How to Tell a Demanding Founder They’re Wrong

**Ben Hillman** (0:00)
CJ, you have no freaking clue what we're talking about, huh?

**CJ Gustafson** (0:02)
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 gonna get fired, or it's like bring your CFO to work day.

**Ben Hillman** (0:09)
No, you actually asked me what sort of advice have we talked about if you're working with like, maybe a difficult founder or a difficult CFO. Yeah. I wanna 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 competitor's hardware margins are strong. Consumer electronics is moving fast. Do you go into his office?

**CJ Gustafson** (0:49)
I have a hunch of what company it is because the CEO is larger than life if I'm guessing who this company is correctly.

**Ben Hillman** (0:56)
This guy might have some current aspirations of something bigger right now for you basketball fans.

**CJ Gustafson** (1:01)
This 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** (1:41)
That CEO was Steve Ballmer. The company was Microsoft.

**Steve Ballmer** (1:45)
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 makes it not a very good email machine.

**Ben Hillman** (1:53)
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 Gustafson** (2:09)
I forgot that Microsoft tried to launch a phone. Complete tangent. Do you remember when ESPN launched a phone?

**Ben Hillman** (2:13)
ESPN launched a phone?

**CJ Gustafson** (2:15)
I don't know if it's any text, but you could check the scores of sports games. So this is a crappier version of the ESPN app. And I think the phone only lasted like six months.

**Ben Hillman** (2:23)
$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 Gustafson** (2:32)
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.

**Alex Immerman** (2:49)
It's their truth teller.

**CJ Gustafson** (2:51)
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. I've definitely been in scenarios where I've spoken up and been very happy I did. And a couple of 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?

**Steve Ballmer** (3:15)
Yesterday's price is not today's price.

**Ben Hillman** (3:27)
You did this interview with Alex Immerman, 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 Immerman** (3:39)
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 this question is important for assessing that.
One, do you have a backbooth? 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.