Ollie has raised $38.3M in total across 4 funding rounds.
Ollie's investors include Alumni Ventures, Arrive, FPV Fund, Meritech Capital Partners, Sequoia Capital, True Ventures, Clearstone, Garden City Companies, Shane Battier, Spark Capital, Accomplice VC, Founder Collective.
Ollie refers to multiple technology companies, with the most prominent being a PropTech co-living rental platform founded in 2015 and headquartered in New York, NY. It operates a platform for shared living spaces, serving urban renters seeking affordable, community-oriented housing, and has grown to over 150 employees worldwide while addressing housing shortages in high-cost cities.[1]
Other notable Ollies include an AI-powered mental health platform (Ollie AI, founded 2020) that provides employee wellness assessments, coaching, and risk detection for global enterprises[2][3]; a family meal planning AI tool that customizes recipes and grocery lists for parents[4][5]; and brewery management software helping craft brewers with production, forecasting, and operations[6]. A smaller IT consulting firm also exists[7]. This analysis focuses primarily on the PropTech Ollie due to its scale and search prominence, with notes on others where relevant.
The PropTech Ollie was founded in 2015 in New York amid rising urban housing costs and demand for flexible co-living options post-recession. It emerged from the need to modernize shared rentals, evolving from early pilots in NYC to a global platform with 150+ employees, leveraging the city's talent pool for engineering, product, and sales teams at its 140 Broadway headquarters.[1]
Ollie AI (mental health) launched in 2020 in Wilmington, DE, at the height of pandemic-induced workplace stress, raising angel funding to build AI coaching and assessments as an alternative to traditional EAPs.[2][3] The meal planning Ollie (Your Family AI) started more recently, focusing on parental efficiency without specified founding details.[4][5] Brewery Ollie grew from craft industry pain points, now serving thousands from 1 BBL to 20,000+ BBL operations.[6]
The PropTech Ollie rides the co-living and PropTech wave, fueled by millennials/Gen Z prioritizing flexibility amid housing crises and remote work shifts—NYC's ecosystem amplifies its influence on urban real estate innovation.[1] Ollie AI taps workplace mental health tech boom (part of 791+ firms in the sector), where post-COVID demand for AI-driven, scalable wellness outpaces traditional services, serving digital health's $11,315+ vendors.[2][3]
Meal planning Ollie aligns with consumer AI for family life, reducing daily stresses in a multitasking era.[4][5] Brewery software supports craft beer's digital transformation, enabling small operators to compete via data tools.[6] Collectively, these Ollies exemplify niche PropTech/HealthTech/SaaS plays, influencing ecosystems by democratizing access—PropTech reshapes rentals, wellness AI boosts retention, and vertical software drives efficiency in underserved markets.
PropTech Ollie is poised for expansion beyond NYC, capitalizing on hybrid work and housing shortages with its operational hub as a growth foundation.[1] Ollie AI will evolve with AI advancements in predictive health, potentially dominating enterprise wellness as mental health mandates grow.[2][3]
Meal and brewery tools may add premium features amid AI personalization trends.[4][5][6] Across variants, expect deeper integrations (e.g., VR co-living tours, advanced health forecasting) shaped by economic recovery and AI ethics focus—reinforcing their role as agile solvers of everyday tech gaps, much like their origins in real user pain points.
Ollie has raised $38.3M across 4 funding rounds. Most recently, it raised $21.0M Series D in April 2024.
| Date | Round | Lead Investors | Other Investors |
|---|---|---|---|
| Apr 1, 2024 | $21.0M Series D | Alumni Ventures, Arrive, FPV Fund, Meritech Capital Partners, Sequoia Capital, True Ventures | |
| Aug 1, 2019 | $280K Venture Round | Alumni Ventures, Arrive, Clearstone, FPV Fund, Garden City Companies, Meritech Capital Partners, Sequoia Capital, True Ventures, Shane Battier | |
| Aug 1, 2017 | $13.0M Series A | Spark Capital | |
| Oct 1, 2016 | $4.0M Seed | Spark Capital, Accomplice VC, Founder Collective, Project 11, TLV Partners |
