
How Redwood Services Built a $1.1B Home Services Platform | VIP Guests Richard Lewis & John Conway
Chris Yano, Chad Peterman, and Aaron Gaynor are joined in the Home Services VIP Room by VIP guests Richard Lewis, CEO of Redwood Services, and John Conway, COO of Redwood Services.
In this episode, the group dives deep into the evolution of private equity in home services, scaling multi-location businesses, leadership development, operational inefficiencies, marketing, technician retention, and what it really takes to build a billion-dollar platform in the trades.
Richard and John break down Redwood Services’ growth from a startup platform in 2020 to a company valued at approximately $1.1 billion while partnering with dozens of leading HVAC, plumbing, and electrical businesses across the country. The conversation explores how Redwood approaches acquisitions differently, why culture and people matter more than ever, and what separates scalable operators from companies that stay stuck.
The episode also covers leadership ceilings, dispatching, call center leakage, marketing spend, budgeting, technology, accountability, retention, and the future of consolidation in home services.
If you're a contractor, operator, manager, or entrepreneur in the trades, this episode is packed with real conversations and actionable insights from some of the top minds in home services.
00:00 – Welcome to the Home Services VIP Room
01:15 – Introducing Redwood Services & the VIP Guests
03:30 – The Origin of “Cut a Rug”
06:00 – How Chris Met Redwood in the Early Days
08:30 – Redwood’s Growth to a $1.1B Valuation
11:00 – Building Redwood Around People & Culture
14:15 – How Home Services Has Changed Since 2020
18:00 – Why Small Operators Are Struggling to Compete
21:00 – The Technology & Marketing Arms Race in Home Services
24:00 – Why Some Companies Hit a Ceiling
27:00 – The Biggest Problems in $3M–$5M Businesses
30:15 – Margin Leakage, Labor Costs & Pricing Mistakes
34:00 – Leadership, Hiring & Building Scalable Teams
38:00 – Growing Leaders Faster Than the Business
42:00 – Why Accountability Gets Harder as You Scale
45:00 – Redwood’s Secret Sauce: Connection & Collaboration
48:00 – The Real Problem With Home Services Marketing
51:00 – What’s Broken in Home Services?
54:00 – Technician Retention & Industry Turnover
57:00 – Why Operational Leakage Matters More Than Marketing
59:00 – Final Thoughts on Scaling, Leadership & Growth
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