The 1000-Day CEO

Bill Canady

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Management

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.

2d ago

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

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
Sep 30

Build a Business Buyers Want | Matt Tortora | EP27

Would a buyer want the business you are building? Matt Tortora, founder of Drive Equity, joins Bill Canady to explore what makes a founder-owned company more valuable—and why exit preparation starts years before a sale. A strong profit number is only part of the story. Matt and Bill discuss founder dependence, customer concentration, recurring revenue, gross margins and clean financials through a buyer's eyes. They explain why a headline valuation can look very different from the cash and risk a seller takes away from a deal. The conversation then turns to acquisitions: defining what to buy and why, considering equity, debt and seller financing, building an organization that can absorb another company, and assessing cultural fit. Matt also shares the personal adjustment of moving from founder to employee after an exit. IN THIS EPISODE • Build systems and a management team that can perform without the founder. • Work backward from an exit goal using realistic assumptions and sustainable earnings. • Prepare the acquisition thesis, financing and integration plan before pursuing a deal. CONNECT WITH MATT TORTORA Drive Equity: https://www.driveequity.co/ LinkedIn: https://www.linkedin.com/in/mtortora FREE CEO TOOLS Business Valuation Calculator: https://the8020institute.com/business-valuation-calculator/ Profitable Growth Scorecard: https://the8020institute.com/profitable-growth-scorecard/ Profit Concentration Analyzer: https://the8020institute.com/profit-concentration/ Price Increase Impact Calculator: https://the8020institute.com/price-increase-calculator/ LBO Calculator: https://billcanady.com/lbo-calculator/ Profit Map Calculator: https://billcanady.com/profit-map-calculator/ All free tools: https://the8020institute.com/free-tools/ BOOK A CALL WITH BILL CANADY Meet with Bill: https://calendly.com/billcanady/meet-with-bill Command 100 — talk directly with Bill: https://calendly.com/billcanady/command-100 CONNECT WITH BILL CANADY Bill Canady: https://billcanady.com/ The 80/20 Institute: https://the8020institute.com/ The 1000-Day CEO: https://1000dayceo.com/ Subscribe for practical conversations about decisive leadership, profitable growth, operational discipline, and building lasting enterprise value: https://www.youtube.com/@billcanady?sub_confirmation=1 If you stepped away for 90 days, what would your business need to keep growing without you? #The1000DayCEO #ExitPlanning #BusinessGrowth
Sep 26

You've Built Success. What Will You Do With It? | Bob Smith | EP26

You've built a successful business. What should that success make possible? Bill Canady and Bob Smith discuss purpose, family wealth and civic leadership. Bob draws on advising families and board service at Ohio Northern University and JobsOhio. He explores life beyond a job title, how to contribute on a board, and where charitable giving can matter. He also recalls Ohio's pandemic response and the need to understand concerns before persuading people. IN THIS EPISODE • Define what wealth means to your family. • Build trust through listening and truth. • Respect board and management roles. • Test philanthropic impact and expectations. • Ask before advising; stay curious. • Uphold criteria when saying no. CHAPTERS 00:00 Success, stewardship and what comes next 01:08 What does money mean to your family? 02:29 Finding purpose beyond your title 03:51 Listening and telling clients the truth 06:14 What board service teaches about leadership 09:51 Influence and the work between meetings 11:15 JobsOhio and economic development 15:13 The discipline to say no 18:16 Choosing where your giving can matter 21:18 Challenge your assumptions 24:57 The question that reveals your values 26:40 Ask about concerns before asking for action 28:43 Stay curious long enough to understand 29:48 Civic leadership in a crisis 33:40 Find Bob and your next conversation CONNECT WITH BOB SMITH Robert C. Smith at Cerity Partners: https://ceritypartners.com/team/robert-c-smith/ Email Bob: bsmith@ceritypartners.com FREE CEO TOOLS Business Valuation Calculator: https://the8020institute.com/business-valuation-calculator/ Profitable Growth Scorecard: https://the8020institute.com/profitable-growth-scorecard/ Profit Concentration Analyzer: https://the8020institute.com/profit-concentration/ Price Increase Impact Calculator: https://the8020institute.com/price-increase-calculator/ LBO Calculator: https://billcanady.com/lbo-calculator/ Profit Map Calculator: https://billcanady.com/profit-map-calculator/ All free tools: https://the8020institute.com/free-tools/ CONNECT WITH BILL CANADY Bill Canady: https://billcanady.com/ The 80/20 Institute: https://the8020institute.com/ The 1000-Day CEO: https://1000dayceo.com/ Subscribe for practical conversations about decisive leadership, profitable growth, operational discipline, and building lasting enterprise value: https://www.youtube.com/@billcanady?sub_confirmation=1
Sep 24

