Here’s a neat feature I discovered today with smart playlists in iTunes that automatically keeps some fresh music on your iPod. If you’re like me you initially sync’d a bunch of songs to your iPod/iPhone when you first got it and haven’t changed the music since. You have the new stuff via the “recently added” playlist but there’s a huge body of older music that resides exclusively on your computer in your iTunes so it never sees the light of day on your iPod. Here’s a technique to automatically keep your iPod fresh:

1. In iTunes go to File > New Smart Playlist and create the following rule:
   
   Name that playlist something like “fresh songs.”
2. The way mine is set up I have playlist called “iPhone” and my iTunes is set so it selectively syncs only that playlist to my iPhone. So now drag the “fresh songs” smart list on top of the “iPhone” list.

Now each time you sync it will scan your library and add 50 random new songs you haven’t listened to in the last 6mos. You’ll have a rotating body of new music at all times on your iPod.

Another suggestion for escaping a musical rut if you’re in one is to try the Rdio service. I was on their beta for a few months and I’m now a paying customer. I highly recommend their service. It gives you all-u-can-eat streaming music and works great on the iPhone. It even has the capability to sync songs for offline use so you can listen to them on an airplane. I’ve found the coolest aspect is the spontaneity of being out with friends when someone says “remember that one song” and being able to pull it up and play it on the spot. If you want an Rdio invite leave a comment – I have a few left to give.

Here’s a simple proposal: if you’re calling yourself an Angel Investor at an event, you should wear a standard name tag that gives an objective measure of some basic facts about your “nutritional content” as an Angel.

At least in AZ, the term “Angel” seems to have been co-opted by anyone who has ever bought a piece of real estate. After holding a piece of dirt and making money, these people are somehow magically imbued with divine powers to forsee why your technology startup won’t possibly work (and they’re happy to prognosticate about it).

I was at an event last night helping a friend pitch his company and one of the panelists (who shall remain unnamed) made the repeated feedback to the presenters that “you didn’t specify what my return will be.” Sir, frankly if that’s the only feedback you have for these entrepreneurs pitching their early-stage, pre-revenue technology startups, you do not deserve the title Angel. Go buy a treasury bond and the bankers will happily explain what your return will be.

At this stage in the search for the repeatable scalable business model, companies have no f’ing clue what the return on your $50k is going to be. And it’s a silly tapdance you put them through when you force them to fabricate and justify one. The idea is to make it as big as possible – we all agree on that right?

If you’re a VC adding fuel to a finely tuned business model where the formula has been determined and tested, by all means ask the entrepreneur to calculate and substantiate what the return will be. At that point that exercise makes sense. But at this pre-revenue stage by asking this question you’ve self-identified yourself as being unsophisticated, focused on the wrong motivation of Angel-stage investing and frankly you’re not someone whose money I would want at that point. At the Angel stage the entrepreneur has demonstrated the ability to create a product which appears viable. You’re funding their search for the repeatable scalable business model, not putting gas in the engine of a working model. Think of it as a more interesting/rewarding alternative to throwing your $50k down on a craps table in Vegas. If you’re treating it like a blue chip stock and can’t afford to lose that money you shouldn’t be doing Angel investing.

Note: I’m not proposing regulation on Angel Investing, I’m proposing a standard for Angels self-reporting some basic traits to the folks who are pitching you. This objective label would do two important things: 1) for the budding entrepreneur, it gives him/her the ability to assign a level of credence to the words coming from the person telling them why they’re going to fail. 2) for the Angel, it forces them to admit publicly how many deals he/she actual does at the end of the day. The guy with the “Deals last year = 0″ label on his breast pocket will likely think twice next time before he publicly craps on a guy starting a company for the first time.

I love Google Voice. We use it as our main office line at JumpBox and it gives us a lot of flexibility in handling the phones. We can setup call windows for business hours where it rings my cell during the day and goes direct to voicemail in the evenings and on weekends. We get transcribed emails for each voicemail so we can quickly skim the content before listening to a long message. And we can very easily re-route calls to a different phone if I’m out for some reason.

