Cliff Boro is the CEO of Pattern Pulse Capital, a quant hedge fund that uses sophisticated algorithms to identify patterns in vast open-source data sets to trade the futures markets. His career began on Wall Street as a high school trader, working under hedge fund legends Michael Steinhardt and George Soros. At Steinhardt Partners, Cliff developed real-time financial reporting systems, collaborating with talented programmers and sparking a passion for building software solutions to solve real-world challenges.
As an entrepreneur, Cliff co-founded and served as CEO of Infogate, a pioneering data aggregation platform, until its acquisition by AOL Time Warner. He later co-founded KidZui, the celebrated browser and search engine for children, which earned him the White House Champion of Change Award in 2011 and was sold to Saban Brands in 2012. Cliff is also proud of his role in helping founders and teams launch impactful ventures, including contributing to the founding of 6Sense, now valued at over $5 billion.
Renowned for his strategic vision and leadership, Cliff has founded, scaled, and successfully exited multiple companies, consistently demonstrating his ability to merge technology with impactful business solutions
In addition to his professional achievements, Cliff serves as President of Congregation Beth El in La Jolla and is a board member of Unscripted Learning, a nonprofit that uses improv comedy techniques to empower teenagers on the autism spectrum and seniors. His career is marked by a commitment to innovation, mentorship, and meaningful contributions to the community.
Recognized as a White House Champion of Change in 2011, Cliff’s insights have been featured in major media outlets, including The Wall Street Journal, The New York Times, and CNN. In his current role as CEO of Pattern Pulse Capital, Cliff is continuing his legacy of innovation and impact.
An avid sailor and adventurer, Cliff draws inspiration from the sea, the works of Stephen Sondheim, and the entrepreneurial spirit instilled by his father.
What is your typical day, and how do you make it productive?
I spend many nights living aboard my sailboat in San Diego Harbor. Each morning, no matter how I truly feel, I open the main hatch, step outside, and greet the world with a loud, “Good morning, world—I am undaunted!” This ritual grounds me in gratitude and sets a positive tone for the day. I take a moment to appreciate the beauty around me—the harbor, the sky, the simple joy of being alive—and carry that sense of appreciation into everything I do. It reminds me to stay focused and energized, no matter the challenges ahead.
How do you bring ideas to life?
One of my favorite artists, the legendary composer and lyricist Stephen Sondheim, captured the essence of creativity in Sunday in the Park with George. He wrote, “Having just a vision’s no solution; everything depends on execution.” I once had a 10-foot sign of that quote in my office as a daily reminder.
Bringing ideas to life requires more than inspiration—it demands passion, compelling storytelling, collaboration, and sheer grit. Passion fuels the journey, storytelling makes others believe, collaboration turns vision into action, and grit ensures you push through challenges. It’s this combination that transforms vision into reality.
What’s one trend that excites you?
It has to be AI. I’ve been fortunate to witness transformative revolutions like the personal computer, the rise of the internet, and mobile technology—and now, to experience the profound impact of AI. While my business focus is on how AI is revolutionizing trading and investing, it’s clear that this technology will reshape virtually every industry and human endeavor. It’s an extraordinary time to be part of this era of innovation.
What is one habit that helps you be productive?
I am an erratic meditator. I attend a weekly meditation group and aim for daily practice, though with mixed consistency. Ironically, when faced with an overbearing and intimidating to-do list, the best strategy I’ve found is to stop and do nothing for a moment. There’s something almost magical about realizing—on a visceral level—that the world will keep turning even if I’m not actively managing it. This perspective helps me put my to-do list and life in context, allowing me to find enough serenity to focus on what truly matters.
What advice would you give your younger self?
If I had a time machine to revisit my younger CEO journey, I’d first express appreciation for my tenacity and grit. But I’d also remind myself that it’s perfectly okay not to have all the answers. I’d urge my younger self to embrace a more scientific approach to building startups—experimenting, iterating, and learning rather than clinging too tightly to initial assumptions. I’d emphasize the importance of humility, even when it comes to core convictions about the business. Being open to not knowing creates space for better decisions and growth.
Tell us something you believe almost nobody agrees with you.
While I am a proud capitalist, I believe that the forces of the market have overshadowed the forces of citizenship in America. Too often, we relate to one another as producer and consumer, or employer and employee, rather than as equals and fellow citizens. Social media has amplified divisions by class and fueled envy, eroding our sense of collective good. I think we are at our best when united by shared purpose and mutual respect. Perhaps more people agree with me than I realize, but I often find myself reflecting on these dynamics more deeply than most.
What is the one thing you repeatedly do and recommend everyone else do?
