(P.S. Are you going to SxSW?  If so, drop me a line and we'll coordinate.)

Most people start their first company while they still have a day job.

It makes sense: You don't need loans, and you don't need funding. If you "fail" all you've lost is time, but considering the fun, the stories, and everything you'll have learned, that's hardly a failure.

You just need to give up all your free time which, if you've caught the "founders" bug, is A-OK with you.

But you've also placed yourself in a hazardous, potentially legally ambiguous situation. If managed improperly, you're unnecessarily risking lawsuits and worse.

I've been on both sides of the table: I've done a startup while working and I've employed people who either were or are very capable of having their own startup on the side. And I've known people who were sued because of it, and not all of them won.

Here are my tips for how to pull this off.

IANAL

Ho hum, hedging is so tedious. But I have to say it: I Am Not A Lawyer. None of this is legal advice. If you do or don't do anything listed here and anything bad happens, it's not my fault.

If anything good happens, I'm thrilled and honored to accept your munificent cash donation.

Pick a business that can thrive within your constraints

Your side venture has constraints a "normal" business doesn't have:

1. You can't answer the phone during normal business hours.
2. You can't answer emails during normal business hours.
3. You can't afford to hire three developers to add features and bugs.
4. You have to work in fits and spurts.

Your natural tendency is to fight these constraints, but that's the wrong approach. For example, you know that to avoid social media shitstorms you're supposed to have stupendous customer service, so you claim as much on your website. But then you don't have a phone number and emails sent to you at 10:00am don't get answered until that night (which means they're not viewed until the following day).

That's called a "missed expectation." It's also called pissing in the wind — it's just going to come right back at you.

The right attitude is not only to work inside your constraints, but to turn them into competitive advantages!

For example, your regular income affords you the luxury of underpricing your service. So if anyone complains that there's no phone number, you can just point out that for $5/mo you can't afford a phone staff.

As another example, pick a product in which simplicity and having very few features is an advantage. "We do only one thing and we do it better than anyone" is a great marketing slogan. You don't have the time to make a Microsoft Excel knock-off, so don't!

Embrace slow growth

We all have dreams of stratospheric growth, whether it's hoping the next blog post will get 267 votes on Hacker News and double your RSS subscribers, or hoping that the advent of release v1.1 will set the blogosphere ablaze.

Good work if you can get it, but it's not a "plan," especially not for a business you're running in your spare time. In fact, any bootstrapped company should be aiming for slow, consistent growth rather than explosive growth.

This is not a bad thing! Slow growth maximizes your chance for success. Slow means your success is not dependent on some unlikely, massive event that's totally outside your control. Slow means you can change drastically during the early days without sinking the company. You have a job, so you don't require explosive growth to be successful anyway.

Remember, your immediate goal isn't to make millions of dollars, it's to build a business just solid enough to quit your day job. That might mean enough profits that you can already live (frugally) off the company. Or it might mean you have enough customers to have "proved" you have a viable business model, so now you can raise money with sensible terms.

Don't lie at work

The best way to avoid a lawsuit is to prove that your employer knows you have a side project.

I know, you really really want to ignore me and operate in secret. You're afraid to tell them because they're might do something — fire you, distrust you, or look at you funny at lunch.

Yes, that might happen. But what's worse — one of those things or a lawsuit? If you don't think they'll sue you, then you shouldn't be afraid of telling them! They are going to find out anyway. You need to tell them on your own terms.

I've always told my employer, and it always worked out for the best.
Here are those stories.

How do you tell them? Write a simple document explaining what you're doing. Here's my template:

To Whom it may Concern:

I have a hobby which does not in any way conflict with work. I'm writing this letter to make sure you're aware of it so there's no misunderstanding.

My hobby is ....

I work on my hobby only at home and on my own time; it is not in conflict with my employee agreement. I own it; [Company] has no ownership or rights to it. Like any hobby, it could generate a small amount of income.

