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Startup Principles


This is great. But I’m not coming back to your awesome web-app after signing up.

Almost every other day in Hacker News, I find the announcement about an awesome new web-app that potentially solves a critical problem in my day to day life. When it comes to the web, we’ve gotten very good about landing pages that clearly communicate values and absolutely frictionless signups that lets me get into the app with the click of a button.

I’ll Sign Up. I Probably Won’t Be Back

I sign up, go through their new user experience, take a look at their snazzy and beautiful interface and then I move on. Regardless of how many new applications I try, in reality, the actual applications I..


Jab, Punch, Jab — the Startup Mantra

Recently, I took up Boxing. Not the Taebo Cardio punch in the air boxing, also not the get into a ring and fight someone boxing; a middle ground crazy workout three times a week for an hour including a punching bag and spar in the ring boxing.

One of the biggest things I like to do is to look for patterns in life and draw them to core principles that weave together everything you do in your life. Core principes are powerful that way because no matter the situation, you can still apply them to solve problems.

My boxing instructor told me, if there is one thing I want you to learn in this..


Take It Easy

One of our investors, Ben Li, keeps a private wiki for his portfolio companies. It is a place where we can ask questions, have discussions, and just exchange ideas. As I was going through my backlog of emails today, I came across an email from him about one such discussion.

It said:

Subj: Diaspora Co-Founder Ilya Zhitomirskiy passes away at 22 

Hi TK,

I hope you are very well always.


When your time allows, you may share what you think about it in the wiki. Thanks.

Ben Li

I had no idea someone had passed away in the startup community. That too,..


Customer Service at Startups

One of the things I’ve been thinking about lately as I build Tout as a business is how we deal with Customer Service. It’s the natural progression of things, you first figure out how to build a product that people give a damn about, then you get them to actually use it, and then you come to the realization that a) people aren’t perfect and b) software isn’t perfect. Enter: Customer service, and the pursuit of “Great customer service.”

“Great Customer Service” is not a real goal

After nearly a year of growing Tout, I went from doing all our customer service via email — to getting a..


How I Hired Employee #1 for Tout

About two weeks ago, I hired Derek Hopper, Employee #1 for Tout. It was an intense moment for me and a big decision. There are a lot of questions that start swimming through your head as you start to make a hire (especially when it is your first hire). So in true form to this blog, I sat down and wrote down some key principles that would help drive my decision making process. These principles were based on my own experience in hiring in my previous jobs and from what I’ve read online.

The Cliff-Notes-Version

For the anxious, here is a summary of the key principles I defined. You can read..


Why I’m switching from being a bootstrapper to a funded startup

I’ve decided to stop being a bootstrapper and seek angel funding. This entry talks about why.

To set the context: Last year, I quit my day job and decided to experiment with a number of different product ideas. In the beginning of 2011, I reflected on the year of experimentation and shared my game plan for the year in a blog entry titled: I quit my job. Shipped 2 products. Launched a Services business with clients. Now what!?

As I said in my gameplan, there were a number of hard decisions I made in the beginning of the year. The most important decision being the one to focus on Tout and..


Think about your values before you start or pivot your business

This video is from a talk I gave at BootstrapMD right before our panel discussion (the first in my career). The theme of the panel was “Getting to Plan B” — what to do when your business isn’t quite working and you need to pivot.

Pivots are a Change of Direction

A pivot is a change of direction for your company. That’s all it is. I think with the word “pivot” becoming so popular in the tech media, its easy to make pivoting a huge mystifying and complicated thing. The key new idea that the word “pivot” brings is that if you want to have a successful change of direction, you want to make..

How I made a Principled decision to quit my Six Figure job

How I made a Principled decision to quit my Six Figure job

It has been about a month or so since I quit my Hedge Fund job and jumped right into building consumer facing web-products on my own. Today, the decision to quit feels like a no-brainer. As a matter of fact, I can’t even imagine how I ever put up with a standard 9 to 5 in the first place.

Nevertheless, for the months leading up to me quitting, and for the time I actually made the decision to quit, absolutely nothing about it was easy. It was incredibly scary, it was hard, totally nerve wrecking. But through it all, I managed to organize my thinking process, and find a way to make a..


3 ways to show screenshots of your product

As I’ve been working through and applying my 9 Principles behind an Effective Landing Page, I’ve been experimenting with different ways to “show” what Braintrust and Tout does. So far, I’ve found about 3 ways to effectively show people what your app does, and 1 that I’m absolutely in love with.

There is the “show the app in all its glory, and point to stuff and explain what is going on without getting in the way”

Then, there is the “show the app in all its glory, but don’t count on people moving their eyes back and forth AND reading so put it the explanations on top of the app” way



The most fundamental principle for startup success

It bothers me how there is so much dogma going around on how to effectively build your startup. The latest was Paul Graham’s essay on how you should only work on organic problems.

Although I love his essays, this particular one inspired me to think about the principles around picking the right problem to solve, because I don’t think its simply about “my problem” vs. “others.”

While thinking through this in a principled way, I think I came across what I believe is the most fundamental principle for any business (including startups). The principle is: Focus on problems you can understand.