Tom is joined by Evan Campbell, author of Adapt to Win, to explore why strategy so often fails in execution. Evan explains how strategy decay, organizational inertia, artificial precision in budgeting, and excess work in process prevent companies from adapting and investing effectively. He discusses the CFO’s role in aligning capital with strategic outcomes, using OKRs to create vertical and horizontal alignment, and applying venture capital principles to fund, evaluate, and stop initiatives. Evan also shares lessons from his experience as an Airborne Ranger and Green Beret on empowered leadership, command intent, and building organizational capability. Finally, he reflects on reinvention across his career in the military, technology, consulting, authorship, and ranch life.

Guest quotes:
“ All of the day-to-day chaos of the marketplace and the sales pipeline and all the emergencies and noise in the organization and conflicting priorities and goals of everybody in the organization drowns out the strategic signal of leaders' intent. And leaders have to put energy into the system to keep the clarity of that signal above the noise.”

“If your strategy has any creativity or innovativeness or significant growth objectives in it, you have to force the organization to make that change. The CFO is crucially important in both getting that strategic message through and getting things moving in a new direction.”

“Because we didn't deploy the strategy with clarity, we don't have that steel thread of objectives and measures that allows us to show that we're making the right investment decision. You fall behind competitively because you're not funding innovation or things that are disruptive or drive competitive advantage.”

Links & Resources:

Connect with Tom Gavaghan

Connect with Evan Campbell

Learn more about Kyriba

Read Adapt to Win

YouTube Timestamps:

00:00 Show Intro and Guest Overview

04:09 When does strategy become an investment allocation decision?

07:26 The CFO’s role: why agility and control aren’t opposites

09:17 Strategy decay: why execution is so hard to get right

12:25 Spotting decay early: strategy deployment and execution governance

16:04 Funding long-term bets that lack short-term ROI

19:29 Measuring the unquantifiable with OKRs

22:22 The killer feature of OKRs: horizontal alignment

24:57 Making trade-offs and knowing your true capacity

27:42 Killing zombie projects: creating a culture where stopping is a good thing

31:40 Moving beyond the traditional budget: lean portfolio management

34:50 How leaders know when it’s time to change strategy

37:47 Leadership lessons from his time as an Airborne Ranger and Green Beret

42:15 Where to find Evan Campbell and closing thoughts

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Tom is joined by Cruz Gamboa, a 25-year Fortune 500 finance veteran turned fractional CFO and founder of Ascend Growth Ventures and ScalingCFO.io. Cruz explains why “just grow sales” becomes dangerous as companies scale, how the “cash void” can hide liquidity problems behind a healthy P&L, and why management teams must identify their biggest constraint before pushing for more growth. He also discusses the core financial practices every founder-led company needs, whether AI can replace the CFO, and why judgment, leadership, communication, and storytelling will matter more than ever. Finally, Cruz reflects on golden handcuffs, career identity, and knowing when it is time to make a change.

Guest quotes:
"When you scale chaos, chaos scales."

“Golden handcuffs are psychological, not just financial.  If we hate our jobs, if we hate our reality, if we hate our situation that we're in, we have two options. We either reframe in the way that we see what we do or we make a change.”

“ When you change the way you look at things, the things that you look at change. This is quantum physics.”

Links & Resources:

Connect with Tom Gavaghan

Connect with Cruz Gamboa

Learn more about Kyriba

Learn more about Ascend Growth Ventures

Learn more about ScalingCFO.io

YouTube Timestamps:

00:00 Show Intro and Guest Overview

02:22 The "cash void": when "just sell more" becomes bad advice

04:58 Where cash actually hides: the operating vs. liquidity business

08:20 "When you scale chaos, chaos scales"

09:39 What has to be true structurally before pulling the growth lever

13:20 The theory of constraints: finding the business's real bottleneck

15:56 Can AI replace the CFO?

20:23 Advice for young finance professionals in the AI era

22:58 Productizing ScalingCFO: checklist-driven client methodology

27:15 Why CFOs get left off the table: leadership and ego

31:12 The #1 CFO differentiator: soft skills and communication

33:16 Leaving too late: golden handcuffs and knowing when to go

40:30 What resonates most with his 30,000+ newsletter subscribers

42:47 Book recommendation: Think and Grow Rich by Napoleon Hill

44:12 Where to find Cruz Gamboa and closing thoughts

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Tom is joined by Patrick Villanova, CFO of BlackLine. Patrick shares how his path through 15 years at PwC and BlackLine's own controllership shaped his accountant's-eye view of risk, and how that background informs everything from platform strategy to M&A. Patrick digs into the real math behind build-versus-buy decisions, why private company valuations still haven't caught down to depressed public multiples, and why he's convinced this disconnect can't last. He also explains how BlackLine is deploying AI agents cautiously and deliberately — keeping a human in the loop at every step — and why that same "lean in, but verify" mindset is exactly what he'd tell any accountant or CFO trying to future-proof their career.

Guest quotes:
“ With any technological disruption, there are winners and losers. Those companies that avoided it or were afraid of it or didn't believe it, most of them went the way of the dinosaur.”

“Trust is something that takes years to build up and a nanosecond to destroy. We're bringing our customers along, building that trust, giving them a sampling, and then once we've established that, you have the S-curve of adoption that we've seen multiple times in history.”

“ The more diverse opinions you can get from a talent perspective within your culture, within your organization, the stronger your ultimate product and platform will be.”

Links & Resources:

Connect with Tom Gavaghan

Connect with Patrick Villanova

Learn more about Kyriba

Learn more about BlackLine

YouTube Timestamps:

00:00 Show Intro and Guest Overview

01:05 Patrick's background: BlackLine, PwC, accounting roots

02:03 BlackLine's evolution beyond financial close

03:19 Studio360 as the connective data layer

04:43 Single data source as the key to safe AI agents

05:32 Point solution perception vs. broader platform value

08:34 Why BlackLine stays ERP-agnostic

09:35 The BlackLine-Kyriba partnership model

12:24 Build vs. buy: weighing cost, speed, and talent

15:22 Why private valuations remain disconnected from public multiples

17:46 Engineering productivity gains from AI at BlackLine

19:10 Why "just build it" often underestimates true cost of ownership

23:22 Multiples: 2021 peak to the post-AI-narrative reset

26:53 The reckoning over real AI token costs

30:53 Balancing AI speed with accuracy and trust

34:35 Building customer trust through gradual AI adoption

36:07 Advice for CFOs resistant to change

39:38 Why evaluating security and partnerships matters as much as software

41:20 Advice for young finance professionals in the AI era

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