Have you thought about what your founder futures look like if you’re suddenly not here—and whether your business worth is actually protected?
Interest (I)
You spend your time thinking about growth, valuation, exits, and risk—but many founders avoid the uncomfortable questions about legacy, control, and continuity. This episode connects estate planning to founder futures, showing how personal preparedness, governance decisions, and AI disruption all shape what really happens to the value you’ve built when circumstances change.
Desire (D)
By listening, you’ll gain:
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A practical framework for protecting your founder futures by understanding how estate plans, healthcare directives, and digital assets prevent chaos for your family and your company.
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Clear insight into scaling a venture-backed platform the right way, including term sheets, preference stacks, board control, and why “IPO-ready” thinking matters more than chasing an IPO.
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A CEO’s perspective on AI disruption and defensibility, including how category leaders must rebuild for an AI-native future before competitors force the change.
Action (A)
Press play and learn how to safeguard your founder futures while building a company—and a legacy—that holds up under real-world pressure.
Building Founder Futures: Legacy, Risk, and Preparedness
00:00–03:30
Jim Schleckser opens the episode by framing a topic most CEOs avoid: death, legacy, and preparation. The focus isn’t morbid—it’s about avoiding chaos and protecting the people and causes that matter most when a leader is no longer in control.
03:30–06:30
Cody Barbo is introduced as Co-Founder and CEO of Trust & Will, a digital estate planning platform trusted by over one million families. Jim highlights the scale, funding, partnerships, and why estate planning is a business problem hiding in plain sight for founders.
06:30–11:30
Cody explains why estate planning matters even for people with modest assets. Healthcare directives, digital assets, and final arrangements create certainty—and certainty is foundational to long-term founder futures, regardless of net worth.
11:30–16:30
The founder’s origin story: Cody’s personal experience with probate, outdated documents, and expensive attorneys revealed a massive gap in the market. He explains why being an industry outsider helped him see the problem differently—and build a better solution.
16:30–21:30
Jim and Cody discuss why most estate plans are either missing or outdated, and how COVID permanently changed awareness around mortality. The conversation ties personal preparedness directly to leadership responsibility and resilient founder futures.
Scaling the Business: Capital, AI Disruption, and CEO Reality
21:30–28:30
Cody breaks down Trust & Will’s pricing model, subscriptions vs. one-time purchases, and why recurring access matters as families grow and change. Estate planning is positioned as an evolving lifecycle product, not a one-and-done task.
28:30–38:30
A candid discussion on venture capital: term sheets, preference stacks, governance, and why founders must understand who really controls outcomes. Cody emphasizes that protecting founder futures often means walking away from bad terms—even when capital is tempting.
38:30–48:30
The leadership evolution story: rotating out early team members, bringing in experienced VPs and C-suite leaders, and managing the emotional cost of scaling. Cody explains why preparing for the next stage—not the current one—is critical to founder longevity.
48:30–1:02:00
AI disruption takes center stage. Cody shares why AI both excites and terrifies him—and why Trust & Will is rebuilding toward an AI-native future. The conversation highlights how failing to adapt could threaten both company value and founder futures.
1:02:00–1:15:00
The episode closes with scrappy growth lessons, including bold cold outreach that led to major partnerships like American Express. Jim reflects on fearless execution, preparation, and why founders who think long-term—personally and professionally—win.
About Cody Barbo
Cody Barbo is the Co-Founder & CEO of Trust & Will, the leading digital estate planning platform in the U.S., trusted by over one million families. Since launching in 2017, Trust & Will has modernized legacy planning with simple, secure, and attorney-approved online solutions tailored to state-specific laws. Under Cody’s leadership, the company has raised over $75 million in funding, and its customers report more than $100 billion in estate assets on the platform. Trust & Will supports 20,000+ financial advisors and 200+ banks and enterprise partners, including AARP, Fifth Third Bank, UBS, and USAA. Recently, the company introduced EstateOS, the first intelligent estate planning platform designed to revolutionize legacy planning through embedded AI guidance, streamlined workflows, and enhanced collaboration between families and financial professionals.
Trust & Will was recognized on the Inc. 5000 list for the second consecutive year in 2024. Cody was named an EY Entrepreneur Of The Year® 2023 Pacific Southwest Award Winner and regularly contributes to Forbes, Fast Company, and Inc. He is passionate about leveraging technology to transform estate planning from a transactional task into a deeply meaningful and personal experience.