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OMERS Ventures announces a new $750M fund for investing in North America, Europe

Published April 27, 2020

OMERS Ventures, the venture capital arm of the Ontario Municipal Employees Retirement System (OMERS), has put together a new, $750 million fund to invest in both Europe and North America.

The capital vehicle is larger than the group’s preceding European and North American funds combined. In 2019 OMERS Ventures announced a €300 million fund Europe-focused fund (TechCrunch covered its launch here), and the venture group’s last North American fund was worth $300 million back in 2017. The new $750 million is a hybrid, acting as both the firm’s Europe-focused capital pool and the source of funds from which it can invest in North American startups.

According to Damien Steel, a managing partner at OMERS Ventures, the firm invested about CAD$100 million from the original Europe fund, with the rest now reserved for follow-on investments; Steel told TechCrunch that he doesn’t anticipate that the full amount will be used for that purpose.

But the remaining differential is somewhat immaterial as the venture collective has a new, three-quarters-of-a-billion-dollars capital pool to put to work. According to Steel, OMERS Ventures has “consolidated [its] efforts and made a new transatlantic fund.” The firm’s hope is that the shared capital will lead to a more cohesive investing group than having two funds for different teams engendered.

OMERS Ventures expects to deploy around $200 million a year across Europe and North America, a pace that Steel says will be similar to preceding efforts.

The COVID era

I wanted to chase down what Steel and company are doing that’s different in the new era. Something new is a slightly different mindset concerning runway. Instead of the usual 18-month expectation between rounds, Steel told TechCrunch that expectations and planning are lengthening to 24 months or longer between capital events — enough cash to get through whatever the current downturn winds up becoming.

Happily for Steel and his firm, some OMERS portfolio companies are well capitalized, with the venture capitalist telling TechCrunch during a call that “that the companies [his firm has] invested in a have really benefited from the exceptional amount of liquidity that’s been available in the market over the last two years,” with some of their startups winding up “sitting on quite a lot of cash because arguably they raised too much in 2019 and 2018.”

The capital was cheap, Steel notes, so lots of companies took what was on offer. The result? Many startups heading into 2020’s recession have well-stocked bank accounts. Not all, of course, raised right before things got worse. The firms that didn’t may struggle.

Given that the new OMERS Ventures fund intends to invest both in North America and Europe, I wanted to know what’s different between the two regions today as the COVID-19 pandemic continues to drive economic havoc. Notable to me was the fact that Europe is doing as well as it is, with Steel noting that “the funding environment has remained more active in Europe than it has in the US.”

He’s seeing “healthy” activity in Europe around the Series A and B stages. It’s perhaps unsurprising, then, that Steel told TechCrunch that the startup valuation pressure it’s easy to find in the North America venture scene isn’t quite as tough in Europe. Steel noted that 20% and 30% drops in valuation multiples in American and Canada from prior levels are common, while in Europe “it’s definitely less than that.”

For founders that there’s new funds of scale coming together at all is likely welcome. OMERS Ventures expects to have closed eight deals from its new fund “within a month,” a quick pace given its age.

Disclosure: OMERS Ventures invested in Crunchbase, my former employer.

Indie.vc founder Bryce Roberts: Profitability is ‘more achievable than a Series A round’

Published April 27, 2020

Despite all evidence to the contrary, there’s more to building a startup than raising venture capital.

Founders are finding success without overly relying on VC dollars; some are even sharing profits with their respective employees and customers without the help of traditional funding and Silicon Valley power dynamics.

As some investors slow down their funding pace, it has become clear that profitability trumps funding and venture capital can only take a startup so far when the economy tanks and outside cash streams dry up.

In the Indie.vc portfolio, profitability is its driving force. In fact, its main criterion for funding is that a startup must be on a clear path to profitability with durable fundamentals like high gross margins or the ability to start charging for a product right away, as opposed to companies that need a significant amount of upfront investment for research and development.

Profitability, Indie.vc founder Bryce Roberts tells TechCrunch, needs to be a habit, and founders need to recognize that it’s not a switch they can just turn on. Startups looking to prioritize profitability need to start out as revenue-driven businesses that replace funding milestones with profitability goals.

“Genuinely, it’s not rocket science,” he says. “Profitability isn’t this crazy, elusive thing. It’s literally more achievable than a Series A round. It’s way more achievable than a Series B round. If you look at the kind of fall-off between those rounds, most entrepreneurs would be better off finding their path to profitability and scale.”

Indie.vc, which recently announced its latest batch of investments, advises founders to make sure they have what they need to be stable and then to create and measure value, Roberts says. That value, which differs depending on the company, must be quantifiable as some metric or revenue.

