153 Tax Architecture: Build Your Business Around IRS Rules, Not Despite Them with Mike Jesowshek CPA

When was the last time you made a business decision before asking what it costs in taxes?Most founders design their operations first, then call their accountant in March to calculate the damage. They hire in July, buy equipment in November, distribute profits in December, and never consider tax implications until the bill lands. Mike Jesowshek spent a decade watching entrepreneurs bleed five figures annually, not from missing deductions but from building their businesses backwards. According to the National Society of Accountants, small businesses overpay by $11,400 per year on average due to missed planning opportunities.In this episode, Mike breaks down the difference between tax preparation (compliance paperwork) and tax planning (proactive strategy that actually saves money). You'll learn why your entity structure matters more than you think, how to shift everyday spending from after-tax to pre-tax dollars, and which strategies work at $100K versus $1M in revenue. If you've ever felt like taxes are something that happen to you rather than something you control, this conversation will change how you build.Keywords: tax strategy, tax planning, S-corporation, LLC structure, small business taxes, tax deductions, entity structure, CPA advice, business tax savings, self-employment tax