Chaos To Clarity

Full Cycle Executive Coaching
  • 5.0 (9)
  • ENTREPRENEURSHIP
  • UPDATED BIWEEKLY

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.

  1. NOV 21

    Building Painkillers, Not Vitamins: How Daniel Marashlian Scaled Drata to 700 Employees

    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 from a small, scrappy team to 700+ employees — and the hard lessons learned along the way. 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. In this episode: The early lessons that shaped Daniel’s mindset as a founderHow Drata turned compliance from a blocker into a growth engineWhy “build a painkiller, not a vitamin” became his guiding principleThe breaking points that come with hypergrowth — and how to fix themWhen to layer, delegate, and hire before you’re underwaterHow to turn security into a company culture, not a checkboxWhether 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. 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/

    47 min

  2. NOV 7

    Scaling Product-Led Growth to $300M with ClickUp COO Gaurav Agarwal

    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 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. In This Episode: How ClickUp grew to $300M ARR from San Diego  The real meaning of product-led growth (and why it’s misunderstood)  Finding the line between free and paid features  How to build a customer-obsessed culture  Running 100+ experiments per week without chaos  The secret to scaling operations without killing innovation  Gaurav’s leadership framework: business first, team second, self third  Key Quote: “Our speed is our secret weapon. You can’t think your way to success — you have to ship, learn, and iterate relentlessly.” 🎧 Full episode and more founder resources at chaostoclarity.io 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/

    46 min

  3. OCT 17

    When Success Means Life or Death: Ryan Rusnak’s Journey Building Airspace

    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 routing in real time—saving lives, money, and minutes. This episode dives into: The story behind Airspace and its life-saving logistics technologyHow to build a tech-enabled logistics startup from zero to scaleWhy trust and delegation are essential for growing your engineering teamLessons in leadership, hiring, and managing growth from startup to global scaleThe role of AI and neural networks in transforming traditional industriesWhether you’re a startup founder, CTO, or just fascinated by the intersection of AI and logistics, this conversation will inspire you to think bigger about what technology can achieve when the stakes are real. 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/

    50 min

  4. OCT 3

    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 platform, and what it took to scale from two founders to a household brand that processed over a billion dollars in giving. Andy also reveals the insights behind his newest venture, EyePop.ai, a computer vision platform making AI accessible to developers and businesses across industries. He explains how modern visual intelligence can turn everyday images and video into actionable data—from analyzing pickleball swings to inspecting drone footage of rooftops—and why speed, lean teams, and clear product design are essential in today’s fast-moving AI landscape. Listeners will learn: How GoFundMe evolved from a simple savings concept into the world’s leading personal fundraising site  The technical and UX hurdles of early fintech and how Andy’s team overcame them  Why bootstrapping worked for GoFundMe but venture funding is key for AI startups  The critical role of co-founders, emotional resilience, and a “stoic CEO” mindset in surviving the startup grind  Practical advice for founders on team building, product iteration, and staying ahead of AI’s rapid innovation curve  Whether you’re a first-time founder, a product leader, or an investor tracking the next wave of AI infrastructure, Andy’s journey offers a masterclass in startup strategy, growth, and perseverance. 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/

    54 min

  5. SEP 22

    Scaling up to $100M with Afif Khoury, CEO of Soci

    Key TakeawaysFinding 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-thirds of sales opportunities to improve retention.Customer success over sales growth. Afif shares why focusing on customer success—hiring seasoned leaders and building award-winning CS systems—was the key to sustainable expansion.Applied AI in marketing. Beyond generative content, SOCi is developing “applied AI” to manage end-to-end marketing workflows across thousands of locations, giving teams back thousands of hours.Culture as scalable DNA. SOCi’s values—Selflessness, Overachievement, Customer Centricity, and Innovation—guide hiring, recognition, and leadership at every stage of growth.Leadership principles. Hire people better than you, empower them, and balance founder involvement with trust. Culture will evolve as you scale, but clarity of values keeps the organization aligned.Why ListenWhether you’re an early-stage founder or leading a growth-stage team, this conversation is a masterclass in resilience, strategy, and culture-driven leadership. Afif’s journey shows how to navigate rejection, make data-driven pivots, and build software—and teams—that scale. 👉 Listen now to learn how to build conviction, lead through pressure, and turn a startup into a unicorn. 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/

