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There, Not There: Anonymity and Timebox Constraints as Catalysts for Innovation

Before SnapChat, we lived with the understanding that things we shared on the internet were permanent and potentially public. Somewhere, somehow, they lived on in someone’s photo stream or in a hamster-driven server farm where they were waiting to creep back up on us just as we were plotting our run for political office.

SnapChat’s self-destructing photos and videos have given us back some semblance of privacy and encrypted text message apps like Wickr have made it easier to share sensitive information with people we trust.

Where Google+ and Facebook are increasingly reliant on online identities being connected to our ‘real’ names (sometimes to the detriment of marginalized people who want a layer of discretion), the current breed of mobile-first social platforms based around a username or no name at all, have given us the freedom to make new distinctions between public, private, and so private that it’s very presence is fleeting.

When it works, the rise of anonymous sharing and ephemerality have been able to give us back the illusion of privacy and the gift of free expression. When it doesn’t, we see just how exposed we really are.

The effects of apps like Secret and Whisper can also be seen in the ripples through our real-time interactions. Recently, an anonymous post on Secret exposed accusations of sexism and launched an internal investigation inside one of the tech industry’s most respected startups.

Anonymous apps haven’t come without criticism. Venture capitalist, Marc Andreessen, and tech journalist, Paul Carr, have both questioned the ethics behind these apps.


The criticism is valid. Like any platform that allows user anonymity, these apps can be a breeding grounds for gossip and mean-spirited interactions.

But despite the potential for trolling, anonymity is extremely useful for sharing things that could get you fired or even cause you harm. There are still places in this world where a 16 year old queer teenager doesn’t have access to an LGBTQ community of their peers and can’t share their feelings without being safe from violence. There are still places in this world where a woman has no voice or her voice is limited by her gender. When whistleblowers fear for their personal and professional safety, virtual anonymity can be used to give them a place where they can make their voices heard without fear of retribution.

I believe that the risk is worth the gain. Let’s not forget that these are fairly new products. You have to allow Secret – still under 6 months old – the opportunity to find its level. Both Secret and Whisper have the power to be more impactful than they are today. Many products started out as something that felt trivial and less ambitious but grew into systems of great impact.

Products like SnapChat, Secret, and Whisper can push us beyond sexting and spilling industry tea. Their privacy and lack of permanence have the power to make us more honest, more creative, and more apt to use technology to safely express who we are in a very specific moment in time.


Pilot Projects as Time Constraints in the Physical World


San Francisco's Living Innovation Zone

Acoustic whispering dishes exhibit in San Francisco’s Living Innovation Zone

Technology makes it easy for things to disappear, but there is this idea that objects that inhabit public space have to be permanent. But eliminate the constraint of permanency, and how creative could you be?

San Francisco’s preexisting parklet permit and the newer Living Innovation Zone permit are two pieces of policy that create flexible frameworks that give people and organizations the opportunity to express themselves on city-owned space with projects of varying permanence.

The Living Innovation Zone (LIZ) project is an example of local government getting creative with public space. Created in partnership with the Mayor’s Office of Civic Innovation, Planning Department, Department of Public Works, Yerba Buena Community Benefits District, and the Exploratorium, the first Living Innovation Zone on Market Street at Yerba Buena Lane was launched as a pilot to activate city-owned property and highlight innovative technologies and creative projects.

Pilot projects in the physical world can provide us with smaller scale and short-term opportunities to iterate and improve on a project before scaling it to a wider audience. In the first LIZ, the Exploratorium worked with the City “to build an interactive educational experience on the city sidewalks that open people’s eyes and illuminate how the world works.” This first Living Innovation Zone was started with the expectation that it would be an installation that would change as time went on with new pieces that bring innovation to the street and create opportunities for interaction.

One unexpected byproduct of the first Living Innovation Zone is the serendipitous exchanges that happen. I’ve seen musicians giving impromptu street performances inside the boundaries of the LIZ and strangers who speak different languages talking to each other inside the whispering dishes.

Future Living Innovation Zones will take on the personality of the neighborhood and the partners who make it happen. A LIZ helmed by a water conservation nonprofit could display new methods of recycling waste water and better using our resources. A LIZ helmed by a technology company could showcase maker technology by 3-D printing in public space or heatmap the spread of Twitter messages across the world and identify real-time social movements.

Cities are stewards of public space, but they can become even better stewards by embracing iteration and creating frameworks that move bureaucracy out of the way and allow more people to gain value from our public spaces.

Pop-ups: Activating Temporary Space to Change the Urban Landscape

Even before the current revitalization of Mid-Market, retail and hospitality pop-up, A Temporary Offering (ATO), was an agent of change in a San Francisco neighborhood that was more known for its urban blight than its restaurants and bars.

