Visiting the 2014 Venture for America Fellows

I’ve had the privilege of visiting with and speaking to the Venture for America fellows at their summer boot camp for each of the past two years, and was excited to be invited back again this year.  

Their boot camp takes place in Providence, which is about a 3+ hour train ride up from New York.  So, the ride up ends up being a nice forcing function for me to reflect on what I’ve learned over the past year.

I’ve had a lot going on in the past 12 months, so there was much to cram in.  And in fact I realized afterwards that there was a lot that I actually left out.  While I’ve written publicly why I launched Orbital Boot Camp, I haven’t talked specifically about why I started Orbital, itself.  Perhaps that is a future talk.

In any event, here’s a hackpad of notes to my talk.

And also, a summary of the talk, as tweeted by the 2014 VFA Fellows:

Phase 2 Complete

A month ago, we announced the Orbital Boot Camp, a 12-week program to help you launch your side project.

Thanks to many of you who helped get the word out, we got a great response over the two week application window. We ran interviews over one week, found that we were over-subscribed in terms of qualified candidates, and then spent the following week deliberating and figuring out the best way forward for everyone involved.

We ultimately decided to run two classes of about 12-14 students each. Given the candidate pool, we would’ve loved to have setup a third class, but we weren’t able to make that happen in time.

The process has been an interesting one. Because you’re not trying to pick winners, as investors and accelerators do, you get to define a different bar. After all, this is an educational program and the output is to share what you’ve learned rather than to show off what you’ve done.

We looked for three things:

  1. Are you capable of doing what you are setting out to do?
  2. Are you coachable?
  3. Will you be a positive influence on the cohort?

Most of the applicants we interviewed met this criteria, so to get to our final group, we had to ask a few questions of ourselves:

  1. Will we be able to help the applicant with their projects?
  2. Do we believe that the boot camp is the right thing for the student right now?

This got us from 52 teams down to the 24-25 teams (one is still pending) that will be joining us next week.

One last thought: at first, I looked at the short 2-week application window as a liability. But in retrospect, it ended up being a great filter. The type of person who can make a quick decision about throwing themselves into a brand new program is the kind of person who would make a great student for it.

You have to be willing to jump in, and so those who were willing to make a decision quickly ended up being a self-selecting group of motivated, qualified individuals.

Overall, we couldn’t be more excited. The range of students and projects is pretty awesome and we’ll introduce them next week along with the rest of the Orbital Boot Camp team.

For now, we’re heads down getting ready for the start of the program.

Thank you to everyone who applied and expressed an interest in the program. I’m sorry we weren’t able to accommodate more of you this time.

Thank you also to everyone who helped get the word out. In particular, Khoi Vinh for featuring me on his blog, Glenn Fleishman for having me on The New Disruptors, the awesome folks who tweeted and retweeted, and the many unnamed people who shared this with their secret underground mailing list (this is seriously a huge thing).

Phase 3 begins this Monday.

Why I Launched Orbital Boot Camp

There are a plenty of places to help you develop your startup idea or product, but not a lot of places to help you navigate the initial creative process when you are just getting off the ground.

That’s what Orbital Boot Camp is all about.

It’s a 12-week intensive course to help people launch their side projects, where the output is not a demo day, but a public talk on lessons learned. There’s no equity exchange. Students pay to be in the program or are covered by scholarships.

The program provides: a space to work, instructors and coaches who will help students navigate their respective uncertain paths, and a community of like-minded folks who are all in the same boat. It also runs on evenings and weekends, accommodating those with daytime responsibilities.

The proposed projects may end up being funded companies, open source projects, art experiments, or educational programs. They may or may not make money. They may not even live on after the program ends. All of these outcomes are completely valid.

I’ve learned a lot from my short time in venture capital, but there are a few themes that particularly stick out in the context of the Boot Camp:

  1. The creative process is hard enough as is. To place additional expectations on an idea before it’s born—for example, whether it will or won’t be a venture-funded business—is a distraction and puts the cart before the horse. How your idea eventually sustains itself is indeed an important design consideration, but all of that is secondary to the simple act of figuring out what it is you really have and whether it is really what you want.
  2. It’s important to respect and appreciate the irrational as much as the rational. I could talk for hours about this topic, from investment decisions to product design, but the crux of it is this: while we may have control over conditions, we have no control over outcomes. It’s important to leave space for things to emerge.
  3. There’s tremendous value to working out in the open. Enabling people to find you achieves the same result as a strategy where you instead set out to find them. By embracing this philosophy, we are implicitly freeing ourselves from our own unrealistic expectations of having to know all.

