Chipper Boulas

Raylu continues to lead the pack by working with #Claude and Anthropic to drive alpha for the best private investment firms.

18

🌍 Big Updates from The Venture Studio Forum (VSF): 🚀 We’ve launched our new website: Explore our refreshed home at venturestudioforum.org. 🤘 All Access, No Barriers: We’ve removed all paywalls — every Member now has full access to every benefit. This ensures our ecosystem continues to innovate and mature as a well-understood, sought-after asset class. 🎁 Member Gifts and Sponsorships Launched: We’ve rolled out a range of Sponsorship opportunities to sustain and scale this mission — including a Founding Sponsor option for our current Members (available for a limited time). Want to get involved? I’ll put all the links in the comments! #VentureStudios #Innovation #Ecosystem #VSF

18

1 Comment

**Navigating Talent Transitions: What It Means for the Venture Ecosystem** As we observe talented leaders like Andrew Tulloch transition from Thinking Machines Lab to MetaAI, it prompts an essential question for investors: How do leadership changes influence a startup's trajectory? At ElevenX Capital, we believe that the right leadership is critical to driving innovation and sustainable growth. Monitoring these shifts allows us to better understand potential disruptions or opportunities within our investment portfolio. How do you assess leadership stability in your investment thesis? #investing #innovation #venturecapital #entrepreneurship

1

The FT article of today, “How private equity’s big bet on software was derailed by AI,” is deliberately provocative but rests on a flawed premise. It conflates AI’s growing ability to generate software artefacts with the far more complex reality of delivering enduring enterprise software value. They are not the same. What we are seeing across our portfolios and the wider market is that AI is an accelerant for established software companies, not a destroyer of them. Enterprise software value lies not in the code itself, but in the ecosystem around it; implementation, configuration, training, support, compliance and continuous evolution. These systems are deeply embedded in mission-critical operational processes and customers depend on trusted, long-term partners. AI-generated products alone cannot replicate this operational depth or trust. Equally, domain expertise, proprietary data and embedded workflows create powerful structural moats. While AI may lower the cost of writing code, it does not replicate decades of accumulated operational knowledge, regulatory nuance, or customer integration. Established vendors possess deep customer relationships and real-world data assets that new entrants cannot quickly replicate. In practice, AI is strengthening incumbents. It enables faster development, better automation and improved customer outcomes; benefits that established vendors can immediately deploy across their installed base. Combined with high switching costs, operational dependency and customer trust and data protection requirements, this reinforces rather than weakens their competitive position. Finally, the economic advantage lies with companies that already have recurring revenue and customer access. AI reduces marginal development cost and accelerates innovation, improving margins and strengthening customer retention. In summary, AI lowers the barrier to creating software, but not the far higher barrier to building trusted, deeply embedded enterprise platforms. Far from destroying software value, AI is amplifying the advantages of agile, domain-led, customer-centric software companies. As ever, the clearest perspective comes not from media grabbing headlines, but from customers themselves. That said, we note in our Book, the AI Fix for Private Equity (Gary Pearson), this is another wake-up call for those that are not ’structurally’ taking notice.

139

12 Comments

Beyond the Numbers: Why Operational Due Diligence is a GP’s True Stress Test In private equity, it’s easy to be dazzled by IRRs, glossy pitch decks, and compelling market narratives. But those are just the façade. Before committing capital for 10+ years, LPs need to know whether the operational foundation can support the weight of that vision. That’s where pre-investment operational due diligence (ODD) comes in, not as a tick-box exercise, but as a disciplined, structured way to uncover the strengths (and weaknesses) in governance, team stability, finance, reporting, and ESG/DEI integration. One of the most effective frameworks for this is the Institutional Limited Partners Association (ILPA) Due Diligence Questionnaire (DDQ) 2.0, a global standard that has evolved to address today’s complexity — from valuation methodologies to ESG commitments. By using it as a conversation starter rather than a compliance form, LPs can develop a clear, fact-based view of whether a GP can deliver on its strategy over the long haul. In my latest Substack article, I explore: - Why ILPA’s DDQ 2.0 has redefined operational due diligence. - How to balance factual verification with constructive engagement. - The five DDQ sections that deserve attention pre-investment. And yes, the article comes with a perfect visual metaphor, Thomas Cole’s "The Architect’s Dream" reminding us that ambition must rest on a solid foundation. 🎨 More on the painting see comments below.

9

4 Comments

💡Emerging GP Fundraising Insight #9: Portfolio Construction Questions Will Come Early LPs will press you on: • Follow-on strategy • Pro-rata participation • When you don't follow on • How much concentration risk you'll tolerate You don't need perfect answers but you do need thoughtful ones. If you haven't considered these scenarios, LPs will question your ability to manage a portfolio. Takeaway: Even hypothetical scenarios deserve a thoughtful response. Lack of prep reads as lack of capability. What's the toughest portfolio construction question you've gotten from an LP?

21

5 Comments

Every founder we invest in signs an Impact Pact. Written into our investment documents. Legally binding. Not as marketing. As requirement. Most impact funds talk about doing good. We structure it into every deal. The concept is simple: paying it forward. We share access to capital with founders the traditional VC ecosystem overlooks. In return, we expect our founders to pay it forward in three areas: Wealth sharing: How are you distributing ownership beyond the executive team? In 2024, our portfolio generated over $400 million in wealth creation—$342 million for BIPOC and women founders, plus $65 million in employee equity. Supplier diversity: How much spending goes to companies founded by people of color or women? Our portfolio directed $9 million to diverse suppliers last year—30% BIPOC-owned, 35% women-owned. Diversity goals: Not quotas. Intentionality. 92% of our founders are BIPOC. 81% of their employees are BIPOC. 77% of the $39.7 million in compensation went to BIPOC team members. Here's what makes this different: It's legally binding. Not in a deck. In the documents we both sign. It's specific. No vague language. Measurable commitments. It compounds. Year over year, these numbers grow because the structure demands it. The question I always get: "Does this work? Or is it virtue signaling?" Fair question. Here's the data: Our portfolio created 436 jobs in 2024 — a 48% compound annual growth rate since 2021. These aren't just any jobs. They're pathways to wealth in communities excluded from venture-backed opportunity. The paying-it-forward model creates a multiplier effect. When our founders prioritize diverse suppliers, those suppliers gain revenue and credibility that help them win more business. When our founders build inclusive teams, they tap talent pools competitors ignore. When our founders share equity broadly, retention improves and alignment deepens. Each company becomes a node in a network of shared access—not just a single investment, but a catalyst for ecosystem-wide change. Why structure impact this way? Because impact that isn't measured doesn't compound. When you invest in a founder, you're not just buying equity in one company. You're investing in their commitment to pay it forward — through the vendors they choose, the teams they build, the wealth they share. The Impact Pact ensures impact is intentional, measurable, and compounding. Returns are not concessionary. Our current Fund I: 34.8% gross IRR. 1.75x return multiple. More than two times above the median for comparable VC funds. The Impact Pact isn't altruism. It's a structured method for paying forward the access we provide and capturing the returns that come when overlooked founders get their shot. Fund II is open with the Impact Pact built into every deal. Same structure. Same accountability. Same thesis: that paying it forward isn't charity. It's alpha. If you're an LP who believes in compounding returns and compounding impact, let's talk.

68

34 Comments