Blue Ocean Global Technology Interviews Jay Garside | Investor Relations and Ambassador of THE REAL Mental Health Foundation

Jay Garside is an investor relations leader with a talent for raising capital, expanding investor networks, and building genuine relationships with every LP he meets, whether they invest with him or not.

Raised in a multi-generational family of entrepreneurs, Jay grew up surrounded by business builders. His father, grandfather, and uncles all started, scaled, and sold companies or took existing platforms and turned them into something greater. From an early age, he was hands-on in that world, observing how bold decisions and strong relationships could shape real outcomes. Jay learned early that lasting success comes from taking decisive action in one direction while staying open to constant improvement. For him, progress is built on iteration, consistency and trust.

Jay began his career in competitive B2B sales, where he became a nationally recognized President’s Club top performer, consistently exceeding targets and leading high-performing teams. Those experiences taught him that relationships drive long-term results.

When he moved into venture capital, Jay quickly made his mark. Within months, he had raised millions, sourced new deals alongside top venture firms, and hosted investor events that fostered genuine connection. Known for his creativity and follow-through, he has a way of making investors feel part of something larger than a transaction — a shared vision and community built on trust. 

Today, Jay brings together his entrepreneurial roots, sales expertise, and relationship-focused mindset to help families and investors access new opportunities across asset classes and build partnerships that last.

Blue Ocean: Could you tell us about your professional journey— what inspired you to pursue a career centered on building relationships and creating opportunities for others?

Jay Garside: I grew up surrounded by entrepreneurship. My dad, grandfather, and uncle all started, scaled, and sold businesses or bought into existing platforms to build something greater. From a young age, I was immersed in that world, learning how businesses actually operate and how important it is to focus on the people within.

One of my earliest memories is my grandfather telling me, “Jay, if you want to be a good entrepreneur, you have to get good at sales.” That stuck with me. I have dyslexia, so school was challenging, and sales became my outlet. I had tutors through middle school, high school, and college. I knew I might not outsmart everyone in the room, but I sure as hell would outwork them—and that mentality has stayed with me.

After graduating from college at the University of Colorado Boulder, I had friends doing incredibly well in B2B enterprise software sales. They encouraged me to try it, and I jumped right in. I quickly became a President’s Club top performer at every company I worked for, whether at publicly traded companies, private equity portfolio companies, or early-stage growth businesses.

Over time, I led go-to-market efforts for an early growth-stage SaaS company to help them penetrate the U.S. market, and more recently, I made the pivot into venture capital. I’ve never applied for a job in my life; every opportunity came from proactively reaching out, creating value, and showing people why they should work with me. That mindset led me to my current role in Southwest Florida, where I’ve been shaping the next chapter of my career.

Blue Ocean: What does a typical day look like for you as someone who balances investor relations, community building, and personal purpose?

Jay Garside: My day revolves around relationships and community building. It’s never really about me, it’s about the people I interact with. Every conversation is a chance to inspire, to make an impact, or to learn something new.

I live by the principle of reciprocity. Each morning, I take care of my personal tasks, then shift my focus entirely to others. Whether it’s a lunch, a Zoom call, or a quick catch-up, I leave each conversation by asking, “How can I be helpful to you?” From there, I look for ways to connect people and create value. It’s not about me.

Blue Ocean: Which emerging trends in your industry excite you the most?

Jay Garside: One major trend I’ve seen at events, conferences, and meetings with family offices and high-net-worth individuals is the growing allocation toward private alternatives.

The number of public companies has dropped by nearly half over the past couple of decades, so now it is all about access. During COVID, we were all tucked away in our homes, but now, getting access to the best opportunities means being out there—meeting people, understanding asset classes, geographies, return profiles, and investment structures, and aligning them with your goals or those of the families you work with.

Blue Ocean: What do you believe has been the key to your success in creating trust and authentic partnerships?

Jay Garside: For me, it all goes back to my grandfather’s principle of reciprocity. It’s never about one-sided gain. The key is being genuinely curious and truly caring about the people you interact with. Regardless if they can help me or not.

I believe that you can inspire, impact, or help everyone you cross paths with, in any way, shape, or form—whether that’s through making a connection, sharing knowledge, or offering a fresh perspective. The real differentiator is consistency: showing up with that same mindset every single day, with every person you meet. Actually following through.

Blue Ocean: In your view, what is something unique you bring to your clients and communities?

Jay Garside: It might sound simple, but for me, it’s hustle. And not just for my own benefit. It’s about following through for others. If you say you’ll do something, you need to do it. People remember that.

The most successful people I’ve met always emphasize that you have to help others out in ways outside of what you do. When you consistently follow through and do what you say, what goes around comes around, and good things will happen.

Blue Ocean: From your experience, what qualities set apart people who thrive at building meaningful relationships from those who don’t?