Although I don't anticipate it, I understand that if my hobby ever became in conflict with my job that it's my responsibility to notify you immediately.

Thank you.

Then you get this letter signed by someone with authority. "Authority" means someone who can legally represent the company. This will of course depend on the company, but typically C*Os or the company's legal council is a good bet.

Getting a supportive boss to sign it isn't good enough. He can't speak for the company.

Check your employment agreement

There's a phrase in the template letter about your side business not conflicting with your employment agreement. Is that true? It'd better be.

Employment agreements are typically biased in favor of the employer, sometimes with outrageous clauses saying that anything you do, even at home and on your own time and unrelated to anything at work, is automatically owned by the company, and that furthermore you're responsible for identifying and reporting on those things, and if you don't do all of the above there's no limit to the damage you could have caused.

Courts have thrown out some of these egregious contracts, but that's unusual, and you can't depend on that. You don't want to go to court at all. Besides, you signed it.

Read over your agreement and make sure it's legal to have the side business. If it isn't, you must write a letter like the one above specifically stating that this is a valid exception to your employment agreement.

Don't use company property or Internet, for reals

Another clause in most employment agreements is that anything you do physically at work, or on software and equipment owned by the company (e.g. laptop, customer lists, Photoshop) is automatically the property of the company.

This clause is fair. If your project is really on the side, you have no business doing business at work. If your project is really yours alone, it cannot be assisted by a company laptop, company software, or company Internet connection.

When it comes to company property, be paranoid. Assume Big Brother is watching. Assume every laptop has a secret program that records all keystrokes, mouse clicks, screen shots, web sites, and emails you read or write. Assume everything you do on the Internet is recorded, cataloged, tagged, and monitored continuously by a methamphetamine-powered slave-army.

Now I realize you're super clever. You want to sneak in some tech support emails during the day, so you use a cocktail of  Anonymizer plus GMail-over-SSL to confound the network admin. Because of course covering up your activity is a sure sign you're doing something legal...

Even that is not enough. If they decide to sue, they get to look through your email records (it's called "discovery"). Then they have 100 emails you sent during work hours. You lose.

Get the picture? Just don't do it.

Time management is critical

I'm naturally awful at personal time management. I procrastinate, I'm disorganized, and if I'm not careful I'll burn two hours ROTFL at FailBlog with nothing to show for it but tears of laughter puddled under my keyboard.

A startup already generates an infinite amount of work. It takes all your time, which for you is 40 hours/week less than it ought to be. You can't afford to waste time, whether that means bad habits or working on the wrong tasks.

There's no silver bullet — workflow is a personal matter — but here are some techniques to get you started:

• Check email infrequently.
• Inbox Zero — Processing email until nothing remains has both psychological and practical advantages.
• GTD (Getting Things Done) — This technique literally changed my life. Few people implement 100% of this system, but everyone can take away a trick or two that makes them more productive.
• Work in sprints — Short, focussed bursts of activity eliminate the surprisingly large waste that comes from context-switching and interrupt-driven behavior.
• If you don't sleep enough, your productivity plummets. Trading an hour of sleep for an hour of coding is never efficient.
• Use a tool like RescueTime (free!) to empirically discover where you're spending time; the waste becomes clear. P.S. Tony Wright, founder of RescueTime, started that company while employed and wrote about what he learned.
• Optimize slowest tasks first — Identifying and optimizing the slowest tasks increases your overall productivity more than you think.

What are your tips? Leave a comment and join the conversation.

This is a guest post by Mike Schoeffler, founder of iPhone running application Roadbud. He writes a refreshingly approachable fitness blog.

I hesitate to take issue with Jason’s Sacrifice your health for your startup — particularly after his wife gave her up-close-and-personal. His main point is dead on — we need to unhealthily obsess over our creations. But take this too far and your productivity drops off the cliff.

