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

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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

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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

This week, we sit down with Brian Krug from Seguno and Brian Holmes of Burton Goods to unpack an honest story of restarting a business again from the ground up.

Why would anyone start over? Brian Holmes shares why he hit reset, and how he’s introducing Burton Goods to a fresh audience - starting with the email inbox. Both Brians dive deep into email strategy for new brands, what it really takes to build authenticity, and how to get more email opens with a better post-master score!

If you’re rebranding, relaunching, or simply wanting to get more engagement from your email marketing, this episode is packed with insights you don’t want to miss.

If you want to find out how visible your emails are, check out Seguno's visibility quiz here! https://www.seguno.com/check-inbox-placement

Burton Goods here: https://burtongoods.com/

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

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/

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
4:13 About Brian & Seguno
5:56 Migration from Magento into Shopify
9:07 Why Brian Started again
13:43 How To Introduce a New Brand to Potential Customers on Email
18:44 What Truly Makes A Brand Authentic?
21:07 Why Email Deliverability Matters
27:08 The Importance of a Postmaster Score
30:25 Finding What Works For You
35:08 Listening To What Customers Want
39:01 Burton Goods Content Strategy
43:04 How To Reach Out To Seguno

Support the show

This week we are joined by our brand new sponsors, Yoast!

Yoast has helped over 13 MILLION sites with their SEO. So, in this episode we discuss the ESSENTIAL SEO TIPS every Shopify store should be doing right now.

From the biggest “dos” and “donts” to shaping product pages, blog content, and overall site structure.

In 2025 SEO isn’t just about stuffing keywords. We explore the importance of intent-driven content, detail-rich pages, and creating meaningful experiences for both users and search engines.

Plus, with AI rapidly transforming how people discover and shop for products, we discuss how these shifts are reshaping search behaviour with the use of LLMs - And what that means for your SEO strategy moving forward!

Check out Yoast and get 15% off ALL monthly Shopify purchases for the first 6 months using code WWS15!

https://yoast.com/


Sign up to the Growth Hub here: https://wwspodcast.com/pages/the-growth-hub 

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  

Key Takeaways:
0:00 Introduction
1:36 About Carolyn at Yoast
3:29 About Alex at Yoast
5:39 The essential SEO tips for your e-commerce store
11:12 Product Schema
14:27 Topical Keywords: Green vs Olive
17:07 The Do's and Dont’s of category pages
20:08 Is AI Affecting Site Search?
23:22 How Yoast is helping Shopify Product Schemas
29:50 How to Leverage AI in your SEO
34:15 How LLMs are changing Google Search
41:06 Using Customer Service to inform Content Marketing

Support the show

In this episode, we sit down with James Hunt, the visionary founder behind SAA Clothing to uncover the heart, hustle, and high stakes of building a purpose-driven fashion brand.

In this episode we cover:
👕 What really sets SAA Clothing apart?
💡 How it all began - from one idea to a £50K opening weekend
🧠 Creating meaningful job opportunities for neurodivergent individuals
⚖️ Balancing passion with profit in a fast-moving industry
📚 The unfiltered truth about the challenges of writing a book
📱 Mastering the art of unique storytelling through social media
💰 Are you ready to scale with paid social? Here’s how
⚡ A round of quick fire questions to wrap it up!

This is more than a business story - it’s a masterclass in authenticity, resilience, and reimagining what fashion can be.

Check out SAA Clothing here: https://www.saaclothing.com/

Sign up to the Growth Hub here: https://wwspodcast.com/pages/the-growth-hub 

Check out our awesome sponsors!
Join the bootcamp and elevate your inventory game: https://info.brightpearl.com/winning-with-shopify-holiday-planning-bootcamp 

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

Key Takeaways:
0:00 Introduction
2:37 What’s different about SAA Clothing?
5:18 How SAA Started
8:04 Creating meaningful job opportunities for neurodivergent individuals
16:27 Launching with a £50K opening weekend!
20:06 Balancing purpose & profit
23:08 The challenges of writing a book
26:18 How To Tell a Unique Story Through Social Media
29:03 Are you ready for Paid Social?
30:22 Quick fire questions

Support the show

What do you get when you mix a talented artist, a single scrunchie, and a Christmas gift? You get Tina, the powerhouse founder behind XXL Scrunchie & Co, sharing her incredible story of building a standout brand in a crowded market - one giant scrunchie at a time!

