A Read
A read on where AI actually fits in the B.I.G. Capital portfolio. And where it does not.
Resource One. E-Net. ServicePRO. Open Minds. Four mature products, one 2026 question.
The Window
B.I.G. Capital has held four mature software businesses for a long time. Resource One since 2010. E-Net. ServicePRO since the 2016 Help Desk Technology transaction. Open Minds. Each product sits in a different corner of the enterprise stack: incentive compensation, mainframe data replication, IT service management, infrastructure migration.
Each one faces the same question in 2026. Application-software valuations are splitting. AI-enabled assets trade at a premium. Assets without a coherent AI story trade at a discount. For a family office with a long-term hold thesis and a Diamond-level commitment to the South Florida tech ecosystem, getting the answer right matters more than getting it fast.
The Frame
Most AI adoption fails the same way. Teams point a large language model at a problem that should have been a rules engine or a Postgres query, and they pay for the mistake in latency, cost, and governance headaches.
Jake Van Clief calls this the 60/30/10 split.
60%
Traditional code and database work
Indexing tickets. Routing by team. SLA tracking. The work Postgres does faster, cheaper, and with better guarantees than any model.
30%
Rule-based logic
Priority assignment. Escalation triggers. Compliance flags. Deterministic by design, auditable by default.
10%
Genuine LLM territory
Ambiguous intake. Unstructured knowledge-base retrieval. Resolution suggestion. The narrow layer where a model earns its cost.
The engineering work is deciding, for each piece of a product, which layer it belongs on. That is the orchestration question. Applied to the B.I.G. portfolio, that means four orchestration maps, one per product, and a shared methodology the holdco can audit.
Reference
A recent Eduba engagement is the closest reference point. A multi-agent compliance platform that collapsed 160 hours of document-heavy regulated workflow to under five minutes.
The engagement structure matched a family-office sensibility. Scoped retainer, playbook delivery, long-tail alignment on the workflow time saved.
ServicePRO's ITSM workload is structurally similar to that workflow, in a different vertical. Intake. Routing. Compliance. Documentation. Handoff. The right orchestration layer applied correctly is the defensive move against ServiceNow and Freshservice, and it avoids the trap of ripping and replacing a 3,500-client install base.
Resource One
Incentive compensation. Since 2010.
E-Net
Mainframe DB2 replication.
ServicePRO
IT service management. 3,500+ clients.
Open Minds
High availability and migration.
The Methodology
Eduba's methodology is published. Interpretable Context Methodology, submitted to ACM TiiS.
The point of ICM is that agent context is a folder structure. For a holdco with four products and four customer bases, that structural discipline is the difference between reusable methodology and a stack of one-off chatbots.
Repo: github.com/RinDig/Interpretable-Context-Methodology-ICM-
Adjacent work: the Ethics Engine, a psychometric assessment tool for evaluating ideological and moral patterns in LLMs. Relevant for any portfolio company operating under regulated-industry scrutiny.
Paper: arxiv.org/abs/2510.11742
Repo: github.com/RinDig/AuditEngine
Credibility
Jake Van Clief is the founder of Eduba. Marine Corps veteran, eight years on cryptographic systems and F-35 and F-18 avionics. MSc Future Governance from the University of Edinburgh. Published in ACM TiiS and arXiv.
- 1,500+ enterprise learners trained since May 2025, including Pacific Life, Colgate-Palmolive, and KPMG UK (Big Four).
- 6,000 to 9,000 hours saved per year across trained cohorts.
- 95% of participants still using the tools thirty days after the workshop.
- NLP Logix has been in machine learning since 2011 and runs over 150 data scientists. Eduba partners with NLP Logix for work that sits below the orchestration layer.
"Things may come to those who wait, but only the things left by those who hustle."
Abraham Lincoln
Next Step
Thirty minutes on the whiteboard. One portfolio company, one workflow that eats hours.
Matt Creamer is Eduba's CRO and the person at the event. Bring one portfolio product and one workflow inside it that costs more time than it should. We run a live orchestration audit and leave you with a one-page 60/30/10 map specific to that product. No deck, no follow-up sequence.
Book time with Matt CreamerCalendar: calendly.com/thecro-eduba/30min