Ever felt like your company is running in circles while you quietly burn out, stuck between drive and exhaustion?
This episode is a blunt, emotionally raw exploration with Lindsay Gibson, COO of TextNow, a leader who’s walked away from the grind, returned for redemption, and rebuilt both companies and herself from the inside out. Sivana Brewer dives deep with Lindsay into the shock of losing vision, the chaos of remote work, and the brutal clarity that comes only after you’ve crashed headlong into career “success.”
If you’re tired of vague leadership advice and want exclusive, no-BS strategies for authentic leadership, unclenching burnout’s grip, and making culture work for real teams, listen right now. Miss this, and you might repeat the pain Lindsay barely escaped. These lessons are battle-forged, urgent, and unlike anything the standard playbooks offer.
Timestamped Highlights
[00:01:11] – The brilliant but gritty origin of TextNow: solving real pain for people who have to choose between a phone bill and groceries
[00:02:45] – Why Lindsay left her COO seat (twice) and what chasing “interesting work” really costs
[00:04:34] – The BlackBerry “return rate” disaster: how fixing buyer’s remorse became a master class in real-world delegation
[00:07:49] – The shocking truth: Engineering wasn’t the problem—here’s what really derails a company’s goals
[00:10:11] – The brutal downside of remote-first culture… and the hardest part of rebuilding accountability across a fractured team
[00:14:32] – Motherhood, loss, and the hidden price of ambition: Lindsay’s real talk on the boundaries she’ll never break again
[00:19:04] – “Dead bodies in the process”—when leadership feedback stings and the rebirth of authentic management
[00:27:54] – Why remote teams lose their soul (and how one-on-one connection fights back against isolation)
About the Guest
Lindsay Gibson is the Chief Operating Officer of TextNow, a disruptive, ad-supported mobile carrier serving millions who demand true flexibility in mobile communications. With over two decades shaping iconic tech cultures, including a 16-year run at BlackBerry, she’s mastered the hard edge of scaling, comeback leadership, and authentic team connection. Known for leading through crisis and comeback, Lindsay is a straight-talker driven by integrity and obsession with growth.
🔗 LinkedIn | Website
Mentioned Resources
About the Co-Host
Sivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.
🔗 Connect with Sivana on LinkedIn
Important Links
The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.
