Hoala Greevy

Get up. Dress up. Show up. And don’t be late.


Hoala Greevy is the founder and CEO of Paubox, the leading provider of HIPAA-compliant email services. Paubox’s end-to-end email encryption works on any device without requiring additional apps, plug-ins, or logins. A serial entrepreneur, Hoala also founded Pau Spam, an email-filtering software service. Paubox is based in San Francisco.

Hoala recently celebrated Paubox’s 1,000th customer by giving away 1,000 spam musubi to San Franciscans and donating funds to Project Homeless Connect. An avid kayak fisher, Hoala holds the world record for the largest caught finescale triggerfish.

Where did the idea for Paubox come from?

The idea for Paubox came from talking to customers. In 2014, I had an auspicious lunch with the CEO of Make-A-Wish Foundation of Hawaii, Siana Austin Hunt, where we talked about the idea that would become Paubox. The rest went from there.

What does your typical day look like, and how do you make it productive?

I try my best to get a workout in before getting to the office, and then I stay at the office until I can’t work anymore.

How do you bring ideas to life?

I keep a journal. I used to call it a surf journal. Then, it became a kayak fishing journal. Now, it’s more or less just a journal.

What’s one trend that really excites you?

Paubox is killing the fax machine in U.S. healthcare.

What is one habit of yours that makes you more productive as an entrepreneur?

Compiling handwritten to-do lists.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Get up. Dress up. Show up. And don’t be late.

What is one strategy that has helped you grow Paubox?

We use customer feedback as a road map of what we should build and in what order we should build it. That kind of feedback is, after all, how Paubox got started.

What is one failure you had as an entrepreneur, and how did you overcome it?

In my opinion, the only true failure is giving up.

What is the best $100 you recently spent?

Probably buying food for my staff. Sharing a meal is a great opportunity to spend time together.

What software and web services do you use? What do you love about them?

We’re mostly an Amazon Web Services and Apple company. We love their ease of use and their established brands.

What is the one book that you recommend our community should read?

Crossing the Chasm ” by Geoffrey Moore. One of our primary strategic goals for 2018 is to cross the chasm between early adopters and mainstream consumers. We want to become the preferred mainstream solution for the HIPAA-compliant email market.

Tell us something that’s true that almost no one agrees with you on.

Healthcare is the last American business segment to use email in the workplace.

What advice would you give your younger self?

Stay focused.

What is your favorite quote?

Ua mau ke ea o ka aina i ka pono.” It’s the Hawaii state motto and has a backstory to it. The most common English translation of the phrase is this: “The life of the land is perpetuated in righteousness.”

Key Learnings:

  • Keep a journal.
  • Stay focused with handwritten to-do lists.
  • Share a meal with your teammates.
  • Get up. Dress up. Show up. And don’t be late.
  • Read “Crossing the Chasm” by Geoffrey Moore.


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