With growth comes growing pains. Every great leader has faced turmoil, setbacks, and the overwhelming stress of holding together a growing company as it nearly comes apart at the seams. You are not alone. Listen in as we share the stories and guidance from entrepreneurs, executives, and thought leaders who have walked the path from chaos to clarity.
Chaos To Clarity
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68 episodes
Updated Weekly
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Podcast Overview
With growth comes growing pains. Every great leader has faced turmoil, setbacks, and the overwhelming stress of holding together a growing company as it nearly comes apart at the seams. You are not alone. Listen in as we share the stories and guidance from entrepreneurs, executives, and thought leaders who have walked the path from chaos to clarity.
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Publishing Since
8/31/2022
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Recent Episodes
January 28, 2026
Inside Techstars San Diego: How Misti Cain Builds High-Caliber Startups
<p>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 across industries, technologies, and geographies.</p> <p>Misti shares why this year’s cohort is different. These founders aren’t just experimenting. They’re arriving with deep domain expertise, early traction, paying customers, and bold visions that span everything from biotech document automation to haptic wearables for the blind to AI compliance for regulated industries. The diversity of ideas is matched only by the diversity of founders — spanning San Diego, Mexico, Canada, Paris, New York, Florida, and more.</p> <p>A major advantage of the program comes from the partnership between Techstars and San Diego State University. Startups gain access to engineering support, prototyping labs, specialized testing, interns, and warm introductions to key university resources. Misti explains why this ecosystem collaboration creates an environment where founders can achieve more in 90 days than most can do in a year.</p> <p>The conversation also explores Misti’s personal journey: from digital marketing strategist, to startup consultant, to award-winning Techstars mentor, to investor, and now Managing Director. Her story highlights the importance of curiosity, lifelong learning, and the power of giving first — a philosophy that sits at the heart of the Techstars culture.</p> <p>Eric and Misti close by zooming out to discuss the San Diego startup ecosystem, why it offers a uniquely collaborative environment, and why founders from all over the world are beginning to choose San Diego as their home base. This episode is a deep dive into community, innovation, leadership, and what it truly takes to build a successful company.</p> <p><p>Don't forget to subscribe to the Chaos to Clarity Podcast for more invaluable episodes to help you grow your business and stay ahead of the curve!To reach out to Eric, visit https://chaostoclarity.io/</p></p>
November 21, 2025
Building Painkillers, Not Vitamins: How Daniel Marashlian Scaled Drata to 700 Employees
<p>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.</p><p>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.</p><p>He opens up about what it takes to scale from a small, scrappy team to 700+ employees — and the hard lessons learned along the way.</p><p>You’ll hear how a painful compliance process in a previous startup inspired Drata’s creation, and how Daniel transformed that frustration into a platform that changed how businesses build trust.</p><p>In this episode:</p><ul><li>The early lessons that shaped Daniel’s mindset as a founder</li><li>How Drata turned compliance from a blocker into a growth engine</li><li>Why “build a painkiller, not a vitamin” became his guiding principle</li><li>The breaking points that come with hypergrowth — and how to fix them</li><li>When to layer, delegate, and hire before you’re underwater</li><li>How to turn security into a company culture, not a checkbox</li></ul><p>Whether you’re a founder, CTO, or tech leader scaling fast, Daniel’s story shows what it means to build systems, teams, and culture that can withstand rapid growth.</p> <p><p>Don't forget to subscribe to the Chaos to Clarity Podcast for more invaluable episodes to help you grow your business and stay ahead of the curve!To reach out to Eric, visit https://chaostoclarity.io/</p></p>
November 7, 2025
Scaling to $300M with Product-Led Growth
<p> In this episode of <i>Chaos to Clarity</i>, 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.</p><p>Gaurav shares how ClickUp redefined product-led growth, balanced self-serve and sales-assisted revenue models, and built a culture obsessed with iteration and feedback. From eliminating “work about work” to running 100+ experiments per week, this conversation is a masterclass in operational excellence and founder discipline.</p><p>In This Episode:</p><ul><li>How ClickUp grew to $300M ARR from San Diego<br /><br /> </li><li>The real meaning of product-led growth (and why it’s misunderstood)<br /><br /> </li><li>Finding the line between free and paid features<br /><br /> </li><li>How to build a customer-obsessed culture<br /><br /> </li><li>Running 100+ experiments per week without chaos<br /><br /> </li><li>The secret to scaling operations without killing innovation<br /><br /> </li><li>Gaurav’s leadership framework: business first, team second, self third<br /><br /> </li></ul><p>Key Quote:</p><p>“Our speed is our secret weapon. You can’t think your way to success — you have to ship, learn, and iterate relentlessly.”</p><p><br />🎧 Full episode and more founder resources at<a href="https://chaostoclarity.io"> chaostoclarity.io</a></p> <p><p>Don't forget to subscribe to the Chaos to Clarity Podcast for more invaluable episodes to help you grow your business and stay ahead of the curve!To reach out to Eric, visit https://chaostoclarity.io/</p></p>
68 total episodes available with 4 transcripts
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