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Why did file sharing drive so much startup innovation?
One of the great things about editing all of our deep-dive EC-1 startup profiles is that you start to notice patterns across successful companies. While origin stories and trajectories can vary widely, the best companies seem to come from similar places and are conceived around very peculiar themes.
To wit, one common theme that came from our recent profiles of Expensify and NS1 is the centrality of file sharing (or, illegal file sharing if you are on that side of the fence) and internet infrastructure in the origin stories of the two companies. That’s peculiar, because the duo honestly couldn’t be more different. Expensify is an SF-founded (now Portland-based), decentralized startup focused on building expense reporting and analytics software for companies and CFOs. New York-based NS1 designs highly redundant DNS and internet traffic performance tools for web applications.
Yet, take a look at how the two companies were founded. Anna Heim on the origins of Expensify:
To truly understand Expensify, you first need to take a close look at a unique, short-lived, P2P file-sharing company called Red Swoosh, which was Travis Kalanick’s startup before he founded Uber. Framed by Kalanick as his “revenge business” after his previous P2P startup Scour was sued into oblivion for copyright infringement, Red Swoosh would be the precursor for Expensify’s future culture and ethos. In fact, many of Expensify’s initial team actually met at Red Swoosh, which was eventually acquired by Akamai Technologies in 2007 for $18.7 million.
[Expensify founder and CEO David] Barrett, a self-proclaimed alpha geek and lifelong software engineer, was actually Red Swoosh’s last engineering manager, hired after the failure of his first project, iGlance.com, a P2P push-to-talk program that couldn’t compete against Skype. “While I was licking my wounds from that experience, I was approached by Travis Kalanick who was running a startup called Red Swoosh,” he recalled in an interview.
Then you head over to Sean Michael Kerner’s story on how NS1 came together:
NS1’s story begins back at the turn of the millennium, when [NS1 co-founder and CEO Kris] Beevers was an undergrad at Rensselaer Polytechnic Institute (RPI) in upstate New York and found himself employed at a small file-sharing startup called Aimster with some friends from RPI. Aimster was his first taste of life at an internet startup in the heady days of the dot-com boom and bust, and also where he met an enterprising young engineer by the name of Raj Dutt, who would become a key relationship over the next two decades.
By 2007, Beevers had completed his Ph.D. in robotic mapping at RPI and tried his hand at co-founding and running an engineered-wood-product company named SolidJoint Research, Inc. for 10 months. But he soon boomeranged back to the internet world, joining some of his former co-workers from Aimster at a company called Voxel that had been founded by Dutt.
The startup provided a cornucopia of services including basic web hosting, server co-location, content delivery and DNS services. “Voxel was one of those companies where you learn a lot because you’re doing way more than you rightfully should,” Beevers said. “It was a business sort of built out of love for the tech, and love for solving problems.”
The New York City-based company peaked at some 60 employees before it was acquired in December 2011 by Internap Network Services for $35 million.
Note some of the similarities here. First, these wildly different founders ended up both working on key internet plumbing. Which makes sense of course, since two decades ago, building out the networking and compute capacity of the internet was one of the major engineering challenges of that period in the web’s history.
Additionally in both cases, the founding teams met at little-known companies defined by their engineering cultures and which sold to larger internet infrastructure conglomerates for relatively small amounts of money. And those acquirers ended up being laboratories for all kinds of innovation, even as few people really remember Akamai or Internap these days (both companies are still around today mind you).
The cohort of founders is fascinating. Obviously, you have Travis Kalanick, who would later go on to found Uber. But the Voxel network that went to Internap is hardly a slouch:
Dutt would leave Internap to start Grafana, an open-source data visualization vendor that has raised over $75 million to date. Voxel COO Zachary Smith went on to found bare metal cloud provider, Packet, in 2013, which he ran as CEO until the company was acquired by Equinix in March 2020 for $335 million. Meanwhile, Justin Biegel, who spent time at Voxel in operations, has raised nearly $62 million for his startup Kentik. And of course, NS1 was birthed from the same alumni network.
What’s interesting to me with these two companies (and some others in our set of stories) is how often founders worked on other problems before starting the companies that would make them famous. They learned the trade, built networks of hyperintelligent present and future colleagues, understood business development and growth, and started to create a flywheel of innovation amidst their friends. They also got a taste of an exit without really getting the whole meal, if you will.
In particular with file sharing, what’s interesting is the rebellious and democratic ethos that came with that world back at the turn of the millennium. To work in file sharing in that era meant fighting the big music labels, overturning the economics of entire industries, and breaking down barriers to allow the internet economy to flourish. It attracted a weird bunch of folks — the exact kind of weirdness that happens to make good startup founders, apparently. It echos one of the key arguments of Fred Turner’s book, “From Counterculture to Cyberculture.”
Which begs the question then: What are the “file-sharing” markets today that these sorts of individuals congregate around? One that seems obvious to me is blockchain, which has precisely that balance of rebelliousness, democratization and technical excellence. (Well, at least some of the time!) And then there are the modern-day “pirates” today such as Alexandra Elbakyan who invented and has operated Sci-Hub to make the world’s research and knowledge democratized.
It’s maybe not the current batch of companies that we see that will become the next extraordinary unicorns. But watch the people who show up in the interesting places — because their next projects often seem to hit gold.
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Extra Crunch roundup: Guest posts wanted, ‘mango’ seed rounds, Expensify’s tech stack
Prospective contributors regularly ask us about which topics Extra Crunch subscribers would like to hear more about, and the answer is always the same:
- Actionable advice that is backed up by data and/or experience.
- Strategic insights that go beyond best practices and offer specific recommendations readers can try out for themselves.
- Industry analysis that paints a clear picture of the companies, products and services that characterize individual tech sectors.
Our submission guidelines haven’t changed, but Managing Editor Eric Eldon and I wrote a short post that identifies the topics we’re prioritizing at the moment:
- How-to articles for early-stage founders.
- Market analysis of different tech sectors.
- Growth marketing strategies.
- Alternative fundraising.
- Quality of life (personal health, sustainability, proptech, transportation).
