Give it a listen today!

The Business of Software Conference starting today in Boston is live streaming, beginning at 9am Eastern. If you want to hear and watch some of the sharpest minds in the software business, get yourself registered on this page and start partaking.

Here’s the speaker schedule, with my personal favorites/recommendations in bold
(All times are Eastern):

Monday, October 24th

  • 9:00 AM – 10:30 AM Clayton Christensen – How to Create New Growth Businesses in a Risk-Minimizing Environment
  • 10:45 AM – 11:45 AM Jason Cohen – Naked Business: How I made more money through honesty than through typical business behavior.)
  • 11:45 AM – 12:45 PM Alex Osterwalder – Building Competitive Advantage through Business Model Thinking
  • 2:00 PM – 3:00 PM Dharmesh Shah – Insights And Musings On The Business of Software
  • 4:45 PM – 5:45 PM Jeff Lawson
  • 5:45 PM – 6:15 PM Tobias Lütke – How to make sure your business is on the right side of history through code and culture.

Tuesday, October 25th

  • 9:00 AM – 10:00 AM Patrick McKenzie – Engineering Your Marketing Outcomes
  • 10:15 AM – 11:15 AM Laura Fitton
  • 11:15 AM – 12:15 PM Josh Linkner – Unleashing Creativity
  • 1:30 PM – 2:30 PM Rory Sutherland – Praxeology: Lessons from a lost science
  • 2:30 PM – 3:15 PM Lightning Talks Five finalists present 15 slides in 30 seconds each. That’s 7 minutes 30 seconds, then sit down.
  • Corey Reid, Freshbooks
  • Karl Treier, Prospect Stream
  • Patrick Foley, Microsoft
  • Justin Goeres, JKI
  • Tyler Rooney, 4ormat
  • 3:45 PM – 4:45 PM Michael McDerment – CEO and Co-Founder of Freshbooks.
  • 4:45 PM – 5:45 PM Peldi & John Nese – An Interview with John Nese

Wednesday, October 26th

  • 9:00 AM – 10:00 AM Paul Kenny – The art of asking!
  • 10:15 AM – 11:15 AM David Cancel
  • 11:15 AM – 12:15 PM Alexis Ohanian
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Bob WalshGive it a listen today!

Give me what I want

Okay! There’s countless small and large projects that need to be accomplished on the road to a successful self-funded startup; don’t be shy asking for what you’d like to see here. 

Starting today, you’ll find the Y Project has its own page, and you can vote which post you want to see me research and write next:

Which of these posts would you like to see me research and write?

View Results

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Interested in something else? Comment here or on the Y Project page.

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Bob WalshGive me what I want

Finding a great startup domain name

There’s thousands of advice posts on picking a domain name; In this post I’ll try to filter down to the few most important ideas, take a quick look at how the interaction between name and market focus work, and share 6 online tools that I found useful in my hunt for Project Y’s URL.

The basics

Let’s start with the obvious traits of a good URL:

  • The shorter the better,
  • Catchy,
  • Easy to spell and pronounce,
  • Be .com if at all possible,
  • Not give some other company cause to sue your startup for trademark infringement,
  • Perfect for your startup now and until it’s larger than Google.

(That last bullet is not going to happen, especially if you fixate on finding the perfect domain name instead of accepting the reality that you’re looking for a good enough solution based on a reasonable amount of time – say 2 hours – spent on this.)

Discoverable or Brandable?

All that is fine, but it’s not enough. Here’s an question from a Smashing Mag post that cuts to the heart of the matter: Discoverable or Brandable? Are you looking for a domain name that has something to do with what your startup will be selling, or are you looking for a word – real or not – that you can build a brand around?

There is no one right answer to this, but I think if you’re building a self-funded startup, a discoverable domain name, a URL that contains or connects to the problem domain you are addressing makes the most sense.

First, your Prime Enemy as self-funded startup is obscurity: literally every decision you make needs to gravitate towards increasing your Internet exposure, reach and discoverability. Second, building a brand takes time, money, and more money. That’s not in the realm of the doable for you if you’re self funding.

If you take a look at some of the best known brand names in tech – Microsoft, Google and Twitter jump to mind – these names connect with the core ideas (software for micro versus minicomputers, a whole lot of something, and incessant, background communication) – they were discoverable long before they became brandable.

So how do you make a startup “discoverable” via just a short character string? Here’s two words that help: metaphor and portmanteau.

  • A good metaphor packs a lot of information, context and emotion into a small useful package. For example, when you see a job posting for a rockstar programmer, they’re not talking about your musical ability, they’re telegraphing they want someone who stands out from the crowd.
  • A portmanteau is a freshly minted term that combines two objects or ideas, for example smog, wikipedia and spork.