I’ve designed the boot camp with these considerations in mind. The focus is on the experience rather than the outcome. Success is based on learning rather than achievement. All of this requires that people are willing to engage with each other openly.

While my time at Union Square Ventures has informed the design of the boot camp, what inspires it comes from moonlighting for the past three years teaching Entrepreneurial Design in Liz Danzico’s program at SVA.

(I should note that Entrepreneurial Design itself was inspired by what Christina Cacioppo, the course co-creator and my former Union Square Ventures colleague, and I learned from working at the firm. Everything informs everything.)

The course was designed to help the students understand that in an age of networks, it has become increasingly possible for skilled individuals to realize their own creative ideas rather than solely that of others. The course is best known for challenging students to make $1,000 using the Internet. And that, they have, launching all sorts of projects that satisfied the constraints of the class while also finding a way to express themselves.

It’s been an incredible privilege to teach in the program, but it took me awhile to fully appreciate it.

After moving on from Union Square Ventures in early 2013, then teaching through the spring semester, I did a bit of traveling. In doing so, I shared stories of my students’ feats in countless public talks and private conversations.

As I did, I began to notice a pattern. I’d introduce the class, the focus, the $1,000 Project, and then I’d begin describing some of the students’ projects. About 2 or 3 projects in, the audience would noticeably shift. They would be intently listening, but you could tell that their mind was elsewhere. I could tell that for many, they were thinking: “Hey. I could do that, too.” Eventually we’d switch gears and start talking about their ideas for launching their own side projects.

The students’ work has clearly inspired others, and seeing the effect their narratives have had on others has in turn inspired me.

Many people have asked me why I’m doing this and what I get out of it. Externally, I imagine that my actions appear altruistic simply because the usual markers of a profit motive are absent.

But I look at it somewhat differently.

From a practical sense, the Boot Camp is an attempt at creating an economic engine for Orbital, my new workspace where I plan to collaborate with others on my own project ideas—kind of like a modern day guild. If the Boot Camp proves to be viable and sustainable, I’ll have greater freedom to pursue whatever interests me on my own terms.

On a personal level, I’ve reluctantly realized that I’ve learned a lot from teaching. It’s forced me to crystallize my views and defend my positions in a way that I hadn’t had to do previously. I think teaching is one of the best ways to continue to learn once you’ve left academia—or in my case, a particularly thoughtful investment firm. We tend to think about self-sufficiency solely in financial terms, however I think it’s just as important to always be learning.

The Boot Camp is also an intellectual experiment. What will emerge if you remove the expectations of a financing and focus solely on navigating the creative process? What happens when you start from a broader base of ideas, irrespective of their fundability, whether they are civic, social, creative, or commercial in nature? How does having a more diverse environment of creators, whether it’s by age, ethnicity, gender, affect how we look at things? What happens if you treat the ideation phase as an educational process vs. a competition?

There’s a cultural motivation, too. At a macro-level, we are amidst a transition from an industrialized world to a networked one, where the laws of physics are fundamentally different than what we grew up with.

Everything is changing—how we work, how we learn, how we sustain ourselves, how we organize. It is not certain that this change will lead to positive outcomes for everyone, but it is certain that change will happen.

In the face of such uncertainty, I think one way forward is to take an indirect approach. Rather than attempt to create direct solutions, could you instead help more individuals learn to create their own opportunities—whether they are businesses, community organizations, services, or simply fun creative projects?

And, could you construct the program such that the exhaust of this education fuels the creation of even more narratives of individuals learning to leverage networks (whether their projects succeed or fail) that are more broadly relevant to people outside of early adopters?

I’d love to see more educational opportunities like this that foster experiential learning in addition to the many great resources we have around instructional learning.

There are many great educational programs, like the MFA in Interaction Design at SVA, or upstarts like Austin Center for Design and the School For Poetic Computation (and many more) that do this today.