But there is one feature that is so conspicuously absent that either I’m fundamentally misunderstanding the service or it’s a major oversight in how it works. The quickest way to explain the issue is to show what I want added to the voicemail interface (circled in red):

The current problem is this: if Google Voice rings my cell phone and I miss a call during the day it goes to my AT&T voicemail. That’s problematic for a couple reasons, namely: 1) I’m the only one with access to it 2) the caller gets a personal greeting from me instead of the expected company message 3) it fragments where our messages are stored into two places 4) we lose the nicety of call transcription.

The ideal solution here would be to have a threshold setting I can configure so it recognizes when I don’t pick up by the 3rd ring, takes the call back and re-routes it to the GV voicemail.

Is there some obvious setting I’m missing to make it behave this way? If not, Google peeps: this would be a hugely valuable / simple feature to add. I have to imagine others face this situation and could benefit from it.

I’m back from a week in Boulder, CO for their Startup Week palooza and holy shnikes was it a neat series of events. I wanted to do a braindump of my thoughts on the weekend while they’re fresh.

First, kudos to Andrew Hyde for pulling this thing together- what an amazing community they have up there. Paul Graham had written a post a few years ago that distilled the traits necessary to produce the next Silicon Valley. While Boulder is no SV (nor should it necessarily want to clone that) there is definitely something other than beer brewing in that town. And I’m not the only one this weekend that felt it – Chris from RWW (another AZ person) sensed the same thing.

What worked well

Plancast – this is an app that allows people to express their intentions of what events they’ll attend. This worked extremely well for coordinating things. It integrates w/ Twitter and FB and allows you to parachute into a situation and conveniently track what’s going on and schedule where you want to be. But it’s more because it allows you to connect w/ attendees after the fact so you don’t have to obsess over collecting people’s contact info while you’re enjoying the moment. I was skeptical of this app when I first heard about it because it has the same downside of LBS only amplified because you’re publicly projecting your intended location for the future. Well, I stand corrected: this is a kickass tool and I hope all conferences adopt it (or something like it).

Startup Crawl – I co-founded a company called Pubcrawl.net back in the day. We ran crawls in Phoenix and made a site which enabled 100+ other cities to run crawls of their own. We knew the magic interaction & serendipity that occurs when you get a group of people to travel together amongst interesting locations. This worked really well and I want to do something similar with the meetup group I run for techies in AZ. You meet the people in your group, learn about the companies that you visit and the whole thing is super-fun. The TempeNerd lunches have been somewhat anemic lately but I believe this tweak to the format will revive it and take it in a new and more social direction. Unfortunately Phoenix is so geographically disbursed it will be a challenge to find pockets of startups within walking distance but I have some ideas. I’ve put a picture set at the bottom of this post to give you a flavor for what the crawl was like.

Ignite Boulder – solid to very-solid. They rocked this event and nailed the major things you need to do:

• venue with character
• quality speakers
• flawless A/V execution
• likeable moderator
• live-streaming for remote folks
• intermission w/ beverages
• legit live music
• ice-breaker nametags
• a pre and post party for people to socialize

You get these core things right and you’ll naturally draw interesting people. Jeff Moriarity is kicking butt w/ our Ignite event here but we can definitely learn some lessons from Boulder’s.

The bigger picture

I told Andrew the bigger picture of what’s happening here is a “unification of the tribes.” Economy 2.0 is going to operate very differently from what we know today. The facts we do know at this point:

1. it’s unquestionably f#$%’d now and not going to fix itself.
2. entrepreneurship will play a prominent role in the recovery.
3. collaborative technical infrastructure has evolved to the point where people no longer need to be on-premise to participate effectively on a team.
4. while in-person presence is not essential to render work, there is no substitute for intermittent convergence of people who can then remain in contact afterwards via digital means.

