Michelle De La Isla doesn’t talk like someone who’s had an easy runway. She talks like someone who’s had to claw for every inch—then turned around and built a ladder for other people. In a live conversation recorded at Startup Boston Week, the former Topeka mayor (and now CEO of Hack.Diversity) laid out a life story that’s part grit, part community rescue mission, and part straight-up refusal to accept the “that’s just how it is” story that keeps underrepresented talent out of tech.
From survival mode to “bridge builder”
De La Isla’s background reads like the kind of thing people reduce to an inspirational tagline—except she doesn’t let you do that. Born in New York City, raised in Puerto Rico, she describes being homeless at 17, becoming pregnant at 19, and being diagnosed with cancer at 22.
What jumps out isn’t just the hardship. It’s the recurring theme: somebody stepped in before the story ended badly. She points to a supportive church community in Puerto Rico that helped send her to college in Kansas.
It took eight years, but she earned a bachelor’s degree from Wichita State University, then joined Upward Bound—where, in her words, she realized she wanted to create opportunities for others the way mentors had done for her.
That “pay it forward” instinct becomes the throughline for everything that follows: higher education teaching, nonprofit finance, city leadership, and now a tech-talent pipeline role that’s basically built for her worldview.
The resume looks zig-zaggy. The mission doesn’t.
If you’re a hiring manager skimming LinkedIn, her path might look like a curveball: Biology instructor at Butler Community College, CFO at a housing and credit counseling nonprofit, Mayor of Topeka, congressional run, Harvard, then CEO of a diversity-focused tech pipeline organization.
But her logic is pretty coherent: she’s been inside systems that routinely shut people out, and she’s collected pattern recognition from each one.
Here’s the career arc as it’s described in the conversation and episode framing:
| Chapter | Role/Work | What it trained her to see |
|---|---|---|
| Education | Biology instructor (Butler CC) | Who gets support, who gets “weeded out,” and how confidence gaps form early |
| Community development | CFO, Housing and Credit Counseling, Inc. | How money stress and housing instability quietly wreck career momentum |
| Government | Mayor of Topeka | How institutions respond under crisis, and who pays the price when trust collapses |
| National politics + policy lens | Congressional run; later Harvard focus on bridge building | How disagreement becomes paralysis—and why “translator” leadership matters |
| Tech workforce pipeline | CEO, Hack.Diversity | Turning all of the above into a system that actually places and supports talent |
What she says was hardest as mayor (and why it matters for tech)
Her toughest moments in office weren’t “budget season” stress. They were trauma-at-scale moments.
She recalls taking office just a month after Dominique White, a Black man, was shot by two white officers—then having to navigate threats, fear, and the real work of helping a city heal while being the first Afro-Latina elected to the job.
Then came the timing trap: she announced in January she wouldn’t seek reelection and would run for Congress; COVID hit in March. That meant she was managing a public-health emergency while also running a federal campaign. She describes the role as being a “translator,” getting accurate information to residents while people had wildly different opinions and emotions running hot.
That word—translator—isn’t random. It maps cleanly onto what diverse talent often faces in tech: you’re not just doing the job, you’re decoding the room, learning the unwritten rules, and figuring out how to “manage up” without getting labeled difficult.
Hack.Diversity’s bet: placement is only step one
One thing De La Isla is pretty direct about: “just place them in jobs” is not a strategy. It’s a checkbox.
She explains that Hack.Diversity’s Fellowship focuses on internship and industry readiness—things that don’t show up on a coding assessment but determine whether someone survives their first year in a professional environment. That includes growth mindset, managing imposter syndrome, navigating workplace dynamics, and managing up.
And she points out the obvious-but-rarely-said thing: many workplaces weren’t built with these Fellows in mind “yet,” and companies have to adapt if they want to keep the talent they claim they want.
A quick snapshot of the “beyond placement” supports she describes:
| Support area | What it looks like in practice | Why it changes outcomes |
|---|---|---|
| Confidence + psychology | Imposter syndrome tools, growth mindset training | People stop self-selecting out when they hit the first rough patch |
| Workplace navigation | Managing up, reading team dynamics | Fewer avoidable misfires with managers and expectations |
| Leadership readiness (for companies) | Managers learning curiosity, empathy, feedback, adaptability | Retention improves when the environment isn’t quietly hostile |
| Partnerships | Host-company relationships (she name-checks AWS, Liberty Mutual, Rapid7, Wayfair, others) | Creates repeatable hiring lanes instead of one-off “pilot” programs |
If you want a broader policy context for why workforce inclusion keeps showing up as a national economic theme, the U.S. Department of Labor is one useful starting point (https://www.dol.gov). And when the conversation turns to demographic change, the U.S. Census Bureau is the obvious official reference point (https://www.census.gov).
Her hottest take on “DEI vs profits”: that’s a strategy problem
This is where she gets spicy—without doing the corporate TED Talk thing.
De La Isla argues there’s “no business profit problem unless you have a strategy issue.” In her framing, ESG and DEI aren’t opposed to profitability; they’re supposed to be tied to long-term sustainability. The real failure is when companies run these efforts as an “add-on,” with no business imperative, and then act shocked when the org treats it like busywork.
She also goes after a quieter myth: that diversity is just about optics. She says it’s about diverse perspective—and that managing diverse talent forces leaders to actually become better leaders (compassion, courage, growth mindset, feedback skills). Programs fail, she suggests, when managers can’t handle ambiguity or difference and default to trying to “change others’ minds” instead of building an environment where multiple perspectives can operate.
If you’re looking for the U.S. government’s angle on workplace discrimination and equal opportunity (the stuff that turns into lawsuits when mishandled), the EEOC lays out enforcement and guidance here: https://www.eeoc.gov. And for companies trying to understand what “fair labor” expectations look like at a baseline, the DOL’s wage and hour resources are here: https://www.dol.gov/agencies/whd.
The personal anchor: her kids, and the world she wants next
Near the end, she gets candid about what she’s proudest of: being “Erick, Cristina, and Lorraine’s mom.” She talks about how each child taught her something different—compassion without judgment, the power of silence and wisdom, the freedom to see the world differently.
And the future she describes isn’t framed as a policy platform. It’s emotional: a world where people are accepted regardless of differences—how we think, who we love, and the color of our skin.
Her closing challenge is almost comically simple, which is probably why it sticks: give yourself five minutes of total silence every day. Wake up, notice it’s a new day, and decide what you’ll be grateful for.
That’s not a productivity hack. It’s a survival habit. And honestly, it fits her whole story: when life is loud, you create space to hear yourself again.
FAQs
1. Who is Michelle De La Isla?
She’s the CEO of Hack.Diversity and previously served as Mayor of Topeka; she’s also worked in higher education and nonprofit community development.
2. What is Hack.Diversity focused on?
Connecting underrepresented talent with meaningful opportunities in tech, including readiness training and partnerships with host companies.
3. What challenges did she describe from her early life?
She described being homeless at 17, pregnant at 19, and diagnosed with cancer at 22, alongside community support that helped her reach college.
4. What does she think companies get wrong about DEI/ESG and profit?
She argues the tension is largely a strategy issue—programs fail when treated as add-ons without a business imperative and when managers aren’t equipped to lead diverse teams.
5. What’s one actionable thing she challenged listeners to do?
Take five minutes of total silence daily and start the day by naming what you’ll be grateful for.
