Category Archives: The Journey

I’m Tired of Running My Successful Start-up After X Years. What Should I Do?

The Holidays are here — and I hope you are taking a vacation. Because, I know you are tired.  Really tired.  SaaS is hard.  The New Revenue dials and dashboards in Salesforce go back to zero every month, or at

I’m Tired of Running My Successful Start-up After X Years. What Should I Do?

The Holidays are here — and I hope you are taking a vacation. Because, I know you are tired.  Really tired.  SaaS is hard.  The New Revenue dials and dashboards in Salesforce go back to zero every month, or at

I Don’t Know about CEO Coaches. But We All Could Use CEO Trainers.

Once you’ve been venture backed, if not before, you’ll hear a lot about CEO Coaches.  The classic example is Bill Campbell, CEO coach to Steve Jobs, Google, Mark Pincus, and other leaders in between.  VCs generally have great networks of ex-CEOs

I Don’t Know about CEO Coaches. But We All Could Use CEO Trainers.

Once you’ve been venture backed, if not before, you’ll hear a lot about CEO Coaches.  The classic example is Bill Campbell, CEO coach to Steve Jobs, Google, Mark Pincus, and other leaders in between.  VCs generally have great networks of ex-CEOs

Great CEOs are Really Coaches, So Let’s Learn from Phil Jackson

“I don’t care if it’s 82-and-0 this year, you’re f***ing gone.”[5] — Jerry Krause, Owner of Chicago Bulls to Phil Jackson, The Greatest Coach Ever, After Phil Jackson Won His 5th NBA Championship, and just Before He Went On to

Great CEOs are Really Coaches, So Let’s Learn from Phil Jackson

“I don’t care if it’s 82-and-0 this year, you’re f***ing gone.”[5] — Jerry Krause, Owner of Chicago Bulls to Phil Jackson, The Greatest Coach Ever, After Phil Jackson Won His 5th NBA Championship, and just Before He Went On to

If You Go Small, You’ll Never Have a Legacy

Small can be beautiful in start-ups.  Take no venture capital, build an eight-figure business, put the profits all in your backpocket.  You can end up having a villa in Italy full of Pagondis, like the Basecamp guys.  Boom. But. The

If You Go Small, You’ll Never Have a Legacy

Small can be beautiful in start-ups.  Take no venture capital, build an eight-figure business, put the profits all in your backpocket.  You can end up having a villa in Italy full of Pagondis, like the Basecamp guys.  Boom. But. The

To a Better Place: When is It Time as CEO/Founder to Move On?

Yesterday it was announced that Shai Agassi, one of the most successful software entrepreneurs/executives of all time, had left Better Place, his latest company and incredibly aggressive plan to make electrification of cars work via replaceable batteries, after 5+ long

To a Better Place: When is It Time as CEO/Founder to Move On?

Yesterday it was announced that Shai Agassi, one of the most successful software entrepreneurs/executives of all time, had left Better Place, his latest company and incredibly aggressive plan to make electrification of cars work via replaceable batteries, after 5+ long

The Workday IPO and ‘F You Money

The other day, a VC asked me about a founder he was thinking of investing in.  He asked me if this founder had, quote, ‘F You Money.  {I learned how this was spelled when a Businessweek article this week used

The Workday IPO and ‘F You Money

The other day, a VC asked me about a founder he was thinking of investing in.  He asked me if this founder had, quote, ‘F You Money.  {I learned how this was spelled when a Businessweek article this week used

Those Brief, Rare Moments of True Wonderfulness in Start-Ups

There are many great reasons to do a start-up — career advancement, (sort of) being your own boss, doing something new, creativity, etc. etc. But I wonder if it’s really a handful of brief moments of True Wonderfulness than makes

Those Brief, Rare Moments of True Wonderfulness in Start-Ups

There are many great reasons to do a start-up — career advancement, (sort of) being your own boss, doing something new, creativity, etc. etc. But I wonder if it’s really a handful of brief moments of True Wonderfulness than makes