Welcome back.

Have you thought about subscribing? It's free.

Alumni updates

Over the years, I've had the extraordinary privilege of working with an all-star cast of interns, students, co-conspirators and employees. One of the thrills of my career is watching each of them go off and make a ruckus, a generous one, in the communities they care about.

I got a note from one the other day, and I thought you might want to hear about what she's doing. That led me to asking about fifty of them for an update, and without further ado (click each ellipsis for more information):

Michelle Welsch crowdfunded money to establish an education center in Nepal that provides language classes, career counseling and weekly seminars.

Al Pittampalli is following up his last bestseller with a new one, Persuadable, that promises to change the way we think about leadership.

Alex Krupp is launching a social network that lets you share great emails with everyone.

Allan Young is the founder of Runway and TopLine, two of the largest technology startup incubators and communities for innovators in the San Francisco Bay Area.

Allison Myers and her team continue to fight Big Tobacco where they enter our communities, in the retail environment.

Amber Rae continues to spread creativity around the world, and give people a platform to share their voice through public art.

Andrew Chapman is refining his venture into cause-related publishing, now exploring the idea of incorporating an app into his business model.

Andy Levitt's vegan meal kit business, Purple Carrot, has now expanded across the country, helping people eat more plant-based food.

Barrett Brooks is working to build the best place on the web to learn to build an independent business you believe in.

Bestselling business author Michael Parrish DuDell just finished his second book for ABC's Shark Tank and is a recognized television pundit.

Bonnie Diczhazy is working on fun projects for Pack with fellow alumni Megan Casey.

Calvin Liu continues to grow and develop Outpour, an award-winning app for honoring the special people in our lives.

Casper ter Kuile is convening secular communities that are playing increasingly religious functions in people's lives like CrossFit and The Dinner Party

Chelsea Shukov makes beautiful things with paper, so beautiful that Target has asked her to make them available to a lot of people.

Clay Hebert continues to help entrepreneurs, creatives and ruckusmakers fund their dreams.

Corey Brown is Chief Instigator at Coreyweb, a small team offering expertise from 20 years of inventing, designing, building and improving successful websites.

Dahna Goldstein's company, PhilanTech, was acquired and she continues to work to help social sector organizations maximize their impact.

Evan Kirsch continues to expand the impresario philosophy by becoming a Partner at MAKE Digital Group, a technology consulting firm allowing him to focus his efforts on educational reform and implement indispensable leadership principles through the entire organization.  

Gil Hildebrand is leading a team of designers, developers, and marketers that supercharge some of the world's greatest brands.

Desiree Vargas Wrigley and GiveForward have helped keep thousands of people out of medical bankruptcy and put nearly $180M into the hands of American families when they need it the most.

Grant Spanier has been having conversations (on his podcast 10,000 HOURS) with some of the most interesting creative people in the world for two years now.

Rachel Simpson is continuing to work on Google Chrome – focusing on making important things easy and delightful to use.

Jeremy Wilson is continuing to connect his tribe and spread stories of inspiration through yoga classes he teaches in Chicago.

Jess Pillmore's living out loud with her revolution in sustainable artistry, provoking the arts and education to embrace play, ownership, and desiring the impossible.

Jessica Lawrence continues to build community through her leadership of NY Tech Meetup, a 47,000 member non-profit organization and the world's largest Meetup group.

Jonathan Van is continuing to help entrepreneurs build venture backed companies with great tools and investment.

Katrina Razavi has channeled her passion for communication skills and self-improvement into a blog that helps people improve their social confidence.

Kristina Villarini took her love for building community and amplifying voices to GLSEN, the leading national education nonprofit focused on keeping schools safe and affirming in grades K-12.

Leanne Hilgart's ethical fashion label VAUTE is one of the first private fashion brands to raise money from their biggest fans, with a goal to set a new standard of ethics in fashion.

