How does the resident experience tie back to property operating economics? What were the contributing factors to the early serial entrepreneur ventures that David dabbled in? Where did David's early interest in technology stem from? How is the origin story of DoorLoop tied to David's prior startup PracticePanther even though these two companies are in completely unrelated industries? Why is the property management software space filled with so much competition and despite this why are there more entrants each year? How do easy-to-use software development tools fuel the creation of products that are in fact not viable businesses? Why is having a founding team so important when starting a new SaaS business? How was launching in Covd different than expected for DoorLoop? Why is it important to capture customer feedback from all engagement systems and not just through annual customer surveys? How is DoorLoop integrating AI across its solution stack?

David Bitton - Co-founder of DoorLoop, joins Proptech Espresso to answer these questions and discuss how real estate investing alongside his parents after college led to a brief career as a realtor and ultimately set the stage for becoming a proptech founder.

Why is access to information a cornerstone component of proptech? How did Zillow and the Zestimate fundamentally change access to home valuations for homeowners and homebuyers? What are the important lessons that athletes can take from losing and positively apply to their professional careers? For Alex, what resonated about the construction industry and the people involved in it? Which lessons stood out to Alex from working as a salesperson for a non-0category leader? What are the similarities and differences between a heavy equipment dealership and a car dealership? Why is equipment downtime so crippling for construction businesses? What insight did Alex uncover as he took ownership of the services and parts business at Flagler? Why are there so few heavy equipment technicians? What percentage of heavy equipment service work is done in the field? Why are the pay economics of technicians so skewed at heavy equipment dealerships? How did Heave change the game for heavy equipment technicians? Why is technician selection by customers such a powerful feature within Heave? What are some of the challenges of building Heave's heavy equipment labor marketplace?

Alex Kraft - CEO and founder of Heave, joins Proptech Espresso to answer these questions and discuss why institutional knowledge of heavy equipment sales and service is so critical for designing a digital solution for this corner of the construction industry..

Can proptech be defined as the modernization layer for the built world? How did the Rabine family business grow from a local mom-and-pop services business to the national multi-business unit holding company that exists today? Why did technology adoption opportunities and business model scalability convince Austin to take a leadership role within the family paving business? What lessons did Austin learn from founding several contech businesses? Why are pavements and roofs the largest ongoing operating expense for a real estate owner? How does the negligence of pavement maintenance result in soaring delayed repair costs? Why was the Rapine Pavement Condition Report so valuable for facility owners? Why was it necessary to rethink the end-to-end process of the condition report to be technology-driven in order to scale this business opportunity. Why did Rabine produce these condition reports at no cost? Why was satellite imagery not a viable option for capturing the necessary pavement and roofing images? What was it about drones and their image capture capability that differentiated them from other solutions that Rabine Companies was investigating? Why did Austin and the executive team at Rabine Companies ultimately decide to spin the SITE business out as a separate independent company? What additional analytics are possible through drones which was not possible with onsite humans? How is SITE utilizing AI in its product suite?

Austin Rabine - CEO and co-founder of SITE Technologies, joins Proptech Espresso to answer these questions and discuss how his parents' enthusiasm for entrepreneurship played a pivotal role in convincing him to join the family business.

How did the complexity of the protech industry spark Diane's interest in taking on the challenges of building a company in this space? What was it like building an adtech startup during the Internet 2.0 heyday? How is the current AI boom similar to the Internet 1.0 era? Why did Diane jump from adtech to fintech? What has contributed to the technology in the mortgage space being so outdated? Why are the mortgage files created during the origination process unclean and riddled with incorrect information? How have the interest rate cycles and associated hiring/firing sprees contributed to many of the technology challenges that the mortgage industry is facing today? Why have industry regulations obsoleted certain mortgage industry technologies? Why was it important for TidalWave to be an AI-first mortgage technology company? What is the difference between an AI solution and an AI wrapper? Why is a mindset of AI support instead of AI replacement important for CIOs to have today?

Diane Yu - CEO and co-founder of TidalWave, joins Proptech Espresso to answer these questions and discuss how her first interaction with a computer as a child was so magical and set her on a lifetime journey of working with computers.

