VC’s largest funds make big bets on vertical B2B marketplaces

During the waning days of the first dot-com boom, some of the biggest names in venture capital invested in marketplaces and directories whose sole function was to consolidate information and foster transparency in industries that had remained opaque for decades.

The thesis was that thousands of small businesses were making specialized products consumed by larger businesses in huge industries, but the reach of smaller players was limited by their dependence on a sales structure built on conferences and personal interactions.

Companies making pharmaceuticals, chemicals, construction materials and medical supplies represented trillions in sales, but those huge aggregate numbers hide how fragmented these supply chains are — and how difficult it is for buyers to see the breadth of sellers available.

Now, similar to the way business models popularized by Kozmo.com and Webvan in decades past have since been reincarnated as Postmates and DoorDash, the B2B directory and marketplace rises from the investment graveyard.

The first sign of life for the directory model came with the success of GoodRX back in 2011. The company proved that when information about pricing in a previously opaque industry becomes available, it can unleash a torrent of new demand.


By Jonathan Shieber

Sam Lessin and Andrew Kortina on their voice assistant’s workplace pivot

Sam Lessin, a former product management executive at Facebook and old friend to Mark Zuckerberg, incorporated his latest startup under the name “Fin Exploration Company.”

Why? Well, because he wanted to explore. The company — co-founded alongside Andrew Kortina, best known for launching the successful payments app Venmo — was conceived as a consumer voice assistant in 2015 after the two entrepreneurs realized the impact 24/7 access to a virtual assistant would have on their digital to-do lists.

The thing is, developing an AI assistant capable of booking flights, arranging trips, teaching users how to play poker, identifying places to purchase specific items for a birthday party and answering wide-ranging zany questions like “can you look up a place where I can milk a goat?” requires a whole lot more human power than one might think. Capital-intensive and hard-to-scale, an app for “instantly offloading” chores wasn’t the best business. Neither Lessin nor Kortina will admit to failure, but Fin‘s excursion into B2B enterprise software eight months ago suggests the assistant technology wasn’t a billion-dollar idea.

Staying true to its name, the Fin Exploration Company is exploring again.


By Kate Clark

On-demand shipping startup Shyp is shutting down

After rocketing to a $250 million valuation in 2015 amid a massive hype cycle for on-demand companies, on-demand startup Shyp is shutting down today.

CEO Kevin Gibbon announced that the company would be shutting down in a blog post this afternoon. The company is ending operations immediately after, like many on-demand companies, struggling to find a scalable model beyond its launching point in San Francisco. Shyp missed targets for expanding to cities beyond its core base as well as pulled back from Miami. In July, Shyp said it would be reducing its headcount and shutting down all operations beyond San Francisco.

The company raised $50 million in a deal led by John Doerr at Kleiner Perkins back in 2015, one of his last huge checks as a variety of firms jumped onto the on-demand space. The thesis at the time was pretty sound: look at a strip mall, and see which businesses can come to you first. Shipping was a natural one, but there was also food, and eventually groceries. Today, there are only a few left standing, with Postmates, Instacart and DoorDash among the most prominent ones. Even then, Instacart is now under threat from Amazon, which is ramping up its own two-hour delivery after buying Whole Foods.

“At the time, I approached everything I did as an engineer,” Gibbon wrote. “Rather than change direction, I tasked the team with expanding geographically and dreaming up innovative features and growth tactics to further penetrate the consumer market. To this day, I’m in awe of the vigor the team possessed in tackling a 200-year-old industry. But, growth at all costs is a dangerous trap that many startups fall into, mine included.”

Shyp is now a casualty of the delivery space. Where it originally sought to make up the cost of delivery in the form of cheaper bulk costs for those deliveries, Shyp’s one-size-fits-all delivery — where you could deliver a computer or a bike — eventually ended up being one of the most challenging and frustrating elements of its business. It began adding fees to its online returns business and changing prices for its bulk shipments. As it turns out, a $5 carte blanche for delivery was not a model that really made sense.

Indeed, that growth-at-all-costs directive has cost many startups, with companies like Sprig shutting down and many companies getting slapped on the wrist for aggressive growth tactics like text spamming. It also meant that startups had to very quickly develop an effective playbook that, in the end, might not actually translate to markets beyond their core competency. Shyp pivoted to focusing on businesses toward the tail end of its lifetime, including a big deal with eBay, which we had heard at the time was doing well.

“We decided to keep the popular-but-unprofitable parts of our business running, with small teams of their own behind them,” he wrote. “This was a mistake—my mistake. While large, established companies have the financial freedom to explore new product categories for the sake of exploring, for startups it can be irresponsible.”

But Gibbon said the company kept parts of its popular but challenged models online – which may have also contributed to its eventual shut-down. The company expected to be in cities like Boston, Seattle and Philadelphia in early 2016, but that didn’t end up panning out. And Shyp increasingly felt the challenges of an on-demand model, trying to push the cost to the consumer as low as possible while handling the overheads and logistical headaches of a delivery business.

“My early mistakes in Shyp’s business ended up being prohibitive to our survival,” Gibbon wrote. “For that, I am sorry.”