NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

That Airport Charging Station Could Be Hacking You. Here’s How to Stay Safe

Ignorance is bliss until it bites you in the ass.

EXPERT OPINION BY HOWARD TULLMAN, GENERAL MANAGING PARTNER, G2T3V AND CHICAGO HIGH TECH INVESTORS @HOWARDTULLMAN1

APR 14, 2026

Photo: Getty Images

It’s hard to know these days whether the greatest risk to our personal and financial security is laziness or ignorance. I’d say it’s a tossup but, while ignorance is theoretically curable (perhaps not for team MAGA), laziness is a lifelong curse. Worse yet, if you’re too lazy to learn, you’ll never be free of your own ignorance. So many of us, even apart from politics, choose the blissful comfort of ignorance over the inconvenience of painful truths. We go through life with our fingers crossed just hoping and praying that bad things won’t happen to us. But hope is not a strategy, and we have to stop kidding ourselves and admit that knowledge, for better or worse, makes life messier.

One of the problems we’re facing with the rampant spread of all kinds of new technologies is that—in far too many cases—we don’t even understand that our mundane, habitual behaviors now represent dangers that we could have hardly imagined a few years ago. Real knowledge gives us the ability—if not necessarily the will or desire—to recognize and acknowledge the extent of our ignorance. The recent announcement by Anthropic that its latest AI model is too powerful to trust to mere mortals is just the latest warning that the world is likely to shrug off as more tech hysteria. The time has come to overcome our studious obliviousness and at least listen to the folks who know better.

We decided long ago that we were willing to sacrifice a great deal of our privacy for immediate access and convenience in virtually every aspect of our social and shopping activities. Virtually everyone suffers from the stupidity of employing the same simplistic password or phrase multiple times for access in various applications and accounts that we use regularly. And today we hear jokes all the time about people using the word “password” for their passwords. On average, each household has about 100 critical passwords for their many accounts and services and experts estimate that more than half of those are the same word or phrase. Google and Microsoft systems regularly alert users to the fact that they have multiple identical and common passwords or that their codes have been included in data breaches or other dark web listings. But, because we’re all too busy or too lazy, we almost never take the time to update and change them.

Now we’re seeing several new threats which don’t rely so much on new or exotic technologies as they do on our habits, typical actions and behaviors, and the fact that we have reached the point where we take far too many conveniences for granted and never even consider that they might pose security risks. We’ve seen this problem for years now with crooks inserting skimming devices in ATMs and other card readers in order to steal credit card numbers. But now our increasing reliance on ubiquitous connectivity and shared infrastructure is presenting a whole new level of exposure and risk.

We don’t give one second’s worth of thought to plugging in any of our devices to any available power outlet. We’re just grateful they’re there. But when public USB ports and power stations began to be deployed in airports and elsewhere, the focus was 100 percent on location, access and convenience and not a bit on security. As a result, a new threat—juice jacking—which is based on our incautious use of public USB ports to charge our devices can lead to compromised equipment, data theft, and the insertion of malware in moments. When we’re in a hurry, distracted, and grateful to find a source before we hop on a plane, no one’s thinking about data loss, identity theft, or worse. But in doing so we’re all sharing a common port and an anonymous connection.

As Eric Plam, the CRO of SIMO says: “The safest move today is simple—don’t share infrastructure with strangers.” SIMO makes portable and powerful devices which supply both power and secure dedicated Wi-Fi connectivity for mobile workers and especially for travelers. And to be clear, these kinds of risks aren’t limited to power concerns. SIMO’s devices also address another new connectivity problem which is the growing development and deployment in public spaces of imposter Wi-Fi networks.

Plam calls these “evil twins.” They look very much like a legitimate network that we’re all familiar with and to which we readily connect without taking a moment to verify anything. In fact, we’re pleased that we see a rapid connection and, where necessary, that our password is accepted (along with anyone else’s). Once the connection is made, your messaging, transmissions and other traffic can be intercepted, your credentials captured, and you can even be sent to other fake or spoofed sites. There’s no magic here or complex technology, it’s just a case of crooks riding on our typical conduct and routine actions.

Avoiding these threats isn’t hard once you’re aware of them, but habits are ridiculously difficult to break or change. Moving from using public facilities and infrastructure to reliance and use of a secured and trusted private connection is clearly the way to go and, frankly, cheap compared to the likely costs of losing your data or your identity. SIMO suggests a few other basic steps for travelers to take:

(1)  Avoid public Wi-Fi for sensitive activity

(2)  Verify network names before connecting

(3)  Disable auto-connect on the road

(4)  Use wall outlets rather than USB ports

(5)  Carry a power pack whenever you’re away from home or office

(6)  Use a Solis Go secure Wi-Fi + Power Bank

(7) Always enable two factor authentication for all sites, services and apps

(8) Use a security key such as a Yubikey especially for work-related computing

Ignorance is the absence of knowledge. Stupidity is the rejection of knowledge. Now you know. Forearmed is forewarned.

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

Unsubscribing Will Only Get Harder in the Age of AI. Don’t Let Your Company Be Part of the Problem.