To do that, Roberts says founders should adopt a mindset where they’re focused on creating revenue opportunities, rather than cost savings. Indie.vc’s model also does not prioritize hiring ahead of growth, a strategy that seems to be working for its portfolio during the pandemic.

Understanding Duolingo’s quiet $10M raise

Published April 27, 2020

Earlier this month, edtech unicorn Duolingo raised $10 million in new venture capital from General Atlantic, per an SEC filing. With the raise, the online language learning platform accepted its first outside investor in almost three years. General Atlantic will take a board observer seat at the company, per Duolingo.

The company, which was last valued at $1.5 billion, says the round has increased its valuation, but it declined to share by how much.

General Atlantic has invested in a number of edtech companies around the world, like OpenClassrooms, Ruangguru and Unacademy. Duolingo said that General Atlantic’s global platform and experience with online education in Asia would help guide its own growth, specifically pointing to its plans to scale up the Duolingo English test.

The e-learning company last raised $30 million in December at that $1.5 billion valuation. To raise a smaller sum a few months later is uncommon. Historically, that type of raise could happen for a number of reasons: a company is accepting a later investment as part of the same funding round, it needs more cash and this is an easy way to raise it or the company tried to raise a new large round and failed to secure past $10 million.

So where does the language learning unicorn fit?

In Duolingo’s case, it said the $10 million was raised because it wanted to bring a new investor on, but didn’t need a massive amount of primary capital. Duolingo says it is cash-flow positive.

In the past few weeks, Duolingo launched a new app to help children read and write, passed one million paying subscribers for Duolingo Plus and disclosed that its annual bookings run rate is $140 million. The company also recently hired its first CFO and general counsel.

“Because our business has been growing very fast and we have more than enough capital, there was limited need for us to raise more primary capital. However, over the last year, we developed a relationship with General Atlantic,” the company said in a statement to TechCrunch.

Tanzeen Syed, a managing director for General Atlantic, said that Duolingo is a “market leader in the language learning space. Syed also said Duolingo has a “profitable, efficient business model while maintaining hyper-growth characteristics.”

Another key factoid here is that along with the $10 million, there was a larger secondary transaction, which occurs when an existing stockholder sells their stock for cash or to a third party, or to the company itself while the company is still private.

In this case, an existing investor in Duolingo sold a small portion of their existing stake to allow General Atlantic to have a bigger stake in the company.

The company declined to share the size of the secondary market transaction.

In light of this new information, Duolingo’s expansion to Asia, which has a robust market of English learners, welcomed one investor and lessened the stake of another.

Based on what we know, the transaction signals that a preexisting investor in Duolingo was looking for liquidity at a time where the public markets are tightening and private markets are pausing. And at a time when companies are staying private longer than ever before, secondary transactions are hardly rare.

Sometimes, however, secondary transactions signal a lack of faith from a preexisting investor in the company’s current trajectory.

Duolingo is full steam ahead on its goal to expand across the world — and now has new cash in the bank, and a new observer seat on the board, to prove it.

Smart ring maker Motiv acquired by ‘digital identity’ company

Published April 27, 2020

We weren’t alone in being impressed by Motiv. The startup helped flip the script on wearables by essentially cramming a fitness tracker’s worth of technology into a ring. This week, San Francisco “digital identity” startup Proxy announced that it’s acquiring the company.

The company’s site is littered in buzzwords, but Proxy specializes in digital key cards — essentially providing a way to use digital devices like smartphones to access businesses and homes. An odd fit for a company that makes exercise rings, until you look at what Motiv’s been up to in recent years.

Among the additions to the tiny hardware platform are NFC payments, lost phone tracking and two-factor device authentication through gait monitoring. Whether or not Proxy ultimately has interest in manufacturing and selling a fitness ring, there’s plenty of underlying technology here that would be of interest to a digital identity company.

Motiv crams a fitness band’s worth of functionality into a ring

“The demand for our technology is only going to increase and we saw a clear path forward in the importance of validating one’s identity in both the physical and digital worlds,” Motiv said in a blog post. “Keys, access cards and passwords are rapidly being replaced with a biometric identity which provides greatly improved security and convenience.”

While the app will continue to be available for download (no word on how long it will continue to offer support), the deal marks the end of Motiv’s online sales, while partner retailers will burn through the rest of their stock.

