Issue #02 | Maria Leonardi, Founder at Startup Hawaiʻi

Maria Leonardi is a serial founder based in Waikoloa, Hawaiʻi. She is the founder and CEO of Founder First, co-founder and CEO of Infinity Rack, and the founder of Startup Hawaiʻi, an organization that is building a tech startup and innovation ecosystem to create a more diverse, equitable, and sustainable economic future for Hawaiʻi Island.

Q: You’ve managed non-profits, worked as an investment banker, and run startup accelerators previously (among other things); what was it about those experiences that ultimately led you to venture out and start your own company (Founder First)?

Two things motivated me to start Founder First.

First and foremost, I absolutely love working with founders. I find a lot of joy in helping someone bring their dream to reality. Founders also tend to be fun people to work with; they are curious, driven, and passionate.

Second, the pandemic shifted my mindset. For years I let what I thought I “should” be doing drive my career choices and direction in life. The pandemic was a big wake-up call to be more mindful and intentional about what I spent time on.

So, in November 2020, I left my corporate job and started working independently with two awesome CEOs. Since then, I’ve also co-founded a solar company that’s disrupting solar roofing products.

Q: What was the genesis of Startup Hawaiʻi? Was there a particular event or moment that catapulted Startup Hawaiʻi into existence?

I’ve always been really passionate about rural geographic equity, or the concept that a person living anywhere with an internet connection should be able to access the same opportunities as someone living in a major urban area.

The pandemic greatly accelerated the acceptance of remote work and remote relationship building. I am a big supporter of remote work for a lot of reasons, the biggest being the equity that it can bring to industries where remote work is a possibility.

The concept that even the most remote places in the world should be able to connect to the global economy was the real catalyst behind Startup Hawaiʻi. I decided to pick startups, technology, and innovation as the strategy for change because it’s an area that I have experience. This is also a sector that can holistically drive positive change beyond any specific technologies or innovations produced in areas like workforce development, sustainability, and economic diversity.

Q: Startup Hawaiʻi quickly gathered interest from a lot of people around the state (myself included). Did you expect there to be such an outpouring of support for your mission outside of Hawaiʻi Island? What have you learned in the process?

I did not! I didn’t even expect the response I received on Hawaiʻi Island alone. I’ve recognized in the last several years that I struggle with doubting myself so there was always this fear that I would put myself and this concept out there and no one would care. I’ve learned it’s quite the opposite! We have such an amazing and energetic group of people that believe in the purpose behind Startup Hawaiʻi — the concept that we can create a more diverse, equitable, and sustainable economy here without sacrificing the character and culture of this place and our communities.

It’s been an amazing learning experience for me so far. The biggest things I’ve learned are not to let external pressures (perceived or real) determine when, how, and what I execute, how incredibly supportive the Hawaiʻi Island community is, and to believe in myself!

Q: I remember attending the inaugural Startup Hawaiʻi meetup back in August 2022; what’s changed since then, and how has your worldview shifted (if at all)?

Since that first event, the community has grown from 75 people to nearly 300 (including 60+ volunteers), we’ve hosted four more events, established new partnerships, and greatly refined our vision and ecosystem framework. We’ve also received a micro-investment from Vibrant Hawaiʻi, which is actually where the concept and core team originated.

I haven’t experienced any major worldview shifts since then but I have learned how difficult and complicated it is to activate and deploy an ecosystem network, even when there are a lot of interested community members. Ecosystem builders don’t get enough credit for the work they do around the world!

Q: What motivates you to keep working toward a more equitable and sustainable future for Hawaiʻi?

I recently took part in a 12-week program run by Purple Maiʻa (Ka Maka ʻĪnana) that focuses on Place-based Design in a Hawaiian Context. There was one section of the course that discussed the meaning of “kuleana.” One of the many concepts that were shared is that we have a responsibility to use our competencies or skills for the betterment of society. This is an incredible and powerful place that I am very privileged to call home. I feel that it’s my responsibility to use my skills and experience to give back to this island.

On a more personal level, I watched a lot of my friends growing up having to make the difficult decision to either leave the place that they loved to find jobs to make a stable living or stay and struggle, or at the very least, get creative about finding ways to earn a living in a rural, wilderness community. This is where my passion for rural geographic equity comes from. Having to leave home is a decision that I donʻt think any individual should be forced to make.

Q: What do you believe is standing in the way of creating a more diverse, equitable, and sustainable economy here in Hawaiʻi?

There are a lot of challenges when it comes to creating an equitable and sustainable economy here in Hawaiʻi — housing, infrastructure, and transportation, just to name a few. There are a lot of really smart people working on these kinds of things so I’ll focus mainly on obstacles that are most closely related to the work I’m doing at Startup Hawaiʻi.

Startup Hawaiʻi is addressing one of the obstacles in its efforts to connect across silos and create a more coordinated and connected effort. There are a lot of great organizations and individuals working to achieve the same goal but it’s fairly fragmented at the moment.

Another big issue that I see is the diversity of access to professional opportunities. If you are interested in certain professions (e.g., technology, finance, etc.) you are very likely to have to leave the island to pursue that career. On top of that, many technology roles require experience even at the entry level. We don’t have many outlets for students or career switchers to gain the initial experience that’s often required to access the remote jobs that are available.

We are also focusing on providing support and resources to idea-stage companies as well as scaling companies (post-accelerator or seed stage). There is a lot of support in Hawaiʻi for early-stage companies but not as much support for founders to take an idea and create a viable business or for a company that has proven demand and needs to transform into a business that is able to scale operationally.

I might be an outlier in my opinion here, but I often hear that funding is an obstacle but I don’t agree. I strongly believe in the “if you build it they will come” concept. If we’re building great businesses that are scalable, and we build good foundational relationships outside of Hawaiʻi, funding will come. It’s not going to be easy, but we’ve seen the monopoly held by major U.S. regions (Bay Area, New York, etc.) weakening. While they still dominate the landscape, other ecosystems are starting to be more visibly active and I don’t see any reason why Hawaiʻi can’t be one of those growing regions.

Q: What does Startup Hawaiʻi look like five years from now? What do you hope you will have accomplished?

My vision for Startup Hawaiʻi is to be the go-to hub for technology entrepreneurs and talent on Hawaiʻi Island, and for our framework and ecosystem to serve as a model for other rural and remote locations. My goal in the next five years is to launch a talent and startup studio alongside an angel or seed fund, to run regular events to connect the community, and to serve as a facilitator for ideating solutions to solve critical community issues.

Q: What’s the best way for people to support Startup Hawaiʻi right now?

There are several ways depending on how involved you would like to be. First, join our community online to stay updated on news, programs, and events (we have virtual and in-person events). Second, you can elect to be involved as a mentor, domain expert, ecosystem builder, or advisor, among other roles (or suggest your own role!). And lastly, you can choose to help us with fundraising for general operations or specific programs.

Q: What’s the best way for people to connect with you?

Via LinkedIn or email ([email protected]). I’m also a member of the Hawaiʻi Slack channel and can chat there as well!

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