John Pepper
About John Pepper
John Pepper is a Boston-based entrepreneur and angel investor. Tracxn dates his start in the startup ecosystem to 1996 with Boloco, which it lists as the company he founded. NFX Signal describes him as a former founder and CEO and the Managing Partner of 040 Capital.
He is based in Boston and New England. NFX lists his investing interest as hospitality and workforce-focused tech.
PitchBook says he has been an angel investor since 2014, with investments in more than 20 startups in consumer and consumer tech. The companies it names include Kigo Kitchen, Dunwello, Spindrift, Botanica Seattle, Dos Toros (now part of Chopt), Clover Food Lab, York Athletics, Botkeeper, OpenCity, HigherMe and College Pulse.
Tracxn records a March 2019 Series A investment in MarginEdge. In a LinkedIn post, Pepper described himself as an angel investor in Athletic Brewing Co.
Public databases list only a few of his deals, so their counts are partial.
Lounge's deals desk lists two BrandRank.AI seed entries with his name: BRANDRANK.AI Seed $5.1M and BrandRank.AI Seed $3M, both dated 2026-07. Crunchbase shows him as an investor in the BRANDRANK.AI seed round. That round lists QCA Ventures and Grit Capital Partners as lead investors. Crunchbase describes the company as AI search visibility and brand monitoring software, based in Cincinnati.
PitchBook also lists Loop AI (dated 2026-02-02) and Rownd among his investments.
His public record is mostly seed-stage and early-stage angel deals. The sectors are consumer products, food and beverage, hospitality, workforce tech and HR tech, with recent additions in applied AI and marketing software. Tracxn lists his investment geography as the United States. I found no public statement of his check size or investment thesis.
- BrandRank.AI: AI search visibility and brand monitoring software; seed round, July 2026 on the Lounge deals desk.
- Loop AI: business software company; PitchBook dates the investment to February 2026.
- Rownd: listed by PitchBook among his investments; year not public.
- MarginEdge: Series A investment, March 2019, per Tracxn.
- Athletic Brewing Co.: he describes himself as an angel investor; year not stated.
- Spindrift, Clover Food Lab, Dos Toros, Botkeeper and College Pulse: consumer and consumer tech investments named by PitchBook; years not given.
- pitchbook.com/profiles/investor/224380-63
- signal.nfx.com/investors/john-pepper_1
- crunchbase.com/funding_round/brandrank-ai-seed--e8ff3f07
- crunchbase.com/organization/brandrank-ai/profiles_and_contacts
- tracxn.com/d/people/john-pepper/__g94WtiRdnetakycgSOdypFts4fFlZvrVENU-
- tracxn.com/d/people/john-pepper/__HRUmaPS-uIbUh6oy-e5Sgw1xcnPB_0PT5puP
- linkedin.com/posts/johnspepper_winning-by-losing-activity-690375677030
Investing activity
John Pepper appears in 2 AI deals tracked by the Lounge deals desk. The rounds are mostly Seed, with a median round size of $5M. The most recent are BrandRank.AI (Seed, $3M, Jul 2026) and BRANDRANK.AI (Seed, $5.1M, Jul 2026).
John Pepper most often invests alongside QCA Ventures, Grit Capital Partners, John Costello and Chris Hood, and the companies they back on Lounge are mostly in AI.
Deals
Frequently asked questions about John Pepper
Does John Pepper invest in AI startups?
Yes. The Lounge deals desk shows two BrandRank.AI seed entries in July 2026. PitchBook also lists Loop AI and Rownd.
What stage does John Pepper invest in?
His known deals are early-stage angel investments, including seed rounds and one Series A in MarginEdge in 2019.
What is John Pepper's check size?
His check size is not public. The BrandRank.AI amounts on the deals desk are round totals, not his own checks.
What sectors does John Pepper back?
His public portfolio covers consumer and consumer tech, food and beverage, hospitality, workforce and HR tech, and now AI software for marketing and brand visibility.
Where is John Pepper based?
NFX Signal lists him in Boston and New England.
How can founders reach John Pepper?
His LinkedIn profile is the only public contact route I could confirm. I found no personal site or X account.
Is John Pepper an angel investor?
Yes. John Pepper invests personally as an angel.
What AI companies has John Pepper invested in?
John Pepper's AI investments include BrandRank.AI and BRANDRANK.AI. The 2 rounds on Lounge are listed on this page with amounts, dates and co-investors.
What stage does John Pepper invest at?
In the rounds tracked on Lounge, John Pepper has invested at Seed, with a median round of $5M.
Who does John Pepper co-invest with?
John Pepper's most frequent co-investors on Lounge are QCA Ventures (2 deals), Grit Capital Partners (2 deals), John Costello (2 deals), Chris Hood (2 deals) and Tech Square Ventures (1 deal).