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Jimmy Choos, Tax Write-Offs & the Real Cost of Starting a Business

Jimmy Choos, Tax Write-Offs & the Real Cost of Starting a Business

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Starting a business is exciting.

Then somebody starts talking about estimated taxes, retirement accounts, cash flow, business expenses, and whether the Jimmy Choos you bought for a speaking engagement are actually a tax write-off.

Apparently, they probably aren't. Rude. šŸ˜‚

In this episode, I’m joined by my friend Felicia Greenwald, founder of Aventurine Planning, Tax Strategist and Financial Planner, to talk about the financial side of entrepreneurship that doesn't get nearly enough attention.

If you're building a business while you're still employed, this conversation is especially important.

We talk about why keeping your corporate paycheck while you build can give you more freedom, not less. We dig into what you should be thinking about financially before you leave corporate, how to prepare for taxes once money starts coming in, and why entrepreneurship seems to cost more than you think it will.

We also talk about the people waiting to sell new entrepreneurs the next thing that's supposedly going to explode their revenue. Because apparently the minute you start a business, someone appears promising to help you make $10K, $100K or $1 million if you'll just hand over your credit card.

In this episode, we talk about:

  • Why I'm such a believer in building before you bounce
  • Creating financial runway before leaving your corporate paycheck
  • Figuring out how much income you actually need to replace
  • What to consider if you have stock options, RSUs or other corporate compensation
  • Why everything seems to cost more when you start a business
  • Red flags when someone promises massive revenue growth
  • Preparing for estimated taxes before they surprise the hell out of you
  • What a business deduction actually does, and what it doesn't
  • Why spending $100 to save $30 in taxes is still spending $70
  • Tracking your income and expenses before tax season
  • Why your business and financial decisions need to support the life you actually want

And yes, we answer the important question:

Can I buy a pair of Jimmy Choos, wear them on stage once, and call them a business expense?

Felicia is such a fun, practical voice on a topic that can feel intimidating, and this conversation is a great reminder that building a business isn't just about getting clients and making money.

It's also about making smart decisions with the money you make.

You don't have to blow up your life to build a bigger one.

Connect with Felicia

Felicia Greenwald is the founder of Aventurine Planning, where she helps business owners and professionals navigate the financial side of entrepreneurship and major career transitions.

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This conversation is for educational purposes only and isn't individualized financial or tax advice. Consult the appropriate financial or tax professional about your specific situation.