Pleasure and Pain

Improving the human experience one day at a time

Pleasure and Pain: photos by Whitney G. Hess

A Brief Recap on Year 4

February 2nd, 2012 · No comments yet

2012 started off with a bang and my mind has been moving at a million miles a minute ever since. I managed to miss a few important milestones and never got around to taking the time to reflect on the year here. I suppose I decided that dwelling on the past (even if it yielded some benefit) shouldn’t take precedent over working on the future.

But I’m a fan of tying things up with a nice little bow on top…maybe I need it in order to fully move on. So I’ll keep it short.

January 7, 2012 marked my 4th anniversary on Twitter. Joining Twitter completely changed my life and it continues to have a huge impact on my work every day. Whatever you think about the new design or the lack of features on the apps, or whatever silly complaint you might have about it, this asymmetrical chat room we call Twitter is ultimately about one thing and one thing only: people. People connecting with people they would never have had access to, would never have been able to communicate with so fluidly, so frequently, and so intimately if Twitter had never existed. And for that I’m incredibly thankful. [On my 1 year anniversary on Twitter]

January 10, 2012 marked the 4th anniversary of this blog. Pleasure and Pain was born just 3 days later, when I realized that being constrained to 140 characters wouldn’t nearly be enough for me to fully express myself to the world. The blog was unnamed for a while, but the intention has been the same since day one: bringing empathy into design and business, and stopping at nothing to defend the needs of the people who use our products. It has been a wild ride and I can’t wait to see where things go next.

I published with a lot less frequency in 2011, largely due to a significant increase in my speaking engagements and some pretty intensely awesome client projects. But when I did make the time, I found myself writing about things that I was incredibly passionate about. Many of you share those same passions, and the posts started very interesting conversations throughout the community. I’m really proud of that, and encourage all of you to do the same. Write what you know, what you believe, share it far and wide. People will respond, people will connect, and you both will be changed.

Here are my most popular posts (based on comments and views) from 2011:

  1. You’re not a user experience designer if…
  2. I’m Not Cool
  3. Hubs and Connectors: Understanding Networks Through Data Visualization
  4. Why I detest the term “Lean UX”
  5. Design Principles: The Philosophy of UX
  6. The Neighborhood Business Experience
  7. Netflix Recommends: Art & Design Documentaries
  8. Nationwide Insurance demonstrates user research with NationPam
  9. FONC and the Impostor Syndrome
  10. Photo of the day: Negative Floors

Thank you for being a part of my experience. Thank you for making it so pleasurable and so unexpected and uplifting and really, truly wild. I’m really looking forward to connecting much more deeply in 2012. Now let’s get to it!

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The plain numbers about women in tech – The VCs

January 31st, 2012 · 30 comments so far

I’m not much for the “women in tech” stuff — preferring to prove equality rather than beg for it — but sometimes the gender imbalance in this industry is so damaging that it would be unethical for me to not call it out.

About a year ago, I wrote a blog post titled The Plain Numbers About Women in Tech, presenting the raw data to prove that the highest profile startups employ very few women, and moreover that the vast majority of women who do work for startups are in roles that involve selling the product, not making it.

Some people shared in my dismay. Some people offered up the names of startups that have a more gender-balanced staff. Some people simply defended the places they work saying, “We’ve tried!” or “Does it really matter?”

A year has passed, and in a future post I’ll go back through those companies and check to see if their ratios have changed. But there’s something deeper here that I’d like to explore first.

On Twitter the other day, I saw some investor friends congratulate a fellow VC on being promoted at his firm. I clicked through to the firm’s website and navigated over to their team page. I immediately noticed something — all men. So I checked out some other hotshot VC firms off the top of my head — all men, almost all of them. I’d always suspected it I guess, but here they all were staring back at me.

As a user experience strategist, I have spent the entirety of my career devising ways to get companies to better understand the needs of their target audiences. Building a culture of empathy within the business is my most fundamental goal, and the greatest obstacle I face is convincing upper management that their customers are nothing like them, that they have to think outside of themselves in order to succeed.

So here’s my question: if all-male venture capital firms are investing in all-male startups, where is the female influence coming from? Who is guiding these companies on when and how to target women? With women making 85% of purchasing decisions and far surpassing men in their Internet usage, doesn’t it seem wrong that hardly any women are involved in controlling which companies create our future?

I thought it was time to take an empirical look at the gender ratio of some popular venture capital firms by looking at their team pages, as I previously did with the startups. I limited my research to firms that have a focus in early-stage funding, have funded > 5 brand name startups, and have funds worth > $100 million. Again, this is by no means a comprehensive study, but this is what I found.

