In this episode of the Generations of Wealth Podcast, Derek sits down with Dana Dunford, co-founder of Hemlane, to explore how technology, AI, and better systems are changing property management.
Dana shares her journey from working at Apple and Nest to becoming a real estate investor and building a property management technology company now used across approximately 107,000 rental units. Her original vision was simple but ambitious: give real estate investors the ability to know what’s happening with their rentals and manage them from virtually anywhere.
Derek and Dana also go beyond property management, discussing entrepreneurship, choosing the right investors and partners, building high-performing teams, thinking 10X instead of 2X, and why staying actively involved in real estate makes Dana better at building technology for investors.
Watch the episode here
Listen to the podcast here
Overview
Dana’s exposure to real estate began around 2010 through her sister and brother-in-law, who were investing in rental properties. At the time, Dana was working at Apple in new product introductions and later moved to Nest, where she saw firsthand how technology could make managing a home remotely easier.
But she noticed a major disconnect.
Technology could let someone control their own home remotely, yet rental property management was still heavily dependent on outdated systems, manual communication, and overworked local property managers.
That realization eventually became Hemlane.
Dana’s vision was to combine technology with people and processes so investors could manage rentals remotely while still creating a better experience for tenants. Rather than making small improvements, her team focused on solving what she calls 10X problems—reducing delinquencies, shortening vacancy periods, improving communication, and making operations more efficient.
Today, Hemlane oversees approximately 107,000 rentals, with roughly 30,000+ receiving additional day-to-day management assistance such as tenant communication, delinquency management, and maintenance coordination.
The conversation dives into several bigger entrepreneurial lessons as well, including the importance of choosing the right people.
Dana explains that the wrong investors, partners, or team members can derail even a great business. She and Derek discuss trusting your instincts, surrounding yourself with thoughtful people, and understanding that sometimes accepting the wrong capital can create years of unnecessary headaches.
Dana also shares her philosophy for building a lean, high-performing team. Rather than hiring simply to increase headcount, she focuses on experienced A+ players who can use AI and technology to dramatically increase their output.
The episode also explores Hemlane’s approach to:
- Tenant placement and screening
- Self-guided property tours
- Rent collection
- Maintenance coordination
- Delinquency management
- Lease renewals
- AI-assisted property management
- Remote rental ownership
- Scaling from a few rentals to hundreds or thousands
Dana remains an active real estate investor herself because she wants to experience the same challenges her customers experience and use those lessons to continue improving the platform.
One of the strongest ideas from the conversation is:
Don’t simply ask how you can make something twice as good. Ask what it would take to make it 10X better.
Key Takeaways
- Technology should solve real operational problems—not simply add more features.
- AI can make property management teams significantly more efficient.
- Property management ultimately comes down to people and operations.
- Choosing the right investors and business partners can make or break a company.
- A smaller team of exceptional people can outperform a much larger average team.
- Real estate investors should think about the tenant experience as part of profitability.
- Remote rental ownership becomes much easier with the right systems.
- Entrepreneurs should sequence growth instead of trying to build everything at once.
- Staying active in your industry helps you understand what customers actually need.
- Thinking 10X instead of 2X forces you to approach problems differently.
Relevant Topics Discussed
- Property management
- Artificial intelligence & automation
- Remote real estate investing
- Rental property technology
- Tenant screening & placement
- Rent collection
- Maintenance management
- Building high-performing teams
- Raising capital & choosing investors
- Entrepreneurship
- Scaling a technology company
- 10X thinking
Why Should You Listen?
If you own one rental property or hundreds, this episode challenges you to think differently about how you manage your portfolio.
Dana doesn’t approach property management simply as software. She looks at the entire experience—from the moment a prospective tenant inquires about a property through screening, leasing, rent collection, maintenance, and renewals.
It’s also a great conversation for entrepreneurs. Dana openly discusses what she would do differently if she were starting again, why the people surrounding your business matter so much, and why sometimes starting smaller can actually help you scale faster.
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About Dana Dunford
Dana Dunford is the CEO of Hemlane, a venture-backed property management platform with over 103,000 rentals and $1BN in payments processed. She is a strong advocate of purchasing properties anywhere, as the best investments are not typically in your backyard. She supports real estate investors in setting up the most intelligent process to manage rentals from a distance, while connecting them with local, licensed professionals. In 2018, Dana was named one of the top 20 women leaders and influencers in commercial real estate tech.
Dana previously worked at Apple on their worldwide financial planning and analysis team and at Nest, the home technology company acquired by Google for $3.2B, in business development. She received her MBA from Harvard Business School. In her free time, Dana is an avid equestrian, paraglider, and skier. She is the first woman to win a calf dressing championship belt buckle at the CA Rodeo. She takes risks in her personal life but spends her work life advocating technology and prudent spending for a risk-mitigated solution to real estate management.