As founder of a run/bike app startup, I can write off my workouts. I have a ready excuse for squeezing in a little “sweat equity” — I need to get in shape to know my customers’ issues. However, I also know firsthand that exercise increases total productivity. I avoid colds and I have more mental staying power. Plus, I have a better attitude when I don’t resemble shtik fleysh mit oygen (Yiddish for a piece of dead meat with eyes).

Technology startups can be horrible for your body. Not mangle-your-arm-in-a-press horrible. But we have all sat in front of a computer for hours on end, tapping on the keyboard and lost in thought. Your only movement is reaching for the can of Mountain Dew or grabbing the bag of chips. Maybe you tear yourself away long enough to call for pizza delivery.

Perfect for veal, not so much for humans. It wasn’t always this way. Joel Spolsky notes that in times long gone, programmers got washboard abs while waiting for the compiler.

Think about exercise in light of a situation we’ve all faced: all-night coding sessions. Remember the all-nighters you pulled, heroically pumping out code until dawn to make a big deadline? Seemed like you were getting lots done while you took a bullet for the team. The truth is your programming was probably awful. Even a few hours’ sleep would have prevented your spaghetti mind from dumping spaghetti code. The worst part: as you got more sleep-deprived, the better the whole idea looked.

Workouts are the same -- as you drop further into sloth, inactivity seems smart. Only the uncommitted have time for exercise, right?

Exercise is pretty useful for anyone in a startup even without the health and stamina benefits. Just as your best ideas appear while you’re soaping up in the shower, elegant solutions spring up when you’re out running. Your mind is searching for something to think about besides your body’s pain. And while you don’t have a pen in the shower, you can always use your cellphone if a brainstorm strikes during a run.

...

Let’s say you’re ready to start an exercise regimen. What next?

Some of us already know how to work out – we’ve just given ourselves license to be lazy in this one area. If you’ve never been in shape, start gradually. Choose an activity you already enjoy (biking is my favorite). Regular exercise is far more important than going Charles Atlas overnight. Couch To 5K is a great place to start.

A little goes a long way. You already knew you don’t have time to train for a marathon. Maybe get in a quick run before work – you’ll feel great all day. Or inch up to a hundred pushups while prepping for a sales call. Zen Habits has a detailed list of exercise hacks to help ease you into the habit.

The critical thing is to just get started. Close your door, wipe the crumbs off your pants, and give me ten pushups now!

What are your fitness tips? Leave a comment and join the conversation.

When I asked recently whether you'd like to see other people guest-posting here, the response was far more positive than I expected.

But as much as you're open to hearing new voices, you were also clear that you come here for quality content (not quantity), for entrepreneurial perspective (not product pitches), and for my taste in topics, especially "behind the scenes" admissions of agony, humiliation, and mortifying unease.

(Gee, is this therapy for me or for you? Probably both... I feel myself transforming into the Dr. Laura of bootstrapped entrepreneurs...)

So over the next few months I'm going to run a few guest posts.

Ground rules

1. I will still post every Monday, as usual.
   The goal is to present additional perspectives later in the week, not to replace my content.
2. I will favor counter-points.
   There's no sense in a guest-post that completely I agree with — I can just write that myself! Thoughtful counter-arguments help all of us think and learn.
3. I will ignore the poster's fame.
   I don't care if the guest has 4 RSS subscribers or 4 New York Times best-selling books. This isn't a popularity contest.
4. When constructive, I'll add editor's notes.
   Several of you said that you want me to add my perspective.

This begs the question: How does one submit a guest post if one is so inclined and one realizes that one's writing is not actually enhanced by using legacy Germanic grammatical constructions such as referring to oneself as "oneself" instead of "me?"

