Where does Gregor Watson work?

Gregor Watson is Co-Founder at 1Sharpe Capital and Board director at Lessen.

What check size does Gregor Watson write?

Gregor Watson typically writes checks of $500K – $2M.

Where did Gregor Watson go to school?

Gregor Watson studied at Regis University (BA/BS).

Gregor Watson

Investor

Co-Founder at 1Sharpe Capital · Managing Partner at 1Sharpe Ventures · Board director at Lessen

Oakland, California

Writes $500K – $2M checks · typically $1M

About

Gregor Watson built, scaled and sold a single‑family rental lending platform to Blackstone and—simultaneously a proptech entrepreneur, institutional real estate investor and public SPAC CEO—brings capital markets and public-market expertise.

Contact· self-published, not guessed

g•••@1sharpe.comreveal

Invests in

AI & Machine LearningFintechInsurTechPropTechSaaS

Board director at Lessen

Intro paths

→

In turn, Gregor can intro founders to Lessen's investors below.

Lessen's investors · 7

1Sharpe VenturesPiedmont · $500K – $2M checks 75 & SunnyLos Angeles · $100K – $5M checks Copper Sky CapitalScottsdale · $2M – $4M checks Fifth WallLos Angeles · $250K – $100M checks · since 2023 General CatalystSan Francisco · $30M checks Khosla VenturesMenlo Park · $5K – $50M checks Navitas CapitalCulver City · $100K – $5M checks

Co-founders at Lessen

Jay M.Founder

Experience

Chisel IndustriesCo-Foundercurrent2025 — presentSan Francisco, California, United States
Chisel IndustriesChief Executive Officercurrent2025 — present
UCSF Benioff Children's HospitalsBoard Membercurrent2022 — presentOakland, California, United States
1Sharpe CapitalCo-Foundercurrent2017 — presentPiedmont, ca
1 sharpe + Chisel IndustriesCo-Foundercurrent2016 — present
Roofstock, Inc.Chairman + co-foundercurrent2014 — present
LessenBoard Membercurrent2020 — present
Creative JuiceCo-Founder + Advisor Creative Juice2020 — 2025
ZiboBoard member + Co Founder2018 — 2025
643 Capital ManagementFounder2012 — 2018San Francisco
McKinley PartnersPartner2008 — 2012

Skills & more

Real Estate23Real Estate Economics14Residential Homes15Mergers3Investment Properties10Due Diligence5Real Estate Transactions5Real Estate Development2Property Management2Investments5Valuation3Commercial Real Estate3

+7 more

SellersLoansAcquisitionsInvestorsMergers & AcquisitionsApartmentsManagement

From Gregor's professional profile.

Colleagues at 1Sharpe Capital

Rob Bloemker

General Partner at 1Sharpe Ventures

Network2

Feng Wang

Investor at 1Sharpe Ventures

Ginny Miller

Partner at 1Sharpe Ventures

Investors connected to Gregor in public investor directories — a warm-intro map.

Frequently asked questions

Who is Gregor Watson?: Gregor Watson built, scaled and sold a single‑family rental lending platform to Blackstone and—simultaneously a proptech entrepreneur, institutional real estate investor and public SPAC CEO—brings capital markets and public-market expertise.
Where does Gregor Watson work?: Gregor Watson is Co-Founder at 1Sharpe Capital and Board director at Lessen.
What does Gregor Watson invest in?: Gregor Watson invests in AI & Machine Learning, Fintech, InsurTech, PropTech, SaaS.
What check size does Gregor Watson write?: Gregor Watson typically writes checks of $500K – $2M.
Where did Gregor Watson go to school?: Gregor Watson studied at Regis University (BA/BS).