If you’re a skillful entrepreneur, founder or investor who’s interested in helping someone else build their business, please read our latest guidelines, then send your ideas to guestcolumns@techcrunch.com.
Thanks for reading; I hope you have a great weekend.
Walter Thompson
Senior Editor, TechCrunch
@yourprotagonist
Full Extra Crunch articles are only available to members
Use discount code ECFriday to save 20% off a one- or two-year subscription
Opting for a debt round can take you from Series A startup to Series B unicorn
Image Credits: olegkalina (opens in a new window) / Getty Images
Debt is a tool, and like any other — be it a hammer or handsaw — it’s extremely valuable when used skillfully but can cause a lot of pain when mismanaged. This is a story about how it can go right.
Mario Ciabarra, the founder and CEO of Quantum Metric, breaks down how his company was on a “tremendous growth curve” — and then the pandemic hit.
“As the weeks following the initial shelter-in-place orders ticked by, the rush toward digital grew exponentially, and opportunities to secure new customers started piling up,” Ciabarra writes. “A solution to our money problems, perhaps? Not so fast — it was a classic case of needing to spend in order to make.”
If companies want to preserve equity, debt can be an advantageous choice. Here’s how Quantum Metric did it.
4 proven approaches to CX strategy that make customers feel loved
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People have been working to optimize customer experiences (CX) since we began selling things to each other.
A famous San Francisco bakery has an exhaust fan at street level; each morning, its neighbors awake to the scent of orange-cinnamon morning buns wafting down the block. Similarly, savvy hairstylists know to greet returning customers by asking if they want a repeat or something new.
Online, CX may encompass anything from recommending the right shoes to AI that knows when to send a frustrated traveler an upgrade for a delayed flight.
In light of Qualtrics’ spinout and IPO and Sprinklr’s recent S-1, Rebecca Liu-Doyle, principal at Insight Partners, describes four key attributes shared by “companies that have upped their CX game.”
Twitter’s acquisition strategy: Eat the public conversation
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What is a microblogging service doing buying a social podcasting company and a newsletter tool while also building a live broadcasting sub-app? Is there even a strategy at all?
Yes. Twitter is trying to revitalize itself by adding more contexts for discourse to its repertoire. The result, if everything goes right, will be an influence superapp that hasn’t existed anywhere before. The alternative is nothing less than the destruction of Twitter into a link-forwarding service.
Let’s talk about how Twitter is trying to eat the public conversation.
Reading the IPO market’s tea leaves
Image Credits: Nigel Sussman (opens in a new window)
Although it was a truncated holiday week here in the United States, there was a bushel of IPO news. We sorted through the updates and came up with a series of sentiment calls regarding these public offerings.
Earlier this week, we took a look at:
- Marqeta‘s first IPO price range (fintech).
- 1st Dibs‘ first IPO price range (e-commerce).
- Zeta Global‘s IPO pricing (martech).
- The start of SoFi trading post-SPAC (fintech).
- The latest from BarkBox (e-commerce).
How Expensify hacked its way to a robust, scalable tech stack
Image Credits: Nigel Sussman
Part 4 of Expensify’s EC-1 digs into the company’s engineering and technology, with Anna Heim noting that the group of P2P pirates/hackers set out to build an expense management app by sticking to their gut and making their own rules.
They asked questions few considered, like: Why have lots of employees when you can find a way to get work done and reach impressive profitability with a few? Why work from an office in San Francisco when the internet lets you work from anywhere, even a sailboat in the Caribbean?
It makes sense in a way: If you’re a pirate, to hell with the rules, right?
With that in mind, one could assume Expensify decided to ask itself: Why not build our own totally custom tech stack?
Indeed, Expensify has made several tech decisions that were met with disbelief, but its belief in its own choices has paid off over the years, and the company is ready to IPO any day now.
How much of a tech advantage Expensify enjoys owing to such choices is an open question, but one thing is clear: These choices are key to understanding Expensify and its roadmap. Let’s take a look.
Etsy asks, ‘How do you do, fellow kids?’ with $1.6B Depop purchase
Image Credits: Getty Images
The news this week that e-commerce marketplace Etsy will buy Depop, a startup that provides a secondhand e-commerce marketplace, for more than $1.6 billion may not have made a large impact on the acquiring company’s share price thus far, but it provides a fascinating look into what brands may be willing to pay for access to the Gen Z market.
Etsy is buying Gen Z love. Think about it — Gen Z is probably not the first demographic that comes to mind when you consider Etsy, so you can see why the deal may pencil out in the larger company’s mind.
But it isn’t cheap. The lesson from the Etsy-Depop deal appears to be that large e-commerce players are willing to splash out for youth-approved marketplaces. That’s good news for yet-private companies that are popular with the budding generation.
Confluent’s IPO brings a high-growth, high-burn SaaS model to the public markets
Image Credits: Andriy Onufriyenko / Getty Images
Confluent became the latest company to announce its intent to take the IPO route, officially filing its S-1 paperwork this week.
The company, which has raised over $455 million since it launched in 2014, was most recently valued at just over $4.5 billion when it raised $250 million last April.
What does Confluent do? It built a streaming data platform on top of the open-source Apache Kafka project. In addition to its open-source roots, Confluent has a free tier of its commercial cloud offering to complement its paid products, helping generate top-of-funnel inflows that it converts to sales.
What we can see in Confluent is nearly an old-school, high-burn SaaS business. It has taken on oodles of capital and used it in an increasingly expensive sales model.
How to win consulting, board and deal roles with PE and VC funds
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Would you like to work with private equity and venture capital funds?
There are relatively few jobs directly inside private equity and venture capital funds, and those jobs are highly competitive.
However, there are many other ways you can work and earn money within the industry — as a consultant, an interim executive, a board member, a deal executive partnering to buy a company, an executive in residence or as an entrepreneur in residence.
Let’s take a look at the different ways you can work with the investment community.
The existential cost of decelerated growth
Image Credits: Nigel Sussman (opens in a new window)
Even among the most valuable tech shops, shareholder return is concentrated in share price appreciation, and buybacks, which is the same thing to a degree.
