This profile has not been claimed and data may not be accurate.
51st percentile
69th percentile
Two-time YC founder now CEO of Keep, a VC-backed Canadian fintech
Credibility
Operator · 90th percentile
- Current co-founder and CEO of Keep Technologies, a VC-backed Canadian fintech.
- Y Combinator alum across two batches: CareLedger (S15) and Origin (W17).
- Past founder of CareLedger (YC S15), Origin (YC W17), and Aiddly Health.
- Origin (YC W17) was co-founded with Eric Meadows as co-founder and CTO.
Relationship Matrix
Most Complimentary
Founder score
- 98%Probability of being accurate (98%)Y Combinator alum across two batches: CareLedger (S15) and Origin (W17).
- 97%Probability of being accurate (97%)Current co-founder and CEO of Keep Technologies, a VC-backed Canadian fintech.
- 95%Probability of being accurate (95%)Past founder of CareLedger (YC S15), Origin (YC W17), and Aiddly Health.
- 92%Probability of being accurate (92%)Origin (YC W17) was co-founded with Eric Meadows as co-founder and CTO.
- 85%Probability of being accurate (85%)Keep Technologies and prior companies raised approximately $110.9M in total venture funding.
- 80%Probability of being accurate (80%)Identified as a researcher on OpenAlex with 28 published works and 147 citations.
Investor score
- 75%Probability of being accurate (75%)Publicly identified as an angel investor with a known investment in Takachar.
- 75%Probability of being accurate (75%)Has at least one confirmed active investment (Takachar).
- 50%Probability of being accurate (50%)Approximately 8 years of investing experience, with earliest known investment dating to around 2017.
What you likely need
You'd get the most out of Festival events that put you in front of growth-stage and crossover investors who understand Canadian fintech and can lead or anchor a Series B. You'd also benefit from tight-knit YC founder rooms where you can formalize your angel syndicate, swap operator talent, and pressure-test Keep's SMB banking positioning with peers who've scaled through similar inflection points. Leadership and co-founder alignment sessions would round out your Festival experience as you navigate the 80+ employee scaling threshold.
Would you attend these IRL Festival events?
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.
- fundraisingA Series B founder dinner with growth-stage and crossover investors (Tiger, Ribbit, Bessemer) who've backed Canadian or SMB fintech breakouts, to pressure-test Keep's raise narrative and land warm intros to lead investors
- fundraisingA YC S15/W17 alumni roundtable for repeat founders who've crossed $80M raised, to swap Series B playbooks, benchmark ARR transparency strategies, and identify co-investors for Keep's growth round
- introsA YC founder angel syndicate dinner for S15/W17 alumni actively writing checks, to formalize a co-investment SPV structure, align on deal flow sharing, and build out Oliver's investor brand alongside Keep's scaling story
- positioningA Canadian fintech founder roundtable with operators who've built dominant SMB brands (Shopify alumni, Wave, Clearco) to pressure-test Keep's 'definitive Canadian SMB bank' positioning and identify the sharpest proof points from the Mastercard partnership and 11-country footprint
- tacticalA fintech credit and lending operator dinner with founders and execs who've expanded institutional credit facilities beyond $50M (Brex, Ramp, Capchase alumni), to identify the right lending partners for scaling Keep's SMB credit limits in Canada
- hiringA YC fintech operator happy hour targeting senior engineers and GTM leaders from S15–W20 batches who've scaled payments or banking products past 80 employees, to fill Keep's next-phase leadership hires through warm YC network referrals
- wellbeingA small founder wellbeing dinner for YC-backed co-founding teams navigating the 80–150 employee inflection point, to share leadership structure frameworks, co-founder alignment rituals, and culture preservation tactics ahead of a Series B hiring surge