Beware of AI Cons Targeting Entrepreneurs
AI is creating a tsunami in our inboxes. As founders, entrepreneurs, and startup CEOs, we are particularly vulnerable to certain types of scams — and I have noticed a major uptick in volume over the past year or so. Let’s talk about what these new cons look like.
No doubt we are all inundated with scams on many fronts in our daily lives. The text from the U.S. Postal Service that needs extra info to deliver your mail? The text claiming you owe a road toll in a state with no toll roads? The high-pressure contact insisting you must act immediately to protect your account, avoid arrest, or face some other outlandish consequence? The email offering to pay you a bundle to facilitate a transaction with a foreign prince? Hopefully, by now, we have all gotten good at recognizing these scams and simply stopping, deleting, or hanging up without getting sucked in.
However, lately I have noticed that some of these cons are getting far more sophisticated — and they are beginning to prey specifically on vulnerable people in our entrepreneurial ecosystem. I count myself among the “vulnerable.” Why? Because I am visible, want to help, am open to new Board-level career opportunities, and am always looking for resources to support the early-stage companies I am involved with. Let’s break this down to see what these new scams look like.
Entrepreneurial leaders are being targeted by scammers with increasing frequency. While I don’t have hard incidence numbers, I can say that the volume and sophistication seem to be really taking off since AI chatbots burst onto the scene. In the last year, for example, I have found myself and others targeted in new and sneaky ways — and I have had to sharpen my ability to identify and bail out of these cons. For example:
- Big Money Investors Ready to Move: Fundraising is rarely an entrepreneur’s favorite activity, so anything that appears to expedite the process is attractive. Furthermore, it is not uncommon for entrepreneurs to become genuinely desperate to get funds in the door — and that desperation makes them more vulnerable to overlooking subtle warning signs, hoping that maybe this one is real because a substantial cash infusion can be such a game-changer. Outreach from various parties purporting to source “deals” for interested investors hits my inbox every few days — and sometimes it passes the first few layers of the sniff test. More than one entrepreneur has been drawn in by a series of escalating interactions that seem like legitimate early screening: an email or LinkedIn message, a short Zoom call, a follow-up meeting with a colleague, an in-person trip, and negotiations that seem too easy — or where the “potential investor” actually wants less favorable terms than expected. These approaches often come with convincing but faked websites, fabricated investor data rooms with excessive disclosure, and business addresses that do not check out (listed as available for lease, for example).
- A Perfect Career Opportunity: Entrepreneurial CEOs and other startup leaders are often approached by strangers — recruiters, for instance — about new career opportunities, and sometimes we are genuinely interested. (I enjoy my work as a public Board member and would certainly explore adding a second Board seat if it were a great fit.) Like outreach from those claiming to know investors, my inbox is also full of messages like “Are you interested in an opportunity like this?” or “I represent a company that is looking for someone with your background.” Many are likely hard-working recruiters trying to make a genuine match. However, I have uncovered fake recruiters using a retired recruiter’s LinkedIn photo and name to pass an initial sniff test, pretending to represent a privately-held company that nominally seemed like a good fit, and then recommending a consultant who could help polish my materials — for a fee, of course. I am grateful for the generosity of other CEOs who, when I asked whether they were really working with recruiter X, replied, “Nope! We are not recruiting for any such position. It’s a scam!” — which also told me these schemes are far more widespread than I had realized.
- Author Assistance: As a blogger since 2020, I am continually amazed by how frequently I receive “offers” of help to monetize and promote my blog — all for a fee. Eventually, I blocked most comments on my site because these solicitations had become the vast majority of messages and, frankly, clearing them out was a waste of my time. In all likelihood, many of these solicitations are AI-enabled author scams, as described in detail in a recent article by a far more accomplished author than I. Fortunately, I am clear in my own mind about why I write: it is to help other entrepreneurs. I am not trying to monetize my blog, nor am I drawn in by the frequent offers to help me become a book author (certainly after I had previously read this wonderful Seth Godin post that convinced me that becoming a book author was likely not worth my energy!).
