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Pilot Group

North America, Florida, United States, Sarasota

Description

Pilot Group is a distinctive private investment firm established by media luminary Bob Pittman, widely recognized as a co-founder of MTV and former COO of AOL. Based in the United States, the firm distinguishes itself through a "non-traditional" approach to investing, primarily targeting companies within the dynamic media and consumer-retail sectors. Pilot Group's strategy centers on identifying and nurturing businesses with the potential to emerge as dominant category leaders, leveraging Pittman's extensive experience and network in these industries.

The firm operates with a long-term investment horizon, emphasizing close collaboration with the management teams of its portfolio companies to drive substantial value creation. Unlike conventional venture capital funds that might adhere strictly to specific funding stages, Pilot Group's flexible structure allows it to engage across various growth phases, from significant growth equity rounds to strategic investments. This adaptability reflects its non-traditional ethos, enabling it to pursue unique opportunities that align with its vision of fostering market-defining enterprises.

Pilot Group boasts a robust portfolio of successful ventures, underscoring its expertise in identifying high-potential companies. Notable past and present investments include Zipcar, the pioneering car-sharing service acquired for approximately $500 million, and Thrillist, a digital media and e-commerce company that raised an $18 million Series D round with Pilot Group's participation. More recently, the firm has invested in high-growth companies such as Vroom, an online used car retailer that secured a $250 million Series F round, and Daily Harvest, a subscription service for healthy food, which raised a $43 million Series B round. These investments highlight Pilot Group's capacity to participate in substantial funding rounds, typically committing capital to companies that have achieved significant traction and are poised for accelerated expansion.

Investor Profile

Pilot Group has backed more than 20 startups, with 0 new investments in the last 12 months alone. The firm has led 3 rounds, about 15% of its total and boasts 7 exits across its portfolio.

Investment Focus Highlights

  • Concentrates on Series B, Series A, Seed rounds (top funding stages).
  • Majority of deals are located in United States, Ireland.
  • Strong thematic focus on Mobile, Advertising, Email Marketing.
  • Typical check size: $5M – $25M.

Stage Focus

  • Series B (30%)
  • Series A (30%)
  • Seed (20%)
  • Series D (5%)
  • Angel (5%)
  • Series Unknown (5%)
  • Private Equity (5%)

Country Focus

  • United States (95%)
  • Ireland (5%)

Industry Focus

  • Mobile
  • Advertising
  • Email Marketing
  • Analytics
  • E-commerce
  • Predictive Analytics
  • Publishing
  • Gaming
  • Internet
  • News
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FAQ

Frequently Asked Questions

Learn who this investor regularly partners with—both firms and angels—and explore their latest activity.

Who does Pilot Group frequently co-invest with?

General Catalyst
North America, Massachusetts, United States, Cambridge
Co-Investments: 3
Headline
North America, California, United States, San Francisco
Co-Investments: 1
Founder Collective
North America, Massachusetts, United States, Cambridge
Co-Investments: 1
AV
North America, New York, United States, New York
Co-Investments: 3
Gotham Ventures
North America, New York, United States, New York
Co-Investments: 2
DFJ Growth
North America, California, United States, Menlo Park
Co-Investments: 1
Lerer Hippeau
North America, New York, United States, New York
Co-Investments: 4
Intel Capital
North America, California, United States, Santa Clara
Co-Investments: 1
RRE Ventures
North America, New York, United States, New York
Co-Investments: 4
Founders Fund
North America, California, United States, San Francisco
Co-Investments: 3

Which angels does Pilot Group often collaborate with?

JS
North America, New York, United States, Brooklyn
Shared Deals: 1
AR
North America, New York, United States, New York
Shared Deals: 2
ML
North America, New York, United States, New York
Shared Deals: 2
RC
North America, California, United States, San Francisco
Shared Deals: 1
RH
North America, California, United States, San Francisco
Shared Deals: 1
PH
North America, Vermont, United States, Dorset
Shared Deals: 1
BT
North America, California, United States, San Francisco
Shared Deals: 1
ML
North America, California, United States, San Francisco
Shared Deals: 1
JJ
North America, California, United States, San Francisco
Shared Deals: 1
JG
North America, New York, United States, New York
Shared Deals: 1

What are some of recent deals done by Pilot Group?

PureWow

New York, New York, United States

PureWow is a digital media company that specializes in women's lifestyle content, covering fashion, beauty, tech, recipes, health & more.

Digital MediaFashionLifestyle
SeedMay 5, 2015
Amount Raised: $2,500,000
Appy Couple

New York, New York, United States

Appy Couple enables users to create and publish personal mobile wedding apps and websites to share details and photos.

EventsMobile AppsWedding
SeedNov 7, 2013
Amount Raised: $1,500,000
Sailthru

New York, New York, United States

Sailthru helps modern marketers acquire, grow, and retain customers.

AdvertisingAnalyticsDigital MarketingE-CommerceEmail MarketingEnterprise SoftwareMarketing AutomationMobilePredictive AnalyticsPublishing
Series ASep 1, 2011
Amount Raised: $8,000,000
Business Insider

New York, New York, United States

Business Insider is an online platform that offers the latest business, celebrity, and technology news.

Digital MediaNewsPublishing
Series DJul 28, 2010
Amount Raised: $3,000,000
Sailthru

New York, New York, United States

Sailthru helps modern marketers acquire, grow, and retain customers.

AdvertisingAnalyticsDigital MarketingE-CommerceEmail MarketingEnterprise SoftwareMarketing AutomationMobilePredictive AnalyticsPublishing
SeedJul 26, 2010
Amount Raised: $1,000,000
Betaworks

New York, New York, United States

Betaworks Ventures is a product-focused, seed-stage venture capital fund.

Angel InvestmentCoworkingSocial Media
Series BMar 11, 2010
Amount Raised: $20,000,000
Vital Juice Newsletter

New York, New York, United States

Vital Juice is a daily email newsletter for women that delivers the latest information on fitness, nutrition, beauty and wellness.

E-CommerceFitnessHealth CareLifestyleNewsNutritionWellness
Private EquityJan 29, 2009
Project Playlist

Palo Alto, California, United States

Commercial-free Internet Radio Service

ConsumerInternetMachine LearningMedia and EntertainmentMessagingMobileMusicMusic Streaming
Series BNov 10, 2008
Amount Raised: $20,000,000
NextRoll

Dublin, Dublin, Ireland

NextRoll is a marketing technology company that employs machine learning to provide businesses with strategic ways to reach buyers.

Ad RetargetingAdvertisingEmail MarketingMachine LearningMarketingPredictive AnalyticsSaaSSoftware
Series ASep 16, 2008
Amount Raised: $4,000,000
Proclivity Media

New York, New York, United States

Proclivity Systems develops a central revenue optimization platform empowering targeted marketing and merchandising programs.

AdvertisingAnalyticsMarketingRetail
Series BSep 1, 2008
Amount Raised: $5,200,000