22 Lessons Learned in New York

After returning from a last minute trip to New York (for reasons I cannot share yet), I want to share 22 quick lessons I learned. Can you relate to any of them?

1. Why is Uber taking over New York? I couldn’t walk more than a block without finding a cab.
2. Someone as poised as a major news network anchor still needs cues from time to time
3. Warm weather always beats cold weather
4. Off-broadway performers are more coordinated than I will ever be
5. There is always a way to connect with someone
6. Flying into Laguardia is much easier than JFK
7. Always have google maps open while in a cab to monitor the trip
8. Don’t be afraid of the competition – try them on your head


9. Avoid connecting flights as best you can
10. 4am is a lot later than it seems
11. Starbucks wifi is optimized for customer turnover
12. Product demos always have a problem – bring a spare needle and thread in case
13. Land ownership in Burgundy is really confusing
14. Strong showers are critical to my happiness
15. You cross from friend to really good friend when you pick fuzz off his fleece
16. Always take pictures
17. McDonald’s chicken nuggets are good at any time of the day
18. If you want something ask for it, worst case they say no which is the same as not asking
19. When playing serious ping pong, make everyone use the same paddle
20. Dance floors are locked on Mondays
21. Drinking wine with a sommelier changes how you think about wine
22. Chicken wings in the bathroom make shower time delicious

Am I missing anything?

What Guyana Taught Me about Startups

I am a proud member of the Global Shapers, a program created by the World Economic Forum to empower millennials in cities all over the world to make a local impact.

Conversations with international Shapers are inspiring. They give me alternative perspective, both cultural and geographic, and I try my best to use their wisdom to improve my life.

For example, this is an unedited conversation I had with Onika Stellingburg, the curator from Georgetown, Guyana. We were talking about what it is I do for work. (Am I really this terse online? Anyone have a guide to proper Facebook chat etiquette?):

Onika: What does Clippo do?

I always knew it was there.

Neil: Make animated gifs and memes from your phone

Onika: Ps- I’M Slightly technologically slow but what’s IOS? Smart phones right?

Neil: yes iphones

Onika: I keep seeing this word ‘gifs’ ….it’s the moving pictures right?

Neil: yes, you got it

Onika: Excuse me….I don’t even own a smart phone so I pick regular things up slower than most. Yayyyyyy. There is hope for me yet.

Neil: much hope

Onika: So what do you do when you make them?

Neil: Share them with friends. It’s a way to communicate with gifs

Onika (at the same time as my previous message): Sell them online?


My creolese might come out here…..dats for fun or is it ya job?

Neil: love it, it’s my job and it’s fun

What I found interesting:

  1. She wasn’t sure what iOS was. I take having a smart phone for granted and iOS is a fairly common term, but this is not true for the majority of people outside the US.
  2. It was interesting that she knew what a gif was and not what iOS was, maybe the Buzzfeed effect?
  3. When she said smart phones, I said iPhones. Guess I’m not as quick to embrace Android.
  4. Her immediate question was whether we sell the gifs after we make them. At first I was amused, but then realized quickly that’s a very reasonable question. Businesses create products to ultimately generate revenue. The fact that we are focusing on growth and not revenue is probably amusing to her.
  5. I am a fan of Creolese.
  6. She asked whether Clippo is for fun or my job. I’m pretty happy to answer that it’s both.

Meaningful Conversation 3 – Seducing the Teller at Wells Fargo With Work

I am running a social experiment to have more meaningful conversations. This is a recap of one of my attempts. If you want to see why I am doing this, please read this: My Experiment to Have More Meaningful Conversations.

This was the first day that I approached someone that I did not know well to have a candid conversation. In fact, it was the first time that I actually interrupted someone’s life (and their job) to talk about mine. It was at the bank when I had to deposit some checks (I realize there are high-tech ways to do this, but I still take pleasure in depositing them myself).

I decided beforehand to talk to any random teller, whether I knew them or not. I did not expect to be nervous, but I was. I had the same feeling that I get in a bar before approaching a pretty girl. The name of this blog is ‘Shooters Shoot’ for a reason, so I just started with, “I’m excited to show you the new app we just released.” The teller was excited and so was the manager next to him. I showed them Clippo and they thought it was cool, but that was not enough alone to sustain a longer conversation.


