founder

The Legion Blueprint: Ryan Bettencourt’s Approach to Software Growth

Introduction

This name might sound familiar. We last spoke with Legion Works founder Ryan Bettencourt in 2020. As a refresh, Legion Works buys and scales software companies. We spoke with Ryan to learn what he and his team have been working on since we last saw them raise and how this model is unique.

Note: This interview was conducted over phone and email. It has been lightly edited for clarity and length.

Olivia Strobl

We have seen you raise capital online before, can you remind us what you are working on?

Ryan Bettencourt

Yes, of course.  Legion Works was founded by an experienced team to build and buy online software companies and then use a playbook we have built up over our years of running online companies to help each company scale.  We also centralize all of the administrative functions at the Legion level so that each of our companies can focus on growth activities.  You can learn more about what we do on our investment website.

Olivia Strobl

What major updates can you report since your last raise?

Ryan Bettencourt

We continue to raise under our existing Offering.  However, we recently launched a campaign in partnership with StartEngine.  Since we first started raising for Legion Works, we have raised over $12.3 million from over 4,500 investors.  Over $900,000 has been raised at our current offering terms.  Since our founding, we have acquired 5 software products and have grown our revenue from about $2,000 in 2020 to just over $2.5 million in 2022.  We are also working on building two new companies – one leverages AI to help fans better connect with the athletes and teams they most love and the other replicates Growth Collective (a premium freelancer platform we acquired from two former Google employees in 2021) to enter a new market vertical.  We have kept true to our original business plan by centralizing all of the admin for each of our companies to allow each of our subsidiary companies to focus on growth.  We believe we have a strong leadership team as we look to evolve and grow Legion.

Here is a quick video we put together with a bit more information on some of the things we have accomplished to date

Olivia Strobl

You have a unique business model. Can you remind us of how it works? What are the benefits of this model?

Ryan Bettencourt

Before starting Legion, our founding team started and led many online companies across SaaS (Software as a Service), online services, online marketplaces, and e-commerce. Through those experiences for starting, scaling, and, in some instances, selling the companies we ran, we believe we built a playbook of strategies and tactics to give online companies a better chance of succeeding.  We also learned through those experiences that all start-ups struggle between running the company (managing finance, taxes, capital raising, human resources, etc..) and growing the company (through product, marketing, and sales). So, at Legion we have focused on: 1) Building and buying companies and software products that have gotten initial traction but are struggling to scale further; 2) Centralizing those tasks required to run those companies at the Legion level so that each company can focus on growth activities; 3) Providing each company with a growth playbook that we have built up over our years of leading online companies – this playbook covers product, marketing and sales strategies and tactics.  Further, each of our subsidiaries has a leader, and we manage our businesses to a model (we wrote a blog post on this that can be seen here).  Revenue from each of our subsidiaries is then consolidated at the Legion level

Olivia Strobl

How do you determine what companies you build and buy?

Ryan Bettencourt

Since our founding, we have focused on building and buying companies that help others grow.  We say, “we provide online products that help ambitious companies grow.”  This means we have focused on companies and markets primarily in marketing and sales tech.  When we find a market we like, we see whether an existing player has gotten traction and can be acquired for a reasonable price.  We typically look outside of the major tech hubs like San Francisco, LA and New York as we believe valuations can be inflated there and that great companies are being built in smaller markets worldwide.  If we find such a company, we gauge the company’s interest in selling and then do our due diligence before making an offer.  If we find a market that we like but can’t find a company that has established good initial traction and is open to selling at reasonable terms, we look to build something in that market.  For example, I referenced Growth Collective above. We believe the world of work has fundamentally shifted over the last five years to many of the most talented marketers working full-time for established companies to many of the most talented marketers wanting to work independently and for a handful of great clients.  We then found Growth Collective, a company that had gone through the Techstars program and had gotten good initial traction.  We got to know the company’s founders (former Google employees) and liked what they had built and their vision for the company.  So, we acquired Growth Collective in 2021.  We have since added additional team members and invested in rolling out our playbook across the company’s marketing, sales and product efforts.  In fact, we are about to roll out a new technology platform for Growth Collective that we are excited about.

Olivia Strobl

What is your exit strategy?

Ryan Bettencourt

We deeply appreciate our investors and work hard to keep them informed as often as possible.  We are regularly keeping an eye on the investment, M&A and public markets while also staying heads down in building the foundation of a company to not only create options for liquidity but also show strength after such liquidity becomes available. We believe if we continue to execute our business plan we can create options for being a public entity or being acquired by a company with a focus in our markets.

We look forward to seeing where Ryan and his team take the company. Legion Works is currently raising on StartEngine

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About: Olivia Strobl

Olivia comes to KingsCrowd with a background in venture capital and technology. She spent time at Glasswing Ventures, an AI-focused venture fund in Boston, before joining the KingsCrowd team. There she helped develop machine learning algorithms for the opportunity qualification of preseed and seed-stage startup companies. Prior to her time at Glasswing, Olivia worked in a lab studying the neural correlates of attention. She holds a degree in Neuroscience from Wellesley College.

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