What It Really Takes to Scale to $100M: Ricky Sevta on Burnout, Breakthroughs, and Building Again

Episode SummaryRicky 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 Stamps02:00 – Ricky’s transition from engineer to CRO and global scale-up leader05:30 – The messy middle: scaling simPRO from $10M to $100M ARR08:20 – Building structure into chaos: onboarding, playbooks, and the “Lego” method11:00 – Why product-market fit is never static—especially across geographies13:30 – Market trumps team: Ricky’s framework for evaluating expansion risks16:50 – Don’t skip the customer: 40% of Ricky’s time was spent on the ground19:00 – What “Chief Revenue Officer” really meant at simPRO22:00 – The traits Ricky looks for when hiring early-stage startup leaders24:40 – The emotional cost of startup life: family, friendships, and isolation28:00 – Why founders often create businesses to fix something in themselves33:00 – Leaving simPRO: starting again with Deep Space and Venture On37:00 – Building in public and launching an AI-powered construction OS43:10 – Why the construction industry isn’t “behind”—it’s been underserved50:00 – Deep Space’s AI agent “Kai” and the platform’s competitive edge56:00 – How modern architecture unlocks personalization and speed01:02:00 – Ricky’s take on AI disruption, job loss, and market overreactions01:10:00 – Pricing strategy: why Deep Space chose fixed pricing over revenue-based models01:16:00 – 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 roadmap01:27:00 – Celebrating small wins and creating a culture of recognition01:30:00 – Ricky on joy, drive, and why he’d do it all again—burnout and allResources Mentioned🔧 Deep Space – AI construction management platform https://www.deepspacegroup.ai/👤 Ricky Sevta on LinkedIn https://www.linkedin.com/in/rickysevta/Sponsors:Perspective X is supported by our wonderful sponsors:Vanta: Vanta is the all-in-one solution for startups to become compliant quickly and build a security foundation with ease. Startup customers get $1000 off Vanta at dayone.fm/vanta/paulineMighty Partners: Mighty Partners is a growth lender supporting ambitious Australian companies with bespoke debt funding solutions.Day One listeners are invited to book a complimentary venture debt consultation with Mighty Partners. To schedule your call, simply follow the link and mention "Day One Free Consult"dayone.fm/mighty Perspective X is part of Day One.Day One helps founders and startup operators make better business decisions more often. To learn more, join our newsletter to be notified of new Perspective X episodes and upcoming shows. Mentioned in this...

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