Submitting a guest post

1. Have the post fully written before you contact me. That means associated pictures (with optional caption), text styling (e.g. bold or bullet points), and appropriate length and grammar. If it sounds like I'm shoving all the labor on you to make it trivial for me to post it, that's because I'm shoving all the labor on you to make it trivial for me to post it.
2. In your email, attach a plain-Jane HTML file and separate images. No Word® or PDF™ or iWork® Pages®.
3. Most submissions will not be accepted, without explanation. I don't need the mental anguish of telling kind folks things like "Your writing isn't good enough." Don't take it to actually mean you're not good enough, just assume your post simply not a good fit for this blog.
4. If your submission isn't accepted, try elsewhere! This blog is my voice with occasional interludes, but there are loads of blogs driven completely by guest posts. Try one of those!

The first guest-post will go up tomorrow. Please use comments and email to keep me honest and let me know what you think.

What if your company were allowed only one advantage over the competition?

What would a sales call look like, starting with your 30-second pitch, then dealing with skeptical questions, trying to earn this potential customer's interest, respect, and eventually money, all with only one advantage?

Impossible, or just pointless?  Neither!

You should go through this exercise because this skill is valuable in every sales call. Sometimes you're defending the few advantages you have over a specific competitor. Sometimes you're arguing the virtues of small businesses over large ones. Sometimes you're defending your product against what the potential customer perceives as a glaring lack of functionality.

Hanging your hat on just one advantage that you can own completely is stronger than diluting your message across many advantages.

And it's not just in face-to-face sales calls either. Your homepage becomes laser-focused. Your advertisements become pointed, powerful, pithy, and other words starting with "p."  Your 30-second pitch becomes compelling. You know what to blog and Twitter about. Your 5-minute product demo drives home a single point. Everyone knows who you are and where you stand.

And at least on this one point, you're untouchable. Doesn't that sound nice? It is nice.

But don't you need lots of advantages to overcome sales objections and competition? No. Let's see how to riff off single advantages, using them to answer a range of skeptical questions and concerns.

If nothing else, this should get your juices flowing and make future sales calls and marketing messages more effective.

Help me spread the word about this program!

I'm a mentor and investor in CapitalFactory, a seed-stage startup mentorship program in Austin, TX. Each year we pick 5 companies to participate in a 10-week summer program which includes:

• 20 real mentors
  Twenty entrepreneurs who have actually been in your shoes — creating companies from scratch, growing to millions in revenue, and often selling them. No posers, no one who was "there for the ride." Here's the list; see for yourself. You'll get both one-on-one time and weekly group meetings.
• $20,000 in cash
  You can spend it however you want — quit your day job, buy some ads, license technology, whatever you need. Where does the money come from? From the mentors themselves, personally.
• $20,000 in free stuff
  Free legal services to set up agreements, contracts, and EULAs, free graphic design work to make a nice logo and website, free PR services for product announcements, free office space, free website hosting, free software, and more.
• Present at Demo Day
  At the end of the program is "Demo Day," where you get to pitch in front of 150 investors — both angels and VCs, both individuals and firms. Last year one of the five companies was funded by Demo Day — it can be that quick. Even if you're not looking to raise money, it's a great experience and personal networking event. Last year the keynote speaker was Mike Maples.

For more details, including the application process and a great 3-minute video which includes interviews from the 2009 companies, see the CapitalFactory home page.

We like to say we're the #3 most popular seed-stage group after Y-Combinator and TechStars. Help me spread the word and keep us at #3!

Questions? Leave a comment.

I'm sick of being admonished that success is predicated on spending the next 10,000 hours of our lives becoming "an expert."

I'm sick of hearing about how I should be molding my life in the image of Michael Phelps or Albert Einstein, because the only thing that separates me from genius is identifying my strengths and working really really hard.

I'm calling bullshit.

We're so busy trying to make ourselves into outliers that we're forgetting about what's important.

Penelope Trunk pushed me over the edge when she wrote that for the last two years she's been schlepping around a Harvard Business Review article called "The Making of an Expert" because:

"The article changed how I think about what I am doing here. In my life. I think I'm trying to be an expert.

Penelope goes on to equate being an expert to "success," and laments that she isn't an expert in anything, nor is she making headway.

