Design Thinking: Rob Bolt’s Proposition for Puerto Rico’s Public Education System

Education was never part of Rob Bolt’s career plan. But after decades in the technology space, an unexpected pivot took him into the classroom, a place he ironically recalls hating as a kid.

That is what he told Alberto Bacó Bagué, host of the El Blueprint podcast, where the two talked about Bolt’s unique upbringing, his successful career in entrepreneurship and technology, and his dive into education.

“My parents had a voracious curiosity for understanding the world. They were bohemians, we traveled frequently, and I think that’s where it all started,” Bolt said.

Bolt’s journey has taken him to very different places, including Australia, Silicon Valley, India and now Puerto Rico, where he founded the Center for Design Thinking and Innovation in Education (CDTIE), an organization that brings design thinking into the island’s public schools as an educational tool.

Bolt spent roughly two decades in technology, working across software engineering, product management and entrepreneurship. His career included positions at Oracle and the launch of several tech ventures, among them Wallop Software, a Silicon Valley company he co-founded and led as CEO.

By Bolt’s account, Wallop, which developed software for corporate intranets, attracted backing from the Java Fund of venture firm Kleiner Perkins, a $100 million vehicle created in 1996 to invest in Java-based companies, during the dot-com era. Bolt eventually left the technology sector after several exits, trading a career built around software and entrepreneurship for one in education, something he never saw coming.

“I didn’t like school. I was always bored in the classroom. It was the place I least liked,” he remembers.

It is a study in contradiction for someone who became an educator, but it is also a testament to how important real-world experience is in early education and formation. Bolt remembers learning from his travels with his parents. Perhaps an even bigger influence was his father’s own career.

For an island that is developing, or at least aspiring to, a greater reliance on entrepreneurship as a career path, adopting design thinking across the education system could prove critical.

His father developed a technological process capable of pinpointing the epicenter of earthquakes, the same kind of process that can be used to determine where atomic explosions are taking place around the world. The technology drew the interest of the U.S. military, and his father came to be regarded as a person of interest. Bolt learned about this only later in life, but his father’s innovations struck him at a young age and instilled a curiosity that would eventually carry him through all of his endeavors.

Is design thinking Puerto Rico’s saving grace?

It should come as no surprise, therefore, that Bolt would later lead the implementation of a human-centered, problem-solving methodology that encourages students to identify real-world challenges, develop potential solutions, test their ideas and refine them through experimentation.

He believes in this methodology because it’s what shaped him, not only as an entrepreneur in the technology industry but also as a leader in education in a place with a different culture and language.

The island connection began while Bolt was on staff at Design Tech High School, a high school housed on Oracle’s campus in Redwood City, California. He pitched a student trip to Puerto Rico, and 12 students traveled to Bayamón to run design thinking workshops at Escuela Francisco Manrique Cabrera, a public school. CDTIE, founded in early 2018, grew out of that exchange.

Seven years after his arrival in Puerto Rico, CDTIE has expanded its work across the island through school-based design thinking programs, teacher certifications and leadership training. Its initiatives have included partnerships with UPR Bayamón and the Puerto Rico Department of Education, as well as programs that replace portions of traditional classroom instruction with hands-on design challenges, mentorship and career exploration.

In a system where the original assignment might have been to read a chapter on environmental sustainability and take a test, a design-thinking assignment could instead be to come up with a way for the school to dramatically reduce the waste it generates.

That kind of methodology creates leaders instead of test takers. For an island that is developing, or at least aspiring to, a greater reliance on entrepreneurship as a career path, adopting it across the education system could prove critical.

Entrepreneurship as a way out

Small businesses are already the backbone of the private economy. According to the U.S. Small Business Administration’s 2025 profile of Puerto Rico, which draws on 2022 Census data, small businesses (firms with fewer than 500 employees) accounted for 51.3% of private-sector payroll, totaling roughly $11.4 billion. They employed 407,296 people, or 56.9% of private-sector employees, and made up 98.4% of the island’s employer firms. That measure captures how much the private sector depends on smaller companies, not how many of them are new.

Bolt pitched a student trip to Puerto Rico, and 12 students traveled to Bayamón to run design thinking workshops at Escuela Francisco Manrique Cabrera, a public school. CDTIE, founded in early 2018, grew out of that exchange.

On the start-up side, Puerto Rico’s Department of Economic Development and Commerce (DDEC) reported that self-employment reached a record 215,000 people in November 2025, alongside record private-sector employment of 767,400. The DDEC explicitly characterized the self-employment figure as evidence of increased entrepreneurial activity.

The University of Puerto Rico’s Global Entrepreneurship Monitor (GEM) tells a similar story, with a twist. In 2013, just 8.3% of the island’s adult population was involved in early-stage entrepreneurial activity. By 2023 that share had risen to 22.3%, and in 2024 it reached 24.3%, nearly three times the 2013 rate.

But the latest GEM edition, published in August, shows the rate retreating to 15.6% in 2025. Researchers described the drop as part of a broader stabilization after the recent surge, and the rate remains nearly double its 2013 level.

GEM’s findings also point to why so many islanders start businesses. Seven in 10 early-stage entrepreneurs said a shortage of employment opportunities was a reason for launching their venture. In other words, much of Puerto Rico’s entrepreneurship is born of necessity, and schools are where the gap shows.

GEM’s assessment of the island’s entrepreneurial ecosystem rates entrepreneurship education at the school level at just 2.4, well below the 5.3 it gives to post-school entrepreneurship education, the island’s highest-rated framework condition.

That is the opening for an education that is more experiential than traditional, where assignments and exams go beyond memorization and instruction. It could help foster an entrepreneurial mindset from a young age and show Puerto Rican students the many options they have as potential careers.

CDTIE’s track record

The center that Bolt founded is doing just that. When UPR Bayamón signed an agreement with CDTIE in June 2021, the two reported that at Escuela Francisco Manrique Cabrera, where the program began, attendance had improved 35%, the graduation rate had risen 5% and student motivation had grown 24% between 2018 and 2019.

The agreement extended the program to Academia Espíritu Santo in Levittown. At the time, CDTIE said it had reached about 1,200 students, more than 60 educators and more than 100 community members.

In March 2025, the center began its third Educator Fellows cohort, comprising 18 graduates of its Design Thinking in Education certification program as well as graduates of a leadership academy. The program focuses on applying principles such as experimentation, collaboration and action to education.

Today, Bolt continues to take part in conversations about the challenges and opportunities facing Puerto Rico’s education system.

To learn more about how he redesigned his own definition of success and turned childhood experiences into the engine that drove his later-in-life career, tune in to this episode of El Blueprint, available on YouTube and Spotify and linked above.