Proxy, on the other hand, says it’s committed to the ring as the future of the wearables category. “With this acquisition, Proxy plans to bring digital identity signals to smart rings for the first time and revolutionize the way people use technology to interact with the world around them,” the company writes. “We believe it’s possible to ignite a paradigm shift in how people use wearables to interface with the physical world, so they can do and experience things they never have before.”

While compelling, the fitness ring hasn’t exactly taken the wearable category by storm in the past three years, as the space continues to be almost exclusively dominated by smartwatches and headphones. For those who still believe in the form factor, Motiv has had some competition recently from companies like Oura, a ring largely built around sleep tracking.

$4 million richer, Walrus.ai has a pitch for companies looking for QA-testing tools

Published April 27, 2020

The co-founders of Walrus.ai, a new software company that raised $4 million in a new round of financing from Homebrew, Felicis Ventures and Leadout Capital, started their business with one problem.

Jake Marsh, Ogden Nathan and Scott White had a problem. They left Wealthfront to launch a new service that would solve what they saw as a key problem with new business workflows. Their idea was to integrate the disparate software silos that different parts of their former business used to complete assignments.

The company was going to be called Monolist and it was going to aggregate tasks across every tool into a single actionable list. Unfortunately it wasn’t working.

They had founded the business back in 2018 and had gone on to raise seed capital from Homebrew and Leadout Capital, but they were hitting walls in their product development.

“Reliability was a huge problem for us,” said company co-founder, Scott White. “There were various frameworks that would let you test your automation so that before you launch your software, you catch bugs… There were some code languages that exist that can help you do this, but they didn’t work for us at all.”

The browser testing frameworks that White and his co-founders were using hadn’t kept up with the evolution of the software development industry and couldn’t adequately recreate the ways that actual users would interact with the software. “The stuff is super brittle,” said White.

Typically, according to White, these assurance tests break and then force engineers and developers to then investigate why the tests broke, to see if they can figure out what went wrong with the test even before they move on to any quality assurance of the actual changes made to a product.

“They weren’t designed to handle that much complexity,” White said of the existing testing tools.

So White and his co-founders thought about how they’d solve what they see as one of the critical problems that engineers face.

“The problem for engineers right now is that writing tests for your applications is hard because you have to write code and the frameworks are very inflexible and flaky,” White said. “Engineers spend tons of time running tests and if those tests fail then your code would not get shipped so you have to debut all those tests.”

Enter the new venture from White and his co-founders.

That would be Walrus.ai . “We’re outsourced engineering through an API,” said White. “We understand how to do testing and we can do it way better and more quickly.”

Using simple text descriptions of a planned user interface, Walrus.ai’s co-founder said his company can run diagnostics on just how effectively the code manages to execute its planned commands.

Given its status as a relatively new kind on the testing block, Walrus.ai only has tens of paying customers right now as it spins out from Monolist.

The company sees its competition coming primarily from outsourced quality assurance companies like Rainforest QA; test recorders like Mabel and Testim; and testing frameworks like Selenium and Cypress, but believes that its ability to take natural language prompts and run QA tests will be enough of a differentiator to capture a significant share of the market.

Factorial raises $16M to take on the HR world with a platform for SMBs

Published April 27, 2020

A startup that’s hoping to be a contender in the very large and fragmented market of human resources software has captured the eye of a big investor out of the US and become its first investment in Spain.

Barcelona-based Factorial, which is building an all-in-one HR automation platform aimed at small and medium businesses that manages payroll, employee onboarding, time off and other human resource functions, has raised €15 ($16 million) in a Series A round of funding led by CRV, with participation also from existing investors Creandum, Point Nine and K Fund.

The money comes on the heels of Factorial — which has customers in 40 countries — seeing eightfold growth in revenues in 2019, with more than 60,000 customers now using its tools.

Jordi Romero, the CEO who co-founded the company with Pau Ramon (CTO) and Bernat Farrero (head of corporate), said in an interview that the investment will be used both to expand to new markets and add more customers, as well as to double down on tech development to bring on more features. These will include RPA integrations to further automate services, and to move into more back-office product areas such as handling expenses,

Factorial has now raised $18 million and is not disclosing its valuation, he added.

The funding is notable on a couple of levels that speak not just to the wider investing climate but also to the specific area of human resources.

In addition to being CRV’s first deal in Spain, the investment is being made at a time when the whole VC model is under a lot of pressure because of the global coronavirus pandemic — not least in Spain, which has a decent, fledgling technology scene but has been one of the hardest-hit countries in the world when it comes to COVID-19.

“It made the closing of the funding very, very stressful,” Romero said from Barcelona last week (via video conference). “We had a gentleman’s agreement [so to speak] before the virus broke out, but the money was still to be wired. Seeing the world collapse around you, with some accounts closing, and with the bigger business world in a very fragile state, was very nerve wracking.”

