𝐒𝐞𝐥𝐥𝐢𝐧𝐠 𝐢𝐧 𝐭𝐡𝐞 𝐀𝐠𝐞 𝐨𝐟 𝐀𝐈
Thank you to Reggie Marable, Chief Customer Officer at @Sierraplatform, for recently joining us for a sharp fireside chat on how enterprise selling is changing.
Three takeaways we're still thinking about:
1. Earn trust with proof, not promises. Low-commitment entry points and outcome-based pricing make it easy to say yes to something small - then prove your way to a bigger relationship.
2. Engineer credibility early. Respected design partners, founders in the room with early customers, and security and compliance handled head-on build confidence before you have scale.
3. AI accelerates, but people close. The stack is a multiplier for research, prep, and pipeline - but in-person relationship building still closes big enterprise deals
#AI #FutureOfWork #EnterpriseSales
Atlanta showed up, the founders delivered, and Open Pitch 2026 ended with two champions. 🏆🏆
From hundreds of startups → 4 finalists → 2 winners, each receiving a $125,000 investment prize. 🚀
🏆 Groundwork Health: an Atlanta-based, AI-powered platform helping healthcare organizations deploy and manage community health workers.
🏆 Path Intelligence: an AI-powered spatial intelligence and buyer engagement platform for the real estate industry.
Congratulations to our winners and welcome to the Open Opportunity Fund family! 🎉
And congrats to fellow finalists Greens Health and Facecard for an incredible showing.
Thank you to our judges @MasterPmiller, La La Anthony, Angela Simmons and @pauljudge, our partners @Earnyourleisure and Invest Fest, @millingstroy, Rashad Bilal, and our host Kendra G.
📍 Atlanta | August 9, 2026
Presented by @Earnyourleisure + Open Opportunity Fund
We’re excited to announce the four finalists selected for Open Pitch 2026 🚀
• Face Card
• Greens Health
• Groundwork Health
• Path Intelligence
Open Pitch (@theopenpitch) is part of Open Opportunity Fund’s pre-seed sourcing strategy and our continued effort to identify exceptional founders building the next generation of AI-native and agentic technology companies.
Tomorrow, these four teams will pitch live at Invest Fest in Atlanta for a $125,000 investment from Open Opportunity Fund.
4 finalists. 1 stage. 1 winner. $125K on the line. 🏆
📍 Georgia World Congress Center
🗓 Sunday, August 9
⏰ 1:15 PM
🎤 Presented by @EarnYourLeisure + Open Opportunity Fund
Congratulations to each of the finalists. We look forward to learning more about their companies and seeing them on stage.
#OpenOpportunityFund #OpenPitch #InvestFest2026
OutRival (@outrivalAI ) launches The New Normal. A new show featuring the operators who actually deployed AI — not the founders pitching it.
Episode 1 features Kermit Cook, CEO of Penn Foster Group, on reinventing a 135-year-old company for the AI era. Hosted by @rubenharris, Timur Meyster, and John Henry.
Penn Foster now graduates 93,000+ learners a year — behind only NYC and LA. 🎓
Watch the first episode here: https://t.co/vQ2FNlkwx0
#AI #FutureOfWork #EdTech
1/ Today Outrival is launching: The New Normal.
A new video show co-hosted by our CEO @rubenharris, Co-Founder & President @timurmeyster, and Head of Insurance @JohnHenryStyle.
Featuring the leaders actually deploying AI in production. Not the vendors. Not the pundits.
https://t.co/8zQqz5nG7L
Full YouTube Episode Here: https://t.co/wAy38TtAte
repost: @forbes At the Forbes Self-Made 250 Celebration, @pauljudge, managing partner of Open Opportunity Fund and a serial entrepreneur, told Forbes senior editor Alex Knapp that a deeper understanding of any industry will become more valuable as artificial intelligence transforms how companies are built.
Photo: Jamel Toppin for Forbes
#Forbes250
Honored to join @esferabr during Brazil Week with Wesley Batista, André Esteves, @DonaldJTrumpJr, @RealOmeedMalik.
75% of Brazilians use AI at work. Higher than the US or Europe. Yet global AI companies have barely started operating there. This gap is where the next decade of value will be built. 🇧🇷🇺🇸
Coworked is bringing agentic AI to one of the most capacity-constrained functions inside the enterprise: project management.
