How to Tell a Demanding Founder They’re Wrong

Summary

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Run the Numbers – Episode Summary

Episode Overview

Episode: How to Tell a Demanding Founder They’re Wrong
Release Date: July 27, 2026
Host: CJ Gustafson
Guests: Ben Hillman (co-host/producer), Alex Ammerman (A16Z), Shruti Lanka (Public), Kurt (CFO of Clio), Daniel Kang (CFO of Mercury), Adam Ante (Paycor/Paychex), David Lapter (Dashlane)

This episode of Run the Numbers dives into one of the thorniest dynamics in tech: How can a CFO (or any exec) disagree with a visionary, demanding founder—especially when the founder might just be proven right by history? Through famous case studies (the Ballmer/iPhone debacle), interview clips from seasoned finance leaders, and CJ’s reflections on his own journey, the show weaves a playbook for balancing backbone, diplomacy, and trust in high-stakes leadership.

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Key Discussion Points and Insights

1. The Triangle of Doom: Dynamics of Power in the C-Suite

• Scenario: Ben sets up the “triangle of doom,” where the CFO sits at the weakest point compared to the CEO and Board. The central challenge: You have dual loyalties—fiduciary duty vs. reporting line.
  • CJ (01:02): “If you're the CFO, you actually have the weakest spot on the triangle...The board and CEO have conversations all the time that you’re not privy to.”
• Case study: Steve Ballmer at Microsoft laughing off the iPhone, missing the paradigm shift.
  • Ben (01:41): "The CEO was Steve Ballmer. The company was Microsoft…The product was the iPhone."

2. The CFO as the “Truth Teller” (Consigliere)

• Calling a Spade a Spade:
  • CJ (02:32): “In many ways, I think the CFO is looked at as the consigliere of the CEO. It’s their truth teller…You do, I think, get a pass to call a baby ugly or a product ugly if you have to, because you’re making the resource allocations that are attached to it.”
• Real-World Tension: Pushing back on hiring or strategic moves can be “pretty awkward after”—but necessary.

3. Hallmarks of a Great CFO: Backbone and Collaboration

• A16Z’s Favorite Interview Question
  • Alex Ammerman (03:39): “Tell me about a time you disagreed strongly with a CEO and what happened. A great CFO is not just a numbers person but a strategic counterweight.”
  • Shruti Lanka (04:03): “Do you have a backbone?”
  • Alex (04:05): “If your example is not a difficult situation, you probably don’t have a backbone.”
• Pitfall: Surface-level disagreements (budget, “should we go to a conference?”) don’t count—it’s about the big moves: launches, hires, acquisitions.

4. The Dreamer/Realist Dynamic

• Walt and Roy Disney as archetype: Walt with vision, Roy/CFO executing and allocating resources.
  • CJ (06:53): "A CFO or COO many times has to continue to lay track out in front of the CEO, which can be hard...you have to find a way to coordinate resources to execute on that vision."
• The essential tension: Being likable but respected, pushing back but maintaining trust.
  • CJ (07:36): “The best CFOs are liked even when they make non-likable decisions…If you have the trust of your peers to make that call…it means a lot.”

5. Balancing Backbone with Servant Leadership

• Kurt (Clio) on Tactics:

  • Kurt (11:57): “Take your ego and put it in the bottom drawer and shut it hard and really listen and build trust...Founders have almost an allergic reaction to the answer no.”
  • Instead of no, use “help me understand”—make it a joint exploration.
  • Founders must see you as an ally; you’re at their service, elevating decision quality.

• CJ’s Synthesis:

  • CJ (14:02): “It’s really hard to do...to always remember that you are just part of the supporting cast to execute on that vision.”
  • “Robin to their Batman”—founders set the big vision, CFOs build the incremental, tactical plan.

• Knowing When to Push Back:

  • CJ (15:22): “You have to have that backbone when you're faced with a one way door decision versus a two way door decision.”
  • For positive framing and collaborative problem-solving, ego stays stowed; for irreversible, existential moves, backbone comes out.

6. True Influence: Thought Partnership, Not Purse Strings

• Daniel Kang and Shruti Lanka:
  • Shruti (17:09): “I actually don't like this moniker of finance has a seat at the table because you control the purse strings. I think that's the last type of hard power you want...You want to be effective because you’re a thought partner...not their own king of building.”
• Best Finance Teams:
  • Measured not by forecast accuracy, but by cross-functional collaboration, idea-generation, and being approached with “half-baked” ideas.
  • CJ (17:46): "I know I'm being a good partner when my CMO or CRO will come to me with an idea that’s not fully baked..."

7. The Limits and Powers of Finance

• Money as a Lever—but Not the Only One:

  • Quoting Sanoi Torero: sometimes, a small spend unblocks large productivity, but this should be one of many tools.
  • CJ (18:45): "Money is one of the arrows you have. It’s not the end-all, be-all."
  • The role is to think through issues, not just open or close the purse.

• Avoiding the “No Machine” Trap:

  • CJ (20:11): “The bad CFOs...stop at the no, can’t do it, red light. There's always conversation that should be had around risk-adjusted return…”

8. Earning and Using Your Seat at the Table

• Adam Ante:

  • Adam (25:15): “When you're adding value...people want you sitting at their table. And then when you get to the table, you have the right to sort of get into anything you want. And...when you can step into those areas, you add a different perspective.”

