Executives Unplugged

Real conversations with CEOs and operators about the playbooks behind world-class teams.

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Recent Episodes

Keith Cowing 10/21/25 Keith Cowing 10/21/25

From Trade Shows to Target’s Shelves: Grow 500% in a Year with Recoup Co-founder Siwat Siengsanaoh

From trade show volunteers to a 500-store Target launch: Recoup’s Siwat Siengsanaoh reveals how advisory boards, polarizing ginger branding, and rapid feedback loops 5x’d growth in one year.

Keith Cowing 9/15/25 Keith Cowing 9/15/25

From Burnout to Breakthrough: Master Your Calendar

Flip your calendar from Tetris chaos to a superpower: audit, analyze, and shift 10% of your time to double your momentum and stave off burnout.

Keith Cowing 7/24/25 Keith Cowing 7/24/25

From Silos to Studios: A New Playbook for Building Faster, Smarter Teams

Trade hyper-specialized silos for AI-powered studios: build nimble 2-3 person teams that take inspiration from early hip hop producers and and ship 10x faster.

Keith Cowing 7/10/25 Keith Cowing 7/10/25

Driving Rapid Change Without Breaking Your Team: Mastering the Art of Cadence and Commitment

Lead fast change without crushing your team: build trust with a steady cadence and rock-solid commitments.

Keith Cowing 6/18/25 Keith Cowing 6/18/25

Don’t leave your moral compass at home with Natasha Jaffe

Guard your team’s magic: Stop chasing productivity hacks that crush flow state—Natasha’s playbook shows how to lead reorgs and AI shifts without losing the curiosity that builds great products.

Keith Cowing 4/30/25 Keith Cowing 4/30/25

From Ballet to Scalpel to CEO: Reinvention, Resilience & Hiring Unconventionally

Hire for inner spark over resume polish: a ballet dancer-turned-surgeon shares how unconventional picks built a powerhouse team—and how to reinvent yourself along the way.

Keith Cowing 2/27/25 Keith Cowing 2/27/25

From Big Company to AI Startup, a product, and revenue in 12 Months: How Fast Execution Beats Perfect Planning with Uday Chakravarthi

How Uday (head of product at Atlassian) went from a big company to AI startup founder at lightning pace with ruthless focus, weekly sprints, and real-time advisor feedback.

Keith Cowing 2/7/25 Keith Cowing 2/7/25

From the Mat to the Boardroom: Iron Mike Steadman on Grit, Branding & the Power of Action

Bounce back from life's hardest hits: Mike Steadman, a boxing champ-turned-coach for veteran entrepreneurs shares how owning your niche and relentless action can turn adversity into unbreakable momentum.

12/18/24 12/18/24

Incentives, Truth and Selling the Right Way with Wayne Morris

Sell with truth, not tricks: Wayne Morris reveals how honest GTM diagnostics and smart incentives can build the highest performing sales teams.

10/21/24 10/21/24

How to Lead From Growth Stage to IPO with Nayya President and COO Sarah Liebel

Lead like a founder without burning trust: Sarah Liebel (COO at Nayya) reveals how to scale companies from growth stage through IPO while blending empathy, quick decisions, and trust.

9/19/24 9/19/24

From Self-Taught Developer to CTO and Inspiring Leader with Danielle Leong

From marketer to CTO: Danielle Leong shares how to lead with radical transparency by sharing open playbooks, building trust across teams, and managing tricky leadership moments like managing ex-peers.

9/18/24 9/18/24

From Open-Heart Surgery and Mom's Ginger Teas to Beverage Entrepreneur with Siwat Siengsanaoh

From hospital bed to beverage company CEO: Siwat Siengsanaoh shares how critical health scares, mom's ginger remedies, and lessons from soccer coaches inspired his path to resilience and leading with purpose.