In this episode, Ryan Gilbert shares how he escaped seven years in supply chain by building Workspaces, a newsletter showcasing creative home offices that now reaches 15,000+ subscribers. After countless tech job rejections from Wisconsin, Ryan discovered that building in public could open doors that resumes couldn't.

We dive deep into his journey from secretly starting a pandemic project to landing roles at Product Hunt, experiencing a hollow acquisition with Loops, buying back his creation for $1, and finally joining beehiiv. Along the way, we explore why he manually posts everything (6,000+ tweets and counting), the psychological complexity of selling your own creation, and how becoming a father to baby Lily has reshaped his approach to creative risk.

Big Takeaways:

• How side projects can bypass traditional hiring gatekeepers
• The power of piggybacking on others' audiences for growth
• Why consistency matters more than perfection (publishing every weekend since April 2020)
• The hidden costs of acquisition success
• How parenthood changes your relationship with creative risk
• Why manual presence beats automation for authentic connection

Design management is evolving faster than ever. Kris Puckett, the "Ted Lasso of design managers" at Shopify, shares an unfiltered look at navigating this shift - from bombing his Figma interview to embracing AI tools he once resisted.

In this candid conversation, we explore why companies now demand player-coaches over pure managers, how to survive brutal job searches (publicly), and why "vibe coding" represents the future of design leadership. Kris reveals how AI finally unlocked his 20-year dream of building an iOS app and why being a "personality hire" might actually be your superpower.

Essential listening for design leaders adapting to industry changes, anyone struggling with job searches, or designers curious about integrating AI without losing their creative soul.

Some Key Takeaways:

• The player-coach model is reshaping design leadership - Companies want leaders who can both manage and make
• Being a "personality hire" is a compliment - Relational skills combined with craft create unique value
• Remote culture requires intentional effort - "We've lost some of our fight to maintain relationships"
• AI unlocks impossible projects - After 20 years of trying, Kris built his app using Claude and Cursor
• Failure teaches faster than success - Bombing interviews led to complete portfolio rebuilds
• Show the thing, not the deck - Vibe-coded prototypes beat presentations every time
• Patience with AI pays off - "The ones that are really patient... can get their idea out there"

Matt Varughese, CEO of 8020 and former petroleum engineering student, shares his unconventional journey from retail work at Nike to building one of the most respected Webflow agencies in the industry. This conversation explores how strategic naivety, cold emailing, and the courage to reject traditional career paths led to working with clients like Ellen DeGeneres, Dr. Andrew Huberman, and Chance the Rapper.

Key Takeaways

• Strategic ignorance as a superpower: Not knowing how hard agency life would be allowed Matt to take risks that expertise would have prevented
• Cold emailing with proof of work: The exact strategy that landed Chance the Rapper - showing value upfront instead of asking for meetings
• Project minimums are negotiable: Taking smaller projects from big names can lead to massive long-term relationships
• AI is flipping the difficulty curve: Marketing websites are now harder to automate than web apps - creating new opportunities
• Relationships over revenue: Every major client came through relationships and referrals, not traditional sales

Timestamps

• [00:00] Introduction and Matt's unique agency structure
• [02:26] Why aviation and motorcycles beat screen time
• [04:01] Indian immigrant parents vs. creative career aspirations
• [09:00] Starting Websterpiece in high school - the $525 first client
• [14:50] The Snapchat geo-filter hack that got Chance's attention
• [22:36] From contractor to CEO - the Tiny acquisition story
• [33:59] The lawsuit on day one of running 8020
• [41:32] How referrals led to Ellen DeGeneres and Huberman Lab
• [51:14] Going full circle - buying back the agency
• [56:38] The cold email philosophy and proof of work strategy
• [59:06] Why AI + Webflow is the next frontier

Resources Mentioned

• 8020 Agency: [8020.com]
• The Visual Developers Podcast (co-hosted by Matt)
• Peter Kang's agency articles (Barrel)
• Blair Enns - agency thought leadership
• Cursor + Webflow AI workflows
• Supercast - premium podcast platform

Guest Information

Matt Varughese is CEO and Partner at 8020, a leading Webflow Enterprise agency. Starting his first agency Websterpiece while in high school, Matt has built websites for Chance the Rapper, Ellen DeGeneres, Dr. Andrew Huberman, and more. He splits time between Oklahoma City and New York.