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Advice From an Early Startup Employee

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Just a short 14 months ago, I was faced with a decision of joining a startup as the first employee. Having worked at a slightly bigger startup, I have had some experience with working in small teams. But the decision of joining a team of 2 people is still a tough one. It was a leap of faith, facilitated by some gentle persuasion by Jordan and Doug. Late last week, we announced that Hyperpublic is acquired by Groupon. I can’t say I knew this was going to happen 14 months ago, but I know that I’ve made the right decision. If you are in a similar situation, I hope this post will help you rationalize your decision making process.

People join startups for different reasons, but almost everyone does it partially for the upside of making lots of money through the equity plans. This is probably the biggest myth for startup employees. The chance of your startup turning into Google or Facebook is practically zero. So the first question you should ask is:

Why should I join a startup if it’s not for the money?

This means completely rule out the money factor, and this is where people’s opinions diverge. For some people it’s the thrill of building something from the ground up, for some people it’s the prospect of taking on a wide range of responsibilities. Whatever it is for you, this is not a matter to be taken lightly. Here are some questions I see people often have and my thoughts about them:

Q: I want to get in early so when this company goes big I’ll be on top. Should I join a startup?
A: If this is your main motivation, it’ll be a long and treacherous process for you. The benefit is far out-weighted by the risk here, you’d have to be a really irrational person to do it. I find the carrot is usually not enough incentive to carry people over the hump. You will be exposed the ugly truths as the company figures out a path to survival, and it’s sometimes soul-crushingly painful. At times you will feel like you’ve just wasted the last 6 month, year, 2 years making something that is doomed to fail, and your friends who work at the big-co next door is making 150k salary while cruising through life. And you will get discouraged. But unlike the founders, you are not nearly as invested in the mission, so you will quit.

Q: I’m not sure about the founders, but I love the mission of this startup. Should I join?
A: From my experience, the is almost a sure death. As proven by history time and time again, ideas aren’t worth much. Ten years ago, people use to value ideas alot more, partially because the startup culture back then was less open. But today startups have become more agile, and the startup landscape is changing more rapidly than ever. Don’t join someone you can’t completely respect.

Q: I don’t know a lot about this industry, but I’m super impressed by the founders. Should I join?
A: Opposite of the last one, and much more promising. Sometimes it’s difficult to evaluate the quality of an idea, especially if you haven’t been working in that industry for more than a few years. Valuable companies are the ones able to adapt and execute, which makes the original idea less valuable. This puts more emphasis on the founders. How do you evaluate a founder? A great track record helps, but not having it doesn’t mean they cannot succeed. They have to be intelligent, genuine, and most importantly, super resourceful. If you find someone who check off all of these marks, I’d say go for it. Good founders have the tendency of getting stuff done come hell or high water. Even if the startup ends up failing, having worked with great people leads you to other great opportunities.

Q: I’m ready to move on, but my team now needs me. Plus, my boss would kill me if I leave.
A: We’ve all been there. You don’t want to let your teammates down by leaving. But this is a 2-way street. This is what happens if current job is not doing it for you and you try to be a “nice guy” by staying: you still don’t enjoy working there, your current work will go as it’s always been, and the startup will suffer. No one really wins in this situation. Give your 2-weeks notice, be respectful, and move on.

Q: I feel like I’ve worked in the corporate environment, it’s time to move onto a new challenge with more responsibilities. Should I join?
Q: I want to start my own company some day, so I’m here to learn. Should I join?
A: These are what I consider “the right reasons” to join a startup. To me, startup is a lifestyle. It’s really exciting at times, pretty fun and interesting most of the time, and really stressful and devastating occasionally. What carries you through the tough times is your personal resilience, passion and curiosity. You will get the opportunity of doing a little bit of everything, taking something by the horn and running with it. You get rewarded for taking risks and learn from making mistakes. The right attitude here takes you a long way.

Q: I can always go work at another startup if this one doesn’t work out right?
A: True. But you want to be careful here. Think of joining a startup as a 2-3 year career investment. How many 2-3 year chunks do you have? How many are you willing to invest?

Here are some day-to-day stuff to think about:

Q: I hear startup people work crazy hours.
A: That’s true somewhere. But if a company is well-ran, you shouldn’t be working more than 65 hrs a week on average. I’d say I worked a 60 hr week on average at Hyperpublic.

Q: I’ve made a lot of friends at my old job. Will I do the same at a startup?
A: It really depends on the company. Some companies are really social and some keep it professional. If you really like a social work environment, you’ve gotta make sure they have that.

Q: I hear you meet a lot of cool people (outside of your own company) by working at a startup. Is that true?
A: It’s true, but it doesn’t come for free. There are plenty of “networking” events, going to all of them can suck up a lot of time. You don’t want to talk to the people who are JUST NETWORKING. My advice is to pick events hosted by good startups, and pick the ones that will teach you something. Getting out of a conversation politely is a good skill to learn. Remember to always be respectful.