Ironically, it’s that fragile state that proved to be a saviour of sorts for Factorial.

“We target HR leaders and they are currently very distracted with furloughs and layoffs right now, so we turned around and focused on how we could provide the best value to them,” Romero said.

The company made its product free to use until lockdowns are eased up, and Factorial has found a new interest from businesses that had never used cloud-based services before but needed to get something quickly up and running to use while working from home. He noted that among new companies signing up to Factorial, most either previously kept all their records in local files or at best a “Dropbox folder, but nothing else.”

The company also put in place more materials and other tools specifically to address the most pressing needs those HR people might have right now, such as guidance on how to implement furloughs and layoffs, best practices for communication policies and more. “We had to get creative,” Romero said.

At $16 million, this is at the larger end of Series A rounds as of January 2020, and while it’s definitely not as big as some of the outsized deals we’ve seen out of the US, it happens to be the biggest funding round so far this year in Spain.

Its rise feels unlikely for another reason, too: it comes at a time when we already have dozens (maybe even hundreds) of human resources software businesses, with many an established name — they include PeopleHR, Workday, Infor, ADP, Zenefits, Gusto, IBM, Oracle, SAP, Rippling, and many others — in a market that analysts project will be worth $38.17 billion by 2027 growing at a CAGR of over 11%.

But as is often the case in tech, status quo breeds disruption, and that’s the case here. Factorial’s approach has been to build HR tools specifically for people who are not HR professionals per se: companies that are small enough not to have specialists, or if they do, they share a lot of the tasks and work with other managers who are not in HR first and foremost.

It’s a formula that Romero said could potentially see the company taking on bigger customers, but for now, investors like it for having built a platform approach for the huge but often under-served SME market.

“Factorial was built for the users, designed for the modern web and workplace,” said Reid Christian, General Partner at CRV, in a statement. “Historically the HR software market has been one of the most lucrative categories for enterprise tech companies, and today, the HR stack looks much different. As we enter the third generation of cloud HR products, with countless point solutions, there’s a strong need for an underlying platform to integrate work across these.”

Seed investors take long view on promising enterprise startups

Published April 27, 2020

The job of an early-stage startup founder is challenging in good times, never mind a crash like the one we are experiencing today.

While most expect private investing to slow down, it’s clear that some investments are still happening in spite of the pandemic, if the stories we are writing on TechCrunch are any indication.

But the downturn is bound to have an impact on the types of deals that receive funding; any startup that offers a good or service requiring human interaction or installation will face an uphill battle, at least in the short term. That said, enterprise SaaS vendors, especially ones that solve hard problems, help with work-from-home or collaboration, or better yet, help increase efficiency and save money, are still very much in demand.

Nobody can do anything about the CIO who is hunkering down until things improve — but that’s not everyone. Companies might be thinking twice about where they spend money, but some are still helping drive the net-new, post-COVID-19 investments happening from seed to late stage across many sectors.

We looked at data and spoke to a couple of enterprise-focused, NYC-based seed investors to better understand their investing cadence. Nobody painted a rosy picture of today’s climate, but seed investors were never about immediate gratification, especially where enterprise startups are concerned. That means, if a seed-stage investor believes in the founders and their vision and the company can ride out today’s economic upset, there’s still money in the till — at least for now.

Seed investment generally in decline

Shine adds invoice insurance to its freelancer bank account

Published April 27, 2020

French startup Shine is adding a new option today. If you think there’s a chance that a client is not going to pay your next invoice, you can insure that invoice to avoid any bad surprise.

Shine is building a challenger bank for freelancers and small companies. It lets you send and receive money in a separate business account, pay with a MasterCard, create invoices and stay on top of administrative tasks.

It also helps you get started as the startup can fill out all administrative paperwork to register yourself as a freelancer. You also get notifications to remind you that you should pay your taxes and more. Starting accepting freelancing jobs can be confusing and Shine can help you with that.

Shine has a built-in invoicing tool. It lets you add a client and generate an invoice directly in the mobile app. After that, you can send a link to your client. You get a notification when your client opens the invoice. They can download a PDF and get your bank details to pay you.

And yet, many clients often wait until the last minute to pay an invoice. It can be a month or two after finishing a job, which means that they also forget about outstanding invoices.

In a few weeks, Shine users will be able to create an invoice and insure it before sending it. It costs you 2% of your total amount on your invoice. There’s no subscription fee, it’s a one-off process.

