Episode 247: Redwood Services Rise to $400M & Keep the Culture

This episode of To The Point is more than a conversation — it’s a playbook for redefining success. Chris sits down with Richard Lewis, CEO of Redwood Services, a leader proving that prioritizing people isn’t just good for culture — it’s the ultimate growth strategy.

Redefining Success Through People

After starting out on Wall Street and climbing the ranks at ServiceMaster and Terminix, Richard witnessed how corporate red tape could hold businesses back. Determined to change the game, Richard co-founded Redwood Services in 2020, right in the middle of a pandemic.

His mission? Build something better.

Today, Redwood partners with 16 top-tier companies nationwide, generating over $400 million annually. However, for Richard, real success lies in culture. “Connection is everything,” he says, and that principle drives Redwood’s approach:

• Hiring exceptional talent
• Supporting collaboration between partners
• Empowering businesses to maintain their unique identity while scaling strategically

The Redwood Way: No Playbooks, Just People

Forget cookie-cutter playbooks and corporate rebrands. Richard’s approach is refreshingly simple: “We embrace the ownership and embrace the management … We don’t rebrand, we don’t drop a playbook off on their desk … We take amazing companies, partner with them, hire amazing people on the Redwood team, and then get after it together.”

This episode pulls back the curtain on how Redwood has become an industry powerhouse, all while keeping its focus on what truly matters: people.

• Why Richard left corporate life to create a people-first business
• The secret to helping businesses grow without losing their identity
• How culture drives long-term success and scalability
• What it means to hire “thesis changers” who elevate your business
• Leveraging peer collaboration to spark innovation
• Strategies for overcoming today’s marketing challenges
• The untapped potential in the home services industry
• And so much more!

Make Your Move

This isn’t just another podcast episode — it’s your chance to level up. Are you investing in your people? Are you embracing change? Are you ready to take your business to the next level?

As Richard puts it: “We’re in an amazing, recession-proof industry with limitless potential — so get after it!”

If you’re looking for practical ways to grow your business while keeping a strong, people-first culture, you’ll love this episode. Richard’s insights pair perfectly with our chat with John Conway, Redwood’s COO. John dives into why prioritizing people and processes over profits is the key to lasting success! Pair that with the tools and connections from Nexstar Network, and you’ll have some great tools to start making big moves.

Remember: You don’t have to do everything, but you’ve got to do something. No. Zero. Days.