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.

Time Stamps

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 Mentioned

🔧 Deep Space – AI construction management platform https://www.deepspacegroup.ai/

👤 Ricky Sevta on LinkedIn https://www.linkedin.com/in/rickysevta/

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