Banking on a Brighter Future for Indigenous Americans

In 1969, a congressional report concluded that “our nation’s policies for educating American Indians are a national tragedy ... the ‘first American’ has become the ‘last American’ in terms of an opportunity for employment, education, a decent income and the chance for a full and rewarding life.” More than half a century later, despite legislative reforms, American Indian and Alaska Native people continue to face significant barriers to academic achievement: Today, just 15.4 % of Indigenous Americans have earned a bachelor’s degree or higher (compared with 32.9% of the U.S. total population) — and just 42% of those who do attend college complete their degree within six years (compared with 64% of all other students).  

Randy Estrin, MSF ’26 isn’t deterred by these statistics. An Alaska Native born and raised in Ketchikan — a town of roughly 8,000 in Southeastern Alaska — he enrolled in Bentley’s Master’s in Finance program after earning a bachelor’s degree in business administration from Haskell Indian Nations University in Lawrence, Kansas. Estrin is also an entrepreneur and business owner — he started Clan House Tours, a company offering cultural and wilderness excursions, with his father in 2022 — and is currently serving a year-long term as Emerging Leader for the Central Council of Tlingit and Haida Indian Tribes of Alaska.

We recently spoke with Estrin to learn more about the opportunities and obstacles he encountered during his educational journey; what he’s experienced as a tribal leader, business owner and full-time graduate student; and why he’s confident a career in investment banking will help him empower his Alaska Native community.  

Q:  Why do you think American Indian and Alaska Natives are consistently underrepresented in higher education?  

I’d say one of the biggest barriers is financial. The poverty rate for American Indian and Alaska Native people is higher than any other group, so when you factor in the high cost of tuition, there aren’t many young people willing to put themselves — or their families and tribal communities — into that amount of debt. Even the relatively low tuition costs for tribal colleges and universities like Haskell, which are subsidized by the federal government, can seem out of reach for a lot of Native families.

Cultural differences are another factor. Native households don’t put a lot of emphasis on going to college. Some of that is motivated by historical distrust — how the government used boarding schools as assimilation tools — but mostly it’s because of how much we value community. Where I’m from, you’re never really thinking about just yourself or your parents; you’re always considering the needs of your extended family — your cousins, grandparents, great aunties and great uncles — and your village or reservation as a whole.  

Going to college usually means leaving your community, and it’s really hard to maintain your traditions and contribute to the community if you’re not there. When I’m here at Bentley, for example, I can’t help my family hunt, fish or harvest. Which is important, because a lot of Alaska Native villages like mine struggle with food insecurity and sovereignty — the right to make our own decisions about how to produce, distribute and consume our traditional foods.  

As a Native person, there are a lot of things you leave behind, a lot of sacrifices you have to make, if you decide to go to college. And I think a lot of young people are afraid to lose that connection to their culture.  

Q: Given these considerations, how did you make the decision to go to college? And why did you choose to study business?

My family doesn’t have a strong history of education. One of my grandfathers didn’t finish high school, and the other didn’t make it past the third grade. But my mom always emphasized the importance of education. In fact, she took some classes herself at the local community college, and I have fond memories from middle school of the two of us doing our homework together, because we were both learning algebra at the same time. My grandmother really encouraged me, too. Whenever I’d go over to her house, she’d bring out flash cards and quiz me on my multiplication tables. By the time I was a freshman in high school, I knew college was something I wanted to pursue.  

Business seemed a natural fit, since I grew up in an entrepreneurial household. In middle school, my dad had his own home inspection business, and I’d often go to work with him, helping him check out the crawl spaces and stuff. Later, he and my mom started a rental car business. A few years ago, we launched Clan House Tours, one of the only Native-owned, family-owned tour operators in the area. Tourism is a big industry in Ketchikan, since we’re the first stop for any cruise line that sails Alaska’s Inside Passage. Our tours showcase our landscapes and wildlife — we’ll often see black bears and bald eagles — and our Tlingit and Haida traditions, like berry picking and woodcarving. Even though it’s a business, it’s about more than making money: It’s an opportunity to educate people by sharing our firsthand experiences and family stories, teaching them things about Alaska Native culture that aren’t written about in history books.  

I also believe that studying business is the best way I can serve my people. It’s really important for tribal leaders to understand how to manage financial resources, because a thriving and sustainable economy is the key to ensuring sovereignty.  

Q: What drew you to Bentley — and how would you characterize your experiences here thus far?  

I first heard about Bentley from Hussein Montoya, MSF ’20, MBA ’21, another Haskell alum. He had great things to say about it and he encouraged me to apply to the Discover Bentley program (a three-day, on-site summer program for prospective graduate students from underrepresented communities). I was really impressed by the academic and extracurricular programs, and I left Bentley knowing it would provide a great start to my professional career.  

Now that I’m here, it’s even better than I expected. I didn’t realize how much I’d appreciate being around other students who are equally motivated and ambitious. My professors are outstanding — they make every lesson really interesting and engaging. And I’ve become involved in extracurricular activities: I’m a member of Bentley’s Graduate Student Advisory Board and the Indigenous Education Steering Committee.

I’ve also really enjoyed getting to know people from different countries and cultures. At Haskell, pretty much the entire student body is American Indian and Alaska Native people, so there wasn’t a lot of diversity in terms of non-Native groups. But here, we have students from all over the world, and I think that’s a really important part of the college experience. My partner, Hannah Poorman, MBA ’26, and I live off campus and we have two roommates who, like us, are also studying at Bentley. They’re both international students — one is from India and the other from Vietnam — and it’s been great getting to know them and learning about their cultures. 

Q: How did you become interested in investment banking? What do you plan to do with your finance degree after graduation?  

I learned about investment banking from a friend I met during the Discover Bentley program. The more I learned about the field, the more it spoke to me — especially since, historically, tribal communities have had such limited access to credit and capital.

Last month, I attended the National Congress of American Indians in Las Vegas in my capacity as an Emerging Leader. I was listening to a panel of investment bankers speak about a tribe they were working with that left $10 million sitting in an interest-free banking account for 10 years because they didn’t know how to invest it. It was heartbreaking to hear, but it really underscored the fact that tribal nations often struggle because they don’t know how to use the financial resources they have.

Over the last year or so, I’ve been fortunate to participate in a variety of programs — including Wall Street Bound, Evercore’s Diversity Leadership Summit, JumpStart’s Path to Investment Banking, the Hoover Institution at Stanford University’s Indigenous Student Seminar, the Native American Finance Officers Association Leadership Summit and the 2024 US SIF: The Sustainable Investment Forum conference (where I was honored to be selected as a Peter DeSimone Student Scholar) — that have not only given me a deeper understanding of investment banking and financial management but also provided invaluable networking opportunities. At the same time, as an Emerging Leader, I’ve gotten a firsthand look at the complexities of tribal governance; in particular how our legal status as independent nations creates additional barriers to economic development, like preventing us from developing land or collecting taxes.  

To be an effective tribal leader, I believe that you need to understand all the different ways that money “works” so that you can make decisions that ensure long-term prosperity. And that’s exactly what I hope to do once I leave Bentley — leveraging the expertise I’ll gain in investment banking to create a strong and sustainable financial future for my people.