This profile has not been claimed and data may not be accurate.
21st percentile
71st percentile
Co-founder of TaskRabbit and Grouparoo, both acquired, now investing via Edgewater Capital
Credibility
Portfolio Scale · 70th percentile
- Named as a general partner on Edgewater Capital Partners V, LP (a pooled investment fund) per SEC Form D filing.
- Partner or principal at Edgewater Capital Partners, a private investment fund, per SEC Form D records.
Relationship Matrix
Founder score
- 92%Probability of being accurate (92%)Past co-founder of TaskRabbit and Grouparoo.
- 90%Probability of being accurate (90%)Both TaskRabbit and Grouparoo had co-founders alongside Brian Leonard.
- 88%Probability of being accurate (88%)Two founded companies were acquired: TaskRabbit by IKEA and Grouparoo by Airbyte, both at undisclosed prices.
- 72%Probability of being accurate (72%)Raised approximately $40.7M total across TaskRabbit ($37.7M) and Grouparoo ($3M seed).
- 45%Probability of being accurate (45%)Identified Stack Overflow account for Brian Leonard with 11 reputation.
- 40%Probability of being accurate (40%)Identified Hugging Face account @brianleonard.
Investor score
- 22%Probability of being accurate (22%)Named as a general partner on Edgewater Capital Partners V, LP (a pooled investment fund) per SEC Form D filing.
- 22%Probability of being accurate (22%)Partner or principal at Edgewater Capital Partners, a private investment fund, per SEC Form D records.
What you likely need
You're a two-exit technical founder with deep AI and data infrastructure credibility, currently in a rare window to be intentional about what comes next. The highest-value Festival events for you are small, high-trust dinners and roundtables where you can pressure-test a new founding thesis, formalize your angel activity, and build the public technical reputation that attracts co-founders and early users. You'll get the most out of gatherings that put you in the room with other repeat founders, AI infrastructure builders, and YC-network operators who can accelerate your next move without burning your energy.
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.
- positioningA repeat-founder dinner for technical co-founders who have built and exited data or AI infrastructure companies, to pressure-test a new founding thesis in the AI tooling space
- introsA YC alumni roundtable for two-plus-exit founders formalizing their angel practice, to share deal flow and co-invest in early-stage AI and data infrastructure startups
- tacticalAn open-source AI tooling happy hour for founders and engineers building in the data connector and context-management space, where you can demo your OSS work and attract early co-founders or users
- positioningA small positioning dinner for technical founders who have navigated open-source GTM and acquisition exits, to workshop public narratives about the Grouparoo-to-Airbyte journey for the data infrastructure community
- introsA YC Demo Day mentor office-hours session pairing two-exit founders with current AI-batch teams, leveraging your TaskRabbit and Grouparoo track record to give high-signal feedback and build warm relationships with the next generation of data founders
- hiringA dinner for Series A and B AI startup CEOs actively searching for a CTO or VP Engineering, where your TaskRabbit CTO tenure and Airbyte director experience make you the most credible person in the room
- wellbeingAn intimate roundtable for repeat founders between companies — people who have done 10-plus years of back-to-back founding and operator roles — to share honest frameworks for pacing, selectivity, and avoiding the trap of rushing the next commitment
- fundraisingAn angel syndicate happy hour for technical founders writing checks into AI and data infrastructure, to formalize deal-sharing relationships with other credible operator-angels from the Airbyte and YC ecosystem