• CJ on Entry:

  • Start with fresh eyes—ask “why do we do it that way?”, reflect observations, and earn trust by proactively adding value, not just by position.

• Real Exclusion?

  • CJ (28:36): “It’s cultural at that point...” If the org is not data-driven or wants a passive, reactive CFO, sometimes there’s little you can do.

9. Knowing When (and How) to Speak Up

• David Lapter:

  • (29:55): "Listen, observe, think, speak when it’s really going to be impactful... Speak up if you disagree. Ideally have data-informed reasons for it..."
  • Don’t be the silent minority—regrets come from what you didn’t say.

• Speaking Up Isn’t Just Critique: Sometimes it's providing crucial context/insights, even if it’s outside your purview.

• CJ on Creating a Culture for Dissent:

  • (31:10): “Having forums to share data and information...It should be a series of conversations. That way it’s not just dropping this—‘you did a bad job’—on somebody’s desk.”

10. Full Circle – Culture Beats the Moment

• Kurt (31:57): The biggest mistake is coming in as a know-it-all; respect unknowns and unseen conversations.
• CJ’s Ballmer Scenario:
  • (36:15): “Steve, this isn't an issue of what anybody said today. We have an issue that six months ago, we were not discussing the right data to even know where we stood in the market to make a claim like that...It’s less an indictment on that moment in time and what was said and more an indictment on the culture that was created to live in that warped view of what good performance looks like.”
• Cultural Takeaway: It's not about One Big Argument; it’s about constantly creating space for honest, data-driven discussion, so that mistakes don’t happen in silence.

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Notable Quotes & Memorable Moments

The “Triangle of Doom”

“If you're the CFO, you actually have the weakest spot on the triangle.”
— CJ Gustafson, 01:02

On Speaking Truth to Power

“You do, I think, get a pass to call a baby ugly or product ugly if you have to, because you’re making the resource allocations that are attached to it.”
— CJ Gustafson, 02:32

On Backbone

“Do you have the chutzpah to stand up in a difficult situation?”
— Alex Ammerman, 04:05

On Partnership vs. Power

“I actually don't like this moniker of finance has a seat at the table because you control the purse strings. I think that's the last type of hard power you want...”
— Shruti Lanka, 17:09

On the Bad CFO

“The bad CFOs...just stop at the no, can't do it, red light. We don't have money in the budget. There's always conversation that should be had...”
— CJ Gustafson, 20:11

On Inclusion and Exclusion

“You do not have the right to speak up and give advice on stuff you don't know. But you do have a right to be at the table and be at least a listener to the conversation.”
— CJ Gustafson, 26:45

On Culture and the Consequences of Silence

“You don't want to get to a point where you've made mistakes and then go over and over it in your head asking yourself, what if I had spoken louder?”
— David Lapter, 29:55

On the Root Problem at Microsoft

“We have an issue that six months ago, we were not discussing the right data to even know where we stood in the market to make a claim like that...It’s more an indictment on the culture…”
— CJ Gustafson, 36:15

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Timestamps for Important Segments

| Segment | Timestamp | |-----------------------------------------------------|------------| | Triangle of Doom, C-suite Power Dynamics | 01:02 | | Microsoft/iPhone Case Study | 01:41 | | CFO as Truth Teller | 02:32 | | Backbone: “Favorite Interview Question” | 03:39–04:36| | Dreamer (Walt) vs. Realist (Roy) Dynamic | 06:36 | | “Liked even when not likable” in CFO role | 07:36 | | Kurt (Clio) on Servant Leadership for CFOs | 11:57 | | Balancing Backbone and Servant Leadership | 14:02–15:53| | Daniel Kang & Shruti Lanka: Thought Partnership | 16:44–18:26| | Avoiding the “No Machine” Trap | 20:11 | | Adam Ante: Earning Your Seat at the Table | 25:05–26:45| | David Lapter: Speak Up or Regret It | 28:55–29:55| | Creating Space for Dissent and Better Data | 31:10 | | Kurt (Clio): Biggest Mistakes CFOs Make | 31:57 | | CJ’s Hypothetical: What to Tell Ballmer? | 36:15 |

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Episode Takeaways

• Being an effective CFO (or business leader) isn't about wielding the budget as a club or always pushing back—it's about building trust, listening deeply, and stepping up with backbone in truly pivotal moments.
• The right culture, rather than heroic “lone truth teller” moments, prevents major missteps—and enables honest, ongoing debate.
• Earning your seat at the table is about consistent value, curiosity, and willingness to collaborate—not just formal authority or purse strings.
• The “truth teller” role is essential: If you avoid hard conversations for the sake of comfort, you risk organizational self-delusion and missed opportunities.

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This episode is essential listening for finance professionals and startup execs navigating the tension between accountability, truth-telling, and trust in high-velocity environments.

Transcript

[Ben Hillman]

Cj you have no fricking clue what we're talking about, huh?

[CJ]

I don't know what we're doing, Ben. I don't know why you've called me into your office here. I feel like I'm going to get fired or it's like bring your CFO to work day.

[Ben Hillman]

No, you actually asked me what sort of advice have we talked about if you're working with like maybe a difficult founder or difficult cfo?

[CJ]

Yeah.

