Stop Building a Business That Steals Your Freedom - Jaime Rodriguez

CFO Chronicles: The Secrets Behind Success

CFO Chronicles: The Secrets Behind Success
Stop Building a Business That Steals Your Freedom - Jaime Rodriguez
Sep 18, 2025 Season 3 Episode 54
James Donovan

He scheduled his wedding around payroll. That’s when he knew something had to change.

Jaime Rodriguez, CEO of Bookkeepers.com, has helped over 17,000 students turn their skill into a scalable business. In this episode, he shares the real lessons that most freelancers and early-stage business owners miss:

• The two personality types that sabotage their own growth
 • The SOP mistake that stalled his own firm
 • Why most freelancers chase the wrong kind of “rich”
 • How to build a business that gives back your freedom

This one’s part gut check, part blueprint and it might just save you years of wheel-spinning.

🔗 Learn more at: bookkeepers.com

📲 Find Jaime on LinkedIn & Facebook (@jaime.at.bookkeepers)

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Episode Artwork Stop Building a Business That Steals Your Freedom - Jaime Rodriguez 31:12 Episode Artwork AI Isn’t the Future of Accounting, It’s Already Killing Off the Old Way - With Daniel Moshe 34:38 Episode Artwork Why Profit Isn’t Enough And What Most Founders Get Dead Wrong - With Daniel Dickeson 41:50 Episode Artwork The One CFO Skill That Can Save (or Kill) Your Business - With Jack Weinstein 37:09 Episode Artwork The Productivity Gap You Can’t See (Until It’s Too Late) - With Rhamy Alejeal 43:02 Episode Artwork The Mistake That Nearly Bankrupted Him (And Is Quietly Killing Most Businesses) - With Mike Milan 33:51 Episode Artwork He’s Interviewed Hundreds of Accounting Leaders - This Is What They All Miss 35:14 Episode Artwork He Spotted a $500K Payroll Leak. The Owner Had No Idea. 34:22 Episode Artwork Burnt Out, Understaffed, and Scaling Anyway? Sharrin Fuller Has a System for That 30:54 Episode Artwork Founders, You’re Leaking Profit, Here’s Where It’s Going - With Tom Schultz 26:36 Episode Artwork This Firm Ditched the Office and Doubled Team Retention - Rachel Phillips 25:19 Episode Artwork Your Next Client is Literally Searching for You, But You’re Invisible - With Jeremy Estey 28:41 Episode Artwork Your Firm Is Growing, But Not Scaling. Here’s Why - With Michael Straza 31:34 Episode Artwork 2,600 CFOs. 1 Global Community. What Jack McCullough Learned from Leading Them All 30:12 Episode Artwork From 4.5 Years in Prison to a 7-Figure Multi-State Firm - With Patience Jackson Rose 36:53 Episode Artwork Why 97% of Fractional CFOs Fail to Hit 7-Figures (Mark Gandy’s No-Nonsense Playbook) 29:04 Episode Artwork From Layoff to FBI Whistleblower: The Wild Path to Success - with Andrew Jordan 27:17 Episode Artwork How This CFO Landed 7 Clients with 30 Instagram Posts - with Jeremy Davila 28:53 Episode Artwork I Spoke on Stage, Signed 100 Books, and Still Felt Like an Imposter 15:22 Episode Artwork Spreadsheet Killer: How to Dominate Sales with Zero Experience 22:08 Episode Artwork From $0 to Baton Rouge’s #1 Accounting Firm in 3 Years - with John Roberts Jr. 34:07 Episode Artwork What Happens When a CFO Thinks Like a CEO - with Tom Dillon 30:24 Episode Artwork Why Cost Segregation Isn’t Just for Real Estate Investors — with Sean Graham 32:52 Episode Artwork What Most Accounting Firms Get Wrong About Serving Niche Clients — with Marta Grunberg 17:53 Episode Artwork Why Traditional Firms Are Falling Behind in a Virtual-First World — with Stoy Hall 26:20