Raymond Tonsing

Founder & Managing Partner at Caffeinated Capital

📍 San Francisco, California, United States🔄 Updated September 2026💼 22 investments📅 17 years investing🗓 Last invested Apr 2025𝕏 @upgrade_to_unlock
Operator-angel🌍 United States20+ investments
22
Total investments
16
Early stage
2
Mid stage
0
Late stage
17y
Years active

Portfolio

21 investments · sorted by recency
All investments
Early stage
Mid stage
Late stage
Investor & Board Member
Apr 2025
We apply world-class software engineering to a warfighting domain of persistent conflict. Our mission is to deliver industrial-scale cyber capabilities, ensuring the U.S. and its allies are able to deter and defeat their adversaries. At Twenty, we own the mission end to end, from rapid R&D to operational deployment. We’re looking for the rare builders who thrive under pressure, move fast, and create revolutionary capabilities that change how nations project industrial-scale power in cyberspace. Backed by the top defense tech investors in the business, including Caffeinated Capital, General Catalyst, and In-Q-Tel, we are the top 0.1% of cyber operators and proven builders building 100X cyber capabilities for the United States of America.
Investor & Board Member
Jul 2023
Saronic is building cutting-edge unmanned surface vehicles that enable maritime security and domain awareness by combining best-in-class hardware, software and artificial intelligence into one scalable, fully integrated platform.
Investor & Board Member
Sep 2021
The operating system for modern command. With Onebrief, leaders can enable a superhuman command: one that makes brilliant decisions, scales output, and is optimally efficient. Currently live on NIPR, SIPR, and JWICS. Learn more at onebrief.com
Investor
Mar 2021
The business planning platform for finance and beyond.
Investor & Board Observer
Dec 2020
Varda is building the infrastructure for a thriving orbital economy, from in-orbit pharmaceutical processing to reliable and economical reentry capsules. From new, life-saving pharmaceuticals to more powerful fiber optic cables, there is a world of products used to benefit life on Earth that can only be manufactured in space. Our mission is to expand the economic bounds of humankind.
Investor
May 2019
Aven is reinventing consumer credit. Our mission is to provide the lowest-cost, most transparent, and most convenient access to capital. We use technology to unlock the wealth in your assets and give you credit for what you already own. Our first product is the world’s lowest APR credit card, backed by home equity. Using multiple patented technologies, we’ve reduced a process that typically takes 4–6 weeks and thousands of dollars down to as fast as 15 minutes and $0 to get. Since launching in 2019, Aven cardholders have saved over $200M. We’re proud to maintain a 4.9-star rating on Trustpilot across 5,000+ reviews. Were backed by leading investors including Founders Fund, Khosla Ventures, Sequoia Capital, Caffeinated Capital, General Catalyst, NYCA, and Max Levchin. The team features leaders from top financial services and fintech companies—such as Goldman Sachs, Capital One, Square—as well as technology companies such as Meta, Microsoft, Google, Uber, and Tesla. Aven has been recognized on the Forbes Fintech 50 and the GGV Capital Fintech Innovation 50. And we’re just getting started.
Investor
Mar 2019
Playground combines AI research and product design to invent new kinds of creative tools.
Investor
Mar 2017
Boom Supersonic is redefining commercial flight by bringing supersonic flight back to the skies with Overture. This historic commercial airliner is designed and committed to industry-leading standards of speed, safety, and sustainability. Boom’s vision is to bring families, businesses, and cultures closer together through supersonic travel and make the world dramatically more accessible. Founded in 2014, Boom has assembled a team of over 150 full-time employees who have made contributions to over 220 air and spacecraft programs. For more information, please visit https://boomsupersonic.com.
Investor
Mar 2017
Clipboard Health connects healthcare facilities with local professionals who can work unfilled shifts. Patients get improved care, and nurses get more flexibility and higher pay. Nurses can compare work details and pay rates (or negotiate for more) in an open, transparent marketplace. Today, healthcare facilities are understaffed, which can result in poor patient care, regulatory penalties, and employee burnout. Meanwhile, local nurses have time and want to pick up extra shifts. These two parties don’t know each other and aren’t sure if they can work together (licenses, qualifications, or even trust might get in the way). Clipboard Health exists to solve this problem.
Investor
Apr 2015
Pioneering diabetes reversal for 100 million people, and setting a new standard of medical care for people living type 2 diabetes, prediabetes, or obesity. Just a few short years ago, type 2 diabetes reversal wasn’t considered possible. Fast forward to today, and Virta’s pioneering efforts have made it mainstream, while revolutionizing healthcare delivery in the process. Still, there’s so much more to be done! If you’re ready to redefine what’s possible, transform our industry, and reinvent healthcare for good, we invite you to join our cause at Virta! We have opportunities for software engineers, health coaches, scientists, clinicians, and more. Visit https://www.virtahealth.com/careers to see our full list of open roles. See how Virta is transforming healthcare by developing the next generation of healthcare technology. Check out our technical blog at https://www.virtahealth.com/health-tech. Join our Talent Community at https://jobs.ashbyhq.com/virtahealth/form/talent-community-form to stay connected!
Investor & Board Observer