[Ben Hillman]

I want to propose a scenario for you. We're back to January 2007. You are the CFO of the most successful software company in the world. Your CEO just went on camera and publicly dismissed a competitor's new product. He called it overpriced. He said it had no keyboard. He said it would never get significant market share. Your data is telling you a different story. Mobile adoption is accelerating. Your competitors hardware margins are strong. Consumer electronics is moving fast. Do you go into his office?

[CJ]

I have a hunch of what company it is because you CEO is larger than life. If I'm guessing who this company is

[Ben Hillman]

correctly, this guy might have some current aspirations of something bigger. Right now for you basketball fans, this

[CJ]

is a common thing with executive presence. It's called the triangle of doom. Right? If you're the cfo, you actually have the weakest spot on the triangle. This is something that Rick Smith, former guest, taught me. And the other two points of the triangle are the CEO and the board. And the board and CEO have conversations all the time that you're not privy to. You kind of have two bosses in a way, right? The CEO is your boss on paper, but you have a fiduciary duty to your shareholders and to your board. And you also don't want to go above either one and offend them. So whenever there's a scenario like this, I try to say, is there something I don't know? And are there other incentives from others involved?

[Ben Hillman]

That CEO was Steve Ballmer. The company was Microsoft.

[CJ]

That is the most expensive phone in the world. And it doesn't appeal to business customers because it doesn't have a keyboard, which

[Ben Hillman]

makes it not a very good email machine. The product was the iPhone and within five years it was the most profitable consumer product ever made. Microsoft's mobile business was essentially over. They eventually wrote off, I think $7.6 billion on their Nokia acquisition and exited the market entirely.

[CJ]

I forgot that Microsoft tried to launch a phone call. Complete tangent. Do you remember when ESPN launched a phone?

[Ben Hillman]

ESPN launched a phone.

[CJ]

I don't know if it send you text, but you could check the scores of sports games. So it's like a crappier version of the ESPN app. And I think the phone only lasted like six months.

[Ben Hillman]

$300 for the phone itself and between $65 and $225 per month for content. Steve Jobs called it the dumbest fucking idea I've ever heard.

[CJ]

But back to your question. I've actually been in the room more often where I've said something and maybe even regretted it because I felt like I couldn't keep it inside of me. I just had to call a spade a spade. And in many ways, I think the CFO is looked at as the consigliere of the CEO. It's their truth teller. You do, I think, get a pass to call a baby ugly or product ugly if you have to, because you're making the resource allocations that are attached to it. I've definitely been in scenarios where I've spoken up and been very happy. I did. And a couple scenarios come to mind around, I think, hiring decisions, where I said to the CEO, I think that was a dumb choice. And then it's pretty awkward after. Is this thing on?

[David Lapter]

Yesterday's price is not today's price.

[Ben Hillman]

You did this interview with Alex Ammerman, who is the general partner at A16Z, this is in June of 2025, and he was talking about his favorite interview question for a CFO candidate. So let's roll the clip.

[Alex Ammerman]

My personal favorite is tell me about a time you disagreed strongly with a CEO and what happened. So a great CFO is not just a numbers person, but a strategic counterweight. We were talking about the strategic mind earlier, and. And this question is important for assessing that one.

[Shruti Lanka]

Do you have a backbone?

[Alex Ammerman]

Do you have the chutzpah to stand up in a difficult situation? By the way, if your example is not a difficult situation, you probably don't have a backbone. Do you have the communication skills to thoughtfully disagree? Do you have the respect and trust of the CEO? What I'm trying to glean is whether the candidate is a pushover and the CEO hopefully does not want to bring on a pushover.

[CJ]

I disagree with my haircut.

[Ben Hillman]

At the time, I was going to say, I'm glad you switched barbers. I'm glad you said that first.

[CJ]

I remember this discussion with Alex because it validated a lot of the thinking that I had around the CFO's role, not just as a fiduciary, but as the person who can call a strike a strike and call a ball a ball. And be honest with everybody there. And the CFO is supposed to have the company's best interests in mind, not their departments. And at times you not only have to tell the CEO something that they don't want to hear, but your peers throughout. Throughout the C Suite. So this is one of my favorite conversations, I think, just on the dynamics between the CEO and cfo.

[Ben Hillman]

So this like interview question, tell me about a time that you disagreed strongly with the CEO and what happened. Is there a version of that answer that may sound good in an interview, but is actually a red flag?

[CJ]

Yeah, I think it would just be around something weak, around budgeting. Like the CEO wanted to go and spend on a big conference. And I said, that doesn't sound like money well spent. Okay, that's table stakes. You should just be able to tell them like, there's no ROI on that. The more complicated things are, like I said, around hiring decisions in the C Suite, it's around launching a go to market product in a new country and having to really expand your workforce there. It could be around an acquisition. I think a lot of these questions often come up around something new coming to the market or you potentially being purchased by another company. CEOs only got into that position, especially founder CEOs, because they've said damn the torpedo so many times and taken these crazy risks that nobody else believed in. So in many ways they're probably looking at you as a cfo.

[Podcast Host / Narrator]

Like, I've outperformed what the market said

[CJ]

I could do 10 times in a row and you're going to tell me that this isn't going to work? No, no, no. You don't get how I got here. That's something that I think is unsaid, that that is hard as the CFO to pull them back and be that counterweight when this person has done something, created something so incredible when the odds many times were not in their favor.

