Future Ventures: Scaling with Clarity

Robin Smith — Moving from B2B SaaS to Tech Enabled Services | Future Ventures Podcast Ep. 008

• Maxim Atanassov

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0:00 | 1:01:32

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Robin Smith, a 20-year enterprise software veteran, has worked through all ownership models—bootstrapped, venture-backed, private equity, and public. Most recently, as COO of a PE-backed portco with 1,000+ employees, he led over €200 million in acquisitions during an 18-month roll-up. Now in his mid-40s, he left that world to pursue entrepreneurship through acquisition and found that AI is rewriting the playbook for buying mission-critical software businesses. 

What makes this conversation worth your time is where Robin is standing right now. He knows how PE deals actually work — from the inside, not from a pitch deck. He watched AI gut the economics of traditional SaaS in real time. And he's acting on it, building Stayd as a B Corp roll-up of holiday home agencies in the UK with a thesis that most of the market is still sleeping on. He doesn't sugarcoat the deal that fell apart, he's blunt about where software valuations are headed, and his thinking on outcome-based pricing is ahead of the curve. This is one of the more honest conversations we've had on the show. 

5 Key Topics Covered 

  1. Failed Acquisition, Real Lessons — Robin walks through a competitive sell-side process for a bootstrapped vertical SaaS business, where he lost on valuation and perceived execution risk as an independent sponsor. 
  2. Independent Sponsors vs. Traditional PE — Why sell-side advisors remain skeptical of independent sponsors, what the funding gap actually looks like, and how Robin structured capital for family offices. 
  3. AI's Impact on Software Valuations — How running a financial model through Anthropic's tools turned Robin, an AI skeptic, into a believer, compressing a week of analyst work into hours. 
  4. The Software Commoditization Thesis — Robin's argument that any UI-to-database application has lost its intrinsic value and that real value now resides only where software works autonomously. 
  5. Stayd: Rolling Up Short-Term Rental Agencies — The three-pillar strategy behind Robin's new venture — revenue optimization, agentic workflow automation, and ethical acquisition of holiday home agencies, with a partnership model for founders. 

3 Key Insights 

  1. Buy-side advisors are worth far more than deal execution. Robin expected his buy-side advisor to run the transaction. What he didn't expect was the depth of market intelligence they brought — competitive deal color, LP and GP behavior patterns, and valuation triangulation that validated his bottom-up analysis to within half a turn of revenue. 
  2. The moat in software isn't the interface anymore — it's whether the tool actually does the work. Robin puts it simply: if someone still has to sit at a keyboard and punch data into your system, that software is basically free. The value shows up when technology takes over the labor itself. And if that's true, charging a flat license fee makes no sense. You charge for what the tool delivers. 
  3. Having zero technical debt right now might be the most underrated advantage in the market. Incumbent software businesses are trapped — they have paying customers on legacy systems, finite engineering teams, and AI rewriting the rules around them in real time. Robin bets that starting clean, with no organizational baggage or codebase to maintain, lets you build at a pace that no legacy player can keep up with. 

Links 

Guest Bio

Robin Smith is the Managing Partner of Corinium Capital and the Founder of Stayd, a B Corp roll-up of