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Pioneers of Proptech: Tracing the Journeys of HousingWire's Inaugural Tech Trendsetters

Six years after HousingWire first celebrated its Tech Trendsetters, this retrospective delves into the enduring legacies and evolving paths of its inaugural honorees. These individuals, initially lauded for their groundbreaking contributions to housing technology in 2019, have continued to sculpt the future of the mortgage and real estate industries. Their journeys from pioneering roles to establishing new ventures and driving digital transformation underscore the dynamic nature of proptech and fintech. The profound impact of these visionaries is evident in the innovative products, companies, and strategies they have championed, demonstrating a sustained commitment to technological advancement within the sector. As the industry evolves, the groundwork laid by these original trendsetters continues to inform and inspire the next generation of innovators.

Erik Bernhardsson, a standout from the 2019 cohort, initially gained recognition as the Founder and CTO of Better.com. There, he revolutionized mortgage processing by developing an automated loan origination system that significantly reduced reliance on traditional loan officers. Under his guidance, Better.com processed nearly $4 billion in loans, reaching a monthly production of $350 million. In 2021, Bernhardsson transitioned from Better.com to launch Modal Labs in New York City. As its Founder and CEO, he now spearheads the creation of sophisticated machine learning infrastructure tools, empowering data teams across various industries with advanced analytical capabilities.

Stacy Hoover, another distinguished honoree, made her mark as the Head of Product at Reali in 2019. Her leadership was instrumental in implementing a scalable market expansion model and introducing an AI-driven Price Predictor tool. She also played a pivotal role in the acquisition of Lenda, an online mortgage lender, and fostered strategic alliances with firms like Hippo Insurance and Lemonade to broaden customer benefits. Today, Hoover serves as the Chief Product Officer at Ellevest, a financial services platform tailored for women, a position she assumed in July 2022. Prior to this, she held a Senior Director of Product role at The RealReal and other key product leadership positions at Reali until March 2021, consistently driving innovation in financial technology.

Mike Cagney, recognized in 2019 as the CEO of Figure Technologies, was at the forefront of integrating blockchain technology into home equity, mortgage, and secondary market lending. His current endeavors include serving as Executive Chairman of Figure Technology Solutions and CEO of Figure Markets, roles he adopted following a significant corporate restructuring in 2024, which spun off Figure Lending. Figure Markets is actively preparing for an initial public offering (IPO), having reported robust revenue growth of 22% year-over-year and achieving profitability in the first half of 2025, signaling continued strong performance in decentralized finance.

Gary Beasley, celebrated as CEO and Co-Founder of Roofstock in 2019, was honored for his visionary approach to transforming single-family rental (SFR) investment. His leadership has been crucial in the expansion of Roofstock's marketplace dominance, further solidified by a merger with Mynd in 2024. Beasley's consistent innovation and impact within the housing sector earned him additional accolades as a HousingWire Vanguard in both 2019 and 2020.

Briana Ings, formerly Briana Whelan, received recognition as Director of Product at Snapdocs in 2019. She spearheaded the development of the company’s digital closing platform, integrating lending and settlement services through automation and AI to streamline hybrid and eClosings. Her innovations reduced in-person closing times dramatically, often to as little as ten minutes. Currently, Ings is the Chief Product Officer at Snappt Inc., a leading document verification platform for the multifamily housing sector. Under her product leadership, Snappt has analyzed over 12 million documents, successfully preventing more than $1.8 billion in potential bad debt, and continues to set benchmarks for fraud prevention in real estate leasing.

The trajectories of these initial Tech Trendsetters vividly illustrate their sustained influence and adaptability within the ever-evolving landscapes of mortgage and real estate technology. Their ongoing contributions highlight a persistent drive to innovate and reshape industry practices. These leaders not only laid significant groundwork for digital transformation but continue to actively participate in pioneering new solutions and strategies. Their careers serve as a testament to the powerful impact of visionaries in propelling technological progress and setting new standards for efficiency and user experience in critical economic sectors.

MegaStar Financial Services Appoints Mortgage Industry Veteran as Chief Revenue Officer

MegaStar Financial Services recently announced a significant leadership addition, welcoming Mickey Schilling, a seasoned professional with a quarter-century of experience in the mortgage domain, as their new Chief Revenue Officer. This strategic move is poised to bolster the company's market presence, with Schilling tasked with enhancing production, cultivating revenue streams, and guiding the organization's expansion efforts into uncharted territories. Her extensive background positions her as a key player in driving the firm's ambitious growth objectives.