Slowly growing tech companies worth single-digit billions can’t play the buyback game to the same degree as the majors. And they are growing more slowly, so even a similar buyback program in relative scale would excite less.
Grow or die, in other words. Or at least grow or come under heavy fire from external investors who want to oust the founder-CEO and “reform” the company. But if you can grow quickly, welcome to the land of milk and honey.
Even among the most valuable tech shops, shareholder return is concentrated in share price appreciation, and buybacks, which is the same thing to a degree.
Slowly growing tech companies worth single-digit billions can’t play the buyback game to the same degree as the majors. And they are growing more slowly, so even a similar buyback program in relative scale would excite less.
Grow or die, in other words. Or at least grow or come under heavy fire from external investors who want to oust the founder-CEO and “reform” the company. But if you can grow quickly, welcome to the land of milk and honey.
Hormonal health is a massive opportunity: Where are the unicorns?
Image Credits: Carol Yepes (opens in a new window) / Getty Images
There is a growing group of entrepreneurs who are betting that hormonal health is the key wedge into the digital health boom.
Hormones are fluctuating, ever-evolving, and diverse — but these founders say they’re also key to solving many health conditions that disproportionately impact women, from diabetes to infertility to mental health challenges.
Many believe it’s that complexity that underscores the opportunity. Hormonal health sits at the center of conversations around personalized medicine and women’s health: By 2025, women’s health could be a $50 billion industry, and by 2026, digital health more broadly is estimated to hit $221 billion.
Still, as funding for women’s health startups drops and stigma continues to impact where venture dollars go, it’s unclear whether the sector will remain in its infancy or hit a true inflection point.
3 lessons we learned after raising $6.3M from 50 investors
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Two years ago, founders of calendar assistant platform Reclaim were looking for a “mango” seed round — a boodle of cash large enough to help them transition from the prototype phase to staffing up for a public launch.
Although the team received offers, co-founder Henry Shapiro says the few that materialized were poor options, partially because Reclaim was still pre-product.
“So one summer morning, my co-founder and I sat down in his garage — where we’d been prototyping, pitching and iterating for the past year — and realized that as hard as it was, we would have to walk away entirely and do a full reset on our fundraising strategy,” he writes.
Shapiro shares what he learned from embracing failure and offers three conclusions “every founder should consider before they decide to go out and pitch investors.”
For SaaS startups, differentiation is an iterative process
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Although software as a service has been thriving as a sector for years, it has gone into overdrive in the past year as businesses responded to the pandemic by speeding up the migration of important functions to the cloud, ActiveCampaign founder and CEO Jason VandeBoom writes in a guest column.
“We’ve all seen the news of SaaS startups raising large funding rounds, with deal sizes and valuations steadily climbing. But as tech industry watchers know only too well, large funding rounds and valuations are not foolproof indicators of sustainable growth and longevity.”
VandeBoom notes that to scale sustainably, SaaS startups need to “stand apart from the herd at every phase of development. Failure to do so means a poor outcome for founders and investors.”
“As a founder who pivoted from on-premise to SaaS back in 2016, I have focused on scaling my company (most recently crossing 145,000 customers) and in the process, learned quite a bit about making a mark,” VandeBoom writes. “Here is some advice on differentiation at the various stages in the life of a SaaS startup.”
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How Expensify hacked its way to a robust, scalable tech stack
Take a close look at any ambitious startup and you’ll find pugnacity nestled in its core. Stubbornness and a bullheaded belief in the worth of what a company wants to bring to fruition is often the biggest driver of its success, and the people at such companies also tend to share this quality.
So it wouldn’t be too far off the mark to say the people at Expensify are a stubborn lot — to the company’s ultimate benefit. This group of P2P pirates/hackers that set out to build an expense management app stuck to their gut, made their own rules. They asked questions few thought of, like: Why have lots of employees when you can find a way to get work done and reach impressive profitability with a few? Why work from an office in San Francisco when the internet lets you work from anywhere, even a sailboat in the Caribbean?
It makes sense in a way: If you’re a pirate, to hell with the rules, right? And even more so when nobody can explain the rules in the first place.
With that in mind, one could assume Expensify decided to ask itself: Why not build our own totally custom tech stack? Indeed, Expensify has made several tech decisions that were met with disbelief — from having an open-source frontend and cross-platform mobile development to hiring contractors to train its AI and recruiting open-source contributors — but its belief in its own choices has paid off over the years, and the company is ready to IPO any day now.
How much of a tech advantage Expensify enjoys owing to such choices is an open question, but one thing is clear: These choices are key to understanding Expensify and its roadmap. Let’s take a look.
Built on Bedrock
I think another question Expensify also decided to ask in its early days was something like: Why not have our database on top of a technology that’s built for small-scale application software?
It may sound incredible, but Expensify actually runs on a custom database built on top of SQLite. This is surprising, because despite being one of the most widely deployed database engines, SQLite is known for running on small, embedded systems like smartphones and web browsers, not powering enterprise-scale databases.
It may sound incredible, but Expensify actually runs on a custom database built on top of SQLite.
This custom database is called Bedrock, and its architecture is as unique as they come. Expensify explains it as an “RDBMS optimized for self-healing replication across relatively slow, relatively unreliable WAN (internet) connections, enabling extremely high availability/high performance multi-datacenter deployments without any single point of failure.” RDBMS means relational database management system, describing SQLite and other row-based databases where entries are interconnected with each other.
But why would Expensify build this instead of going for any number of widely available enterprise database solutions?
To answer that question, we need to go back to the early days of the company, which was originally a side project for its founder and CEO, David Barrett. His initial idea was to develop a prepaid card for the homeless, but this required putting a server on the Visa network, which brought several strict requirements and challenges. “I would say one of the most difficult [parts] was that I needed the ability to automatically replicate and failover,” Barrett told TechCrunch when we interviewed him a couple of months ago.
This was no easy feat in 2007, but Barrett was up for the challenge. “I just hit a moment where the technology available off the shelf just wasn’t that good. And I happened to be a peer-to-peer software developer who had tons of spare time and really wanted to build this thing to put on the Visa backend,” he said. The P2P aspect was important, as Barrett had the skills to make it work. His first hires for Expensify, P2P engineers he had worked with at Red Swoosh and Akamai, were also unusually suited for the job.