Q: I’m a PHD in (Machine Learning | NLP | PL | Cryptography| etc…), what’s it gonna be like for me at a startup?
A: Pretty different than your academic research life for sure. I don’t have a PHD but I’ve done a few years of academic research and have worked with many PHDs both in research settings and startup settings. Sometimes you are gonna have to write that simple CRUD app or that piece of front-end javascript just because everyone else is busy and the company really needs it. But you’ll also have a lot more control in the work you do, and that’s utilizing science in a truly practical manner.

Q: What’s the most exciting part about joining a startup?
A: I can only speak from my own experience. The most exciting thing is that I’ve grown so much faster in the past 14 months. I find myself becoming more resourceful. I have more ideas when it comes to getting stuff done, and I learned it through getting stuff done everyday in the last 14 months.

Q: What’s the suckiest part about joining a startup?
A: As a startup, there is no room for HR mistakes. That’s why when there is a misfit, you have to execute quickly. This is not personal, and it’s not even a statement on the person’s ability. It’s simply a “misfit”. But it still sucks to see people who have become your close friends being let go.

Q: Just how much WILL I make if all goes well?
A: Let’s just do a back-of-the-envelope calculation: let’s say you get 3% of the company (This is completely arbitrary. See PG’s essay for an idea on how much you should ask for). After a few rounds of funding (and most likely 2-3 years), you will be diluted to less than 2%. This means if your company gets sold at 100million, you will make less than 2million. Think about how many companies you know that’s sold for 100million, then think about how many launch announcements you hear per week. I think you get the picture. Also see here and here

Q: I’ve considered everything. Still not sure about this.
A: Try joining on trial basis. This is a great idea for both the startup and the employee if executed correctly. If you decide to do this, do some research about the startup and make sure they don’t have a bad track record of trying to get “cheap” work out of people this way. Do it on a project-basis and set the terms for both cases (hire or no hire) before you start.


Each of these points can be its own blog post, and I might pick specific topics to go into depth in the future. Good luck with this decision. It can be the best thing you’ll ever do for your career.

Brainstorming vs. Casual Conversations

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Brainstorming is an integral part of the creative process, and it’s especially true for software/product design.

The New Yorker published a great article this week titled “Group Think: The Brainstorming Myth”. The article tries to prove that “brainstorming” is not as efficient as “casual conversations”, mainly because it discourages criticism. Also see the linkbate on Hacker News “Brainstorming Doesn’t Really Work”.

The author makes great points about some downsides of brainstorming, backing it up with experiments and data. For example, the 2003 UC Berkeley experiment suggests that, groups who arrive to results through a “debate” process is often more productive than groups who use a “brainstorm” process, even though at times debating is unpleasant. On a slightly tangential topic, the author also brings up the point that “unfamiliarity” can increase productivity. (Backed by the Broadway production experiment conducted by Brian Uzzi at Northwestern) The article goes through many successful examples of modern work space setups that encourage casual conversations between multiple disciplines.

I totally disagree with what the linkbate suggests. (Although the article itself is quite interesting) Brainstorming and casual conversation have very different roles in the creative process. The points presented in the article are all valid, but the comparison is inappropriate. In a modern-day work environment, we need both.

Brainstorming is an organized activity. While it’s difficult to administor (therefore most brainstorming sessions are pretty poorly ran), it’s quite effective if implemented right. Here is why:

  • It gets all the shitty ideas out of your system. Everyone has them, it doesn’t matter how smart/creative you are. Getting all the shitty ideas out of your head frees more mental space for you to focus on the good ones.
  • It’s highly collaborative. It’s difficult to have a 5-way casual conversation. But having 5 different perspectives is super valuable. Sometimes 1 small idea changes the whole game.
  • Most brainstorming sessions involve Whiteboards. This is good. Laying things out visually can again, free up more energy to focus on the hard problems.
  • Breath-first vs. depth-first. For those who are not familiar with graph theory, BFS means exploring all of the adjacent points first, and DFS means go as deep as possible on one idea before exploring other ideas. Brainstorming tends to be on the BFS side, and that’s important especially at the early stage of a product.

I’m personally a huge fan of casual conversations. It’s a pressure-free and natural way to refine ideas and solve problems from other angles. These mini sessions can be extremely productive, but it’s kind of a hit-or-miss. To maximize the probablility of productive casual conversations here at Hyperpublic, we essentially sit in one big circle with the snack table in the center. Some of our best work come from casual conversations. Coffee trips is another good source of interesting discussions. When you are solving a technical problem, being able to talk to someone else while the problem is fresh in your head can be very productive.

Brainstorm and casual conversation are both important. They compliment each other in various ways, and the right practice of both can increase our productivity by leaps and bounds.

