The Third-Generation Challenge
In 2019, Robert Forsythe, CEO of Third Lake Capital, faced a critical mission: protect his Forbes 400 family’s wealth from the third-generation curse of dissipation. Managing over 500 LLCs and trusts, Third Lake relied on outdated tools such as Excel, QuickBooks, and SharePoint that risked errors, delays, and loss of family trust. With over 1,000 statements arriving in inconsistent formats each year, Robert clearly knew that without structure, the family’s legacy was vulnerable.
This case study was created for family office leaders who want to strengthen trust and modernize how their teams operate. It shows how Robert’s vision helped transform Third Lake into an example of efficiency through two innovations that work in harmony. iPaladin’s governance framework and Canoe’s automation come together to create a process that scales easily, maintains continuity, and keeps every document and decision organized within a single, reliable system.
Founded in 2013 as an embedded family office, Third Lake Capital became an independent single-family office in 2015, the same year Robert joined as Chief Operating Officer. A certified public accountant with a background in process consulting at PwC, Robert quickly recognized that the office relied heavily on manual systems. Like many family offices, Third Lake had expanded over time without a formal structure, which created inefficiencies and operational gaps.
These challenges were not unique to Third Lake. Across the industry, many family offices have struggled to keep pace with evolving technology. For Third Lake, the path forward was clear. The team needed to formalize operations, protect institutional knowledge, and build a structure that would sustain both trust and legacy.
After reviewing multiple vendors, Robert set out to find a solution that could truly transform how Third Lake Capital operated. At a Florida conference in 2019, he met Jill Creager, Founder and CEO of iPaladin, whose vision for unified processes immediately caught his attention. Later, while exploring automation tools for alternative investments, he discovered Canoe Intelligence, a company known for its advanced document automation capabilities. Together, iPaladin and Canoe helped Third Lake build the framework that would finally institutionalize its operations.
Jill, a seasoned trusts and estates attorney, encouraged Robert to move beyond isolated systems like email, spreadsheets, and CRMs. These tools were never built to manage the complex connections between fiduciary data, documents, and relationships. iPaladin introduced a single, integrated platform that reflected the structure of the family itself, by bringing together documents, workflows, and relationship management within one secure environment defined by role-based access.
“iPaladin gives team awareness,” said Tebbi Purvis, President of Third Lake Solutions. “A capital call triggers clear next steps.”
Long-range actions, like trust distributions 40–60 years out, were pre-scheduled, ensuring operational continuity across generations.
Scaling Efficiency Even with iPaladin streamlining operations, statement ingestion remained a bottleneck—costing 40–66 hours per month. Third Lake processed:
683 monthly statements
308 quarterly statements
104 annual statements
529 1099s and K-1s
9,772 documents annually
Canoe Intelligence uses purpose-built AI to check fund and custodian portals multiple times daily, automatically retrieving new documents within 24 hours of publication. This tech-first approach eliminates six manual steps per document while removing credential handling from staff entirely.
Unlike basic automation tools, Canoe’s AI models, trained on more than two hundred million data points from alternative investments, analyze each document to ensure accurate naming, filing, and data capture. This sophisticated extraction synchronizes seamlessly with iPaladin's workflow engine, transforming raw documents into structured and actionable records.
Many vendors promise API connectivity but still leave teams managing disjointed systems and manual steps. Canoe and iPaladin take a different approach, working together as one cohesive ecosystem. The result is a purpose-built solution designed from start to finish around the outcomes Third Lake needed most.
The combined iPaladin and Canoe system fundamentally changed the operational rhythm of Third Lake's family office. Routine audits no longer required time-consuming reconstruction of decision context or revalidation of unreliable data.
Every document, entity relationship, and governance action remained visible and traceable within a single, authoritative source of truth.
Many vendors promise API connectivity but still leave teams managing disjointed systems and manual steps. Canoe and iPaladin took a different approach, working together as one cohesive ecosystem. The result is a purpose-built solution designed from start to finish around the outcomes Third Lake needed most. Together, Canoe and iPaladin have eliminated nine manual steps per document.
“iPaladin and Canoe let our team focus on impactful work.” - —Robert Forsythe, CEO of Third Lake Capital.
The efficiency gains were so significant that Third Lake expanded beyond its original single-family office. Today, Third Lake Solutions supports more than ten families using the same operational framework, proving that institutional-grade performance does not require a large institutional team.
iPaladin moved Third Lake from reactive workarounds to a structured, institutional model. Canoe built on that foundation with automated, scalable ingestion that delivered efficiency gains across thousands of documents.
The real breakthrough came when the two systems worked together. iPaladin established disciplined, repeatable processes, while Canoe made those processes scalable without adding staff. This combination addressed both sides of the family office challenge, meeting the need for structure while delivering true efficiency.
The results speak for themselves. Third Lake now saves an estimated $250,000 each year in staff time and has reduced audit costs by half. Family members have direct access to accurate information, with ninety-five percent reporting greater trust in the data they receive.
The unified governance structure connects every participant through clearly defined access controls, authority levels, and approval paths. iPaladin and Canoe created a single operational environment where advisors, administrators, and family members operate from shared, real-time knowledge, without duplicating effort or introducing unnecessary risk.
Third Lake Capital's transformation demonstrates what becomes possible when family offices move from manual processes to institutional infrastructure. With iPaladin and Canoe working in concert, complexity becomes clarity, risk becomes confidence, and knowledge becomes legacy.
Third Lake's journey proves that lasting operational excellence requires addressing your specific challenges, whether that's building institutional structure, automating manual workflows, or both.
Every family office has unique needs. Explore how these proven technologies can address yours:
Institutionalize your family office. Preserve wealth. Build durable trust. Ensure legacy through structure.