Episode Summary:
Ricky Sevta isn’t afraid of hard truths, or hard problems. As the former Chief Revenue Officer at simPRO, Ricky helped scale the company from $10M to $100M ARR, led a $550M capital raise, and expanded the business into global markets. Now, as CEO of Deep Space and a partner at Venture On, he’s back at the beginning, building again. In this episode, Ricky shares the behind-the-scenes realities of scaling a company beyond product-market fit, why founders underestimate the cost of growth, and the personal sacrifices that come with chasing unicorn status. He also reveals how Deep Space is tackling fragmented workflows in construction with modern, AI-powered software, and why pricing, timing, and hiring are all about ruthless clarity. From celebrating too little, to learning how to protect time with family, Ricky unpacks the emotional toll of leadership, how to spot premature market entry, and why customer obsession isn’t optional, it’s survival.
Episode Sponsors:
Chapters:
02:00 – Ricky’s transition from engineer to CRO and global scale-up leader
05:30 – The messy middle: scaling simPRO from $10M to $100M ARR
08:20 – Building structure into chaos: onboarding, playbooks, and the “Lego” method
11:00 – Why product-market fit is never static—especially across geographies
13:30 – Market trumps team: Ricky’s framework for evaluating expansion risks
16:50 – Don’t skip the customer: 40% of Ricky’s time was spent on the ground
19:00 – What “Chief Revenue Officer” really meant at simPRO
22:00 – The traits Ricky looks for when hiring early-stage startup leaders
24:40 – The emotional cost of startup life: family, friendships, and isolation
28:00 – Why founders often create businesses to fix something in themselves
33:00 – Leaving simPRO: starting again with Deep Space and Venture On
37:00 – Building in public and launching an AI-powered construction OS
43:10 – Why the construction industry isn’t “behind”—it’s been underserved
50:00 – Deep Space’s AI agent “Kai” and the platform’s competitive edge
56:00 – How modern architecture unlocks personalization and speed
01:02:00 – Ricky’s take on AI disruption, job loss, and market overreactions
01:10:00 – Pricing strategy: why Deep Space chose fixed pricing over revenue-based models
01:16:00 – Signs it’s time to enter a new market (hint: it’s not when you are ready)
01:22:00 – Product feedback loops and building a customer-driven roadmap
01:27:00 – Celebrating small wins and creating a culture of recognition
01:30:00 – Ricky on joy, drive, and why he’d do it all again—burnout and all
Resources:
🔧 Deep Space – AI construction management platform https://www.deepspacegroup.ai/
👤 Ricky Sevta on LinkedIn https://www.linkedin.com/in/rickysevta/
