Introduction:

In this episode of Director or Detour, I sat down with Brian Aleksivich to unpack the non-linear path I’ve taken from studying entrepreneurship and theater, to leading technology at the LA Clippers and United Talent Agency, and now serving as an advisor, builder, and founder in the venture and AI space. We talked about how I’ve blended business instincts with a love for tech, what “empathetic innovation” really means, and how I’m using those principles to build tools that empower other entrepreneurs—especially those outside the traditional tech bubble. This is a conversation about failing forward, innovating with purpose, and learning how to make big moves, even when the path is anything but straight.

Key Topics I Covered:

Blending Business Instincts with Tech Curiosity

I didn’t start out as a coder or an engineer. My roots were in entrepreneurship and creativity. But I discovered that what made me effective wasn’t deep technical expertise—it was my ability to communicate across silos. I learned to speak both tech and business fluently, and that made me valuable. Whether I was troubleshooting systems or building out new ideas, my strength came from being able to translate between disciplines and make solutions approachable.

Empathetic Innovation and the Role of the CTO

At the Clippers and UTA, my job as CTO wasn’t just to build systems—it was to connect technology to real-world outcomes: improving player performance, enhancing fan experience, and streamlining operations. I coined the phrase “empathetic innovation” to describe how I approach tech—not from a place of jargon and fear, but by helping people understand how tools can actually make their lives better. It’s about being a translator, not a gatekeeper.

Build Fast, Break Smart: How I Think About Tools and Scale

One of my big takeaways from running tech at high-profile organizations is that simplicity wins. You don’t need overly complex stacks. You need solutions that are scalable, agile, and replaceable. For entrepreneurs and small business owners, I always advise: think agnostically, don’t lock yourself into tools too tightly, and always leave room to pivot. Whether you’re using Zoho, Google, or open-source systems, the goal is to build frameworks that can evolve with you.

From Funder AI to Investimate: Enabling the Next Wave of Founders

After stepping away from corporate leadership, I built a platform called Funder AI—now Investimate—to give nontraditional founders the tools to take their ideas from napkin sketch to pitch-ready. It’s more than just a business builder. It’s a way to break down complex processes—like creating a pitch deck, branding, and market analysis—and democratize access to startup knowledge. The more I worked with both founders and investors, the more I realized the power of systems, language, and structure to unlock real opportunity.

Conclusion:

My journey hasn’t been a straight line—from entrepreneurship school to Broadway dreams, from the Clippers to UTA, and now into venture, AI, and advisory work. But what’s stayed constant is my drive to empower others through clarity, systems, and empathy. Whether I’m speaking at a conference, helping a founder land funding, or building tools that level the playing field, I’m always thinking about how to make innovation more inclusive and actionable. The detours have been just as valuable as the direct paths—and I wouldn’t have it any other way.

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