Second Century Ventures
430 North Michigan Avenue, Chicago, Illinois, 60611, United States
Overview
Second Century Ventures is a venture capital fund focused on promoting innovation in the real estate industry and helping to enable the entrepreneurial spirit of real estate to thrive. SCV has been fully capitalized by the NATIONAL ASSOCIATION OF REALTORS® (NAR). With over 1.4 million members, NAR is a trade association in the country. NAR can provide immediate strategic value to SCV portfolio companies by allowing them access to the vast resources of a 300-person organization with expertise, influence, and power that comes only by being ingrained in an industry for over 100 years.
- Total investments
- 43
- Lead investments
- 7
- Investments · 12mo
- 6
- Active investors
- 9
Sector focus
- Commercial Real Estate
- Financial Services
- Smart Home
- Venture Capital
Investment portfolio
- TaskHer
Led · Seed · Jul 2026
TaskHer operates an online platform that lists only tradeswomen, enabling homeowners to book and pay verified women tradespeople with pricing set upfront. The company was co-founded in 2022 by Anna and Paul Moynihan after their own experience of being sidelined during a renovation, and it has connected over 4,000 customers with tradeswomen across London. TaskHer has extended its mission into a partnership with Refuge to supply trauma-informed maintenance to domestic abuse safe houses. The platform distinguishes itself from larger UK trade directories by screening specifically for tradeswomen and focusing on visibility to grow demand and supply. In 2024 the company reported 79% revenue growth and has run a Crowdcube campaign as part of its fundraising to date. Planned product and commercial priorities include continued platform development and B2B expansion into housing associations, lettings agencies and women’s refuges.
- SquarePlan
Participated · Seed · Jul 2026
SquarePlan applies artificial intelligence to automate early-stage commercial real estate planning and visualisation, converting simple floor outlines into space plans, cost estimates and 3D, VR and AR visualisations. Its platform is already used by landlords and developers in European commercial real estate, including customers such as Strabag Real Estate and EPP. The company says its automation can shorten early leasing stages by several weeks and reduce advisory and fit-out costs for landlords and occupiers. Founded by Zbigniew Kostrzewa and Łukasz Majewski, the firm has been led by CEO Maciej (Matthew) Markowski since 2023. Financially, SquarePlan has raised $3M in total capital following the $1.8M seed round. The company plans to expand its commercial footprint across the EU, North America and the Middle East.
- Stake
Participated · Equity · Mar 2026
Stake operates a vertically integrated renter platform that now spans apartment search, lease signing, rent payments, and everyday financial wellness. Through its recent acquisition of apartment-locating service UMoveFree and Lighthouse, Stake can surface cash-back deals at the start of a renter’s search and continue rewarding them for on-time rent payments via its FDIC-insured Stake Checking account. The network encompasses more than 550,000 homes nationwide and has delivered tens of millions of dollars in rewards, with UMoveFree alone having served over 5 million renters and paid out $35 million in cash back. Stake reported 4× year-over-year revenue growth in 2025, underscoring accelerating adoption of its platform. Key renter features include immediate cash back at lease signing, automatic credit reporting on rent, and no-fee banking services. For property owners, Stake provides a Loyalty Cloud dashboard and Stake+ incentive engine that align renter savings with property performance. The company plans to use new capital to integrate UMoveFree’s demand engine, expand deal-based rental discovery into additional markets, and accelerate development of its renter savings products.
- Propi
Participated · Seed · Mar 2026
Founded in 2022 by José Mario Ávila and Eduardo Francés, Propi has built a super-app that digitizes the entire real-estate transaction process, from property search and reservation to contract signing, down-payment processing, compliance, and coordination of bank disbursements. The platform currently operates in El Salvador, Guatemala, and Panamá, markets where it has facilitated more than US$300 million in digital real-estate operations since 2023. Its database contains approximately US$4 billion in historical residential inventory spanning new developments, resales, and rentals. More than half of its buyers are Central Americans living abroad, a segment Propi serves through a WhatsApp-based virtual assistant. With fresh capital, the company plans to expand into Honduras, the Dominican Republic, and Costa Rica while deepening its mortgage-credit and pre-qualification integrations with banks. Management is also evaluating entry into a fourth market, with Ecuador and Venezuela under consideration. Propi aims to become the leading digital real-estate hub across the region.
- GXE
Participated · Series A · Oct 2025
Founded in 2020 by Ed Hooper and Andrew Armstrong, GXE offers an all-in-one software platform that enables fund managers, family offices and other investment professionals to handle securities management, investor communications, tax and regulatory compliance from a single interface. The system replaces spreadsheets and disconnected tools, giving users a unified ‘source of truth’ that improves efficiency and builds trust with LPs. GXE already supports thousands of investors across more than 250 funds and special-purpose vehicles, demonstrating early product-market fit. The company’s founders previously built and exited Omny Studio, lending them credibility in scaling SaaS products. With the fresh capital, GXE plans to hire additional software engineers and operational staff to expand the platform and serve its rapidly growing client base, which includes MA Financial, Nash Capital, Westpac-backed Reinventure and Glitch Capital. To date, the fintech has raised a total of US$5.3 million in funding. The oversubscribed Series A underscores investor confidence in GXE’s potential to transform private-asset operations.