I don’t know that Boulder represents the “next Silicon Valley” but I also don’t know that we need another Silicon Valley. Whatever it is it’s stacking up to be a hub of startup activity. The quality of their community is testament that they’re doing something right up there in the mountains. I’ll definitely be searching for an excuse to get back there next snowboarding season and looking forward to staying in contact w/ some of the people I met up there in the meantime.

Props to peeps

Random shout outs in no particular order to some of the interesting people and companies I hung out with up there: Chris Hough, Suzan Bond, the Tweety Got Back girls Heather and Rachel, Lane Becker of Get Satisfaction, Micah Baldwin of Graphic.ly, Joe Stump of Simple Geo, Ari Newman of Jive (formerly Filtrbox), Ben Brikerhoff (formerly of Devver), Brandon Harper and of course Jeremy & Andrew.

If we met and I haven’t connected with you on Twitter yet hit me up.

Thanks Boulder people for welcoming us travelers into your community this past week. You guys have at least one guaranteed couch here in Phx to crash on when you need it.

This is half rant / half proposal for a free business idea. I’ve gotten four emails in the past week from various entities (2 banks, 1 health insurance provider and 1 telephony carrier) that notify me of changes to their TOS (apparently I need to accept them if I want to continue being a customer). One of the documents was a 35pg PDF which presumably had a few sentences change since I first accepted it. Given how much we have going on in our company the effort involved in combing through that document vs. the likelihood of that task returning value all but condemns it to reside indefinitely at the bottom of my todo list.

A better way & an open letter to service providers

These verbiage haystacks are bad news. Your customers are busy people and while it may be in your best interest to cloak the tweaks to your policies that may stir up unrest amongst your customers, this practice is asinine. Publish the damn “patch” to the TOS so we can skim it, see the crux of what changed and rapidly make a decision about whether we agree the tradeoff is worth it to remain your customer.

Yes, your attrition rate will go up as a result (and it should) But the thinking that “we’ll just bury the new stuff in the huge doc and people will accept it out of frustration/lack of time” is hugely short-sighted. We already know 88% of the people don’t read the TOS the first time, you think that % is going to be any better when you ask them to re-read a slightly-modified version a few months from now? While you may get a short term attrition benefit w/ the current method you’ll eventually end up with angry rants from pissed off customers higher support costs from fielding inquiries caused by inaccurate expectations. By doing it the way you are now you set the stage for an inevitable exodus of angry customers to your closest competitor that respects the value of their customers’ time. And the loyalty they earn by making it easier to stay informed and make faster decisions is priceless – you will not see the people that defect specifically for this reason again. And they will be vocal about their exit.

Abstracting this to a business idea

So the meta from this is that there’s an opportunity for someone to deliver “Policy as a service” to companies. Us geeks can figure out how to put docs in source control or publish pages that automatically highlight the diff from the last version. But for the rest of the world the path of least resistance to writing/reading is creating a new PDF and expecting readers to comb through the whole doc.

Someone should develop a simple service that allows companies to publish policy docs (TOS, privacy, employee handbooks, EULA’s and such) and give their end users a way to easily see what’s changed before accepting it and track the history of acceptance. The stage is primed for a service like this to work and it’s something that would allow it’s creator to “do well by doing good.” It would drive better transparency in business practices, support consumer rights and promote better corporate responsibility.

If you build this and make a million, buy me a donut and follow me on Twitter.

Matt Asay wrote a post about a month ago and I’ve been meaning to respond. He argues that the comments section on blog posts tend to devolve into ghettos of expletives and personal attacks instead of productive discussion (I agree with this part of his post). He then proposes that Twitter is the medium we should be using to hold conversations around blog posts (this is the part I take issue with). Rather than describe at length why, here’s a graphic that summarizes the argument:

Examining what’s worked empirically

I believe commenting channels can be examined on the above seven dimensions. Admittedly there is zero science behind the above chart – this is purely subjective analysis via thinking about aspects of each medium and how they contribute to effective or ineffective discussion. In thinking about groups I’ve been involved with and which ones worked well the most interesting realization is that there’s a factor outside of the qualities of the channels themselves that trumps everything here: it’s the glue of interaction beyond the channel. The most meaningful discussions I’ve been a part of were in groups where we had in-person or real-time interaction punctuated by periods of asynchronous online exchanges. AZCFUG, CFUG manager list, Cambrian House, Refresh Phoenix, AZIPA – these are all groups that produced valuable insight and relationships, every one of them anchored by a good level of accountability through real-time interaction outside of the online channels.

