Hacks & Hobbies

Most entrepreneurs are not failing because of their product… they’re failing because of their numbers. In this episode of Hacks and Hobbies, Junaid sits down with Paden Squires, founder of Squires Tax Planning, who has quietly helped business owners save tens of thousands of dollars and rebuild their relationship with money. This isn’t a “tax tips” episode. It’s a deep dive into identity, behavior change, and the simple financial habits that separate stuck founders from those who compound wealth year after year. Paden shares how Ray Dalio’s “Principles”, radical transparency, and his own philosophy of integrity and alignment shape the way he coaches entrepreneurs. From saving a client $30,000+ in taxes with a few structural moves, to spotting patterns in thousands of tax returns, Peyton reveals how the real unlock isn’t a secret loophole—it’s the willingness to face your numbers, do the work, and change who you are as a business owner. If your finances feel overwhelming, confusing, or “not your thing,” thi