x
Henry Woodman
Founder, ICE Portal (exited)
In this deep-dive conversation, Henry Woodman shares the "scrappy" journey of a serial entrepreneur who never settled for the status quo.
Content isn't king — distribution is. Henry realized production is a zero-sum game and pivoted from virtual tours to distributing hotel photos to every travel site on the planet, a moat that took nearly two decades to build.
Say yes to everything, then learn to say no. Early on you take every job to pay the bills; once you find what you can win at, you must say no to everything that pulls you away from it.
Know your number and prepare the exit years ahead. Henry kept his number on his mirror for a decade, built processes so the business ran without him — and when Shiji agreed, the money was in his bank in 60 days.
Discipline is the underrated superpower. From competitive swimming to midday workout breaks, the wash-rinse-repeat consistency most entrepreneurs lack is what carried him through seven lean years.
