Miles Grimshaw

Miles Grimshaw
Occupation	Venture capitalist
Employer	Thrive Capital
Known for	General partner at Benchmark and Thrive Capital
Education	Yale University

Miles Grimshaw is an American venture capitalist who has worked as a general partner at two of the most prominent venture capital firms in the technology industry: Thrive Capital and Benchmark. Born around 1991, Grimshaw first gained attention in the venture capital world as a young investor at Thrive Capital, the New York–based firm founded by Joshua Kushner. In late 2020, at the age of 29, he became the most recent general partner added to Benchmark's partnership, one of the youngest investors to hold that title at the storied Sand Hill Road firm. During his tenure at Benchmark, Grimshaw became known for his investments in enterprise software and artificial intelligence companies, including notable bets on Airtable, Benchling, and others. In March 2024, in a move that attracted significant industry attention, Grimshaw departed Benchmark to rejoin Thrive Capital, completing a rare "boomerang" in the venture capital industry.

Education

Grimshaw attended Yale University, where he completed his undergraduate studies. Details of his specific field of study and graduation year have not been widely reported, though based on his reported age of 29 at the time of his Benchmark appointment in late 2020, he would have been part of a graduating class in the early-to-mid 2010s.

Career

Early career at Thrive Capital

Before joining Benchmark, Grimshaw worked at Thrive Capital, the New York–based venture capital firm founded by Joshua Kushner. Thrive Capital has been known for its investments in technology companies across consumer internet, software, and other sectors. During his initial tenure at Thrive, Grimshaw developed a track record as an investor in enterprise and software companies. His work at Thrive included investments in companies such as Airtable, a cloud-based collaboration platform; Supergreat, a beauty community app; and Benchling, a cloud platform for life sciences research and development.

Grimshaw's time at Thrive Capital established him as a rising figure in the venture capital industry, building experience and a portfolio that would attract the attention of Benchmark's partnership.

Benchmark (2020–2024)

In December 2020, Benchmark announced that it had added Grimshaw as its fifth general partner, making him the most recent addition to the firm's small and selective partnership. At the time of the announcement, Grimshaw was 29 years old, underscoring the firm's willingness to bring in younger talent. Benchmark is known for operating with one of the smallest partnerships among major venture firms, historically maintaining a roster of roughly five general partners who share equally in the economics of the fund, a distinctive structural feature in the industry.

Grimshaw's addition to Benchmark was significant in part because the firm is selective about new partners and had not added a general partner in some time before his arrival. His hiring reflected Benchmark's strategy of recruiting investors with strong existing track records and relationships in the technology ecosystem.

During his time at Benchmark, Grimshaw focused on investments in enterprise software and emerging technology sectors. By mid-2023, he had become a prominent voice within the firm on matters related to artificial intelligence, a topic of surging interest across the venture capital and technology industries. In a June 2023 interview with TechCrunch, Grimshaw discussed Benchmark's perspective on the AI landscape, addressing how the firm was evaluating opportunities in a rapidly evolving market. His willingness to engage publicly on AI investment strategy reflected the degree to which artificial intelligence had become a central focus for venture capital firms by 2023.

In a September 2021 profile in Fortune, Grimshaw discussed his investment philosophy, including the concept that companies sometimes need to "fire" their customers — a reference to the strategic discipline of focusing on the right customer segments rather than pursuing growth indiscriminately. This perspective reflected a broader approach to enterprise software investing that prioritized product-market fit and sustainable business models over raw growth metrics.

Grimshaw's tenure at Benchmark lasted approximately three and a half years. During this period, the firm continued to operate its distinctive equal-partnership model and maintained its position as one of the most prominent early-stage venture capital firms in Silicon Valley.

Return to Thrive Capital (2024–present)

On March 5, 2024, it was reported that Grimshaw was leaving Benchmark to rejoin Thrive Capital, the firm where he had begun his venture career. The move was described as unexpected and attracted significant coverage in technology and venture capital media. The Information characterized the transition as "another VC boomerang," situating it within a broader trend of investors returning to firms where they had previously worked.

The departure was notable for several reasons. Benchmark is considered one of the most prestigious venture capital firms in the industry, and general partnerships there are rare and coveted positions. Leaving such a role voluntarily was an unusual move that prompted speculation and discussion within the venture capital community.

Grimshaw's return to Thrive Capital came as the firm was expanding its scale and ambitions. By mid-2025, Thrive Capital had raised a $10 billion fund, a significant milestone that underscored the firm's growth trajectory since its founding. The substantial fund size indicated that Thrive had evolved considerably from the time of Grimshaw's initial tenure, giving him a platform to deploy capital at a larger scale than during his earlier years at the firm.

A subsequent analysis by technology journalist Eric Newcomer in August 2025, examining the strategic trajectories of major venture firms, referenced the competitive dynamics between Benchmark and Thrive Capital, placing Grimshaw's move in the broader context of how different partnership models and investment strategies were performing in the evolving venture landscape.

Investment focus and philosophy

Throughout his career, Grimshaw has focused primarily on enterprise software and technology platform investments. His portfolio has included companies such as Airtable, a collaborative work management platform; Benchling, which provides cloud-based software for life sciences research and development; and Supergreat, a beauty-focused social platform.

Grimshaw's interest in artificial intelligence as an investment category became a defining element of his public profile, particularly during his time at Benchmark. In his 2023 interview with TechCrunch, he engaged with questions about how AI was reshaping the technology landscape and how venture capital firms were positioning themselves to evaluate AI-related opportunities.

His investment philosophy, as articulated in the 2021 Fortune profile, emphasized the importance of customer selectivity and strategic focus in building enterprise software companies. The concept of "firing your customer" that he discussed reflected an approach to company building that prioritized depth of product-market fit over breadth of adoption in early stages.

Recognition

Grimshaw's appointment as a general partner at Benchmark at the age of 29 was itself a marker of recognition within the venture capital industry, given the firm's stature and the selectivity of its partnership. His career trajectory — moving from Thrive Capital to Benchmark and back to Thrive — has been covered by major technology and business publications including TechCrunch, Fortune, The Information, and Newcomer, reflecting his prominence within the venture capital community.

His public commentary on artificial intelligence investment strategy in 2023 positioned him as one of the venture capital voices engaged with what became one of the defining technology trends of the 2020s.