By Nikki Cabus

Las Olas Venture Capital announced their latest investment in Miami startup Letterhead

Read Time 4 Minutes

Las Olas Venture Capital, or “LOVC,” has announced their latest investment in a South Florida startup – Letterhead.

LOVC is an early-stage venture fund investing in B2B software companies based in the Eastern US. Founded in 2016 by former entrepreneurs and headquartered in Florida, LOVC is now investing out of its $50M Fund II and typically leads $37M rounds with $1.52.5M checks in businesses with early commercial signals of product-market fit (typically $200K+ ARR). Their low-frequency and high-conviction investment approach (3-5 companies per year) allows us to be deeply collaborative and hands-on with the founders we partner with.

Miami-based Letterhead is a software platform for automating the creation and management of email newsletters, streamlining newsletter creation, distribution, and monetization for publishers and marketing teams to help produce meaningful content at scale. The company aims to revolutionize newsletter content automation. The company was founded in 2020 by Rebekah Monson, Bruce Pinchbeck, and Christopher Sopher.

“Rebekah and Chris have brought a unique content-centric perspective to the world of email communication, building a compelling solution for organizations of all sizes to leverage the power of personalization to communicate on the most enduring first-party channels there is,” said Sim Blaustein, Partner at BDMI.

Leveraging AI, Letterhead empowers users to manage multiple newsletters with the workflow of one, improving efficiency and scalability while retaining the ability to create quality, personalized, and bespoke products. Letterhead’s software works with a customer’s existing content management system and email service provider, enabling any company to use its tools with minimal switching costs.

“Our vision is to help every company engage their audiences with meaningful media content,” said Christopher Sopher, co-founder and CEO of Letterhead. “As changes to cookies and privacy rules make owning your audience more critical than ever, we think it should be way easier for teams to create quality content products for every segment of their community. Our first step is making it possible for any business to create great newsletters in a fraction of the time.”

Letterhead is trusted by the publishers of over 1,800 newsletters, indicating a strong market fit and demand for more intelligent audience engagement software. Customers include leading brands like Techstars and Salon.

The $5.3 million seed funding round, led by LOVC, is joined by Reign Ventures with participation from BDMI, Florida Opportunity Fund, and McClatchy. Letterhead will use the fresh infusion of capital to continue developing the platform, expand the team, and accelerate growth as it continues to innovate how newsletters are produced and managed. 

The Letterhead investment serves at LOVC’s 26th portfolio company and the 5th one for the 2023 year. 25 of the companies are currently active and the 26th being an exit. 20% of the active portfolio companies are in the state of Florida. LOVC currently has one additional deal expected to close soon and a second pending. 2023 was a big year for the firm and they expect to grow even more into 2024!

The Letterhead team is looking to make some critical hires across product, engineering and sales. Interested parties, can check out LOVC’s Portfolio Jobs & Careers Page and apply to the positions that match your qualifications at any of their portfolio companies.

“While there are many traditional email marketing products, none are focused on content-driven engagement like Letterhead is,” said Nate Vasel, partner at LOVC. “We were impressed with the team’s vision for an owned audience future powered by AI and automation and their consistent execution to grow the business.”

Born out of pure necessity, Letterhead is actually a spinoff of a product created for the co-founders other business, WhereBy.Us which launched the local Miami media site, The New Tropic. Once it began focusing on email newsletter formats, the business took off. People would ask about the tools used and ask the team if they could use them. After enough no answers, they decided to find a way to say yes and turn it into a business.

Media companies, nonprofits, higher education institutions, professional associations all began using the Letterhead tool increasing profits through AI, data analytics, integrations and the ability for clients to implement paywalled subsections, newsletters advertisements, easy-to-use templates and more.

To learn more about Letterhead, please visit