The Boot Camp follows in that ethos, and for all of the reasons mentioned above, I hope we’ll continue to see even more do so, too.

Glenn Fleishman was nice enough to invite me onto his podcast The New Disruptors to talk about Orbital and the upcoming boot camp, which is slated to launch in the coming weeks (.  We recorded this just a few days after applications closed, and talk about how I got started and why the boot camp is such a relevant project for me.

It’s a nice marker for me because the last podcast I was on was back in November 2013 (Joel Bush’s Capital), which took place when I was still figuring things out after leaving USV earlier in the year.

About a week after recording that podcast, the opportunity to take over the space presented itself, and I’ve been pretty heads down on developing Orbital ever since.

Phase 1 Complete

Orbital Boot Camp applications closed last Friday, and I’m really pleased to report that despite the short, two week application window, the caliber of applicants is quite strong.

Here’s the breakdown:

  • 62 people applied: filmmakers, writers, educators, designers, artists, technologists.
  • Exactly half of the applicants are women.
  • 60% identified as underrepresented in tech.
  • 68% require financial assistance in order to attend

and the projects:

  • 52 total projects: software, games, courses, services, magazines, podcasts, films, physical products, and much more.
  • 63% of the projects are about building technology, (i.e. software/hardware) vs. 37% that are more about leveraging existing technology and networks.
  • 44% are Commercially oriented projects
  • 41% are Educational, Civic, or Social in nature (note: projects can belong to multiple categories)

Overall, I’m incredibly thrilled to have a deep, diverse pool of qualified candidates working on interesting projects.

There is a clear need for the program, which is validating for me.

But what is also clear though is that many qualified candidates require financial assistance in order to attend.

My rough guess is that there are at least 20 additional students who would be fantastic to have in the program if we can find a way to fund them.

I’m kicking off the interview process this week to make sure the program is a good fit for the student, but I’ll be concurrently pursuing a number of funding ideas, too, in the hopes that we can close the financial gap.

While we do have a few scholarships committed, there’s a lot more I’d like to do here.

Here’s to Phase 2!

Orbital Boot Camp Update

Since we announced the Orbital Boot Camp last week the response has been really fantastic.

As of this morning, we’ve received 18 applications from 22 people (mostly individual applicants plus 4 teams of two).

  • 12 are proposing software-based projects (67%), 6 are proposing projects that leverage technology and networks (33%) (both are equally appropriate for the program).
  • 15 of the applicants are male (68%), 7 are female (32%). 
  • 16 have requested a scholarship (73%), 6 have not (27%). 

There’s a healthy mix of commercial, educational, civic, and just plain fun ideas which will enable us to pull together at least one good cohort of students, if not more.

Moreover, I’m just impressed by the overall quality of the application pool.

Based on conversations I had last week, I’ve updated the FAQ with a few new questions around qualificationsclass size, and scholarship opportunities.

For anyone else who’s on the fence, we’re hosting a final Q&A session this Thursday evening, 5/29 at 7pm. Come join us if you can:

One final note: we’re moving pretty quickly here. A week ago, the Boot Camp was but an idea. However, thanks to all of the early applicants, it’s clear there’s an actual need.

Our deadline to apply is Friday, May 30th at 11:59pm. If you or someone you love has an idea for a side project, please encourage them to apply.

Thanks to everyone for their help in getting the word out and for their thoughtful feedback on how to improve the process.  I’m looking forward to a fun summer!

Introducing Orbital and the Orbital Boot Camp

This past March, I took over the old Kickstarter office in the Lower East Side.  Since then, I’ve been primarily focused on cleaning it up, learning to become much more handy, and thinking of ways to use the space to fund the space.

The space is called Orbital, and my goal is to make it a space for people to to do awesome stuff.

It’s a somewhat vague mission, but as many of my former students will tell you I’m a big believer in the idea of leaving enough room for others to come in and make it their own.

To that end, I’m excited to open up applications for the Orbital Boot Camp, a 12-week program to help people launch their side projects.

I’m a big believer in the value of side projects.  And, I think the potential for people to realize their own ideas has never been greater than it is now.  But it’s not at all easy, and we could all use a little help to make that happen.

