Leadership Series with Hoala Greevy, CEO of Paubox

Last month, I had the opportunity to interview Hoala Greevy, Founder & CEO of Paubox, for our HCCNC Leadership Series. Hoala, as both a person and professional, means so much to the HCCNC, our broader Hawaii-SFBA community, and myself personally. He is proving to the tech and business world that those from Hawaii, and specifically Native Hawaiians and public school attendees, can be successfully entrepreneurs and business leaders. Success breeds more success, and am so thankful to Hoala for paving the way for future generations of entrepreneurs, students, and others coming from Hawaii to the San Francisco Bay Area. You can check out the full video below as well as my notes from the conversation and Q&A.

Hoala’s background and education

Hoala is a proud Oahu-born, Native Hawaiian, and self-described ‘Townie’ who is incredibly passionate about McKinley, his alma mater. In Hawaii, we’re known for where we went to high school, and statistically speaking McKinley and many other public schools are not known for alumni that have business nor financial success. He wanted to play baseball, so ended up going first to Menlo College to play D3, then attended Portland State. In college, he focused on what would get him his degree while pursuing computer and entrepreneurial related activities on the side. He was awarded with a KHS scholarship which allowed him to graduate school with very little debt. The scholarship he received no longer exists, and is a major driver in his efforts to fund scholarships like the Paubox Kahikina Scholarship to help Native Hawaiian students pursuing STEM degrees increase their chances of success.

Beginning his career in San Francisco during the Dot Com era

Following graduation, Hoala moved to San Francisco to begin his career at Critical Path, a software company focused on providing email-related services. For Hoala, San Fransisco has been and continues to the tech hub, but it does have a boom and bust nature to it, where there are periods of massive excitement, drop off, and then excitement again. At that point, it was very wild-wild west. Today, the internet business models have become more viable and even more talent is attracted to the industry, and San Francisco will boom again in the future, with so much tech and intellectual stimulation here.

Coming back to Hawaii and founding PauSpam, Hawaii’s first SaaS company

To take care of family, Hoala moved back to Hawaii and ran a Linux consulting business. Back in those days, (email) spam had become a massive problem, and he heard many of his consulting customers begin to complain about it. There were a bunch of people talking about a solution, but no one actually shipping a product. He seized the opportunity to be first-to-market, and, with the help of a few all-nighters, shipped out the product. At that point, SaaS and cloud was not present other than a few web-hosting companies. There wasn’t even really the ability to place up servers, so SaaS was something that was a necessity for them, where nowadays it’s just become standard practice.

Founding Paubox and moving to the SFBA

Similar to the founding of Pauspam, he continued to listen to customers. At a lunch with one of his customers, the CEO of Make-A-Wish Foundation, and she had a business problem with health records and HIPPA, so they shipped a product. This focus on listening to the customer and building their roadmap on that is core to the Paubox DNA. After evaluation everything, they realized it warranted a separate solution and company given the different dynamics of the problem and product. His hypothesis at the time was that they would be able to successfully build the business from Hawaii, but looking back he probably should have moved to the SFBA sooner given the combination of SaaS expertise, time differences, etc. They would get interest from people, but at that time in 2014/2015 they wouldn’t take them seriously in comparison to the Microsoft and Googles of the world. If you’re focused on tourism tech, renewable energy tech, etc, Hawaii would have been more viable for them, but for SaaS and especially at that point in time, it wasn’t. They ended up actually applying nine-times to accelerators, and finally got into 500 Startups, so they moved to the SFBA following. He heard about Daryl Higashi and the HCCNC from contacts in Hawaii, and came to his first mixer in San Jose.

Business goals and how to stay successful

Since Paubox is a SaaS business, the goal is pretty clear in that it is recurring revenue. Their goal is to get to $100M in ARR. They’ve settled on the OKR attainment framework, and it’s working well for them.

For general success, there are three.

First, in software, you have to launch. You absolutely have to launch. At Pauspam, pulled all nighters and launched. Not the healthiest thing to do, but it got to the point where he couldn’t sleep without it being done.

Second, customer feedback is very important in their business, and SaaS. Need to stay attuned to that.

