Toast, the Restaurant Industry and an Exceptional Case for Vertical Payments

Two weeks ago Toast announced its $400M raise on a $4.9B valuation, and for the first time, I feel that people outside the restaurant industry realized just what an amazing company Toast has become. It is an exceptional example of vertical payments and well on its way to becoming an industry platform.

At F-Prime Capital, we invested in the first institutional round of capital in 2015, and before and after, we have looked at dozens of other industries for vertical SaaS + payments opportunities. Few combined the magic ingredients that made Toast so successful. We got a lot of things right about the restaurant industry in our original investment thesis and got lucky on others, but overall we have learned so much more about building vertical software businesses.

This post is about why the restaurant sector has been an ideal industry for vertical payments and how Toast executed against it so well. I hope it also helps founders building vertical payments businesses in other industries to distinguish good from great verticals, how timing matters and how to judge how high the ceiling can be. I’ll organize the rest of my thoughts into Market, Team, and Timing.

In the beginning…

As with all breakout successes, the story starts with a great team and great execution. Chris Comparato, Steve Fredette, Tim Barash, Aman Narang and Jonathan Grimm are superb operators and have built an amazing team around them. They were united first by Steve Papa, Founder/CEO of Endeca, where they helped build Endeca to a $1.1B sale to Oracle. Then Steve backed them as their primary investor until 2015 at Toast. Talk about founders giving back and creating new founders.

Rock, paper, scissors. Market, team, timing.

It does not happen without a great team, but never underestimate market and timing. They make the difference between good and great companies.

Market

#1. High velocity sales cycle meets architectural shift to the cloud. Restaurants form and fold all the time. Successful restaurants add new locations. On average, 10,000–20,000 new restaurants start every year. Selling into the restaurant industry gives a startup a lot of shots on goal, often without the need to displace any vendors. In addition, the restaurant industry tended to refresh on-prem point-of-sale (POS) systems every five to seven years. That was both an indictment of on-prem, server-based software, but also a natural result of POS terminals obsoleting as technologies and security improved (e.g., EMV).

That said, Toast launched as all industries were moving to the cloud and this refresh in the restaurant industry was going to be different. Square had already introduced cloud + tablet-based POSs in 2009 to coffee shops and mom-and-pop stores, and nearly all quick-service and full-service restaurants would refresh to a cloud-based solution. Enter Toast with a purpose-built, all-in-one cloud-based solution.

#2 Era of the Payment Facilitators (Payfacs). By 2012 when Toast launched, the payment facilitator (Payfac) model was flourishing and this allowed Toast to redefine the POS business model and literally alter the competitive playing field. By embedding payments into their software stack, they were given two levers for charging customers — SaaS licenses and payments interchange. Restaurants were going to pay someone interchange, but now Toast could give them their core software platform for running the restaurant while also monetizing the payments. Providing an all-in-one solution offered value to both the restaurant and Toast.

A bonus of vertical payments in the restaurant industry is the low-risk profile. Compared to a marketplace like Etsy or Stripe’s broad customer base, restaurants are relatively easy to KYC, chargeback risk is low and transaction monitoring is more predictable.

#3 Geographic density leads to viral growth. Consumer businesses search for viral growth, but few enterprise businesses enjoy the same, though there are notable exceptions (e.g., Atlassian, Slack, Asana). Early on we found that achieving density in a city actually stimulated organic growth and higher sales productivity. Restaurant owners dine at other restaurants. Waiters and waitresses move from restaurant to restaurant. This was a remarkable phenomenon to watch and a beautiful characteristic of the restaurant industry.

Team

#4 I will be a platform when I grow up. With the shift to the cloud, Toast had the chance to re-define the product category from standalone POS terminals to a true software platform with APIs and a world of best of breed partners and applications. Not only did this allow Toast to offer more value to restaurants, but it planted the seeds of its own enhanced role as a platform layer in the industry.

