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/

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 technology
• How to build a tech-enabled logistics startup from zero to scale
• Why trust and delegation are essential for growing your engineering team
• Lessons in leadership, hiring, and managing growth from startup to global scale
• The role of AI and neural networks in transforming traditional industries

Whether 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/

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/

• 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-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.

Whether 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/

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/

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/

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/

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 things like booking a flight online can lead to malicious actors scamming people out of their hard earned money.

Eric recalls his work with an executive at OpenAI, where he had a sneak peak into what we now know as ChatGPT, and their team was by no means blind to the possibility of their tech being used for the wrong reasons. The team at OpenAI had factored this in, and are cognizant of the fact that they are responsible for safety regulations for their software.

Raj speaks on AI regulation, and believes that the biggest governments in the world will regulate AI usage appropriately, as none of them are interested in AI-supported crimes. This doesn’t mean that all regulation will be the same, as global superpowers have differentiating viewpoints in their social and governing philosophies, which could cause problems down the line.

Change happens faster than we think. Raj uses the analogy of how fast cars replaced horses in the early 1900’s, when talking about how quickly the AI revolution can take place. Predictions are typically made drawing comparisons to the past, but as it’s been proven time and time again - the future comes quicker than we can possibly imagine, and Raj sees a similar pattern with how AI is disrupting us right now.

Tune into the full episode to learn more wisdom about the upcoming AI revolution!

HIGHLIGHTS:

00:00 What’s the true value of AI?
03:48 Does tech democratization lead to good or evil?
07:02 AI Regulations on social media 
09:53 The potential destructiveness of AI
12:41 GameStop and Silicon Valley Bank 
16:59 Change happens faster than we think

Connect with Raj - https://www.linkedin.com/in/rajvermaceo/

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 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/

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 to ensure quality conclusions due to there being too many points of failure. 

Big tech has a huge data advantage over mid-market competitors due to the fact that leveraging data is super expensive. SingleStore is on a mission to democratize data utilization in smaller companies, which also reflects in their client base - SaaS companies between $10-300 million ARR see the most benefit from implementing SingleStore, and their best performing segment are go-to-market tools, which is a motion that historically doesn’t rely on data as much as other parts of the business.

Generative AI is changing the way companies utilize data. Raj mentions that in the digital age, generative AI has been in the making for decades. He sees AI being discussed in 3 buckets - first one being that it will help automate easy work, second being that hard tasks will become easy, and third being that the impossible will become possible. He predicts that 50% of software jobs will become automated. 

Raj is fascinated by what it means for the impossible to become possible. He believes that science will be the sector that will see the most growth from AI, and he speaks on how AI is changing the way we approach medicine. 

Tune into the full episode to learn more about how SingleStore is democratising data!

HIGHLIGHTS:
00:00 What does SingleStore do?
02:06 The problem SingleStore saw in the market
05:38 How agile teams suffer due to inefficient data tools
09:21 What keeps incumbency in place? 
12:47 How early stage startups can leverage their data

16:42 How generative AI is changing the world
21:40 AI implications in medicine

 

Connect with Raj - https://www.linkedin.com/in/rajvermaceo/

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 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/

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 team can run seamlessly and avoid bureaucracy and micromanagement.  In order to get to that point, psychological safety is a must - which means you need to make sure that your people don't hesitate to share their opinions and viewpoints because they know they won't be punished for having the wrong idea.  Eric recommends "The SPEED Of Trust", a book by Stephen M. R. Covey, which shows how trust—and the speed at which it is established with clients, employees, and all stakeholders—is the single most critical component of a successful leader and organization.

In order to create trust in the marketplace, you need to have a customer service standard that goes above and beyond to please customers and settle disputes in a way that makes the customer feel heard, appreciated, and ultimately a winner.

When it comes to investment, trust is a huge factor. Trust is built over time, which means you should always give a reasonable amount of time for processes like due diligence, otherwise you'll never secure venture capital.

Check out the full episode to learn how to build trust in your business!

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 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/