Founder Festival: Ralph Gootee's Profile

Welcome, Ralph Gootee

This profile has not been claimed and data may not be accurate.

Founder108

52nd percentile

Investor38

78th percentile

Combined146

#108 on Leaderboard

YC W12Serial FounderAcquired2 ExitsRaised $75M+100+ EmployeesAngel Investor

Founder Matrix

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Credibility

this founder typical founder (50th pct)

Traction · 58th percentile

Raised approximately $75.1M in total across PlanGrid (at least $40M per SEC Form D) and TigerEye ($35.1M).
Exit: PlanGrid acquired by Autodesk for $875M.
Exit: TigerEye was acquired (listed as Acquired on Y Combinator's company page).

Founder score

98%Exit: PlanGrid acquired by Autodesk for $875M.
97%Y Combinator W12 alum via PlanGrid.
97%Past co-founder of PlanGrid and TigerEye.
92%PlanGrid was co-founded with Tracy Young and Ryan Sutton-Gee.
90%GitHub account @ralphleon is dormant: no public push activity in over 12 years (last push to repo 'TeaTimer' was 4,637 days ago).
85%GitHub account @ralphleon confirmed as Ralph Gootee's account.
85%GitHub account @ralphleon has been active for approximately 16 years (created July 2009).
82%Raised approximately $75.1M in total across PlanGrid (at least $40M per SEC Form D) and TigerEye ($35.1M).
72%Exit: TigerEye was acquired (listed as Acquired on Y Combinator's company page).
60%Stack Overflow account identified for Ralph Gootee.

Investor score

90%Served as Visiting Partner at Y Combinator (W20 batch), coaching over 400 companies on technical evaluation and fundraising strategy.
80%Publicly identified as an angel investor with confirmed investments in multiple early-stage startups.
80%Made at least 3 confirmed angel investments: Prequel, Inboxbooster, and Rayon.
72%Approximately 5 years of investing experience, beginning with his Visiting Partner role at Y Combinator in 2020.

What you likely need

Ralph is a high-credibility serial founder with two exits — including the landmark $875M PlanGrid acquisition — and deep technical leadership now deployed at Lennar as CTO. His investor footprint is modest relative to his founder reputation, suggesting he could formalize his angel activity into a more structured vehicle. Updating his public GitHub presence and technical writing would reinforce his builder brand for the next chapter.

Are these your current priorities?

We will tune and customize your Founder Festival experience to make sure you get invited to the events that would be most valuable to you.

fundraisingFormalize your angel investments into a named syndicate or micro-fund to attract co-investors and increase deal flow beyond the 3 known investments.
positioningPublish a detailed post-mortem or founder story on TigerEye's acquisition to cement your serial-founder narrative and attract future co-founders and investors.
tacticalPush at least one public project to GitHub — your account has been dormant for 12+ years, which undercuts your builder credibility despite your strong engineering track record.
positioningLeverage your CTO role at Lennar to publicly champion proptech innovation, positioning yourself as the bridge between construction software (PlanGrid) and residential real estate at scale.
introsTap your YC W12 alumni network and your Visiting Partner relationships to source deal flow for angel investments in construction-tech and proptech startups.
positioningStart a technical blog or newsletter on building large-scale construction software systems — your Pixar, PlanGrid, and Lennar experience is rare and highly marketable to engineering leaders.
introsPursue board observer or advisory seats at 2–3 early-stage construction-tech startups to convert your domain expertise into structured equity upside beyond angel checks.