Leslie Madsen-Brooks directs the IDEA Shop at Boise State, where she and her team help faculty use emerging technologies to develop novel learning experiences.

Liz Bohannon's ethical fashion company experienced record growth this year and continues to create opportunity for women and girls in East Africa. …

Matt Frazier built thriving vegan running groups around the world, connecting no-meat athletes in places as unlikely as Oklahoma City and as far away as Sydney, Australia.

Matt Radcliffe uses his multi-faceted talents to produce and support live performance art in Colorado Springs.

McKenzie Cerri and team continue to transform the way teachers communicate, inspire and support their students, by embedding coaching-cultures in schools.

Phoebe Espiritu is midway through 25×52.com, an initiative to launch 25 projects in 52 weeks. Among the projects is Project Moccasin, a mentorship program where applicants get to spend a day at work with a design, product or entrepreneurial mentor.

Mike Ambassador Bruny continues to work on making a difference at work with his latest podcast, No More Reasonable Doubt, geared towards young professionals of color.

Nicola Gammon continues to grow Shoot to transform the way we garden.

Noah Weiss is the SVP of Product Management at Foursquare, where he's helping build software that make cities more fun and easier to use.

Paul Jun is continuing his coaching for the altMBA, and inspired by the students' growth, he started a project in rebranding his platform (ships November 15th).

Rebecca Rodskog is enabling organizations to think about the future of work, be more innovative, and help them create environments where their employees can thrive.

Rebecca Shomair founded an art fundraising event that is now held across the US raising over a million dollars for the Anti-Defamation League.

Reggie Black contines to share his art in non-traditional spaces with people around the world, redefining how we interact with inspiration.

Sean O'Connor has launched a new edtech platform that makes tutoring more affordable and accessible.

Sharon Rowe is collaborating on #MagicAndMayhem: a speaking platform to inspire entrepreneurs, powered by women telling their real stories of launching multimillion dollar businesses.

Stefy Cohen is working in Latin America to promote entrepreneurship & innovation through her series of talks, courses, and events.

Susan Danziger launched Ziggeo, the leading recorded video technology, a powerful way to gather videos from applicants.

Willie Jackson is creating a space for black men (and women) to connect with opportunities, jobs, and each other. 

This is what it means to make a ruckus, to do work that matters and to ship your art. Wow.

Your progress report

I'm not sure we need to see a checklist of what you got done last week. What we really need:

a. the difficult questions that remain unanswered

b. the long-term goals where you don’t feel like progress is being made

c. risky, generous acts that worked

Even more important: All the things that aren't on your list, but could be.

Certain failure

Last night, a comedian tried out some new material, and someone in the front row didn't laugh.

Last week, I put up a post with a new idea in it, and thousands of people who read it didn't retweet or share it.

Last year, someone ran for office and didn't get every single vote cast.

Failure! Certain failure.

Of course your next project isn't going to delight everyone. That's impossible. It's certain that for some people, your project is going to be a failure.

At the same time, it's also quite unlikely that your project will please no one.

So now, we can agree that it's all on a spectrum, and that success and failure are merely localized generalizations.

Once you realize that failure is certain, it's a lot easier to focus on impact instead.

Advertising’s hidden design and its impact on our culture

Media changes everything. Media drives our expectations, our conversations and our culture.

And what drives the media? Ads.

Two kinds, it turns out: Brand ads and direct ads. Brand ads are the unmeasurable, widely seen ads you generally think of when you think of an ad. A billboard, a TV commercial, an imprinted mug. Direct ads, on the other hand, are action-oriented and measurable. Infomercials, mail order catalogs and many sorts of digital media are considered direct marketing. 

It takes guts to be a brand marketer.

What's the return on a $75,000 investment of a full-page ad in the New Yorker?

What's the yield on a three-million dollar Super Bowl commercial?

We have no idea. Brand marketers don't do math. They pay attention to the culture instead.

On the other hand, it takes math to be a direct marketer.

What's the yield on this classified ad? How many people used that discount code? How many clicks did we get?

