1. What’s the quick origin story of your brand, and what makes your product or positioning genuinely different from other options in your niche?

Brandi Russell: Comfy Cup was born when our 8‑year‑old baseball‑playing son got so tired of fidgeting with the hard, bulky cup his coach required that we challenged him to help create a better way to protect the family jewels without driving kids crazy. Kyler and I went to the store for foam and fabric and turned our dining room into a little sports‑safety lab, hand‑sewing the very first Comfy Cup prototype; a soft, lightweight, and flexible, yet still protective enough for youth sports. That homemade solution has grown into a kid‑approved cup designed specifically for young athletes’ bodies, using flexible impact‑absorbing foam and moisture‑wicking fabric so kids can stay focused on the game instead of the gear. What truly makes our product and positioning different is that Comfy Cup isn’t just a shrunken‑down adult cup; it’s purpose‑built for kids, invented by a kid, and backed by a family mission to make sports safer and more enjoyable for young athletes, one less distraction at a time.

2. Since launch, what have been the 1–2 real turning points for your brand-specific decisions, pivots, or experiments that noticeably changed your growth or profitability-and what did you learn from them?

Brandi Russell: One big turning point was deciding to move beyond our “craft‑project” phase into real manufacturing, investing in tooling, inventory, and partnerships so Comfy Cup could be available through our own site and online retailers instead of just our basement and local circles. That shift took us from a little family hustle to a consistent business, and it taught us that if you truly want to protect more kids on more fields, you have to treat it like a real company, carrying liability insurance (because we’re literally protecting the family jewels) and building systems that can handle growth.

The second major turning point was transitioning from a drop-ship relationship with Amazon to Fulfillment by Amazon (FBA), which meant handing off the picking, packing, and shipping to Amazon’s network instead of doing every single order from our home. Moving to FBA boosted our visibility, sped up delivery for parents, and freed up our family’s time and energy to focus on what we do best.

3. Which 2-3 channels drive most of your revenue right now (for example SEO, paid social, email, marketplaces, influencers), and what have you learned about making those channels work in your category?

Brandi Russell: For Comfy Cup, the three channels that really move the needle right now are SEO, social media, and good old‑fashioned word of mouth, and each one works a little differently when you’re in the business of protecting young athletes’ groins.
​
SEO has been huge because parents usually start with a search like “youth athletic cup” or “comfortable cup for boys” when their kid is suddenly required to wear one, so having clear, keyword‑rich product pages and educational content helps us show up right when that “uh‑oh, we need a cup” moment hits. The big lesson here is that in this category, answering anxious parent questions (comfort, safety, sizing, age range) in plain language on your site is just as important as selling the product itself.
​
Social media gives our brand a face and a heartbeat. Parents see a real kid inventor, behind‑the‑scenes hustle, and authentic testimonials; not just another piece of plastic gear. What we’ve learned is that authentic stories, testimonials, and a little humor about “protecting the family jewels” outperform polished, salesy content every time, because parents want to trust who’s guarding their child’s groin.

Word of mouth might be the most powerful of all: once a few boys on a team discover they can wear a cup without constant fidgeting, other parents and coaches quickly take notice. In a tight‑knit world of leagues, teams, and group chats, delivering a product that actually solves the comfort problem turns every satisfied family into a mini spokesperson, teaching us that the best “campaign” is still a kid who forgets he’s even wearing his cup.

4. How are you thinking about search in 2025 – Google, AI assistants like ChatGPT, and other discovery platforms? What, if anything, have you changed in your content or site to stay visible as AI search grows?

Brandi Russell: The way parents search has definitely shifted from “Google it” to “ask AI,” and the good news for us is that almost ten years of authentic Comfy Cup content is actually working in our favor. Between our long‑standing website story, detailed product pages, and years of interviews and features that share our real mom‑and‑kid‑inventor journey, there is already a big, trustworthy content footprint for AI tools to pull from when parents ask about youth athletic cups or more comfortable protection for young athletes.
​
Because of that, instead of scrambling to “hack” AI search, we’ve focused on doubling down on what’s already working: keeping our site clear, human, and helpful for parents, and saying yes to more conversations on podcasts and other platforms where we can talk candidly about kids, comfort, and groin protection. The main change we’ve made is being more intentional about consistency. We make sure our story, mission, and product details line up everywhere online, so whether a parent finds us through Google, Amazon, or ChatGPT, they see the same trusted, long‑standing brand that’s been protecting young athletes’ family jewels for nearly a decade.

5. What do you do to turn first‑time buyers into repeat customers and advocates? Are there specific experiences, content, or community touches that work especially well for you?

Brandi Russell: In a category like youth athletic cups, most families only buy once, unless they have a bench full of boys at home. So, the goal is less about repeat purchases and more about turning that first happy experience into a ripple effect of referrals. That means every Comfy Cup we ship has to perform so well that parents feel confident recommending us to other families on the team, in their league, and in their group chats, because they know we’re genuinely here to protect kids’ groins, not just sell gear.

Instead of building loyalty or subscription programs, we focus on simple, human touches that fuel word of mouth: a product that actually solves the comfort problem, clear and honest communication, and a family‑driven story that makes it easy for parents to say, “You should try this one; it was invented by a kid and his mom, and my son finally stopped fidgeting.” In other words, our best “retention” strategy is making that first‑time buyer feel so relieved and satisfied that recommending Comfy Cup to the next sports parent feels like part of being a good teammate in the game of keeping kids safe.

6. If you had to write a short playbook for an ecommerce founder one stage behind you, what would you double down on over the next 12 months – and what would you stop doing entirely?

Brandi Russell: For a founder one stage behind us, my advice would be to double down on testimonials and smart distribution, and cut anything that doesn’t directly help you sell more units or serve customers better.

Over the next 12 months, I would double down on gathering testimonials. Reviews and testimonials are your trust engine; they turn a nervous first‑time buyer into someone willing to put your product in charge of their child’s groin.

Second, I would immediately get my product on Amazon with Fulfillment by Amazon (FBA) if you aren’t there already. Let Amazon handle the pick‑pack‑ship logistics so you can focus on product quality, content, and customer connection; faster shipping and Prime eligibility can dramatically boost conversion and make your brand discoverable to parents who start their search on Amazon instead of Google.
​
I’d stop spreading myself thin and stop tinkering with endless micro‑edits to branding while ignoring reviews, listings, and operations. In other words, spend less time looking “entrepreneurial” and more time building testimonials, FBA, solid listings.