Boston Speaks Up (BSU) is a podcast owned and operated by Value Creation Labs.
Michelle De La Isla has taken on many influential roles throughout her career, including those of an instructor, advocate, director, mayor, and now, CEO. In her current role, De La Isla is leading Hack.Diversity, an organization dedicated to enhancing diversity within the tech industry by connecting underrepresented talent with meaningful opportunities. Her work at Hack.Diversity underscores her commitment to creating pathways for marginalized individuals to succeed in the technology sector.
Before her tenure at Hack.Diversity, De La Isla had a diverse career experience, where she encountered the challenges faced by underrepresented groups firsthand, in various environments. Across her experiences in higher education where she served as a Biology instructor at Butler CC, in community development where she served as CFO of Housing and Credit Counseling, Inc., and in government policymaking where she served as the Mayor for the city of Topeka, De La Isla has nurtured a deep understanding of the systemic barriers that hinder diversity and inclusion, which she has leveraged to advocate for more equitable practices in the industry.
De La Isla’s leadership at Hack.Diversity has been marked by significant achievements, including the expansion of the organization's programs and partnerships. By collaborating with tech companies and educational institutions, she has helped to enhance the support system for diverse talent, facilitating not only job placements but also career development through mentorship and training. Her strategic vision has led to measurable progress in increasing the representation of underrepresented groups in tech.
After years of dedicated work, De La Isla continues to be driven by a profound commitment to social impact and inclusivity. Her passion for service comes from the immense gratitude she has for all the people who supported her in her childhood and as she overcame barriers. There is a great responsibility to pay forward kindness when you have been a recipient. Through her efforts at Hack.Diversity, she is doing just that, and remains a pivotal figure in advancing diversity in the tech industry and inspiring future generations of tech professionals.
In this episode, we sat down live with Michelle De La Isla at Startup Boston Week. You can listen to our discussion embedded below or on any podcast platform you prefer: (YouTube, SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play):
Written Q&A:
From homelessness and single motherhood to becoming Mayor and a Harvard graduate, and now CEO at Hack.Diversity – how did you do it? Could you describe your childhood? And how did it shape you to lead such an incredible career journey?
I was born in New York City and raised in Puerto Rico—and if you’d experienced my childhood, you wouldn’t have expected me to be where I am today.
Growing up, I didn’t have much and I was raised by my hardworking grandparents. I was homeless by 17, pregnant at 19, and diagnosed with cancer at 22. These experiences could have easily steered my life in a different direction, but I had people who believed in me when I didn’t believe in myself.
There are a lot of people who share a similar story like mine: we’re told narratives about where we will go (or won’t go) in our lives. Sometimes, all we need is an encouraging voice to remind us that we can do great things.
I was fortunate to have a supportive church community in Puerto Rico that came together to help send me to college in Kansas. It took me eight years, but I graduated with my bachelor’s degree from Wichita State University. After graduating, I joined Upward Bound, where I realized I wanted to create opportunities for others, just as my mentors and support system had done for me.
I quickly became an advocate in Topeka, Kansas, getting involved civically and running nonprofits. I became Mayor of Topeka—the city’s first Afro-Latina and single-mother mayor—and eventually ran for Congress. Throughout my political career, I realized that we, the people, have stopped talking to each other because we disagree on things. This inspired me to fulfill my dream of attending Harvard University, where I focused on becoming a bridge builder.
All these experiences have led me to my role as CEO of Hack.Diversity, which has become home for me.
To achieve equity and belonging, we need to systematically break barriers and build access to create pathways to success. It’s an honor to work alongside the Hack.Community—Fellows, Alumni, Mentors, and supporters—to shape the future of tech. I’m grateful to our Host Companies—AWS, Liberty Mutual, Rapid7, Wayfair, athenahealth, ezCater, WHOOP, and CarGurus, to name a few—for partnering with us to increase access and representation in tech.
While serving as the Mayor of Topeka, what were some of the most challenging issues you faced, and how did you address them?
The timing of it all was one of the most challenging aspects of the role. I was the first Afro-Latina elected to the position, and just a month before I took office, Dominique White, a Black man, was shot by two white officers. Navigating this big issue while coming into office and working to bring the community together to heal was incredibly hard. The threats, fears, and challenges were very real, and the situation impacted me personally.