The challenge of new media is this: Media companies can't figure out if they're selling brand ads or direct ads. And many who want to buy these ads can't decide either.

At the beginning of most sorts of media, it's the brand marketers who go first. The first to buy banner ads, or podcast ads or Facebook ads were brands with a budget to spend on new media that was esteemed by early adopters. MailChimp gets a huge benefit by sponsoring podcasts, but they can't measure those ads. And that's fine with them.

The next wave that hits new forms of media, almost always, is the seduction of the direct marketer. That's because direct marketers always have plenty of money to invest in ads that pay for themselves. The thing is, though, that direct marketers don't care about the medium, they care about the response. As a result, there's a huge gulf, a tension between what the medium wants (a great podcast, a website with authority, a social network with character) and what the direct marketer wants (measurable clicks).

Consider this: The best direct marketing advertising media is permission based. Ads where the ads are the point. Ads where the ads are not only measurable but the focus of the experience. Classified ads. Craigslist. Catalogs. The coupons in the Sunday paper. The Yellow Pages. Google AdWords. These are all forms of advertising we might miss if they were gone, and they are all forms of measurable direct marketing.

The best brand media, on the other hand, is media that informs and entertains despite the ads, not because of them. These podcasts, newscasts, blogs and magazines often run ads as their business model, but the ads don't drive the product, it's the other way around. 

The actionable steps:

a. If you're a media company that one day wants to be respected enough to attract brand marketers, refuse to maximize the clicks. The direct marketers will push you to develop the equivalent of classified ads, of Google Adwords–ads we want to see merely because they're ads. These are the most effective forms of direct marketing, because the people who look at them want to look at them. It's a form of Permission Marketing, and it works. But a short term focus on yield doesn't lead to a great podcast, and too many clickable popunders has been the demise of many a trusted website.

b. If you're considering buying ads, be super clear about what the ads are for. Just because you can measure clicks doesn't mean you should. It's that middle ground, the netherland between direct and brand, that leads to disappoint, both for you and the media company.

The challenge:

a. If you're a media company (particularly a website or a podcast, but possibly a conference or a magazine) and you're hungry for advertising, you'll soon end up hearing from direct marketers who want you to sacrifice your long-term standing with readers and attendees in order to make their clicks go up, who want more coupons redeemed and more short-term results. Try to remember that these advertisers aren't sponsors who care about your status or long-term prospects, they are direct marketers who will switch to a better yield the moment they can. That's the direct marketer's job.

b. If you're a direct marketer, your peers are going to push you to make ads that are more palatable to a brand marketer's sensibility. The problem with this, of course, is that you'll end up neither here nor there. You won't be culturally embraced the way an actual brand marketer can be, and you won't generate the yield you were looking for.

I've been a direct marketer for a long time, and it's entirely possible that I'll get kicked out of the hall of fame for saying this, but the fact is that the media that shapes our culture was not invented for or by direct marketers. 

Now that digital media is becoming a significant driver of our culture, I'm concerned that more and more media companies are hoping to get paid by direct marketers. That's never been a good match.

The simple way to get better at business writing

Don't do business writing.

Have you ever met someone in industry who talks like he writes? You visit a store and the person says, "effective January 1, 2015, we have ceased operations at this location. For further information, correspondence should be addressed to our headquarters." Of course not. That would be awkward.

Write like you talk instead.

"We closed this store last year. Sorry for the hassle, please call us if you have any questions."

With effort and practice, it's possible to speak with respect, precision and energy. After you speak that way, write down what you said. 

That's effective business writing.

Variations on stupid

We throw the word stupid around a lot, labeling people (perhaps forever). In fact, there are tons of ways to be stupid, and we ought to think about that before we shut someone (including ourselves) down… Stupid is something we do, not the way we are.

Bad analysis is the classic sort of stupid. This is not the stupid of, "if you knew then what you know now," but the simpler question: "Given what was clear at the time, why did you make such a bad decision?"