I don't know whether this is funny or sad, because she wrote this on her blog — a blog with 48,767 subscribers (at the moment). There are literally a million people trying to be "expert" enough at anything to achieve that level of "success," and almost none of them will ever be that "successful."

Oh yeah, and this comes on top of a six-figure book deal and years of writing for teeny inconsequential publications like the Wall Street Journal and Time magazine.

But Penelope considers herself neither a success nor an expert.

Yeah, right. She is a success. In fact, don't you agree her problem isn't a lack of expertise but rather that she shares my irrational yet commonplace feelings of inadequacy?

If by her definition she's not even close to being an "expert," clearly being an expert isn't required for being successful.

She goes on to explain how much effort it takes before you're allowed "expert" status (my emphasis):

"You need to spend at least ten years working in a very focused, everyday way on the thing you want to be great at. Evidence: high school swimmers today would beat Olympic records from years ago."

That's not "evidence." There are more high school swimmers than ever, therefore more opportunities to find and train great swimmers. They have access to diet, training, technology, and facilities that didn't exist years ago. That's all.

And anyway, supposing it does take that much sheer effort, clearly it also takes talent (though she denies this, as do other, cough cough, experts). I'm a case in point: I practiced the piano for an hour a day for more than ten years. I became good, but there were others who practiced twice as much who were worse, and still others who practiced less and are much better.

We all know this. Why are we allowing people to tell us otherwise?

Not one of the successful entrepreneurs I know started as an expert. Rather, career and expertise are developed simultaneously, eventually resulting in success when coupled with a few key events (due as much to luck as effort).

Pick anyone. Sergey and Larry weren't advertising experts before they started Google. Joel Spolsky wasn't a blogging expert before starting FogCreek. I didn't know anything about peer code review before starting Smart Bear.

In fact, in all these cases it would have been impossible to have been an expert! Why?  Because Google reinvented advertising, there were no "blogs" when Joel started posting essays, and there was no tool for code review until I invented one.

Innovation defies prior expertise.

So let's stop being distracted with these arbitrary definitions, artificial goals, and unnecessary prerequisites to "success."

Let's just get back to work.

What do you think? Am I missing the point or taking it too far?  Leave a comment and join the conversation.

The startup community over at Answers OnStartups has really taken off! Dharmesh and I started it just a few months ago and it's already helped thousands of people. And vice-versa: For every question I've answered, there's another where I've learned something too.

It's a total blast — you should come check it out.  It's like being in a room with 200 people in various stages of doing startups, all eager to listen to your problems and questions and ready with experience and advice.

Wait no, it's not like that, it is that!

Actually it's 2,000 people, with about 200 active daily. So you get a lot of viewpoints, and you get it quickly.

Recently two new developments have made the site even more fun:

Four new moderators

It takes love and devotion to curate a community like this, not only to delete spam but to help new members get involved, ask the right questions, and continue the spirit of constructive, respectful debate.

It's a lot of work for Dharmesh and I to do alone, so we've recruited four users to help out. These folks were already putting a lot of time into the website, were already proactively helping new folks, and were promoting the site externally, so they were all natural choices.

Please welcome:

• Bob Walsh of 47hats and StartupToDo.com (recently interviewed here)
• Jarie Bolander of The Daily MBA and author of Frustration-Free Technical Management.
• Tim of StackOverthrow.
• Jay Neely of Social Strategist and co-founder of EasyImpress.

Promote yourself with flair

Get one step closer to 37 pieces of flair!

You can embed a widget in your blog which shows off your (live) Answers reputation, like I'm doing now in the sidebar:

There's a few styles to choose from, or you can style it yourself, or you can really go nuts and use a web API to extract the live data programmatically.

Find instructions for all this using the "got flair?" link on your user profile page:

I hope to see you there! Join the fun.

Many of my mistakes can be traced back to a failure to recognize and appreciate "sunk cost."

The term comes from economics: "Sunk Cost" is money you've already spent and cannot get back no matter what. A "rational actor," as economists say, will completely ignore sunk costs when making decisions because the money is gone no matter what action is taken next.