The manager started to walk away, so I explained to the teller loudly enough so the manager could hear, how we were having trouble getting users and asked if he had any ideas. The teller said, “what about Facebook?” and then there was another 30-second silence. It would have been easy to give up there, but I kept pressing. I described how acquiring a mobile user on Facebook was quite expensive and it was only for larger companies like gaming companies with deep pockets who could buy users.

Thankfully, this brought the manager back (probably wondering what I was still doing there), with an idea. “You know,” he started, “one of my friends built this photo app that is one of the top 10 on the app store.”

Then the conversation started rolling. In fact, I ended up talking to them for almost fifteen minutes, completely monopolizing this teller’s time. What was even better was that he is an avid Vine user, so I was speaking to our target demographic.

Reflecting on this chat, I found two things interesting. First, I realized that there was a large barrier that I needed to surpass to even have this conversation; the teller needed tacit “approval” from his manager to talk to me. Second, once we started talking more personally about my problem, and not just the app itself, the teller began to think of more ideas, and became invested in the conversation. Maybe this is why as a startup we are supposed to “marry a problem” and not the solution?

Again like my first encounter, there was a fair amount of give and take. They offered ideas for my user acquisition problem and also asked some questions about startups, mobile apps, and other tech-related things they were curious about. Perhaps they didn’t have an outlet for this type of conversation or maybe they were just being polite and humoring me, but regardless I was happy to answer their questions. To be honest, I’m excited about taking my next trip to the bank- I am curious if our conversation has the potential to go deeper.

In addition to my commentary, I’m going to add a summary at the end of each post, so I can keep track of what the other person did, what they shared, and what I answered for them (if anything).

What they did:

  1. They both downloaded the app (2 new users!)
  2. The manager told me about his friend who made one of the 10 most popular photography apps in the app store – and one of his early user strategies (it’s a good one)
  3. One of them gave me feedback about the tutorial
  4. Both said they would try it and share with friends and will have feedback the next time I come in (I can’t wait)

What they asked me:

  1. What do you keep track of in a new app?
  2. How many users do you need to have?
  3. What was easier, building a product or finding investors? (I thought this was an interesting question – they didn’t ask about acquiring new users)

I Can Haz Title?

It took me a year and a few months but I feel like I’m finally breaking through with my writing and my blog. In fact it was the only resolution that I struggled with from last year. I wrote 2 posts last week and plan to have 2-3 this week.

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The best posts take about an hour to write and maybe another hour to edit (not counting the help of some awesome friends). What I did not count on is how difficult it is to come up with a title.

Good pictures are just as hard.

The title is SO IMPORTANT. For example, when I write a post, I share it on Facebook and Twitter. Someone then decides in a quick scan of their feed whether to read the post or not. All I get is 5-8 words to communicate with them WHY they should read it. Pressure, right?

The Upworthy approach (seen below) is fascinating but I don’t have the time or skill to produce 25 somewhat viable options. If I did this post would be unnecessary.

Screen shot 2014-02-12 at 2.03.06 PM
The slideshow where I took this from is pretty fantastic in terms of their viral process. Full link here.

I’m not trying to reach Upworthy levels of virality, but I would like to figure out a way to produce interesting titles that my friends would click on.

Any tips? How do you think of creative, shareable titles?

Meaningful Conversation 2 – Talking to Family About Your Startup

I am running a social experiment to have more meaningful conversations. This is a recap of one of my attempts. If you want to see why I am doing this, please read this: My Experiment to Have More Meaningful Conversations.

I am genuinely excited by my pseudo-experiment (I don’t think I can officially call it an experiment because I have no real hypothesis). After my first success, I was ready for attempt number two. As opposed to a semi-stranger, I decided to play it safe and try my sister.

This is such an effective chart.

I want to include family because, for me, it’s always been tough to talk about Clippo with them. It’s their job to be worried about my well-being and since startups are a never-ending series of volatile emotional swings, it’s easier to just talk about something else.

