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?

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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.

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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”

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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.

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31 Things I Learned Traveling in Europe

I had not been to Europe in 13 years, crazy right? That’s why I was so thrilled to represent San Francisco at the Annual Curator’s Meeting of the Global Shapers of the World Economic Forum and then travel for a few days in Rome. While reflecting on my trip, I wanted to share 31 things I learned while in Europe.

  1. Talk to locals – they are like a real life Yelp
  2. Talk to drunk locals – its amazing how much you can learn about country politics, family and ambition
  3. If someone offers you a drink called the Bolivia, run away
  4. Made up handshakes are a great ice breaker
  5. If you want to go fast go alone, if you want to go far go together
  6. Get an unlimited use metro card
  7. Go sightseeing late at night (or at sunrise)
  8. Find restaurants with tables so close together that you can speak to the people next to you
  9. It’s hard to fit 2 people on a raft made of cardboard
  10. To hit a bullseye, take a breath and relax
  11. Always try starting a conversation with something other than English
  12. Things have a random way of working out
  13. Italians don’t like losing at foosball or ping pong
  14. With the right team, following can be just as satisfying as leading
  15. It’s amazing what you can get away with if you just answer “yes”
  16. Young people can truly change the world
  17. There are SO many problems outside Silicon Valley that are never even discussed here
  18. The best four flavors of gelato in no particular order are nocciola, banana, pistachio, and fig
  19. European airlines are so much better than US airlines
  20. Turning off your cell data plan is a liberating feeling
  21. International dance parties are the best kind
  22. Always wear sneakers at Frankfurt airport, especially when you have thirty minutes to make your connection
  23. An iPad is a must have for any long flight
  24. When in doubt take a picture, when you look back you never regret taking one
  25. Never go anywhere with a tour group
  26. Try not to go to a restaurant with a menu, and if it has one don’t order from it
  27. If you speak to 3 people in a row that speak English, go somewhere else
  28. AirBnb easily wins over any hotel
  29. Get on a random bus or metro without a map and go somewhere
  30. Gelato is a good idea at any time of the day
  31. Stay calm and Siyahamba

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New Year’s Resolutions Revisited

Now that it is the end of July, I want to revisit my New Year’s Resolutions to see how I’ve been doing. As opposed to a completely new post (especially for those who did not read my original resolutions) I thought it would be fun to annotate my old post. 

Resolution 1 

5 Year Vision: Keep learning new skills

3 Month Plan: Write at least one new blog post every 2 weeks 

Like a lot of people, I find writing something well takes lots of hard work. I survived English class because I spent countless hours proofreading and rewriting. When I wrote my first guest post for CBS Interactive a few years ago, I was terrified before submitting it. A post published on another site felt so permanent – was it good enough? I probably had 10 people proofread it and still had that roller-coaster-in-the-pit-of-your-stomach feeling when I submitted it. To become a better writer, I must make a concerted effort to practice.

My goal is to write at least one blog post every 2 weeks to develop my own voice and become more comfortable as a writer. My hope is that after a period of 3-6 months, blogging will become a habit and I can move on to developing another skill.

Anyone who looks at the dates of my posts knows I have not stuck to this schedule. I don’t think my lack of posts have been about a fear of writing, it’s honestly just difficult to think of many topics that are truly interesting to write about. I have fallen into a trap of writing for an audience vs. writing for myself, which I need to fight through. As anyone who runs a startup, I’m a sucker for page views and metrics. They drive my work life and I think that kind of thinking is affecting my writing. I know it sounds cheesy, but I really need to start writing for myself. This post is my first in that direction.

Though my posts have been less frequent, I can honestly say that my writing has improved as well as my confidence right before I press publish. In fact, I even wrote my second guest post, this time for VentureBeat: http://venturebeat.com/2013/05/29/how-to-make-a-viral-video/. Now, I just need to get back on a regular posting schedule, and I will.