Take a look for yourself…and let me know what you see.

NOTE: I excluded female staff NOT in investment positions (e.g., accounting, legal, biz dev, operations, admin) from the counts below. Yes, I did this all by hand.

High Profile Early-Stage Venture Capital Firms

Accel Partners

Team Page: http://www.accel.com/people/index.php
Women Investors: 4/40
Fund Size: ~$6 Billion [source]
Portfolio: comScore, 99 Designs, Birchbox, Diapers.com, Etsy, Kayak, Trulia, Groupon, LearnVest
Location: Palo Alto, CA; New York, NY; London, UK; Beijing, China; Shanghai, China; Bangalore, India; New Delhi, India

Andreessen Horowitz

Team Page: http://a16z.com
Women Investors: 0/6
Fund Size: $1.5 Billion [source]
Portfolio: Airbnb, Fab, Facebook, Groupon, Pinterest, Zynga, Skype
Location: Menlo Park, CA

August Capital

Team Page: http://www.augustcap.com/team/
Women Investors: 0/8
Fund Size: ~$1.3 Billion [source]
Portfolio: Six Apart, Aardvark, Evite, RelayRides, Blippy, Visio, Livemocha
Location: Menlo Park, CA

Bain Capital Ventures

Team Page: http://www.baincapitalventures.com/your-team/
Women Investors: 1/31
Fund Size: ~$1.5 Billion [source]
Portfolio: Blip.tv, Jott Networks, Lala, Rent The Runway, Color
Location: Boston, MA; New York, NY; Palo Alto, CA

Benchmark Capital

Team Page: http://www.benchmark.com/people/#
Women Investors: 0/9
Fund Size: ~$3 Billion [source]
Portfolio: 1-800-Flowers, eBags, Dropbox, Zipcar, Instagram, Twitter
Location: Menlo Park, CA; Herzliya, Israel

Bessemer Venture Partners

Team Page: http://www.bvp.com/Team/
Women Investors: 1/39
Fund Size: ~$2 Billion [source]
Portfolio: Pinterest, Shopify, Knewton, Twilio, Diapers.com, Soap.com, LinkedIn
Location: Menlo Park, CA; Larchmont, NY; Cambridge, MA; Herzliya, Israel; Mumbai, India

Charles River Ventures

Team Page: http://www.crv.com/team
Women Investors: 0/10
Fund Size: ~$2.1 Billion [source]
Portfolio: Yammer, HubSpot, Scribd, Wanderfly, Zendesk, Geni, Twitter
Location: Cambridge, MA; Menlo Park, CA

DFJ Gotham

Team Page: http://dfjgotham.com/team.html
Women Investors: 1/5
Fund Size: ~$6 Billion [source]
Portfolio: ADstruc, Drop.io, Medialets, Mimeo, Solvate, Totsy, Yipit
Location: New York, NY

First Round Capital

Team Page: http://www.firstround.com/team/
Women Investors: 0/6
Fund Size: ~$126 Million [source]
Portfolio: Fab, Get Satisfaction, GroupMe, ModCloth, Path, Taskrabbit
Location: San Francisco, CA; New York, NY; Philadelphia, PA

Foundry Group

Team Page: http://www.foundrygroup.com/team/
Women Investors: 0/4
Fund Size: ~$225 Million [source]
Portfolio: Fitbit, CrowdTap, Makerbot Industries, Gist, Cheezburger, Zynga, Medialets
Location: Boulder, CO

General Catalyst Partners

Team Page: http://www.generalcatalyst.com/team
Women Investors: 1/19 (early-stage)
Fund Size: ~$500 Million [source]
Portfolio: Airbnb, GroupMe, Hunch, Kayak, Rue La La, Chloe + Isabel, Upromise
Location: Cambridge, MA; Palo Alto, CA

Google Ventures

Team Page: http://www.googleventures.com/team
Women Investors: 2/13
Fund Size: ~$200 Million (annually) [source]
Portfolio: HomeAway, Nest, Read It Later, 23AndMe, Signpost, ThinkNear, RelayRides
Location: Mountain View, CA; Cambridge, MA; Seattle, WA; New York, NY

Greycroft Partners

Team Page: http://www.greycroftpartners.com/team/
Women Investors: 2/6
Fund Size: ~$200 Million [source]
Portfolio: Buddy Media, Klout, Pulse, Joyent, Crowd Fusion, The Huffington Post, Babble
Location: New York, NY; Los Angeles, CA