The CEO of MegaStar Financial Services, Anita Padilla-Fitzgerald, lauded Schilling's appointment, highlighting her unique blend of strength, leadership, and genuine commitment. Padilla-Fitzgerald expressed inspiration at securing a female leader of Schilling's caliber, emphasizing MegaStar's robust foundation for development. Schilling, in turn, articulated her decision to join MegaStar, citing the firm's stability, technological prowess, and leadership as ideal elements for fostering expansion. Prior to her current role, Schilling held several prominent positions at Highland Mortgage, including Chief Strategy Officer, and contributed significantly to The Mortgage Firm, First Landmark Bank, Franklin American Mortgage Company, and Movement Mortgage over the last decade.

This appointment underscores MegaStar Financial Services' dedication to reinforcing its leadership team with top-tier talent. By bringing in individuals with proven track records and forward-thinking strategies, the company aims to not only navigate the complexities of the mortgage industry but also to set new benchmarks for success and innovation. The synergistic blend of experienced leadership and a robust operational framework creates a fertile ground for sustained prosperity and impactful contributions to the broader financial sector.

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Victorian Police Cell Block in Nuneaton Goes Under the Hammer

A truly unique piece of Victorian architecture, which once housed police holding cells and more recently served as a vibrant bar and restaurant, is set to captivate buyers at an upcoming auction. This character-filled building in Nuneaton, Warwickshire, presents an extraordinary opportunity for those seeking a distinct property project or a commercial venture. Its rich history and preserved original features make it a standout listing in the current real estate market, offering a glimpse into the past while holding immense potential for future transformation.

A Historical Landmark on the Auction Block in Nuneaton

In the heart of Nuneaton, Warwickshire, a magnificent Victorian edifice, boasting a colorful past as both a police cell block and a lively establishment known as 'The Jailhouse,' is preparing to face the gavel. On the crisp autumn day of September 18th, property aficionados will converge at Auction House Coventry & Warwickshire, with the bidding anticipated to commence at a guide price of £170,000.

This striking red-brick structure, adorned with traditional crenellations, encompasses a generous 2,126 square feet across two spacious floors. Its interior is a captivating blend of history and recent commercial use, featuring an array of intriguing elements such as genuine barred windows, beautifully exposed brick walls, and grand vaulted ceilings. Evidence of its more recent incarnation as 'The Jailhouse' bar and restaurant is also visible, including what appears to be a former coat check area and bar counter.

The building's layout currently includes a bar area, dining sections, kitchens, a cellar, restroom facilities, and a staff room, reflecting its most recent commercial operation. The expansive ground floor covers 1,653 square feet, while the upper level spans 476 square feet. Historically, it is believed that the property contained a dozen holding cells, evenly distributed between the two floors.

Sally Smith, a distinguished auctioneer with Auction House Coventry & Warwickshire, emphasized the building's distinctive narrative. She remarked, "The Jailhouse traces its origins back to the Victorian period, when it was used as police holding cells. Most recently, it has been a beloved bar and restaurant, where local residents enjoyed countless evenings of live music. This iconic building now stands at the threshold of its next chapter. Regardless of the path its new custodians choose, its original features will undoubtedly continue to imbue it with remarkable character."

Adding to its commercial appeal, the former bar possessed a license allowing it to operate until 3 AM and permitted outdoor seating on the pavement. Nuneaton, a bustling town with a population nearing 89,000, sits conveniently close to the Leicestershire border. The town is notably the birthplace of the renowned author George Eliot (Mary Ann Evans), who entered the world on a farm on the outskirts of Nuneaton in 1819 and spent a significant portion of her early life there.

Recent property data from Rightmove indicates that the average house price in Nuneaton over the past year stood at approximately £252,136. Semi-detached residences were the most frequently sold properties, averaging £232,453. Detached homes fetched around £343,278, while terraced houses commanded prices averaging £176,596. Property values in the area have seen a positive trend, increasing by two percent over the preceding year.

A Catalyst for Imagination: The Potential of Repurposed Spaces

This auction of the Nuneaton police cell block turned bar serves as a powerful reminder of the immense potential held within repurposed historical structures. It sparks a compelling discussion about how forgotten or abandoned buildings can be revitalized, breathing new life into communities and offering unique living or commercial opportunities. The blend of historical charm with modern functionality requires visionary thinking and creative adaptation. For individuals or developers daring enough to take on such a project, the rewards extend beyond mere financial gain, encompassing the preservation of heritage and the creation of truly exceptional spaces that tell a story. This property challenges us to look beyond conventional real estate and consider the intrinsic value and narrative potential embedded in every brick and beam of our architectural past.

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