We’re thrilled to announce our co-lead investment in Coworked’s $1.8M Round.
"Agentic AI has the ability to fill critical talent gaps by adding AI workers into an enterprise. Project management is one of the clearest examples of where this shift will happen: work that has historically required human coordination, follow-through, and judgment can now be done by AI agents. Coworked's team brings the subject matter expertise in enterprise project management to understand the workflows and organizational dynamics needed to build a solution that works inside large organizations,” said Paul Judge.
We’re proud to partner with the Coworked team as they build the future of enterprise project execution.
Learn more: https://t.co/ITVbmb5iOP
Thank you to the National Association of Investment Companies (NAIC) for spotlighting Open Opportunity Fund and our mission to invest where traditional venture capital often isn’t looking.
At Open Opportunity Fund, we believe some of the most compelling opportunities are being built by overlooked founders in emerging tech hubs and across business-critical software categories shaping the next decade of innovation.
Read the full feature from NAIC here: https://t.co/V6VkoDy9Vd
“Developers are changing how they build, and AI is becoming a more natural interface for how they build software. They now expect to interact with APIs more dynamically and move from idea to production much faster. By bringing Finix into tools like ChatGPT, Claude and Gemini, we’re aligning with that shift and making it easier to go from a question about payments to building on our platform.”
- @RSerna2010 , CEO and co-founder of @finix
A timely look at how payments infrastructure is adapting to the way developers build today.
Learn more: https://t.co/ttjlYEOvj1
Thank you to the Power100 presented by Blueprint Capital Advisors for recognizing @pauljudge and @ShakaRasheed as part of the 2026 Power100 Asset Managers honorees.
This list highlights leaders across venture capital, advisory platforms, fund-of-funds, and institutional investment organizations who play a critical role in the investment ecosystem by sourcing managers, conducting rigorous diligence, and deploying capital with discipline and conviction. Their leadership helps shape the next generation of investment firms and market-defining companies. We are honored to see both Paul and Shaka recognized among this year’s group and proud to be part of a broader community helping shape the future of venture capital.
We’re looking forward to attending the Power100 event in LA on May 4th. Thank you to Blueprint and the Power100 family for organizing this. Congrats to all of our peers recognized in the list.
For more important, visit https://t.co/eivufY5DKt.
📣 Deadline Extended: Apply by April 20 at 11:59 PM ET.
We’ve extended the application deadline for Open Pitch, our startup competition at Open Opportunity Fund, presented live at Invest Fest 2026.
As part of our commitment to backing exceptional early-stage founders, Open Pitch is designed to spotlight bold entrepreneurs building the next generation of AI and agentic companies. From finance and healthcare to cybersecurity, marketing, logistics, education, and beyond, we’re looking for founders using AI to reshape what’s possible.
The winning company will receive a $125,000 investment prize. Five finalists will pitch live on stage at Invest Fest 2026 in Atlanta, gaining national exposure, investor access, and the opportunity to share their vision in front of thousands.
📅 New deadline: April 20 at 11:59 PM ET
📍 Live at Invest Fest (Atlanta) | August 7-9, 2026
🎤 Presented by @EarnYourLeisure + Open Opportunity Fund
🔗 Apply now at https://t.co/XRusw6nuP0
🚀 Congratulations to our portfolio company @eightsleep and founders @m_franceschetti and @a_zatarain on their recent $50M financing at a $1.5B valuation.
Eight Sleep has built a category-defining platform at the intersection of health, longevity, and applied AI, using real-time physiological signals to deliver personalized sleep optimization at scale.
“What we’re building doesn’t exist yet — a system that understands your body better each night and acts on that knowledge. Our goal is to build the defining health technology company of this generation.” - Matteo Franceschetti, co-founder and CEO of Eight Sleep.
We are proud to have invested in 2021 and to have witnessed the team’s exceptional execution and long-term vision.
Today we're announcing a new round of funding that values @eightsleep at $1.5 billion, led by @tether Investments.
Ten years ago I started Eight Sleep with one conviction: the night is the most underutilized lever in human health. Almost nobody was engineering their sleep.
Last year, we hit free cash flow positivity, launched 3 new products, expanded to 34 countries, and published peer-reviewed studies showing the Pod reduces menopausal hot flashes by 56% and restores the body's natural circadian temperature rhythm during sleep, lowering core body temperature and improving cardiovascular recovery. A product you sleep on is producing clinical outcomes that rival pharmaceutical interventions.
