Spencer Rascoff

Background

Spencer Rascoff is the Co-Founder and General Partner of 75 & Sunny, a Los Angeles-based venture fund and startup studio he founded in 2020 ¹². He is currently also serving as Chief Executive Officer of Match Group, a role he assumed in February 2025 after serving on the Match Group board since March 2024 ³⁴.

Rascoff graduated cum laude from Harvard University in 1997 ³⁴. He began his career as an investment banker at Goldman Sachs before moving to private equity at TPG Capital ⁴⁵.

At age 24, Rascoff co-founded Hotwire.com, an online travel company that was sold to InterActiveCorp in 2003 for $685 million ⁵⁶. After the acquisition, he served as Vice President of Lodging at Expedia ⁵.

In 2005, Rascoff co-founded Zillow Group, where he held multiple roles including COO, CFO, and VP of Marketing before becoming CEO in 2010 ⁵⁶. As CEO, he led the company through its 2011 IPO, oversaw 16 acquisitions including Trulia for $2.5 billion, and grew the company to over 4,500 employees, $3 billion in revenue, and a $10 billion market capitalization ⁵⁶. He stepped down as CEO in February 2019 and resigned from Zillow’s board in April 2020 ⁵.

Through 75 & Sunny Labs, Rascoff has co-founded several additional companies including Pacaso (fractional second-home ownership), dot.LA (LA tech news), Queue, Recon Food, and heyLibby ¹². He also co-chaired Supernova Partners, launching two SPACs: Supernova I merged with Offerpad in a $3 billion deal, and Supernova II merged with Rigetti Computing in a $1.5 billion deal ⁷⁸.

Rascoff has served on the boards of Palantir Technologies, TripAdvisor, Zulily, and Varo Bank ³⁹. He is the author of the New York Times bestselling book “Zillow Talk” and hosts the “Office Hours with Spencer Rascoff” podcast ¹¹⁰. He also teaches at Harvard College and Harvard Business School ¹.

Stated Thesis

(Self-reported: These represent what Rascoff says publicly about his investing approach. See Inferred Thesis for analysis of actual investment behavior.)

75 & Sunny describes itself as a firm that “incubates and invests in bold solutions to everyday problems” ¹.

Rascoff has described his fund’s allocation as roughly even across four sectors: “about a quarter of that is in prop tech, about a quarter of it is in B2B SaaS, about a quarter is kind of creator economy or Hollywood meets Silicon Valley type stuff, and a quarter is just other things I find interesting” ¹¹.

On founder selection, Rascoff has stated: “I look for grit — somebody who has something to prove to somebody, and who has a chip on their shoulder — someone who’s willing to run through walls for that company and that idea” ¹⁰. He has also said: “I’ve learned that there is no such thing as a great idea or a great founder; there are only great founders for specific great ideas. The Founder has to be passionate about the specific problem that the startup is trying to solve” ¹⁰.

He has expressed a preference for repeat founders: “Ideally it’s a second-time founder, so they’ve learned from their mistakes on someone else’s investment” ¹⁰.

Rascoff has indicated a shift toward deeper involvement: “I’m deemphasizing in that early-stage angel investing and I’m spending more time focusing on the incubations partly because I find it more rewarding to work more closely with the team” ¹¹.

On AI investing, he advises portfolio companies to “go deep in certain verticals” to avoid becoming “lightweight wrappers on top of LLMs” ¹¹.

He has also stated: “What I am most passionate about is helping people democratize access to things that they might not otherwise have access to” ¹².

Inferred Thesis

The analysis below is based on 22 verified investments from 75 & Sunny’s portfolio page, press coverage, and aggregator databases ¹²¹³¹⁴.

Sector concentration (based on 22 verified investments): - Proptech / real estate: 8 of 22 (36%) — Pacaso, Arrived Homes, Crexi, HostGPO, Ohana, Setpoint, Baton, Permitflow - Consumer / marketplace: 5 of 22 (23%) — Cameo, Sensible Weather, Queue, Recon Food, Fernish - B2B SaaS / enterprise: 4 of 22 (18%) — heyLibby, AllVoices, Apex, Blockchain.com - Deep tech / space: 3 of 22 (14%) — Relativity Space, SpaceX, Rigetti Computing (via SPAC) - Fintech: 2 of 22 (9%) — Varo Bank, Blockchain.com

Key patterns:

• Proptech dominance despite stated diversification: While Rascoff describes a roughly even four-way split across sectors, proptech and real estate represent 36% of verified investments — the single largest category by a significant margin. This aligns with his operational background at Zillow rather than his stated thesis of equal sector distribution.

• Hybrid investor-operator model: Rascoff’s model for incubated companies (Pacaso, Queue, Recon Food, heyLibby) involves larger ownership stakes of 10-20% with $250K-$1M checks ¹¹, compared to passive angel investments of $50K-$100K in external companies. The incubation side is his primary focus by his own admission.