#5 An enterprise team for an enterprise-grade market. I’ve found that quick-service (QSR) full-service restaurants (FSR) have just the right amount of enterprise complexity. Managing one, if not many locations, presents ample complexity, including: menus, cook stations, staffing, customer CRM, inventory, procurement, etc. Coming from Endeca, the Toast team built with an enterprise software mindset and an obsession for customer success. This is one of the main reasons it’s been difficult for Square to move upmarket.

I say ‘the right amount of complexity’ because I have found other attractive verticals, like hotels, are sufficiently big beasts, built around all-encompassing property management systems and are hard to displace without feature parity. Too much complexity and a startup has a hard time penetrating.

#6 Android, not Apple. Many of Toast’s competitors went to market with Apple tablets. They were the rage and looked beautiful. But we all know the cost of that brand. Toast understood that Android-based devices would follow a much faster cost curve while offering an order of magnitude more options for supply and configuration. While that choice seemed obvious to Toast, not all competitors saw it that way, including Revel and Touch Bistro.

Timing 

#7 The restaurant sector got hot. It didn’t hurt that venture firms would go on to invest $3.4B in restaurant tech startups starting in 2014. Led by online delivery services like GrubHub and DoorDash, hundreds of startups formed to serve restaurants, both enabled by cloud-based POSs, which permitted easier integrations, and reinforcing the role of POSs as the new platform layer.

#8 Access to cheap capital. What a time we’re living in. Good teams understand the capital markets. Toast recognized that it could raise a lot of capital based on its strong unit economics, impressive go-to-market execution and large market opportunity. When you see an opportunity to be a platform, it is rational to press your advantage and gain market share.

The Future is Bright

As exciting as the first five years have been, the restaurant industry is still in the early innings of its shift to the cloud and vertical payments. Older, incumbent vendors like NCR and Oracle/Micros constitute most of the POS market.

This first phase has so much upside left. Mirroring the phenomenon I described of density leading to viral growth, the restaurant POS will have a winner-take-most outcome. Even incumbent vendors enjoyed that. Peak market shares were ~30% for NCR and 21% for Micros, with Toast on its way to winning its own significant market share.

The second phase involves the POS as a platform — the software central nervous system for the restaurant. Toast already has become a hub for third-party applications like staffing and inventory management. In five years, restaurants will not have two, three or four tablets on the counter for GrubHub, DoorDash, Caviar and others.

At the same time, Toast and others will offer additional services themselves. Toast acquired payroll provider Stratex and launched Toast Capital in December. I’m especially excited to see the suite of FinTech services Toast will offer to restaurant owners and employees. The POS is a fraction of the addressable market at each restaurant. As a public company, Square has continued to grow net revenue 60% Y/Y even as it surpasses $1.5B. The unit economics of QSR and FSR are several times more attractive than the smaller retailers that comprise Square’s customer base.

The restaurant industry has proven to be an ideal market for vertical payments and the ceiling for players like Toast is very high.

 

10 Rules Entrepreneurs Need to Know Before Adopting AI

It is in the ethos of established tech companies to build generic solutions for customers across industries. But for challengers, the more they can focus on solving core business problems, the more successful they will be.

Although adoption of artificial intelligence (AI) and machine learning (ML) for the enterprise is still in the early days, the technology has matured enough for entrepreneurs to start gathering inspiration and evaluating opportunities for potential applications.

Business leaders are just beginning to adopt artificial intelligence and machine learning into their operations. In this story for Harvard Business School’s Working Knowledge, Rocio Wu offers insights into how entrepreneurs can start riding the wave.

Originally published in HBS Working Knowledge. Read the full story here.

MoEngage

MoEngage is an intelligent customer engagement platform, built for the mobile-first world. With AI-powered automation, optimization capabilities, and in-built analytics, MoEngage enables hyper-personalization at scale across multiple channels like mobile push, email, in-app, web push, On-site messages, and SMS.  Fortune 500 brands across 35+ countries use MoEngage to orchestrate their cross-channel campaigns.

Founders Diaries: The stories keep getting better….

We have been enthralled with the response of the Boston start-up community.

We are hosting our next Founders Diaries event on Monday Feb 10 with Jeremy Allaire of Allaire Corp/Brightcove/Circle fame – we would love to see you there! Register to attend here.

How time flies….