The price doesn’t matter when you’re the product.

EXPERT OPINION BY HOWARD TULLMAN, GENERAL MANAGING PARTNER, G2T3V AND CHICAGO HIGH TECH INVESTORS @HOWARDTULLMAN1

JAN 12, 2026

Illustration: Inc; Photo: Getty Images

With the arrival of the New Year has come the inevitable onslaught of renewal requests, demands, entreaties and, of course, the slippery automated extensions designed to slip under the radar and convert low-ball promotional offers into full-bore subscriptions. Along with these ploys, and arguably as a product of them, come the seductive ads from subscription clean-up companies like Rocket Money which promise to quickly display on a single screen all your subscriptions—many of which they suggest with good reason that you didn’t even know you still had—and which their system will magically cancel at your direction and thereby save you grief, effort and hundreds of dollars as well.

You can decide for yourself how valuable and effective services like these are (Rocket claims to have saved its members over $2.5 billion) and do the cost-benefit calculation for yourself as well, but to be clear, they’ve clearly identified a serious problem which afflicts millions of us every year. And, needless to say, the magazine and service vendors themselves are the last businesses likely to or interested in informing you about your wastes of money.

Aside from the dollars saved, the real benefit (if these services work as represented) is that you avoid the pain, wasted time, and harrowing hurdles of trying to wend your way through the chutes and ladders, hoops and mazes, chatbots, and flat-out dead-ends in order to attempt to cancel these things on your own. And even if and when your journey finally delivers you to a human being or a chat window manned by a real person on the other end, you discover that you’re actually far from home free, unless you have a very thick skin and the ability to be unbelievably rude to some poor fool tasked with making you a series of increasingly desperate financial offers to retain or extend your subscription.

It’s pretty clear that these sad people who are actually paid to not take “No” for an answer have an entire set of scripts that they employ, and the tactics they use rarely vary much between companies. The standard ploys include guilt-tripping or otherwise shaming the subscriber, intentionally misunderstanding or misinterpreting the customer’s statements and desire; understating or concealing costs or terms, and dishonestly explaining the associated consequences and difficulties which may arise from a cancellation.

The only good news is that the Federal Trade Commission (largely pre-Trump II) has cracked down on many of these actions and operations in the traditional paid subscription and boiler room world, which has always been largely an analog operation and remains so today. The bad news is that there’s been a substantial gap in terms of acknowledgment of the similar concerns and in any enforcement in the new digital world of social networks (which are frankly far more addictive than any print magazine) where even the idea of “subscriptions” isn’t exactly applicable. And the matter is made even worse when there’s no payment involved. Regulators and legislators have had difficulty understanding the nature of the harms associated with the intended and manufactured difficulty that exists in cancelling “free” memberships or voluntary participation in social networks and in other especially addictive services like TikTok.

Of course, we’ve all learned by now that the reason you’re not asked to pay for your Facebook or Instagram or Messenger memberships or services like TikTok is that it’s your attention and mindshare that’s being sold by the tech companies to marketers, advertisers and politicians. The price doesn’t matter when you’re the product. This is the reason why it’s not simply been in the economic interests of Facebook and the other social networks to make it hard to quit; it’s a conscious, intentional and pernicious part of the underlying design and economic model of these businesses. And frankly, it’s far harder to drop these services or cancel your memberships than anyone would imagine until you’ve tried.

It can take as many as eight or more discrete steps (and the ability to ignore suggestions, blandishments, warnings about losing friends and other functionality and services) to finally reach the final stage where you can actually cancel your Facebook profile. The government has begun to work with some of the states to get a handle on this situation, but it’s slow going and nothing regulatory is likely to move rapidly over the next three years of Trump’s rule.

This may all seem like a relatively minor concern apart from the continuing damage all these services are doing to our kids, but that’s not the main reason I’m raising the issue. No matter how many times new technologies bite us in the collective ass because we launch and implement them before we fully understand their impact or consequences, we never seem to learn the lessons. Indeed, humans can ruin the spirit of just about anything if given the time and technology.

Right now, when nothing in our lives is more omnipresent and potentially threatening than AI, we’re learning that the tech guys have done it to us again. Facebook has built its AI chatbot into Instagram and WhatsApp, and there is no option to turn it off. Google searches result initially in an A.I.-generated result, and the stats already make it clear that the vast majority of all searchers never go beyond that first level quasi-generic answer to their queries. Even more problematic, Google has massively updated Gmail (3 billion users worldwide) and embedded its Gemini AI across the entire platform so the AI system will be reading all your emails whether you like it or not or, more importantly, whether you even know that it’s happening. Of course, if you are aware of this change and a complete gearhead, there’s an onerous multi-step process to shut the service off but, here again, you’ve got to know about it, find and implement it, and recognize that in doing so you will lose some other desirable and longstanding Gmail functionality.

The bottom line is that more and more of these new technologies are not being offered to new business builders as choices or options but instead are imposed on them whether they like it or not.  Only two industries call their customers “users” – tech software vendors and drug dealers.