Willfully ignorant is the stupidity of not seeking out the information that would have been worth knowing before you spoke up, made a decision or pulled the trigger.

Lack of cultural understanding is often mistaken for stupid. This is what happens when we put our foot in our mouth. Often, it seems particularly stupid when we're willfully ignorant about something we should have known.

Inability to read people isn't a form of stupidity, but it can often look like it. Some people are just unable to do this, but mostly it's a lack of effort and empathy that leads us to not see people in a way others think we should.

Distracted is the best excuse for making a stupid call. After all, when the stupidity happens, it's probably because we didn't think the decision was important, and with all the incoming. Okay, it's not a good excuse, but it's a common one.

Self-destructive is a particularly widespread form of stupidity among people who have privilege and opportunity that they're not sure they deserve.

Emotionally overwrought stupidity happens because we're tempted to amplify and maintain the drama going on in our heads, which distracts us from seeing or processing what we see.

Fear, of course, is at the heart of a lot of our bad judgment. 

Unwilling to be right is a form of fear. If you do stupid things, you don't have to take advantage of the change that would have happened if you had been right.

Slow is not stupid, not at all. It's just not going to win you many prizes on a game show.

Short-term selfish behavior is what we see all the time from people who should know better. And yet they come back to this trap again and again, because it's a habit. Day trading, anyone?

Rush to judgment is a particularly challenging variation. Our unwillingness to sit with ambiguity causes us to decide before we should.

Stupidity doesn't have to be incurable.


So, which is more interesting: A vintage 1964 Porsche or a new Honda Civic?

Which is a better car?

If we think hard about the definition of 'better', it's pretty clear that on almost every measurable performance metric, the Honda is a far better car. More reliable. A better value. Able to drive faster, longer, in more conditions. Better mileage. Safer. And on and on.

So why do people pay more, talk more, gawk more at the other car?

Scarcity isn't the only reason. It turns out that perfection is sort of boring.

Airbnb isn't as 'perfect' as staying at the Hyatt (more variability, more ups and some downs) but it's certainly more interesting…

When a product or service benchmarks quality and can honestly say, "we're reliably boring," it might grow in sales, but it will eventually fade in interest, because the people at the edges, the people who care, are drawn to idiosyncrasy, to the unpredictable, the tweakable, the things that might not work.

Should we pander?

In a race to go faster, cheaper and wider, it's tempting to strip away elegance, ornamentation or subtlety. If you want to reach more people, aim for average.

The market, given a choice, often picks something that's short-term, shoddy, inane, obvious, cheap, a quick thrill. Given the choice, the market almost never votes for the building, the monument or the civic development it ends up being so proud of a generation later. Think about it: the best way to write an instant bestseller is to aim low.

The race to popular belies the fact that our beloved classics were yesterday's elitist/obscure follies.

Bob Dylan, Star Trek and the Twilight Zone vs. The Monkees, The Beverly Hillbillies and Gilligan's Island.

Zaha Hadid and Maya Lin vs. Robert Moses. 

A Confederacy of Dunces vs. Valley of the Dolls.

No one watches Ed Sullivan reruns (except for one, the exception that proves that rule).

It's our choice. The ones who create, the ones who instigate, the ones who respond to what's been built. It's up to us to raise the bar—pandering is a waste of what's possible.

Sometimes it seems like winner-take-all capitalism is pushing us ever harder to play it dumb. That makes it even more important that we resist.

Some people hate change

They don't hate you.

If you get confused about that, it's going to be difficult to make (needed, positive, important) change in the future.

Who is this for?

Is it for people who are interested, or those just driving by?

For the informed, intelligent, educated part of your audience? For those with an urgent need?

Is it designed to please the lowest common denominator?

If you're trying to delight the people who are standing on one foot, reading their email and about to buy from a competitor because he's cheaper than you, what compromises will you need to make? Are they worth it?