Since you’re building a startup, you should be in the business of creating something new. Think about what widely recognized ideas/associations/keywords orbit your solution and its problem, and how you might be able to combine one of those words with the emotional payload of your product.

Domain naming tools

Here’s an assortment of sites you’ll want to open in your browser when you sit down to find your startup’s domain:

  • Domainr – If the perfect .com URL is already owned, what about some top level domain varient like or Domainr makes it easy to find these kinds of URLs, but the easy way out now means a business lifetime of having to explain just how to spell your domain.
  • Domize – While sites abound that will let you perform a quick URL check, I think Domize performs this service without irradiating your eyeballs with dozens of ads. Its ajax-enabled results list is fast and useful, letting you cover more possiblities.
  • Domainsbot – Is a shotgun approach, quickly generating hundreds of variations.
  • Looking for another word that might be less domainized? Check out both VisuWords and VisualThesaurus to help you.
  • My favorite domain-finding tool is the Merriam-Webster Visual Dictionary Online – enter a word, like say peg, and see what it actually is – a very handy way (see below) of finding physically related objects that may be less used in domain names, but still on target.

Welcome to the Jason Test!

So how do you test a domain Name? Jason Cohen, serial startup founder and founder of, has a bit of wisdom that makes testing domain names easy:

What can I tell about your startup just from its domain name?

My twist on this: For your target market, what does that domain name say about your startup? I don’t care what high school students, people studying a language, or premeds trying to swot all that terminology (although I might one day); I want to know working developers and the like think of the domain name.

Asking 5 people “what do you think does?” is a great way of gauging just how discoverable your name is. Five is what I consider a quick measurement – the more the better. Asking 20 people who are members of your target market what they think your domain name means is a great start down the customer discovery path.

Put it to the test Bob!

Originally, I was thinking Y would be a more general tool than just for developers who need to commit to long term memory massive amounts of knowledge. Repeatedly, I struck out finding a domain name. Interestingly enough, when I decided to narrow this app to a specific market (another post for another day), it got considerably easier to find a good domain name.

Given my working definition of Project Y as a solution for (“online folk who need a streamlined way to get info from the web into their own personal long term memory“) what’s a good URL? Y is about memory and “online folk” primarily developers: bingo! Say hello to

As I researched this article, and I was playing around with the various URL tools, I came up with an alternative – Specifically, I was checking the Merriam-Webster Visual Dictionary Online for the word peg, realized that a peg is both a term often used in memory systems and “a detachable part inserted into one of the openings on the work surface to clamp an object between its jaws.” While is taken, it led me to (also taken) and then and is good, but it’s too broad for the app I’m doing. (If I were a funded startup bent on revolutionizing the memory capacity of humanity for a small monthly fee, it would definitely work. Go for it if you’re so inclined.)

Wrap it up

Here’s what I’d suggest as a working heuristic for finding your startup’s name in the Internet heavens:

  1. Obey the basic rules of good URL naming,
  2. Isolate the key concepts/markets/associations relevant to your app,
  3. Use fast online tools to check for availability and variations of those concepts and to dig deeper into those concepts looking for more market relevant variations.
  4. Apply the Jason Test: What does your domain name mean to your target market?
  5. Repeat until you have a winner – but don’t waste time trying to find the perfect domain name.

I field tested with a 5 friends via IM and liked the results. Now it’s your turn:

What do you think is about? Please add your comment!

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Bob WalshFinding a great startup domain name

Remember the future with

(A while back I’d planned to launch a new productivity site,, but it makes more sense to fold that effort into 47Hats. So, here’s the first of a series of posts on tools and services for improved online productivity. Note the .pdf download at the end of the post! :))

The more people you interact with in, the harder it is to remember to follow up with them. Enter (FUT) – an elegant alternative to missed deadlines, dropped conversations, and things in general falling through the cracks.
Here’s a few examples of what this free service can do for you, starting right now:

  • You email a friend, coworker, your boss a question. More times than not, if they don’t reply you won’t remember. Instead, you BCC and three days later you get a reminder from FUT with a copy of your email.
  • Your girlfriend, boyfriend or just a friend has an important event coming up in a few months. Usually you’d shortchange them and you because you either forget it entirely, or don’t prepare to do it right. With FUT, you slap together and an email with info on the event – say your anniversary – a couple of to do’s (get flowers, gift) and email that to Come March 12th, you get that email back – just when you need it.
  • You’re working on a project and have nailed down who is supposed to do what. You’ve got what you have to do neatly tucked away in your GTD system, but do they? In the recap email you send CC and all recepients will get a reminder email every friday until you turn this off. Don’t like the generic look of that reminder? Spend $24 for the year to upgrade and add your logo, custom colors and custom explanation, and remind via SMS.

