Tech Scenes Unplugged with Cody Bardo, CEO and Co-founder of Trust & Will

Tech Scenes Unplugged with Cody Barbo, CEO and Co-Founder of Trust & Will: Episode Summary and Key Takeaways

Building a startup is difficult.

Building a category-defining company is even harder.

In this episode of Tech Scenes Unplugged, Collective Genius Founder Jeff Martin sits down with Cody Barbo, CEO and Co-Founder of Trust & Will, to discuss entrepreneurship, scaling companies, operating systems, AI transformation, leadership, organizational design, and what it takes to build a mission-driven company in a category most people never think about until they absolutely need it.

What begins as a conversation about estate planning quickly evolves into a deeper discussion about startup growth, founder evolution, leadership systems, AI-native organizations, and the realities of scaling from a small team in a coworking space to a company serving hundreds of thousands of customers.

For founders, operators, executives, and investors, this episode provides an honest look at what happens when a company grows beyond its original systems and why successful organizations must continuously reinvent themselves as they scale.

Watch and Listen

Watch the Full Episode on YouTube

https://youtu.be/QuuNc2t-BJY

Listen on Spotify

https://open.spotify.com/episode/6QAiITmnHpoIsJjkDes858

Episode Overview

Cody Barbo co-founded Trust & Will in 2017 with a mission to make estate planning more affordable, accessible, and user-friendly for everyday families.

Inspired by personal experiences navigating probate and witnessing the challenges families face when proper estate planning is not in place, Cody and his co-founders recognized an opportunity to modernize an industry that had remained largely unchanged for decades.

Since launching, Trust & Will has grown from a startup operating out of a coworking space into one of the leading digital estate planning platforms in the United States, helping hundreds of thousands of families create wills, trusts, healthcare directives, and estate plans.

Throughout the conversation, Cody shares lessons from raising venture capital, building teams, scaling operations, creating organizational systems, working with enterprise partners, adopting AI, and preparing a company for long-term growth.

Building a Mission-Driven Company

One of the most compelling aspects of Trust & Will's story is that it began with a deeply personal problem.

Cody explains that his wife's family experienced firsthand the challenges and delays associated with probate after losing her father. At the same time, Cody was beginning to think about his own future, marriage, finances, and family planning.

As he explored estate planning options, he found a fragmented experience.

Legal services were expensive.

The customer experience was inconsistent.

Technology adoption was limited.

Most importantly, there was no trusted consumer brand dedicated to helping families navigate estate planning.

Rather than accept the status quo, Cody and his co-founders saw an opportunity to build a modern platform focused on accessibility, simplicity, trust, and customer experience.

Today, Trust & Will serves customers across virtually every stage of life, from young adults establishing healthcare directives to retirees planning wealth transfer and legacy preservation.

Why Great Companies Solve Human Problems

One of the strongest themes throughout the episode is the idea that successful companies solve meaningful human problems.

Estate planning is not merely a legal process.

It is deeply emotional.

It affects families.

It impacts relationships.

It influences financial outcomes across generations.

The founders of Trust & Will recognized that technology alone would not solve these challenges.

They needed to create an experience that combined technology, human support, trust, and accessibility.

This philosophy continues to shape the company's growth strategy and customer experience.

Scaling from Startup to Growth Company

Cody provides an honest look at Trust & Will's growth journey.

The company started with a small team, modest revenue, and limited resources.

The early years focused on validating product-market fit, learning customer needs, raising capital, and building distribution channels.

As the company gained traction, growth accelerated.

Revenue expanded significantly.

Headcount increased.

New enterprise partnerships emerged.

The organization became increasingly complex.

Like many founders, Cody discovered that the systems that work for a five-person startup do not necessarily work for a company with one hundred employees.

Each stage of growth required new operating rhythms, new leadership approaches, and new organizational structures.

The challenge was not simply growing faster.

The challenge was creating systems that could support sustainable growth.

The Importance of Organizational Systems

A significant portion of the discussion focuses on operating systems and organizational design.

Cody shares how Trust & Will evolved from a highly informal startup environment into a more structured organization with executive teams, management layers, planning cadences, communication systems, and operational frameworks.

One of the key lessons is that every stage of growth requires a different level of structure.

Too much process too early can slow innovation.

Too little process later can create confusion.

The goal is not maximum structure.

The goal is the right structure for the current stage of growth.

This idea aligns closely with a reality many founders experience.

Organizational systems should evolve alongside organizational complexity.

The best leaders continuously evaluate what is helping the company move faster and what is creating unnecessary friction.

Why Founders Need a Team Around Them

One of the most insightful parts of the conversation centers on Cody's decision to hire a Chief of Staff.

As the company scaled, Cody realized he needed more than administrative support.

He needed a strategic thought partner.

Someone who could help create systems.

Someone who could improve communication.

Someone who could help manage priorities, information flow, and organizational complexity.

Over time, the role evolved into what Cody describes as the "Office of the CEO."

This concept highlights an important reality for growing companies.

Founders eventually become leaders of a team dedicated to helping them lead effectively.

The CEO role becomes less about individual execution and more about communication, stakeholder management, strategic thinking, and organizational alignment.

AI Is Reshaping Every Industry

One of the most forward-looking parts of the conversation focuses on artificial intelligence.

Cody shares a candid perspective on the opportunities and risks AI creates for established technology companies.

While Trust & Will was built with modern technology, Cody openly acknowledges that the company was not originally designed as an AI-native business.

That realization created urgency.

As AI companies achieve unprecedented growth rates and new startups emerge with AI-first architectures, Cody believes every technology company must rethink its future.

