CLOUDBREAK

Trilogy Equity Partners
  • 5.0 (1)
  • Entrepreneurship

Welcome to Cloudbreak, where breakthrough innovation meets breakthrough growth. In this podcast hosted by early stage VC firm Trilogy Equity Partners, we sit down with the brilliant minds and leaders building early stage startups to discuss the pivotal stories, insights, and hard-won lessons they've learned from the driver's seat of breaking innovation, company building, and scaling. They'll share what's working, what isn't, and what they'd wish they'd known earlier.

Episodes

  1. Sep 23

    How Rollout Is Using AI to Give Police Officers Their Time Back

    Ted Sullivan, co-founder and CEO of Rollout, joins John Stanton of Trilogy Equity Partners to talk about his entrepreneurial journey, from his early days in professional baseball, to founding GameChanger, to now building Rollout, an AI-powered assistant for police officers. Ted shares how a cold LinkedIn message from a deputy police chief sparked the idea for the company and what he learned from riding along with patrol officers. They also discuss building with AI, staying close to customers, and understanding the problem before building the solution. (00:23) - Introduction and Ted’s background in baseball and entrepreneurship (02:00) - Ted’s journey from minor league baseball to founding Head First (03:44) - Attending business school and shifting to a tech career (06:16) - Starting Game Changer and solving youth sports problems (10:14) - The founding team and early development of Game Changer (14:21) - Fundraising challenges and persistence in startup growth (18:26) - Industry challenges: fragmentation, seasonality, and churn (20:51) - Selling Game Changer to Dick’s Sporting Goods (23:26) - Ted’s new venture: AI in law enforcement and police work (28:01) - The role of AI in modern product development (30:20) - Common mistakes founders make and lessons learned (31:07) - Influences, mentors, and the importance of grit (34:02) - Books and resources Ted is currently reading (34:50) - Predictions for the World Series and sports analytics (35:15) - Closing remarks and future plans

    How Rollout Is Using AI to Give Police Officers Their Time Back

  2. 12/17/2025

    How TestSprite's Founders Are Transforming Software Testing with AI

    In this conversation, Yunhao Jiao (CEO) and Rui Li (CTO) co-founders of TestSprite discuss their AI-powered platform for automating testing for both back-end and front-end systems. They share insights on the rapid adoption of their product, the challenges faced in software testing, and the importance of a customer-centric approach. The discussion also touches on the company's growth, hiring strategies, and the origin story behind TestSprite, highlighting the transformative potential of AI in the tech industry.

    How TestSprite's Founders Are Transforming Software Testing with AI

  3. 10/20/2025

    How Zuplo is Redefining Gateways for the AI Era

    In this episode, Josh Twist, co-founder and CEO of Zuplo, shares insights into the journey of building a fully managed API management platform. He discusses the emotional and professional motivations behind starting Zuplo, the challenges of creating a mission-critical software solution, and the importance of strategic partnerships.

    How Zuplo is Redefining Gateways for the AI Era

  4. 09/02/2025

    From Code to Community: How Open Sourcing Accelerated AI Growth

    In this conversation, Gideon Mendels, CEO and co-founder of Comet, shares the journey of building an AI observability platform from its inception in 2018, the launch of their new product Opik , and the strategic decision to open source it. He discusses the rapid growth of Opik , its features, the importance of evaluation in AI applications, and his partnership with Trilogy. As AI and machine learning become increasingly central to business operations, Comet builds tools that help teams manage any machine learning or large language model lifecycle.

    From Code to Community: How Open Sourcing Accelerated AI Growth

  5. 08/05/2025

    Beyond Screen Time Limits: BrightCanary Founders on Building Digital Safety Tools That Actually Work

    In this conversation, Karl Stillner and Steve Dossick discuss their journey in creating BrightCanary, a parental control solution that focuses on providing insights into children's digital activities rather than merely blocking content. They share their experiences as parents, the challenges of navigating the competitive landscape, and the importance of understanding customer needs. The discussion also covers the significance of building a strong company culture, the unique challenges of transitioning from B2B to B2C, and the future opportunities for their product.

    Beyond Screen Time Limits: BrightCanary Founders on Building Digital Safety Tools That Actually Work

  6. 08/05/2025

    Building Successful Startups: Vieu CTO & Co-Founder Simon Skaria on Team Dynamics That Drive Growth

    In this conversation, Simon Skaria, the CTO and co-founder of Vieu, discusses the evolution of the company, its core offerings, and the importance of team dynamics in building a successful startup. He shares insights on the origin story of Vieu, the significance of having a strong founder relationship, and the challenges of competing in a crowded market. Simon emphasizes the need for a customer-centric approach and the development of a semantic graph to enhance customer engagement.

    Building Successful Startups: Vieu CTO & Co-Founder Simon Skaria on Team Dynamics That Drive Growth
  • 6 Episodes

About

Welcome to Cloudbreak, where breakthrough innovation meets breakthrough growth. In this podcast hosted by early stage VC firm Trilogy Equity Partners, we sit down with the brilliant minds and leaders building early stage startups to discuss the pivotal stories, insights, and hard-won lessons they've learned from the driver's seat of breaking innovation, company building, and scaling. They'll share what's working, what isn't, and what they'd wish they'd known earlier.

Information

  • Creator
    Trilogy Equity Partners
  • Years Active
    2025 - 2026
  • Episodes
    6
  • Rating
    Clean
  • Copyright
    © @Trilogy Equity Partners
  • Show Website
    CLOUDBREAK