Resolution 2 

5 Year Vision: Raise my emotional intelligence (EQ) [I think it’s funny that I put a link to this. Now I think I am actually beginning to understand what it means!]

3 Month Plan: Meet one new person (face-to-face) every week

I have now lived in the bay area for almost 9 years. Most of my friends from college still live in the area and I have a tendency to stay in my comfortable social circle. While having a strong support network is amazing, having one makes me less likely to meet new people. It’s time for a change, not only from a professional standpoint (where being able to connect with all types of people is really important) but also from a personal one. I’m not sure how I am going to find all these new people (if you want to meet me leave a comment), but we’ll leave that for another post. 

My goal is to meet someone new (face-to-face) every week and have at least a 15-minute conversation.

I’m happy to report that I have done a pretty good job with this and have met one new person almost every single week. I have gone out of my way to not only find new people, but also meet them after our initial contact. I cannot even begin to explain how much this has helped me both personally and professionally. Also as a personal win, I have never “grabbed coffee.” (I don’t drink coffee and am not a fan of coffee meetings in general. I feel like to get to know someone you have to share an experience with them, and coffee is never it.) The most difficult piece of this was figuring out where to meet new people. (If you are interested in how I do it, leave me a note in the comments and I’ll devote an entire post to it.)

Resolution 3 

5 Year Vision: Be healthier

3 Month Plan: Bring lunch to work 3 days a week

I already do a decent job of going to the gym, but my eating habits leave much to be desired. Startup life keeps me pretty busy, so I don’t have much time to cook for myself. This means that I eat out a lot, almost 10 – 12 times a week. That is pretty outrageous considering there are only 14 opportunities to eat lunch and dinner every week. No matter how often you go to the gym, you will never be able to accomplish any health related goals by eating fast food.

My goal is to make and bring lunch to work 3 times a week. I hope this first step leads to making dinner and improving my cooking skills as well.

Looking back, this is the resolution I am most proud of. It started with my modest three-month plan to bring lunch to work three times a week. This was relatively easy to accomplish and pretty quickly grew into cooking dinner as well. Now I am at a point where I bring lunch to work four times a week and also cook dinner at home FOUR times a week. The difference has been noticeable; I feel healthier and save a lot of money. I don’t suddenly have a lot of free time so if you are curious to know what I am eating or how I prepare it, please let me know and I’ll make it another post.

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My Favorite Cheap Food Places in the Peninsula

This is a bit different from what I usually write about, but I’ve had enough people ask me for food suggestions to do it. I have now lived in the Peninsula (which to me means Redwood City – Sunnyvale) for almost 9 years and being someone that loves food, I have tried most of the restaurants in the area. (Note: I may be missing some of the new restaurants, since I am cooking more thanks to my New Year’s Resolutions. So please share some of these in the comments too)!

For people that are visiting, new to the area, or those just curious, I want to share my list of the best cheap food places that are around here. Not just where to go, but what to order – which I think is something that restaurants hugely undervalue. If I go somewhere that is supposed to be great, but order the wrong thing, I’m not going to come back. (Note to restaurants: I’m a sucker for pictures in the menu so please help me out).

So here is the list in no particular order. To be included the restaurant has to be cheap (less than $12), have quality meat, and be delicious.

Sunny Bowl in Mountain View – Tuna sashimi (extra), brown rice (if you want to go healthy). Both the stone pot and normal bowl are fantastic, but if it’s your first time get the stone pot. Take a look. If you are afraid of uncooked fish get the beef (not the chicken).


Med Wraps in Palo Alto – Chicken shawerma plate (not the wrap). Get half baba ghanoush and half hummus if you want to be fancy. Usually they will also give you a free falafel (which is delicious).

Back-A-Yard in Menlo Park – White meat jerk chicken plate (you can go dark meat too, I just don’t like dealing with bones)

Muracci’s in Los Altos – Katsu Curry.

iDumpling in Redwood City – Pork, Shrimp and Chive and Chicken and Spinach Dumplings. (I just happened to be there yesterday so I took a picture. It’s not as pretty as it could be since I remembered to take it mid-meal)


Plutos in Palo Alto – Main salad (plus 7 toppings) with turkey (white meat). I know it’s a chain but it hits the spot every time.

