​The Alpha Play Virtual Event Series

​We’re excited to announce the seventh session in our TAP virtual series, featuring a conversation with Thom Lumpkin, Managing Partner and Founder of Woolly Bear Capital.

• ​Date: Monday, September 8, 2025

• ​Time: 12:00PM–1:00PM Pacific Time

• ​Location: Virtual (link will be sent after registration)

​Woolly Bear Capital focuses on an overlooked corner of venture: the secondary market for startup employee equity. Rather than competing for primary allocations, Woolly Bear acquires shares from departing employees who face difficult liquidity decisions when their options near expiration.

​Thom will share how Woolly Bear sources and evaluates opportunities in companies backed by firms like Sequoia, Accel, and NEA, typically acquiring positions at deep discounts and for shorter holding periods.

​We'll explore:

• ​Why 2/3 of startup option grants are never exercised—and how this creates extraordinary opportunities

• ​The three-pronged advantage: buying at discounts, shortening hold periods, and improving selection

• ​The mechanics of the employee secondary market and deal structuring

• ​Why this overlooked market represents a compelling alternative to traditional venture investing

• ​Key lessons from their Fund I's portfolio construction and investment process

​​Only Accredited Investors will be admitted to the virtual event.