If your client hasn’t paid you after the due date, Shine will reach out to your client again to try to get the payment. If that doesn’t work, you can file a claim with the partner insurance company.

In that case, if the company is still operating, you get paid 100% of your invoice. If the company has collapsed, you get 90% back. (Of course, that’s without taking into account the 2% fees you already paid.)

How freight master Flexport’s Ryan Petersen learned to CEO

Published April 26, 2020

“I didn’t know what the term ‘freight forwarder’ meant until a year into starting the business.” Considering his shipping logistics startup Flexport was last valued at $3.2 billion, that quote from my first interview with CEO and founder Ryan Petersen back in 2016 seems even more surprising now.

But it also hints at why he’s one of the most talented and exciting executives in tech: He learns. Humbly. Relentlessly. About whatever the role requires as it evolves.

Right now, it means learning that 1.15 million medical masks can fit in a pasenger plane if you strap boxes to the seats like they’re people. Flexport has delivered around 62 million pieces of personal protective equipment, with delivery of over 10 million of those funded by the company’s impact arm Flexport.org. Petersen and Flexport meanwhile helped create the Frontline Responders Fund that’s raised over $7 million for COVID relief.

Flexport.org packed 3 million pieces of PPE into a repurposed passenger plane to get them to frontline responders

“He’s one of the most impressive founders I’ve known” said fellow FRF leader and Science co-founder Peter Pham . “Ryan just wants to solve problems without ego.”

In this profile, TechCrunch charts Petersen’s growth across our six interviews with him over the past four years as he raised $1.3 billion and reached hundreds of millions in revenue.

Overcoming Shlep Blindness

Petersen soon found out that ‘freight forwarding’ means coordinating all the shipping and hand-offs to get pallets and containers of goods on one side of the world, through trucks and boats and planes, to a retailer on the other. By then Flexport was going through Y Combinator in 2014, preparing to take on the trillion-dollar freight industry.

Ryan Petersen

“I thought the problem was too big, and that I wouldn’t be able to solve it” he recalls. “How am I going to fix global trade? Only much later did I realize that, well, let’s try it! It can’t just sit there broken forever.” Somehow, freight forwarding was still being organized with faxed logs and paper manifests, or Excel files and email if a client was lucky.

Freight forwarding had plagued plenty of founders but none had tackled it because it seemed so insurmountable that it engendered ‘schlep blindness’, as YC’s co-creator Paul Graham termed it.

“Schlep blindness is something so hard that your brain won’t think about it. I think it’s a necessary feature of our brains. Otherwise we’d sit here contemplating our mortality all day and never be able to do anything” Petersen explains. “Anyone who ever sold anything on the internet pre-Stripe went through this terrible process. 100% of internet entrepreneurs saw that problem and then went about their way.” With its 100 year-old shipping incumbents and endless regulatory acronyms, who’d want to wade in?

“Ryan is what I call an armor-piercing shell: a founder who keeps going through obstacles that would make other people give up” says Graham, who donated $1 million to Flexport.org’s COVID-19 relief efforts. “But he’s not just determined. He sees things other people don’t see. The freight business is both huge and very backward, and yet who of all the thousands of people starting startups noticed?” Petersen.

What really irked him was that the big freight forwarders didn’t want those clients to learn what influenced prices and timelines to keep them in the dark about how sub-optimal their routes were. “They just made money off the fact that I didn’t understand how it all works. And I assumed at the time that that was just something about entrepreneurs who are new to this space but it turns out even the biggest companies struggle with this stuff. They’re afraid forwarders are trying to take advantage of them.”

But Petersen wasn’t so naive. He’d actually been in the freight business his whole life.

From Slinging Soda To Founding Startups

“Maybe without her realizing it, she was training us to be entrepreneurs” Petersen reflects. He and his brother David grew up with a biochemist mom who ran her own food safety business while their dad did the company’s programming. “All of our childhood conversations were around using software to make government regulations more accessible.” When would Flexport would eventually be jumping through the hoops of the 43 different US trade regulators, it felt natural for its CEO.

Ryan Petersen back in 2015 before Flexport had its own planes

Petersen exudes a kinetic energy that subtly coveys that he’s always itching for the next knot to unwind. “At the time I was terribly bored by everything”. So his Mom put him to work. “She paid my allowance as a kid by having me deliver sodas to stock their office. My dad would drive me to Safeway to buy sodas for four bucks a case and sell them for nine.” With a laugh, he considers, “It was potentially a way for her to make my allowance tax-free.”

