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?

Brandon Fields: Old Bones Therapy was born on a skateboard. I have been skating for almost 40 years, including some 12-foot drops onto concrete that my body still files complaints about. Add two decades at a desk writing software and my lower back, knees, and joints were a mess by my mid-40s. One night I was trying to ice my back while cooking dinner, and the ice pack kept slipping, melting, and missing the spot. So I engineered something that stayed put. That kitchen-table fix became the company.

What makes us different is that we treat compression as apparel, not as a medical device that happens to be wearable. Knitted construction instead of bulky neoprene, slim enough to wear under jeans, with color options because people care how their gear looks. We are medical-grade where it counts and human everywhere else. Every order ships with free stickers, which is the skater kid smuggled into a medical brand. We are not built for people who want to rest. We are built for people who refuse to slow down.

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?

Brandon Fields: The biggest one was deciding to stay bootstrapped. No venture capital, no parent company, no outside money, ever. That forced every dollar to earn its place and kept us honest about profitability instead of chasing growth we could not afford.

The second turning point was a brutal audit of our software stack. Ecommerce founders accumulate SaaS subscriptions like barnacles. In early 2026 I started cutting hard. We cancelled our third-party attribution platform and rebuilt that capability ourselves. We cancelled an SEO retainer and an affiliate platform that were not paying for themselves. The lesson was that most tools sell you a dashboard, not an outcome, and if you are willing to do the work you can often build the outcome cheaper and own it outright.

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?

Brandon Fields: Our core is paid social on Meta, Google Ads, and email through Klaviyo, supported by organic search and our own content. Email is the quiet workhorse. Welcome, abandoned cart, and winback flows do a lot of the heavy lifting and cost almost nothing to run once they are built.

The biggest lesson in our category is that compression is a trust purchase. People are buying something they will wear on a sore knee all day, so proof beats persuasion. Real customer reviews, photos, and education about how and when to wear the product move the needle far more than another clever ad. We lean on that proof everywhere instead of leaning on discounts.

We are also deliberately narrow. No Amazon, no marketplaces, no affiliate program. We would rather own the customer relationship end to end than rent shelf space or pay a percentage to a middle layer. For a bootstrapped brand, owning the relationship is the whole game, because it is the only asset that compounds.

4. How are you thinking about search in 2026 – 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?

Brandon Fields: This is the part I am most obsessed with right now. Search is splitting into two jobs. There is still classic Google, but a growing share of buying questions now get answered by ChatGPT, AI assistants, and AI overviews that never send a click. The old game was ranking a page. The new game is making sure the brand is legible to machines.

So we have shifted from chasing keywords toward clear structured data, plain-language answers to the real questions customers ask, and content an AI can quote accurately rather than guess at. We treat it as its own discipline inside the business, with a dedicated function in our AI system aimed squarely at AI discovery and agentic commerce. The mental model is simple. If an assistant is going to recommend a compression sleeve to someone, I want it holding the right facts about ours.

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?

Brandon Fields: Our retention engine is email, full stop. No SMS, just a well-built Klaviyo program that treats people like humans instead of wallets.

The deeper play is identity. Our customers are not really buying a knee sleeve. They are buying permission to keep doing the thing they love. So we put stickers in every box, we use a brand voice that validates instead of sells, and we mean the tagline we put on everything: Ruling at Life. When the brand stands for refusing to quit, repeat purchase takes care of itself, because the relationship was never transactional in the first place.

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?

Brandon Fields: Double down on two things. First, the unsexy math. Know your contribution margin per order, not just your revenue, because revenue with no margin is just expensive applause. Second, own your data and your customer relationship. The founders who win the next twelve months are the ones building capability in-house instead of renting it, especially as AI makes it cheaper than ever to do that.

Stop two things entirely. Stop paying for SaaS that sells you a dashboard instead of an outcome. Audit every subscription twice a year and cancel anything that cannot justify its cost in plain language. And stop chasing channels you do not own, like marketplaces and affiliate schemes, that pay a middle layer to stand between you and your customer. And one more for free: stay bootstrapped longer than feels comfortable. Constraints are a feature, not a curse.