healthy and useful. Success doesn’t come because you did everything, it’s because you did the important things.
  3. Even the “experts” in things like Twitter are still figuring it out. Remember the rise of the Internet in the late 1990s? Go read about what the “experts” said and see if anyone guessed something like Twitter would dominate the world. Don’t attack all these things at once; just pick one thing at a time to get good at. For things like law and accounting, yes, it’s worth the cost.
  4. If your niche is small enough, and if your message is targeted enough, you win. Think small, not big. Win in a teeny corner, then expand.
  5. A recession is the best time to start a company. Use it.
  6. Small companies have advantages and the big-company advantages are not as big as you think, and they shoot themselves in the foot every day. Just phrase things right when talking to customers. And here’s more specific ways to defeat the big guys.
  7. Business has no correct timetable. That’s like saying your kid should be potty-trained by now when every kid is different. You’re measuring against a yardstick that doesn’t exist.
  8. Good words spread faster than bad ones because it’s more fun to tell good stories than bad ones. Thrill some customers, then ask them to post about it.
  9. It turns out your Web site’s ugliness doesn’t matter much. Sure, when you get a little dough you can pretty it up, but Smart Bear’s looked like ass for a long time and it didn’t hurt us. Or, look at Craig’s List. It’s a disaster. Doesn’t matter.

Remember this: Doubt is good. It means you’re being introspective, that you’re not resting on prior knowledge (that might be invalid now), and that you’re honestly weighing the situation instead of employing blind optimism. Doubt is healthy! Hold onto that.

Will any of this make you feel better? Probably not because feelings are emotional, not logical. If I read this list back then, I doubt it would have “fixed” my worries. But maybe it helps to know that this is just how it goes.

So listen to the expert bloggers; they have great advice. Just filter their attitudes through your own lens, and remember that they went through this pain too.

Hey, you! You must have words of wisdom for the downtrodden little entrepreneur. Leave a comment and boost someone’s spirits today!

This post originally was published April 20, 2009, on Jason Cohen’s blog, “a smart bear.” Check there to see comments and more tips from his readers!



Jason Cohen founded Smart Bear Software, maker of Code Collaborator, a tool for peer code review and recent winner of the Jolt Award. He took Smart Bear from start to multiple millions in revenue and 50 percent profit margin without debt or VC, then sold it for cash. He also is a founding member of ITWatchdogs, another bootstrapped startup which became profitable and was sold. He’s also a mentor at Capital Factory (like TechStars or Y-Combinator in Austin). And, he’s the author of Best Kept Secrets of Peer Code Review, the most popular book (35,000 copies) on modern, lightweight methods for doing peer code review effectively without everyone hating life. He blogs at asmartbear Email him: jason (at) asmartbear (dot) com

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{ 5 comments }

Miguel Hernandez November 10, 2009 at 10:12 pm

Love this article! it summarizes what I think of the gospel that a lot of speakers preach after they have succeeded with their businesses. In retrosprective evrerything makes sense always..
However, speaking with pretended confidence makes sense since it is probably more efficient that using a lot of “maybes” or depends”, it simply sells better and is what the majority people want to hear.
The truth is that no one can be absolutely confident about anything except God maybe, and only he can be so if you believe on him/her/it.. so that leaves no room for the rest of us mortals.

Despite that, I can’t wait to see the day that a very successful entrepreneur admits his doubt and insecurities so they look more like humans and less like deities. Everyone has to find their own path and it is important to take anyone’s advice with a grain or two of salt.

Find your way, listen to advice and if you succeed, be humble.

Jason Fried November 10, 2009 at 6:04 pm

“unwavering confidence that their way is gospel handed down from Mt. Sinai” — just so we’re clear here… We’ve never said our way is the only way. We talk about what works for us, and we suggest that it would work for others, but we’re well aware there are plenty of different ways to do things. We just choose not to use words like “it depends” and “sometimes” and “maybe” because 1. they don’t help make the point, 2. they hedge, and 3. reasonable people know that it always depends.

Paul Herwarth von Bittenfeld November 10, 2009 at 5:57 pm

Thanks for your post from a small company CEO! 

Andrea Ong Pietkiewicz November 9, 2009 at 10:12 pm

Thanks for the post: you cheered me up. BTW, Craigslist might look like ass, but it’s successful because it works. Usability will always trump aesthetics, but not the other way round. I’ve preached this unsuccessfully in the past, but what the hey….

Robert Dempsey November 9, 2009 at 10:03 pm

Agreed on all accounts. Many of today’s speakers talk from their current perspective rather than one which tells of the struggles they went through. This could be because they don’t want people to be discouraged, or they want it to look much easier than it is. Who knows. That is one reason though why I love listening to Gary Vaynerchuk, who always tells you that it takes a ton and a half of work to get any company off the ground, and that you have to keep up that pace for a good number of years. And that’s really the secret – to never quit, no matter how hard it gets or how much you want to. Thanks for the great post.

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