This project from The Kor Group was one of the first to identify underutilized locations in the Mid-Market neighborhood and use short-term leases to inspire innovative use of space. The Kor Group acquired the Renoir Hotel with the intent to turn the run down hotel into a 4-star property. But before taking on the multi-million dollar remodel, the developers created a pop-up partnership with local entrepreneurs to activate the previously boarded up ground floor retail space.Through ATO, Kor embraced an investment model that eschewed the long leases preferred by most real estate developers for more temporary spaces that embraced agility and allowed entrepreneurs to experiment and iterate on themes.

The transitory nature of the space gave makers, chefs, and bartenders a time period during which they could experiment with new ideas and then take the concepts that work and roll them into their more permanent endeavors.

ATO’s presence in the Mid-Market neighborhood gave birth to a FoodLab helmed restaurant with a rotating lineup of chefs, a Southwestern themed bar from The Bon Vivants, and several experimental retail projects, including a youth culture driven high-end denim boutique.

A Temporary Offering - Holy Stitch

Youth denim pop-up Holy Stitch at A Temporary Offering

Although ATO has mostly disappeared from the area, their brand of temporary space activation contributed to urban revitalization in a challenging neighborhood with new permanent retail in the form of the aspirational – Huckleberry Bicycles – to the practical – a much-needed CVS drugstore.

Like venture capital, urban real estate development is known for long-term, big money investment and the resulting big money wins. Projects like A Temporary Offering show that there is a model for shorter term investments that work together with local government to identify areas of blight and bring about necessary revitalization.

These types of neighborhood revitalization projects might not warrant long-term investment but can piggyback on longer-term projects and create a short-term strategy that revitalizes urban areas.

How can you use constraints to drive innovation?

Embrace pilots and pop-ups. Projects that lack permanence are low barrier and low risk. Retail has embraced the pop-up shopping experience, but a pop-up can be anything – a temporary art installation, a weekend startup accelerator, a day-long experiment in urban prototyping.

These types of projects work because they lower the risk threshold. When you take away the constraint of permanence, you have the freedom to create something without the expectation that you have to do it forever. You can quickly learn from these short-term projects and roll those lessons into your more permanent projects.

Give yourself a finite time to create something new. If your usual product development cycle is 2 months, see what happens if you shave it down to 3 weeks. Could you write an entire book in a month? NaNoWriMo is an entire month dedicated to seeing if you can. When you put yourself on a tight timeline, you create a sense of urgency that keeps your project focused. That doesn’t mean that you work around the clock and try to cram in the same amount of output. It means that you work on making more efficient use of time and changing elements and eliminating pieces in order to make more creative choices.

Forcing yourself to ship quickly and often eliminates a lot of the navel-gazing and poor decision making (or non-decision making) that goes into creating something new.

Eliminate features. Feature elimination is the prettier, sexier, but more difficult to capture adversary of feature creep. It’s tempting to want to throw everything into a release, but having fewer elements yields much more elegant products.

Even features that seem necessary might not be less necessary than you think. What if you eliminated the need for names in your product? First eliminate the real name, then eliminate the username. This was a key part of Secret from the get-go, but other applications could be interestingly affected by small doses of anonymity.

Launch lots of little experiments. Some will be winners and some will be dogs, but launching lots of small things and iterating quickly makes constant improvement a part of your process. Experiments work best when you’re trying to prove out hypotheses. You need to constantly be in search of the ‘do-over’. You’ll learn from every experiment and be able to roll those learnings into the next experiment until those small proof points turn into a larger project.

Experiments also distribute the risk among many projects of smaller scale instead of betting it all on one grand idea and having it fail in some epic, career-ending implosion. If the experiment is low-cost and doesn’t require a lot of resources, it’s much easy to get executive buy-in as you prove your way forward.

Accepting constraints and even creating them can allow us to tap into a deeper creativity. I’m inspired by artist Phil Hansen who was diagnosed with a neurological disorder that made his hands shake. Instead of quitting art school and throwing his creative dreams aside, he made art that took his now permanent hand tremor and turned it into something special. How much more creative could we all be if we embraced the shake?


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How I Spent 2013 and Looking Forward to 2014

blog - Monique Woodard

Photo credit: Flickr
How I Spent 2013 and Looking Forward to 2014

Photo credit: Flickr Amodiovalerio Verde

Here’s to another year. My 2013 was one of the busiest and most fulfilling of my life and 2014 is already promising new opportunities and experiences. I always like to take a look back before diving head first into the new, so here’s a roundup of what happened and the one resolution I’ll make for 2014.