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Extra Crunch roundup: Lordstown Motors’ woes, how co-CEOs work, Brian Chesky interview
Lordstown Motors released its Q1 earnings yesterday, and the electric vehicle manufacturer is facing a few challenges.
Expenses were higher than expected, it plans to slash production by about 50%, and the company reported zero revenue and a net loss of $125 million. Oh, it also needs more capital.
“But there’s more to the Lordstown mess than merely a single bad quarter,” writes Alex Wilhelm. “Lordstown’s earnings mess and the resulting dissonance with its own predictions are notable on their own, but they also point to what could be shifting sentiment regarding SPAC combinations.”
In light of the company’s lackluster earnings report (and a pending SEC investigation), Alex unpacks the company’s Q1, “but don’t think that we’re only singling out one company; others fit the bill, and more will in time.”
May 27 Clubhouse chat: How to ensure data quality in the era of Big Data
Image Credits: TechCrunch
Join TechCrunch reporter Ron Miller and Patrik Liu Tran, co-founder and CEO of automated real-time data validation and quality monitoring platform Validio, on Thursday, May 27 at 9 a.m. PDT/noon EDT for a Clubhouse chat about ensuring data quality in the era of Big Data.
The world produces 2.5 quintillion bytes of data daily, but modern data infrastructure still lacks solutions for monitoring data quality and data validation.
Among other topics, they’ll discuss the build versus buy debate, how to better understand data failures, and why traditional methods for identifying data failures are no longer operational.
Click here to join the conversation.
Thanks very much for reading Extra Crunch; have a great week!
Walter Thompson
Senior Editor, TechCrunch
@yourprotagonist
Full Extra Crunch articles are only available to members.
Use discount code ECFriday to save 20% off a one- or two-year subscription.
How Expensify shed Silicon Valley arrogance to realize its global ambitions
Image Credits: Nigel Sussman
Expensify may be the most ambitious software company ever to mostly abandon the Bay Area as the center of its operations.
The startup’s history is tied to places representative of San Francisco: The founding team worked out of Peet’s Coffee on Mission Street for a few months, then crashed at a penthouse lounge near the 4th and King Caltrain station, followed by a tiny office and then a slightly bigger one in the Flatiron building near Market Street.
Thirteen years later, Expensify still has an office a few blocks away on Kearny Street, but it’s no longer a San Francisco company or even a Silicon Valley firm. The company is truly global with employees across the world — and it did that before COVID-19 made remote working cool.
It makes sense that a company founded by internet pirates would let its workforce live anywhere they please and however they want to. Yet, how does it manage to make it all work well enough to reach $100 million in annual revenue with just a tad more than 100 employees?
As I described in Part 2 of this EC-1, that staffing efficiency is partly due to its culture and who it hires. It’s also because it has attracted top talent from across the world by giving them benefits like the option to work remotely all year as well as paying SF-level salaries even to those not based in the tech hub. It’s also got annual fully paid month-long “workcations” for every employee, their partner and kids.
Brian Chesky describes a faster, nimbler post-pandemic Airbnb
Image Credits: TechCrunch
Managing Editor Jordan Crook interviewed Airbnb co-founder and CEO Brian Chesky to discuss the future of travel and what it was like leading the world’s biggest hospitality startup during a global pandemic.
“Our business initially dropped 80% in eight weeks. I say it’s like driving a car. You can’t go 80 miles an hour, slam on the brakes, and expect nothing really bad to happen.
Now imagine you’re going 80 miles an hour, slam on the brakes, then rebuild the car kind of while still moving, and then try to accelerate into an IPO, all on Zoom.”
Embedded finance will help fill the life insurance coverage gap
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There’s latent demand for life insurance currently unaddressed by much of the financial services industry, and embedded finance can be the solution.
It’s imperative for companies to consider product lines and partnerships to expand markets, create new revenue streams and provide added value to their customers.
Connecting consumers with products they need through channels they already know and trust is both a massive revenue opportunity and a social good, providing financial resilience to families at a time when they need it most.
Zeta Global’s IPO filing uncovers modest growth, strong adjusted profitability
Image Credits: Nigel Sussman (opens in a new window)
Zeta Global raised north of $600 million in private capital in the form of both equity financing and debt, making it a unicorn worth understanding.
The gist is that Zeta ingests and crunches lots of data, helping its users market to their customers on a targeted basis throughout their individual buying lifecycles. In simpler terms, Zeta helps companies pitch customers in varied manners depending on their own characteristics.
You can imagine that, as the digital economy has grown, the sort of work Zeta Global supports has only expanded. So, has Zeta itself grown quickly? And does it have an attractive business profile? We want to know.
5 predictions for the future of e-commerce
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In 2016, more than 20 years after Amazon’s founding and 10 years since Shopify launched, it would have been easy to assume e-commerce penetration (the percentage of total retail spend where the goods were bought and sold online) would be over 50%.
But what we found was shocking: The U.S. was only approximately 8% penetrated — only 8% for arguably the most advanced economy in the world!
Despite e-commerce growth skyrocketing over the past year, the reality is the U.S. has still only reached an e-commerce penetration rate of around 17%. During the last 18 months, we’ve closed the gap to South Korea and China’s e-commerce penetration of more than 25%, but there is still much progress to be made.
Here are five key predictions for what this road to further penetration will hold.
Develop a buyer’s guide to educate your startup’s sales team and customers
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Every company wants to be innovative, but innovation comes with its share of difficulties. One key challenge for early-stage companies that are disrupting a particular space or creating a new category is figuring out how to sell a unique product to customers who have never bought such a solution.
This is especially the case when a solution doesn’t have many reference points and its significance may not be obvious.
Some buyers could use a walkthrough of the buying process. If you are building a singular product in a nascent market that necessitates forward-looking customers and want to drastically shorten sales cycles, create a buyer’s guide.