I am an active member of the Jewish community in San Diego. Although I don’t consider myself particularly pious or devout, I attend Friday night services every week. There’s something profoundly restorative about the concept of Shabbat (the Sabbath). After a week of work and toil, you simply stop. You set everything aside to focus on family, friends, community, and introspection. It’s a practice of hitting the reset button, and I recommend everyone find their own version of this pause—it’s transformative.
When you feel overwhelmed or unfocused, what do you do?
This is an easy one because I was feeling both overwhelmed and unfocused just this morning! Despite having a daunting to-do list, I booked a Thai sports massage, left the office, and prioritized taking care of myself. It might seem counterintuitive, but we’re human beings, not machines. To perform at our best, we need to nurture ourselves first. Stepping away to recharge often brings clarity and renewed focus.
What is one strategy that has helped you grow your business or advance in your career?
Building relationships with strong mentors has been a cornerstone of my growth. I highly recommend seeking mentors who are not only smart and experienced but also genuinely kind and invested in your overall well-being. I’ve been incredibly fortunate to have mentors who believed in me and supported me through both triumphs and challenges. Their guidance has not only shaped my business decisions but also helped me navigate the broader complexities of life, enabling me to grow in every sense of the word.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Choosing just one failure is tough because I’ve experienced several startups that didn’t succeed. Early in my career, my self-worth was entirely tied to how my business was doing, which made those failures brutal. On one hand, taking my business personally fueled my determination and grit; but over time, I learned a crucial lesson: I am not my business. Life has a way of teaching perspective. Losing loved ones to death, as painful as it is, has been a profound teacher. It has reminded me that while business setbacks can feel monumental, they’re small in the context of life’s bigger picture. This perspective has helped me grow stronger and approach challenges with resilience and gratitude.
What is one business idea you’re willing to give away to our readers?
“Plastics.” For those who don’t know, that was the famous career advice line from The Graduate. Since I was born and raised in Leominster, Massachusetts—a global leader in plastics production—I couldn’t resist the reference.
On a more serious note, I see incredible potential in building an AI platform designed to help people manage their lives more effectively. Imagine telling your virtual assistant your goals and dreams, and having it serve as a constant guide to keep you on course. This platform would help align your time with your priorities, ensuring you focus on what truly matters. It’s about creating a personal “true north” compass powered by AI.
What is one piece of software that helps you be productive? How do you use it?
I’m always on the lookout for tools that help maximize my time and streamline my life. My latest discovery is Akiflow, which I use to implement the David Allen Getting Things Done system. Akiflow integrates multiple inboxes into one centralized collection point, which simplifies task management. Its standout feature, though, is how it pushes you to calendar your tasks and projects. By turning my to-do list into a structured schedule, I’ve been able to stay more focused and productive.
What is the best $100 you recently spent?
As I mentioned earlier, I recently treated myself to a powerful Thai sports massage. Although it cost a little over $100, it completely reset my day and recharged my soul. It was a reminder of the importance of investing in self-care, even when the to-do list feels overwhelming
Do you have a favorite book or podcast from which you’ve received much value?
My guilty pleasure is the Howard Stern Show. While I also listen to many serious podcasts and am an avid reader, the Stern show brings me an immense amount of joy. Instead of starting my day with news that might stress or bum me out, Howard’s humor makes me laugh, and his interviews are surprisingly insightful. Early in my entrepreneurial journey, I took myself far too seriously. Howard’s show has been a perfect counterbalance, reminding me of the importance of humor and not taking life too seriously.
What’s a movie or series you recently enjoyed and why?
My partner and I recently binged The Ozarks, and we absolutely loved it. The writing, acting, and intensity are exceptional. The lead character’s journey of building a high-stakes “startup” funded by a fictional cartel adds a wild twist to the entrepreneurial grind. It definitely puts working with venture capitalists into perspective!
Key learnings:
- The Power of Perspective: Success and failure are both part of the entrepreneurial journey, but true growth comes from separating personal identity from business outcomes and embracing life’s lessons, including those from loss and challenges.
- The Importance of Self-Care: Taking time to recharge—whether through meditation, a massage, or observing the Sabbath—can provide clarity and focus, even in the face of overwhelming demands.
- Mentorship Matters: Surrounding oneself with kind, supportive mentors who care about personal and professional well-being is a critical factor in achieving sustained growth and resilience.
- The Role of AI in Innovation: Artificial intelligence is transforming industries, including trading and investing, and its potential to enhance productivity and align personal goals with life priorities is enormous.
- Balancing Work and Joy: Humor and entertainment, such as the Howard Stern Show, can provide much-needed levity and perspective, helping entrepreneurs avoid taking themselves too seriously while navigating high-pressure careers.