Episodes

What is the real estate lifecycle and why is this different from other sectors? Why did Derek experience a rebellious phase during college that entailed exploring career options outside of the engineering track he was ushered down? How does one become a strategy consultant by accident? Why did getting to know a tennis shop customer lead to a career change into real estate development? What else did Derek do to go all in on real estate as a profession? Are the advantages to working in a small fam...

Is the headline "Proptech Needs to Die" hyperbole or does it point to a distorted truth? What are the lifecycle stages of ownership and how does this differ by real estate asset class? How did an accounting close process lead to a career interest in data intelligence and analytics? What is the Netflix culture deck and why is Netflix's culture so revered in tech companies? Why was participating in On Deck so beneficial as an aspring entrepreneur? What are some of the challenges faced when transit...

Why did Chase's parents convince him to attend UVA and how has it become one of the best decisions that he ever made? What program offered by the NFL allowed Chase to finish his master's degree? How did a degree in sports administration establish a foundation for Chase's future entrepreneurial endeavors? What is the difference between move-in day and turn at college campus housing? How was Chase able to create a nationwide company helping off campus student housing with turn from an opportunity ...

What does it mean to streamline the real estate industry? How might AI further seep into the proptech sector beyond content creation and visual generation? Will AI be a part of every company going forward or is this a temporary tech fad? What was it like to work (at the time) in the largest square foot building in the US? Are there unique challenges when working for a company that has both employees and unions? How many roles did Ali apply to at Uber before finally getting her foot in the door? ...

Can entrepreneurship be taught in school or does it need to be learned on the job? What sorts of opportunities can you create for yourself by taking a chance and directly immersing yourself in an emerging space? How critical to scaling a business is knowing how to sell? Why is listening an underappreciated aspect of being successful in sales? Can introverted people actually make good sales people? How are entrepreneurs and sales people alike? What is attractive about real estate investing which ...

How did an internship for Senator Barbara Boxer lead to attending George Washington University? What transformative event happened while attending George Washington University resulting in a move back to the West Coast to attend the University of Southern California? How did a family event as a teenager in Ukraine spark an initial interest in real estate? Why leave a promising career in real estate investment banking to move to Hong Kong? How did an investment banking background prove to be a gr...

How did the desire to be a writer lead to an opportunity to be part of the emerging web 2.0 scene within social media marketing? Why were technical skills in account/brand management roles so valued by digital marketing agencies? What are some attributes of successful startup employees that can also make them not the best college or university students? How have the scope of problems that startups are solving for today become much more complicated than those being built in the early days of web ...

How did life on a farm stoke the entrepreneurial spirit of a young kid? What sorts of problem-solving skills were instilled as part of daily life on a farm? How did an advanced engineering degree further complement the entrepreneurial skill set developed growing up on a farm? How did a love for fixing cars and pickups create enough side hustle income to pay for college? What finally compelled a services based entrepreneur to transition to a technology product entrepreneur? How did a teacher dip ...

How would one describe the current state of skilled trades in the built world? What are the transitions that the construction industry is facing? How many open jobs in the skilled trades are there at the moment in the US? Why are skilled tradespeople in the workforce aging out faster than new workers entering the profession? How can an increase in diversity within this industry help alleviate some of the resourcing needs? How can we create excitement around the skilled trade profession so more p...

How has the definition and usage of the term proptech expanded as the space has matured? Why has proptech innovation historically been extremely limited compared to other industries? How did effective data management allow M7 to differentiate itself for other real estate asset managers? Prior to Coyote entering the market, what tools were firms using to manage real estate asset data? Why did M7 decide to spinout Coyote instead of keeping it as a proprietary internal tool? What is the process lik...

Why is the reasoning from first principles approach so successful in unlocking creative solutions to complex problems? What can you do to differentiate true customer needs from the noise of what customers are asking for outloud? How long does it take the average homeowner to save up their down payment on their first home? Why does the real estate industry thrive on information asymmetry? What is the benefit to the individual investor of cutting out the middlemen currently involved with most resi...

From a professional standpoint, why do people choose to pursue a career in consulting? What were the travel advantages of working with real estate consulting clients versus other industries? What were some of the challenges with working with international real estate clients? How did the opportunity to evaluate proptech companies come about within a real estate consulting role? How do generalized skillsets developed while working for consulting companies translate to being an executive at a tech...