So what makes entrepreneurs vulnerable to these particular types of cons?
- We are visible. Entrepreneurs put themselves out there to raise money and promote their ventures — especially digitally. This means scammers can find us and our contact information.
- We are vulnerable. Building a new venture is hard. As an entrepreneur, you need to gather resources — funding, clients, team members — and it is genuinely difficult to break through to those who might be interested. This makes us susceptible to people who claim to have what we need: access, connections, and opportunity. They are often strangers rather than people we know personally, which makes them harder to vet.
- We are time-constrained. An entrepreneur’s most precious resource is time. Anything that appears to leverage that time and boost access is worth a look. Yet the very thing that makes an offer attractive — apparent time efficiency to someone without enough time — is the same thing that makes it hard to dig deeply enough in due diligence to determine whether it is legitimate. And the more sophisticated these scams become, the harder you have to work to expose them.
Watch Out For (doubtless an incomplete list)
- Anything “too good to be true.” If it looks like a really sweet deal, it probably is not legitimate. For example, access to secretive family offices supposedly eager to deploy millions into early-stage startups — while not impossible — is unlikely. This scenario also allows the scammer to invoke the “understandable privacy demands” of wealthy families to make due diligence harder to conduct than, say, checking out a venture capital firm with a public website, a known reputation amongst your real-world contacts, and a robust Pitchbook profile.
- AI-generated written communications. Chatbots have a tendency to mirror back the prompts used to generate that “personalized” email, making it feel as though the sender is genuinely engaged. Normal humans don’t communicate that way — nor do they endlessly praise how insightful your last message was. Ask yourself: does this communication feel like a real person, or a polished bot-generated message?
- An unwillingness to communicate live. Is the person unwilling to get on a phone call or a Zoom meeting? While I have encountered sophisticated scams involving multiple people willing to meet via Zoom, in person, and over WhatsApp, simply asking to talk live has exposed quite a few. When someone is supposedly offering a substantial investment or a high-value introduction, yet is too busy to speak with you directly, that is a significant red flag. A legitimate investor or recruiter would almost certainly want to vet you first.
- Weak due diligence. Anyone who wants to hire you or invest in your company will have a lot of questions. Expect a rigorous vetting process on par with other investment or career opportunities you have pursued. If the process feels too easy, the questions too light, or the interaction too limited — that should raise concerns rather than relief.
- Dealing only with a representative late in the process. The purported go-between could be a recruiter, a broker, a family office manager, or some other intermediary — someone who is not the actual decision-maker. Such roles do exist in legitimate contexts, which makes the setup plausible early on. But look for signs that the relationship or the asks are not what they should be.
- An international component. Someone seemingly representing a foreign investor or opportunity can subtly encourage you to second-guess your own judgment, since it is easy to assume that oddities might simply reflect different business norms elsewhere. Being asked to travel to Europe at your own expense to secure a transformative investment is a subtle way for a scammer to make it psychologically harder for you to walk away later.
- Crypto. Legitimate investors do not focus on deploying capital in cryptocurrency, nor do they ask you to pay fees in crypto. Standard U.S. dollar transactions through normal banking channels are the norm in business-to-business dealings. Regardless of the rationale offered, the introduction of a cryptocurrency requirement should be an immediate red flag.
Bottom line: be cautious when someone unexpectedly reaches out with an offer that seems perfectly aligned with what you most want. Search thoroughly — clicking every link — because it is often the deeper links and cross-references, not the glossy homepage, that start to smell fishy. Listen to your inner voice when something seems too good to be true, and run the scenario by an experienced peer or mentor. Do not become too invested in the “opportunity” as interactions unfold; sophisticated scammers may take days to respond or involve more than one party, subtly lulling you into believing this might be legitimate. And if you grow genuinely suspicious, walk away — regardless of how much time, energy, or money you have already put into the process.
Remember, no one wants to admit they missed the early signs of a scam. Unfortunately, AI is making detection harder every day, which is exactly why it is worth talking about these things openly — so we can all keep getting smarter.