Soon Petersen was moving bigger items longer distances, buying scooters in China and selling them online in the States. By 2005, Petersen was living in China to get closer to the supply chains. The next year, he co-founded ImportGenius with his brother and Michael Klanko. They’d realized there was a ton of valuable information locked up in paper shipping manifests, so they began scanning and selling the data to importers and exporters so they could keep tabs on competitors.

Petersen’s first moment in the spotlight came in 2008 when he accidentally butted heads with Steve Jobs. ImportGenius had identified that Apple was shipping a large number of “electronic computers”, a new classification for the company. “We scooped the launch of the iPhone 3G with our public manifest data. Steve Jobs called US Customs, who called me” he told me back in 2016.

Though ImportGenius eventually plateaued, Petersen had accumulated the knowledge to lift the veil and pierce his schlep blindness. “I realized the largest problem was staring me in the face. Global trade is too hard, and there’s not software to manage it” he remembers. “I thought there was no software for SMBs. What I discovered was that there’s NO software.”

At first he wanted to build what would become Flexport inside of ImportGenius, but it was tough to get existing investors to stomach the risk. It’d be scary, but also exciting to start something separate. “My brother is my best friend and my best advisor” Petersen tells me. They’d always pushed each other with a jovial sense of competition — Ryan’s Twitter handle is @TypesFast. David’s is @TypesFaster.

So David made the first move, founding BuildZoom, which has gone on to raise $23 million to coordinate the logistics (are you sensing a pattern?) of hiring contruction contractors. In 2013, Ryan lept. “I think part of me wanted to go out on my own and prove myself . . . to prove that I was capable of running the show. It was a really, really challenging to do it. Then the day I did it, it was the most liberating, awesome feeling ever.”

They Laugh At You, Then You Raise $1 Billion

It took a few years to get all its regulatory approvals and develop the basis of the Flexport product. But with early capital from Founders Fund, Petersen built the freight software he’d spent so long pining for. Still, “Senior execs at big companies were making fun of us. One of them compared us to Doc Emett Brown [from Back To The Future] and his ‘flex capacitor’ but we he missed is that Doc invented a time machine and it worked.”

By 2016, Flexport was serving 700 clients across 64 countries. I described it as the unsexiest trillion-dollar startup, attacking an enormous industry that was so boring that it repelled earlier innovation. Oversaturation in consumer startup verticals was pushing investors to look to where tech was evolving previously untouched markets. Flexport raised a high-profile $110 million round led by DST at a $910 million post-money valuation in 2017, and Silicon Valley was starting to take notice.

The Flexboard Platform dashboard offers maps, notifications, task lists, and chat for Flexport clients and their factory suppliers.

Luckily, the freight big-wigs were still laughing despite Flexport moving 7000 shipping containers per month for 1800 customers. “I don’t worry about startup competitors. I worry the big guys will stop thinking of us as such a joke” Petersen said that year. Soon incumbents like 25-year-old Chinese private delivery giant S.F. Express were allying with Flexport, leading another $100 million round in 2018. Meanwhile, Flexport was trying to sound more like its older competition. Petersen told me “We’re trying to retire the word ‘startup’. [Our clients] want a company that will help them grow, not the fly-by-night startup.”

At that point, Petersen didn’t care if freight was appealing or not. “I never thought it was sexy or unsexy. I just thought it was a backstage pass to the world economy” he’d later say. Yet SoftBank’s Saudi-backed Vision Fund felt the attraction. Flexport was vertically integrating, adding freight financing so retailers could pay factories for good they’d sell months later. It was also chartering its own plane and operating its own warehouses where it could experiment with next-generation logistics, scanning the physical dimensions of everything that came through its doors to optimize future shipments.

By then, Flexport had plenty of exit options. But Petersen was enjoying the ride. “I’m just having fun. You have a purpose. You get invited to interesting things. Once you sell your business, you’re just another rich guy. I never want to sell the business.” Luckily, the potential to grab more of the freight forwarding profits convinced SoftBank to invest a jaw-dropping $1 billion into Flexport in early 2019 at a $3.2 billion post-money valuation.

“It was controversial with our board. They thought it was a lot of dilution to take on but I convinced them that, this was going to go up and down and we wanted we to have cash to ride out the cycles. My view is that the world’s uncertain. You should be prepared for all outcomes” Ryan explains. As long as it could weather the storm, “we’re going to win on some time horizon.”

That strategy soon paid off. When trade with China effectively halted as COVID-19 exploded in the country and Flexport had far fewer containers to coordinate, it didn’t have to execute mass layoffs like fellow late-stage startups. It proactively cut 3% of its staff or around 50 people on February 4th, centered in recruiting that it plans to slow. “It’s painful to disappoint people” Petersen reveals.