The other part was when I decided not to seek re-election as mayor during the final year of my term and instead ran for Congress. I had established many systems as mayor, but when I announced my decision in January, COVID hit in March. This meant I was running a Congressional campaign while managing a city during the pandemic, trying to ensure our citizens were safe and alive and had all the information they needed. The hardest moments were those of real present danger, where people had very different opinions. My role was to be a translator, conveying proper information while working to bring the community to get through the crisis.
In your opinion, what are some of the most effective (and actionable) ways we can all support the career development of underrepresented talent in tech beyond just placing them in jobs?
This is a great question and it gets to the heart of what Hack.Diversity actually does.
Our Fellowship offers robust industry and internship readiness to prepare Fellows for their first tech internships. This includes developing a growth mindset, managing imposter syndrome, effectively navigating workplace dynamics, and managing up. Our Fellows come from diverse backgrounds and often juggle multiple responsibilities—they’re hustling to succeed. We aim to equip them for success while recognizing that the workplace may not be necessarily built for them (yet). Companies need to adapt, welcome, and support this next generation of talent.
With five generations active in the workforce, Millennials and Gen Z being the most diverse in history, and with the U.S. projected to become predominantly diverse by 2045, representation needs to be in your business strategy.
Supporting the career development of diverse talent involves effective leadership and creating an environment where everyone can thrive. A common misconception is that simply placing individuals in managerial or leadership roles is enough—but this isn’t true. Leadership requires compassion, courage, and the ability to adapt. Managers need to be able to give and receive feedback, lead with curiosity and empathy, have a growth mindset, and create an environment where everyone feels valued and connected.
For those in the tech industry who want to increase access and representation in their companies, partnering with organizations like Hack.Diversity allows companies to take measurable strides toward diversity and belonging.
I observe there is sometimes tension between “social impact,” “ESG,” “DEI” and “business profit.” Do you have any hot takes here or any myths you’d like to debunk about that tension?
There is no business profit problem unless you have a strategy issue. Good ESG and DEI practices, as well as practices aimed at making an organization more sustainable, have everything to do with a company's profitability and long-term success. The challenge arises when these practices are done wrong and without a clear business imperative. When this happens, people may view them as an add-on or an extra thing they have to do that competes with the company's goals.
Another misconception is that bringing in diverse thought processes is just about bringing in people to reflect your community. It's not about that; it's about understanding that you, as a business, have the opportunity to have a diverse perspective.
What’s often not discussed is that managing diverse talent requires you to be a better leader. Many of these programs fail because people don’t have the ability to manage different perspectives, navigate ambiguity, and embrace differences. Instead of fostering a growth mindset, there’s often a tendency to try to change others’ minds.
One of the biggest, cruelest myths out there is that there is a conflict between profit and these programs. For example, if you're a paper company and you're talking about ESG and sustainability, wouldn’t you want to make sure that you have trees for the future? Similarly, if your company looks at the demographics and realizes that by 2045 the country will predominantly look like me, wouldn’t you want to know how to talk to the demographic you’re trying to serve so that you can continue being in business?
You’ve mentioned your greatest pride and accolade being called Erick, Cristina, and Lorraine’s mom. What have they taught you, and what is the world you want them to experience?
My kids have taught me the meaning of love, perseverance, and humility. They’ve shown me that it’s okay not to be 100% certain about everything because there are always better and different ways of doing things. They’ve made me a much better person.
Had I not had my son, I don’t think I would have overcome homelessness. Having my daughters opened up a different compartment of my heart. I tell my kids that they each had a key that unlocked something new in my heart that I didn’t understand I had.
With Erick, I learned deep levels of compassion and understanding without judgment.
With Cristina, I learned the power of silence and that I could not be the same parent to each kid because their needs are so different. I also learned the power of wisdom—she’s so wise.
With Lorraine, I learned how to understand her freedom and the power she brought within her. Her spirit is so much like mine, but she has so much more sparkle that we see the world from a completely different lens and that’s okay.
And when I think about the world I want to leave behind, I want it to be one where everyone is accepted, regardless of our differences—regardless of how we think, who we love, and the color of our skin. I want to make sure that there is a light of love, kindness, and acceptance when I’m done.
FINAL QUESTION: We like the idea of ending our episodes with a challenge for the listeners/readers. Whether it be reaching out to an old friend, reading 5 pages a day from a book, creating a new healthy habit… What is one challenge you have for the listeners?
Give yourself five minutes of total silence every day! Even if it’s just when you first wake up in the morning, recognize that it’s a new day and ask yourself what you’ll be grateful for today.
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