Are there industries outside of real estate where the asset has as many lifecycles? What were some of the problems that Vikas dealt with at Amazon Robotics while working with AEC professionals when building new logistics warehouses? How did growing up in a family-owned manufacturing business influence Vikas' later career pursuits? Where did Vikas' early interest in robotics come from? Why is system design as important as the underlying R&D in robotics? What is a mobile electronics company? Why was Kiva SYstems fundamentally different from other robotics companies of its time? What realization did Amazon have that led it to the conclusion that it was a strategic imperative to purchase Kiva Systems? How was Amazon able to finally achieve same-day shipping with the integration of Kiva Systems? What insights are needed to change problems that appear to be qualitative to actually be quantitative? Why did it take Vikas 5 years to earn his master's degree from MIT? What event led to Vikas' deep introspection and the desire to work on problems reducing carbon emissions? Why did Vikas not focus on farming as an industry where he could work on decarbonization? What was Operation Breakthrough? Why is solving the missing housing issue not a mass production problem but rather requires a mass customization approach? What is different about Reframe's business model from other off-site construction companies? How is air tightness related to wildfire resiliency?

Vikas Enti - CEO and co-founder of Reframe Systems, joins Proptech Espresso to answer these questions and discuss how his interest in space and space exploration drove his belief that in the future the most interesting work would be in automation and robotics.

In major real estate downturns, who has all the real estate business? What do real estate agents need to do differently in a real estate recession? What was the innovation that Trulia and Zillow brought to the home buying industry? Why has Zillow been detrimental to so many real estate agents? What middlemen artificially add costs to the home purchase transaction? How did Rob transition from being a vendor of Chad's to being an investor and co-founder in his technology solution? Why has professional honesty been an important cornerstone of Swyvvl's success? How was personal sacrifice necessary for Chad to be successful with its brokerage business? Why are consistent client leads so hard to come by for real estate agents? What has traditionally caused real estate agents to shy away from brokerage CRM solutions in the past? How has Swyvvl flipped the business model for real estate agents in order to create more economically beneficial outcomes?

Chad Link and Rob Brower - co-founders of Swyvvl, join Proptech Espresso to answer these questions and discuss how an early development /design oversight demonstrated the personal integrity and commitment that laid the foundation for a future co-founder relationship.

Should proptech be defined as a technology that solves a problem in the real estate industry? What made programming easier for Eleni than learning to read and write English? Why is computer science considered a creative science? What were the challenges of often being the sole female student in computer science classes? How did Eleni convince her father to switch from investing in commercial real estate to residential real estate? What was so attractive about the opportunity to join Wise Agent? Why was starting a mentorship program for young developers at Wise Agent so fulfilling for Eleni? Why is understanding the economic incentives of stakeholders so important for developers and product managers? How does Eleni differentiate between programmers and software developers? Why is there so much churn in the real estate agent industry and how might better training reduce this? Why hadn't a platform for real estate creators been created before OnTrack Agent? What are the challenges with rebuilding a platform from the original technology it was built on? Why are service businesses so difficult to scale? What makes digital rights management a huge challenge for real estate creators? Why is solving the demand aggregation side of the real estate creator marketplace part of OnTrack Agent's magic sauce? What makes video content so powerful for real estate creators? Why do real estate agent entrepreneurs need to learn such a diverse skill set to successfully run their business? What can be done to further promote women entrepreneurs and leaders in proptech?

Elenis Sommerschield - CEO of OnTrack Agent, joins Proptech Espresso to answer these questions and discuss how her mother's encouragement convinced her to pursue a degree in computer science instead of dropping out of university and going to culinary school

What inspired Karly and Alena to found Hardline and how did their professional journeys shape the company’s mission? What are the biggest operational pain points Karly saw construction teams face that technology failed to address effectively? How does Hardline define “on-site tech enablement” and why is this an overlooked opportunity in the broader contech space? What were the early customer signals that validated the need for Hardline’s solution? How did time in the field influence Hardline's product design decisions and what constraints did they deliberately build around? Why does Hardline emphasize frontline usability over back-office integrations? How does Hardline think about trust-building with trade partners and GCs in an industry often slow to adopt change? What role did bootstrapping play in refining Hardline’s go-to-market strategy and product-market fit? How has the team navigated fundraising and investor education for a company rooted in field operations rather than data analytics? Why do Karly and Alena believe the next wave of construction technology will be shaped by founders with firsthand experience in the trades?

Karly Heffernan and Alena Tuttle - co-founders of Hardline, join Proptech Espresso to answer these questions and discuss the decisions to pursue passion at work with tech startups over lucrative established professional careers.