Hard Lessons From Wartime with Dennis Velasco of Prosperna
In this episode of Founders Only, we are joined by Dennis Velasco of Prosperna, for an unfiltered and deep dive into the high-stakes reality of leadership that most business books gloss over. Dennis pulls back the curtain on the psychological toll of managing a team, sharing a candid look at the unique stresses and "lonely-at-the-top" difficulties that only those in the driver's seat can truly understand. From the weight of decision-making to the daily grind of aligning diverse personalities toward a single vision, this conversation explores the raw emotional fortitude required to lead a company through the inevitable fires of the startup world.
Beyond the internal struggles of management, Dennis opens up about the external battlefield of fundraising and the grueling reality of facing constant rejection from investors. He discusses the challenge of navigating a sea of conflicting opinions and "expert" advice without losing sight of his original mission. Finally, he highlights how Prosperna is staying ahead of the curve by aggressively integrating AI to enhance adaptability in a rapidly shifting digital landscape.
EPISODE TIMELINE:
00:01:05 - Welcome back: Ron introduces Dennis Velasco of Prosperna
00:04:16 - The pandemic funding era: raising $950K and scaling fast
00:09:41 - Dennis and Ron align: the "people before systems" mistake
00:15:32 - Panic mode: running out of cash and chasing the next round
00:19:29 - Dennis's turning point: when he knew survival mode was the only way
00:23:20 - Preserving culture while slowly reducing headcount
00:28:36 - HR tactics: cutting fast, communicating clearly, and moving forward
00:34:23 - Product-led growth: the early decision that shaped everything
00:40:29 - Going to the US to raise: investor meetings and tough feedback
00:48:20 - Ron's parallel: charging more per client to survive and grow
00:53:34 - Why Guam made sense: Filipino trust + Western purchasing power + USD
00:58:33 - Guam as a bridge market between the Philippines and the US
01:00:33 - USD recurring revenue: the game-changer for Prosperna's survival
01:05:40 - Staying positive: changing the narrative around Filipino SaaS
01:12:24 - AI as the new North Star: rebuilding the product roadmap around it
01:18:03 - The world Prosperna is building: AI-powered tools for SMBs
01:21:16 - AI working 24/7: what agentic roles mean for small businesses
01:24:38 - The opportunity: services companies with an agentic AI backend
01:28:59 - Where Prosperna stands today and the mission going forward
QUOTE/S FROM DENNIS VELASCO:
“Look, as they say, one moment in life does not define your life. Every day is the beginning of the rest of your life, my man. So there's… it's a two-way street. You can't control what other people say. So there are times when the other person also needs to understand the other point of view, which is the company and the mission. Right. So can we all do better the next time and have better restraint? Absolutely. For sure. But I don't think, to be honest with you, for majority of cases, if you know the person, if you know me, if I know you, it doesn't make you a bad person. Everybody has a hiccup. Right. I guess if people want to talk about authenticity, well, be careful of what you ask for. Because if you want the authentic leader, this is what that means. Right. That's how we speak.”
Resources:
Linkedin (Dennis Velasco) : https://www.linkedin.com/in/dennis-velasco/
LinkedIn (Prosperna) : https://www.linkedin.com/company/prosperna/
Website (Prosperna): https://www.prosperna.com/
Links/Sponsors: ;
OneCFO: https://www.onecfoph.co/
This episode is brought to you by Villgro Philippines, Paymongo, GoTyme Bank & SeekCap
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