Paden Squires: The CPA Teaching Entrepreneurs How to Stop Flying Blind With Their Finances

Most entrepreneurs are building impressive businesses on a completely broken financial foundation.

In this episode of Hacks and Hobbies, Junaid sits down with Paden Squires, a CPA, CFP, and founder of Squires Tax Planning, who walked away from the corporate world to help business owners finally feel in control of their money. Paden reveals why even multi–million-dollar businesses are often a financial mess behind the scenes, why “just hiring a CPA” isn’t enough, and how simple systems, the right tools, and proactive tax planning can completely change the trajectory of your business and your life.

This conversation is a roadmap for solopreneurs and small business owners who are tired of dreading tax season, guessing from their bank balance, and hoping it will all “work out somehow.” Paden breaks down how to think about profit, how to pay yourself, what numbers actually matter, and how to use AI and systems to build a business that doesn’t depend on you grinding 70 hours a week.

You’ll walk away seeing finances not as fear, but as a framework for freedom.

5 Key Takeaways

• Most entrepreneurs are flying blind financially – even multi–million-dollar businesses often have chaotic books and zero decision-making insight.
• You can’t outsource responsibility for your numbers – you don’t need to be a CPA, but you must understand your own financial statements.
• Tax planning is an opportunity, not a bill – proactive, year-round strategy can legally save tens of thousands, far beyond basic tax prep.
• Systems and tech are the real leverage – AI tools, CRMs, and structured processes turn overwhelm into clarity and scalable growth.
• Solopreneurs must stop “running the business by the bank account” – intentional profit targets (like Profit First) and simple tracking change everything.

Timestamps

• [00:00] The fear of finances and why entrepreneurs secretly dread their numbers
• [01:36] Leaving corporate: why Paden burned the bridge and started from his living room
• [02:38] The shocking truth: inside the messy finances of multi–million-dollar businesses
• [04:54] The biggest money misconception: “I’ll just hire someone to handle it”
• [08:18] Tax prep vs tax planning: how most business owners are leaving money on the table
• [11:54] Inside Paden’s clarity sessions: finding $20K–$30K in tax savings in a single review
• [15:02] Systems, CRMs and AI: building a business that doesn’t rely on you
• [20:26] Profit First, paying yourself, and why the bank balance is lying to you

Guest Links – Paden Squires

(Add or update once available for this episode’s show notes.)

Website: https://www.squirestaxplanning.com
Personal Site: https://www.padensquires.com
Instagram: https://www.instagram.com/padensquires
Facebook: https://www.facebook.com/profile.php?id=100089855132002
LinkedIn: https://www.linkedin.com/in/paden-squires-cpa-cfp-19681a1a
YouTube: https://www.youtube.com/@PadenSquires
Apple Podcasts: https://podcasts.apple.com/us/podcast/behind-their-success-advice-for-entrepreneurs/id1723352366
Spotify Podcast: https://open.spotify.com/show/2sXtqL6QHmDykXRJRFX71W?si=1760bcbc08dc4130&nd=1&dlsi=a1622ac901c2497a

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