Sep 2014
TrueAccord is the leader in digital collections. By focusing on great user experiences, TrueAccord provides businesses with superior debt collection results. Our machine learning platform adapts to consumer behavior with personalized and empathetic communications to deliver the right payment option at the right time and channel. We work with top financial institutions, enterprise companies and upcoming businesses to recover billions in lost revenue. For more information, visit www.trueaccord.com.
Investor
Jun 2014
Founded in 2014, Opendoor’s mission is to power life’s progress one move at a time. The traditional real estate process is broken and our goal is simple: fix it. We are building a digital, end-to-end customer experience that makes buying and selling a home simple, certain, and fast. We have assembled a dedicated team with diverse backgrounds to support more than 250,000 customer transactions across 50 markets in the U.S. But the work is far from over. Transforming the real estate industry takes tenacity and dedication. It takes problem solvers and builders. It takes a tight-knit community of teammates doing the best work of their lives, pushing one another to transform a complicated process into a simple one. So where do you fit in? Whether you’re passionate about real estate, people, numbers, words, code, or strategy -- we have a place for you. For more information, please visit www.opendoor.com Keep up with latest Opendoor news and reports: https://linktr.ee/opendoorhq
early stageReal Estate
Investor & Board Observer
May 2014
Integrate your systems. Simplify business processes. Triple productivity. Sapho Employee Experience Portal enables IT teams to deliver powerful, personalized experiences that today's workforce expects on any device, intranet, or messenger. At Sapho, we believe that when employees are armed with better software experiences, their potential is unlimited. Our investors have seen our customers'​ success and are believers too. Our employees are based in our headquarters in the San Francisco Bay Area and in Prague, Czech Republic. We are currently looking for talented people who are passionate about their craft, curious about how things work, and love the idea of working in an intellectually honest environment where the best idea wins. Think you would be a good fit? Email your resume to careers@sapho.com Website: https://www.sapho.com/ Blog: http://blog.sapho.com/ Facebook: https://www.facebook.com/saphoapp/ Twitter: https://twitter.com/sapho
Investor
Feb 2014
Color Health provides the infrastructure to support durable and equitable public health across entire populations. Color’s technology and clinical services are the backbone of large-scale population health programs for over 200 institutions worldwide, with data and services spanning hereditary cancers, heart disease, infectious disease testing (including COVID-19), and community-based vaccination programs. Using a data driven approach, we’re democratizing access to health care insights.
early stagePublic Health
Investor & Board Observer
Apr 2013
Airtable’s AI app platform is the easiest way to build custom apps that accelerate your business operations. Turn your data into AI apps, automations, and agents with our AI app builder and AI agent software — no code or technical expertise required. Your teams can move from idea to impact in minutes. Introducing Superagent: superagent.com More than 500,000 organizations, including 80% of the Fortune 100, use Airtable to manage marketing campaigns, optimize product management, and streamline any workflow. The result? Faster innovation, better customer experiences, enterprise-grade governance, and a modern way to work across teams. We’re hiring! Visit airtable.com/careers to learn more.
Show all 21 investments ↓
Experience · 27 entries
All (27)
Investments (22)
Founder (2)
Board (7)
2025
Investor & Board Member
Apr 2025
We apply world-class software engineering to a warfighting domain of persistent conflict. Our mission is to deliver industrial-scale cyber capabilities, ensuring the U.S. and its allies are able to deter and defeat their adversaries. At Twenty, we own the mission end to end, from rapid R&D to operational deployment. We’re looking for the rare builders who thrive under pressure, move fast, and create revolutionary capabilities that change how nations project industrial-scale power in cyberspace. Backed by the top defense tech investors in the business, including Caffeinated Capital, General Catalyst, and In-Q-Tel, we are the top 0.1% of cyber operators and proven builders building 100X cyber capabilities for the United States of America.
2023
Investor & Board Member
Jul 2023
Saronic is building cutting-edge unmanned surface vehicles that enable maritime security and domain awareness by combining best-in-class hardware, software and artificial intelligence into one scalable, fully integrated platform.
2021
Investor & Board Member
Sep 2021
The operating system for modern command. With Onebrief, leaders can enable a superhuman command: one that makes brilliant decisions, scales output, and is optimally efficient. Currently live on NIPR, SIPR, and JWICS. Learn more at onebrief.com
Investor
Mar 2021
The business planning platform for finance and beyond.
2020
Investor & Board Observer
Dec 2020
Varda is building the infrastructure for a thriving orbital economy, from in-orbit pharmaceutical processing to reliable and economical reentry capsules. From new, life-saving pharmaceuticals to more powerful fiber optic cables, there is a world of products used to benefit life on Earth that can only be manufactured in space. Our mission is to expand the economic bounds of humankind.
Show all 27 entries ↓
Investment activity
2009–2025 · 22 investments
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