Founder Festival: Gordon Wintrob's Profile

Welcome, Gordon Wintrob

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

Founder267

72nd percentile

Investor21

61st percentile

Combined288

#69 on Leaderboard

YC W2014Serial FounderUnicorn FounderAcquired2 ExitsRaised $200M+500+ EmployeesAngel Investor

Founder Matrix

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Credibility

this founder typical founder (50th pct)

Technical Depth · 93th percentile

Currently shipping public code with a push to the 'shitty-wifi' repo 40 days ago.
Active GitHub builder with 32 public repositories.
GitHub account @gwintrob is confirmed as Gordon Wintrob's account.
GitHub account has been active for over 14 years, created in December 2011.

Founder score

99%Current Co-founder and CTO of Newfront, a tech-driven insurance brokerage.
99%Y Combinator alum via StackLead (W2014) and Newfront (W2018).
99%Active GitHub builder with 32 public repositories.
99%GitHub account @gwintrob is confirmed as Gordon Wintrob's account.
99%GitHub account has been active for over 14 years, created in December 2011.
97%Exit: StackLead was acquired by LinkedIn in September 2014.
97%Past founder of StackLead, a sales research company acquired by LinkedIn.
95%Currently shipping public code with a push to the 'shitty-wifi' repo 40 days ago.
95%Exit: Newfront Insurance is being acquired by Willis Towers Watson (WTW) for up to $1.3 billion.
95%Both Newfront and StackLead were co-founded with other founders.
90%Wikidata entity Q137671346 exists for Gordon Wintrob, confirming public notability.
80%Newfront raised $310M in total funding across its funding rounds.

Investor score

82%Publicly identified as an angel investor with a profile on CBInsights and Tracxn.
80%Made at least 3 known angel investments including Ascend, Sensible, and Rillet.
40%Approximately 3 years of investing experience based on known portfolio activity.

What you likely need

Gordon is a high-signal serial founder with two exits — including a $1.3B acquisition of Newfront by WTW — and a strong YC pedigree. With the Newfront acquisition closing, he is likely at an inflection point: deciding whether to start a new company, deepen his angel investing, or take on a senior role at a larger firm. His technical depth (MIT EECS, active GitHub, AI/ML focus) and network position him well for a third founding act.

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.

positioningLeverage your post-acquisition liquidity and YC/Newfront network to identify your next founding opportunity, ideally in AI infrastructure or insurtech where you have deep domain expertise.
fundraisingWith 3+ known investments already, consider formalizing a small angel syndicate or micro-fund to systematize deal flow and increase your investing surface area.
introsEngage actively with the YC alumni network as a Group Partner candidate or batch mentor — your dual-batch experience (W2014 + W2018) and two exits make you an unusually credible voice.
tacticalOpen-source a meaningful internal tool or AI project from your Newfront work to build public technical credibility — your GitHub repos currently have no stars despite 14 years of activity.
positioningPublish more on AI-driven insurance and brokerage transformation — your Newfront blog posts and podcast appearances show strong communication skills that could anchor a broader platform.
wellbeingPost-acquisition transitions can be disorienting even for experienced founders — take intentional time to decompress and clarify your next chapter before committing to a new venture.
introsDeepen your angel portfolio in AI and insurtech startups where your operator expertise gives you a genuine edge in evaluating founders and products.