I feel like I can already hear my psychologist roommate saying this is the exactly WRONG way to handle your emotions. My naïve method was to just email positive press and give high level updates. I am not really sure how I ever thought this was a good idea. I started doing it a few years ago when we were bootstrapping the company and I was working out of my apartment and living with my co-founder. I was having a real issue separating work from the rest of my life.

I wouldn’t be surprised if this is common for those that work from home, since there is no physical separation between work and home life. I created a plan to have designated “work” times and designated “no work” times. Admittedly, this plan does not work very well–I am always thinking about what products we are building and how to make them better. However, in my mind, having some separation, even an imaginary one, has become very important to me.

My conversations with family members easily fall into the “no work” category because there are so many non-work things to talk about. But to be honest, I really just don’t want to worry about them worrying about me.

The goal is to remain one big happy family.

This time, when, my sister asked, “How is Clippo going?” I came clean. I told her we had just launched a major bug-squashing update to the app and that our largest problem was figuring out how to acquire new users and bring back our old users.

I think my sister skews my experiment results for two reasons: 1) she is family, so is going to go out of her way to help me, 2) she knows tech and marketing – she worked in the industry for about 8 years and is currently a rising star at a very successful start-up. I was not exactly asking a random stranger on the street for user acquisition advice.

She had some really great ideas. My favorite was the #getweird campaign. We were trying to brainstorm a hashtag that we could “own” and would spark people’s creativity to make funny and shocking memes. The idea is to have people make Clippos of the weirdest things they see on the street, at work, late at night, or at home. (In fact, I’m going to be running around San Francisco next week making funny memes in offices, on the streets, everywhere. If you are interested in helping out, please email me.) I would definitely count this as a positive outcome for experiment trial #2.

Going 2 for 2 so far has my confidence about as high as it can get. After sharing drafts of this post with a few people, they asked some interesting questions that I do not have the answer to yet. I thought the best way would be to share them below. Hopefully, I’ll be able to better answer these in future posts.

  • Are you worried how conversations like this impact your personal work/life balance?
  • Are you going to reach out to her more regularly?
  • Do you think these conversations will actually improve your relationship with her?

I think the next iteration for family is to talk to a non-tech knowledgeable family member and see if the result is as positive. I’m curious for anyone reading this – do you have problems talking to your family about your work?

Thanks to Vineeta Agarwala, Nick Meyer, Daniel Post, and Ritika Goyal for reading.

How Will Smith Helped Me Develop My Co-Founder Test

The number one question I get asked about startups is “How do I find a co-founder?” The short answer is that it is really, really tough. You need to find someone that you work well with, complements your skillset, shares similar values, and you get along with. At least that was my answer until I read this quote from Will Smith, and my new test is “can you see your potential co-founder saying this:”

Bonus points if said with cigar

“The only thing that I see that is distinctly different about me is I’m not afraid to die on a treadmill. I will not be outworked, period. You might have more talent than me, you might be smarter than me, you might be sexier than me, you might be all of those things–you got it on me in nine categories. But if we get on the treadmill together, there’s two things: You’re getting off first, or I’m going to die. It’s really that simple. . . .”

– Oscar-nominated actor and Grammy award-winning musician Will Smith

Continue reading “How Will Smith Helped Me Develop My Co-Founder Test”

My Experiment to Have More Meaningful Conversations


My typical day is filled with 3 kinds of conversations.

  1. 2-10 seconds. I like to call this a “freshmen dorm conversation.” I’m now five years removed from college so I’m not sure if I’m still allowed to make college analogies but here it goes: you see someone who you lived with in a freshman dorm and haven’t seen since. You say hello, and the conversation follows a set pattern: “Hey, how’s it going?” They reply “Good, how are you?” and you move on.
  2. 30 seconds – 3 minutes. This is someone who you see on a semi-regular basis and you start the conversation with general questions and maybe have time for a weather-related or current events topic. Then, you close up shop and move on.
  3. 3 minutes+. This does not seem like a lot of time, but how many of these types of conversations do you really have? To keep a conversation going longer than three minutes there has to be mutual interest and at least one meaningful topic of discussion.