[Ben Hillman]

One of my favorite examples of just that, like sort of dreamer and like realist dynamic is the Disney Company history and how when they first started out, Walt was the dreamer. He was the guy that was like, had the all the ideas. His brother Roy, I guess he was like sort of the coo.

[CJ]

I don't think Roy gets enough credit for executing on Walt's vision in the sense that a CFO or COO many times has to continue to lay track out in front of the CEO, which can be hard. Right. Because you have to find a way to coordinate resources to execute on that vision.

[Ben Hillman]

There's a documentary that's about that Disney renaissance In like the 80s, you know, they were almost taken over in like a hostile takeover type thing. And it was like when Michael Eisner and Frank Wells came in. Michael Eisner was the sort of new Disney type, like, kind of dreamer, but he had Frank Wells. And it was when Frank Wells tragically passed away that, like, things kind of went off the rails a little bit.

[CJ]

That steady hand. Really?

[Shruti Lanka]

Yeah.

[Ben Hillman]

You had sort of a response to this.

[CJ]

I don't remember my response.

[Ben Hillman]

I want to see what you, what you say here.

[CJ]

I think in a lot of ways the best CFOs are liked even when they make non likable decisions. And what I'm trying to say, I think is like, you're often put in these positions that are inherently disagreeable, but if you have the trust of your peers to make that call and they're like, I didn't like the outcome of that decision or exactly like where your mind was at, like with going international. But like, I respect where you're coming from and I appreciate you pushing back. Like, that means a lot.

[Ben Hillman]

You still feel the same exact way. Is it worth even going deep on that?

[Podcast Host / Narrator]

Yes.

[CJ]

And I've come to appreciate the ability of a CFO to be disagreeable more and more as I've talked to an increasing number of podcast guests. It's against your human nature to not have people like you. Like, we started off in tribes, right, where if you weren't liked, you get pushed out and you probably die. Get put in these positions where you have to fight against that human nature to be liked by others around you and the ability to just lock in and give the right answer for the company at the time. Maybe not for the people around you in terms of how they see the business and world in that moment. Makes you such a better exec, and I really respect it. Hey, thanks for listening. We'll be right back after a word from our sponsors.

[Podcast Host / Narrator]

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[CJ]

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[Podcast Host / Narrator]

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[Ben Hillman]

So this next clip is actually from Kurt from Clio. He's still the CFO of Clio. This clip was from December of 2024. He talks a little bit about maybe not the complete flip side of what we've been talking about here, but he says something here that I think you'll really appreciate. I want to let him say it. I don't want to spoil it for you.

[CJ]

Are there any strategies for working with founders and empowering them from. From the CFO seat?

[Kurt (CFO of Clio)]

Yeah, there's a couple. One is take your ego and put it in the bottom drawer and shut it hard and really listen and build trust. I found that founders are an incredible source of information, and they have very compelling perspectives on business decision making, whether it's compensation to new products. But you got to find a way to get it out, and you've got to ask the right set of questions, and it's gotta be Q and A based and conversation based. Because the best way I found is founders have almost an allergic reaction to the answer no. Like, so, you know, take a conversation. You're saying, like, no, you shouldn't do it that way, like, as a cfo, okay, well, that just set off an alarm bell, and that ends up, you know, creating all kinds of friction as you continue to go through the conversation with the founder as opposed to, help me understand, help me understand. Let's get to the bottom. What are you really trying to do? What are you trying to do?

[CJ]

Help me.

[Kurt (CFO of Clio)]

Have you thought about maybe approaching it from this perspective? Because it would, you know, add this, this, and this. Or is that an issue? You do have to really think about how you're going to approach these issues, because the founder has to see you as an ally and has to trust you implicitly. And three is, you're not in this role, especially with founders, to take the limelight.

[Shruti Lanka]

You, you, you.

[Kurt (CFO of Clio)]

You're here to propel. I mean, I talk about it as at service leadership. Like, you're at the service of the founder. You're at the service of the executive. Like the finance leader is to elevate everybody in the company to make better decisions to achieve what they need to with the resources that we have and similarly with the board. And so you've got to kind of have that mindset with founders. And I can, you know, I can tell you just avoid a lot of challenges if you. If you adopt that.

[Ben Hillman]

Take that ego, cj Put it in the bottom drawer. What do you think?

[CJ]

It's really hard to do, especially when you're around CEOs with this sphere of influence and the energy that's dynamic and contagious, to always remember that you are just part of the supporting cast to execute on that vision. Like we said before, founders are visionary in the sense of knowing where they want to push the company and where they want to go and what they want the angle to be. What they may lack and where a CFO can help a lot is the intermediary steps to do it. They understand that they want to be number one in the market with this many products by this date. But how do you bridge the gap in between? The CFOs can be tactical in helping to get there. I think Steve Jobs almost never asked people or customers like what they wanted in a lot of ways. And the same thing with Henry Ford. He said people would have just asked for faster horses. And so a lot of times it's instead of saying no to a founder, it's re pivoting by way of using questions to better understand what the motivations are and where they're trying to go. In the end, maybe that that is you have to create a car instead of using a horse to ride to their destination.

[Ben Hillman]

This seems like there's like an inherent tension in this advice because earlier we were talking about like have some chutzpah, have some backbone, but now Kurt is talking about taking a backseat, keeping that ego know in the bottom drawer.

