Jun 12, 2020 · 25m · top-founders
Trust and Will Company Passes 5k Customers, $1m in ARR Digital Way to Do Estate Planning
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Trust and Will founder Cody Barbo discusses democratizing estate planning through accessible digital software, scaling past 5,000 paying customers, and transitioning to an annual subscription model supported by strategic B2B partnerships.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 32.3% of the talking time here. How this is scored →
Nathan as informed peer 4.9 Guest teaching 2.3 Guest disagreement 1.4 Nathan pushing back 2.9
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 14:24 Guarding customer metrics against competitors
Cody explicitly pushes back on revealing exact customer counts, stating he is playing a mental calculation to protect proprietary data from competitors.
Hardest push from Nathan ▶ 20:08 Refusing conflation of upfront fees and ARRNathan refuses to accept Cody's assertion of a $1M run rate without separating upfront setup fees from genuine annualized recurring subscriptions.
Biggest teaching moment ▶ 2:21 Educating on mass-market estate planning necessityCody reframes Nathan's assumption that estate planning is strictly for the wealthy by outlining critical guardianship and probate protections for everyday families.
Nathan holds their own ▶ 22:50 Instant runway and monthly burn calculationsNathan takes the $6M round and 24-month operational runway to immediately calculate the company's net burn ceiling at roughly $250k per month.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Episode Preview: Customer Count and Growth | 4 | 3 | 1 | 2 | Nathan probes the core business model, asking whether the product is a pure SaaS play or exclusively targeting wealthy individuals. Cody clarifies common misconceptions about estate planning and details the demographic mix of users. | |
| Product Offerings, Pricing Tiers, and Cost Comparisons | 5 | 2 | 1 | 2 | Nathan quickly calculates the combined costs of the three pricing tiers and asks if power laws dictate revenue concentration. Cody explains how the trust package drives the majority of top-line revenue compared to the starter guardian product. | |
| Founding Journey, Venture Funding, and Digital Will Milestones | 4 | 2 | 1 | 1 | Nathan asks for a breakdown of early milestones and MVP capital efficiency. Cody outlines the company's accelerator timeline, initial capital raised, and their launch of the first electronic will in US history. | |
| Customer Conversion Rates and Transitioning to Recurring Subscriptions | 6 | 3 | 2 | 4 | Nathan presses on the transition from one-time setup fees to recurring revenue, noting that venture backing allows longer CAC payback windows. Cody explains why maintaining paid entry pricing builds consumer trust over free documents. | |
| Channel Partnerships and the Haven Life B2B Model | 5 | 2 | 3 | 4 | When Cody hesitates to share exact customer numbers due to competitive concerns, Nathan pushes back by emphasizing that public success comes down to execution. Cody then breaks down their wholesale partnership structure with Haven Life. | |
| Team Composition and Expanding into the Financial Advisor Network | 5 | 2 | 1 | 3 | Nathan questions how churn can be measured before true subscription cycles are mature. Cody shares their long-term vision of supporting customers across their lifetime and moving into trust distribution. | |
| Revenue Run Rate, Burn Management, and Runway Toward Series B | 7 | 3 | 2 | 6 | Nathan drills down on the definition of run rate, calling out the difference between one-time setup revenue and pure recurring subscription revenue. He also calculates monthly net burn based on the Series A raise and runway timeline. | |
| Famous Five Rapid-Fire Questions | 3 | 1 | 0 | 1 | Nathan conducts the standard rapid-fire questions covering favorite books, role models, and sleep habits before giving a concise summary of the business. |
Statements from this episode (18)
70% of Trust & Will members are ages 25 to 50
“Yeah, so majority, about 70% of our members are gonna fall within the kind of 25 to 50 range and have minor children. It doesn't discount the fact that 30% of our members are 55 plus, but our core focus is really people that are starting families, buying their…”
40% of baby boomers do not have an estate plan
“Yeah, 40% of boomers have no form of estate plan, which is honestly a crisis.”
Traditional estate planning attorneys charge between $2,000 and $5,000
“Because it's kind of crazy, like an estate plan, if you go to an attorney, you're going to spend anywhere from two to 5000 dollars to set this up, just to make a simple update, like you had another kid, you bought a new property, you moved It might cost you a …”
Trust packages at $500 drive significant revenue for Trust & Will
“The trust makes up a considerable amount of our revenue, considering that our base products, the guardian is at 50 dollars and our trust product is at 500. It is a 10 X jump to the trust.”
45 million US parents with minor children lack estate plans
“Forty five million parents with minor kids in this country don't have any estate plan.”
Trust & Will raised a $2M seed and $6M Series A
“We raised our seed round that we announced in January of last year of two million. We announced our series a last month of six million.”
Trust & Will has reached 65,000 total user sign-ups
“We've had about 65,000 people sign up for Trust & Wealth for one of those three products.”
Trust & Will executed the first US electronic will in 2019
“And then we have our kind of history defining milestone was last year in January, we did the first electronic will in history, US history, which means digital signature, digital notary, digital storage of documents.”
Trust & Will spent roughly $200,000 to develop its MVP
“And then by the time we finished tech stars, I think we wrapped up like you could call it pre-seed funding, but we had collected about half a million dollars at that point, but we had invested a couple 100,000 to get the product to where it needed to be.”
Trust & Will converts 10% to 20% of its 100+ daily signups
“We're seeing about a hundred signups a day or more, which is fantastic. And our conversion is anywhere from 10 to 20%, depending on the product, depending on the day.”
1% of Trust & Will users organically return to update documents
“So we're seeing about one in a hundred folks come back to make that initial update without any marketing around the fact that, hey, you should come back and update if you've had any of these life events as triggers.”
Why offering free estate planning products creates consumer distrust
“Because we felt that a free product within estate planning can actually communicate distrust. Well, what's the catch if I'm making these sensitive decisions, right? What's the catch of a free estate planning document? So that's why we like the paid product.”
Trust & Will has surpassed 5,000 paying customers
“I mean, it's north, it's between comfortably sharing north of 5000.”
Haven Life includes free Trust & Will products for policyholders
“So we have Haven Life where they have a benefits package called Haven Life Plus. They've wrapped in our will as a free will for their life insurance policyholders.”
Trust & Will targets 300,000 financial advisors for channel sales
“So one of the roles that we're hiring for right now is a channel sales rep. We want to tap into the 300,000 financial advisors, wealth managers, CFPs in the country that often talk to their clients about estate planning from day one.”
Trust & Will charges returning canceled users full price for updates
“That if they canceled out of the subscription, they came back in three years because they had another kid, they want to update their trust, it's going to cost them the full purchase price versus that 50 bucks a year recurring.”