When to walk away from a VC who wants to invest in your startup
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Pay attention to red flags when meeting with VCs: If they cancel late or leave you waiting, it’s a sign, just like being asked generic questions that demonstrate little or no understanding of the proposition. If they critique you or your business, that’s fine (obviously), but make sure you find out what’s behind their assertions to judge how well informed they are.
If you’re going to face these people each month and debate the direction of your business, the least you can expect is a robust argument outlining precisely why you may not have all the right answers.
If you fail to spot the warning signs, you’ll live to regret it. But do your due diligence and work constructively with them and, together, you might actually build a sustainable future.
Deep Science: Robots, meet world
Image via Getty Images / Westend61
This column aims to collect some of the most relevant recent discoveries and papers — particularly in, but not limited to, artificial intelligence — and explain why they matter.
In this edition, we have a lot of items concerned with the interface between AI or robotics and the real world. Of course, most applications of this type of technology have real-world applications, but specifically, this research is about the inevitable difficulties that occur due to limitations on either side of the real-virtual divide.
2 CEOs are better than 1
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Netflix has two CEOs: Co-founder Reed Hastings oversees the streaming side of the company, while Ted Sarandos guides Netflix’s content.
Warby Parker has co-CEOs as well — its co-founders went to college together. Other companies like the tech giant Oracle and luggage maker Away have shifted from having co-CEOs in recent years, sparking a wave of headlines suggesting that the model is broken.
While there isn’t a lot of research on companies with multiple CEOs, the data is more promising than the headlines would suggest. One study on public companies with co-CEOs revealed that the average tenure for co-CEOs, about 4.5 years, was comparable to solitary CEOs, “suggesting that this arrangement is more stable than previously believed.”
Furthermore, it’s impossible to be in two places at once or clone yourself. With co-CEOs, you can effectively do just that.
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How Expensify shed Silicon Valley arrogance to realize its global ambitions
Expensify may be the most ambitious software company ever to mostly abandon the Bay Area as the center of its operations.
Expensify may be the most ambitious software company ever to mostly abandon the Bay Area as the center of its operations.
The startup’s history is tied to places representative of San Francisco: The founding team worked out of Peet’s Coffee on Mission Street for a few months, then crashed at a penthouse lounge near the 4th and King Caltrain station, followed by a tiny office and then a slightly bigger one in the Flatiron building near Market Street.
Thirteen years later, Expensify still has an office a few blocks away on Kearny Street, but it’s no longer a San Francisco company or even a Silicon Valley firm. The company is truly global with employees across the world — and it did that before COVID-19 made remote working cool.
“Things got so much better when we stopped viewing ourselves as a Silicon Valley company. We basically said, no, we’re just a global company,” CEO David Barrett told TechCrunch. That globalism led to it opening a major office in — of all places —a small town in rural Michigan. That Ironwood expansion would eventually lead to a cultural makeover that would see the company broadly abandon its focus on the Bay Area, expanding from a headquarters in Portland to offices around the globe.
It makes sense that a company founded by internet pirates would let its workforce live anywhere they please and however they want to. Yet, how does it manage to make it all work well enough to reach $100 million in annual revenue with just a tad more than 100 employees?
As I described in Part 2 of this EC-1, that staffing efficiency is partly due to its culture and who it hires. It’s also because it has attracted top talent from across the world by giving them benefits like the option to work remotely all year as well as paying SF-level salaries even to those not based in the tech hub. It’s also got annual fully paid month-long “workcations” for every employee, their partner and kids.
Yet the real story is how a company can become untethered from its original geography, willing to adapt to new places and new cultures, and ultimately, give up the past while building the future.
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How Expensify got to $100M in revenue by hiring “stem cells” and not “cogs in a wheel”
The influence of a founder on their company’s culture cannot be overstated. Everything from their views on the product and business to how they think about people affects how their company’s employees will behave, and since behavior in turn informs culture, the consequences of a founder’s early decisions can be far-reaching.
So it’s not very surprising that Expensify has its own take on almost everything it does when you consider what its founder and CEO David Barrett learned early in his life: “Basically everyone is wrong about basically everything.” As we saw in part 1 of this EC-1, this led him to the revelation that it’s easier to figure things out for yourself than finding advice that applies to you. Eventually, these insights — and the adventurous P2P hacker attitude he nurtured alongside his colleagues and Travis Kalanick at Red Swoosh — would inform how he would go about shaping Expensify.
Expensify’s culture can’t be separated from its hiring and growth processes — by joining the company, employees self-select into a group that isn’t likely to get hung up about trade-offs.
It’s striking how Expensify has managed to maintain this character 13 years later, even on the threshold of an IPO. How did this happen? During a series of interviews in February and early March, we found the answer is tied to the level of thought and effort this expense management business puts into its culture.
You see, the people at Expensify are prepared to invent their own playbook, develop it and, if needed, rewrite it completely. Its HR policies and strategy are tailored to find people who would have fun building an expense management product. It has a unique growth and recognition scheme to offset the drawbacks of a flat organizational structure. It’s even got a “Senate” that vets all major decisions. No kidding.
All this, and more, has ultimately helped Expensify reach more than 10 million users and achieve $100 million in annual revenue with just 130 employees. Let’s take a closer look at how Expensify makes it happen.
“We want the fewest people necessary to get the job done”
It’s clear Expensify’s unusually high employee-to-revenue ratio is intentional: “We want the fewest people necessary to get the job done,” Barrett says. But how do you actually achieve it? How do you hire and keep people who can deliver such results? Barrett had to learn how the hard way.
Expensify’s first team was based in San Francisco and comprised Barrett’s old Red Swoosh and Akamai colleagues, who joined a few months after Akamai fired him. A small team was enough to get started, but it was much more difficult to hire additional people. Barrett is eager to clarify the Valley is not really the best place to recruit talent: “Sure, Silicon Valley has a ton of really awesome people, but all of them have jobs!,” he says.
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Extra Crunch roundup: Selling SaaS to developers, cracking YC after 13 tries, all about Expensify
Before Twilio had a market cap approaching $56 billion and more than 200,000 customers, the cloud-communications platform developed a secret sauce to fuel its growth: a developer-focused model that dispensed with traditional marketing rules.