[CJ]

I think you have to have that backbone when you're faced with a one way door decision versus a two way door decision. Right? Like you have to stand up and let your opinion be heard and say I think that's a good idea or bad idea. But what I think he's saying here is more in the positive framing of the CEO wants to drive the business to a positive business outcome. How do you help get there? Put your ego away. You are the Robin to the Batman. How do you help execute upon that? So I think they're both true under different circumstances.

[Ben Hillman]

Is it a matter of like uncovering that second door?

[CJ]

This is going to come across like a generalization. It's definitely not true in every scenario. I find a lot of CEOs think in terms of binaries of like we're going to do this and get to this point. And it's like black and white in terms of like where they want to go with things. There are often shades of gray that get uncovered along the way or there are different paths you can take to achieve similar outcomes. So to your point Ben, I think it is finding those different variations by way of asking questions of what we're trying to achieve.

[Ben Hillman]

So next I want to pivot to a clip where you're talking to Daniel Kang. And at the time it was December of 2024, he was the VP of Finance at Mercury now he's the CFO of Mercury, so definitely some valuable information for folks that maybe aren't in the C suite yet. This is coming from a guy that said this at the time and he finds himself in the CFO seat now.

[CJ]

I do think that finance has a bigger voice sometimes in other groups though, and this is, you know, just, it happens that way. I'm not saying it's fair, but because you're helping the CEO a lot of times with that initial tops down cut or you're doing the long range plan, you, you can have your fingerprints on the org. Now I'm not saying that like it should be viewed as a financial exercise per se, but you do have a, like you said, a voice at the table of shaping it the way that

[Shruti Lanka]

finance can thus plug in. I, I actually don't like this moniker of finance has a seat at the table because you control the purse strings. I think that's actually like the last type of hard power that you want to exercise to be effective in your job. You want to be effective in your job because you're being a thought partner and like being able to hopefully allocate resources and partnership, assuming that everyone has the right intention to buy and think about the company, not like their own individual king of building, which does happen obviously.

[CJ]

That's so well said. Like if people are only listening to you because you can say yes or no because you have money, it's like they really respect you.

[Shruti Lanka]

For sure. For sure.

[CJ]

I, I say that like I, I know that I'm being a good partner when like my CMO or CRO will come to me with like an idea that's not fully baked yet. Right. But they want to bounce it off me. And it's not because it means I've broken through them thinking that I'm, I'm there just to, to like judge something as like a binary investment decision. Like they see me as a thought partner, like oh, I can bring them like this half baked idea and we can, we can jam on this to see if it has legs.

[Shruti Lanka]

I think the best marker of a successful finance team is when you do see those type of cross functional pools for collaboration. I think that's a much bigger marker than like forecast accuracy or some of the silly things that finance teams try to say.

[Podcast Host / Narrator]

Okay, Ben, these clips are such a throwback.

[CJ]

Have you realized that the background behind me has changed three times from the same seat in the same room?

[Ben Hillman]

I know. Let this be proof that you're, you're not actually an AI guy. You just Got a little bit more budget, so don't use the purse strings as, as your seat at the table. I think is the summary of what Daniel's talking about there.

[CJ]

I've also heard the opposite take here too, and it was from Sanoi Torero, CFO and CEO now of Envoy. He basically said, it's funny, finance has this power to also make certain problems go away with money. And he wasn't saying bribe people. He was saying money sometimes can cause problems and you can use that with discretion. Let's say you have someone who gets paid $200,000 a year and they're being blocked from 50% of the productivity because of a $10,000 problem. Use your magic wand and make that go away with $10,000 worth of spend. However, to Daniel Kang's point that that shouldn't be the only reason they're coming to you for the money. They should be coming to you for helping to think through whatever issue it is that they have. And money is one of the arrows you have. It's not the end all, be all. They should be coming to you because they think of you as someone who can clearly think through a scenario that involves resource allocation, it involves pricing, involves whatever it may be, and they trust your opinion on it. When I say trust your opinion, it means they're coming to you because they don't think they're going to be judged. Right? Because the CFO does sit in this funny seat where they could go to the CEO and say like, hey, I don't think CMO is pulling their weight or doing a great job based on the numbers I have. They also think that you're going to jam out with them and give more back than, than what they gave to you in terms of, hey, can you think through this?

[Ben Hillman]

It seems like there's rarely a scenario where you're going to be like, sorry man, just don't have it in the budget.

[CJ]

The bad CFOs and bad finance professionals will just stop at the no, can't do it red light. We don't have money in the budget. There's always conversation that should be had around what is the best risk adjusted return on the capital we have. And also it goes back to what we were saying with the CEO before. What are we even trying to achieve with this? Because it may not even be that we don't have the money. It just may be we don't have the right people working on the right stuff. And it's, and it's changing the mix of people and software and now Tokens. Hey, thanks for listening. We'll be right back after a word from our sponsors.

[Podcast Host / Narrator]

I got news for you. Thanks for watching. The ERP category is finally getting disrupted and if you haven't heard of Rylit yet, please pay attention. It's the AI native ERP built specifically to replace netsuite and it's already won over hundreds of finance teams. Their mission is to make the zero

[CJ]

day close a reality.

