Point Of The Story Your Blazer Isn't a Business Expense: Baby Steps To Better Bookkeeping with Madison Dearly
Jul 31, 2025
Madison Dearly, a bookkeeper and S-Corp specialist (and former Miss New Mexico), walks through bookkeeping basics with humor. She covers what counts as a real business expense, why S-Corps are trickier than they seem, and quick baby steps to tidy books. Expect stories, tax reality checks, and practical tips to make finances less scary.
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How A Choking Moment Turned Into A Client Relationship
- Madison and Sarah met at Spark Conference when Sarah started choking and Madison offered to perform the Heimlich, which sparked their relationship and led to Madison filling out Sarah's inquiry form.
- The anecdote highlights Madison's quick response and professionalism that turned a crisis into a trusted client relationship and ongoing referral admiration.
S Corp Means New Tax Return And Payroll
- Electing S‑Corp status adds complexity: a separate tax return, payroll obligations, and more nuanced bookkeeping that many people underestimate.
- Madison warns that S‑Corp benefits require sustainable revenue and administrative capacity or you'll face IRS issues and higher CPA fees.
Wait For Steady Profits Before Electing S Corp
- Only consider S‑Corp election after consistent profits for multiple years; Madison recommends at least two to three years of stable profit before switching.
- She uses $50,000 profit as a rough threshold because it supports a reasonable salary and sustains payroll obligations.