When you strip everything away it’s not even the real-time aspect that’s critical though- it’s the accountability / reputation factor that ultimately drives quality discussion. When you know your words stick with you wherever you go, you behave differently. You show respect, humility, ensure what you’re typing actually adds unique value, etc. Remove this factor and you get the faceless, ghetto problem of Digg comments and the troll activity on our city’s newspaper site. You lose pride in ownership, start getting a few broken windows and the whole neighborhood adopts a license to behave badly. BUT… Twitter is not the antidote folks- starting a personal blog and supplementing it with Twitter is. Twitter alone is too short-form of a medium to communicate real substance and the “one-way follow” aspect makes it impossible to see the whole conversation as an outsider (unless people happen to be using explicit #hashtags). Yes, it addresses the accountability concern but it does so at the expense of introducing new issues of an “ADHD/Sound-byte-speak” and fragmented dialogue for the people involved. It’s like having UN delegates hold a debate where everyone can talk into their mic but nobody knows who’s hearing who because each set of headphones is tuned pickup a select fraction of the participants involved.

So what do you suggest?

The question becomes, “short of being able to have face-to-face interaction serve as an anchor of civility in discussion between online exchanges, what do you propose as the most effective means of holding productive debate online?” If you look at the above graphic you’ll understand why I believe the answer is to return to using the personal blog w/ a combination of verified comments for short responses and trackbacks for more substantive responses. Twitter has IMHO shoplifted people’s mojo and derailed this practice that used to be commonplace. I believe we’ll see Twitter fatigue and a resurgence of the way it used to be with volleys of blog posts that mutually link amongst one another. Facebook link shares and Tweets are pointers to content – like a fluid, more social RSS feed. But the real substance of discussion has always and will continue to reside in blogs.

My friend Josh suggested I submit this idea to Sunlight Labs to build. That seems like a noble effort they’ve got going but I figured it might be more interesting to instead do a blog post and cast it into the wild. So here’s a free business idea for someone who needs something to build:

Give me an easy way to compare what people said they would do with what they actually did.

Hindsight is 20/20 right? The first place to incubate this app is using government. Leverage the data.gov “open government” initiatives that aim to create more transparency through exposing raw data via API’s and offer a service that counters a real problem.

Problem description: Legislative officials get elected based on specific promises and then renege and vote the opposite way. They bury the issue, voters forget, they get re-elected indefinitely and the cycle continues endlessly.

Start with this very focused use case around this problem and build an app that lets me see the track record of how Senators and Congressmen voted vs. how they committed they would vote.

Question: How do you monetize this?
Answer: Build it as a platform with the logic abstracted but with the first iteration focused specifically on this government scenario. That’s your freebie giveaway. Make this available and free as a public service and have it serve as a marketing tool for the underlying platform which you’ll then sell to companies who want the same accountability/hindsight for their own internal decisions. This works for any scenario where there’s a record of expressed intent for a decision followed by the actual decision. Follow the lead of companies like Spigit and Inkling Markets who hosted public “fantasy league” prediction markets to create awareness and drive sales of their underlying platform.

All the data necessary to get this going exists publicly. You’ll have to get an intern to aggregate the unstructured historical info that’s scattered via newspaper articles and such on how politicians proclaimed they’d vote, but going forward much of this data should be available in structured format via the data.gov effort.

So my question at this point: “Is there anything remotely like this that already exists?” Sunlight Labs or Startup Weekend- what say ye? Could you guys knock out something along these lines? The domain is available.

