Chaifetz Group
Family officeChicago · Seed–Late Stage · 1 people tracked
Investment thesis
Chaifetz Group invests permanent family capital behind entrepreneurs, business owners and management teams aiming to build and grow industry-disrupting businesses. The firm takes a flexible, enduring approach spanning venture capital, private equity, real estate and opportunistic strategies, with a stated focus on creating lasting value over the long term. Led by Dr. Richard A. Chaifetz, the firm draws on an entrepreneurial track record of building companies rather than adhering to a single asset class or fixed time horizon.
Source: firm website, verified Aug 3, 2026.
Team · 1 people
from the firm's websiteWhat they invest in
from 13 of 32 portfolio companiesConsumer ×3HR Tech ×3Mobility & Transportation ×3SaaS ×3Sports Tech ×3AI & Machine Learning ×2Hardware ×2Marketplaces ×2
HQs:United States×11
Who they back
founder profiles across 8 portfolio companiesFounding team size:solo founder×52 founders×23 founders×1
Investments · 32 tracked
founders shown can be your intro path
BETA Technologies develops electric aircraft (including the ALIA eVTOL) and associated charging infrastructure for sustainable aviation.
CleantechDefense TechHardwareMobility & TransportationBurlington, US
Kyle Clark(CEO)Sean Donovan(Executive Officer)Herman Cueto(Executive Officer)
BoardCharles Davis(Director)Mike Stone(Director)Francesco Capretti(Director)
PartnerRichard A. Chaifetz· solo GP
Co-investorsStone PointPreston-Werner VenturesUP PartnersVermont Center for Emerging Technologies (VCET)
15Five provides a strategic performance management platform that helps businesses track employee engagement, performance, and retention through tools like performance reviews, goal tracking, and AI-powered manager coaching.
AI & Machine LearningHR TechSaaSSan Francisco, US
David Hassell(Executive Officer, Director)Shane Metcalf(Director)inNazar Ivaniv
BoardBrent Hill(Director)inMatthew Cowan(Director)in
PartnerRichard A. Chaifetz· solo GP
Co-investors500 GlobalConnetic VenturesConvergeEdison PartnersGray Line PartnersGutbrain Ventures+9 more
PartnerRichard A. Chaifetz· solo GP
PartnerRichard A. Chaifetz· solo GP
aXiomatic is an esports and gaming investment company that provides capital and industry expertise to gaming and digital entertainment companies.
GamingMedia & EntertainmentLos Angeles, US
Peter Guber(Co-Executive Chairman)Victor Goossens(Founder & Co-CEO)Steve Arhancet(Co-CEO)Bruce Stein(Executive Officer, Director)
BoardJeff Vinik(Co-Executive Chairman)Ted Leonsis(Co-Executive Chairman)in
PartnerRichard A. Chaifetz· solo GP
Co-investorsDeclaration PartnersNext Legacy PartnersDreamit VenturesRevolution
Backlot Cars is a wholesale vehicle marketplace that provides high-quality engine recordings with AI-generated issue detection for dealer vehicles, helping wholesale buyers source inventory across various age, condition, and price points.
AI & Machine LearningB2B MarketplacesMobility & Transportation
Justin Davis(Founder)inFabricio SolanesJosh ParsonsRyan Davis
PartnerRichard A. Chaifetz· solo GP
Co-investors500 GlobalKCRise FundOrigin VenturesRevolutionRoyal Street Ventures Management Company, LlcSazze+4 more
PartnerRichard A. Chaifetz· solo GP
Marketplace enabling users to request personalized video messages or live chats with celebrities and influencers.
Steven Galanis(Co-founder)inMartin Blencowe(Founder)inDevon Spinnler Townsend(Co-founder)in
PartnerRichard A. Chaifetz· solo GP
Co-investorsChicago VenturesCleo CapitalConnect VenturesDigi VenturesDuke Capital PartnersEQUIAM+14 more
PartnerRichard A. Chaifetz· solo GP
PartnerRichard A. Chaifetz· solo GP
ComPsych provides organizational mental health, well-being, resilience, and absence/leave management programs for employers worldwide.
HR TechMental HealthWellness & Fitness
PartnerRichard A. Chaifetz· solo GP
PartnerRichard A. Chaifetz· solo GP
Professional drone racing league whose pilots fly identical custom-built FPV drones on 3D courses broadcast worldwide.
New York, US
Nicholas Horbaczewski(Executive Officer, Director)
PartnerRichard A. Chaifetz· solo GP
Co-investorsCerity Partners VenturesLux CapitalRSE VenturesCRCM VenturesDimension CapitalHearst Ventures
DUPR is a rating platform for pickleball players that calculates and updates player ratings on a 2.000–8.000 scale based on match and tournament results submitted by players or clubs.