[Podcast Host / Narrator]

And they're actually doing it. We're talking teams closing the books at 1:35pm on the first day of the month. Companies like Windsurf, Mercore and hundreds of others run their entire finance stack on revenue recognition, Close management, Multi entity, Native Stripe and Salesforce integrations. Woo everything a scaling company needs. They've got 5.0 start 5.0wow 50 stars on G2. They're backed by A16Z and Sequoia. Heard of them and CPA led implementations that get you live in 45 days. That is simply unheard of in the ERP space. If your books aren't running as fast as your business, check out RIT. Book a demo at r.comcj that is all r-I l l e t.comcj that's me. Everyone in finance is adopting AI right now.

[CJ]

There's a problem because there are a dozen disconnected tools.

[Podcast Host / Narrator]

You got one for revenue, one for ap, one for close. And each one of these needs training and documentation and the expertise to run them lives in your team's heads, not your systems. Maximore takes the opposite approach. One autonomous finance platform for the whole operation. Order to cash procure to pay the close cash management reporting running on a single unified finance context that pulls from your ERP billing banks, even email and Slack. Maximore runs on self learning agents that learn how your team already works. No prompts to write, no workflows to build, nothing to document. Every output is audit ready and when a call needs human judgment it escalates for review because the agents optimize, not just execute and your KPIs improve. I'm talking about DSO working capital cash conversion. In fact, one PE back customer cut

[CJ]

their clothes in half.

[Podcast Host / Narrator]

Their audit findings from 7 to 0. Back office cost down 70% and in six months no ERP rip and replace. You pay only for real outcomes, not seats. See it@MaxMoor AI that is max I m o r AI. The CFO role has evolved faster than

[CJ]

the tools built to support it.

[Podcast Host / Narrator]

Most finance teams are still running infrastructure designed for a job that no longer exists. The reporting, the reconciling the close that bleeds into the next month or quarter. That's not finance. That's overhead with a really crappy title. And the cost isn't just your time. It's everything your best people aren't doing

[CJ]

while they're buried in it.

[Podcast Host / Narrator]

Agentic finance shouldn't multiply your output. It should eliminate the work that was never worth doing in the first place. And that's why I run mostly media on Brex, an intelligent finance platform with AI powered agents that capture expenses, automatically, enforce policy before the spend happens, and close your books in minutes instead of weeks. 35,000 companies like OpenAI, Coinbase, Anthropic and Doordash already run on Brex. It's time to get Brex AF. Learn [e-mail] metrics so next up, we've

[Ben Hillman]

got a clip from Adam Ante. At the time he was the CFO of Paycor. This was in June of 2024. Now he's the SVP and managing director at Paychex. Paycor was acquired in April of 2025, so a little bit of growth for him. I know you've gone through going public and you've. You've gone through a company being acquired as well, correct?

[CJ]

I have not gone through the process of going public. We thought we were going public just like every other company during the Zerb era. But I've gone through the process of being acquired. And if you're acquired, the CFO and the chief legal officer and usually the head of HR are the first three out the door.

[Ben Hillman]

If you're acquired and you are the CFO of a company and you go to that next company, you're probably not going to get that same title. Maybe even like, it may appear on paper, like a demotion of sorts, right?

[CJ]

Well, usually they don't keep you around because they already have a cfo and ostensibly it's a bigger company if they're acquiring you. There are a couple scenarios, I think, where, like the minnow swallows the whale. One example that I can think of is Matt Hudson. Coda was acquired by Grammarly, much bigger company, and the CEO of Coda became the CEO of Grammarly and the CFO of Coda became the CFO of Grammarly, which was neat to see.

[Ben Hillman]

Let's let Adam rip here.

[CJ]

Adam, do you think finance people pigeonhole themselves into narrow roles? Are there examples of like, jumping into places that you didn't belong in your career that actually paid off?

[Adam Ante]

I think finance people do that in spades. They're so good at it. Finance people, accounting people, people with that background, I don'. If it's because it's just where they're comfortable is, you know, staying in numbers and staying in the financials, or if they don't realize the opportunity that they have to really take things to the next level. But I, I do see, you know, folks sort of shrink away from the opportunity to, like, really press into the business and show up in places that, yeah, maybe they don't have any right to be, but there's an opportunity. And I think it's, it's, it's cool. Like, folks always want a seat at the table. And when, when I hear people say, like, I want a seat at the table or they're not giving me the seat at the table, I think you have to, like, look at yourself and say, like, well, first, are you adding value to these conversations? Because when you're adding value and you're killing the things that you're doing, people want you to be sitting at their table. And then when you get to the table, then you're like, I have the right to sort of get into anything I want. And you got to be respectful. Of course you don't want to. Just like, you know, you're a finance person, by the way, you haven't sold software yet, but, you know, when you can step into some of those, those areas, you can add a different perspective. And I think that's what's really valuable is when you can come with a different perspective, then everybody can make better decisions. And, and I've been sort of lucky enough to get into those opportunities, you know, quite a few times in my career.

[Ben Hillman]

I feel like there's something that's, like, uncomfortably honest about this take that. Is there not giving me a seat at the table? Almost always this self diagnosis, does it come from, like, reflection inwards?

[CJ]

Something super empowering, that Shruti Lanka CFO of Public told me, is that the CFO has the right to sit in on any meeting within the company. Right. It's all within your purview. Do not feel restricted. You do not have the right to speak up and give advice on stuff you don't know. But you do have a right to be at the table and be at least a listener to the conversation. For your awareness made me feel pretty good around not pigeonholing myself. And what Adam gets at here is you earn your way into conversations outside of the typical finance realm by proving value. Right. And it also links to what Dan Kang said around being a good business partner, thinking more broadly about the Departmental specific problems that someone's trying to solve and using whatever in your arsenal to help them achieve that.