• Stage preference: The portfolio skews heavily toward seed and Series A, consistent with his stated $100K-$5M check size and the fund’s $62M size ¹³. His participation in later-stage rounds (e.g., Relativity Space Series C/D/E) appears opportunistic rather than systematic.

• LA-centric geography: In 2020, 25 of 39 investments (64%) were in Los Angeles-based companies ². The portfolio shows a strong LA bias, consistent with Rascoff’s base in Santa Monica and his role co-founding dot.LA.

• Democratization theme: Multiple investments share a theme of making traditionally expensive or exclusive products more accessible — Pacaso (fractional vacation homes), Arrived Homes (fractional rental property investment), Varo Bank (digital banking) ⁹¹⁵. This pattern matches his stated passion for “democratizing access.”

• Co-investor patterns: Sample too small to identify reliable co-investor patterns at this time. Notable co-investors include Jeff Bezos and Marc Benioff (Arrived Homes) ¹⁵, and Navitas Capital (HostGPO) ¹⁶.

Note: This analysis is based on 22 publicly verified investments. Rascoff claims to have invested in over 100 companies ⁹, and 75 & Sunny Ventures invested in 39 companies in 2020 alone ². The verified portfolio represents a fraction of total investments, and the sector breakdown may shift with more complete data.

Portfolio

This table represents approximately 22% of Rascoff’s claimed 100+ investments. Only investments with publicly verifiable sources are included.

In Their Own Words

“About a quarter of that is in prop tech, about a quarter of it is in B2B SaaS, about a quarter is kind of creator economy or Hollywood meets Silicon Valley type stuff, and a quarter is just other things I find interesting.” — Spencer Rascoff, LA Venture podcast ¹¹

“We’re in about 60 or 70 companies, but what I spend most of my time doing is incubating new startups.” — Spencer Rascoff, LA Venture podcast ¹¹

“My model is for us to put in between 250,000 up to 1 million dollars and end up owning somewhere in the 10-20 percent range.” — Spencer Rascoff, LA Venture podcast, on incubated companies ¹¹

“I’ve learned that there is no such thing as a great idea or a great founder; there are only great founders for specific great ideas.” — Spencer Rascoff, lessons compilation ¹⁰

“The best startup ideas often come from a personal pain point where you realize the status quo is fundamentally broken for the consumer.” — Spencer Rascoff, lessons compilation ¹⁰

“Arrived makes investing in a rental home accessible to anyone with $100 and four minutes to spare.” — Spencer Rascoff, on why he invested in Arrived Homes, Built In Seattle, June 2021 ¹⁵

“The banking system can’t be reimagined solely by the people that are already in it.” — Spencer Rascoff, on joining the Varo Bank board, PR Newswire, April 2022 ⁹

“I am honored to step into the CEO role at such a pivotal time for Match Group.” — Spencer Rascoff, on his appointment as Match Group CEO, PR Newswire, February 2025 ³

“Throw everything overboard that you don’t really need.” — Spencer Rascoff, advice to founders during downturns, dot.LA, LA Tech Week ²²

What Founders Say

Colin Walsh, CEO of Varo Bank, stated upon Rascoff joining the board: “Spencer joins us during a crucial period of growth for the bank and the digital banking industry” ⁹.

Jeff Iloulian, CEO of HostGPO, said of the $6M round that included 75 & Sunny: “What makes this funding round truly special is that our investors wholeheartedly align with our values and share our vision of helping hosts scale their businesses while elevating industry standards” ¹⁶.

Austin Allison, CEO and co-founder of Pacaso, has described working with Rascoff at Zillow — where Allison’s company Dotloop was acquired — as formative to their later partnership co-founding Pacaso ²³.

No additional independently sourced founder testimonials found beyond the above statements. The quotes from Walsh and Iloulian are from company press releases rather than independent reviews of Rascoff as an investor.

Connections

• CEO, Match Group (February 2025–present) — board member since March 2024 ³⁴
• Board member, Palantir Technologies (NYSE: PLTR) ³⁴
• Board member, Varo Bank (April 2022–present) ⁹
• Former board member, TripAdvisor (Nasdaq: TRIP) ³⁴
• Former board member, Zulily (Nasdaq: ZU) ³⁴
• Co-founder and Chairman, Pacaso — alongside CEO Austin Allison (former Dotloop founder) ¹²³
• Co-chairman, Supernova Partners — SPAC vehicles that took Offerpad and Rigetti Computing public ⁷⁸
• Board of Trustees, Harvard-Westlake School ⁴
• CNBC contributor and host of “Office Hours with Spencer Rascoff” podcast ¹¹⁰

Sources