Stay Paid Podcast – Episode Summary
Episode: The Future of Real Estate: Tech, Mergers & What Agents Must Do Now
Date: February 9, 2026
Hosts: Josh Stike (CMO, ReminderMedia) & Luke Acree (President, ReminderMedia)
Guest: Dave Garland (Managing Partner, Second Century Ventures)
Overview
In this episode, the Stay Paid Podcast dives into the rapidly changing landscape of the real estate industry. Hosts Josh and Luke speak with Dave Garland, a leading venture capitalist shaping real estate's future through tech investments and global accelerator programs. They explore the impacts of recent major mergers, the proliferation of technology and AI, the enduring power of personal relationships, and what agents and entrepreneurs must do to thrive in the coming years.
Key Discussion Points & Insights
1. Industry Shifts: Mergers, Acquisitions, and the Unchanging Core
- Big mergers (e.g. Compass and Anywhere) set new operational standards, yet the core of the business remains unchanged for practitioners.
- Dave emphasizes that the value still lies in the agents themselves, not the brand logos, and high agent attrition rates have remained stable over decades.
- “For most brokers, the most valuable asset walks out the door every single day.” – Dave Garland [01:51]
- Enduring truth: Real estate is, fundamentally, a "belly to belly" business—no amount of innovation will replace the personal relationship aspect.
- “Regardless of whatever innovation you’re using…at the end of the day, this is a belly to belly business.” – Dave Garland [03:16]
2. Technology and AI: Enhancement, Not Replacement
- Second Century Ventures focuses on innovations that keep the practitioner central to the transaction.
- “Innovation happens with the Realtor in mind... Our job is to find the best technologies that keep these practitioners central to the transaction.” – Dave Garland [04:32]
- AI is ubiquitous in new startups, but its role is to augment, not eliminate, agents: it automates certain tasks, enabling agents to deliver better results but not replacing essential trust-based interactions.
- Market Demographics: Older buyers (often 50–60+) are less inclined to trust or use AI-driven processes alone.
3. The "Super App" Debate and Integrated Services
- Industry's current race: building "super apps" integrating all aspects—paperwork, showings, lending, title, inspections—for consumer convenience ([08:08]–[11:39])
- Dave explains there’s tension between who benefits: is it for brokers' efficiency, consumers' convenience, or simply more revenue extraction?
- “At the end of the day, [consumers] want this transaction done right… convenience and speed.” – Dave Garland [10:26]
- Transparency and optionality are essential; too much integration without clarity can frustrate users.
4. Relationship Focus vs. Transactional Focus
- Agents who treat their business as a relationship-driven enterprise (maintaining a "farm" of loyal clients) build longevity.
- “If you’re building relationships, you’re building a career. If you’re just building for transactions, well, then you’re at the whim of the marketplace.” – Dave Garland [13:38]
- You do not need a massive database—“a good farm of 2-300 people” can drive lasting success ([14:02]).
5. Professionalization and the K-shaped Future
- The gap is widening between top producers and average agents: the top 5%-10% operationalize and run their practice like a business, leveraging technology, systems, and data ([18:26]).
- Dave calls this a K-shaped economy—those who adapt, systemize, and innovate rise, while others fall behind.
- “You’re not being replaced by AI per se... you’re just being outpaced by those who are being curious and intelligent.” – Dave Garland [20:43]
6. What Makes a Successful Founder and Startup?
- Grit, curiosity, and problem-solving are key—great founders seek to solve clear, universal pain points for practitioners.
- Second Century Ventures invests in companies that:
- Reduce friction in transactions or ownership
- Strengthen back office operations, financial services, insurtech, and marketing technology
- Enhance the asset’s value over time ([22:54]–[29:32])
- Focus is on “universal problems” that scale across geographies and segments.
7. Notable Successes and Misses in Proptech Investment
- Home Run: DocuSign, brought into real estate by Second Century Ventures, revolutionized contract management and digital transactions ([30:03]).
- “DocuSign wasn’t really in real estate until we actually brought them into the real estate ecosystem.” – Dave Garland [30:15]
- Further success with Notarize (now Proof) in remote online notarization, and BoxBrownie (virtual staging and photo editing).
- Misses: Primarily not getting into some trends or companies early enough, rather than picking outright failures ([32:29]).
8. Expanding Community and Global Reach
- Second Century Ventures has a vast community, partnering with governments, practitioners, and industry associations globally (including Dubai, UK, Canada, and Australia).
- Acts as “fiduciaries of the ecosystem,” aligning innovation with broad industry needs.
9. The Untapped Rental Space
- Rental data and marketing for multifamily and investment owners is a massive greenfield opportunity ([36:28]).
Notable Quotes
- “For most brokers, the most valuable asset walks out the door every single day.” – Dave Garland [01:51]
- “This is a belly to belly business to do it right.” – Dave Garland [03:16]
- “Our job is to find the best technologies that keep these practitioners central to the transaction... If used right, it can create a superpower and that benefits the consumer.” – Dave Garland [04:32]
- “You’re not really being replaced by AI... you’re just being outpaced by those who are being curious and intelligent.” – Dave Garland [20:43]
- “If you’re building relationships, you’re building a career. If you’re just building for transactions... then you’re at the whim of the marketplace.” – Dave Garland [13:38]
- “The K-shaped economy... things like AI make it easier for us to do things we’ve never done before... but it takes dedicated focus.” – Dave Garland [19:37]
- “DocuSign wasn’t really in real estate until we actually brought them into the real estate ecosystem.” – Dave Garland [30:15]
- On advice to his younger self: “Focus on etiquette. In a world where software is commoditized and AI is automating technical work, human skills like etiquette and trust-building are going to be your real key differentiators.” – Dave Garland [37:32]
Timestamps for Important Segments
- Merger and industry overview: [00:47]–[03:33]
- Tech’s role and AI in real estate: [03:33]–[07:36]
- Super apps & integrated services: [08:14]–[11:39]
- Relationship vs. transactional focus: [12:40]–[14:20]
- Professionalization, K-shaped future: [18:26]–[21:50]
- Founder success factors & venture investment focus: [22:54]–[29:32]
- Case studies: DocuSign & Notarize: [29:58]–[32:04]
- Global expansion and partnerships: [33:29]–[36:28]
- Rental space as opportunity: [36:28]–[37:32]
- Advice to his younger self (on etiquette): [37:32]–[39:31]
Actionable Takeaways for Agents & Entrepreneurs
- Double down on relationship-building and etiquette.
- Personal trust and emotional connection outlast brand value and tech advances.
- Focus on the consumer’s real problem.
- Identify the biggest pain point you solve and build your marketing and operations around it.
- Professionalize and operationalize your business.
- Adopt systems, embrace technology, and commit to continuous improvement.
- Treat your “farm” as your core asset.
- You don’t need a massive database; nurture your relationships for sustainable success.
- Stay curious and adopt new solutions, but stay centered on your role in the transaction.
- Leverage technology as your superpower—not your replacement.
- For founders:
- Build solutions for universal problems with scalability, grounded in industry feedback and community.
This episode underscores that, even as technology and mergers sweep through real estate, the true winners will be those who marry innovation with old-school relationship-building, adaptability, and professionalism. AI and apps may streamline tasks, but trust, etiquette, and community remain at the heart of sustainable success.