Greylock Partners

Team Page: http://greylock.com/teams
Women Investors: 1/16
Fund Size: ~$2 Billion [source]
Portfolio: Airbnb, Constant Contact, Coupons.com, Facebook, Groupon, Pandora
Location: Menlo Park, CA; Cambridge, MA; London, UK; Beijing, China; Bangalore, India

Highland Capital Partners

Team Page: http://www.hcp.com/highland_team
Women Investors: 2/27
Fund Size: ~$3 Billion [source]
Portfolio: CafeMom, Gemvara, Digg, Pixable, Rent The Runway, Paper.li, Yipit
Location: Cambridge, MA; Menlo Park, CA; Geneva, Switzerland, London, UK; Shanghai, China

Khosla Ventures

Team Page: http://www.khoslaventures.com/khosla/people.html
Women Investors: 0/8
Fund Size: ~$1.05 Billion [source]
Portfolio: HowAboutWe, RockMelt, Xobni, Square, AppNexus, ZocDoc
Location: Menlo Park, CA

Kleiner Perkins Caufield & Byers

Team Page: http://kpcb.com/teams
Women Investors: 10/44
Fund Size: ~$900 Million (early-stage) [source]
Portfolio: Blue Nile, Zaarly, Flipboard, Groupon, Klout, Spotify, Path, Square, Nest
Location: Menlo Park, NY; Beijing, China; Shanghai, China

Matrix Partners

Team Page: http://www.matrixpartners.com/site/team_landing/
Women Investors: 0/9
Fund Size: ~$1.25 Billion [source]
Portfolio: Gilt Groupe, HubSpot, Care.com, Airvana, Apple (once upon a time)
Location: Palo Alto, CA; Cambridge, MA; New York, NY; Mumbai, India; Beijing, China; Shanghai, China

Polaris Venture Partners

Team Page: http://www.polarisventures.com/WhoWeAre/OurTeam.asp
Women Investors: 2/18
Fund Size: ~$3.5 Billion [source]
Portfolio: Automattic, Confluence, Formspring, JibJab, Turntable,
Location: Waltham, MA; Cambridge, MA; Palo Alto, CA; New York, NY; Dublin, Ireland

Rho Ventures

Team Page: http://kpcb.com/teams
Women Investors: 10/44
Fund Size: ~$510 Million [source]
Portfolio: Bluefly, GetGlue, OMGPOP, iVillage, Tapjoy, TACODA, Everyday Health
Location: New York, NY; Palo Alta, CA; Montreal, Cananda

RRE Ventures

Team Page: http://www.rre.com/#team
Women Investors: 0/8
Fund Size: ~$137 Million [source]
Portfolio: Betaworks, Bit.ly, HowAboutWe, Yipit, Xobni, Kik, GetGlue, Solvate
Location: New York, NY

Sequoia Capital

Team Page: http://www.sequoiacap.com/us/early
Women Investors: 10*/62 (early-stage) *all women are in the India and China locations
Fund Size: ~$1.3 Billion [source]
Portfolio: Airbnb, Funny or Die, Kayak, LinkedIn, Square, Eventbrite, Dropbox
Location: Menlo Park, CA; Herzliya, Israel; Beijing, China; Shanghai, China; Hong Kong, China; Bangalore, India; Mumbai, India; New Delhi, India

Spark Capital

Team Page: http://www.sparkcapital.com/team
Women Investors: 0/7
Fund Size: ~$720 Million [source]
Startups Funded: Twitter, Tumblr, Svpply, Runkeeper, Foursquare, Boxee
Location: Boston, MA

True Ventures

Team Page: http://www.trueventures.com/team/
Women Investors: 0/5
Fund Size: ~$378 Million [source]
Portfolio: 20×200, Automattic, Fitbit, Assistly, GoodReads, Plancast, About.me, Typekit
Location: Palo Alto, CA; San Francisco, CA; Falls, VA

Union Square Ventures

Team Page: http://www.usv.com/team/
Women Investors: 1/6
Fund Size: ~$450 Million [source]
Portfolio: Etsy, Boxee, Foursquare, Kickstarter, Meetup, Zynga
Location: New York, NY

Targeted to Women

A few female-led venture firms have cropped up with the mission to finance female-led startups, but they’re all managing funds well under $100 Million and are generally recognized as angel investors:

Golden Seeds

Team Page: http://www.goldenseeds.com/Funds/our_team
Women Investors: 8/10
Fund Size: ~$26.5 Million [source]
Portfolio: Lark, Little Passports, Sweet Riot, Tikatok, DRY Soda, Dancing Deer Baking Company
Location: New York, NY; Boston, MA; Philadelphia, PA; San Francisco, CA

