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Charts Everything, Even Love With Nick Jain | Ship's Log 18

Project Candor: Ordinary People. Unexpected Stories

Chapters
0:00
Instincts Won't Save You in the 21st Century
0:15
Intro
1:15
Nick Jain joins the conversation
2:19
First Encounter with Failure
4:18
Equations vs. Instincts
6:08
The Economics of Happiness
7:20
Reading a Company: First Signals
8:43
What Happens When the Boss Won't Listen to Data
11:18
The Hardest Call on Wall Street
13:27
What Professional Poker Actually Feels Like
14:47
The Math Game of Professional Poker
19:23
Knowing What You Want at Age 6
21:44
Two Truths & A Lie
31:42
Battle Rap and Wordplay
33:43
Eagle Rock CFO: Fortune 500 Analysis for $20M Companies
36:24
How to Connect with Nick
37:06
Words of Wisdom
Project Candor: Ordinary People. Unexpected Stories
Charts Everything, Even Love With Nick Jain | Ship's Log 18
Apr 30, 2026 Season 1 Episode 18
Jeanne Andersen

Guest Quote

"Instinctual thinking is great when you're on a savanna running from a lion. It's not so great in the 21st century."

— Nick Jain 

Episode Summary

Nick Jain came to this conversation carrying credentials that would make most people nervous — Harvard MBA, top of his class, a decade in private equity, three company turnarounds including one he scaled past $100 million. But what comes through immediately is that the math never stays abstract with Nick. It shows up everywhere: in how he proposed to his wife, in how he chooses which poker hands to play, in how he sized up an investment against a senior colleague's instincts and held his ground.

The conversation moves through Nick's early encounter with academic failure in college, his two-part framework for making decisions under pressure, the HIPPO principle that quietly kills companies, and a genuinely fascinating breakdown of why elite poker is mostly about patience and folding — not bluffing. He's quick, clear, and unexpectedly funny, and the Battle Rap detour near the end of the episode is one of the show's better 'wait, what?' moments.

The episode closes with Nick sharing what Eagle Rock CFO Services is doing — delivering Fortune 500-grade financial analysis to businesses in the $5–50M range at a price point that actually makes sense. Six weeks old at recording. Already has customers. Worth watching.

Guest Bio

Nick Jain is the co-founder of Eagle Rock CFO Services, where he helps small businesses get elite financial guidance without the Fortune 500 price tag. He trained as a mathematician and physicist, earned his MBA from Harvard Business School — graduating top of his class — and spent a decade in private equity before leading turnarounds as CFO and CEO across trucking, software, and eCommerce. He now works with companies in the $5–50M range, bringing the same playbooks that drive large corporations down to a scale that growing businesses can actually use.

Guest Links

Website:  http://eaglerockcfo.com/
LinkedIn:  https://www.linkedin.com/in/nickmjain/
YouTube:  https://www.youtube.com/@EagleRockCFOServices
Eagle Rock Podcast:  https://www.eaglerockcfo.com/podcast

Guest CTA

Listeners can book a free 30-minute strategy call where Nick reviews their financials and provides 2-3 actionable recommendations to improve profitability or cash flow — no strings attached.

Book your free call: https://www.eaglerockcfo.com/podcast

Who do you know who'd make a great guest for the show? Please let us know.
Email: info@projectcandor.com

Website:   https://www.projectcandor.com

Social Media

Facebook:  https://www.facebook.com/ProjectCandor/
LinkedIn:     https://www.linkedin.com/company/projectcandor/
Instagram:  https://www.instagram.com/project.candor/
YouTube:    https://www.youtube.com/@ProjectCandorPodcast