Big thanks to Francine Hardaway, Phil Blackerby and Ed Nusbaum for inviting me to speak with their class on monday and share what we’ve learned on product development in our experience in building JumpBox. Fastrac is a great program sponsored by the Kauffman Foundation. I went through 2 semesters of this course a few years ago and it’s an honor to be invited back as a presenter. Note: realistically Kimbro is the visionary behind our product and he should be the one to give this talk, but I did my best to distill the 10 lessons I’ve gleaned around product dev while riding shotgun in building our our company/product offering. Here are the slides (feel free to share, embed, email, whatever):

We played the “product box” innovation game and had two teams invent and sell a new type of lawn mower in 10min. This is a great exercise to grok the difference between features, advantages & benefits. Here are the product boxes they came up with:

We had a little friendly “industrial espionage” given the proximity of the teams ;-) but good times. If you’re starting a company I definitely recommend looking for the fasttrac course in your area. It’s inexpensive and “gets you out of the building” and talking with other people who are in the same boat.

Oh and I try to share helpful info and links for entrepreneurs and software startups. If you use Twitter follow me for those tidbits.

Is this feasible to build? Bonus points if you can figure how to cancel out external music while letting me listen to my own.

You have a UI prototype and a pre-order for at least one at $300- someone please build it.
If nothing more consider doing it as a public service.

If you were tasked with re-architecting the typical high school experience with the end goal of “better equipping students for whatever they do next,” what changes would you make? Don’t confine your ideas to simple curriculum changes either, go nuts. Change anything about the full experience. Some aspects to consider:

• how are classes delivered?
• what is the best use of classroom time and what interaction can be conducted electronically?
• how are parents involved?
• how are grades determined?
• how are grades reported?
• is there another system besides standardized testing that will yield objective results?
• is striving for objective results even the real goal?
• how early is too early to fork the paths of college-prep hopefuls from others?
• what skills are timeless and is there a better approach than the current one for developing these?
• what’s the new interaction model look like in the classroom?
• if the agile manifesto were written from the perspective of teachers today, how would it read?
• what aspects of how classes are rendered is completely legacy and can be thrown out
• are there any fundamental sea changes occurring with skill development like shift from knowledge-retention as a goal to development of knowledge acquisition strategies?
• how do you amplify “street smarts,” social skills & intangible benefits?
• what can be entirely eliminated from the existing system?

Every time I hear the phrase “education reform” I cringe. Not because I don’t believe it needs reforming, but because the people throwing the phrase around are thinking in terms of “How can we boost standardized test scores? How can we graduate more students? What counseling programs can be introduced to reduce dropouts?” In other words, they’re thinking purely in terms of optimizations to the existing flawed system. The phrase “lipstick on a pig” comes to mind. These people unfortunately suffer from the same “curse of knowledge” that will guarantee their thinking remains constrained to the current paradigm.

Try this Innovation Games exercise: Try to imagine forward ten years. The kids that are currently in high school now will be a few years into the workforce (and possibly more if they skipped the college step). Hold an image of prosperity. Picture a scene of advanced living standards, a world successfully meeting challenges from all sides with our environment, urban development, natural resources, international relations, medical challenges, etc. Picture the younger people who are either responsible for these advancements or who are delivering the labor to render these developments. NOW…

Project yourself back ten years from this future point of prosperity and ask “What must the high school environment for these young adults had to have looked like for them to develop the qualities they possess today?” Note: this is a waaay different question than the typical “what should we change today about schools?”