We're now building a predictive AI agent trained on 1B+ hours of sleep data. It anticipates your night before it happens.
And we're advancing FDA filings for sleep apnea detection. Passive. Every night. No wires, no clinic visits.
The night is just the beginning.
We’re excited to bring @TheOpenPitch back for 2026. As part of Open Opportunity Fund’s pre-seed sourcing strategy and our ongoing focus on identifying exceptional entrepreneurs early, Open Pitch is designed to expand our reach and surface high-potential founders building the next generation of AI-native and agentic tech companies.
Artificial intelligence is rewriting the rules across every industry, from finance to healthcare, cybersecurity to sales & marketing, logistics to education. If you’re building in this space, we welcome you to apply. The winning company will receive a $125,000 investment from Open Opportunity Fund, with finalists pitching live on stage at Invest Fest in Atlanta (August 7-9, 2026) in partnership with @EarnYourLeisure .
Applications are now open at https://t.co/JMDLl9Og0x and close April 10 at 11:59 PM ET. Founders are invited to apply today.
Paul Judge was named to the @Forbes 250, Forbes’ list of America’s Greatest Innovators.
As described by Forbes, “To kick off our yearlong series of special reports celebrating America’s 250th birthday, we present the men and women who best embody that creative spirit. All of them are in the mold of the quintessential American innovator, Thomas Edison. That means they aren’t just inventors; they’re business leaders who bring their breakthroughs to market, transforming entire industries and creating new ones.”
We’re honored to see @pauljudge included among tech leaders like Jensen Huang, Sam Altman, and Marc Benioff, as well as investors like Vinod Khosla, Marc Andreessen, and Ray Dalio.
We’re excited to announce our investment in Furl’s $10M Seed Round.
Furl is tackling one of cybersecurity’s biggest gaps: turning vulnerability findings into real fixes. By applying agentic AI to security remediation, Furl helps teams safely execute remediation at scale.
“Cybersecurity has become very good at telling teams what’s wrong, but fixing those problems is still painfully manual,” said Derek Abdine, CEO and Co-Founder of Furl. “Having built inside vulnerability management and endpoint tooling, we saw how remediation breaks down in practice. Furl applies agentic AI where it actually matters - executing fixes safely, with context - so teams can reduce risk instead of just reporting on it.”
“Agentic AI is changing how organizations can scale and solve complex problems. We’re excited to invest in Furl as they bring agentic AI to security remediation to help businesses keep up with and stay ahead of the growing volume of cybersecurity attacks,” said @pauljudge.
We’re proud to partner with the Furl team as they redefine what’s possible in security remediation.
Learn more: https://t.co/i9PD5A7WOv
🎉We’re thrilled to congratulate our partners at @paystand on the acquisition of Bitwage, expanding their B2B payments ecosystem through stable-coin and global currency rails.
Here’s to powering the future of payments—faster settlements, lower costs, and seamless global reach. 🚀
Learn more: https://t.co/uxG7YIzW9X
Honored to join the @FIIKSA in Riyadh alongside incredible leaders like @aballoughani, @AlkassarEyad, @Ibrahim_Almojel, Abdulaziz Alomran and Ahmed Youssef, discussing “How Saudi Family Offices Spot Unicorns.”
I’ve been fortunate to experience the full journey of building, scaling, and investing in companies around the world. And I truly believe there’s no reason why we can’t see a global number-one company emerge from this region. The talent, ambition, and digital readiness are all here. Historically, capital flowed out of the region, but today, we’re seeing a shift: capital staying in to empower local entrepreneurs and transform legacy companies through technology and AI.
It’s an exciting moment to witness and be part of this transformation. The opportunities ahead are massive — and it’s just the beginning. 🌍🚀 #FII9
Excited to kick off my Middle East trip this week, starting today in Doha, Qatar 🇶🇦! Next up: Riyadh, Saudi Arabia 🇸🇦; Kuwait City, Kuwait 🇰🇼; and Abu Dhabi & Dubai in the UAE 🇦🇪.
Looking forward to deep dives with regional leaders on the practical applications of AI to turbocharge our businesses and drive innovation. Let's shape the future! 🚀