If you have an idea for something you’ve always wanted to launch, I’d encourage you to apply.

Applications are open until May 30th, with the program starting the week of June 16th. The program will run on nights and weekends in order to accommodate those with day jobs, and I’ll be teaching the class alongside other instructors and guest speakers from my network.

If you’d like to learn more, go here.

We’re also looking for more individuals who can help sponsor a student. If you’re able to help, email me at


Entrepreneurial Hurdles


For our penultimate class for the semester last week, we asked the students to pair off and perform root cause analysis on a failure they experienced this semester. They summarized the conversations they had with the rest of the class, and these were the themes that emerged:

1. Perfectionism - This is the most predictable problem for a group of design students to have, and it was a stumbling block for almost everyone around the room. The students struggled with the tension between the desire to control every detail and the messy reality of product releases, the gap between an idealized product vision and one that could be executed. Those working on things that were lifelong passions found it difficult to create a scoped down or crude prototype of something that could be important to their career, and others just wanted too much data before making a decision. The best way to manage these fears turned out to simply be deadlines, internally and externally enforced (and practice). One of the biggest parts of the class is just kicking projects out the door whether they’re ready or not, and learning how to build and iterate in public.

2. You’re Not Your Project - There’s some major overlap here with the first problem. Our students grappled with emotional obstacles like impostor syndrome, fear of public derision, facing criticism from strangers, and generally untangling their identities from their projects. 

3. Thinking Out Loud - Learning how to work (and stumble, and fail) in public is extraordinarily difficult. Some students found it very hard to express their half-formed ideas, or converse rather than broadcast to their target audiences. Others failed to reach out to people early on and entered a vicious cycle of not getting feedback. They also learned that getting attention online for your projects or writing required much more than simply putting out good content.

4. Prioritization - If perfectionism was the biggest mental block, this was the biggest logistical one. The very short timeline of the class forced students to do some very aggressive scoping, which is particularly tough in the presence of ambition and curiosity. Students not only had to prioritize within the class’ many demands, but also on a wider scale—with the rest of their schoolwork, and lives in general. As first-time entrepreneurs, some students struggled with threading and figuring out dependency chains as well.

5. Real-Life Research - Soliciting and processing feedback from research proved much harder in reality than in concept. Many students regretted not doing more initial research, or not incorporating research into their design processes more closely. Others had to learn the balance between trusting one’s own intuition, understanding the perspectives of strangers, and the hard truth that it’s impossible to please everyone.

Other less common (but equally interesting!) challenges included:

  • Learning how to collaborate
  • Learning how to make decisions by yourself
  • Understanding what you wanted to get out of the class at the start
  • Money changing the tone/implementation of an idea
  • The class’s own reputation as “the class where you make money” shaping ideas coming in (this is an interesting one for us to fix!)

None of these challenges are surprising to veteran project do-ers, but they really are best learned by living (and fighting and giving up and reiterating) through the process. It’s rare to have an opportunity to stumble across so many hurdles in so short a period of time—we hope it’ll be a memorable and valuable experience for many years to come!

In our Entrepreneurial Design class, the learning comes from doing.  Whether you succeed or fail (i.e. the outcome) is less important than whether you are consistently looking to understand why things are happening the way they are.

To help foster this mindset, we focused last week’s class on lightweight tactics the students can use to review their work: what went well, what didn’t go well, and why did certain efforts not work?  This week, which is our final class, we’re specifically asking them to share one thing that they learned in a short, 3 minute lightning talk.

The common thread to all of this is the practice of openly sharing.  There’s a lot to learn from the things we produce, but being part of a close-knit network affords a great opportunity to learn from others, too, so long as the individuals in the network trust each other.  Further, the degree of learning is directly related to the willingness of the participants to openly share what they’re going through.

As you can see from the post above, this group of students had no qualms about being open with their failures and sharing some very personal lessons, bumps, and bruises.  The class has clearly learned a lot this semester, and as an instructor I’m lucky to have had the opportunity to learn alongside them.

When Halu opened in 2008, it completely changed my neighborhood, The Richmond District, for me.

Aside from the awesome food, the restaurant is owned and run by just about the nicest family around.  Their warmth is something special and I always felt like I was a guest in their home.  To say their restaurant is beloved is an understatement.