8 Things I Learned From Working at Startups

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eric tang

Taken by Justin Merriman, Tribune-Review

Last weekend I was fortunate enough to speak at the Build18 hackathon at my Alma Mater, Carnegie Mellon University. Unlike many of the hackathons I’ve seen in the “real world”, most projects here were not “business ideas”. They were true “hacks” - ideas created by the intellectual exhaust, experiments that exists for no purpose other than existance itself. I was super impressed by the technical depth of the projects.

At the awards dinner, standing in front of a room full of sleep-deprived college engineering students, I couldn’t help but to think back to 4 years ago. We were sitting in the same seats, filled with gumption and no particular direction, hoping to make a dent in the world. We wanted to be important, special, even rich, because we have earned the rights through the endless pencil-smeared pages of equations and the caffine-buzzed lab hours. “My heart is in the work”, says Andrew Carnegie. All you have to do is to keep your head straight, work hard, and eventually the dent will be made. Right?

As it turns out, direction and course correction is more important than hard work. Just as a car with a powerful engine but no steering wheel has very little chance of getting to its destination, effort is the pre-requisite for doing anything significant.

I had planned to share a slice of the startup life, maybe even inspire some of them to start or join a startup. But given the particular setting and timing (they were probably all cracked out from a week-long hacking session), the most efficient way to get my points across was to be succinct. I compiled everything I wanted to say into the following 8 bullet points.

  • If you haven’t read PG’s essays or don’t already read hacker news, just do it.
  • Iterate - It’s quite a remarkable concept. I alaways get a feeling of comfort when I know that I can just keep doing the same things over and over again, and my product will magically become better and better.
  • Launch early, launch often - Be lean. It’s something to strive for, but don’t kill yourself over it. It’s much more important to know why you should be lean than how to be lean.
  • Over-share your idea - Don’t be afraid that other people will steal your startup idea. The risk of hiding your idea and no learning from other people is much greater than the risk of some douche stealing your idea. Ask people who have done this before, ask people who you really respect, ask random people in coffee shops.
  • Always find ways to validate your idea - Think of your startup idea as the hypothesis, and your goal is to test your hypothesis through as many lenses as possible. The power of statistical approaches is much greater than statistics itself.
  • Define some metrics - Metrics are great. They keep you focused on the most important things. Find the thing that will kill you and do that first.
  • Avoid going to networking events - Also don’t think about raising money too soon. Both are HUGE distractions from building your product. If you are trying to be “one of the cool kids”, you are doing it wrong.
  • Don’t be a dick - The people you work with are your greatest assets, so be very careful of choosing who you want to work with. Once you’ve made that decision, treat them like a brother (or sister).

Startup is definitely a learn-by-doing experience, which means the students probably won’t do any of the above 8 things. But hopefully these tips will guilde them back towards the right path when they make a mistake.

How I Built This Blog: Jekyll + Disqus

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I’ve wanted to play with Jekyll for a while now. A delayed flight and awesome internet connection at the Pittsburgh airport finally presented me the golden opportunity.

Here is a step-by-step tutorial on how I build this site:

Install Jekyll

You should first install jekyll. There is a good tutorial on the Github wiki. But If you don’t want to follow the official tutorial, here is what I did.

Install the Jekyll gem by running:

gem install jekyll

If you want syntax highlighting for code blocks, you have to install a python module called Pygments.

sudo easy_install Pygments

Of course you have to have python-setuptools installed.

First blog entry

After installing jekyll, I created my site structure that looks like this:

      |-- _config.yml
      |-- _includes
      |-- _layouts
      |   |-- default.html
      |   `-- post.html
      |-- _posts
      |   |-- 2012-01-20-some-post-I-wrote.textile
      |   `-- 2012-01-21-how-I-built-this-blog.textile
      |-- _site
      `-- index.html

The best way to get started is to take a look at someone else’s project. Since I’m terrible at anything css/html related, I borrowed a lot of code from User Obsessed.

The _config.yml file contains configuration settings of the site. Here is what mine looks like:

    url: ""
    pygments: true
    exclude: [/bin, Gemfile, Gemfile.lock]
    markdown: kramdown
    permalink: pretty
    paginate: 10

      entity_output: symbolic

The index.html file is your homepage. The layouts directory contains the formating of your pages, and the posts directory contains individual posts.

To get a simple site up and running, I created config.yml, index.html, layouts/default.html and _posts/2012-1-21-sample-post.textile

After that, run

    jekyll --auto --server

You should see a server starting up. Go to http://localhost:4000 to make sure it’s working.

There are many other things you can do with this barebone site, refer to the Wiki for details.


Comments are important for blogs. There are many different ways to add comments to your Jekyll-powered blog, I chose to use Disqus because it’s easy to integrate.

Luckily Disqus has make this process SUPER easy. Here is what you have to do:

  • Sign up for a disqus account, register your domain.
  • Copy the embeded code to your _layouts/posts.html. Remember to replace “example” with your own shortname.
  • Reload the page.

That’s it!

That’s it! You’ve set up your first jekyll blog!