Building a Business in Asia: Trust, Cash, and Letting Go | Glenn Grow | EP25

Growing internationally can stretch your cash, your team, and your ability to stay in control. Glenn Grow, founder and CEO of Innovasia, joins Bill Canady to explain how he built a business across Asia through customer problem-solving, local trust, and disciplined delegation. An anchor customer gave Glenn the opportunity to expand—and the obligation to deliver. He shares the cash pressure of importing materials and waiting for payment, how customer needs created an acoustic business, and why local leaders need authority within clear guardrails. His advice to founders: build people who can replace you, protect cash, and do fewer things better. IN THIS EPISODE • Win an anchor customer by solving a specific problem. • Understand the gap between sales and available cash. • Earn trust through presence, respect, and listening. • Delegate daily decisions while keeping shared controls. • Fund growth deliberately and develop your successor. CHAPTERS 00:00 Building across borders 01:11 Winning the anchor customer 04:51 When growth outruns cash 08:47 Solving the next customer problem 13:52 Earning trust across cultures 19:46 Local authority, shared guardrails 22:40 The cost of growing too fast 24:44 What Glenn would change 27:22 Replacing yourself by day 1,000 29:10 Do less, better CONNECT WITH GLENN GROW Innovasia: https://www.innovasia.com/ LinkedIn: https://www.linkedin.com/in/glenn-grow-2594478 FULL TRANSCRIPT AND CAPTIONS On-screen captions are included in the video edition. A separate public transcript is not currently available. FREE CEO TOOLS Business Valuation Calculator: https://the8020institute.com/business-valuation-calculator/ Profitable Growth Scorecard: https://the8020institute.com/profitable-growth-scorecard/ Profit Concentration Analyzer: https://the8020institute.com/profit-concentration/ Price Increase Impact Calculator: https://the8020institute.com/price-increase-calculator/ LBO Calculator: https://billcanady.com/lbo-calculator/ Profit Map Calculator: https://billcanady.com/profit-map-calculator/ All free tools: https://the8020institute.com/free-tools/ BOOK A CALL WITH BILL CANADY Meet with Bill: https://calendly.com/billcanady/check-in Command 100 — talk directly with Bill: https://calendly.com/billcanady/command-100 CONNECT WITH BILL CANADY Bill Canady: https://billcanady.com/ The 80/20 Institute: https://the8020institute.com/ The 1000-Day CEO: https://1000dayceo.com/
Sep 21

Why Profitable Businesses Struggle to Sell | Nitin Khanna | EP24

Can your business run without you? Nitin Khanna of N3 Business Advisors and Bill Canady explore how to build a business buyers can trust. From the vacation test to cash flow and succession, learn to document work and delegate decisions in the first 100 days. IN THIS EPISODE • Test owner dependence. • Track cash, receivables and job profit. • Delegate more decisions by day 100. CHAPTERS 00:00 Introduction 00:59 Profitable vs. transferable 03:10 Three readiness questions 06:26 Five exit paths 08:25 Owner-dependence test 11:12 Return on time 14:51 Preparing for the next owner 18:36 First 100 days: document work 19:56 Cash flow and job costing 24:14 Day 100: delegate decisions 25:09 Family, management or buyer 27:07 Start with a blueprint 28:35 Connect with Nitin CONNECT WITH NITIN KHANNA N3 Business Advisors LinkedIn Mastering the Business of Construction FULL TRANSCRIPT AND CAPTIONS On-screen captions included. A public full transcript is not yet available. FREE CEO TOOLS Business Valuation Profitable Growth Scorecard Profit Concentration Price Increase LBO Calculator Profit Map All free tools BOOK A CALL WITH BILL CANADY Meet with Bill Command 100 — talk directly with Bill CONNECT WITH BILL CANADY Bill Canady The 80/20 Institute The 1000-Day CEO Subscribe to The 1000-Day CEO. Which decisions still depend on you? #ConstructionBusiness #BusinessExit #1000DayCEO
Sep 16

