Jeffrey Bussgang

Operator · Investor

Co-founder and general partner at Flybridge Capital Partners, and senior lecturer at Harvard Business School (before that, an operator: a cofounder of Upromise and an early employee of Open Market through its IPO). Author of Mastering the VC Game, which introduced the Jungle/Dirt Road/Highway metaphor for startup-stage maturity that MC's Terrain Test builds on.

Known for
Bussgang is known for venture capital writing and for the Jungle, Dirt Road, Highway metaphor for startup stages.
Born
1969

Bussgang has held both seats. He started at The Boston Consulting Group, then joined Open Market as it grew toward its 1996 IPO, then cofounded and ran Upromise (a loyalty-marketing and financial-services firm) as president through its acquisition by Sallie Mae [2]. Only after that operating run did he cofound Flybridge Capital Partners, where he is co-founder and general partner today, and become a senior lecturer at Harvard Business School, where he teaches Launching Technology Ventures [2]. His academic credentials are real but not research credentials: a BA in computer science from Harvard College (magna cum laude) and an MBA from HBS, where he was named a Baker Scholar and a Ford Scholar [3] (HBS’s honor for the top 5 percent of the graduating class by grades) [4]. He has never published peer-reviewed research; his authority comes from having built, then funded, then taught.

HBS recognized that record with its own service honor, the 2021 Robert F. Greenhill Award for Outstanding Service to the HBS Community [5]. Boston’s business press has repeatedly named him among the city’s most influential tech and venture figures, too: Boston Magazine’s “The 100 Most Influential People in Boston Right Now” (2020) and its 21 Most Powerful People in Boston Business (2017), and the Boston Business Journal’s 40 Under 40 (2006) [5]. These are local-prominence markers, not research credentials, and are read that way here.

That sequence is what MC actually cites him for. Bussgang is devoted to startups and venture capital specifically, not management in the abstract; he is not a management theorist or a management researcher, and nothing here should be read as broader authority than that. Within that lane he is credible on three distinct grounds: he ran a company through to acquisition [2], he has worked professionally as a venture capitalist [2], and he teaches the subject to HBS MBAs [2]. His word carries the most weight on the practitioner-facing mechanics of startup-stage transitions (what changes operationally as a company matures) because he has stood on both the operating and the investing side of that transition.

The specific debt is Mastering the VC Game (2010), where Bussgang set out three phases of a startup’s life. In his own words, responding to a reader years later: “I refer to three phases of the startups life: the jungle, the dirt road and the highway.” [1] The jungle is pre-product-market-fit chaos; the dirt road is a clearer but still-bumpy scaling phase; the highway is mature, process-driven execution. Management Craft’s The Terrain Test pairs this terrain layer with Robert Cringely’s Commandos/Infantry/Police people-layer to build a hiring screen for stage fit. The specific thing being cashed on this page is Bussgang’s authorship of the terrain vocabulary, not a general claim to management expertise.

1
Jeff Bussgang, comment on "Scaling the Chasm," Seeing Both Sides, January 15, 2015.
https://seeingbothsides.com/2015/01/13/scaling-the-chasm/
2
Jeff Bussgang, "About," JeffBussgang.com, accessed July 28, 2026.
https://www.jeffbussgang.com/about
3
Jeff Bussgang, instructor profile, General Assembly, archived May 15, 2026.
http://web.archive.org/web/20260515171710/https://generalassemb.ly/instructors/jeff-bussgang/2257
4
"Baker Scholars Gender Gap," The Harvard Crimson, May 27, 2021.
https://www.thecrimson.com/article/2021/5/27/baker-scholars-gender-gap/
5
Jeffrey Bussgang, faculty profile, Harvard Business School, accessed July 28, 2026.
https://www.hbs.edu/faculty/Pages/profile.aspx?facId=108987

Keep learning

The Terrain TestToolA hiring screen for stage fit: has the candidate recently succeeded under the same ambiguity, structure, and support this role will demand?