I haven’t thought through all these suggestions entirely but here are some raw ideas that I’ve been thinking about:

Curriculum substitutions

Allow students to nix their current electives and choose from the following:

• basic accounting & finance: reconcile statements, concepts of interest, budgeting, investing
• speed reading
• typing
• practical web knowledge: effective search techniques, web fundamentals, intro web apps
• GTD methodology
• collaborative web applications 201
• negotiating
• persuasive writing
• public speaking
• sketching
• team collaboration
• scientific method
• critical reading
• logical fallacies
• entrepreneurship
• personal branding
• nutrition, health & wellness
• money management
• time management
• stress management
• basic auto maintenance
• minor home repairs: clothing fixes, appliance maintenance
• incentives & economics
• career safari

While these are typically thought of as college subjects I believe they’re core enough to merit pulling them down into the latter half of high school. The fact that things like money management, critical reasoning skills, basic auto maintenance and time management were never taught has always seemed like a major omission. And how obvious is it to have a course that exposes students to the breadth of careers available and plant early seeds which the student can investigate? While my high school experience was 90% quality, we had courses like Biology, Calculus and European history which I would have gladly traded in a heartbeat for any of the above.

Interaction model changes

To me it’s clear the interaction model needs to move away from the primarily unidirectional “hub and spoke” teacher-broadcasting-to-students approach. It needs to move towards a clustered student-to-student group mesh interaction with the teacher as facilitator. The immediate response is likely “wouldn’t this just be pure chaos with blind leading the blind?” The key is to think of this mesh spanning vertically across grades. Look to the interaction model of a martial arts dojo where experienced students must teach smaller groups of novice students in order to advance to their next belt. When you must learn something to the point at which you can teach it to others, it necessitates an entirely different level of understanding (not to mention it amplifies the power of your teaching force and the new “teachers” are much closer in demographic profile to their students and therefore better able to relate).

Course goal changes

The concept of courses as we know them today seems at best geared towards “imparting knowledge” and at worst “teaching to the test.” Perhaps the goal of school needs to be rethought more in terms of one’s “essence discovery,” cultivating raw talents, inspiring students to seek to develop these and most importantly, getting to a point of being excited to pursue whatever is next? We need to think of educating kids more like developing an athlete. I had this discussion with a good friend over lunch the other day: it seems like schooling for us mostly consisted of loading our mental computers up with software. The game now has changed and it’s more about developing our CPU/RAM capacity, installing a better OS and learning strategies for finding the software we need at runtime.

Grading model changes

To support the above goal, the concept of grades needs to be reassessed entirely. Given how the world works clinging to standardized testing is like if eBay were to discard its peer rating system in favor of a 100pt multiple-choice test administered to each buyer to determine buyer ratings. Sure, it’s a more standardized approach… but that’s all it is. It sacrifices meaningfulness for the preservation of “standards.” I don’t have a concrete proposal for what this new system should be but I know when something’s broken and standardized testing (especially the AIM’s test) is horrifically broken. We need to consider moving to a market-driven peer-review type grade system. Investigate marketplaces like Elance and “asymmetric follow” systems like Twitter to get ideas here.

Changes to Parent involvement

When I was in high school we had a parent teacher conference once a semester. One night. Likely the only interaction our folks would have with our teachers (unless we really f’d up in class that semester). With all the low-friction collaborative tech that’s available these days there has to be a way to channel more meaningful input to the parents and get more pro-active involvement out of them. Invested parents can compensate for a crappy teacher (I know this first hand) while it’s nearly impossible for the best teachers in the world to overcome a crappy parenting situation. And involved parents are better parents. Private microblogging platforms are what I’m envisioning here.

Getting Real

Cordon off at least 1/4 of the time for teaching skills in a Startup Weekend-esque way (ie. not explicitly but rather via pursuit of finishing a real project). Pick from non-profit endeavors or other public works projects and deliver some aspect as part of your class. Fieldtrips weren’t always about ditching the tedium of the classroom and goofing off, they were reminders of how what you were learning was applicable to real life. There’s a lot of room to move what’s currently being taught in classrooms into field exercises. The result is students that are more engaged and learning that gets more deeply encoded and anchored with real experience so it can be recalled later.

Anyways, this post is getting too long. I have a bunch of other ideas, but what do you think? What changes will have needed to have occurred for the workforce ten years from now to be flourishing?