It has been 3 years (!) since we launched the Founders Diaries event series, and we have been enthralled with the response of the Boston start-up community. What started as a single inspirational talk by Robin Chase from Zipcar and a data-heavy blog post from our team has become a much larger tradition, and one we have been fortunate to share with 1,000+ attendees to date.

Accomplished start-up leaders like Michael Simon from LogMeIn, Steve Papa from Endeca, Paul Sagan from Akamai, David Cancel from Drift, and a multitude of others have been extraordinarily generous in sharing their trials, tribulations, and victories on the way to building foundational Boston companies. Those gathered have shared in laughs, heart-wrenching stories (Akamai losing a co-founder to tragedy on 9/11, whose memory inspired the team for years to come), ‘wows’ (LogMeIn’s picture-perfect early growth #s in spite of early rejection from investors), and tales of culture reigning supreme (Datto’s Austin McChord wins the award for most creative in-office competitions/races). We are deeply appreciative of not only our speakers but those who come to listen, ask questions, and share their own stories over apps and drinks.

Up Next: Good things come in 3’s…

Our next distinguished speaker, Jeremy Allaire, earns the unique commendation of having started 3 (3!!) successful start-ups, displaying a relentless determination to build products, hire teams, and close customers across decades.

Jeremy started his entrepreneurial journey as Co-Founder/CTO of Allaire Corporation, where he led the company’s product and GTM strategy and helped grow the business to 1M customers, $120M+ revenue, and a sale to Macromedia in late 2000. After serving as CTO of Macromedia, he then moved into online video distribution as Founder/CEO of Brightcove (from inception through the IPO), building a $130M+ revenue company that today powers video on ~25% of the top 10k websites worldwide and receives 250M+ unique visits per month. In his latest act (we won’t dare call it final at this point!), Jeremy co-founded and serves as CEO of Circle, a crypto finance company that makes it possible for people everywhere to create and share value in a way that is affordable, open and empowering.

From web application servers to online video to crypto, Jeremy has identified and harnessed trends in a way that few can.

Empowering the next generation….

When first examining the data on ‘large exits’ ($400M+) in Boston from the past 25 years, what stood out most is how certain companies serve as fertile ground for successive entrepreneurial endeavors, similar to the ‘Paypal mafia’. The initial assessment (including valuable crowdsourced additions) highlighted Akamai (40+ alumni start-ups), Genzyme (28), and Hubspot (28) as launchpoints for entrepreneurial leaders. Jeremy’s companies similarly stand out. Allaire Corp, Brightcove, and Circle have collectively produced 33 alumni start-ups from their employee ranks (counting founders/early start-up CEOs).

A few fun facts about these alumni adventures (listed here – contributions welcome!):

-8 multiple-time entrepreneurs on the list

-6 alumni companies had 2 or more co-founders from the Allaire Corp/Brightcove/Circle mafia (‘no new friends’, as they say)

-JJ Allaire (Jeremy’s brother) co-founded Allaire Corp and has founded three subsequent companies: Onfolio, FitNow, and R-Studio

-Notable outcomes include EqualLogic ($1.4B to Dell; co-founded by Paula Long) and Imprivata (IPO then $544M sale to Thoma Bravo; Patrick Morley led as early President/CEO); both are Allaire Corp alums (Paula in engineering, Patrick on the business side)

-The group also includes a few high-potential, high-growth companies including Mux ($32M raised from YC, Accel), RStudio (millions of users, the default IDE for R, recently became a public benefit corp), Vested (an early-stage company re-imagining employee stock options), and Hummingbird (taking a new approach to RegTech, an area near/dear close to our heart)

-David Orfao served as President/CEO of Allaire Corp through its sale to Macromedia before co-founding General Catalyst, a leading VC firm; General Catalyst has funded at least 7 of the Allaire-related alumni start-ups (here’s to paying it forward!)

Alumni Start-ups: Notable Exits

 Alumni Start-ups to Watch

 

Despite all the entrepreneurial activity and success to date, we are sure to see even more in the future from those in the ‘Allaire’ mafia (we are watching you, Circle alumni, for great things)!