Software companies that sell directly to end users share a simple framework for managing growth that leverages discoverability, desirability and do-ability — the “aha!” moment where a consumer is able to incorporate a new product into their workflow.
Data show that traditional marketing doesn’t work on developers, and it’s not because they’re impervious to a sales pitch. Builders just want reliable tools that are easy to use.
As a result, companies that are looking to create and sell software to developers at scale must toss their B2B playbooks and meet their customers where they are.
Attorney Sophie Alcorn, our in-house immigration law expert, submitted two columns: On Monday, she analyzed a decision by the U.S. Department of Homeland Security not to cancel the International Entrepreneur Parole program, which potentially allows founders from other countries to stay in the U.S. for as long as 60 months.
On Wednesday, she responded to a question from an entrepreneur who asked whether it made sense to sponsor visas for workers who are working remotely inside the U.S.
Thanks very much for reading Extra Crunch this week, and have a great weekend.
Walter Thompson
Senior Editor, TechCrunch
@yourprotagonist
4 lessons I learned about getting into Y Combinator (after 13 applications)
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Can you imagine making 13 attempts at something before attaining a successful outcome?
Alex Circei, CEO and co-founder of Git analytics tool Waydev, applied 13 times to Y Combinator before his team was accepted. Each year, the accelerator admits only about 5% of the startups that seek to join.
“Competition may be fierce, but it’s not impossible,” says Circei. “Jumping through some hoops is not only worth the potential payoff but is ultimately a valuable learning curve for any startup.”
In an exclusive exposé for TechCrunch, he shares four key lessons he learned while steering his startup through YC’s stringent selection process.
The first? “Put your business value before your personal vanity.”
The Expensify EC-1
Image Credits: Illustration by Nigel Sussman, art design by Bryce Durbin
In March, TechCrunch Daily Reporter Anna Heim was interviewing executives at Expensify to learn more about the company’s history and operations when they unexpectedly made themselves less available.
Our suspicions about their change of heart were confirmed on May 3 when the expense report management company confidentially filed to go public.
With a founding team comprised mainly of P2P hackers, it’s perhaps inevitable that Expensify doesn’t look and feel like something an MBA might envision.
“We hire in a super different way. We have a very unusual internal management structure,” said founder and CEO David Barrett. “Our business model itself is very unusual. We don’t have any salespeople, for example.”
Similar to the way companies must file a Form S-1 that describes their operations and how they plan to spend capital, TechCrunch EC-1s are part origin story, part X-ray. We published the first article in a series on Expensify on Monday:
- “How a band of P2P hackers planted the seeds of a unique expense management giant” (2,400 words/10 minutes) — Explores the founders’ days with a P2P content distribution startup called Red Swoosh (Travis Kalanick’s venture before Uber) and how that experience influenced Expensify’s development.
We’ll publish the remainder of Anna’s series on Expensify in the coming weeks, so stay tuned.
As Procore looks to nearly double its private valuation, the IPO market shows signs of life
Image Credits: Nigel Sussman (opens in a new window)
Construction tech unicorn Procore Technologies this week set a price range for its impending public offering. The news comes after the company initially filed to go public in February of 2020, a move delayed by the pandemic.
In March 2021, Procore filed again for a public offering, but its second shot ran into a cooling IPO market. The company filed another S-1/A in April, and then another in early May. This week’s filing is the first that sets a price for the Carpinteria, California-based software upstart.
But Procore is not the only company that filed and later put on hold an IPO to get back to work on floating. Kaltura, a software company focused on video distribution, also recently got its IPO back on track. Are we seeing a reacceleration of the IPO market? Perhaps.
3 golden rules for health tech entrepreneurs
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Family physician Bobbie Kumar lays out the golden rules to ensure your healthcare product, service or innovation is on the right track.
Rule 1: “It’s not enough to develop a ‘new tool’ to use in a health setting,” Dr. Kumar writes. “Maybe it has a purpose, but does it meaningfully address a need, or solve a problem, in a way that measurably improves outcomes? In other words: Does it have value?”
Dear Sophie: How does the International Entrepreneur Parole program work?
Image Credits: Bryce Durbin/TechCrunch
Dear Sophie,
I’m the founder of an early-stage, two-year-old fintech startup. We really want to move to San Francisco to be near our lead investor.
I heard International Entrepreneur Parole is back. What is it, and how can I apply?
— Joyous in Johannesburg
Digging into digital mortgage lender Better.com’s huge SPAC
Image Credits: Nigel Sussman (opens in a new window)
If you have heard of Better.com but really had no idea what it does before this moment, welcome to the club. Mortgage tech is like pre-kindergarten applications — it applies to a very specific set of folks at a very particular moment. And they care a lot about it. But the rest of us aren’t really aware of its existence.
Better.com, a venture-backed digital mortgage lender, announced this week that it will combine with a SPAC, taking itself public in the second half of 2021. The unicorn’s news comes as the American IPO market is showing signs of fresh life after a modest April.
As tech offices begin to reopen, the workplace could look very different
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The pandemic forced many employees to begin working from home, and, in doing so, may have changed the way we think about work. While some businesses have slowly returned to the office, depending on where you live and what you do, many information workers remain at home.
That could change in the coming months as more people get vaccinated and the infection rate begins to drop in the U.S.
Many companies have discovered that their employees work just fine at home. And some workers don’t want to waste time stuck on congested highways or public transportation now that they’ve learned to work remotely. But other employees suffered in small spaces or with constant interruptions from family. Those folks may long to go back to the office.
On balance, it seems clear that whatever happens, for many companies, we probably aren’t going back whole-cloth to the prior model of commuting into the office five days a week.
For unicorns, how much does the route to going public really matter?
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On a recent episode of TechCrunch’s Equity podcast, hosts Natasha Mascarenhas and Alex Wilhelm invited Yext CFO Steve Cakebread and Latch CFO Garth Mitchell on to discuss when companies should go public, the costs and benefits of the process and when a SPAC can make sense. Yext pursued a traditional IPO a few years back; Latch is now going public via a blank-check company combination.