  • I went to TED (again) and saved my sanity (and my liver) by skipping SXSW. This year, I think I’ll do the opposite.
  • Despite not going to SXSW, I planned Black Founders’ Ideas Are Worthless Austin conference – the first minority tech conference to be held in conjunction with SXSW
  • Then I decided to take a mini-break from Black Founders so that I could spend this year as an Innovation Fellow for San Francisco Mayor’s Office of Civic Innovation
  • But I thought a lot about the state of black entrepreneurship and why it’s important not just for the black community, but for the economy.
  • I wrote a resolution on broadband and unlicensed spectrum which was adopted at the US Conference of Mayors.
  • I spent a lot of time looking at issues around access to internet in disadvantaged neighborhoods. I still think there’s incredible opportunity to use SMS to deliver services and information in these communities both here and abroad. This year, I would like to go to India and Africa to see the challenges of internet access up close.
  • I planned Innovation Month for the City of San Francisco.
  • I spoke at events, moderated panels, and judged hackathons.
  • And met more brilliant and interesting people than ever before.
  • I broke up.
  • I embraced the #NoNewFriends movement and got closer to my old friends.
  • Then I made some new friends.
  • I went camping.
  • I binge watched Breaking Bad, House of Cards, and Orange is the New Black.
  • I finally cut the cord.
  • I gave my time to causes I believe in like Compass Family Services (homeless families) and the All Stars Project (youth development).

This year, I make no resolutions save one:

Only do the things I absolutely want to do.

This is the direction in which I usually navigate, but I always find it useful to re-up on this resolution. Sometimes you get sucked into doing things and weeks or months (hopefully not years) down the road, you suddenly realize you’re not even interested in it. Life is too short and the stakes are too high to do anything less than what makes you a happier and more fulfilled person.

I’m excited to see what 2014 brings. I plan to keep doing big things, taking risks, and working only with people that I respect and who can push my intellectual horsepower to it’s limits.

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I’m Live Tweeting a Day in My Life for NPR’s Tell Me More #NPRBlacksinTech

blog, Diversity - Monique Woodard


NPR’s Tell Me More is again using social media to reach out to a new community of leaders — this time, to recognize black innovators in technology. African-Americans represent just 5 percent of America’s scientists and engineers, according to a 2010 study by the National Science Foundation.

Tell Me More is asking African-American entrepreneurs and techies to profile themselves for the upcoming social media series.

I’ll be live tweeting a day in my life on Tuesday, December 10 using the hashtag #NPRBlacksinTech.

Some of the questions I’ll be answering:

  • Accelerators: apply or not to apply?
  • Funding: VC or Angel?
  • Crowdfunding: Golden ticket or false positive?
  • Mentors: deficit or not accessible?

Feel free to jump in with questions of your own. I’m happy to answer just about anything.


#NPRBlacksinTech Week 2

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The Open Circles of Great Startup Communities

blog, Startup Advice - Monique Woodard

Innovation Month startup crawl at

People like Brad Feld have done a lot of writing on startup communities and what makes strong entrepreneurial ecosystems unique. Some of it is tangible — great engineering schools (Stanford), tech success stories (Google/Apple/Facebook), access to angel/venture capital (pick one) — but there are other factors that are much less obvious.

I’ve been to startup events in lots of different cities and when I’m in Silicon Valley, I notice something special that happens.

You’re standing in a circle at a party talking to a bunch of people, someone new approaches the edge of the circle, and we naturally opened up to let them join in. It doesn’t matter who the person is. They could be a software engineer, entrepreneur, or an accountant. It doesn’t matter if that person obviously has something they could give you or if you have absolutely nothing to gain from them. The circle always opens.

There are a few other entrepreneur communities that share this kind of openness. Boulder has it. Austin seems to have it.

I’ve been in other places where the circle didn’t open. I walked up to the edge and the circle stayed closed.

Every time it happens, I notice it and every time it doesn’t happen, I notice it too.

This kind of hyper-inclusiveness is one of the things that sets Silicon Valley apart from anywhere else. I write entrepreneur fan mail all the time and 90% of the time, those random emails to entrepreneurs I admire end up in coffee meetings, shared meals, and advice. That’s the power of Silicon Valley. It’s dumb easy to get smart people to talk to you.

Cities all over the world are working to build startup communities and thinking about how they can cultivate a vibrant startup culture in their region. Government initiatives and grassroots efforts have all converged to try to replicate what works in Silicon Valley.

Entrepreneur communities outside of Silicon Valley don’t need to mimic what’s happening here. You’ve got unique values of your own. But if there’s one thing you can learn from 50 years of Silicon Valley innovation cultivation, it is to make your circles as open as possible.

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