If you haven’t been to these places, do yourself a favor and go. I’ll write one about SF soon too.

Did I miss anything? Please share your favorites in the comments so I can try them too.


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FB Login and What We Learned from our Show HN

Hello Hacker News,

2 weeks ago we put up a Show HN a few weeks ago titled: Show HN: It’s hard to make friends offline, so we built a solution (letsbeamigos.com). Though the post was relatively popular (97 points and 180+ comments), we made a few product mistakes that made our Show HN not as successful as it could have been:

{For those of you that don’t know: we are building a system to match people to those they don’t know, but share similar interests (whether it’s a sport they both play, a type of restaurant or a hobby). Then, we help coordinate an activity off-line. (Check it out: http://www.letsbeamigos.com)}


Problem 1. Using only Facebook sign up

(Note: We as a team still sit on the fence about this since we are building a social product.)

These were our assumptions about why only Facebook signup made sense:

  • It gave us a way to make sure people were “real.” After all, it would not be much fun to be set up on an activity with someone that did not exist. (This was only somewhat true as people have fake Facebook accounts for many reasons)
  • It gave us insights into the likes/ dislikes of people based on their Facebook information and also helps us with our matching algorithms (more on this below)
  • It was an easy way to sign up/ log in for a service without having to remember a password (we still think this is true, but this benefit is not exclusive to fb sign in)

Our decision definitely received some backlash and interesting HN comments, as well as Olark conversations, but FB-only-signup also gave us some product issues:

  • The email people used to sign up for Facebook was not one that they checked every day (which is especially important if that’s how you want to schedule events).
  • Facebook interests and likes are not good representations of what people like in real life. For example, I love basketball, technology startups and eating. But my likes on Facebook are: Counting Crows, Sky High Lab, Tapestries of Hope, and company pages of my friends. That’s not really a good representation of what I am off-line, is it?

Our solution is a trade-off: allow people to register with just their email and opt-in to using Facebook if they also want to share likes and interests. As a result we had to make our questionnaire longer. We are curious to see how this converts/ improves the quality of our experience.


Problem 2. “Enter your city”

The plan was always to launch only in the Bay Area – for any sort of localized service having region-specific knowledge is especially important. To do this, we asked each person that registered where they lived with a dropdown: San Francisco, Palo Alto, and “Enter your city.”

We initially wanted “Enter your city” to gauge interest of other cities that really wanted the service (to help our expansion strategy in the future). The problem that emerged, though, was that we had too much interest outside our area and could not provide them with the service they signed up for. Our fact-finding mission actually ended up preventing us from satisfying our users (not something we wanted to do!).

Our solution is to remove the “Enter your city” option entirely and just have San Francisco and Palo Alto as signup options. We will make sure the product kicks ass in our backyard and then expand to help the rest of you! We really appreciate your patience.


Problem 3. Feedback channels

When doing a Show HN, you are really asking the community to comment on something that you have built, and have them give feedback to make it a stronger product. We relied on the comments of the post to help, but it did not work. Most of the comments were related to FB login and not the actual reasons that people wanted / did not want a product like this, how they would use it, or how they would want it to work. We were all getting stuck in the trees without seeing the entire forest. (This post is the place to discuss the merits of FB signup!)

Our solution is to build that feedback channel into the product itself. After registering, we have revamped how we gather information.  On top of learning your likes/ dislikes we ask how you would like a product like ours to work and how we can improve. We have a clear vision of what we want to achieve, but always love hearing feedback from our users so we can make something they want.

Thanks for reading and I hope these lessons are helpful when you are doing your next Show HN or a private beta of your product. If you have any things to add or questions please leave a note in the comments. If you live in the Bay Area we would love to have you try: http://www.letsbeamigos.com.

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