Of course we carbon-based life forms can rarely be described as "rational," especially when it comes to ignoring sunk costs. It's hard to abandon projects in which you've poured time and money, especially when you've also attached your ego and reputation.

Sometimes it's easy to do the right thing. For example, let's say you designed a banner ad for a certain website (cost: $1000) and paid to run the ad for three months (cost: $2000). At the end of the three months, you look at the results and they're horrible — barely anyone clicked the ad and none of those people made a purchase.

Clearly you won't spend any more time or money on that ad. Yes you spent $3000, but that's a "sunk cost" — you cannot get that money back. Whether you had spent $30 or $30,000, it still wouldn't be worth continuing this project. Obvious!

And yet, throwing good money after bad is exactly what we do in many other situations. Here's a typical business example. A company is building a new $20 million manufacturing plant. They burn through the $20m, but it now it's clear that it will take another $10m to complete the project. In the meantime, an opportunity has appeared where they could take over and retrofit a different manufacturing plant for only $2m.

From a completely rational perspective, they should abandon the original project. The $20m they've spent can't be recovered (let's say), so it's now just a choice between spending $2m or $10m. Duh.

Of course the correct decision probably won't be made. You can imagine the internal politics of someone standing up and staying "I'm responsible for this hugely wasteful endeavor, and now I want you to trust my judgment as I pull the plug and do something completely different."

Here's where you expect me to say how stupid big-business is and how little startups are smart and agile and never make mistakes like that, but that's crap.

It's not just politics, it's human nature. Depending on which way you approach it, the term is "Loss Aversion" or the "Endowment Effect," subtly different but close enough for our purposes.

In short: We place excessive value on that which we own, or which we perceive we own. There's all sorts of fun experiments demonstrating this:

• At Duke University there are far more students wanting to attend games than there are tickets, so a complex lottery system determines who gets the precious few. Experimenters posing as scalpers determined that those who lost the lottery would on average pay $170 for a ticket. When they approached students who won the lottery, they were willing to part with the ticket for an average $2,400. Both students went through the same effort to get tickets, but those who own these (randomly-assigned) tickets ascribed a much larger value to them.
• Horse bettors who have already placed their bets (a sunk cost, "owning" a particular outcome) are more optimistic about their chances of winning then those who are still in line to place bets.
• Most people will not walk out of a movie they hate, because that would "waste money," even though the money cannot be recovered and they could be doing something more enjoyable.
• Just touching an item in a store makes you more likely to purchase it.

It's one of those things so deeply ingrained that it's hard to change your gut reaction even when you're aware of the problem. But that's exactly why you have to be especially vigilant.

So where in my life of startups has this crept up and bit me? And possibly you too?

• You've created an awesome feature. It was hard to implement and you're proud of it. Problem is, it turns out your customers don't care about it, and it's starting to create confusion and cause bugs. It's hard to kill your pet feature, especially after all this effort, and after all customer XYZ agrees that it's super neat-o. But that effort is sunk whether or not it's the right fit for your product; kill the feature.
• After hours of brainstorming, arguing, and banana daiquiris, you've finally come up with a clever, fun, catchy marketing slogan. Problem is, it doesn't quite fit the business. You don't want to "waste" this great concept; surely you can use it somehow, somewhere? No. As with all writing, you have to learn how to throw things out.
• Your newest hire isn't working out. You did everything you could during the interview; he passed all the tests. Still, he's not a culture fit, he's not picking things up as fast as you'd like, and everyone else is having to pick up the slack, which they resent. But, you think, it was so much work finding him and we've put all this effort into training him; maybe he'll change? But he won't, and deep down you know that. You can't get that time back, and yes this is one of the most expensive mistakes you can make, but even worse is prolonging the inevitable. (It's bad for the employee too — he deserves a chance to find a job where he can be successful.)
• You try a marketing effort and it doesn't work. That's OK, that's what A/B tests are for! So you test a pair, and the second one is a little better but not much. And then you iterate again, and again, and .... again .... When will you stop and realize that sometimes incremental iteration isn't enough?
• You're trying to land a 500-seat sale with a big-name company. The trial has gone on for 9 months. They keep finding reasons they can't buy — "deal-breaker" features they need, "critical" bugs they can't work around, budget allocations that never materialize. But that sale would mean so much, and besides you've already spent hundreds of hours with them and added all these special features so surely they'll buy from you eventually! But in my experience they often won't, or they'll buy just 10 seats so you can't claim they're "still trialing." All this is just an indicator that you don't have a good fit; this time-suck isn't going to vanish once they buy. Let it go. You need profitable customers, not just customers.
• You went to school for Biology, so clearly you have to have a career in Biology! Nevermind that you made that career choice when you were a teenager and hadn't really discovered who you were, what makes you happy, or where your talents lie. Your friends and family expect you to get a job as a lab rat and regale them with stories about diseased bovine spleens while everyone's eating meatloaf. Should you really throw away all that work and all those expectations to follow your true dream of becoming a caterer?

