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It takes 3 years.

The end of 2013 marks roughly the three-year mark for my company. As I reflect on where we are today, from initial product, to an advisory round, to seed funding and then to raising our Series A in December 2013, one thing that I’ve always perceived from came true: it takes roughly 3 years for you to truly figure out if what you’re working on can be a business.

Once you hit that 3-year mark, and you’ve figured out a way to stay alive, some magical things do happen. Now, just to be clear, after the first 3, it’ll take you 2 to 7 more years after that to make it a wildly successful business;..


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..


How to Interview an Engineer for your Startup

There has been some concerns about putting our hiring process “out in the open” while we’re still interviewing for our Lead Engineer position, don’t fret — we’ve got plenty more fun case studies like these! If you are looking for your next adventure and want to join an awesome team, shoot me an email:

Also, there is a great discussion thread going on over at Reddit.

Over the past week, I’ve been interviewing for the Lead Engineer position here at ToutApp. I’ve never been a fan of interviewing. No matter how elaborate the process, we all know it often comes down to that team..

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..


The New York Startup Scene is Important, but for Different Reasons than You Think…

Now that Ron Conway, Paul Graham, Dave McClure and many others have opined on how New York is and isn’t important, I think its time some real New Yorkers shared what their thoughts are about this scene. I’ll start.

As an Entrepreneur straddling both coasts, I get asked the same question almost every day: “So are you going to stay in Silicon Valley or go back to New York?!” The questions intensified when I went back this past week, so I decided to reflect on it a little. I had always been bullish about New York but after spending this past summer in California, and after having spent about..


Reflecting on my Summer at 500Startups

About four months ago, I packed up my bags, said goodbye to my friends, family, and wife in New York and ventured out to California. I had been fundraising for Tout and during that process made the decision to join Dave McClure’s 500Startups accelerator program.

This post outlines my key thoughts and reflections on the overall experience of being part of Batch 001 of the 500Startups Accelerator Program.

Note that this is a seriously long blog entry, so you may want to skim through the headlines first and then zoom into the parts you are interested in.

Thoughts on startup accelerators in..


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..


Tuesdays work best

Through December and January, I’ve been meeting up with a ton of amazing people from the NYC startup scene lately. Over coffee, lunch, dinner and drinks, we talk about our respective projects, our beliefs, about how NYC feels just-so-different these days, and most importantly, we work out who we can connect from our respective networks to help each other out. I’ve even started to experiment with holding Office Hours through (an awesome idea/service created by Nate Westheimer).

This has been an excellent way to not only make new friends in the industry, but also to get new..

I quit my job. Shipped 2 products. Launched a Services business with clients. Now what!?

I quit my job. Shipped 2 products. Launched a Services business with clients. Now what!?

My plans for 2011 has been marinating in my mind for the last few weeks. Staying true to the spirit of this blog, I wrote out this blog entry on my Game Plan for 2011 both to share my thoughts and to aide in my own thinking process.

Note: Originally, I was going to do this as a 2-part post. I’ve changed my mind and consolidated it into one.

Major milestones of 2010:

  1. I quit my day job through a principled decision making process
    How I made a principled decision to quit my six figure job
  2. Launched Braintrust, a collaboration tool for small tight-knit groups of people
    Blog: Introducing..