The Tax Side of Building Wealth: RSUs, IPOs, and Who's Actually in Your Corner

Did you know that in the United States, anyone can sign your tax return — no license required? Katrina Kowalski found that out the hard way when her husband got hit with a $50,000-plus IRS audit, courtesy of an unlicensed preparer who was a family friend. That moment set her on a path from mortgage industry burnout, to quitting a Big 5 accounting firm on the day after Christmas, to eventually building On Point Wealth and On Point Tax Services in Portsmouth, New Hampshire. In this conversation, Katrina joins Wheeler and Colin to talk about what business owners get wrong about taxes, why the goal shouldn't just be paying as little as possible, and how the right CPA relationship looks less like damage control and more like a long-term financial partnership. She walks through the hidden complexity of RSUs and IPO stock — including the client who watched their stock fall 65% and still got the tax bill — and why your CPA and your financial advisor need to be in the same conversation, not separate silos. The episode goes deeper than tactics: Katrina talks about launching her firm in August 2019, six months before COVID, building a partnership with her now-co-owner Emily Roster, and why she believes the CPA talent shortage is a direct result of an industry that still rewards volume over relationship. And with $34 trillion of wealth transferring across generations, she makes the case that women need to be at the financial table — not just inheriting a box of paperwork they've never seen before. Katrina's guiding philosophy: do the best you can until you know better, then when you know better, do better. 0:00 Intro — Katrina's origin story: husband's IRS audit and the unlicensed tax preparer 4:30 Arthur Andersen, Enron, and quitting her Big 5 job the day after Christmas 9:00 Why you don't need a license to sign a tax return in America 13:30 What an IRS audit actually looks like — and what it cost Katrina's husband 18:00 "Pigs get fat, hogs get slaughtered" — the right way to think about tax strategy 23:00 Launching OnPoint in 2019, COVID, and building alongside co-owner Emily Roster 30:00 The CPA shortage and why women are leaving the profession 36:30 Self-employment taxes, quarterly estimates, and the #1 mistake new business owners make 42:00 RSUs, IPOs, and the clients who owed taxes on stock that had already tanked 49:00 The $34 trillion wealth transfer and why women need to be in the room 56:00 Why your CPA and financial advisor should never be in silos 1:01:00 Closing: summer reading, Goodreads, and Katrina's philosophy on growth Follow Us: Instagram:   / compoundgrowthpod   TikTok:   / compoundgrowthpod   Wheeler’s LinkedIn:   / wheeler-crowley-0a63933b   Colin’s LinkedIn:   / colin-walker-mba-6099a038   Credits: Created By: Wheeler Crowley and Colin Walker Production Assistance: Tori Rothwell