ConsumerSaaSSports Tech
PartnerRichard A. Chaifetz· solo GP
PartnerRichard A. Chaifetz· solo GP
Fooda operates a marketplace that brings restaurant partners and popup dining experiences directly to workplaces, allowing employees to access fresh meals from high-rated restaurants without leaving their office location.
FoodTechHR TechMarketplacesChicago, US
Orazio Buzza(Executive Officer, Director)Jason Stulberg(Executive Officer)Alex Groesbeck(Executive Officer)Maddy.perseghin Maddy.perseghin
BoardJonathan K. Shulkin(Director)Susan S. Hassan(Director)
PartnerRichard A. Chaifetz· solo GP
Co-investors500 GlobalFull In PartnersLightbankMultiplier CapitalValor Equity Partners
M1 is a technology company offering brokerage services, advisory products, savings accounts, personal loans, and cryptocurrency trading to individual investors.
Fintech
PartnerRichard A. Chaifetz· solo GP
Co-investorsAMK Investment OfficeChicago VenturesClocktower VenturesLeft Lane CapitalStarting LineToba Capital
ParkWhiz is an online parking marketplace and mobile app that lets drivers search, compare prices, and reserve parking spaces in advance for events or immediate use.
ConsumerMarketplacesMobility & TransportationChicago, US
Aashish Dalal(Director)Yona Shtern(Executive Officer, Director)Mike Sands(Director)Sachin Chitnis(Director)Adam Erlebacher(Director)Henry Feinberg(Director)
PartnerRichard A. Chaifetz· solo GP
Co-investorsConnetic VenturesEscalate Capital PartnersVillage GlobalWonder VenturesBaird Venture Partners
PartnerRichard A. Chaifetz· solo GP
PICKLETILE is a racquet sports infrastructure company that designs, manufactures, and builds pickleball facilities through a single design-build model, centered on PICKLEGLASS, an acoustic-rated structural glass enclosure system that replaces chain-link fencing to reduce court noise.
Construction TechHardwarePropTech
PartnerRichard A. Chaifetz· solo GP
PartnerRichard A. Chaifetz· solo GP
AI to understand the world around us
PartnerRichard A. Chaifetz· solo GP
Co-investorsThe Venture Collective
PartnerRichard A. Chaifetz· solo GP
PartnerRichard A. Chaifetz· solo GP
PartnerRichard A. Chaifetz· solo GP
PartnerRichard A. Chaifetz· solo GP
The St.
Media & EntertainmentSports TechSt. Louis, US
PartnerRichard A. Chaifetz· solo GP
PartnerRichard A. Chaifetz· solo GP
The Picklr operates pickleball clubs offering memberships with unlimited play, leagues, tournaments, clinics, guest access, and court reservations across nationwide locations.
ConsumerSports TechWellness & Fitness
PartnerRichard A. Chaifetz· solo GP
TimeDoc Health provides tech-enabled care management services and software for healthcare organizations, medical groups, and practices, covering chronic care management, remote patient monitoring, and behavioral health monitoring.
Digital HealthHealthtechSaaSChicago, US
William Boeglin(Executive Officer, Director)Chris Knoff(Executive Officer, Director)
BoardTim Streit(Executive Officer, Director)in
PartnerRichard A. Chaifetz· solo GP
Co-investorsBreak Trail VenturesGrand VenturesSerra VenturesVocap PartnersAldrichImpact Engine+1 more
PartnerRichard A. Chaifetz· solo GP
PartnerRichard A. Chaifetz· solo GP
Exits · 1
IPOs and acquisitions across the tracked portfolioBeta TechnologiesNYSE: BETA
Portfolio news
latest coverage across their companiesThe Picklr · nasdaqprivatemarket.com · Apr 3, 2026
Drone Racing League · businessplan-templates.com · Feb 3, 2026
Frequently asked questions
- How many investments has Chaifetz Group made?
- Chaifetz Group has 32 tracked investments.
- What stage does Chaifetz Group invest at?
- Chaifetz Group invests at the Seed, Late Stage stages.
- What sectors does Chaifetz Group focus on?
- Chaifetz Group focuses on Sector Agnostic.
- Where is Chaifetz Group located?
- Chaifetz Group is headquartered in Chicago, US.
- Who does Chaifetz Group co-invest with?
- Chaifetz Group most often shares deals with 500 Global, Chicago Ventures, Origin Ventures, among 49 tracked co-investors.
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