This week on the podcast, we’re joined by Gita Gupta, VP, Director of Emerging Technology and Digital Economies, Global Technology Risk Practice at Lockton, and we go deep on all things risk, insurance, and fraud: three words that might make founders’ eyes glaze over… right up until they’re eating your company alive.
Whether you're scaling a delivery platform, launching a micromobility fleet, or building the next generation of autonomous vehicles, your biggest threat might not be competition — it could be what’s hiding in your terms of service, rider behavior, gig workforce or payout liability. From staged crashes to underinsured drivers, bad actors and blind spots can break even the best product.
Gita walks us through the biggest risks emerging mobility and logistics companies face, how insurance can be strategically positioned, and what founders often get dead wrong about coverage. It’s part cautionary tale, part tactical playbook—and essential listening for anyone building in this space. Because at the end of the day, if you don’t understand risk, you (and your investors) can’t understand your business.
We’ve also got a few more fun items on this week’s show: Greg and I veer from AVs to politics, and the Zag Daily crew heads to Eurobike for the latest and greatest on two and three wheels.
HOT INDUSTRY NEWS & GOSSIP
🧨🧨🧨 Today’s news roundup is a bit on the shorter side, giving folks some time to go start their Fourth of July celebrations a tad early. That said, we’re not sure how much cause for jubilation there is, with the “Big Beautiful Bill” on the precipice of passage. We’re gutting our ability to build infrastructure, depriving millions of healthcare and food subsidies, tying down the next generation with increased student loan costs and generally foreclosing our nation’s future fiscal capacity to respond to real crises, and for what… to lower top marginal tax rates and spend more on terrorizing immigrants? I understand this newsletter has readers of all political stripes, so if anyone has an honest defense of how these trillions of new debt better the country, please reply with your assessment.
Is that complete street actually completed? Smart Growth America released its 2025 rankings of the Best Complete Street Policies, noting that top scores are down since 2023. The highest performing cities are San Antonio, TX; Nashville, TN; Clyde, OH; Bluffton, OH; and Boca Raton, FL. Given that in my experience most streets in Nashville look like this, perhaps it’s time to stop celebrating policies that never actually make it beyond the paper?
Smart curbs in steel city: New data out of Pittsburgh shows just how effective good curb management can be. PGH now has smart loading zones in 75 locations, boosting traffic speeds 4.5% and cutting down on double parking by 95%.
I-feel-a for them… Sony and Honda’s EV joint venture is racking up deep losses — ¥52 billion ($362 million) — ahead of its initial vehicle’s debut: the awkwardly named Afeela 1. Targeting a starting price of $89k, the vehicle won’t initially appeal to the masses, but it’s nice to see a new EV come to market that’s not a lumbering 10,000 pound SUV…
SEP-TA-puku: Philadelphia’s transit agency just passed a “doomsday budget” that slashes service by 45%, effectively eliminating a number of train lines and eviscerating weekend service. Expect to see a lot more of this as federal funding dries up, and purple states dither on whether to backfill those dollars. Relatedly, Florida just cut funding to a long gestating plan to bring commuter rail to a string of coastal cities.
The train to somewhere… Metrolink — Greater LA’s commuter rail network — is revising its fare structure: getting rid of round trip tickets, adding a $5 day pass and other incentives to match changing traveler demographics. Combined with other recent changes like more mid-day trips, the railroad is looking to better serve riders now that 9-to-5 downtown office workers seem to permanently work from home a few days per week; more ambitious programs like SCORE and through-running tracks will further those efforts. Meanwhile, LA Metro’s light rail expansion to the eastern edges of the county are nearing completion, with the dedication of new stations in Glendora, San Dimas, La Verne and Pomona. The A Line is already the world’s longest light line; given the amount of grade separation it’s more useful to think of LA’s LRT network as akin to an S-Bahn.
Newber: Uber just released a slew of new features, just in time for the summer travel boom. Say hello to Uber Share (née Uber Pool) at more airports, enhanced options for getting food delivered to your hotel room, smaller airports getting access to Reserve Pickup and a new partnership with Delta and Amex.
Beep goes deep (South): AV operator Beep just launched in Jacksonville, FL; going live with kitted-out Ford Transit vans in the city’s downtown. Concurrently, the startup raised $52.7M for its approach to autonomous micro-transit. Real geeks may recall that JAX has an even more impressive piece of autonomous technology: the now basically-defunct Jacksonville Skyway people mover.
See ya, CEQA: Will this be the legislation that finally uncorks housing production in California? As part of the just passed state budget, Gov. Newsom signed off on a big regulatory reform to CEQA, the state’s iconic environmental law. Originally passed by Governor Reagan to protect wild lands from freeways and other large public sector infrastructure projects, it has since morphed into a cudgel used by the likes of the oil industry to fight for continued pumping and NIMBYs to sue developers of new buildings over perceived harms like shadows. This new bill — championed by Assemblymember Wicks and Senator Wiener — will help with the latter, exempting most urban infill housing from CEQA challenges.
Has Adams finally delivered? Almost a year and a half after it was first announced, NYC’s city council and (likely outgoing) Mayor Eric Adams have finally funded the Department of Sustainable Delivery, allocating it $6.1 million of the city’s $116 billion annual budget. Full details are still scant, but we know the office will sit within the larger Department of Transportation and host 60 positions for regulation and enforcement.
Still golden: California’s overall share of venture funding rose to a modern record: 68% in H1 2025, per Crunchbase. There must be something in that (desalinated and/or drained from the Sierras) water!
Curves over curbs: Admittedly, this isn’t an architecture blog (if only!) but we’d be remiss if our thoughts on transportation didn’t veer into occasional reviews of the built environment. We’d like to offer a hearty cheer to Peter Zumthor’s undulating new gallery space for LACMA; previewing the space over the weekend as Kamasi Washington filled it with jazz was a borderline magical experience. While the structure floats above LA’s premiere thoroughfare, offering enticing light and brooding darkness, we’ll need to wait to see how well the building’s feet interact with the street below.
A few good links: Dara Khosrowshahi (CEO, Uber) and Alex Kendall (CEO, Wayve) discuss autonomous vehicles. A very deep research report on Waymo’s operations. Chinese ridehailer CaoCao raises $236M to take on Didi. Meet Raleigh’s eye-catching new e-bike. Third Lane Mobility gears up for growth. Ilus shows off modular micromobility hardware. Regent’s seaglider completes first crewed foil-mode test. Travel-tech firm Navan preps for IPO. An upcoming wave of lease expirations could see many more cheap, used EVs hit the market. Colorado Springs releases curb management plan.
Enjoy the hotdogs and colorful explosions!
- Jonah Bliss & The Curbivore Crew
Share this post