FUT is elegant – for the price of adding an email address, you get back a clear reminder exactly when you need it. No more wasting time emailing back and forth “Have you looked at x,y and z yet?” “no I haven’t can you send me that email again?”
I’ve been using FUT for two months now to:

  • Make sure to send my girlfriend’s weekly timesheet in on Sundays at 4pm.
  • Remember to evaluate that awesome new online tool I just signed up for before the free trial expires (
  • Remind me when a book by an author I like is set to go on sale at Amazon so I can don’t waste my time checking again.
  • Send low value emails I need to respond to my least productive time of the week (

To start using the, just email

  • 47hats Extra
    47hats Extra

    47hats premium content

  • A Extra for you.

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Bob WalshRemember the future with

Starting something new… Project Y.

One of the weirder things I do is tackle multiple problems with one solution. Sometimes it works, sometimes not, but it tends to make life… interesting.

So here are the problems I’m out to solve:

  • I’m looking for a big fat hook I can hang great content on here, that you’re going to want to read and remark on. I can write about a lot of things, but it’s more fun, useful and interesting when they tie together into something bigger.
  • I need to get back into developing. While I love to write and am pretty good at it, there was a reason I got out of reporting – I want to build things, not just talk about them. Having done zero coding for nearly a year, I need to build up my programmer muscles, and get back up to speed with what’s going on in the Rails community these days (short answer: a lot! 3.1, CoffeeScript, Saas, jQuery…!). And there’s the not small motivation that developing in Rails pays well, but you need to be able to show you can do the job as it’s defined today, not a year ago. (digression: Railcasts has just added premium ‘casts – sign. up. now.)
  • I’m writing this book, WordPress for Startups, and while I like where it’s going, I want to include in it a real startup’s site that I can mercilessly critique. Volunteers for public beatings are not abundant.
  • I’ve been doing way more reading/talking this past year about the humanity-wide social media party in progress than actually participating. It’s time to go back in and enjoy the party, and that means bringing something to share.
  • Getting older is a drag, and the box I in my head where I store all that programming knowledge needs a good clean out and refurbishing. As easy as it is to Google everything (Stack Overflow everything), I want a better way of learning how to proficiently and fluently code. Have looked all over the interwebs and while there are flashcard/memorization dorky web apps for students, there’s nothing I’ve found suits aging online entrepreneur developers who need to learn 2.5+ programming languages fast. Sounds like an unmet need to me!
So, here’s my solution: Build a useful web app for online folk who need a streamlined way to get info from the web into their own personal long term memory. Detail here what I learn about what works and doesn’t work – circa late 2011 – as I tackle all those not the actual coding issues that every self-funded startup founder has to grapple with. Rinse, lather, repeat.
First up – Picking a URL.
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Bob WalshStarting something new… Project Y.

Missing Steve, Reason #1: the “Internal Error Occurred” debacle.

I miss Steve. I miss him a lot. Especially after spending the past 4 hours trapped in the “Internal Error Occurred” debacle (reported herehere, and even here, and anywhere else Apple-centric on the web), unsuccessfully upgrading my iPad and iPhone to iOS5.

For my snickering Windows friends (I’m thinking of you, Pat!), today’s waste of what could have been a productive day began by being the good early adopter and pounding away at the iTunes upgrade button since 5am, then receiving the anointed Best New Thing about 10am, waiting about an hour for the inescapable backup, install, and then after all that, install fails with a bullshit “internal error occurred.” Again and again and again.

(* Image above is what you get if you try the “let’s restore not upgrade” solution. At least it’s honest. Stupidly lame, but honest.)

Contrast the “Internal Error Occurred” debacle to the Lion OS upgrade of July 20th – which was the most uneventful OS upgrade, ever, a month before Steve stepped down.



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Bob WalshMissing Steve, Reason #1: the “Internal Error Occurred” debacle.

Here, we go, again.

Whirr. Click. Clank! Reboot complete – 47hats is back! Having taken a long virtual walk to clear my head about what I want to do here, I’m writing again about what matters to me (and hopefully you): the Startup World, productivity in the early days of the Internet Age, and sundry other topics.