I generally tend to have Type 2 conversations. This could be because I help run a startup and meet a lot of startup people; everyone I meet has his or her elevator pitch or talking points well rehearsed. In fact, I have a lot of conversations that are abridged versions of “the show,” which to me means anyone describing his or her startup with a positive spin.

I don’t know about you, but to me these Type 2 conversations are frustrating – especially when talking to interesting, intelligent people working on startups. It’s not really a secret that every startup is horribly broken anyways.

Entrepreneurs are eternal optimists, so I understand the impulse to use a positive word shield to hide what is really going on, but I wonder how helpful people would actually be if you let them try. For example, whenever we had office hours at Y Combinator, the partners would always ask what our most pressing problem was, and those sessions were incredibly productive.  This made me wonder, what if I did this with people who I see every day?

After having any idea, I run it by my “Am I crazy?” filter: my mom. She lives in a no B.S. world and is the perfect first person to run any idea by. Her response, “you are probably crazy. People don’t have time for your problems.” Since both of these are probably true, we created an important rule for a potential experiment. Don’t tell people my most personal problems, yet. Until I have a better idea whether this works or not, my shared problems will strictly be work related.

Like any supporter of the lean startup philosophy, before talking to anyone else or even writing this post, I decided to test this idea once. I’ve been going to the gym pretty regularly for the past two years and there is a guy who I see there a few times a week. We’ve probably had hundreds of Type 1 conversations and at least twenty Type 2 conversations. I still didn’t know his name or where he worked. He was a nice, anonymous gym guy.

This time, however, when he asked “How’s work?” instead of responding “Going great,” I replied that we had just launched our new app, Clippo, in the app store and were having a real problem with our user acquisition strategy. Namely, that paid apps and gaming companies had driven user acquisition costs so high that it made it very difficult for a consumer product without an extremely high budget to be competitive.

Gym guy didn’t respond with “that’s tough, good luck,” which is what I half-expected. In fact, he explained how the company that he works for created an optimized system for AdWords that would help us reduce costs and create a framework for user acquisition.

Some day I’ll have the lyrical flow of Eminem.

To quote Eminem, “Ah wait, no way, you’re kidding. He didn’t just say what I think he did, did he?” An insight and a strategy in my first Type 3 conversion experiment!

I made sure that I really understood what he had just explained to me. I asked at least five to ten follow-up questions, and gym guy answered each one patiently. I could tell he really enjoyed talking about his strategy and was excited to share it with someone who he knew was obviously grateful. How did I know that? I asked him.

I actually will be implementing his Adwords strategy over the next few weeks and, depending how it works for us (his company is in ed tech), will potentially write a post about it.

But my favorite part came after that – he told me one of his problems. For privacy sake, I won’t share what it was but am happy to report that I had a couple ways that I thought might help him. By approaching him with my problem, I think it made him comfortable enough to share something with me. Again, it is important to remember that before this we had never had a conversation for longer than 2 minutes. I wouldn’t say we are friends now, but I do know his name.

That exchange is what gives me real confidence that this can work. Another question my mom brought up was, “Is the average person going to know or care about your startup problems?” At first I had no answer, then I came back thinking “probably not and that is a good thing”. One thing we struggle with from time to time is uniformity of ideas. Christian and I work so well together and think so similarly that sometimes we are too close and too involved.

I’d love for some of my friends or anyone, maybe someone who works in finance or materials research, to tell me how they think I should acquire users. Maybe it will be awkward and they won’t care or have ideas, but maybe they will come up with something or some accessible group that I would have never considered. That to me is an exciting outcome.

This brings me to my plan: try and take one Type 2 conversation and move it to a Type 3 conversation every day. (My philosophy to stick to a plan is to take them one small step at a time.) Then, in every one of these conversations, I am going to lead with my most pressing work problem and write a post about how it went.

If the first couple weeks go well, I’m going to add personal problems to the mix. If it’s a disaster, I can always record them, make a reality show, and drive viewer growth using strategic Adwords placement. Someone asked me what my goal for this experiment is and honestly I don’t have something I’m trying to learn. I just want to see if it works for me. Am I missing something, how do you drive meaningful conversation in your life?

Big thanks to Nick Meyer, Melanie Major, and Sheila Vashee for editing.