Stop Doing Your Own Paperwork: The Secret Weapon of High-Producing Teams
Wed Feb 04 2026
In this episode, Chris and Matt sit down with Lindsay Rothermund, RETSY Associate Broker and Lead Transaction Coordinator. As an original team member who has been with the brokerage since its startup days, Lindsay offers a unique perspective on its evolution into a luxury powerhouse. She shares her journey from managing tracking systems for UPS air cargo to becoming the backbone of high-stakes real estate transactions, explaining exactly why top-producing agents rely on her to manage the chaos, protect their clients, and ensure no deadline is missed.
The conversation dives into the critical difference between a generic "TC mill" and the boutique, integrated partnership model at RETSY. Lindsay discusses how she builds trust with agents to act as a "first line of defense" against liability and shares wild stories from the trenches—including a transaction involving a client who committed arson. From the importance of delegation for scaling a business to the power of creative video marketing and community outreach, this episode is a masterclass on the operational side of real estate success.
00:00 – Meet RETSY’s Transaction Manager & Associate Broker Lindsay Rothermund
03:00 – From Real Estate to the 9-to-5 Grind (And Back Again)
06:26 – The Origin Story: Building the TC Department at RETSY
10:43 – How Building Trust is Critical Between Agent and TC
18:57 – Managing 300+ Transactions a Year: Why You Never Stop Learning
22:02 – The Time Machine: "Stick With It" and Trust the Process
25:05 – Why Real Estate Offers True Freedom vs. Corporate Life
27:32 – The #1 Marketing Trend for 2026: Creative Video
31:24 – Client Appreciation — Using Community Givebacks to Grow
35:19 – Advice for New Agents: Join a Team That Is Willing to Share
41:29 – The Art of Problem Solving in Complex Transactions
Learn more about RETSY
www.retsy.com
www.instagram.com/retsy
www.youtube.com/@retsy.
Original music by @jacktwarner
More
In this episode, Chris and Matt sit down with Lindsay Rothermund, RETSY Associate Broker and Lead Transaction Coordinator. As an original team member who has been with the brokerage since its startup days, Lindsay offers a unique perspective on its evolution into a luxury powerhouse. She shares her journey from managing tracking systems for UPS air cargo to becoming the backbone of high-stakes real estate transactions, explaining exactly why top-producing agents rely on her to manage the chaos, protect their clients, and ensure no deadline is missed. The conversation dives into the critical difference between a generic "TC mill" and the boutique, integrated partnership model at RETSY. Lindsay discusses how she builds trust with agents to act as a "first line of defense" against liability and shares wild stories from the trenches—including a transaction involving a client who committed arson. From the importance of delegation for scaling a business to the power of creative video marketing and community outreach, this episode is a masterclass on the operational side of real estate success. 00:00 – Meet RETSY’s Transaction Manager & Associate Broker Lindsay Rothermund 03:00 – From Real Estate to the 9-to-5 Grind (And Back Again) 06:26 – The Origin Story: Building the TC Department at RETSY 10:43 – How Building Trust is Critical Between Agent and TC 18:57 – Managing 300+ Transactions a Year: Why You Never Stop Learning 22:02 – The Time Machine: "Stick With It" and Trust the Process 25:05 – Why Real Estate Offers True Freedom vs. Corporate Life 27:32 – The #1 Marketing Trend for 2026: Creative Video 31:24 – Client Appreciation — Using Community Givebacks to Grow 35:19 – Advice for New Agents: Join a Team That Is Willing to Share 41:29 – The Art of Problem Solving in Complex Transactions Learn more about RETSY www.retsy.com www.instagram.com/retsy www.youtube.com/@retsy. Original music by @jacktwarner