Jay Garside: A big part of it is listening to what people aren’t saying. And what they ‘aren’t’ saying. Pay attention to body language and the flow of a conversation—if something feels off, it probably is. Call it out and get them talking about themselves. 

I’m very direct, which comes from my mom’s side—they’re from Greenwich, CT. If I sense a disconnect, I’ll ask, “Are you okay? How are you really? How are the kiddos?” Everyone has something going on, and it’s important to really try to understand what’s in their head, even if they don’t say it outright.

People love to talk about themselves. If you can get them to open up about what’s truly on their mind, you build a real connection. Then it’s about following through, showing up, being helpful, and doing the right thing. It’s never about me; it’s about genuinely being there for others.

Blue Ocean: How do you approach mentoring or guiding others who want to build purpose-driven careers?

Jay Garside: I’m still young, and I have plenty of mentors myself. Mentorship, to me, goes both ways. When someone reaches out, whether it’s my younger brother’s friends or former colleagues in enterprise SaaS, I try to understand what their real questions are. 

I help them think through things in a way that helps them make sense for them, because not everyone thinks the same way I do. I ask what’s worked for them, what hasn’t, and then share my own experiences and how I’d approach it if I were in their shoes. But it’s important to tailor that to who they are as individuals.

Blue Ocean: As an ambassador for THE REAL Mental Health Foundation, how do you integrate mental health, purpose, and lifelong learning into your professional life?

Jay Garside: For me, it really comes down to empathy. Everyone has something going on in their life at any given moment. You can be the happiest person in the world one minute, and one phone call can change everything.

Understanding that, and genuinely listening, not just to respond but to truly understand, is how I integrate mental health into my daily life. I’ve had a therapist my whole life, not because I needed it, but because I think it’s healthy. Everyone needs a space to get things off their chest. We all love to talk about ourselves.

As for purpose and lifelong learning, I’m still figuring it out. It’s a forever work in progress. I read a lot of psychology and personal development books from people like Brian Tracy, Zig Ziglar, and Dale Carnegie, and I revisit those classics often. They keep my emotional intelligence sharp and remind me of the fundamentals.

There’s so much noise in the world today, and going back to timeless principles keeps me grounded.

Blue Ocean: What is something you are most grateful for, either professionally or personally?

Jay Garside: I’ll start with the most important one—my fiancée, Chloe. She’s the sweetest person in the world, my biggest supporter, and my biggest cheerleader. She gives me confidence even when I don’t have it myself. She truly brings sunshine to everyone’s day. I’m also very grateful for my mom—I’m a bit of a mama’s boy. She and Chloe are actually very similar.

Professionally, I’m most grateful for the relationships I’ve built over the years. I’ve been fortunate to connect with remarkable entrepreneurs and executives who are firmly in my corner. I can call them any time, and they’ll always give it to me straight.

Blue Ocean: What’s one lesson in life that changed your perspective?

Jay Garside: One big lesson I’ve learned is to really know who you’re doing business with before you do business with them. Whether it’s taking a job from an employer, bringing on a client, working with an investor, or entering any kind of professional relationship, quality over quantity matters. 

Once you’re in business with someone, you’re tied to them for an indefinite period, and you need to know who they are and what they stand for. It’s crucial to understand their values, character, integrity, and authenticity. If those don’t align with yours, every conversation will feel off, and the relationship won’t last. 

When you’re just starting out, it’s easy to get caught up in the excitement of new opportunities, but taking the time to vet people carefully and make sure there’s alignment is critical.

Blue Ocean: Is there a particular quote or piece of advice that has guided you through your career?

Jay Garside: Since I am in sales and capital formation, one quote has always stayed with me: “All it takes is one conversation. One conversation can change your life.” I’m not sure where it came from, but I live by it. You never know where a single conversation might lead—who someone knows, what opportunities might come from it, or how it might shape your path in unexpected ways. That is the beauty of business.

Blue Ocean: What hobbies or interests help you maintain a balanced lifestyle outside of work?

Jay Garside: I grew up in Southwest Michigan, in the Gull Lake area, and duck hunting has always been my favorite thing in the world. I grew up hunting duck, geese, and turkey —really all kinds of waterfowl. My family has property in Michigan, so that was a big part of my life.

Since moving to Naples, Florida, I’ve been finding new hobbies. I grew up playing all kinds of sports—hockey, soccer, tennis, golf—and spent a lot of time on the lake, wakesurfing and being outdoors.

These days, my fiancée and I love going to the beach, enjoying good food, and making the most of our weekends together. We both work hard during the week, so quality time together is how I recharge.

Conclusion

Jay Garside’s journey is rooted in entrepreneurship, resilience, and genuine human connection. From growing up in a family of business builders to becoming a top sales performer and later stepping into venture capital, his path has been driven by hustle, reciprocity, and a belief in the power of a single conversation to change everything. In both business and life, Jay believes it’s never about you — it’s about the people you uplift along the way.