TrueNorth has raised $50 million from Sam Altman and others to empower independent truckers

Jin Stedge studied aerospace engineering at MIT, but after she found herself at Scotty Labs, an SRI International spin-out focused on autonomous driving, she says she came to appreciate how far away the tech is from large-scale adoption.

Indeed, when Scotty was acquired by DoorDash in the summer of 2019, she teamed up with Sanjaya Wijeratnebut, a colleague and senior software engineer at Scotty Labs, and they got to work on a more ruthlessly practical challenge: empowering truck drivers to run their current businesses more efficiently.

For Stedge, it was largely personal. Her  grandparents were owner operators who acquired up to six trucks in the 1980s; her uncles and cousins later entered the business, too, she says. Armed with their insights, she knew the daily difficulties that independent truckers endure.

She also knew that predictions by AI experts who said truck drivers would be out of work by 2027 were flat wrong. “If you think about what long-haul truckers do,” says Stedge, “they go over the Rockies, they have to tarp freight to the back of their trucks, they’re often without cell service for hours at a time — that kind of environment is just really hard to automate.”

It helped, of course, that the market they’d be chasing is enormous. It’s no coincidence that so many startups have flocked to address different aspects of the trucking industry, from brokers and load marketplaces to outfits that help with cash flow, make equipment, provide insurance or make compliance products.

In fact, the opportunity that Stedge and Wijeratnebut spied with their startup, TrueNorth, was to create a single, easy-to-use platform to help truckers manage their customers; find, book, and coordinate loads; optimize their routes; invoice their customers; and collect payment. It would also pay them upon the completion of a job, so drivers wouldn’t be forced to wait a month or more to be paid, as has long been customary.

The idea, broadly speaking, was for TrueNorth to give the independent truckers who make up somewhere between 10% and 20% of the industry the resources of a larger fleet — and better economics.

Y Combinator liked the pitch enough to welcome Stedge and Wijeratnebut into its winter 2020 batch. A seed check from Sam Altman quickly followed, then an $8.5 million Series A round led by former Stripe exec Lachy Groom.

Now, Stedge says, the company has just closed on $50 million in Series B funding co-led Groom and Altman (along with brothers Max and Jack). Many others have joined the ride, too, including  Flexport Fund, Tribe Capital, Original Capital, K5 Global, 137 Ventures, and Fifth Down Capital.

TrueNorth has so far raised $61.8 million altogether.

The question begged is whether TrueNorth, which already employs 50 people — half of them women, notably —  can deliver on its promises.

Certainly, the $50 million should help, along with $10 million in working capital that TrueNorth has separately secured from a debt provider. It’s already using that money to ensure its customers get paid promptly after each job.

The company is also already lowering costs for the roughly 200 truckers already using its software, insists Stedge. She says that just one way it’s doing this is pooling its customers together and securing lower-cost insurance for the group. (“An independent trucker who’s truly on their own will pay $20,000 to $30,000 a year in insurance, which is crazy,” says Stedge. “With us, they pay $10,000 a year.”)

TrueNorth says, too, that it increases drivers’ revenue by helping them find the highest-paying trucking jobs and making it simple to book them.

Still, one outstanding question is how effectively TrueNorth is able to reach its customers, given that it is targeting a very fragmented market. Stedge notes that the company has “never done outbound sales” because all of its customers have found the company on their own, and she says that 90% have additionally referred friends. With deeper pocketed rivals, it could need to spin up a more aggressive marketing strategy.

One rival in particular would seem to be a threat, and that’s CloudTrucks, which just two weeks ago closed on $115 million in Series B funding and whose founder, Tobenna Arodiogbu, previously cofounded Scotty Labs, where he was CEO.

Like TrueNorth, Arodiogbu’s vision is to help trucking entrepreneurs operate their businesses. As he told TechCrunch in late November, “Lots of tools are being built for brokers and shippers, but not nearly enough is being done for the truck driver who’s actually doing the really hard work.”

For her part, Stedge sees CloudTruck’s momentum as a strong signal to truckers and investors alike. “We serve the same customer, which is independent truckers, [but] I think it’s good, to be honest,” she says. “It’s a humongous market. It’s a $100 billion market, just in these independent truckers and small fleets. So the more people who are helping owner operations and who are doing that marketing and brand awareness, the better.”

In the meantime, Stedge is hiring fast, and revenue is starting to add up for the young company, which charges customers between 15% and 18% of all goods they move. (If that seems high, Stedge observes that big fleets often take closer to 40%.) Right now, those drivers are delivering between $30,000 and $50,000 per year per trucker, which puts TrueNorth’s gross revenue at between $6 million and $10 million. But that’s up 3.4 times over the last six months alone, and the company is still mostly operating in its first market Dallas, and more newly in Atlanta, says Stedge.

As important, she says: the company has been significantly improving its contribution margin, which is basically the portion of sales that helps to offset its fixed costs. “It doesn’t matter if you’re growing really fast if there’s a leaky bucket,” says Stedge, who could just as well be talking about one of her trucking customers.

