Building Painkillers, Not Vitamins: How Daniel Marashlian Scaled Drata to 700 Employees
Episode Summary In this episode of Chaos to Clarity, Eric Weiss sits down with Daniel Marashlian, Co-Founder and CTO of Drata, one of San Diego’s fastest-growing SaaS startups. Daniel shares his 20-year founder journey, from building early web systems after the dot-com crash to co-founding Drata, a company now powering compliance automation for more than […]
Scaling to $300M with Product-Led Growth
Episode Summary In this episode of Chaos to Clarity, Eric Weiss sits down with Gaurav Agarwal, COO of ClickUp, to unpack how one of San Diego’s biggest SaaS success stories built a $300M ARR business by putting product, speed, and customer obsession at the center of its strategy. Gaurav shares how ClickUp redefined product-led growth, […]
When Success Means Life or Death: Ryan Rusnak’s Journey Building Airspace
Episode Summary In this episode of Chaos to Clarity, host Eric Weiss sits down with Ryan Rusnak, Co-Founder and CTO of Airspace, one of San Diego’s fastest-growing logistics tech companies. Ryan shares how Airspace built a $100M business around time-critical shipping, moving everything from organs for transplant to parts for grounded airplanes. He reveals how […]
Building AI Startups with Andy Ballester, Co-Founder of GoFundMe and EyePop.ai
Episode Summary In this episode, Eric Weiss sits down with Andy Ballester, serial entrepreneur and co-founder of GoFundMe and EyePop.ai, to unpack the highs, lows, and lessons of building category-defining startups. Andy shares how an early college job at a software startup sparked his passion for technology, why he bootstrapped GoFundMe into a global fundraising […]
Scaling Up to $100M, with Afif Khoury, CEO of SOCi
Episode Summary Afif Khoury, founder and CEO of SOCi, joins Eric to share the inside story of scaling one of San Diego’s hottest unicorns. From the “dark era” of customer rejection to becoming the operating system for enterprise marketing, Afif reveals the hard decisions, pivotal pivots, and leadership lessons that turned chaos into a category-defining […]
Building a Thriving Startup Community with Neal Bloom, CEO of Rising Tide Partners
Episode Summary In this episode of Chaos to Clarity, host Eric Weiss sits down with Neal Bloom, Managing Partner at Rising Tide Partners and one of the most influential connectors in the San Diego startup ecosystem. From co-founding Portfolium to launching Interlock Capital and now building Rising Tide, Neal shares his journey from aerospace engineering […]
Object-Oriented Management: Architecting High-Performance Teams Like Software Systems
You’re Not Just Managing a Team. You’re Architecting a System. You’ve got a team of smart, capable people. You’ve got a roadmap. You’ve got stakeholders. So why does it feel like everything is harder than it should be? This is hard enough with one team, but as your organization grows, these problems multiply, and each […]
How to Resolve Co-Founder Conflict and Save Your Company by Stepping Out of the Frame
The Hidden Time Bomb of Co-Founder Conflict Let’s be blunt: Co-founder conflict is one of the most common reasons startups implode. Investors know it, employees feel it, and founders live it every single day. The statistics are sobering—many startups don’t fail because of bad products or lack of funding, but because the people at the […]
Why Your Team Isn’t Improving and How to Fix It With Retrospectives
You’re running into the same problems, sprint after sprint. The team keeps struggling with the same issues, but nothing seems to change. Sound familiar? Here’s the hard truth: Your team isn’t improving because your retrospectives aren’t working. A retrospective is the core mechanism of continuous improvement. If you’re running it well, your team should get […]
Learn to Lead at Scale With This Simple Core Values Framework
The Leadership Bottleneck: Why Every Decision Falls on You Many leaders—especially in fast-moving teams—feel like they have to be involved in every decision. Their teams struggle to make independent choices that align with the company’s direction, leading to bottlenecked decision-making and unintentional micromanagement. Why does this happen? Typically: The result? Leaders are forced into a […]