In part two of “my struggle”, I recount my past from post-college on, including my life in Boston, my jobs at companies like AT Kearny, PricewaterhouseCoopers, and others, the formation of my company, my TASM Lab music albums, my band the Hudson Debacle, my marriage, my kids and more.  Along the way I explain what life lesson I learned through my various endeavors and share some music that I wrote and performed.


Listed below is my outline for the podcast.  No need to read, just for search bots:


Episode 20

Isaac joke

How to be myself

Not just history, but what I learned

On moving: it’s not that hard, if you want to be somewhere different to do different things, you have to do it.

PTR and volunteering for anything, being excellent.

The ultimatum

AT Kearney and changing how they worked.

Lesson: play up to their level, invite your self into the adult conversation

Thing and nothing

  • What I learned: I could write anything. Working hard on the product is not enough

Don’t forget ole computy

Out of the blue

  • What I learned – do something different if you want something different to happen.

Jen and the toilet paper

  • Marriage
  • The polo scene

Chris and Xavi

Administrative weenie


  • Business boot camp extreme
  • Bear creek
  • – The dump
  • – Scott’s plane ride
  • – Suicide
  • – The 25 hour day
  • – Proposing to Jen over the phone
  • What I learned: how to talk to anybody and be considered worthy of the room
  • I also learned that I didn’t want to work hard.


The essential cubicle nosepicker

What I learned: Simple can work

Pamet River

  • The interview
  • The destruction
  • The 500MM RFP
  • My summer with Ayn Rand and Reason


  • 9/11 and getting laid off
  • Building a product and seeing it taken from me
  • Going home
  • Staying home

Also did a couple projects with Derek Sivers

The Hudson Debacle

What I learned: Absolutely nothing

The decision to go on my own and to build businesses.

  • Learning: you have to do something different

SAM-Lab, Inc.

  • Learning: do what I’m good at.

Also picked up golf


  • What I learned: if you don’t give something your attention, it will fail.
  • Same with Leapthought, being a landlord, GleeCD

Lose some weight

Let’s have a baby!

Let’s buy a house!

An Adulty Adipisci

Let’s hire an employee!

  • The good and the bad
  • What I learned: good employees can change your life, bad ones are easy to spot, mediochre ones are like a slow boring death

Let’s have another baby!

Meet Ron Paul

The Brambles of Hell

Let’s hire some more employees

Let’s have another baby!

A new focus: personal liberty

The snow sucks

Mom’s cancer

Moving time

Two years ago

The biggest lesson: if you want to do something different than the average, you have to do something different. Being good at the same path everyone else is taking is being average.


My goals for the future.