So it’s with great sadness to learn that owner Shigemi Komiyama recently passed.  As you’d expect from someone who was a drummer, Shig was always laser focused at the restaurant.  But after hours and on off days you’d see him hanging out at my friends’ music gigs if he wasn’t playing himself.

If you’re in San Francisco, there’s a memorial service tomorrow, March 9th from 11am to 3pm at the San Francisco Culture Center (2450 17th St.).  Also, the restaurant remains open, so if you’re in the neighborhood, I’d encourage you to stop by.  To the Komiyama family, I offer my heartfelt condolences.

More from The Bold Italic and SF Gate.

Entropy and Advice

I’m heading to SF tomorrow to officiate a Valentine’s day wedding between two close friends who I introduced. This is the third introduction I’ve made that has resulted in marriage, so I’m feeling pretty good about being on a roll.

Truth be told, my introductions were not intended to be love connections. They were the result of good manners in pretty casual social situations more than anything else.

So, I look at these marriages more from a place of wonder than one of accomplishment or pride. (Two couples are about to have their first kid!)

It’s often more important to get all the right molecules in the room than it is to be able to determine everyone’s individual path. And then, it’s pretty great to see what emerges.

As my photography teacher used to say: we’re not the architects of an image, we’re the midwives. And so, because of that, if a really beautiful photograph emerges, it’s totally cool and non-egotistical to say “wow, that’s a beautiful photograph”, because it’s not something that was ever in our control in the first place.

We have control over some of the conditions and our actions, but not the outcome. And, the reason to take photographs in the first place is to go along for the ride to see what will emerge. That is where the beauty is.

So, with that in mind, I’d like to ask you all again for your help in soliciting some words of advice that I can pass along to the newlyweds.

If you have any words of wisdom that would fit in the form of a tweet (140 characters), tweet it to me @garychou or leave it in the comments below.

I’ll compile the results and share it with you all.

Announcing: The Product Sessions

Last June, my friend Walter Chen, CEO/co-founder of iDoneThis, invited me to visit him in Las Vegas. Walter had just taken an investment from Vegas Tech Fund and thought it’d be interesting for me to come speak to their portfolio companies.

I’m deeply interested in the work being done to revitalize local economies and communities across the country—it’s some of the hardest, but most important work one could be doing—so I was definitely up for a visit. 

But despite all that, I wasn’t particularly excited about the idea of doing a solo talk. It seemed like we could do something that would be more worthwhile for the portfolio companies.

So, I proposed the idea of reviving an event called The Product Sessions and bringing it to Vegas.

The Product Sessions are a one-day event where startups get quality one-on-one feedback from product & design advisors who themselves have been in the trenches. I used to run these for both the Union Square Ventures portfolio companies and other NYC startups, and part of me was also curious if the format could work elsewhere.

Walter immediately loved the idea and then went to work to make it happen, getting everyone involved in the process. To cover the cost of the event, the participating companies all pitched in with Vegas Tech Fund providing matching funds. Laura Berk and Andy White from VTF brought in The Downtown Project to house the advisors and Work in Progress to host the event.

Less than a month later, Chris Fahey (ex-ZocDoc), Jordan Kanarek (DuckDuckGo), Leland Rechis (Kickstarter), Mike Beltzner (Pinterest), Phoebe Espiritu (Techstars NYC), and I flew out to Vegas and ran the event, meeting with 10 companies.

Everyone had a blast.

For the companies, they valued the opportunity to engage with people from outside their local community. For the advisors, it was both an intellectual vacation and an opportunity to see first-hand the revitalization of the downtown area. For me, it was all of the above plus the fun in getting the band back together.

Given all that, it’s no surprise that we all wanted to do it again.

So, I took that as a cue to officially revive The Product Sessions in 2014, not as an event local to New York, but as a traveling series that visits emerging startup communities across the country, featuring a rotating group of product/design experts who I know and trust.

This past weekend, we kicked off the season by returning to downtown Las Vegas, thanks in large part to our hosts Sara Vainer of Work in Progress and Laura Berk and Shilpi Kumar of Vegas Tech Fund. 

