Are you a Shopify store owner feeling overwhelmed by sales tax rules?

In this must-listen episode, we sit down with Ryan Pinkham, VP of Go-to-Market at TaxCloud, to unpack the most critical sales tax issues eCommerce entrepreneurs face.

We'll dive into:

✅ Whether Shopify calculates your tax return — and what it doesn't do
✅ Why marketplaces like Amazon and Etsy change the tax game
✅ How to stay compliant as you scale your business across state lines
✅ The overlooked problem of managing your Shopify tax bill
✅ And how the complex patchwork of U.S. sales tax laws can trip up even seasoned sellers

Whether you're just launching your first store or expanding to new markets, this episode is packed with actionable insights to help you stay compliant and stress-free.


Get free migration onboarding services for TaxCloud (including 3 calls, email support, and hands-on guidance!) - https://taxcloud.com/winning/

Check out our awesome sponsors!
If you use Shopify and Canva, this app will save you time! https://www.seguno.com/canva-shopify-connect

Join the bootcamp and elevate your inventory game: https://info.brightpearl.com/winning-with-shopify-holiday-planning-bootcamp

Check out Yoast and get 15% off ALL monthly Shopify purchases for the first 6 months using code WWS15! https://yoast.com/winningwithshopify-exclusive/

To get 50% off a product sample order & fast-track the waiting list, use code WINNING and this link: https://www.cavela.com/signup?affiliate=WINNING


Key Takeaways:
0:00 Introduction
1:52 About Taxcloud
3:48 What's the first thing Shopify Store owners should know about Sales Tax
7:41 Do You Need to Calculate Your Tax Return on Shopify?
15:32 Sales Tax on e-books and other virtual goods
19:48 Marketplaces and taxation
26:38 The Problems with Scaling a Business
28:16 The US sales tax problems
35:09 How to manage your tax bill on Shopify

Support the show

In this episode, we dive into the story of Nahar Geva, founder of Zik Analytics, and how his journey shaped a powerful tool in e-commerce today!

Nahar shares how sourcing products & dropshipping has changed, and where the opportunities are right now. Why a strong USP is key to standing out, and how AI can streamline your business operations. We also touch on how dropshippers can create a solid brand experience, better understand their audience, and prepare for the future of AI in e-commerce.

Check out Zik Analytics here and use code ‘WinningWithShopify’ to get 70% off monthly plans and 50% off annual plans! https://www.zikanalytics.com/r/wws


Check out our awesome sponsors!
To get 50% off a product sample order & fast-track the waiting list, use code WINNING and this link: https://www.cavela.com/signup?affiliate=WINNING

If you use Shopify and Canva, this app will save you time! https://www.seguno.com/canva-shopify-connect

Join the bootcamp and elevate your inventory game: https://info.brightpearl.com/winning-with-shopify-holiday-planning-bootcamp

Check out Yoast and get 15% off ALL monthly Shopify purchases for the first 6 months using code WWS15! https://yoast.com/winningwithshopify-exclusive/

Get free migration onboarding services for TaxCloud (including 3 calls, email support, and hands-on guidance!) - https://taxcloud.com/winning/


Key Takeaways:
0:00 Introduction & About Nahar
1:32 How Zik Analytics Integrates with E-Commerce
5:18 What To Do With Data driven product research
6:51 The Importance of USPs in e-commerce
10:37 How to Use AI in your business
14:24 Drop Shipping and Brand Experience
18:08 Ways Dropshippers Can Understand Their Audience
26:04 The Future of AI for Dropshipping

Support the show

In this episode, we sit down with Paul Arellanes, the CTO at Rebel Cheese, to explore how a seasoned tech leader with roots in IBM, NXP, and Amazon found his calling in the plant-based food world.

We cover:
- Why Rebel Cheese's Shark Tank moment was just the beginning.
- Paul's philosophy on building & scaling a DTC tech stack on Shopify, while keeping costs in check and customer experience front and centre.
- Lessons learned from early technical decisions, including those sneaky shipping costs.
- His approach to app selection (hint: not everything in the Shopify App Store is gold)!
- How AI is reshaping daily operations, and what tools he's excited about right now.

Whether you’re a DTC founder, a tech leader in ecommerce, or just a fan of cheese that doesn’t come from cows, this episode is full of insights you won’t want to miss 🧀💻

Connect with Paul here: https://www.linkedin.com/in/paularellanes
Check out Rebel Cheese here: https://rebelcheese.com

Check out our awesome sponsors!
Get free migration onboarding services for TaxCloud (including 3 calls, email support, and hands-on guidance!) - https://taxcloud.com/winning

To get 50% off a product sample order & fast-track the waiting list, use code WINNING and this link: https://www.cavela.com/signup?affiliate=WINNING

If you use Shopify and Canva, this app will save you time! https://www.seguno.com/canva-shopify-connect

Join the bootcamp and elevate your inventory game: https://info.brightpearl.com/winning-with-shopify-holiday-planning-bootcamp

Check out Yoast and get 15% off ALL monthly Shopify purchases for the first 6 months using code WWS15! https://yoast.com/winningwithshopify-exclusive

Support the show