“You want to know that you’re building a business that lasts, and we have been very efficient with our money.”

137 Ventures, which buys equity from private company shareholders, just raised a new fund

137 Ventures, a 10-year-old, San Francisco-based investment firm that mostly buys private company shares of founders, executives, early employees, and other large shareholders of private, high-growth tech companies, has closed its fifth fund with $350 million. It’s the largest fund the outfit has raised to date (its fourth fund initially closed with $210 million in 2019 and later ballooned to $250 million).

It’s certainly no surprise that 137 Ventures —  which also makes small investments in primary rounds on occasion — is chugging along. Of the roughly 75 companies it has acquired stakes in over the years, it says that 13 have gone public and that seven of the 13 have gone public over the last 14 months, including Airbnb, Wish, and Palantir.

It has some valuable equity in its portfolio, too, including SpaceX, Gusto, Flexport, Workrise, and Curology.

The five largest investments by dollars invested since the launch of the firm’s fourth fund in 2019 are Workrise, Wonolo, Thirty Madison, Anduril, and Lattice, it says.

We had a quick chat with firm cofounder Justin Fishner-Wolfson yesterday to talk about the go-go market and how it’s impacting his firm. Unsurprisingly, he said that “everything is shockingly faster,” which has accelerated 137 Ventures’s work, too. There are more companies to meet with than ever before, for example, which has meant that that the firm has had to beef up a bit and that it continues to hire.

“There are a lot of conversations to be had,” he said.

With private market valuations soaring so fast, his firm is also facing unprecedented competition, he conceded. He says it helps that 137 Ventures has managed to establish a brand already. There’s a benefit to having done this for a decade. Still, while one can “win deals if people think you’re helpful and smart and you’re going to be there when times are more challenging than they are today,” market participants “do have to pay market prices,” he said, and you have to “have more coverage and to make sure people know who you are. You have to work to stay in front of everybody.”

Asked if employees are more or less eager to sell their shares, given that so many startups are seeing their valuations triple and even quadruple so quickly right now, he suggested they haven’t changed all that much in this market. He says there are just more of them because there are more companies that are faring well, as well as continuing to wait on an “exit” event.

He also says that companies are, in some cases, allowing employees and other insiders to sell earlier in the startup’s life cycle.

Not last, and not surprisingly, 137 Ventures is seeing more startups put processes in place far earlier when it comes to letting insiders sell a portion of their shares. Likely they need to do this in order to retain talent but also, as Fishner-Wolfson, noted, they’ve probably learned from watching earlier companies. He pointed, for example, to Palantir, which had no real restrictions on trading. “That had some positive and some negatives,” he observed.

As for 137 Ventures, Fishner-Wolfson insisted it isn’t playing the market buy trading its shares as they rise — and sometimes fall — in value.

He estimated that its average holding period is “six or seven years” and said that the firm typically waits until a company has gone public to begin exiting 137 Ventures’s investment in it. Even then it might hold the shares a while, depending on the life cycle of the fund. Said Fishner-Wolfson: “We’re trying to invest in companies that are among the most successful in their categories, so we’re trying to invest in them for a really long time.”

Wish (and Airbnb, and Palantir) investor Justin Fishner-Wolfson doesn’t care about first-day pops

It’s probably no wonder that when Founders Fund was still a very young venture firm 13 years ago, it brought aboard as its first principal Justin Fishner-Wolfson. Having nabbed two computer science degrees from Stanford and spent two years as CEO of an organization that provides asset management services to the school’s student organizations, Fishner-Wolfson wasn’t shy about voicing his opinions at the venture fund. In fact, he says Founders Fund made a much bigger bet on SpaceX than it originally planned because he pushed for it.

He stayed three years before spying what he thought was an even better opportunity, owing to friends who worked at Facebook before the company’s 2012 IPO. They were beginning to look for ways to liquidate their shares, and while they had options, to his mind, they weren’t great. More, Fishner-Wolfson says he foresaw more companies like Facebook staying private longer. He said goodbye to Founders Fund and formed 137 Ventures to acquire secondary shares from founders, investors, and employees.

That was 10 years ago, and the firm seems to be doing just fine for itself. Last year, it closed its fourth fund with $210 million in capital commitments, bringing its assets under management to more than $1 billion. Its approach of focusing on roughly 10 to 12 companies per fund appears to be paying off, too. Since late September, it has seen three of its portfolio companies — Palantir, Airbnb, and Wish — hit the public market.

We talked at length with Fishner-Wolfson this week to learn more about how 137 Ventures works, from how it screens companies, to the impact it has seen from companies that are giving their employees longer windows in which to keep their vested stock options. (“It has certainly stopped the desperate calls from people who have huge amounts of equity that’s about to expire, which, I’m totally happy to not get those phone calls, because I feel terrible for people who are in that sort of situation,” he said.) We also talked about that early deal in SpaceX, which also appears in 137 Ventures’s portfolio.

You can listen to that longer conversation here. In the meantime, we’re pulling out part of our conversation that centered on Wish, the discount e-commerce company whose IPO this week has been called a dud.