Idan Cohen (co-founder Boxee), Jennifer Brook (ex-The New York Times), Kevin Cheng (Incredible Labs), Matthew Smith (, and Mike Mayes (Technicolor) joined me on the trip and we met with 9 local startups.

In February (this coming weekend), we will be visiting Detroit, thanks to Ted Serbinski, Sharon Shehib, and Leah Moss from Detroit Venture Partners. Joining me will be Charles Adler (Kickstarter), Jimena Almendares (Meetup), Leland Rechis (Kickstarter), Martin Eriksson (Covestor), Nick Barr (DrawQuest), and Phoebe Espiritu (Techstars NYC).

This will be my first trip to Detroit, and I’m excited to visit and meet everyone.

I’m starting to plan the rest of our 2014 schedule with March being our next available date. If you’re a startup, accelerator, space, or fund, and would like to bring us out to visit, here’s some more information on how the event works

If you’d like to sponsor an event (perhaps for a group of non-profits that are building digital products or a community of bootstrapped tech startups), I’d also love to talk. I believe that technology can and should be used for more than just high-growth tech startups and that the need for quality critique and feedback is just as (if not more) important there, too.  If you believe in that, too, let’s work together.

I’m also planning to open source the event altogether so that people can run their own Product Sessions locally. You can follow (and eventually fork) the GitHub repo here.

Just as it’s a myth that you need to be living in large technology hubs in order to create impactful work, it’s a myth that great works spring fully-formed from the minds of brilliant anointed geniuses.

I would espouse that the value of critical feedback is overlooked, and further, that it is through the repeated and deliberate practice of receiving and navigating feedback from our teammates, advisors, and the market itself, that we develop the intuition that enables us to make our own decisions

This is a surprisingly difficult thing to do, especially in a world of amplified, dogmatic rhetoric. 

So, if you or someone you love would like the practice, I hope you will invite us to come visit.  

I spent a week in Austin last month and it was both hectic and great.  

I caught up with old colleagues and friends and also gave a talk on what I’ve learned over the past few years, as well as what I’m thinking about doing next.

ICYMI, Scott Gerlach wrote a thought provoking blog post in response to my talk.  (Scott is a student at AC4D and along with his colleagues has done a lot of great work around health care records.)

I was also a guest on Joel Bush’s 5by5 podcast Capital, and we talked a bit about my background in tech, my time at USV and the Entrepreneurial Design class that I teach at SVA.  You can listen to an archive of it here.

Mad props to my homies Ryan and Andrea for hosting me during my stay.  

The trip was the most fun I’d had in a long time.  I’m very fortunate to have the friends that I do and I look forward to seeing you all again soon.

Austin: What I’m Working on Next

I’m heading to Austin for the week to visit some former colleagues and to meet the current class of students at the Austin Center for Design, where I’m an advisor.

While I’m in town, I thought it’d be fun to talk about some of the projects that I’m planning for 2014. So, I’m hosting a happy hour talk on Friday, December 13th from 5-7pm, appropriately titled “What I’m Working on Next”.

I’ll also share some stories and lessons from the past few years, so if you or someone you love is interested in startups + VC, the design of social systems, design education, or independent film/music, etc., I hope you’ll drop by and join us.  It’s going to be a lot of fun.

We’re almost half full already, and from the RSVPs it looks like there will be a lot of great people in the room.

I’ll also be hanging out with Joel Bush and The Regulars the morning of 13th at Mozart’s, so come on by anytime from 8am to 11am.

Some of you may know me from the hit song “To All The Ladies, From Gary Chou”, which my friend Goh Nakamura wrote for me. (The song also features the excellent Jane Lui who you may have seen on the YouTubes.)

You may have thought, “Wow, I wish I had a song like this.”  If so, now’s your chance to commission an original song from Goh via his Winter Song Commissions and Cover Album Kickstarter.

I think my song is clearly the best one, but if I had to pick some others that I like, this one done in the style of Van Halen as well as this lullaby my friend commissioned for her baby girl are awesome, too.

And, if you’re really really ready to rock, you can spring for the $500 reward, which will unlock me as lead vocalist for your track.  It’s expensive because we will need to autotune it.  Also, because it WILL TOTALLY ROCK.  GET SOME!