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Making HOAs Loved Again: The AI-Native Approach to Managing 200+ Buildings

Making HOAs Loved Again: The AI-Native Approach to Managing 200+ Buildings

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Meet the startup that’s rewriting the rules of real estate—one digital employee at a time.


In this episode of Scaling Without Breaking, host Roland Siebelink sits down with Yotam Cohen, CEO and Co-founder of Daisy, the AI-native property management company disrupting how communities are run.

Yotam reveals how 18 AI agents (complete with names, job titles, and even performance reviews) helped Daisy triple revenue while cutting headcount and keeping customers happier than ever.


From onboarding “Agent Steven” to autonomously catching phishing scams, this conversation uncovers how the future of work is already here.


Key Takeaways:

● How Daisy became an AI-native company from day one

● The truth about AI-human collaboration in real operations

● Why traditional property management is ripe for disruption

● How to build a positive, evolving company culture in a fast-scaling startup

● What autonomous buildings could look like by 2030

If you’re a startup founder, tech innovator, or builder of the future, hit Subscribe and turn on notifications. You should not miss another deep dive into scaling, leadership, and technology that actually works.


Main Topics Discussed

00:02 – 01:41 Introduction of Yotam and Daisy

01:44 – 04:30 AI Agents in Daisy

04:30 – 05:36 “AI Native” Companies

05:36 – 08:20 Day in the Life of an AI Agent (“Agent Steven”)

08:20 – 10:23 Human + AI Collaboration

10:27 – 12:27 Scaling Challenges

12:27 – 13:59 Operational Bottlenecks

13:59 – 15:29 Expansion Strategy

15:29 – 17:31 Customer Growth and Market Demand

17:31 – 18:54 Community Building

19:11 – 20:41 Customer Personas

20:41 – 21:36 Industry Fragmentation and Future Growth

21:36 – 23:14 Managing Global Teams

23:14 – 26:32 Tech Decisions and AI Stack

26:32 – 29:43 Origin Story of Daisy

29:43 – 31:19 Early Challenges and First Clients

31:37 – 33:16 Vision for 2030

33:16 – 35:51 Yotam’s Background

35:51 – 37:18 Entrepreneurial Traits

37:43 – 39:12 Leadership Style

39:12 – 42:11 Core Values

42:11 – 43:33 Source of Positivity

43:54 – 44:39 Parenting Lessons in Leadership

44:45 – 45:29 How to Contact Yotam


Connect on LinkedIn: Yotam Cohen, CEO and Co-founder of Daisy

Website: joinDaisy.com


#AIStartup #PropertyManagement #PropTech #AITransformation #StartupGrowth #RealEstateInnovation #AutonomousBuildings #TechDisruption

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