The chat was more than illustrative, as we got to hear two CFOs share their views on delayed public offerings and when different types of debuts can make the most sense. While the TechCrunch crew has, at times, made light of certain SPAC-led deals, the pair argued that the transactions can make good sense.
Undergirding the conversation was Cakebread’s recent IPO-focused book, which not only posited that companies going public earlier rather than later is good for their internal operations but also because it can provide the public with a chance to participate in a company’s success.
In today’s hypercharged private markets and frothy public domain, his argument is worth considering.
The truth about SDK integrations and their impact on developers
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Ken Harlan, the founder and CEO of Mobile Fuse, writes about the perks and pitfalls of software development kits.
“The digital media industry often talks about how much influence, dominance and power entities like Google and Facebook have,” Harlan writes. “Generally, the focus is on the vast troves of data and audience reach these companies tout. However, there’s more beneath the surface that strengthens the grip these companies have on both app developers and publishers alike.
“In reality, SDK integrations are a critical component of why these monolith companies have such a prominent presence.”
Don’t hate on low-code and no-code
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The Exchange caught up with Appian CEO Matt Calkins after his enterprise app software company reported its first-quarter performance to discuss the low-code market and what he’s hearing in customer meetings. To round out our general thesis — and shore up our somewhat bratty headline — we’ve compiled a list of recent low-code and no-code venture capital rounds, of which there are many.
As we’ll show, the pace at which venture capitalists are putting funds into companies that fall into our two categories is pretty damn rapid, which implies that they are doing well as a cohort. We can infer as much because it has become clear in recent quarters that while today’s private capital market is stupendous for some startups, it’s harder than you’d think for others.
Bird’s SPAC filing shows scooter-nomics just don’t fly
A pair of Bird e-scooters parked in Barcelona. Image Credits: Natasha Lomas/TechCrunch
Historically — and based on what we’re seeing in this fantastical filing — Bird proved to be a simply awful business. Its results from 2019 and 2020 describe a company with a huge cost structure and unprofitable revenue, per filings. After posting negative gross profit in both of the most recent full-year periods, Bird’s initial model appears to have been defeated by the market.
What drove the company’s hugely unprofitable revenues and resulting net losses? Unit economics that were nearly comically destructive.
Dear Sophie: Does it make sense to sponsor immigrant talent to work remotely?
Image Credits: Bryce Durbin/TechCrunch
Dear Sophie,
My startup is in big-time hiring mode. All of our employees are currently working remotely and will likely continue to do so for the foreseeable future — even after the pandemic ends. We are considering individuals who are living outside of the U.S. for a few of the positions we are looking to fill.
Does it make sense to sponsor them for a visa to work remotely from somewhere in the United States?
— Selective in Silicon Valley
The hamburger model is a winning go-to-market strategy
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“Today, we live in a world of product-led growth, where engineers (and the software they have built) are the biggest differentiator,” says Coatue Management general partner Caryn Marooney and investor David Cahn. “If your customers love what you’re building, you’re headed in the right direction. If they don’t, you’re not.
“However, even the most successful product-led growth companies will reach a tipping point, because no matter how good their product is, they’ll need to figure out how to expand their customer base and grow from a startup into a $1 billion+ revenue enterprise.
“The answer is the hamburger model. Why call it that? Because the best go-to-market (GTM) strategies for startups are like hamburgers:
- The bottom bun: Bottom-up GTM.
- The burger: Your product.
- The top bun: Enterprise sales.”
Software subscriptions are eating the world: Solving billing and cash flow woes simultaneously
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Krish Subramanian, the co-founder and CEO of Chargebee, writes that while subscription business models are attractive, there are two major pitfalls: First, payment.
“Regardless of company size, there’s an ongoing need to convince customers to sign up long term,” Subramanian writes. “The second issue: How do businesses cover the funding gap between when customers sign up and when they pay?”
Is there a creed in venture capital?
Image Credits: Aimee Blasee (opens in a new window)
Scott Lenet, the president of Touchdown Ventures, asks how deal-makers should think about how to handle themselves when counter-parties attempt to change an agreement. “When is it OK to modify terms, and when should deal-makers stand firm?” he asks.
“Entrepreneurs and investors should recognize that contracts are worth very little without the ongoing relationship management that keeps all parties aligned. Enforcement is so unusual in the world of startups that I consider it a mostly dead-end path. In my experience, good communication is the only reliable remedy. This is the way.”
Even startups on tight budgets can maximize their marketing impact
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“Search engine optimization, PR, paid marketing, emails, social — marketing and communications is crowded with techniques, channels, solutions and acronyms,” writes Dominik Angerer, CEO and co-founder of Storyblok, which provides best practice guidance for startups on how to build a sustainable approach to marketing their content. “It’s little wonder that many startups strapped for time and money find defining and executing a sustainable marketing campaign a daunting prospect.
“The sheer number of options makes it difficult to determine an effective approach, and my view is that this complexity often obscures the obvious answer: A startup’s best marketing asset is its story.”
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The Expensify EC-1
Let’s make it clear from the outset that this story is about an expense management SaaS business called Expensify. As you’d expect, yes, this is about the expense management market and how Expensify has grown, its technology and all of that. Normally, that would make us change the channel. But this is also a story about pirates; peer-to-peer hackers who asked, “Why not work from Thailand and dozens of countries across the globe?” and actually did it using P2P hacker culture as a model for consensus-driven decision-making — all with pre-Uber Travis Kalanick in a guest-starring role.
Most interestingly, this is a story about just not giving a damn about what anyone goddamn thinks, an approach to life and business that led to more than $100 million in annual revenue, and an IPO incoming on what looks to be a very quick timetable. Prodigious revenues, 10 million users and only 130 employees running the whole shebang — that’s a hell of an achievement in only 13 years.
If you’re going a bit “WTF,” well, we’d concur. Expensify is as contradictory as they come in the enterprise world. It’s managed to take what might well be the most boring part of the corporate business stack and turn it into something special. It doesn’t borrow its culture from other startups, it built its own tech stack from the ground up, and even hires in a completely radical way. Oh, and no one really has job titles either, because why the hell bother with hierarchy anyway? They’re pirates after all.
