A thought exercise for entrepreneurs

One of the most valuable resources I’ve used over the last nine months isn’t a book, a video, or a mentor. It’s the Y Combinator application. I talk to a few people every month about entrepreneurship (not that I’m an expert, but I love talking about it), and I always recommend they fill out the YC application every three months and submit it. I’ve skipped one myself, but the exercise alone is worth it. So, I'll walk you through the two questions I think are most important and answer them from my own experience. Hopefully, by the end, if you're building something, you'll try the exercise yourself. The key is honesty: if you're not truthful, you'll only waste your own time. Question 1: “Why did you pick this idea to work on? Do you have domain expertise in this area? How do you know people need what you're making?” The truth is, I didn't really pick this idea, I stumbled into it by failing twice. I launched one product, it didn't work. Launched another, same story. But in that second attempt, there was one small piece that stuck: people kept showing interest in gear. That tiny spark of traction made me stop and dig deeper. Now, I'm no expert in guided experiences or even gear, technically. But after hundreds of conversations with guides and outdoor professionals, I'm probably in the top 1% of people who understand how the system works: from certifications to payments, from influencer culture to authenticity, to what makes someone a truly trusted outdoorsperson. I didn't start with expertise, I built it through conversation, observation, and relentless curiosity (with a lot of help from ChatGPT deep research). How do I know people need what I'm building? The short answer: they don't need it, they want it. We recently partnered with the American Mountain Guides Association, and within 24 hours, one email turned into 30 meetings scheduled with outdoor professionals ranging from certified guides to first-year instructors. They've all signed up so far, and a few didn't even know they could make money. Question 2: “Why doesn’t this idea already exist?” The answer? It does, sort of. ShopMy, founded in 2021, is building a successful business on the same foundation: affiliate commissions, storefronts, and simple tools to organize and share products. But their world is fashion and lifestyle influencers. So why hasn’t it worked in the outdoor world? Because trust operates differently here. Affiliate links can feel kitschy or inauthentic, which is fine if you're selling handbags. But in the mountains or on a river, the gear you use can mean warm or cold, safe or unsafe, success or failure. Some companies have experimented with outdoor recommendations, but no one has truly built a platform where athletes and professionals treat it as a trusted extension of their reputation. That's why Rendezvu makes sense. ShopMy works brilliantly for fashion, but the needs of a backcountry ski guide, a trail-running coach, or a fly-fishing outfitter are entirely different. These aren't people recommending skincare products, they're recommending avalanche beacons, hydration vests, and fly rods. Their credibility comes from years in the field, not follower counts. As Alexis Ohanian once said about Reddit, "It's like a party: when you walk in, you know the vibe." The same goes for Rendezvu versus ShopMy. The culture is completely different. Outdoor athletes and professionals have always influenced what people buy. Ask anyone who's purchased skis, running shoes, or a harness because a guide, coach, or training partner swore by it. The trust is already there. The recommendations are already happening. What's missing is the infrastructure, and a brand that respects and amplifies that trust. YC's questions reminded me that the best founders don't just chase ideas, they chase truth. The truth is that trust has always driven how people buy gear, and now it's time for that to live online. Rendezvu exists because the outdoors deserves its own version of influence, one built on experience, not algorithms. That's the future we're building.