Why can there be value in recreating the wheel when first starting out in a new role? How is it that renting an apartment is a much harder and more involved process than people initially imagine? Why have independent landlords traditionally been a neglected customer base for technology companies? How can customer conversations uncover previously undiscovered revenue opportunities? What insights can be acquired by attending customer meetups during the early days of a startup? How can proptech com...

What are the synergies between crypto and real estate? Why has crypto traditionally lacked good real world collateral? Is real estate's % of GDP as large in other parts of the world as it is in the US? What caused the housing correction in China after the initial privatization run-up? What are the benefits of decoupling housing ownership and occupancy? Can technology innovation help solve many of the structural inefficiencies that exist in real estate investing? Are there similarities between th...

How did partnering with realtors through creative strategies lead to a successful insurance business being built at an early age? What challenges do real estate investors who intend to be landlords encounter when trying to get real estate insurance products? Why is it important today to be where the customer is and not rely on or hope that the customer comes and finds you? How did the opportunity arise to work with many of the most prominent insurance companies? What are the advantages of partne...

What is Chat-GPT's definition of proptech? Will Chat-GPT be a future podcast guest of Proptech Espresso? What material value has been generated from the considerable investment in proptech over the last couple of years? Has the use of the term proptech been overextended to the point that almost any company that touches the home is now considered a proptech company? How has a unique bond formed as friends contributed to the successful chemistry as co-founders? Why are traits such as grit and auth...

Does the generalization of the term proptech help those outside the industry establish a framework to start understanding the space? How did a background in consulting establish a strong underlying skillset for being a tech entrepreneur? Why is iterative problem solving important when improving processes for complex businesses? What has been the likely cause of poor tenant experience for renters historically? Why is addressing operations for landlords important in providing an improved tenant ex...

Can rental leases provide a pathway for building a career as a real estate agent? How did a high school friendship uncover the emerging co-living scene in New York? Why are real estate investors critical for the co-living business model? What sorts of opportunities are multifamily operators looking for to be innovative? Why would a successful real estate agent make the jump to a risky proptech startup? What is causing fewer and fewer renters to fit the ideal multifamily renter profile? Why do le...

How does the introduction and application of technology to an industry create a catalyst for change and re-invention? Why did a job at MTV during its heyday lead to a career switch into high finance? How did becoming an intrapreneur create massive opportunities to build new businesses at the intersection of two asset classes? Why can land registry be considered the original blockchain? What has created the trapped equity crisis that American homeowners are experiencing today? How is housing affo...

How can passion projects outside of work and school accelerate learning a new skill? In what ways do government regulations create so many complex challenges for businesses? Why isn't there more effort to invest in regulation reconciliation to alleviate inconsistencies? How has Microsoft leveraged natural language processing techniques and its global data sets to address hyper local and domain specific problems? What is the compelling reason to index every residential property in the world? Why ...

What is the difference between a proptech company and a venture backable proptech company? How does mixed-income housing support diversity and improve the chance for income mobility? Why is housing NIMBYism so pronounced in San Francisco and how does this contribute to its rampant homeless issue? What is the definition of affordable housing and how prevalent is it in the US? Is creating affordable housing only a big city issue or do rural cities also struggle with this? Why are there so many mis...

What compelled a rising star in GE's management training program to pivot and jump to the real estate industry? How did mortgage servicers look to find positive housing outcomes during the great financial crisis and help keep people in their homes? What is the importance of access to capital for real estate? Are there unique challenges you encounter when taking over a company from a founder CEO? How does a finance professional get deeply knowledgeable about the fundamental technology of an organ...

Which industries rely on real estate data beyond the home transaction itself? Why has almost no one heard of RELS? What are the benefits and downsides of being acquired by a co-owner? Why did the appraisal industry need innovation and what was fundamentally broken with it? How did the modern appraisal project come about at Clear Capital and what were there the challenges the team faced? What was it like partnering with the GSEs (Fannie and Freddie) to transform the home appraisal process? Why ar...

Has Amazon morphed into a proptech company? Is the US transforming into a warehouse nation? How did getting punched in the face by the 2008 financial recession force a career pivot into managing bank owned real estate assets? What learnings came from working through the foreclosure process with multifamily properties? Were virtual tours happening in New York City as early as 2006? How a lightbulb moment led to launching a startup developing storefronts into touchscreens for real estate companies...