Turn Company Knowledge into Value with AI | Brian McWhorter | EP20

When a key employee leaves, how much of your company's know-how walks out the door? Brian McWhorter, founder and CEO of Bravura-AI, joins Bill Canady to explore how CEOs can make industrial knowledge easier to find, use, and retain—and where AI fits into a private equity value-creation plan. Brian shares an early plant troubleshooting story that predates his AI work, then explains how organizing engineering information can help people solve problems and reduce time spent searching for answers. The conversation moves from his theory of knowledge capital to investment priorities, employee adoption, security choices, and a practical 30-, 100-, and 1,000-day approach. For PE-backed CEOs and operating partners, the central question is how to build useful capabilities that stay with the company. Brian presents knowledge capital as an emerging idea and shares where he believes CEOs can begin putting it to work. IN THIS EPISODE • Why accessible engineering information matters before adding AI • Capturing institutional knowledge when experienced employees leave • Where industrial CEOs can start—and why "just use AI" falls short • Local and cloud approaches to security and deployment • Proving a small use case, expanding capability, and training the team CONNECT WITH BRIAN MCWHORTER Bravura-AI Brian's story LinkedIn FREE CEO TOOLS Business Valuation Calculator Profitable Growth Scorecard Profit Concentration Analyzer Price Increase Impact Calculator LBO Calculator Profit Map Calculator All free tools BOOK A CALL WITH BILL CANADY Meet with Bill Command 100 — talk directly with Bill CONNECT WITH BILL CANADY Bill Canady The 80/20 Institute The 1000-Day CEO Subscribe for practical conversations about decisive leadership, profitable growth, operational discipline, and building lasting enterprise value: What critical knowledge depends on one person in your company—and what would it take to make it available to the whole team? #PrivateEquity #IndustrialAI #1000DayCEO
Sep 5

Why Résumés Miss Your Best Hires | JR Butler | EP19

Most companies say they hire for character. Then they let a résumé decide who gets through the door. What talent are they missing? In EP19 of The 1000-Day CEO, Bill Canady sits down with JR Butler, founder and CEO of Shift Group, to explore how leaders can identify resilience, coachability, curiosity, and team-first drive before a candidate has the credentials to prove it. A former Holy Cross hockey player and technology sales leader, JR helps athletes and military veterans translate their experience into business careers. He shares what conventional hiring overlooks, why potential still needs coaching, and how first-line leaders shape a team's performance. In this conversation: • Look beyond résumés to uncover character and transferable skills. • Recognize when a candidate's strengths can become liabilities. • Define what a successful hire should accomplish. • Close the gap between stated culture and employees' experience. • Develop critical thinking and communication as AI changes work. • Build stronger teams through clear expectations and consistent coaching. For CEOs, founders, and private equity operators, this is a practical conversation about finding overlooked talent and helping it perform. Connect with JR Butler: Shift Group: https://www.shiftgroup.io LinkedIn: https://www.linkedin.com/in/jrbutler/ Hosted by Bill Canady | The 80/20 Institute https://billcanady.com
Sep 3

Founder to CEO: Why Great Technology Still Fails | Heath Naquin | EP18

Great technology does not become a great business on its own. The breakdown often occurs when founders must convert technical progress into investor confidence, customers, and enterprise value. In this episode of The 1000-Day CEO, Bill Canady speaks with Heath Naquin, Senior Vice President of Innovation & New Ventures at the University City Science Center and founder of Forged Catalyst Group. Heath explains why capital is often not the real constraint—and why a company’s structure, leadership, regulatory strategy, and investment readiness determine whether its innovation reaches the market. Bill and Heath discuss: • The difference between raising money and becoming investable • Why capital efficiency is not the same as being cheap • How regulatory shortcuts create delay, rework, and dilution • The corporate hygiene institutional investors expect • Why contracts, intellectual property, and data rooms affect enterprise value • The warning signs that a technical founder may not be ready to scale • Why inventing the technology and leading the corporation require different skills • The question every CEO should ask before deploying the next dollar This conversation is for founders, CEOs, investors, operating partners, board members, and advisors working with medtech, life-sciences, deep-tech, and venture-backed companies. Connect with Heath Naquin: University City Science Center: https://sciencecenter.org/people/heath-naquin Forged Catalyst Group: https://www.forgedcatalystgroup.com/ LinkedIn: https://www.linkedin.com/in/heathnaquin/ Learn more about Bill Canady and The 80/20 Institute: https://billcanady.com/ https://the8020institute.com/

Trailer

The 1000-Day CEO Trailer

Private equity may hold an investment for years—but CEOs and sponsors often begin with a much more urgent ambition: buy it, transform it, and create the winning exit in roughly 1,000 days. That tension is where The 1,000-Day CEO lives. Hosted by Bill Canady, this podcast goes beyond polished board decks to examine how exceptional companies are actually built. You’ll hear the decisions, operating disciplines, leadership challenges, breakthroughs, and occasional lucky breaks behind successful transformations. Some episodes will feature Bill walking through the practical tools, processes, and frameworks CEOs need to accelerate growth and create value. Others will bring you candid conversations with private equity sponsors and the operators living the journey right now—from leaders sprinting toward an exit to those still fighting through year five. This show is for: • Private equity sponsors • Portfolio company CEOs and executives • Operating partners • Business leaders responsible for growth, transformation, and value creation When you’re carrying the number, the clock is already ticking. Welcome to The 1,000-Day CEO. Follow the show and join us for the journey from deal to turnaround to exit.

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.

Creator

Bill Canady
Years Active

2026
Episodes

29
Rating

Clean
Copyright

© 2026 Bill Canady
Show Website

The 1000-Day CEO