Benjamin Gilbert Pioneer

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Benjamin Gilbert Pioneer (Acquired.FM)

Benjamin Gilbert, a co-founder of Pioneer Square Labs (PSL), is a prominent figure in the startup ecosystem known for promoting innovative ideas through his venture capital firm and startup accelerator. PSL, based in Seattle, is dedicated to transforming nascent concepts into fully-fledged companies, providing the essential support and resources needed for early-stage startups to thrive.

Benjamin Gilbert role at PSL involves overseeing the entire process of startup creation, from ideation and validation to scaling and securing additional funding. Under his leadership, PSL has incubated and launched numerous successful startups across various industries, leveraging a unique model that combines venture capital investment with hands-on strategic support. His approach is highly collaborative, working closely with entrepreneurs to refine their business models and accelerate their growth.

Before co-founding Pioneer Square Labs, Benjamin Gilbert had a rich background in entrepreneurship and venture capital. His experiences include founding several startups himself, which provided him with firsthand insights into the challenges and opportunities that new companies face. This experience is invaluable in his current role, where he not only evaluates the potential of new ideas but also mentors founders through the intricate process of building a business.

Benjamin Gilbert is particularly interested in technology-driven startups that have the potential to disrupt traditional industries. His vision for PSL is to create a vibrant ecosystem where innovative ideas can flourish, supported by the expertise and resources of the accelerator. He is also active in the broader venture capital community, frequently participating in forums and panels to share his knowledge and insights on entrepreneurship and innovation.

Beyond his work at PSL, Benjamin Gilbert is committed to fostering a supportive environment for entrepreneurship in Seattle and beyond. He is involved in various community initiatives aimed at promoting innovation and supporting emerging entrepreneurs, particularly those from underrepresented backgrounds. Looking forward, Benjamin aims to expand the reach of Pioneer Square Labs, exploring new markets and continuing to innovate how startups are built and launched.

Benjamin Gilbert’s work at Pioneer Square Labs epitomizes his commitment to nurturing startup talent and his belief in the transformative power of innovation. His leadership not only drives the success of the startups he works with but also contributes significantly to the vibrancy of the startup ecosystem in Seattle and beyond.

Seattle, Washington, United States

Los Angeles, California, U.S.
Ben Gilbert
NameBen Gilbert
Date of BirthN/A
Birth PlaceSeattle, Washington, United States
University The Ohio State University
ProfessionFounder & CEO
EducationBS in Computer Science 

Early Life

Benjamin Gilbert is a pivotal figure in the tech and entrepreneurship realm, serving as both the co-host and co-founder of the widely acclaimed Acquired podcast. With its immersive three-hour episodes, Acquired delves into the compelling narratives and strategic maneuvers of successful companies, boasting a massive following of over half a million listeners. Garnering the prestigious title of the #1 Technology show on Apple Podcasts and Spotify underscores the podcast’s profound impact.

Before carving his niche in podcasting, Benjamin Gilbert embarked on a dynamic journey that saw him as a co-founder and managing director at Pioneer Square Labs, a prominent venture fund and startup studio headquartered in Seattle. Presently, he continues to contribute as a venture partner, leveraging his wealth of experience and expertise.

Benjamin Gilbert’s entrepreneurial odyssey commenced with his foray into independent iPhone development, birthing the popular productivity app “SeizeTheDay,” embraced by millions worldwide. His tenure at Microsoft further honed his acumen, marked notably by spearheading the launch of Office for iPad and spearheading The Garage, a pioneering grassroots innovation initiative within the tech giant.

Recognition swiftly followed Benjamin Gilbert’s trailblazing path, earning him accolades such as the 2017 Young Entrepreneur of the Year by GeekWire and inclusion in the illustrious 40 Under 40 roster by Puget Sound Business Journal. His stellar achievements are rooted in a robust academic foundation, holding a BS in Computer Science and Engineering from The Ohio State University, where his passion for technology and business burgeoned.

Benjamin Gilbert’s formative years were marked by an insatiable curiosity for technology and entrepreneurship, catalyzed by the tech boom of his upbringing. His early ventures and projects not only underscored his ingenuity but also imparted invaluable lessons in leadership and customer-centricity.

Guided by mentors and buoyed by familial support, Benjamin’s journey epitomizes the symbiosis of passion and proficiency. His adeptness in coding, product development, and market analysis crystallized through hands-on experiences, laying the bedrock for his pivotal role in shaping the landscape of innovation.

As Benjamin Gilbert continues to champion innovation at Pioneer Square Labs, his indelible imprint on the tech ecosystem underscores his unwavering commitment to propelling nascent startups toward stratospheric success.


Benjamin Gilbert’s career trajectory is marked by his deep involvement in entrepreneurship and innovation, particularly within the technology sector. His journey from a tech-savvy student to a co-founder of Pioneer Square Labs (PSL) highlights his commitment to fostering innovation and supporting early-stage startups. After completing his education, Benjamin Gilbert began his career in technology and business development roles within established companies. This provided him with valuable industry experience and a deeper understanding of how large businesses operate, manage product development, and respond to market demands. However, his passion for entrepreneurship soon led him to venture into more independent projects. Benjamin’s transition from employee to entrepreneur involved co-founding several tech startups. Through these ventures, he learned crucial lessons in building teams, attracting investment, and scaling business operations. Each startup venture added to his expertise and reputation in the startup community, laying the groundwork for his later initiatives.

