Deal to Watch: Your Will, Your Way

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Raised $7,000 as of January 28th, 2019

Trust & Will has been selected as a Deal To Watch, which is reserved for the top 10-20% of all deals we analyze in our due diligence funnel.


Traditional estate planning and making of wills is an expensive, time consuming, and often confusing process. As a result, only about 4 in 10 American adults have estate planning documents such as a will or living trust and 42% of boomers, aged 53-71, do not have any estate planning documents. Looking at the younger age groups, an overwhelming 78% of Millennials, aged 18-36, and 64% of Generation Xers, aged 37-52, do not have any form of a will.

The top two reasons given for this failure to tackle or complete these legal documents are that potential customers are either procrastinating (47%) or feel they do not have enough in assets to leave to anyone. (27%).

To make matters worse, those who seek out attorneys and legal advice in order to begin the process of estate planning have to shell out anywhere from $300 to over $1,000 for a simple, lawyer-drafted will or trust. Without making a valid last will and testament before passing, state law decides what happens to one’s estate and who inherits what – making the need to organize one’s assets even more pressing and necessary.


As a solution to the many hassles that come with estate planning, Trust & Will has designed an end to end solution for creating, storing, and updating estate plans, wills, and trusts online.

In only a 15-minute-long process vetted by attorneys, Trust & Will eliminates the need to physically be in the presence of a lawyer in order to get legal affairs in order – at a significantly cheaper cost. Essentially, they make estate and will planning extremely approachable and intuitive, when most people get uncomfortable at the idea of it, and find it intimidating.

Trust & Will is taking advantage of an incredibly large market that is still exceedingly antiquated. This company is targeting the millennial population, one of six of whom have at least $100,000 saved, as well as older generations that are looking for more convenient methods when it comes to legal planning. In addition to needing will and trust services, populations will require estate planning, especially since there are 127.6 million households in the US.

Within this large market are various competitors we should highlight, but from our analysis we still feel there is far from a dominant incumbent that has won the market.

The largest ‘competitor’ would be LegalZoom, listed as the nation’s top online legal document company. It is an incredibly easy to use platform, is extremely secure, and costs $69 for a basic will – the same price as Trust & Will. However, LegalZoom is also known for helping you create LLCs and other business entities. While it does enable will planning, it’s far more of a generalist legal documentation player, than a serious threat to being the next dominant management platform for trust and wills.

Similarly, RocketLawyer, with $46M in funding to date provides a wide variety of legal documentation services, much in the way that LegalZoom does including estate planning. Once again, their lack of specialization makes them an indirect competitor, but their backing by Google Ventures has made them the fastest growing online legal service.

On a similar playing field to Trust & Will is – set up much like Trust & Will with a modern, consumer friendly interface priced slightly below T&W at $49 for a basic will.

This team has raised a $7M Series A, and is very much in a similar stage of market progress as T&W. However, a major downside when it comes to is their lack of ability for attorney interaction, which can be useful when creating legal documents.

Amongst these competitors, Trust & Will is nicely positioned to provide the most seamless and user friendly service for creating these types of legal documents, which can be daunting and uncomfortable. Solving this key challenge is what will differentiate and enable T&W to progress in gaining market share within their specific niche legal vertical.

Why We Like it

1. Specialized subscription plan: Trust & Will’s offering includes a quick quiz online that allows users to gauge which of their three plans – “Guardians”, “Wills”, and “Trusts” – is best for them. Each plan is priced according to its services and are all reasonable and comparable to competitors, given their high level of security when it comes to document storage, easy access and download of documents, and immediate ability to receive information and advice through live chat.

Having multiple plans provides an opportunity to integrate and cross-promote products as well as target diverse groups of consumers. They also guarantee a complete 30-day trial period with a full refund of services if the customer is unhappy – significantly more than the 7 days or less that competitors give and definitely a solid traction point for them as a new company.

Most importantly, by tailoring to users and providing them with customized offers to what they need, they make the trust and will process less daunting and intimidating, which is ultimately what will drive their customer base adoption.

2. Substantial backing: If Trust & Will’s expansive reach in 49 states and the District of Columbia as well as their 11,000+ current users, and recent $2M in funding including from the famous Rise of the Rest Fund is not reason enough to keep an eye on the growing company, then their partnerships certainly are. Supported and highlighted by companies like MassMutual, Haven Life, CBInsights, and Inc., it is incredibly apparent that Trust & Will provides services these companies believe in.

3. Opportunity for additional revenue: Looking at Google’s heaving funding and interest with RocketLawyer, it is quite possible that another large file sharing or data company might be interested in Trust & Will, as an expansionary legal documentation category, which could provide a nice exit opportunity for this organization.


Trust & Will was founded by Cody Barbo, Daniel Goldstein, and Brian Lamb – all incredibly experienced in building successful startups and working with Fortune 100 companies on numerous product development and software applications.

Cody Barbo himself has been the founder of other startups, including Industry and Niche. Industry is currently in its post-launch stages, functioning as a professional network and hiring solution for top talent in the service and hospital industry. Goldstein has his own share of experience benefitting Trust & Will, having been the VP of Strategy and Business Development at Seamgen, responsible for marketing, account management, and revenue management of mobile and web applications Similarly, Brian Lamb worked at Seagmen, holding the position as VP of User Experience. In addition to this, Lamb spent time at Ninthlink as a Senior Interactive Designer responsible for creating digital campaigns.

Not only are all three co-founders well equipped to create and manage this online legal service, but they have an entire team of financial and legal advisors guiding them along the way to ensure they end up with the best possible product.


The best startups provide intuitive solutions in markets with irrational ones. Trust & Will fits the bill perfectly as it relates to this issue. In fact the largest concern we have for Trust & Will is not old school incumbents, but rather human nature itself.

Changing consumer behavior to embrace planning for life after we pass is frankly a challenge no one has solved. Removing nearly every friction point in the process is a major step, but there is still just genuine consumer behavior that is hard to change, which we think is the one true limiting factor to the upside of this business.

With their easy to use platform, strong investment backing and partners, a seamless user experience, promise of 24/7 advice, lengthy trial period, and significant founder and team experience – Trust & Will is definitely a Deal to Watch.

About: Chris Lustrino

A Boston College Eagle for life, on a mission to democratize startup investing for all people at KingsCrowd, with a passion for Fintech, investing, social impact, doing well and doing good, and an avid runner, cyclist and writer.

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