The 1000-Day CEO

Bill Canady's Podcast for PE-Backed CEOs

Real conversations with CEOs, founders, private equity leaders, and operators who’ve created measurable results — the decisions, leadership principles, and strategies behind profitable growth.

About the show

The Bill Canady Podcast features conversations with CEOs, founders, private equity leaders, and business operators who’ve created measurable results. Each episode explores the decisions, leadership principles, and operating strategies behind profitable growth — giving peers practical insights they can apply in their own organizations.

Every episode features accomplished operators sharing practical lessons from real-world leadership. From scaling businesses to navigating transformation, the focus is always on actionable insights that help others succeed.

Recent episodes

New episodes drop regularly. Available on Apple Podcasts, Spotify, YouTube, Amazon Music, iHeartRadio, Deezer and everywhere you listen.

The 1000-Day CEO

The 1000-Day CEO is a show for private equity sponsors and the CEO operators who run their portfolio companies. Host Bill Canady of the 80/20 Institute breaks down how value actually gets created inside a portco — finding the number, building the team, and turning the first 1,000 days of a hold into durable EBITDA and a clean exit. Direct, practical, and built for the people accountable for the outcome.

Cash can run short even when a business reports profit. Rob Santana and Ken Kelly join Bill Canady with two perspectives on the Kelly Roofing rescue: the financial diagnosis and the owner’s return.

Rob explains how he tested the cash forecast and confronted the decisions it revealed. Ken describes the buyback, rebuilding customer and vendor trust, and giving the team clear priorities for the restart.

For CEOs and owners, they connect cash visibility, operating discipline, and decisive leadership to the work of rebuilding a business.

IN THIS EPISODE
• Test a 13-week cash forecast against operating reality.
• Protect customers and viable operating capability.
• Use clear roles, financial controls, and a daily huddle.
• Set priorities for days 30, 100, and 1000.

CHAPTERS
00:00 Two perspectives on the rescue
00:57 When cash changed the mandate
03:02 Ken’s decision to return
04:38 Building a business that works
08:27 What was worth saving and testing cash
11:28 The buyback and rebuilding confidence
16:26 The final negotiations and the team
19:56 Restoring customer and vendor trust
24:42 What they would do differently
27:01 Priorities for days 30, 100, and 1000
30:04 What an owner should do tomorrow
33:09 Connect with Rob and Ken

CONNECT WITH THE GUESTS
Ken Kelly
Rob Santana

FULL TRANSCRIPT AND CAPTIONS
Transcript and captions are being reviewed for the final release.

FREE CEO TOOLS
Business Valuation
Growth Scorecard
Profit Concentration
Price Increase
LBO Calculator
Profit Map Calculator
All free tools

BOOK A CALL WITH BILL CANADY
Meet with Bill
Command 100

CONNECT WITH BILL CANADY
Bill Canady
The 80/20 Institute
The 1000-Day CEO

Subscribe for practical CEO conversations.

What would tell you sooner that growth is putting your cash and customer commitments at risk?

#The1000DayCEO #CashFlow #Leadership

Episode play icon

Cash, Trust, and the Kelly Roofing Rescue | Rob Santana & Ken Kelly | EP28

Episode Description

Episode play icon