I used to love the tailwind metaphor. It was one of the cleanest frameworks I had as an advisor. Find a market where the wind is at your back, and your job gets easier. Fight a headwind, and even the best team in the world will struggle. Simple. Persuasive. And, I now think, dangerously incomplete.
I've lived through three versions of market timing. Each one taught me something different about what to watch... and what to ignore.
The first was TravelPerk. Pre-COVID, the company was in hypergrowth, riding the same wave as most SaaS companies: the modernisation of the enterprise tech stack. Businesses were replacing legacy tools with modern software, and TravelPerk was doing that for business travel. Then COVID hit and revenue went to zero. Not declined. Zero. Bill Gates went on television and said business travel would never fully return. Every other SaaS company kept riding the modernisation wave (remote work only accelerated it), which made it worse. The board, understandably, challenged hard. But the leadership team's belief never wavered. The world needed a better business travel solution. That hadn't changed. The wind had changed. The problem hadn't. TravelPerk came out the other side and went back to hypergrowth.
The second was Oliva Health. During COVID, mental health became a boardroom priority. Demand was incoming. Investors were enthusiastic, predicting that Europe would follow the US in treating workplace mental health as essential infrastructure. It felt like a tailwind. It felt like validation. But what we (and investors) believed was a step change turned out to be more of a bubble. As COVID faded, more competitors appeared. Businesses realised the power dynamic had shifted back in their favour, away from employees, and the trend of generous benefits slowed. The early adopters who'd bought in were mostly tech companies, themselves flush with their own COVID tailwind. When their wind faded, ours did too. A tailwind built on a tailwind.
The belief in the problem was real. But it wasn't fully validated by the broader market. We were still in the early adopter phase, and the early adopters were a misleading signal.
The third is now. readywhen.ai is building into what everyone calls the biggest tailwind in a generation: AI. But here's what's different about AI, and why I think the tailwind metaphor finally breaks down completely. AI isn't weather. It's climate. It's a scientific and technological advancement. There's no going back. It doesn't reverse when the economy shifts or a pandemic ends or budgets tighten. The question isn't whether AI will matter. It's whether what you're building with it solves a problem people will pay to fix.
And that distinction has changed how I build. We're not building "an AI solution." We're building to solve a real pain that people want to pay to remove, and using AI to do it in the best way we can. We're not the hot new startup being handed an endless balance sheet. We're treating this as a cash-constrained experiment backed by endless belief. Those are very different starting positions from the ones I've had before.
Three companies. Three relationships with market timing. And the lesson isn't "find a tailwind." The lesson is that tailwinds are unreliable narrators. They feel like validation when they're blowing, and like betrayal when they stop. The only thing that held up, across all three, was whether the problem was real enough that people would pay to solve it when nobody was flush, when it wasn't trendy, when the bubble had popped.
I still hear the tailwind advice everywhere. Pitch decks full of TAM slides and market-timing arguments. I used to nod along. Now I just want to ask one question: if the wind stopped tomorrow, would you still build this?