Ben Gilbert
Co-Founder and Managing Director @ Pioneer Square Labs
Seattle, United States
Ben Gilbert is a seed investor at Pioneer Square Labs in Seattle focused on Travel and Tourism. Ben Gilbert is the Co-Founder and Managing Director at Pioneer Square Labs, Co-Host at Acquired.FM, and a Board of Directors at TrovaTrip. He previously worked as the Co-Founder and Madrona Venture Labs at Madrona Venture Group, Head of The Garage at Microsoft, and the Co-Founder of Red Ride and Functional Delights. Ben attended the Ohio StateUniversity.
- Total investments:
- 5
- Last investment:
- Lead investor:
- 60%
Last updated:
For AI agents: llms.txt
Industries Ben Gilbert invests in
Stages Ben Gilbert invests in
Countries Ben Gilbert invests in
Contacts
| Type | Contact | Validation |
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| Work email | ||
| Personal email | ||
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Investment Focus
Industry
- Travel 1 (20%)
- Tourism 1 (20%)
- Software 1 (20%)
- Wellness 1 (20%)
- Biometrics 1 (20%)
Stage
- Seed 2 (40%)
- Series A 2 (40%)
- Pre-Seed 1 (20%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
TrovaTrip
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TrovaTrip is an audience monetization platform for creators, entrepreneurs, and businesses. Hosts use their platform to easily plan and sell group trips, offer paid or donation-based livestreams, and sell digital products like ebooks and recorded workshops. | $15M / Series A / Sep 20, 2022 | |
Tin Can
|
Far Homes makes to find, buy and manage homes abroad. | $2.3M / Seed / Sep 13, 2022 | |
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Tin Can
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Far Homes makes to find, buy and manage homes abroad. | $2.3M / Pre-Seed / Sep 13, 2022 | |
Levels
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Levels develops a health and wellness platform designed to monitor metabolic fitness. The platform tracks blood glucose in real-time, enabling users to optimize their diet and exercise. The company was founded in 2019 and is a remote-first company. | $38M / Series A / Apr 20, 2022 | |
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TrovaTrip
|
TrovaTrip is an audience monetization platform for creators, entrepreneurs, and businesses. Hosts use their platform to easily plan and sell group trips, offer paid or donation-based livestreams, and sell digital products like ebooks and recorded workshops. | $5M / Seed / Aug 17, 2021 |
Co-Investors
About Pioneer Square Labs
Pioneer Square Labs is a studio that creates and launches technology startups. They provide market research, concept validation, engineering, data science, visual, UX design, and product management services. They also provide recruiting, fundraising, marketing, company formation, finance, operations, legal, and HR services.
Pioneer Square Labs Contacts
| Name | Phone | Socials | |
|---|---|---|---|
Ansel Santosa
Senior Software Engineer
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Ben Gilbert
Co-Founder and Managing Director
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David Zager
Partner and CDO
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Greg Gottesman
Co-Founder & Managing Director
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Julie Sandler
Co-Founder, General Partner, and Managing Director
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FAQ
What does Ben Gilbert invest in?
Ben Gilbert invests primarily in Travel, Tourism and Software startups, most often at Seed and Series A stage. Most of the 5 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
How do I contact Ben Gilbert?
Public channels for Ben Gilbert include LinkedIn, X (Twitter) and the website linked on this profile. For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.
When did Ben Gilbert last invest?
The most recent investment recorded for Ben Gilbert closed in Sep 2022. Shizune tracks 5 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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