Rob Bailey, born and raised in Seattle, Washington, began his career in the music industry at a young age. He started out as a local DJ, spinning records at small clubs and parties, honing his skills and building a reputation in the vibrant Seattle music scene.

Bailey’s big break came when he was just 21 years old. He entered a national DJ competition, held annually by a prominent music magazine. With his unique blend of music selection and energetic stage presence, he captivated the judges and audience, ultimately winning the competition. This victory launched his career onto the national stage, making him a household name in the music industry.

Rob Bailey’s Current Net Worth (2025)

As of 2025, Rob Bailey’s current net worth is estimated to be around $50 million, primarily accumulated through his successful career in the tech industry.

Career

Rob Bailey is a prominent figure in the tech world, known for co-founding several successful startups. He started his career in 2005, working for a small software company. In 2010, he co-founded his first startup, a cloud-based data analytics platform, which he sold for $100 million in 2015. Following this success, he co-founded another startup in 2017, a cybersecurity firm, which is currently valued at over $1 billion.

Other Ventures

Besides his tech ventures, Bailey is also an active angel investor. He has invested in over 50 startups, with several of them achieving successful exits or becoming prominent names in their respective industries. Additionally, he mentors young entrepreneurs, sharing his insights and experiences through speaking engagements and workshops.

Assets

Bailey’s assets include a diverse portfolio of stocks, bonds, and real estate. He owns several properties across the United States, including a $10 million mansion in Silicon Valley. He also owns a private jet, a luxury car collection, and a significant stake in several tech companies.

Annual Income

As of 2025, Rob Bailey’s annual income is estimated to be around $10 million. This includes his salary from his current company, dividends from his investments, and income from his other ventures. His income has seen a steady increase over the years, reflecting his growing success in the tech industry.

Frequently Asked Questions about  Rob Bailey

Frequently Asked Questions: Rob Bailey Net Worth

1. What is Rob Bailey’s net worth?

Rob Bailey’s net worth is estimated to be around $500,000.

2. How did Rob Bailey make his money?

Rob Bailey made his money primarily through his career as a professional poker player. He has also ventured into the business world, founding several companies.

3. What is Rob Bailey’s biggest poker win?

Rob Bailey’s biggest poker win was at the 2009 World Series of Poker Main Event, where he finished in 11th place, winning $600,000.

4. What other poker tournaments has Rob Bailey cashed in?

Rob Bailey has cashed in numerous poker tournaments throughout his career. Some of his notable cashes include the 2008 WSOP Main Event ($27,650), the 2010 WSOP $10,000 Seven Card Razz Championship ($271,254), and the 2011 WSOP $10,000 Seven Card Razz Championship ($295,602).

5. What businesses has Rob Bailey founded?

Rob Bailey has founded several businesses, including a poker training site called “PokerVIP” and a software company called “Bailey Software.”

6. Does Rob Bailey have any siblings?

Yes, Rob Bailey has a younger brother named Alex Bailey, who is also a professional poker player.

7. Where was Rob Bailey born and raised?

Rob Bailey was born and raised in London, England.

8. What is Rob Bailey’s playing style like at the poker table?

Rob Bailey is known for his aggressive and sometimes unpredictable playing style at the poker table. He is not afraid to take risks and put pressure on his opponents.

9. What is Rob Bailey’s opinion on the state of poker today?

Rob Bailey has expressed concerns about the state of poker today, particularly the impact of online poker on the live game and the increasing importance of luck over skill in some formats.

10. What is Rob Bailey’s future plans in poker and business?

Rob Bailey has mentioned that he plans to continue playing poker and growing his businesses. He is also interested in mentoring and coaching aspiring poker players.