It's perfectly natural to feel attached to your sunk costs. It sucks to acknowledge that you've wasted time, money, energy, and reputation.

But it's even worse to irrationally prolong the waste.

Do you have stories or advice about sunk costs? Leave a comment and join the conversation!

I guest-post on other blogs fairly regularly, but it was pointed out to me by rising blogging star Ash Maurya that I don't usually share these with you!

So here's a selection of articles I've published elsewhere.

Four ways to get automatically rejected by an Angel investor
(VentureBeat)

Advice on pitching Angel investors who often have different criteria than the typical VC. Also see my follow-up article: Four more ways.

I've been pitched a lot, especially as a Capital Factory mentor, so this comes not only from my own experience but in discussing pitches with dozens of other angel investors.

Ten ways to make your writing more compelling
(Copyblogger)

Well, that was my title... it was edited to "10 Secrets to More Magnetic Copy," but that's OK, they were on a "magnetic copy" series binge at the time, and it made the "Best of Copyblogger 2009" list.  Sweet!

What was the trick to writing about writing in a fresh way?  The format was self-referential, e.g. using repetition when describing repetition.

Why your startup shouldn't copy 37signals or FogCreek
(OnStartups)

A controversial post about why you shouldn't blindly follow bloggers or celebrities. Interestingly Jason Fried at 37signals agreed but I ended up pissing of the folks at Copyblogger (later mended, as evidenced by my guest posting there). I wrote up the full behind-the-scenes story.

How to get hired at a startup and
How to write a cover letter that actually gets read
(WorkAwesome)

Both of these are aimed at the employee rather than the employer. Still, no matter which side of the table you're on, this is useful for your hiring process. Some of this stuff you might have heard, but between them these articles were retweeted over 1000 times so apparently it needed to be said!

How a smart bear built a company so he could sell it (Video)
(Mixergy)

Andrew Warner, the interview host, summarized it well:

"My hands were trembling as I was faxing eighty pages of the agreement over to the lawyers in New York City," Jason Cohen said about what it was like to finalize the sale of the company he founded, Smart Bear. Even though he was nervous about the sale, selling the company was his plan all along.

In this interview, you'll hear why he wanted to sell his business, and how he prepared for a sale as he built up his business. You'll learn how he founded it from scratch, with no venture funding and no debt. And you'll get his advice for how you can build your business.

Now two questions for you; please answer in the comments:

1. Want to see more of these?
   (i.e. Should I let you know about guest posts more regularly?)
2. Want to see other people guest-post here?
   (i.e. Do you come here for my opinions alone or would you enjoy other voices?)

Nothing clarifies things quite like a hyperactive, all-knowing, all-seeing, real asshole of a devil's advocate beating the living crap out of you.

(Cartoon by Andertoons)

Baseball players swing heavy bats before going up to the plate; acclimating to difficult working conditions makes it easier to hit the ball out of the park.

