I Hate How Great IRL Is
I guess I should go
Get revenue recognition right, and no one notices.
Get it wrong, and it’s your name on the 10K.
As a CFO, I know how high the stakes are. Rev rec isn’t just an accounting issue—it’s a risk management issue. We created this free report to highlight the top revenue recognition challenges CFOs are facing in 2025—and what the right solution should look like to stay compliant, efficient, and out of the headlines.
You might not know this about me, but despite making media my living—with a newsletter and a podcast—I’m a raging introvert.
Like many CFOs, getting me out of my desk chair and out to an event is a struggle. And if I have to (gasp) host an event? Forget it. The anxiety kicks in:
No one will show up.
I’ll say something stupid (to the people who didn’t show up)
I’ll be wiped out the next day and useless at work.
The irrational thoughts abound.
It’s probably why my favorite non-work activity is running—because it’s physically difficult for anyone to talk to you.
But damn. Every time I actually go to a conference, a happy hour, or a CFO dinner, it’s 10x more rewarding than I expected. Something great always comes out of it—whether it’s a new podcast guest, a sponsor, or a friend.
And yet, the inertia is real.
I’m writing this because I know there are plenty of finance folks who have to push way outside their comfort zones to show up in real life. Networking isn’t exactly second nature for those who wear both a belt and suspenders to work—only to then have to say no to more things than they say yes to.
So, yeah…
I’m coming off the high of attending Operators Guild’s first CFO event. I’m shocked at how well it went. And how many genuine moments I shared with some of the best people at their crafts.
Maybe this is a selfish post—trying to document for myself the merits of getting out there. Something I can turn back to when I get invited to something and rationalize staying home to write something with my dog while listening to early 2000’s gangster rap music instead.
Some of the cool stuff that came out of this trip:
• A new podcast sponsor
• A legendary podcast guest
• An angel investment opportunity
• Career advice
• A benchmarking idea
• Free Miller Lites
So next time you’re dreading travel or, god forbid, public transportation (I say this as I ride something called BART?), remind yourself of the moments that happen between the moments.
You can’t predict the conversation that sparks on the way to the restroom during a conference break. You can’t schedule the authenticity of meeting people.
I got into a groove of thinking I could recreate these experiences over Zoom (or Riverside, since that’s where I do my podcast). But my deepest relationships have been built in the hallways between hotel ballrooms and dive bars in San Francisco.
So yeah.
As a safari guide once told me in Botswana:
“We have to go out there to see what we will find.”
Fuck it. I guess I’ll go.
A smorgasbord of themes I gathered from OG’s CFO summit:
1. The CFO as the Speed Governor
"The CFO is responsible for helping the CEO set the speed limit."
Growth needs guardrails. The CFO’s job isn’t to slam the brakes—it’s to ensure the company doesn’t outpace its ability to execute.
2. The CFO as Reality’s Referee
"The CFO needs the ability to navigate between the CEO’s optimistic reality distortion field and the laws of gravity."
Every great CEO bends reality. Every great CFO ensures it doesn’t snap.
3. Spreadsheets are Still Undefeated
"Let’s be real: Spreadsheets are the best piece of software humans have ever built."
No-code before no-code was a thing. Spreadsheets remain the ultimate tool for modeling, forecasting, and back-of-the-napkin genius.
4. Security Spending: A CFO’s Dilemma
"How do you justify a security budget as a CFO? Asking, because my current answer is 'you can have all the monies.'”
Security isn’t an ROI discussion—it’s an existential one. The best CFOs know when to challenge spend and when to just write the check. This budget remains tricky to nail down.
5. The CFO as a Fixer, Not Just a Watchdog
"Your job isn’t a pure control function—don’t come to the CEO and just tell them something is wrong. Go repair it."
The best CFOs don’t just report problems—they solve them. The finance team’s job is to optimize, not just audit.
6. The AI Whisperer’s Trick
"If you tell ChatGPT to 'take a deep breath and think through this step by step,' it actually gives you more accurate answers."
Even AI benefits from structured thinking. Turns out, the right prompt is half the battle. I tried this. It actually worked.
7. The Two Types of Churn
"People forget to record if their churn is product-related or relationship-related. Those are two fundamentally different problems in your business."
Not all churn is created equal. Product churn means you built the wrong thing. Relationship churn means you’re bad at selling it.
8. The Physics of Sales Hiring
"Are we abiding by the laws of physics as to how fast we can actually onboard and ramp a sales rep? Let’s be honest about that in our model."
Unrealistic ramp models are silent killers. Sales reps don’t hit quota just because finance said so.
9. When It’s Time for the CFO to Leave
"When does a CFO have to go? When they stop believing in the product. When they think the baby is ugly."
A CFO can manage a messy P&L, but they can’t fake conviction. If you don’t believe in what you’re selling, it’s time to move on.
10. The CFO as the Internal CEO
"The CEO is the external face of the company. The CFO is the internal CEO."
While the CEO sells the vision to investors and the market, the CFO ensures the company can actually deliver on it. Internally, the CFO is the one making sure the numbers match the narrative.
Shoutout to Casey Woo for pulling the event off. And check out OG if you are the special ops of what you do.
Run the Numbers
Apple | Spotify | YouTube
In this episode, I’m joined by Peter Benevides, CFO of publicly traded Olo, a leading vertical SaaS company powering digital ordering, payments, and guest engagement solutions for popular restaurant brands.
How Olo successfully expanded into payments
How the company stacks S-curves through continued product expansion and adoption
How this enables them to increase revenue without increasing the take-rate.
Pricing strategy and how Olo balances subscription and consumption-based models.
Quote I’ve Been Pondering
“If you owe the bank $100 that’s your problem. If you owe the bank $100 million, that’s the bank’s problem.”
-J. Paul Getty
One of the best things I learned leaning into an outward facing role.