Redoing this site has been very much a case of eating my own dog food (or in my case cat food): I’ve been taking my own advice from WordPress for Startups, my next book. WordPress is an awesomely powerful codebase for anyone who wants to build a great site for their business without spending huge amounts of time and money. But like a lot of the progeny of the Internet, understanding some of the deeper truths about it helps:

  • A lot happens in a few Internet years. The workflows that made sense a few years ago can come back to bite you now. Case in point: Featured Images in posts, added to WordPress about two years ago, gave theme developers lots of new functionality to work with. That’s the good news. The bad news comes in if you’re ignored this new feature. If you just keep adding images to posts the way you used to pre-Featured Images, you could end up a corpus of 700+ posts that as far as modern themes are concerned are just so much text. Ouch. Which brings me to point 2:
  • Look within your given online community for who’s already solved your problem. The number 1 reason to do you site in WordPress has to be the hundreds of thousands of developers, designers and artists who are part of the WordPress Community. For example those 700+ posts I’d have to go through manually to generate featured images for. Let me introduce you one of the 16,000+ WordPress Plugins: Generate Post Thumbnails. Install it, run it, and let it do the heavy lifting for you.
  • When adopting major software, or components for that software, there’s no such thing as having too much support. It can be an enlightening experience as software developer when you start getting jabbed in the side by some other developer’s idea of what you should be doing with their creation. If there’s one thing 30 years of dealing with software has taught me is that every single application has built into its core a set of assumptions about the world, what problem it is solving and what is the “right” way to solve that problem. If you situation is different, you’re mileage will vary. A lot. And that when you are going to want help.
  • Accept un-perfection and move on. There will be times when the effort cost of fixing something is way too expensive. For instance, either manually editing and resaving each of 700+ posts to not use use features images when displaying just the post, or running a fairly complex SQL query on my (don’t touch it!) WP database to generate the needed records in wp-postmeta. So, I’ve done the last dozen or so posts, and the rest will have to wait for a while.
Anyway – So how do you like the new look and feel of 47hats?
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Bob WalshHere, we go, again.

Lies, Damn Lies! and Time Management

Note: The following screed is brought to in the public interest. If you’ve wouldn’t in a million years put the words “time” and “management” together, feel free to skip. :)

I started reading Jenny Blake’s fine Life After College: The Complete Guide to Getting What You Want this morning (Jenny: need a Life Way After College sequel and Kindle version!), and was globsmacked when I read the phrase “time management” in the intro. I’m looking forward to reading the entire book, but I just had to pound out this post.

“Time Management” is a poisoned meme; ingesting it any way, shape, form or media is a very, very bad idea.

I know, I know, you’ll say it’s just a shorthand for all the practices and methods aimed at improving personal productivity; you are probably googling right now where I’ve used the same phrase. Consider this post an act of contrition.

There never has, and there probably will never be, such a thing as “time management.” Time, at least for those who don’t get to play with supercolliders for a living, is a constant. It cannot be speeded up or slowed down or stuffed with extra needed hours. And, unless you’ve hotwired your genitals to an alarm clock, nothing, but nothing, happens at exactly at the start of any hour.

Time management” in the last century went hand in hand with industrialism: a punctual (and time clock punching) workforce was a necessary prerequisite to manufacturing, and “scientific” management. But that was then, and this is now, and if you are reading this post you no more punch a clock than I do. So why let a catchword of the industrial age shape your thinking in this post-industrial society?

If I told you the first step to becoming more productive, to getting what you want from life, to success however you define it was “gravity management”, you’d laugh in my face. Trying to become more productive by managing time is no more an idiotic idea – and what a terrible waste it is trying to achieve it!

Words have power. And meme’s – conceptions of reality freeze-dried into phrases we seldom examine – can go boom in your face.


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Lies, Damn Lies! and Time Management

You have data. What you need is DigMyData.

So there you are, with your startup wired up with every type of analytic instrumentation you could ask for. You got your Google Analytics, Google AdWords, your email engagement program of choice (it really ought to be MailChimp, IMO). And you have your social media data – how many Twitter followers you have, what people on Facebook think of you, how many people read your blog. To top it off, you’ve got your sales data in one form or another, and whatever other stats you’ve bought into.

And you know what all this data will do for you? Not one single thing. It’s just raw data–it doesn’t do anything. It’s your job to figure out what all this data means, how each of these different streams of information interrelate. Then, and only then, have you got actionable information so you can do more of what works, less of what doesn’t.

That’s where comes in. You don’t need more facts, you’ve already got all the facts: what you need is a way to see all of the data you need in one place, at one time, on one screen. If you’ve ever tried to figure out if what you are doing is actually working based on all of your numbers – web site, email, social, revenue – you will want to put DigMyData to work immediately.

