Inside How Crosby Is Automating the $1 Trillion Legal Industry | Ryan Daniels of Crosby

Who Actually Wins When Everyone Has AI | Dan Shipper

AI is changing what it means to be good at your job. Dan Shipper, co-founder and CEO of Every, shares how he went from productivity writer to leading an AI-native company running six apps with a lean team, without being a full-time engineer. In this episode with Jason Shuman, Dan gets into: - how shipping work now looks more like directing - systems than writing code - why managing AI feels like running a company - how compound systems prevent the same mistakes from happening again - why allocation is becoming the most important skill heading into 2026 This episode offers a clear look at how founders and operators are adapting as AI reshapes how work gets done. Connect with us here: Dan Shipper: https://www.linkedin.com/in/danshipper/ [https://www.linkedin.com/in/danshipper/] Jason Shuman: https://www.linkedin.com/in/jasonshuman/ [https://www.linkedin.com/in/jasonshuman/] Every Inc: https://www.linkedin.com/company/everyinc/ [https://www.linkedin.com/company/everyinc/] Change Order: https://www.linkedin.com/company/change-order/ [https://www.linkedin.com/company/change-order/]

This AI Startup Is Changing How Call Centers Work Forever

When’s the last time you had a good customer experience? Alex Levin, Co-founder and CEO of Regal AI, is building AI Phone Agents that handle millions of customer calls for a small fraction of the cost, and drive higher customer satisfaction.  In this episode with Jason Shuman, Levin gets into: • why companies moved away from phone calls despite customer demand. • how legacy vendors decided voice wasn’t worth improving. • why AI voice is now cheaper and more consistent than humans. • what slows big companies from adopting voice AI. • how AI handles the tier-1 work while humans focus on harder problems. Connect with us here: 1. Alex Levin: https://www.linkedin.com/in/alexlevin1 [https://www.linkedin.com/in/alexlevin1] 2. Jason Shuman: https://www.linkedin.com/in/jasonshuman/ [https://www.linkedin.com/in/jasonshuman/] 3. Change Order: https://www.linkedin.com/company/change-order/ [https://www.linkedin.com/company/change-order/] 4. Primary Venture Partners: https://www.linkedin.com/company/primary-venture-partners/ [https://www.linkedin.com/company/primary-venture-partners/]

Inside How Crosby Is Automating the $1 Trillion Legal Industry | Ryan Daniels of Crosby

What if the future of law isn’t about replacing lawyers, but supercharging them? Ryan Daniels, Co-founder and CEO of Crosby, is building the world’s first AI-powered law firm that blends human judgment with machine speed to handle contracts in hours, not days. In this episode with Jason Shuman, he discusses: • why the $1T legal industry is finally ready for automation. • how Crosby became an AI-first law firm that works through Slack. • what he learned from India’s legal outsourcing boom. • why speed is the real edge in legal tech. • how AI and human lawyers now work side by side. Connect with us here: 1. Ryan Daniels- https://www.linkedin.com/in/crosbyryan/ [https://www.linkedin.com/in/crosbyryan/] 2. Jason Shuman- https://www.linkedin.com/in/jasonshuman/ [https://www.linkedin.com/in/jasonshuman/] 3. Change Order- https://www.linkedin.com/company/change-order/ [https://www.linkedin.com/company/change-order/] 4. Primary Venture Partners- https://www.linkedin.com/company/primary-venture-partners/ [https://www.linkedin.com/company/primary-venture-partners/]

The Newsletter Everyone in Tech Reads | The Generalist & Mario Gabriele

The pace of innovation has never been faster or harder to follow. Mario Gabriele [https://www.linkedin.com/in/mariogabriele/], founder of The Generalist, a newsletter and community helping over 150K readers make sense of what matters in tech, AI, and venture, joins Jason Shuman [https://www.linkedin.com/in/jasonshuman/] to share how deep research and storytelling help him decode the forces shaping what’s next. They get into: • the mental models behind The Generalist’s most-read stories • why 95% of early stage investing comes down to the founder • how writing builds sharper intuition than data ever could Connect with us here: 1. Mario Gabriele- https://www.linkedin.com/in/mariogabriele/ [https://www.linkedin.com/in/mariogabriele/] 2. Jason Shuman- https://www.linkedin.com/in/jasonshuman/ [https://www.linkedin.com/in/jasonshuman/] 3. Change Order- https://www.linkedin.com/company/change-order/ [https://www.linkedin.com/company/change-order/] 4. Primary Venture Partners- https://www.linkedin.com/company/primary-venture-partners/ [https://www.linkedin.com/company/primary-venture-partners/] 00:00 Trailer 01:06 The Generalist: From Concept to Execution 04:12 Writing Process and Research Techniques 13:04 Navigating the Media Landscape and Investment Insights 35:51 Challenges in Seed Stage Investing 36:47 Evaluating Founders: Insights from Hummingbird 45:11 Market Dynamics and AI Bubble 59:00 Lessons from the Generalist's Journey

The Robotics Startup Governments Can’t Ignore | Rahul Sidhu on Aerodome

With emergency response times under three minutes, the future of public safety is airborne. Rahul Sidhu [https://www.linkedin.com/in/rahulsidhu/], co-founder and CEO of Aerodome, joins Jason Shuman [https://www.linkedin.com/in/jasonshuman/⁠] on Change Order [https://www.linkedin.com/company/change-order/⁠] to share how he and his team are deploying drones as ‘first responders’, combining automation and aviation to transform how cities handle critical events. Together, they explore: • how a pandemic-induced staffing crisis gave rise to a new model of air support • why policing is entering its “guy in the chair” era • what DJI taught the world about market capture and policy Connect with us here: 1. Rahul Sidhu- https://www.linkedin.com/in/rahulsidhu/ [https://www.linkedin.com/in/rahulsidhu/] 2. Jason Shuman- https://www.linkedin.com/in/jasonshuman/ [https://www.linkedin.com/in/jasonshuman/] 3. Change Order- https://www.linkedin.com/company/change-order/ [https://www.linkedin.com/company/change-order/] 4. Primary Venture Partners- https://www.linkedin.com/company/primary-venture-partners/ [https://www.linkedin.com/company/primary-venture-partners/]