Flexport chartered its own plane for several years to ship freight

Transitioning to a recession-era CEO and learning to reduce headcount with empathy became Petersen’s new objective. “I wanted people to know that I take personal responsibility for it. I wanted people to know that there’s transparency here” he tells me, his voice straining under the gravity of the situation. “If people feel fear and then they look at the leadership and they think the leadership is not feeling fear, then the fear amplifies. Whereas if people feel fear and they see, ‘oh the leaders are feeling fear also? Then okay, they’re going to behave appropriately.’”

Taking decisive action before COVID-19 spread widely stateside kept Flexport’s momentum strong and its runway long. Petersen is proving he can guide the company through bust as well as boom.

Flexport’s Tricks To Management

“My big learning in the last 18 months or so is that you can’t do everything. You can do anything you want, but you can’t do everything” Petersen outlines. “I see good ideas and I say ‘DO THAT!’” he tells me with a wry smile. “Soon, you’re spread pretty thin. You need some top down discipline to say ‘no’ to things. We really lacked that in the early years.”

The quest for discipline led him to develop and lean on two major frameworks for prioritizing customer needs and preserving company culture. They’re crucial now that Flexport has grown to 1800 employees across 14 offices and 6 warehouses, and 10,000 clients including Sonos, Kleen Kanteen, and Timbuk2.

Ryan Petersen whiteboards his management frameworks

The first framework is from Petersen’s mentor and American business mogul Charlie Munger. It lays out the six stake-holders or ‘customers’ a business must satisfy to succeed. Here’s how Petersen describes them:

Clients: The people who pay you money. For Flexport, we have both importers and exporters
Vendors: The people you pay. For Flexport, who own the planes, ships, and trucks
Employees: Make sure they’re treated well. It has to be a win-win trade.
Investors: They deserve a return on their money. They took a risk
Regulators: They decide who to give licenses to. For Flexport, there are 43 regulators in just the US who take an interest in imported products.
Communities: Where you operate. Maybe one day that’s global society

“If you don’t have at least a B grade in everything and ideally an A, you’re probably not long-term sustainable” Petersen explains. It’s a smart lens for anyone assessing companies, whether that’s ones to work at, invest in, work with, or one you’re leading and trying to improve.

Take Airbnb for example. Clients generally love its alternative to hotels, they’ve been able to continuously recruit employees effectively, and investors have offered it billions and kicked in to help it survive COVID-19. But its vendor hosts and their neighbors have struggled with disruptive guests, and communities and their local regulators have clashed with the startup over its impact on housing supply. The six customers concept identifies where Airbnb needs to work harder.

The second framework Petersen developed himself for how to ensure a company’s core values persist as it scales. It lays out the six culture questions:

Why?: Why do you exist? What’s your purpose, mission, vision, and impact?
Who?: Who do you hire and what values and behaviors do you look for?
What?: What are you focused on and what metrics do you use to measure success?
How?: How do decisions get made and how do you shorten the feedback loop for improvement?
When?: When should things get done and when should you ship your product?
Where?: Where does your team feel like it belongs and how do you become more inclusive?

Petersen likens these tenets to addressing a medical condition. It’s easier if leaders build them into their culture early than trying to fix them later. “If you were to get these things right in any company, you’ll outperform” he believes.

To execute on these, Petersen built a team close to him that just “makes sure our OKRs (objectives and key results) are clear, that we’re running inclusive meetings with good documentation, that we’re holding people accountable.” The method is heavily influenced by Amazon’s corporate style. As Petersen told me last year, “The English language lacks a positive word for bureaucracy.”

Ryan Petersen

Taking process seriously has made the CEO a hit with his employees. “Working for Ryan accelerated my career at least a decade. He has the uncanny ability to push people to their peak performance” said Flexport’s long-time former VP of product Sean Linehan, who went on to found Placement. “Ryan is building the playbook for operationally-intense tech businesses. Building a global logistics behemoth from scratch is an insanely complex job. But Ryan thrives in complexity. Where most entrepreneurs fall apart, he hits his stride.”

With the economics headwinds we’re facing, Petersen will need that drive if he wants to bring Flexport public. As you might expect, he’s learning about it. “I like reading annual reports. It’s like a hobby of mine, particularly with my competitors” Petersen says. “I want to go public. But I don’t want to go public until we’re profitable because I don’t want to be at Wall Street’s whims. If you’re losing money and you’re public and Wall Street doesn’t like your stock, you can get into this death cycle.”