Join us….

We hope you’ll join us on Monday February 10th to hear Jeremy’s wisdom, and maybe even cross paths with an alumni founder! Please sign up here to attend – see you there and at future gatherings!

– Team F-Prime

Kudos to Nisha Rangarajan for key research and analysis in support of this post.

Sources: LinkedIn, Pitchbook, Crunchbase, and VentureFizz.

Retooling the Lab-Software Stack

Day-to-day software used by scientists remains stuck in the dark ages.

While great strides have been made in biomedical research over the past decade with breakthrough technologies like CRISPR and gene therapy, the day-to-day software used by scientists remains stuck in the dark ages.

On a product-level, legacy lab-software is often difficult to deploy (anyone heard of SaaS?), terrible to integrate (API still means Active Pharmaceutical Ingredient) and shockingly bad from a UI/ UX perspective (think Pong from 1972). On a functional level, it’s often unfit for modern data-types/ data-volumes and lacking in embedded intelligence (i.e. AI/ML). Software may be eating the world in other industries, but it only ever nibbled at the R&D lab.

Thankfully, over the last few years we’ve seen a new breed of start-up emerge looking to overhaul the lab-software stack. These companies are built on modern tech foundations and tend to be product-led with freemium, self-serve versions that delight users not dissuade them. Several F-Prime portfolio companies exemplify these traits: Benchling has thoroughly modernized what a Lab Operating System should look, feel and function like; Owkin is empowering scientists to create predictive models for drug efficacy; and BenchSci (our newest investment) has mapped the world’s biomedical research to improve the efficiency of reagent selection and experiment design.

The DNA of this new breed of start-ups is also fundamentally different. They’re demographically younger (born in the web). They’re educational ‘dual-citizens’ (fluent in Biological Sciences and Computer Science). And they bring a healthy disregard for incumbent vendors in the R&D market (they’re “in the world, but not of it”).

The challenge of commercializing biomedical research is well understood by everyone involved (e.g., high profile clinical failures, experimental irreproducibility and escalating costs of drug development). While better lab software is clearly not THE answer, it is AN answer. It’s an exciting time to be building a company in this vertical and if you’re doing so, we’d love to hear from you.

BenchSci

BenchSci is a software platform that maps disease biology using machine learning models trained on 20+ million scientific publications. Its proprietary ASCEND™ platform helps scientists design better experiments, uncover novel insights, and identify safety and efficacy risks earlier in the discovery process.

Funnel

Funnel’s product is a Data Core used by 800 forward-thinking organizations across a wide set of industry verticals to automatically import marketing data and make it Business-Ready. The Swedish Software-as-a-Service (SaaS) company was founded by Fredrik Skantze and Per Made in 2014. Funnel has 140 employees and offices in Stockholm and Boston.

Snapdocs

Founded in 2013, Snapdocs is the industry’s leading digital closing platform. With its patented AI technology, Snapdocs is on a mission to perfect mortgage closings and transform a $2 trillion pillar of the U.S. economy. Powering over 750,000 closings a year, Snapdocs is leading the charge to modernize, streamline, and improve the mortgage process for lenders, borrowers, and settlement. Snapdocs is the only solution with a proven track record of creating a single, scalable process for every closing, whether wet, hybrid, or digital. Every day, over 50,000 mortgage professionals rely on Snapdocs’ technology to automate manual work and digitize paper processes that plague the industry. Snapdocs is a rapidly growing San Francisco based real estate technology company backed by prestigious Silicon Valley blue-chip venture capital funds, like Y Combinator, SV Angel, Sequoia Capital, and F-Prime.

Vendr

Vendr is an end-to-end SaaS purchasing & renewal management platform. They manage your software purchases and renewals, so you can manage your business. Vendr was acquired by Vertice in 2026.

Logixboard

Logixboard is the digital partner for freight forwarders to succeed in today’s highly competitive market. Our web-based platform empowers freight forwarders to do their work more efficiently, increasing customer satisfaction, and unlock the power of their data. Logixboard is a recent graduate of Techstars and is based in Seattle with offices in Bogota, Colombia.