Women’s Venture Capital Fund

Team Page: http://www.womensvcfund.com/about/team/
Women Investors: 3/3
Fund Size: Unknown
Portfolio: Ivy Corp
Location: Palo Alto, CA; Los Angeles, CA; Portland, OR

BELLE Capital

Team Page: http://www.bellevc.com/belle-angel-investor-team.html
Women Investors: 10/11
Fund Size: Unknown
Portfolio: Current Motor Company, Michelle’s Miracle
Location: Detroit, MI

JumpThru

Team Page: http://jumpthru.net/team/
Women Investors: 1/1
Fund Size: N/A
Portfolio: N/A
Location: New York, NY

Joanne Wilson

More info: O’Reilly Radar, The Next Web
Fund Size: N/A
Portfolio: Curbed (Eater/Racked), Food52, Red Stamp, Rick’s Picks, Hot Bread Kitchen, Gotham Gym, The Moon Group, Catchafire, Loverly, Daily Worth and MOUSE
Location: New York, NY

Bucking the trend

VC firms that aren’t specifically targeting female-run startups, but who have a predominance of female investors:

StarVest Partners

Team Page: http://www.starvestpartners.com/team/investment-team/
Women Investors: 5/6
Fund Size: ~$400 Million [source]
Portfolio: iCrossing, Insurance.com, ideeli, Bluestreak, Host Analytics
Location: New York, NY

DBL Investors

Team Page: http://www.dblinvestors.com/team.php
Women Investors: 5/8
Fund Size: ~$140 Million [source]
Portfolio: Tesla Motors, Pandora, Livescribe, Ecologic
Location: San Francisco, CA

Am I missing something?

So what do these numbers tell you? Have I forgotten about a VC firm with predominantly female investors? Am I unaware of some firms for-women-by-women?

Please set the record straight! Or share your thoughts on why we’re seeing this unsettling trend, and what we can do to make it right.

Further Reading

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“Design Principles: The Philosophy of UX” featured on Core77

January 26th, 2012 · No comments yet

Last Thursday I gave my talk Design Principles: The Philosophy of UX, at WebVisions at the Hudson Hotel in NYC. Christina Beard, a graphic designer and writer for Core77, was in the audience and wrote about my presentation in an article published yesterday.

Core 77

Christina later asked me if I believed my principles would change as technologies change and users adapt. I told her:

I feel confident that my principles for designing experiences will stand the test of time because they are technology agnostic. People deserve to be treated with humanity and empathy regardless of the communication medium. As the web evolves, as technology becomes even more pervasive and robust, we have both an increasing opportunity and responsibility to treat each other with compassion. I hope that my principles can continue to guide our behavior as technologists and ultimately change the way we do business at the most fundamental level.

Core77 is possibly the oldest-ever online magazine, started by two Pratt Students (my dad’s alma mater) for industrial designers, and has expanded to all facets of design over the years. It’s a very highly respected publication and I am honored to have my name in it.

I hope this helps designers of all stripes to think about the philosophy behind their work and approach their designs with principle and purpose.

[Read the full article]

Can you tell just how sick I was from the photo? Eesh!

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What I learned in 2011 and my predictions for 2012

December 19th, 2011 · 3 comments so far

It’s a funny thing — the more you share your opinions openly, the more people ask you for them. As the year is coming to a close, if you’re thinking about starting a blog next year or writing more frequently on the one you already have, don’t just make an empty resolution. STICK TO IT. I’ve been writing here for almost four years, and I am evidence of the fact that amazing things happen when you’re devoted to putting yourself out there.

Recently I was asked to contribute my thoughts to a few year-end articles, and have been quoted alongside many web practitioners who inspire me every day. You can read my excerpts here, but I encourage you to go to the full articles for a lot more wisdom:

A List Apart
A List Apart: What I Learned About the Web in 2011

CONTEXT IS KING
The most important thing that 2011 taught me about web design is that physical context of use can no longer be assumed by platform, only intentional context can. For the past couple of years, we have gotten into the habit of presuming that mobile means on-the-go, desktop denotes a desk, and tablet is on the toilet. But increasingly the lines are blurring on where devices are being used and how they’re being used in unison. This year I have learned to see devices as location agnostic and instead associate them with purpose—I want to check (mobile), I want to manage (desktop), I want to immerse (tablet). This shift away from objective context toward subjective context will reshape the way we design experiences across and between devices, to better support user goals and ultimately mimic analog tools woven into our physical spaces.