[Ben Hillman]

You've started a company, it's your first 90 days at the company. What is adding that value actually look like in, let's say the first 90 days when you may not have earned that trust yet.

[CJ]

It's coming in with a fresh set of ears and eyes to an org that has been doing stuff in a certain way because inertia is hard to move. Hey, how are we paying sales reps here? Walk me through it. And then you're looking around like, well, that, well, why do we do it that way? Oh, because so and so used to work here and we did that. And so much of it is just listening, then reflecting back what you heard. It's funny, even sometimes when you say something to a sales leader, a cmo, you're just stating what your observations are because those are usually your closest thought partners, right? As a cfo outside of the CEO, they're like, oh, and just hearing that can, can make them think about it differently. You're, you're not even giving suggestions, right? You're just reflecting back what you're hearing. And so I think there's a lot of value, not just for CFOs, but anybody coming into an org in terms of absorbing what's going on and then trying to figure out why things are done a certain way. Then I think you can start to make suggestions on how you might change things.

[Ben Hillman]

Is there a version of this where like the CFO is genuinely being excluded and it's just not their fault?

[CJ]

It's cultural at that point. I think it's because it's not a data driven organization or they think that the CFO is reactive and just in this back room they're going to write down what the results were after the fact, right?

[Ben Hillman]

So next up we have a clip from David Lapter. He's the CFO of Dashlane. I believe he's like a five time cfo.

[CJ]

He's going to be in the baseball hall of Fame for CFO someday.

[David Lapter]

And I've taught my kids that lesson. Like that's something that stays with me. Just listen. You don't have to speak every time a question is asked. You don't need to participate in every discussion. Listen, observe, think, speak, when it's really going to be impactful. Right now on the flip side, I said speak up and speak up is about the mistakes I [e-mail] for example. But I think we all make those mistakes which Is, you know, especially like let's say as a high functioning executive team, if there's something that's being said or contemplating a contemplated especially before a decision is made, speak up if you disagree. Ideally have data driven data informed reasons for it. Don't sit back and say, well, I'm going to be the minority speaking against it or I'm going to be the only naysayer. No, no, no, say your piece. You don't want to get to a point where you've made mistakes and then go over and over it in your head asking yourself, what if I had spoken louder?

[CJ]

For the context of listeners, Fab.com was one of the highest funded, kind of a marketplace for buying goods around. The dot com boom, like many other companies, did not have the best ending. They were burning an insane amount of money to keep the company going in comparison to the revenue it was bringing in. I believe he's reflecting on are the decisions they made around hiring people and the product roadmap. You know, I've always spoken up about the hiring stuff, but if you're working with a technical leader, it can be daunting to question some of their decisions around the roadmap because you're not technical. David's approach is he's bringing data to the conversation when it is something that, that may be outside the purview of a cfo just to arm people with the correct information to make those decisions, even if you're not the person to make them. So speaking up, Ben, I don't think always means speaking up to say, I don't agree with something. Sometimes speaking up can be to provide context and numbers that would better serve the leaders around you.

[Ben Hillman]

We'll get back to the Microsoft example in a second, but kind of going back to that, like how do you build that kind of culture where the CFO saying something like, I think we're wrong about this, I think this was a mistake is welcomed rather than punished.

[CJ]

Having forums to share data and information because nobody likes to have just thrown on their desk, this is wrong, this is bad. You made a bad choice. It should never come to that point. It should be a series of conversations around data in the context in your market scenario, especially as it relates to your competitors. And then the macro of where you can receive funding. That way it's not just dropping this, hey, you did a bad job on somebody's desk. You have to have a culture where these discussions have a forum. Maybe that's a Monday exec meeting call. Maybe it's a series of five Key data points that everybody agrees are the most important to operate the business and they're sent out every Tuesday at a certain time and they're, they're very accessible to people.

[Ben Hillman]

So let's bring it back to Kurt from Clio now. He's, he's got a little bit of a full circle for us.

[Kurt (CFO of Clio)]

I think that's one of the biggest mistakes CFOs can make. I think most of us get it in the, in the private world and in the venture backed world that that's the way things operate. But it's, it's really important that you don't come in as a know it all and you know, full of your own self ego and believe that you have all the answers because there's some things that you just may not know that the founder wants to drive towards or there may be conversations going on between a board member and the founder that you're just not a part of. And so, you know, approach everything with that growth mindset and to get your issues heard. Otherwise if you come in and say, look, you got 10 problems, buddy. And, and you know, there's big issues on the horizon, like 99% of founders will just shut down on that. We're left alone.

[CJ]

Right.

[Kurt (CFO of Clio)]

To solve those problems.

[CJ]

You never want to fail alone either.

[Kurt (CFO of Clio)]

Yeah, yeah, exactly.

[Podcast Host / Narrator]

That's crazy.

[CJ]

I didn't know that this clip was going to be in here. When I started. The top of the podcast was talking about the triangle and you being in the weakest position as a cfo.

[Ben Hillman]

The answer isn't always to push back and it isn't to never push back. So how do you know when you've kind of earned that right to push back?