What's the equivalent of the heavy bat for honing your skills at pitching your product and raising money for your company?

For years I've been a fan of Scott Berkun's concept of Rude Q&A:

What would the meanest, nastiest, but smartest people in the world grill you on when you show your work?

A Rude Q&A is a list of questions [about your work that] you don't want to hear.

When you're contemplating an exciting new idea, you don't want to hear questions that might contradict your concept.

And of course, that's exactly when you need the biggest, baddest, smartest, devil's advocate to challenge all your assumptions.

It's not just about testing the mettle of your ideas, it also forces you to refine and clarify your marketing messages, your target customer profile, and your feature set. When you're being grilled there's no room for being generic about how you're different from the competition, no leniency for not knowing exactly what customer pain you solve, and no clemency for wavering on your company values and what compromises you're willing to make.

Scott goes on to explain just how unfair the questions need to be:

Make sure to include questions that are unfair or based on erroneous information. Reporters, clients, and the public all have their share of unfair questions and erroneous information, and you want to be ready for them.

These answers take more time as the responses need to be more polite and mature than the questions. They also need to carefully refute assumptions in the questions without being dismissive.

I love it; now we're deep into "heavy bat" territory.

So how do you go about writing your Rude Q&A? Oddly, the hardest part can be coming up with the questions.

To get you started, I've assembled a laundry list of questions common to many startups:

• Your biggest competitor just dropped their price to $0. How do you continue to justify your price point?
• If your idea is any good, you'll have competition from multiple players, both funded and bootstrapped, both smart and stupid, both large and small. How will you persevere?
• If the economy stays bad for two more years, how will you survive?
• The last thing anyone needs is another damn tool. What's the overwhelming reason I should even bother looking at you?
• Technorati reports one million new blog posts appear every day. Why should I read yours?
• What are the top three features your competitor has that you lack? How do you address that today, and what are you doing about it in the next six months?
• How can you call yourself an expert when you've only been at this for a year?
• What are three tangible, undeniable ways in which your product/company saves more money than you cost and saves more time than you consume?
• Truly great products and companies are rare, even when smart people are at the helm. What makes you think you have what it takes?
• There are thousands of consultants who make the same basic claims you make: high-quality, on-time, on-budget, good service, happy customers. What makes you any different?

These are generic; you'll need to come up with more specific attacks. For example, if I were defending this blog and answering the question about why anyone should read it, I would make the question more specific:

There are already too many blogs about startups, especially high-tech startups. Those blogs are far more popular than yours, their authors far more famous, and their advice is excellent. Smart Bear is a success but it's nothing like the success earned by someone like Steve Blank. Why should anyone listen to you?

And here's my answer:

I read those blogs; they're great! But the world needs more perspectives, not fewer.

For every Jason Fried who says "simple design is better than complex features," someone else needs to point out that they've (I've!) made millions with poor graphic design and too many features. For every Seth Godin who says a tribe of 1,000 followers is all you need, someone else needs to point out that it's not true in practice.

The biggest reason to read is that my advice and perspective, while not a massive thought-revolution in the universe, is "unique enough" that I constantly meet intelligent, capable, thoughtful entrepreneurs who haven't heard it before, haven't thought of it themselves, and whose lives and companies are improved after they've heard it, even when they disagree with my point of view.

I know this because of the comments and wonderful emails I receive. As long as people keep saying that I've lifted a burden off their chest or produced invaluable customer feedback or prevented them from wasting time and money, or even if they just get a laugh, that's my answer to why anyone should listen.

Don't get discouraged if you're not happy with all your answers. That's a good sign — it means you're being honest about the exercise and you're not yet satisfied. Keep it in the back of your mind and look for answers while you forge ahead. Discuss the hard ones with other people to get more ideas.

This is all just another way of being introspective, but it's a technique I've found to be particular useful.

Do you have more Q&A to contribute? Leave a comment!