His concern is not hypothetical.

If a well-funded AI-native company entered the estate planning market tomorrow, it could potentially reshape customer expectations and industry economics.

Rather than wait, Trust & Will is actively transforming itself into an AI-enabled organization.

The company's goal is not simply to use AI tools.

The goal is to become AI-native in its operations, products, and customer experience.

Creating an AI-First Culture

One of the most practical lessons from the episode involves organizational learning.

Cody emphasizes that adopting AI is not solely a technology initiative.

It is a cultural initiative.

Trust & Will has increased employee learning budgets, encouraged experimentation, introduced AI showcases, and created expectations that employees continuously explore new tools and workflows.

The objective is not for everyone to become an AI expert.

The objective is for everyone to develop an AI-first mindset.

This approach reflects a broader shift occurring across industries.

Organizations that learn quickly are increasingly outperforming organizations that simply work harder.

Why Leadership Still Matters

Despite the excitement surrounding AI, Cody repeatedly returns to a fundamental principle.

Technology does not replace leadership.

Technology amplifies leadership.

Organizations still need direction.

Teams still need clarity.

Customers still need trust.

Employees still need purpose.

Founders still provide vision.

One of Cody's concerns about excessive automation is the possibility of removing the human element that gives organizations meaning.

Technology can improve efficiency.

It cannot replace culture.

It cannot replace values.

It cannot replace relationships.

It cannot replace leadership.

For Cody, preserving the soul of the organization remains just as important as improving operational performance.

The Power of Founder Relationships

Another recurring theme throughout the episode is the importance of co-founder alignment.

Cody repeatedly credits his relationship with co-founder Daniel Goldstein as one of the most important factors behind Trust & Will's success.

The partnership extends beyond work.

It is built on trust, shared values, mutual respect, and long-term commitment.

As organizations scale, strong leadership relationships create stability.

They provide a foundation for decision-making.

They help organizations navigate uncertainty.

They create resilience during difficult periods.

In many ways, the Trust & Will story demonstrates the importance of building not only great products but also great partnerships.

Key Quotes from Cody Barbo

"Estate planning should be affordable and accessible for everybody."

"The systems that got you here won't necessarily get you there."

"The role just gets naturally more external as the business scales."

"You need a soundboard as a founder."

"Keeping things as simple as we can goes a long way."

"If we do not make this transformation to an AI-native estate planning platform, someone else will."

"Organizations need to be retrained to become AI-first."

"You take the founder out of the company, you take the soul out of the company."

Key Takeaways

Great businesses often begin by solving deeply personal problems.
Mission-driven companies create stronger customer connections.
Organizational systems must evolve as companies grow.
Founders need strategic support as complexity increases.
Chiefs of Staff can become critical scaling partners.
AI is reshaping every industry, including highly regulated industries.
Learning velocity is becoming a competitive advantage.
Simplicity often scales better than complexity.
Trust remains one of the most valuable business assets.
Technology should enhance leadership, not replace it.
Strong co-founder relationships create organizational stability.
Growth requires continuous adaptation and reinvention.

Frequently Asked Questions

What is Trust & Will?

Trust & Will is a digital estate planning platform that helps families create wills, trusts, healthcare directives, and other estate planning documents.

Why is estate planning important?

Estate planning helps individuals protect assets, reduce legal complications, and ensure their wishes are carried out after death or incapacity.

What inspired Trust & Will?

The company was inspired by personal experiences navigating probate and recognizing the lack of modern, accessible estate planning solutions.

Why do startups need operating systems?

Operating systems help organizations create alignment, accountability, communication, and execution as complexity increases.

What is a Chief of Staff?

A Chief of Staff helps leaders manage priorities, communication, strategic initiatives, and organizational effectiveness.

Why are founders adopting AI?

AI enables founders and organizations to improve efficiency, accelerate learning, automate repetitive work, and improve decision-making.

What does it mean to be an AI-native company?

An AI-native company is designed with AI integrated into its products, workflows, decision-making processes, and operating model.

Why do organizations need learning cultures?

Organizations that learn faster often adapt more effectively to changing markets, technologies, and customer expectations.

Why does trust matter in business?

Trust influences customer relationships, employee engagement, partnerships, and long-term organizational success.

How do founders maintain focus while scaling?

Successful founders build systems, create strong teams, establish operating rhythms, and delegate effectively.

Why This Conversation Matters

Many startup conversations focus on fundraising, valuations, and growth metrics.

This conversation focuses on something deeper.

How organizations evolve.

How founders evolve.

How systems evolve.

And how technology is reshaping the future of work.

Trust & Will's journey demonstrates that long-term success is rarely about a single breakthrough.

It is about continuously improving products, people, systems, and leadership while staying connected to the mission that inspired the company in the first place.

As AI transforms industries and organizations become increasingly complex, these lessons are becoming more relevant than ever.

Related Insights

About Cody Barbo

Cody Barbo is the CEO and Co-Founder of Trust & Will, one of the leading digital estate planning platforms in the United States. Cody is a technology entrepreneur, startup founder, and advocate for making estate planning more accessible, affordable, and trustworthy for families across the country.

About Collective Genius

Collective Genius helps growth-stage and mission-critical organizations improve leadership, communication, accountability, execution, and organizational alignment through coaching, advisory services, and operating systems.

Learn more:

https://www.collective-genius.com

About Peak OS

Peak OS is the business operating system developed by Collective Genius to help organizations scale effectively through strategic planning, communication rhythms, leadership development, accountability systems, and organizational learning.

Peak OS helps organizations create clarity, alignment, and execution while reducing dependency on founders and individual contributors.