[CJ]

Before you push back, you have to seek to understand. That's what Kurt is getting at here. It's the first principles of why are they trying to do this thing right. I think you also gain trust from showing somebody that you have a genuine interest in their business.

[Podcast Host / Narrator]

Also, I hate that we can't use

[CJ]

the word genuine or genuinely anymore because of ChatGPT. People think that you're reading off a script, which I'm not. But that is how you earn trust through curiosity. That shows people that you're invested in their business and you seek to understand

[Ben Hillman]

the failure to speak up. Maybe it's initially comes from fear, but it seems like it's more nuanced than that.

[CJ]

I think it's the social dynamic part of not wanting to call somebody's metric ugly. I've written about this before too. It was called Beware of all green dashboards, which I think is a problem that CFOs will get into where they're measuring something they know intuitively has lost its connection to the ground truth of the business. But they continue to do so because the metric was invented by somebody a while ago and they did things a certain way. But they continue to cite this all green dashboard because they don't insult anyone. It goes back to the tribal tendency of wanting to be accepted. And if you challenge something, people inherently tie it back to their personal worth. Oh, am I bad at my job? And so I think that's what a lot of us avoid. You get around that by having that culture where you're constantly discussing things. And that can't be a check the box exercise either. It has to be a scenario where people lay the business on the table for others, for others to understand.

[Ben Hillman]

Before we started recording, we were talking about how we report metrics. And I felt comfortable coming to you about, like there was this just sort of thing that was going on that we couldn't really trust. I understand this may reflect on. On myself, but I just want to make sure that you have all the information and hopefully we're on the same page as well.

[CJ]

Oh, totally. I mean, like, there's so many analogs to dealing with somebody who's maybe in front of the marketing team showing a pipeline number and it's 2.5x instead of 3x and they measured it wrong or investment, you put in those are the right numbers, but didn't pan out well. As the cfo, not great. If you jump down their throat and just yell at them, that doesn't actually solve anything. In fact, what you're doing is you're cutting off your stream of information to make future decisions. So it may make you feel emotionally better in the moment to yell at somebody, but what you're actually doing is harming downstream your ability to make better decisions because that person is not going to come to you anymore. Right. They're going to avoid it at all costs.

[Ben Hillman]

Let's come full circle completely here. We started this episode out. Steve Ballmer, he was talking about the iPhone. And the question that was hanging over everything that we've talked about today is whether anyone in that building could have said the hard thing and actually have been heard. So we know now what Kurt would say about keeping ego in the bottom drawer. We know what David said, the consequences of staying silent. We know what Alex Immerman looks for in a CFO candidate when he asks about the time they disagreed. With the CEO. We know Adam Ante thinks about the seat at the table being earned, not assigned. Let's flashback. It's January 2007. You, CJ, you are the CFO of Microsoft. Bomber just went on camera and he laughed at the iPhone. You know what? You know, you've got the relationship. You've earned that trust. You put your ego in the bottom drawer. What do you walk into his office and say?

[CJ]

I would say, Steve, this isn't an issue of what anybody said today. We have an issue that six months ago, we were not discussing the right data to even know where we stood in the market to make a claim like that. It's not a problem of what was done today. It's how did we arrive at this point where nobody felt comfortable saying, this is the current traction we have with this product. This is the investment we've made in the product roadmap, and these are the metrics that we use to judge success. It's less an indictment on that moment in time and what was said and more an indictment on the culture that was created to live in that warped view of what good performance looks like.

[Ben Hillman]

And he's just screaming, developers, Developers, developers.

[CJ]

Sweating profusely on stage, Developers, Developers. Developers. Developers. Developers, Developers.

[Ben Hillman]

I feel like you kind of have to throw the ESPN phone example at him of like, look, they weren't. They weren't wrong. They were just early.

[CJ]

You can be wrong and early, but it's better to. To have those conversations even earlier.

[Ben Hillman]

Any other parting thoughts before we wrap?

[CJ]

I love this, man. This was a lot of fun. It was a blast from the past, too. Just to watch how much the podcast has developed, shout out to you and Steve for continually improving the quality of this. It's come a long way, and at the same time, the guest wisdom is evergreen. It's still so pertinent even in today's world. So, so much has changed, I think, in terms of how we produce the podcast, but it's just so valuable to look back on these lessons. So great job.

[Ben Hillman]

Thanks, man. And it's. It's really cool seeing how pretty much every guest we talked about today, it wasn't cherry picked as far as what their status was currently as a cfo. Truly, every guest that we talked about is either still in the seat that they were when we talked to them, you know, 18 months ago, or in a better seat. Yeah, a better seat. So it's cool.

[Podcast Host / Narrator]

Ear on the numbers is a mostly media production. Yelling an intro by Fat Joe. Artwork by Meg Delesandro.

[CJ]

Show is executive produced by Ben Hillman.

[Podcast Host / Narrator]

Nothing said on this podcast is intended to be business or investment advice. It's the sole opinion of me, a guy who feeds his dog way too much ice cream and has a history of net operating losses.

[CJ]

Lol.

[Podcast Host / Narrator]

If you like this podcast, hit subscribe

[CJ]

and give us five stars.

[Podcast Host / Narrator]

It will take like two seconds and our algorithm overlords love it. Drink water, call your mom and have a great day.

[David Lapter]

Peace.