    33 min

  6. SEP 8

    Neal Bloom on Building San Diego’s Startup Ecosystem

    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 overcome them  If you are a founder, investor, or community builder looking to understand the future of San Diego tech, this is a must-listen conversation. Key Topics & Takeaways Startup Communities Framework: Why Brad Feld’s Startup Communities is Neal’s “startup bible”  Investing in People, Not Just Companies: Neal’s philosophy of betting on founders first  From Coffee Meetings to Community Hubs: Why San Diego needs physical spaces for collisions, not just coworking desks  The State of San Diego Startups: Momentum, challenges, and opportunities post-COVID  Founder-Led Movement: How entrepreneurs can create “gravity wells” to attract investors, talent, and resources  Event Co-Founders: How to keep community events consistent and impactful without founder burnout 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/

    54 min

  7. 04/12/2024

    AI POWERED ASSISTANTS - What’s Next For AI Assistants with Jason Corso, Co-Founder of Voxel51, Part 2

    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 game changer for productivity and mapping, but it’s not yet at the level of flexibility that would eliminate most of the grunt work. Eric and Jason speak on how they’d like to see AI platforms collaborate and get to a point where they not only map out your tasks, but also do a lot of the preliminary work - just like an assistant would.  Generalized and personalized AI assistants are the next big step that would vastly increase the value that executives get from utilizing AI in their daily workflow. Eric speaks on how he’s currently using ChatGPT to some level of success, but also mentions something we’ve all felt - the need for a system that compartmentalizes workflows, remembers information and draws custom next steps from previously established context. Everyone’s excited for what’s next for generative AI. Even though closed models are currently performing better than open-source, this situation will most likely change with time as more tools become available. Jason breaks down annotation strategies and speaks on how the idea of just taking data and training your own models might not be the most efficient way to drive innovation as an AI startup. There’s a lot of work in understanding how to create good datasets, which is something that most companies are missing. Tune into the full episode to learn more about the potential of AI! HIGHLIGHTS: 00:00 Utilizing Microsoft AutoGen 04:04 What’s next for AI assistant platforms?   09:03 The problem with ChatGPT  12:47 What’s the next step in AI tool development? 17:31 The problem with questionable datasets Connect with Jason - https://www.linkedin.com/in/jason-corso/   Check out Voxel51 - https://voxel51.com/   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/ 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/

    26 min

  8. 04/11/2024

    AI DATA ACCURACY - How To Approach Working With Datasets with Jason Corso, Co-Founder of Voxel51, Part 1

    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 academic career he started to ask himself - “can I have a bigger impact on the world?”, which led him to meet his co-founder and start Voxel 51. Both of them had a passion for machine learning and an ability to write code - which is how his transition from academia to consulting began. In the early days they received a grant which worked out well and funded them through the process of building their first service.  Building a service, however, was never part of the plan. Once they realized that the limitations of the grant won’t enable building a product, they sought out venture capital. This venture capital boost allowed them to build out their open-source platform which has more than 2 million downloads as of this episode.  Jason speaks on the early success stories of Voxel51. One of their earliest clients took just 1% of their data and in a few hours they were able to look at the data visually, which enabled them to figure out where mistakes were made. Data quality is more important than the sophistication of the system, and Voxel51 enables their clients to find where inefficiencies live. Even with a great system - human input is still needed when it comes to quality control. Jason speaks on how humans filling in the gaps when the system is less certain is highly effective - even though it doesn’t scale. Eric speaks on how experienced data scientists develop an almost 6th sense when looking at data and understanding that something is wrong and a change is in order.  Check out the full episode to learn more on how to approach utilizing data!  HIGHLIGHTS: 03:41 Building a service-based business 05:21 When do you utilize Voxel51 in the development process? 09:52 Quality or quantity - what’s more important for your data? 15:05 The importance of human pattern recognition  18:03 New applications of AI tools Connect with Jason - https://www.linkedin.com/in/jason-corso/   Check out Voxel51 - https://voxel51.com/   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/ 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/

    25 min
See All (67)

Ratings & Reviews

5
out of 5
9 Ratings

About

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.

Information

  • Creator
    Full Cycle Executive Coaching
  • Years Active
    2022 - 2025
  • Episodes
    67
  • Rating
    Clean
  • Show Website
    Chaos To Clarity