Chaifetz Group
Family officeChicago · Seed–Late Stage · 1 people tracked
Find your way into Chaifetz Group
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 companiesSports Tech ×4Consumer ×3HR Tech ×3Mobility & Transportation ×3SaaS ×3AI & Machine Learning ×2B2B Marketplaces ×2Hardware ×2
HQs:United States×11
Who they back
founder profiles across 12 portfolio companiesFounding team size:solo founder×42 founders×53 founders×24+ founders×1
Where their founders studiedfrom 15 founders with education data
Duke University ×2Weber State University ×2
What their founders studiedfrom 11 founders with field-of-study data
Finance & Accounting ×4Engineering ×3Business & Management ×2Computer Science ×2
Where their founders worked beforefrom 15 founders with career history
California Black Bears ×2
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)inSean Donovan(Executive Officer)inHerman Cueto(Executive Officer)in
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)
PICKLETILE converts existing tennis and hard courts into pickleball courts with full surface preparation, layout design, and optional glass enclosures and lighting.
Construction TechHardwarePropTechSports Tech
Scott Miller(Founder, CEO)Steven Blustein(Co-Founder, President)in
PartnerRichard A. Chaifetz· solo GP
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)inShane Metcalf(Director)inNazar Ivanivin
BoardBrent Hill(Director)inMatthew Cowan(Director)in
PartnerRichard A. Chaifetz· solo GP
Co-investors500 GlobalBling CapitalConnetic VenturesConvergeEdison PartnersGray Line Partners+10 more
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)in
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 SolanesinJosh ParsonsRyan Davisin
PartnerRichard A. Chaifetz· solo GP
Co-investors500 GlobalKCRise FundOrigin VenturesRevolutionRoyal Street Ventures Management Company, LlcSazze+5 more
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
ComPsych provides mental health, well-being, and absence management services to employers and their employees globally.
Enterprise SoftwareHR TechMental HealthWellness & Fitness
Dr. Richard A. Chaifetz
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
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)inJason Stulberg(Executive Officer)inAlex Groesbeck(Executive Officer)
BoardJonathan K. Shulkin(Director)Susan S. Hassan(Director)William Pescatello(Director)in
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
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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)inJon Thornton(Director)inYona Shtern(Executive Officer, Director)Mike Sands(Director)Sachin Chitnis(Director)Adam Erlebacher(Director)
PartnerRichard A. Chaifetz· solo GP
Co-investorsConnetic VenturesEscalate Capital PartnersVillage GlobalWonder VenturesAlate PartnersAmazon Alexa Fund+3 more
The St.
Media & EntertainmentSports TechSt. Louis, US
BoardRichard ChaifetzRoss Chaifetz
PartnerRichard A. Chaifetz· solo GP
The Picklr operates indoor pickleball facilities and sells franchise locations worldwide.
B2B MarketplacesConsumerSports TechWellness & FitnessUintah, US
Jorge Barragan(Co-Founder & CEO)inAustin Wood(Co-Founder & Chief Visionary Officer)in
PartnerRichard A. Chaifetz· solo GP
TimeDoc Health provides care management services including chronic care management and remote patient monitoring, supported by clinical teams that coordinate patient care.
Digital HealthHealthtechSaaSChicago, US
William Boeglin(Executive Officer, Director)inChris Knoff(Executive Officer, Director)in
BoardTim Streit(Executive Officer, Director)in
PartnerRichard A. Chaifetz· solo GP
Co-investorsBreak Trail VenturesGrand VenturesSerra VenturesVocap PartnersAldrichImpact Engine+1 more
Other
Tracked investments with no reachable website or further public details — typically companies that wound down, renamed, or were absorbed.
Alpine Formula One TeamAnthropicBetiCapsuleCargoCurateFACTOR_PassportPortland Trail BlazersQlooQuipRepurposeSan Francisco GiantsShopThingStack Vulcan PickleballUnited Pickleball AssociationxAI
Exits · 2
1 IPOs · 1 acquisitions · showing 1Beta TechnologiesNYSE: BETA
Portfolio news
latest coverage across their companiesParkWhiz · en.wikipedia.org · Jun 16, 2026
The 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, 2 of which have exited.
- 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, Origin Ventures, Chicago Ventures, among 61 tracked co-investors.
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