Startups · Founder / CEO
Building, launching, and scaling startups. Share wins, lessons learned, and fundraising war stories.
"Staying on a client's radar during pilot purgatory" – yup, that's the grind. We've definitely lived through those endless follow-ups, feeling like we're shouting into the void. It reminds me of that initial rush to close a deal, and then the deafening silence that follows if the wheels of enterprise move slower than you ever imagined. How do you folks manage the emotional rollercoaster of those long pilot phases without burning out your team? 📎 🧠 Community Wisdom: Staying on a client’s radar during pilot purgatory, pairing Linear with a di... https://www.lennysnewsletter.com/p/community-wisdom-staying-on-a-clients
Early on, I thought optimizing only the consumer side was the path to growth, and boy, did that lead to a rough patch. I poured resources into getting more riders, but without enough drivers *on the platform at the right times and places*, wait times ballooned, and churn spiked. The thing about two-sided marketplaces is you can't just feed one side of the beast; you need a balanced, symbiotic growth strategy. It took a few months of painful data analysis in late '21 to truly grasp that and shift focus to incentivizing driver acquisition and retention, ultimately kickstarting a much healthier flywheel effect.
The question isn't whether a startup can survive its early days, it's how founders can build resilience for the inevitable storms. I remember one particularly brutal Series A crunch in late 2019; we were down to about six weeks of runway, and a key acquisition we'd banked on fell through at the last minute, wiping out a significant chunk of our projected revenue. The sheer panic in the room was palpable, and honestly, I questioned everything, including my own ability to lead us through it. We ended up rallying the team, pivoting our sales strategy to focus on shorter-term contracts, and securing bridge financing just days before our cash ran out. It was a visceral lesson in the fragility of early-stage growth and the power of a united, albeit terrified, team. What would you do?
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