Third, setting goals and building. Right now there at 40, were at 15 not that long ago. Need to write down the goals, and just get after them.

But ultimately, it comes down to launching. You need to launch!

Giving back to the community and the Paubox Kahikina Scholarship

One of the takeaways of doing business in Hawaii is that the leaders always give back. When I moved to SF Bay Area, I wanted to continue that tradition and culture. We are going to display the traits of a leader, and over time we will be seen as a leader. Bringing that value from Hawaii forward was important to us. When we hit 100 customers in SF at our office across the street from the BART stop at Mission & 16th, we gave away 100 musubis and 100 pairs of socks to show our gratitude.

We did this again at 500, 1,000 customers as well, and thought about, what’s the best thing we can do with a few thousand dollars. And so I thought back to my scholarship. And so we launched the Kahikina scholarship in honor of my grandmother. This ties back into software engineering being an honorable professional, and Hawaii is lacking this right now. When is the last time you read a story about two roommates creating an app or a company out of their dorm at UH, HPU, or any colleges in Hawaii? There are no stories of this, and not a lot of software engineers coming out in Hawaii.

So Nick Wong, who also was a recipient of the HCCNC Scholarship, was our first recipient and he now works for us. We use Scholars App, which is a mutual customer, and talking with Elliott Mills from the KHS Board, confirmed that there is no more STEM scholarships for Native Hawaiians, and so we expanded our scholarship to beyond software and for STEM and not just software. We also make the scholarship funding recurring (like our business model), and are building out a STEM network for the recipients so they have advisors and contacts in the industry. It works both ways, since the advisors want to find people to hire. Since it didn’t exist, I figured I needed to do something about this.

How to stay healthy, safe and sane as an entrepreneur

In addition to pursuing hobbies like kayak fishing, tries to sleep a lot and journal. Sleep is important since it helps longevity. Writing down his thoughts helps to keep you de-stressed and not having things when you’re done. Exercise is also critical, and since business is a marathon not a sprint, you need to make sure to take the time do this. Also tries to sit down, unplug, meditate, and take in from nature.

Q&A Sections

Darlene: How do we encourage more students to pursue business and STEM careers?

Turning recipients into the marketing engine of the scholarship. Hoping over time and at scale their own recipients will be the marketing engines for other kids interest. Need to promote not only software engineering being a honorable profession, but also the monetary side where they can make great pay and generate long-term wealth. Need to provide numbers around average pay, that the most successful people in the world are often software engineers, so you have a lot of demand for software engineers, there is speed to market, and there’s this potential of wealth generation, and top companies have CS backgrounds. This will encourage people to pursue it and it’s an honorable profession. In Hawaii, there is a major problem with public school students not even knowing what Computer Science is. Ultimately, you want to see people looking like you having success, and at some level we’ll need to promote myself, Paubox, and our recipients as examples.

Kyle: I volunteer to help students in Hawaii network, but unless they want it, it’s hard to get them to pursue this further. What are your thoughts on getting more exposure to people so us, the HCCNC, others, can help make the Hawaii workforce and students more competitive?

I don’t know the full answer to this one, but we want to help companies provide accelerator or networking like services, from Blue Startups, ManaUp, 500 Startups, and even HCCNC, so we create a virtuous cycle. But it’s a hard question to answer.

Michael:

What would be the three books you’d recommend people to read?

Tough questions and these are probably ones I’ve read recently, but, Crossing the Chasm, Only the Paranoid Will Survive, and Why We Sleep.

Outside of Paubox, what gets you excited for and excited about for the future?

I’m so focused on Paubox that’s a hard one, but selfishly, starting a family with my wife, and one day breaking a record for the largest fish caught from a kayak unassisted. World record is at 224 lbs, and I think a bigger fish is out there for kayak.

What type of businesses should people refer and send over to talk with your team at Paubox?

We focus mostly on healthcare, but have nonprofits and other organizations, anyone dealing with HIPAA compliance hurdles. We also deal with a lot of HR groups within large enterprises that deal with health data, who use Paubox for their team. So please send them over to us at www.paubox.com.