Chaos To Clarity

In this episode of Chaos to Clarity, Eric Weiss sits down with Misti Cain, the Managing Director of Techstars San Diego powered by SDSU, to unpack what makes this accelerator one of the most selective and impactful pre-seed programs in the world. With more than 1,300 applicants and only six companies selected, Techstars San Diego represents the highest caliber of early-stage founders building acro...

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 8,000 customers. He opens up about what it takes to scale f...

 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, balanced self-serve and sales-assisted revenue models, and built a culture ob...

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 the team uses AI and machine learning to optimize rout...

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 platform, and what it took to sca...

Key Takeaways Finding conviction when the market says no. SOCi was built for multi-location brands that initially rejected the idea of managing thousands of local pages. Afif explains how he stayed the course, found early adopters, and survived until the market caught up. Scaling through pressure cookers. Hyper-growth exposed broken systems, forced painful pivots, and required letting go of two-th...

They dive deep into: The evolution of the San Diego startup scene since 2013   The power of founder-led communities and grassroots events   Why curated connections matter more than vanity metrics   Lessons from Startup Week, EvoNexus, and Startup San Diego   The rise of angel investing groups like Interlock and Rising Tide Partners   Challenges San Diego faces compared to Silicon Valley and how to...

This episode continues the conversation with Jason Corso - Professor of Robotics and EECS at University of Michigan and Co-Founder/Chief Science Officer at Voxel51 - a Series A AI software company that enables machine learning and computer vision scientists to rapidly curate and experiment with their datasets in order to build higher performing machine learning systems. AI platforms have been a ga...

Today’s episode welcomes Jason Corso - Professor of Robotics and EECS at University of Michigan and Co-Founder/Chief Science Officer at Voxel51 - a Series A AI software company that enables machine learning and computer vision scientists to rapidly curate and experiment with their datasets in order to build higher performing machine learning systems. Jason is a builder by nature. During his academ...

This episode continues the conversation with Raj Verma, CEO of SingleStore - a Series F startup that provides a cloud-native database built with speed and scale to power real-time applications. Eric and Raj discuss the implications of openly available AI. On one hand, a ton of good will be brought into the world. On the other hand, every new technology comes with its caveats and even the simplest...

In this episode, Eric is joined by Raj Verma, CEO of SingleStore - a Series F startup that provides a cloud-native database built with speed and scale to power real-time applications. Raj speaks on their journey of finding the problem in their market. They saw how inefficient it is to navigate between multiple data platforms and that data is often too fragmented and spread between too many sources...

Today’s bonus episode follows the 2 part episode with Shaun Savage, San Diego based Founder and CEO of GoShare - a cloud based logistics platform that connects truck owners with businesses and individuals to provide on-demand delivery & moving services. An organisation with a high level of trust also has a high level of autonomy, which creates scalability. Once you build a culture of trust, your t...

This episode continues the conversation with Shaun Savage, San Diego based Founder and CEO of GoShare - a cloud based logistics platform that connects truck owners with businesses and individuals to provide on-demand delivery & moving services.  Shaun and Eric discuss the importance of customer interviews. Even though this activity might look inefficient on paper as it does not scale, there’s stil...

In this episode, Eric is joined by Shaun Savage, San Diego based Founder and CEO of GoShare - a cloud based logistics platform that connects truck owners with businesses and individuals to provide on-demand delivery & moving services.  Shaun’s entrepreneurial journey began when he started a house painting business with a few friends from college. One of the biggest challenges he had at the time wa...

Today’s bonus episode follows the 2 part episode with JJ Parker, a serial entrepreneur who runs Tightrope Media Systems, Carousel Digital Signage and most recently Screenweave, a company that unblocks work by empowering people to communicate asynchronously with video. Systematic self improvement and self reflection are two aspects of entrepreneurial development that often get glossed over, and his...

This episode continues the conversation with JJ Parker, a serial entrepreneur who runs Tightrope Media Systems, Carousel Digital Signage and most recently Screenweave, a company that unblocks work by empowering people to communicate asynchronously with video. Something that most entrepreneurs learn through trial and error is the importance of leverage and efficiency. While it’s completely normal t...

In this episode, Eric is joined by JJ Parker, a serial entrepreneur who runs Tightrope Media Systems, Carousel Digital Signage and most recently Screenweave, a company that unblocks work by empowering people to communicate asynchronously with video. 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...

Today’s bonus episode follows the 2 part interview with Davit Baghdasaryan, Co-Founder & CEO of Krisp - a software tool that maximizes the productivity and impact of every conversation by eliminating noise distractions,increasing the fidelity of voice communication, and transcribing and synthesizing the most relevant details and analytics from every voice interaction.  Many founders build their te...

This episode continues the conversation with Davit Baghdasaryan, Co-Founder & CEO of Krisp - a software tool that maximizes the productivity and impact of every conversation by eliminating noise distractions,increasing the fidelity of voice communication, and transcribing and synthesizing the most relevant details and analytics from every voice interaction.  Krisp has grown significantly throughou...

In this episode, Eric is joined by Davit Baghdasaryan, Co-Founder & CEO of Krisp - a software tool that maximizes the productivity and impact of every conversation by eliminating noise distractions,increasing the fidelity of voice communication, and transcribing and synthesizing the most relevant details and analytics from every voice interaction.  Davit’s background is in engineering. If you aske...

Today’s bonus episode follows the 2 part episode with Jan Arendtsz, Founder & CEO of Celigo - an iPaaS platform that simplifies the integration of business applications and data sources in the enterprise. During those two episodes, Eric and Jan discussed what it takes to truly grow a platform business. Many founders want to go after a broad market and grow their company into an industry staple. As...

This episode continues the conversation with Jan Arendtsz, Founder & CEO of Celigo - an iPaaS platform that simplifies the integration of business applications and data sources in the enterprise. In the previous part we established the story of how Celigo had to make some hard decisions that were ultimately for the best. In more recent history, they had to pivot to a new product even after they fo...

In this episode, Eric is joined by Jan Arendtsz, Founder & CEO of Celigo - an iPaaS platform that simplifies the integration of business applications and data sources in the enterprise. iPaaS stands for Integration Platform as a Service, which is a new term for an industry that’s been around since the 90s. Their predecessor was the ETL (Extract, Transform, Load) model which was led by companies li...

Today’s bonus episode follows the 2 part episode with Guillermo Rauch, CEO of Vercel - a Series D startup that provides the developer experience and infrastructure to build, scale, and secure a faster, more personalized Web.

 AI is currently disrupting how we approach building UI by increasing the speed at which we’re able to articulate an idea and build the first model. 

These prototypes also e...

This episode continues the conversation with Guillermo Rauch, CEO of Vercel - a Series D startup that provides the developer experience and infrastructure to build, scale, and secure a faster, more personalized Web. Eric and Guillermo discuss the benefits of using AI as part of the support structure for your SaaS product. Guillermo makes a great point that AI is more trustworthy when it comes to d...