One of the biggest mistakes I see new entrepreneurs make is that they start building their businesses in financial quicksand. I’m joined by fractional CFO and tax strategist Shannon Weinstein to break down how to set yourself up for success from day one. 

I ask Shannon about everything from writing off phone bills and meals to how to find the right tax professional. We also talk about how she decided to go all-in on her brand, Keep What You Earn, and what inspired her brilliant approach to marketing. Don’t save this episode for Aprilーthe key to being tax savvy is proactivity and preparation. 

Episode Timeline & Discussion Questions:

(1:07) Welcome back to The Chris Harder Show. Today, Chris is joined by Shannon Weinstein.

(4:35) Chris asks Shannon, “You walked away from your corporate gig, which paid you multiple six figures, and you’ve made the transition that everybody hopes to make. So start there. Tell me about this transition. Was it scary? Was it hard? How’d you do it?”

(5:44) Chris asks Shannon, “What milestone did you have to hit to know that you were secure walking away from that corporate job?”

(7:56) Chris asks Shannon, “You’re also taking care of your husband and helping him out physically a little bit. Do you mind sharing some of that background?”

(9:48) Chris asks Shannon, “Talk to me about how you reconcile this type of risk-averse personality with the risk that it requires to get into entrepreneurship.”

(11:25) Chris asks Shannon, “Could you explain the difference between just being an accountant and being a fractional CFO and a tax strategist?” 

(15:24) Chris asks Shannon, “When should somebody seek out a tax strategist?”

(17:06) Chris asks Shannon, “How can somebody know if their tax strategist or accounting team is throwing up some red flags that they should be a little bit concerned about?”

(20:16) Chris asks Shannon, “What are some more questions that somebody can ask their tax professional to know if they’re truly working with the right person or not?”

(22:29) Chris asks Shannon, “Would you share maybe two or three of the traps that people think they can do but they should be a little bit cautious around?”

(24:35) Chris asks Shannon, “Let’s say somebody buys a few outfits, and they do an all day photo shoot. Is that deductible?”

(26:17) Chris asks Shannon, “Now share one or two really fun deductions that people don’t think about, or that they typically miss, even if they have just a side hustle.”

(27:35) Chris asks Shannon, “I’m gonna give you some rapid fire yes or no questions. Can you write off your cell phone bill if you have a business?”

(28:31) Chris asks Shannon, “Do you have to save receipts?”

(31:18) Chris asks Shannon, “Do you have a good easy system of taking a picture and storing it somewhere?”

(32:06) Chris asks Shannon, “We deduct a lot of DoorDash and Uber Eats. Is that deductible or not deductible?”

(34:16) Chris asks Shannon, “What about writing off the majority of your travel and making up a business reason for it?”

(35:18) Chris asks Shannon, “If both you and your partner are both officers in the company, can you write off retreats?”

(36:07) Chris asks Shannon, “Can you explain that Augusta rule a little bit more?”

(38:01) Chris asks Shannon, “How do you determine how much you should rent your house for?” 

(39:40) Chris asks Shannon, “Why did you start a podcast and commit so heavily to it?”

(45:19) Chris asks Shannon, “Where can individuals turn to at least get the basic knowledge?”

(47:10) Chris asks Shannon, “What are some of the tools, templates and resources in there?”

(50:27) Chris asks Shannon, “Use Code CHRIS for $50 off Business Financial Quickstarter: keepwhatyouearn.com/chris” 

(53:51) Chris asks listeners to share the podcast and leave a 5-star review.