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 […]
REFLECTION AND IMPROVEMENT – Bringing Agile Principles To All Functions With Eric Weiss – Bonus Episode

Episode Summary Systematic self improvement and self reflection are two aspects of entrepreneurial development that often get glossed over, and historically don’t exist outside of engineering teams. Bringing these Agile principles into other departments has helped Eric’s clients reach outcomes that previously seemed unattainable.
LEVERAGE IS KEY – Growing Your Business Through Self Development With Serial Entrepreneur JJ Parker, Part 2

Episode Summary Something that most entrepreneurs learn through trial and error is the importance of leverage and efficiency. While it’s completely normal to attach yourself to every process in your company at the early stages, it’s highly inefficient to do so and will often lead you off the growth path. The sooner you learn how […]
BUSINESS MEETS ART – How To Build Multiple Successful Businesses with Serial Entrepreneur JJ Parker, Part 1

Episode Summary JJ took an unconventional path to entrepreneurship. He’s an art and design graduate who noticed a market gap in early tech back in the 90’s. Early in his career, JJ had to train school employees how to use video bulletin software, which is when he realized that the true problem behind why people […]
SQUARE PEG + ROUND HOLE – How Technical Founders Should Approach Go-To-Market with Eric Weiss – Bonus Episode

Episode Summary Many founders build their technology and only then try to figure out what industry it’s best applied to. In the case of Davit, they had 24 different use cases they were trying to present to the market, which caused them to struggle with their business model.
NEXT GEN TECH – Scale By Innovating Your Tech with David Baghdasaryan, Co-Founder & CEO of Krisp, Part 2

Episode Summary Krisp has grown significantly throughout COVID and beyond. They saw a huge market opportunity with call centers where the issue of noise cancellation is truly prevalent and expensive, which helped them grow through word of mouth. Throughout this growth spurt they’ve been able to add a plethora of new features, and now they’re […]