This online service is about asking questions, getting answers – answers that let you change where your startup is going. When you post and tweet more, do you sales go up? That day, that week, that month? When you post a video to YouTube, do the number of tech support emails/tickets drop, or rise? What happens in Google Analytics when you spend more time doing tech support and less on social media – nothing, more visits to the right pages that lead to a sale? What?

In a nutshell, you pick which types and sources of data you want to give DigMyData access to. Then you create not just comparison charts (Adwords spending vs. number of tweets/posts, etc.), but annotate that data with scenarios that you can test, and actions you’ve taken. For example, if during the rest of this month you do X, what do you predict will be the results in terms of revenue? Moreover, actions you take – improving your SEO, reaching out to talk to at least one customer a day for 15 minutes, updating your site – will be reflected in your data. With DigMyData, you can add those actions and scenarios as story points in your startup’s timeline, so when you look back in 3 weeks, months or whenever, you can see in the data their positive (or negative) effects.

I’ve been using DigMyData with one consulting client for the past 6 months and will continue using it as launches and WordPress for Startups goes on sale. Today is DigMyData’s official launch date, and they’re offering an extended free trial if you sign up now that runs the rest of 2011 so you can really see results. It’s a powerful, unique way to not just consume data but test scenarios and make decisions. Highly recommended.

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Bob WalshYou have data. What you need is DigMyData.

Taking Charge of your Startup’s Scheduling

By Mark L. Smith, Co-Founder

Momentum is the life blood of a startup. Nothing gums up the works and kills momentum like scheduling difficulties — timezones, multiple availability schedules, holidays. It’s a wonder sometimes that anything gets scheduled at all.

We absolutely love our product vision at DigMyData and we love using our own tool to tell our business stories. As a result, we schedule a lot of meetings with people all over the world to both pitch our product and to help them with the initial setup of DigMyData. We use Tungle to manage this scheduling and keep up the “big mo’.”

What is Tungle?

Tungle is a cross-company scheduling tool that solves timezone and availability issues. It allows the meeting initiator to “paint” in the time they can meet and send e-mail invitation to one or more meeting attendees. The other meeting attendees paint in their availability and the last attendee gets to pick from a list of times that work for everyone else. Tungle can integrate directly with Google Calendar and Outlook to automatically manage the painting process.

What we use it for:

We use Tungle for prospecting. When we want to talk with people about our product, we paint in our availability and send a Tungle invite to our prospect. How many of your prospects go cold because they’re used to frictionless scheduling with people inside of their company? You often don’t know because you never get a response. Tungle keeps that stuff from happening.

We also use Tungle for support. Tungle lets us plug our Google Calendar availability into a special site. Our customers can visit our site and book a meeting directly — we get an e-mail notification and it automatically shows up on our Google Calendar. Customers are most likely to do a support session with us if it is easy for them to do — which makes it more likely they will stay customers.

What we love about Tungle:

  • Solves timezone issues.
  • Keeps the mechanics of scheduling from getting in the way of great conversations.
  • Great if you use Google Calendar — easy connection (shows busy times, puts it right on your calendar, etc…).
  • Great for setting up meetings with more than 2 people.
  • Free!

What’s bad:

  • People who get it, get it. People who don’t, don’t. In our experience, the people who are most likely to give our Tungle invites the “sideways puppy dog look of confusion” are Outlook/Exchange users in large companies.
  • Tungle was recently acquired by RIM — makers of BlackBerry. I’m an ex-BlackBerry user. I’m concerned that RIM will ruin Tungle.

Our tips to get the most out of Tungle.

  • Setup your page and include your profile info. Send that link to people when you reach out to ask for a meeting. The links look like this:
  • When asking someone to Tungle a meeting with you, go ahead and tell them what call-in information to use (you call me, I call you, we use this #, etc…).
  • We use for on-demand screen sharing instead of worrying about scheduling a WebEx or GotoMeeting session. When we are on the phone it is very easy to to tell someone to A) go to B) type in a phone # length code.
  • Check your Tungle settings! I like making schedulers give me at least 2 hours advance notice for meetings — that way, I have time to notice it in my calendar.
  • Be realistic on setting your availability — bankers hours are fine :)


A typical DigMyData call goes like this: We talk with a customer or potential customer over Skype using with a Tungle scheduled meeting. It’s all free and just works. Reduce friction; keep up the momentum!


This guest-post was written by Mark L. Smith, Co-Founder of DigMyData, a storytelling tool for web businesses. Follow @DigMyData on Twitter.

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Bob WalshTaking Charge of your Startup’s Scheduling