TC: Two of your portfolio companies have done very well as they’ve entered the public market — Palantir and Airbnb. Wish was a different story, dropping in its debut. What do you make of its IPO? Do you think investors misunderstand this company?

JFW: I think it takes the investment community a long time to understand any newly public company. At the end of the day, the IPO is just one day, right? What really matters is how companies perform over the next 10 or 20 years.

I would look at Microsoft or Amazon or more recently, Facebook, whose [share price] dropped 50% in the week or two following its offering and Facebook has gone on to be an incredible business. I have no idea what the market is going to do tomorrow [or] the day after. But over a decade, if you can really build a great sustainable business that compounds, it all comes out in the wash.

Wish has done an incredible job of scaling the business. I think [cofounder and CEO] Peter [Szulczewski] is one of the best operators I’ve met in this industry. And they’ve done a lot of innovative things in terms of mobile. There’s a lot more discovery on the Wish platform. The whole in-store pickup has been really innovative; they’re helping consumers get products quickly in an asset-light kind of way where you don’t need to buy millions and millions of square feet of warehouses.

TC: You’re talking about these partnerships that Wish starting striking with mom-and-pop shops in the U.S. and Europe, where those who have extra storage space will now take receipt of Wish goods, which in turn gives them a little bit more foot traffic when people come in to pick up their items. That’s a big shift from how Wish used to operate, which was by shipping things very cheaply from China through a USPS deal whose economics have since changed. Is that right?

JFW: Right. They’re helping small and medium-size businesses drive foot traffic, which was always valuable but in the current environment, going to become even more important to these sorts of businesses. They’re [also] helping those businesses leverage the data they have across their entire platform because Wish understands what consumers in that geography are looking for, and they can help those businesses merchandise better. And then, because they’re shipping product to one location, they’re aggregating orders from a whole bunch of people who don’t know each other, and that reduces logistics and shipping time and costs. So they send that stuff in, and it’s easier for the consumer to walk or drive five to 15 minutes, and go pick it up. That allows Wish to focus on the value-conscious consumer who is willing to trade a little bit of time for a much better price on things.

TC: Wish is known as a place to get tchotchkes from China. Now that it’s trying to sell more mainstream goods, how does it go about changing the perception that it has in the marketplace?

JFW: I’m not sure they need to do a whole lot to change that perception, because I still think they haven’t penetrated the market as a whole. There are lots of people who don’t even know about them quite frankly. And as [I’ve] watched the marketplace evolve, you’ve just seen more and more merchants, and more and more data back from customers about both the merchants and the quality of the merchandise, and all those things feed back into this very powerful system, where they can leverage the data to improve product quality and make sure that they’re selling what people want.

TC: Do you think uneven quality explains the company’s uneven revenue? It grew something like 57% in 2018, then 10% in 2019, and picked up again in the first nine months of this year. Why do you think it’s been topsy turvy?

JFW: All businesses go through these cycles of growth, and then focusing on efficiency. If you just focus on growth, you tend to grow, and then break things, and then do things in relatively inefficient ways. And then ultimately, you need to turn around and focus on how you drive operational efficiencies. So I think the cycles that you’re describing, if you look at the underlying metrics, you [see] improvement in operating efficiency.

TC: Wish’s shares did not “pop.” On the other hand, former Snap executive Imran Khan told CNBC on Tuesday that the recent post IPO stock pops, including those of Airbnb and Doordash, represent an “epic level of incompetency” from the bankers who underwrote the stocks. Do you believe it was incompetency on the part of the bankers or just market volatility that caused those stocks to pop as high as they did?

JFW: I think no one actually knows the answer to that question. I think it makes for a good sound bite. At the end of the day, I don’t think the price on the first day is a meaningful indicator of anything.

TC: Are the feverish embrace of these companies driving prices up in the secondary market? What are you seeing?

It really does matter what the public prices are [because] that ultimately trickles into the private markets and also vice versa. At some point, things can’t have massive differences in value between their private market valuations and their public market valuations. So you definitely see multiples shift as the market shifts. But these things are often averages. People focus on one company or one example of these things without necessarily looking at all the companies because that would be quite difficult.

But there are always examples of things that are overpriced. There are also examples of things that are under priced. As an investor, you want to try to invest more of your money in the good companies that are on the lower end of that spectrum, certainly. But the focus is always on good companies. If you can find companies that are going to compound over long periods of time, as long as you’re not too crazy on multiples or valuations, you end up being in a good spot.

TC: Who are you tracking right now? What’s an investment that’s not up on your website yet?

JFW: Snapdocs [a company that helps real estate professionals to digitally manage the mortgage process and other paperwork and which just closed on $60 million in funding in October].

Aaron [King], who is the founder and CEO of the company, has done really a fantastic job of building a product that that people are willing to adopt, and this is the right moment in time for that growth to really accelerate. They’ve been having a good year.

Pictured above: The 137 Ventures’ team, with Wolfson center (in glasses).