Webdesigner Depot
Webdesigner Depot: Web Design Predictions for 2012

The rallying cry of the web community in 2011 has seemed to be “make stuff.” My prediction for 2012 is that we’ll soon realize that that was rather shortsighted, and instead will encourage one another to “make stuff that matters.”

I have seen so much incredible talent squandered on designing products that only meet the needs of a small, homogenous, insular group of friends. While this can be fun and challenging for a side project, it is a fleeting satisfaction.

In 2012, mastery of the tools and a cool idea will no longer be enough to get attention. I predict that there will be a widespread movement to uncover and understand deep-seeded, life-damaging problems for sizable communities across the globe, and our efforts instead will be put towards improving their lives and work in ways that empower humanity. Productivity and entertainment tools have their place, but I suspect that we won’t continue to pat each other on the back so vigorously for continuing to crowd the market.

Design is the problem. The social, economic and political environments we will find ourselves in in 2012 will push us towards asking questions before devising solutions, equip us with a longer-term vision, and ultimately deepen our greater purpose.

The Next Web
The Next Web: The Future of Web Design

I hope we come to have a greater understanding of the various target audiences that our products have and that we deliver them content more intelligently. Right now, different content is appropriate on different platforms. But users tell us so much about themselves through their repeated use of our product and we haven’t done enough work to create customized content experiences for them as a result of all of that intel. Instead, we’ve only created custom, functional experiences but not custom, content experiences.

What did you learn about the web in 2011 and what do you predict we’ll see next year (or are just wishing will happen)? Please share your thoughts in the comments!

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My 2011 Holiday Gift Guide of Pleasurable Experiences

December 9th, 2011 · 1 comment so far

Stuff is cheap, in the long run. At the end of our days, we’re not likely to remember the things we acquired as much as the moments we experienced.

This holiday season, reconsider the packaged goods you’re intending to buy for the people you love. Instead, design an experience for them they’ll never forget.

oysters and champagne

Here’s my take on a holiday gift guide for that special someone on your list:

  1. Push the couches together and make a love nest that you both climb into. Put food on a tray between you, find a romantic movie on Netflix, and fall asleep in each other’s arms.
  2. Cook a meal together using only ingredients you bought that day from the farmers’ market. Make something you’ve never made before. Do the work together, then enjoy the fruits of your labor together. Leave the dishes for tomorrow.
  3. Take a drive in the rain. Bring sandwiches. Park in an empty parking lot and turn off the windshield wipers. Turn the radio off and then your cell phones. Share your lunch and your secrets.
  4. Build furniture. Lay out the materials, gather the appropriate tools, and take turns reading the instructions. Divide and conquer. Question each other’s accuracy. Laugh when you get it wrong. Enjoy starting over because it means you’ll have more time working on something together.
  5. Play startup entrepreneur and design an app together. Bring paper, pencils and sticky notes. Start with a problem you both always face, then sketch your way out of it. Encourage each other’s crazy ideas and explore new territory. Bonus points if you build a prototype. Figure out a business model and mock-pitch it to your friends.
  6. Be their career coach for the day. Act professionally, greeting each other with a handshake. Find out what they really want to be doing and what they feel is missing. Listen closely. Ask the tough questions and offer thoughtful solutions. Brainstorm new directions and ways to get there. Write down next steps. Plan to meet again.
  7. Go to a dimly lit local jazz club with people you’ve never heard of playing soothing melodies. Wear blazers. Drink whiskey. Put on your introspective faces and sway with the music. Snap your fingers at the end of each song. Make fun of the people sitting next to you who are clearly on an uncomfortable date in the quietest voice you can muster. Buy the musicians a drink when their set ends.
  8. Find an underground supper club. Be the last to arrive so everyone is already mingling. Make conversation with the host. Sit across from strangers. Talk about things you’d never talk about with people you know. Pay attention to the description of each dish and savor every bite, trying to taste each ingredient. Compliment the chef. Ask a ton of questions. Stick around until they kick you out.
  9. Go someplace you can really see the stars. Stare up at the sky together and marvel at all its wonder. Guess the constellations. Make up names for ones you don’t know. Talk about life on other planets. Wander through the galaxy in your minds and promise to experience space travel in your lifetime.
  10. Get up from the dinner table and dance in the living room. Pause the passing of time and hold each other close. Half listen to the lyrics and half feel the music and wholly move in unison. Smile wide. Imagine what the other is thinking. Don’t talk. Lean back and let the other hold you up. Pretend the song will never end.

Eliminate the baggage and make your future. Save your money and save each other. From me to you, happy holidays.

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