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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