If expense management is about avoiding corporate plunder, then letting the pirates and hackers run the ship is probably the best approach. And now, Expensify is plundering the corporate spend world one travel ticket and business meal at a time just as the world is rebuilding in the wake of COVID-19.
TechCrunch’s writer and analyst for this EC-1 is Anna Heim. Heim is a tech journalist and former startup founder who has written for different tech publications since 2011. She recently joined Extra Crunch as a daily reporter, where she will be sharing insights on startups, particularly in SaaS. The lead editor of this package was Ram Iyer, the series editor was Danny Crichton, the copy editor was Richard Dal Porto, and original illustrations were created by Nigel Sussman with art direction from Bryce Durbin.
Expensify had no say in the content of this analysis and did not get advance access to it. Heim has no financial ties to Expensify or other conflicts of interest to disclose.
The Expensify EC-1 will be a serialized sequence of five articles published over the course of the coming weeks. We interviewed the company in February and March, well before the company announced a confidential filing of its S-1 to the SEC. Let’s take a look:
- Part 1: Origin story “How a band of P2P hackers planted the seeds of a unique expense management giant” (2,400 words/10 minutes) — Explores the colorful history of the Expensify founders’ days with Travis Kalanick’s venture before Uber, a P2P content distribution startup called Red Swoosh, and how that experience would eventually influence what would one day become an expense management giant.
- Parts 2-5: Upcoming shortly.
We’re always iterating on the EC-1 format. If you have questions, comments or ideas, please send an email to TechCrunch Managing Editor Danny Crichton at danny@techcrunch.com.
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How a band of P2P hackers planted the seeds of a unique expense management giant
Individuality often has no place in the enterprise software space. In a market where a single contract can easily run into the millions, homogeneity is the herald of reliability and serves to reassure buyers of the worth of their potential purchase.
So it’s natural to think a company in the expense report management business would keep it simple and play it by the book. But one look at Expensify is enough to tell you that this is a company that never even looked for the book.
Expensify’s origin story is one of a scrappy group of developers who turned travel into a catalyst for ideas and stuck together through highs and lows, ending up building one of the most unexpectedly original companies in enterprise software today.
Right from its famous “workcations,” to its management structure and its decision-making policies, Expensify has it in its DNA to eschew so-called best practices for its own ideas — a philosophy rooted in its founder and early team’s P2P hacker background and do-it-yourself attitude. As a result, Expensify is atypical of startups in many ways, inside and out.
Founder and CEO David Barrett made it clear his company was different in our first call itself: “We hire in a super different way. We have a very unusual internal management structure. Our business model itself is very unusual. We don’t have any salespeople, for example. We’re an incredibly small company. We focus on the employees over the bosses. Our technology stack is completely different. Our approach toward product design is very different.”
That description would make some people call Expensify weird even by startup standards, but this essential difference has set it apart in a space dominated by giants such as SAP Concur and Coupa. And that’s ultimately been to its benefit: Expensify reached $100 million in annual recurring revenue in 2020, with hefty 25% EBITDA margins to boot. There were also rumors of the company planning to go public during our interviews for this EC-1, but they stopped speaking to us in March, and now we know why: Expensify confidentially filed to go public on May 3.
Expensify’s origin story is one of a scrappy group of developers who turned travel into a catalyst for ideas and stuck together through highs and lows, ending up building one of the most unexpectedly original companies in enterprise software today.
When David met Travis …
To truly understand Expensify, you first need to take a close look at a unique, short-lived, P2P file-sharing company called Red Swoosh, which was Travis Kalanick’s startup before he founded Uber. Framed by Kalanick as his “revenge business” after his previous P2P startup Scour was sued into oblivion for copyright infringement, Red Swoosh would be the precursor for Expensify’s future culture and ethos. In fact, many of Expensify’s initial team actually met at Red Swoosh, which was eventually acquired by Akamai Technologies in 2007 for $18.7 million.
Barrett, a self-proclaimed alpha geek and lifelong software engineer, was actually Red Swoosh’s last engineering manager, hired after the failure of his first project, iGlance.com, a P2P push-to-talk program that couldn’t compete against Skype. “While I was licking my wounds from that experience, I was approached by Travis Kalanick who was running a startup called Red Swoosh,” he recalled in an interview.
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Brex, Ramp tout their view of the future as Divvy is said to consider a sale to Bill.com
Earlier today recent dog-parent Alex Konrad and fellow Forbes staffer Eliza Haverstock broke the news that Divvy, a Utah-based corporate spend unicorn, is considering selling itself to Bill.com for a price that could top $2 billion. For the fintech sector, it’s big news.
Corporate spend startups including Ramp and Brex are raising rapid-fired rounds at ever-higher valuations and growing at venture-ready cadences. Their growth and its resulting private investment were earned by a popular approach to offering corporate cards, and, increasingly, the group’s ability to build software around those cards that took into account a greater portion of the functionality that companies needed to track expenses, manage spend access, and, perhaps, save money.
The latter category was what Ramp focused on when it launched. It worked. More recently Ramp added expense tracking efforts to its own software suite. And Brex, an early leader in its efforts to get corporate cards into the hands of smaller, and more nascent businesses, has also built out its software efforts. So much so that the company, in conjunction with its huge recent fundraise, announced that it will begin offering a software package for a monthly fee.
Competitors like Airbase charge for their code, while some, like Divvy, traditionally have not.
Enter Bill.com. As the software work from the corporate spend startups has improved, it may have begun cutting into the corporate payments and expense software categories. For Bill.com in the payments world, and Expensify in the expense universe, that possible incursion could prove to be a growth-retarding concern. Thus, it makes sense to see Bill.com decide to take on the yet-private corporate spend startups that are playing the field; why not absorb a growing customer base and fend off competition in a single move?
To get a better handle on how the startups that compete with Divvy feel about the deal, TechCrunch reached out to both Ramp CEO Eric Glyman, and Brex CEO Henrique Dubugras. We’ll start with Glyman, who broadly agrees with our read of the situation:
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