- The Talent Ledger
- Posts
- The Art of Timing
The Art of Timing
Why the right moment often outweighs the right implementation

𝐖𝐞𝐞𝐤𝐥𝐲 𝐓𝐚𝐤𝐞
Sometimes, great teams build the right product at the wrong time. Other times, good-enough execution, perfectly timed, creates outsized success.
I evaluated two founders this week that perfectly illustrate this dynamic. One caught a regulatory wave with a solution that arrived precisely when customers needed it most, while another built a technically impressive product for a market that doesn't exist yet.
Today, I'm analyzing how market timing can make or break even the sharpest execution - and how to spot markets truly ready for disruption.
𝐅𝐨𝐮𝐧𝐝𝐞𝐫 𝐏𝐫𝐨𝐟𝐢𝐥𝐞𝐬
Founder A | Founder B |
---|---|
📅 Age: Late 30s | 📅 Age: Early 30s |
📍 Geography: Mid-Atlantic | 📍 Geography: Northeast |
📈 Stage: $10K+ in early revenue from 3 paid pilots, pre-seed | 📊 Stage: Fully built MVP, no paying users, $150K+ raised |
🏢 Industry: B2B procurement SaaS for government contractors | 🥽 Industry: VR social platform for remote team-building |
🎓 Background: Former federal procurement officer, 10+ years inside the pain point | 🎨 Background: Design and media studies, experience at major VR gaming studio |
🔥 X-Factor: Launched right as new regulations forced contractors to update their systems | 💡 X-Factor: Beautifully designed product with imaginative vision |
𝐓𝐡𝐞 𝐃𝐨𝐰𝐧𝐥𝐨𝐚𝐝
𝐅𝐨𝐮𝐧𝐝𝐞𝐫 𝐀: 𝐘𝐞𝐬 ✅
This founder's B2B procurement platform demonstrates the power of perfect market timing. They built a vendor management solution just as new regulations forced contractors to modernize their compliance systems.
With only $10K+ in early revenue from their first three customers, the speed to first dollar told the real story - they signed contracts within three months of launching. This quick adoption wasn't luck; it resulted from recognizing a regulatory shift creating urgent demand.
As a former federal procurement officer, they had firsthand knowledge of the problem. This insider perspective allowed them to recognize when the market would suddenly need their solution and be ready when that moment arrived.
Despite lacking startup experience - initially a concern - they quickly converted domain knowledge into paying customers. When customers are actively searching for solutions, even a basic product can gain traction.
This combination of right product, right time, right customer made it a yes.
𝐅𝐨𝐮𝐧𝐝𝐞𝐫 𝐁: 𝐍𝐨 ❌
This founder's VR social platform showcases exceptional execution for a market that doesn't exist yet. The virtual environments were thoughtfully crafted, the avatars were expressive, and the collaborative features were genuinely innovative. From a pure product perspective, this was excellent work.
However, our research revealed a fundamental timing problem. Remote teams simply aren't prioritizing VR solutions yet - they're still struggling with basic collaboration challenges and aren't seeking additional complexity.
Despite having a fully built MVP for months, they couldn't convert enthusiasm into paying customers. The absence of revenue wasn't due to product issues but rather to timing – they were too early by several years.
The founder showed impressive technical and creative skills, but built for a future market rather than a present need. If major shifts occurred or clear enterprise demand emerged, this would be a different conversation.
This combination of strong execution but misjudged timing made it a no.
𝐌𝐲 𝐑𝐮𝐛𝐫𝐢𝐤
𝐀 𝐯𝐢𝐬𝐮𝐚𝐥 𝐛𝐫𝐞𝐚𝐤𝐝𝐨𝐰𝐧 𝐨𝐟 𝐤𝐞𝐲 𝐟𝐚𝐜𝐭𝐨𝐫𝐬 𝐢𝐧 𝐦𝐲 𝐢𝐧𝐯𝐞𝐬𝐭𝐦𝐞𝐧𝐭 𝐝𝐞𝐜𝐢𝐬𝐢𝐨𝐧

This comparison reveals how market readiness can outweigh even exceptional talent and execution, creating a counterintuitive investment decision.
𝐄𝐧𝐠𝐚𝐠𝐞𝐦𝐞𝐧𝐭 𝐂𝐨𝐫𝐧𝐞𝐫
𝐐: 𝐇𝐨𝐰 𝐜𝐚𝐧 𝐟𝐨𝐮𝐧𝐝𝐞𝐫𝐬 𝐢𝐝𝐞𝐧𝐭𝐢𝐟𝐲 𝐭𝐡𝐞 𝐫𝐢𝐠𝐡𝐭 𝐦𝐚𝐫𝐤𝐞𝐭 𝐭𝐢𝐦𝐢𝐧𝐠 𝐛𝐞𝐟𝐨𝐫𝐞 𝐜𝐨𝐦𝐦𝐢𝐭𝐭𝐢𝐧𝐠 𝐭𝐨 𝐛𝐮𝐢𝐥𝐝?
A+ execution on a D- timing opportunity still nets out to a pass. Meanwhile, even a scrappy MVP can fly if the market is begging for a solution.
The most reliable timing signals I look for center around market pull versus push. When potential customers are actively seeking solutions rather than needing education on why they should care, timing is right. Watch for market indicators like regulatory changes creating new requirements, platform shifts enabling new behaviors, or buyers facing urgent pain points they're actively trying to solve.
Sometimes the smartest move is knowing when not to build. If you're consistently hearing "this could be interesting in the future" rather than "when can I start using this?", you're likely too early. Being too early is just as fatal as being too late, but with a longer, more expensive death.
I advise founders to conduct time-to-first-meeting tests before building anything. How quickly can you get potential customers to talk about your concept? When decision-makers eagerly discuss your idea (not just the finished product), the market timing is likely right.
𝐖𝐡𝐚𝐭'𝐬 𝐍𝐞𝐱𝐭?
What would you like to see next in The Talent Ledger? |
𝐂𝐥𝐨𝐬𝐢𝐧𝐠 𝐓𝐡𝐨𝐮𝐠𝐡𝐭𝐬
Market timing can override almost any other founder quality. As I observed in my analysis of Smart Resource Deployment, recognizing the right signals often matters more than having the perfect solution.
The contrast between these founders tells a clear story: one recognized a critical moment when customers suddenly needed a solution, while the other built an impressive product for a future that hasn't arrived.
The ledger entry is clear: bet on founders who can read market timing accurately. Great entrepreneurs aren't just skilled builders – they're attentive listeners who can spot when customers are ready for what they're building.
Auditing more talent next week,
Will Stringer

𝐅𝐞𝐞𝐝𝐛𝐚𝐜𝐤
Did you enjoy this issue?Your feedback will be used to refine this newsletter. |
P.S. If you found value in this entry, add it to someone else's ledger by forwarding this email. If you're that someone, subscribe here to get inside access to how I invest in exceptional people.