In this exciting episode, Tina shares:

✨ How she started her business with just a scrunchie
📈 The strategies that helped XXL Scrunchie grow into a favourite brand
📹 Why YouTube is her secret weapon for brand growth - and how you can use it too
💌 Engaging your audience through email (spoiler: it’s way more fun than you think!)
🚀 How to plan ahead for successful product launches
📬 Is email still the future of business marketing?
⭐ How to actually leverage product reviews to boost your brand
🔮 A sneak peek at what’s next for the future of XXL Scrunchie

Whether you're an ecommerce newbie or looking to take your brand to the next level, this episode is packed with creative insights, real talk, and enough motivation to tie your hair back and get to work!

https://xxlandco.com/

Sign up to the Growth Hub here: https://wwspodcast.com/pages/the-growth-hub 

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 

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
1:45 How To Start A Business With Just A Scrunchy
10:53 How XXL Scrunchie Grew In A Busy Market
16:37 How To Grow Your Businesses Youtube Channel
20:25 How to Engage with Your Customers in Email
22:32 How To Plan Ahead for Product Launches
26:22 Is Email the Channel for the Future of Business?
28:14 How Do You Leverage Product Reviews?
33:43 The Future of XXL Scrunchie

Support the show

This week we talk all things global product sourcing!

Nick is joined by Anthony, the Founder of Cavela, a sourcing partner helping modern eCommerce brands navigate today’s supply chain challenges.

We break down the biggest issues facing Shopify brands, including rising tariffs, inconsistent supplier quality, and the hidden costs of poor diversification.

You’ll learn actionable strategies for matching product quality across different suppliers, diversifying your supply chain, and avoiding costly sourcing mistakes.

Whether you're scaling your brand or just getting started, this episode offers relevant timely insights that could save your business thousands!

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


Sign up to the Growth Hub here: https://wwspodcast.com/pages/the-growth-hub 

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  


Key Takeaways:
0:00 Introduction
2:27 Who Is Cavela?
4:52 The Biggest Challenges With Sourcing Stock Today
7:59 How To Diversify Your Supply Chain
11:23 How To Match Quality Across Suppliers
18:18 What Should US Brands Do About Tariffs?
26:14 Mistakes Shopify Brands Should Be Avoiding
32:48 Cavela's Sourcing Process

Support the show

This week, we're mixing things up!

Nick has just become a brand new dad and whilst he’s adjusting to dad life, we’ve collated some of the most impactful moments from the past 6 months.

Chapters:
0:00 Introduction
0:52 Simple Tweaks To 2X Your Shopify Sales Fast!
7:48 Increase Your Revenue 108%
14:13 Influencer Gifting - The Low Cost Strategy
20:54 Blueprint to Ecom Growth in 2025
23:10 Gaining 500,000 Followers Without Ads!

We hope you enjoy!

Sign up to the Growth Hub here: https://wwspodcast.com/pages/the-growth-hub 

Check out our awesome sponsors!
Join the bootcamp and elevate your inventory game: https://info.brightpearl.com/winning-with-shopify-holiday-planning-bootcamp 

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

Support the show

In this episode, Nick breaks down exactly how to improve your conversion rate in practical, actionable ways.

We uncover five powerful conversion rate tips that can make an immediate impact on your results!

Plus, Nick has a CRO challenge designed to push your strategy further and help you implement what you’ve learned right away.

Let’s get optimising!

Want to work with Nick? Get in touch here - https://spec.digital/contact

Sign up to the Growth Hub here: https://wwspodcast.com/pages/the-growth-hub 

Check out our awesome sponsors!
Join the bootcamp and elevate your inventory game: https://info.brightpearl.com/winning-with-shopify-holiday-planning-bootcamp 

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

Key Takeaways:
0:00 Introduction & The Growth Hub
3:48 How To Improve Your Conversion Rate
5:23 Conversion Rate Tip #1 
9:07 Conversion Rate Tip #2
12:46 Conversion Rate Tip #3
17:15 Conversion Rate Tip #4
19:35 A Challenge That Will Rocket Your CRO
21:32 Conversion Rate Tip #5

Support the show