Being the CEO of a company that outperforms has opened doors to new mentors too, like executive coach Matt Messari, and Microsoft’s Satya Nadella. Petersen asked Nadella “How can you make learning and development measurable?”. Redmond’s head honcho answered “You don’t have to measure everything.” Petersen took the note. Sometimes, you just do what you think is right.

The Wartime CEO

Leading with his heart has steered Flexport to join the coronavirus relief effort in huge ways. “We were not put on this earth to lay in bed staying warm under the blankets. It’s time to step up and do something for the world” Petersen tweeted.

Flexport’s response started in January with multiple blog posts per week laying out how COVID-19 was impacting global trade, how aid organizers could navigate supply chain issues, and how governments and private companies could help. Then it launched the Frontline Responders Fund and began routing all Flexport.org contributions to the cause, massively discounting freight forwarding costs to help get PPE wherever it’s needed.

Flexport.org launched the Frontline Responders Fund

“100% of your donation to this cause will go directly toward shipping masks to people on the front lines as fast as possible. I give you my word that we won’t waste a penny of your money” Petersen tweeted. Despite his business encountering its own troubles with global trade and demand disrupted, he shifted to spending his full time running Flexport.org and promoting the FRF. With the help of celebs like Arnold Schwarzenegger and Edward Norton, it’s raised over $7 million. The FRF has delivered over 6.9 million masks, 240,000 gowns, 1,000 ventilators, 155,000 gloves, and 250,000 meals for vulnerable populations.

Petersen hasn’t been shy about rallying more leaders to the cause, writing this expansive guide to the major bottlenecks blocking relief. “Philanthropists should also step up, lending money to organizations that have received purchase orders for PPE, but that can’t afford to buy the equipment unless they are paid upfront. Because they’ll get their money back when the pandemic subsides, this is one of the highest impact forms of philanthropy out there right now.”

That willingness to get involved has inspired his employees to roll up their sleeves too. “During a crisis, leaders really show the values they embody” says Susy Schöneberg, head of Flexport.org. “After the COVID-19 outbreak, Ryan immediately offered us more resources to support our commercial and nonprofit clients. Over the last weeks, my days started and ended by talking to him – no matter what time is was.”

Ryan Petersen

From his vantage point, Petersen also has special visibility into who is trying to exploit the crisis. “Effective immediately Flexport will not ship personal protective equipment unless the customer can demonstrate which hospital system or other frontline emergency responder they are being provided to” Petersen wrote. “There are global shortages of these products, and it is immoral to allow war-profiteering from entrepreneurs looking to make an easy dollar.”

In the absence of proper federal crisis management, Petersen has become a defacto general in the war against coronavirus. “Given the scale of the problem and the complexity of the market failures outlined above, there’s no way for the US government to solve this on its own. But it can and must provide leadership, breaking down obstacles and coordinating the response of the private sector.” Until then, Petersen’s learning as fast as he can to become the wartime CEO needed right now.

Paraphrasing Kobe Bryant, Petersen concludes, “When you know what your goal is, the entire world is your library.”

For more of this author Josh Constine’s thoughts on tech, subscribe to his newsletter Moving Product

Decrypted: Space hacking, iPhone vulnerability, Zoom’s security boom

Published April 26, 2020

Security startups to the rescue.

As we continue to ride out the pandemic, security experts are closely monitoring the surge of coronavirus-related cyber threats. Just this week, Google’s Threat Analysis Group, its elite threat hunting unit, says that while the overall number of threats remains largely the same, opportunistic hackers are retooling their efforts to piggyback on coronavirus.

Some startups are downsizing and laying off staff, but several cybersecurity startups are faring better, thanks to an uptick in demand for security protections. As the world continues to pivot toward working from home, it has blown up key cybersecurity verticals in ways we never expected. To wit, identity startups are needed more than ever to make sure only remote employees are getting access to corporate systems.

Can the startups take on the giants at their own game?

THE BIG PICTURE

Another payments processor drops the security ball

For the third time this year, a payments processor has admitted to a security lapse. First it was Cornerstone, then it was nCourt. This time it’s Paay, a New York-based card payment processor startup that left a database on the internet unprotected and without a password. Worse, the data was storing full, plaintext credit card numbers.

Anyone who knew where to look could have accessed the data. Luckily, a security researcher found it and reported it to TechCrunch. We alerted the company; it quickly took the data offline, but Paay denied that the data stored full credit card numbers. We even sent the co-founder a portion of the data showing card numbers stored in plaintext, but he did not respond to our follow-up.