Co-founding Pioneer Square Labs:

Identifying a gap in the support system available to startups, Benjamin, along with partners, founded Pioneer Square Labs, a startup studio and venture capital firm. PSL was designed to innovate the process of startup creation by actively co-building companies, providing them with initial capital, strategic advice, and operational support. Under his leadership, PSL has successfully incubated and launched numerous startups, many of which have gone on to achieve significant growth and market presence.

Role at Pioneer Square Labs:

At PSL, Benjamin Gilbert’s role encompasses a wide range of activities. He is deeply involved in the ideation and validation phases of new ventures, leveraging his experience to assess the viability of new ideas. He also plays a crucial role in mentoring founders, drawing on his own experiences to guide them through the complex landscape of tech entrepreneurship.

Community Involvement and Thought Leadership:

Beyond his operational responsibilities, Benjamin Gilbert is an active participant in the broader entrepreneurial ecosystem. He speaks at industry conferences, contributes to educational initiatives, and writes about the challenges and opportunities in the startup world, positioning himself as a thought leader in entrepreneurship and venture capital.

Benjamin Gilbert’s career is a testament to his dedication to innovation and his belief in the transformative power of technology and entrepreneurship. His work not only impacts the companies he helps create but also contributes to advancing the startup ecosystem as a whole.

Personal Life

Benjamin Gilbert’s personal life is characterized by a commitment to balance and a strong connection to community and family, which complement and enrich his dynamic professional life. Benjamin places great importance on his relationships with family and friends. He often credits his family’s support as a pivotal element in his success, providing him with the encouragement and stability needed to pursue his entrepreneurial ambitions. He ensures to spend quality time with his family, recognizing that maintaining these personal connections is crucial for his overall well-being. Deeply invested in his local community, Benjamin actively participates in community service and outreach programs. He is particularly passionate about educational initiatives that provide technology access and training to underprivileged youth. His involvement extends to mentoring young entrepreneurs, offering guidance and support to help them navigate the complexities of starting and running a business.

Hobbies and Interests:

Outside of his professional endeavors, Benjamin has a variety of interests that keep him refreshed and inspired. He is an avid reader, particularly enjoying books on leadership, innovation, and history, which provide him with broader perspectives and new ideas. Additionally, Benjamin is enthusiastic about outdoor activities; he enjoys hiking and cycling, finding these activities therapeutic and a way to disconnect from the demands of his work life.

Health and Wellness:

Understanding the pressures of his career, Benjamin is committed to maintaining his health through regular exercise and mindfulness practices. He incorporates routines such as yoga and meditation into his daily life to manage stress and maintain mental clarity.


Travel is another significant aspect of Benjamin’s life, providing him with the opportunity to relax and rejuvenate, while also offering inspiration for his work. He values the exposure to different cultures and business practices that travel brings, enriching his understanding and approach to his ventures.

Benjamin Gilbert’s personal life reflects a well-rounded individual who values connectivity, health, and continuous learning. These aspects not only nurture his personal development but also enhance his effectiveness and leadership in the professional arena.


Benjamin Gilbert, as a co-founder of Pioneer Square Labs (PSL) and a notable figure in the startup ecosystem, has been instrumental in launching and supporting various innovative projects across multiple sectors. His initiatives range from incubating tech startups at PSL, advising on AI-driven analytics platforms, to investing in green technology and supporting educational technology expansion. Notably, he also co-founded a healthcare innovation hub aimed at improving patient care through technological advancements. These projects highlight his diverse interests and his commitment to using technology to solve real-world problems.

Through his roles as a co-founder, advisor, investor, and mentor, Benjamin has significantly contributed to shaping the technology landscape, fostering new businesses, and driving innovation in artificial intelligence, sustainability, education, and healthcare. His efforts reflect a deep commitment to not only advancing technological and business practices but also addressing societal challenges through innovative solutions. This diverse project portfolio underscores his holistic approach to entrepreneurship and his influence in the tech startup community.


Project TitleRoleYearDescription
Startup Studio LaunchCo-founder2015Initiated Pioneer Square Labs as a startup studio and VC firm, focusing on incubating and launching tech startups.
AI-Driven Analytics PlatformAdvisor2017Supported the development of a platform that utilizes AI to provide real-time analytics for businesses.
Green Tech InitiativeInvestor2019Invested in and supported a project aimed at developing sustainable technology solutions for environmental challenges.
EdTech Expansion ProjectMentor2020Guided a startup specializing in educational technology to expand its reach and impact on global education.
Healthcare Innovation HubCo-founder2021Co-launched a hub that collaborates with tech innovators to create healthcare solutions that improve patient care and system efficiency.


These projects represent a range of sectors including artificial intelligence, green technology, education, and healthcare, reflecting Benjamin’s broad interests and his commitment to leveraging technology for societal benefits. His roles vary from being a co-founder and investor to acting as an advisor and mentor, demonstrating his versatile involvement in the tech ecosystem. Each project underscores his vision of using innovative approaches to address pressing challenges and enhance industry practices.




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