Showing posts with label MATCHMAKING. Show all posts
Showing posts with label MATCHMAKING. Show all posts

Monday, August 10, 2026

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

Blind Faith in New Technology Is a Startup Trap. Customers Still Want the Same 4 Things

Buyers want to know what your product or service is going to do for them, plain and simple. The further you move away from that simple desire, the less likely it is to succeed.

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

Aug 10, 2026

 

We’ve all come to be such rabid believers in the power and ability of all kinds of new technologies that we think that blindly relying on the strength of our tech alone will be sufficient to get us over the goal line. Sadly, this has never been the case. It’s a necessary element to be sure, but never sufficient standing alone to get the job done and acting otherwise is just another trip down Memory Lane to the Field of Dreams where people swear that “if you build it, they will come.” Whom the “they” are is never that clear at the outset and unfortunately, it’s just as likely in some cases to be creditors rather than customers showing up at your doorstep if you’re not careful.

Interestingly enough, this attitude seems to be present even in new business ventures where the driving components for success have little or nothing to do with the underlying operating systems. And I’m not merely talking about the fact that every new investment deck I see these days describes business processes that are always AI-infused and enabled—need it or not. There is so much conversation and excitement about the connectivity that the web now enables—from rapid scaling to customer acquisition to engagement at little cost—that even the entrepreneurs pitching the programs lose sight of the other gating factors and the relatively substantial hurdles that their prospective businesses need to surmount.

Whatever else may have changed out there in the real world, it’s still demonstrably the case that my old formulation still holds. I’m just not that interested in any business which can’t show me in minutes one of the following:

·         How it’s going to save me time

·         How it’s going to save me money

·         How it’s going to make me more productive

·         How it’s going to help me make better decisions

An essential part of the foregoing is the “me” in the heart of it. Buyers want to know what your product or service is going to do for them – plain and simple – and the further your plan or idea moves away from that simple and selfish desire, the less likely it is to succeed.

This is why I was initially intrigued to see a recent PowerPoint deck that was sent to me in reaction to my recent column about venal and shameless matchmakers that describes yet another alternative solution to the failures and other shortcomings of the current online dating models. To be clear, there’s a big, ugly problem here waiting to be solved and a huge audience looking for a better solution than what’s currently on offer. Sixty million Americans still use dating apps, but they’re burning out at a frightening rate with three quarters of them quitting the services within a month. This doesn’t really bode especially well for any dating business pro forma because you lose the losers (who give up) and you lose the winners (who get dates) over relatively short time frames.

The approach that Kindred has come up with is basically to let your community play cupid and find you the right match. It’s all about who you know and who knows you and all those helpful Good Samaritans are gonna drop whatever they’ve been doing and volunteer to help find you a date and/or a spouse. I wish the founder well, as a lot of her proposal is drawn from her own background and painful experiences, but I took this proposal as almost a textbook case of how easy it is to miss some of the most basic selling propositions (what’s in it for me) and how hard it is to motivate relatively uninvolved and lazy people (who will always talk a good game) to actually assist you in building your business when they’re noy even the primary beneficiaries of the service you’re offering and they’re not getting paid.

The basic premise is that you’re building a system of middlemen and women (called here “validators”) and these folks (without consideration) are going to attempt to connect willing daters on the one side with theoretically interested daters on the other side by doing the homework, scouting around for prospects, building out profiles for other people, making intros and “vouching” for their candidates as they are tendered (no pun intended) to the interested daters. Many of those most in need of assistance are the least likely to admit and acknowledge that they need a well-meaning but intrusive third party’s help. Even the neighborhood spinster doesn’t want to be the specimen in someone’s solicitous science project.

Even forgetting about the necessity of reaching almost immediate critical mass on all three sides of this equation, you’re building a business on the premise that people who know likely prospects in their communities are going to undertake this entire new behavior—being a bride and groom broker—in the vague hopes that there’s an acceptable and attractive match out there somewhere for them to connect their friend, neighbor, relative or whatever with. And they’re also willing to assume and bear all the bad news associated with busted dates, bad behaviors, no-shows, and worse and the emotional and pointed repercussions. All for free.

As if. The truth is that nobody today is looking for more work and another time-consuming and tedious job which has all the hallmarks of being thankless as well. Eventually the hope is that the daters will eventually pay the freight for this service and presumably that the validators will have the heartwarming satisfaction of doing good deeds and helping love to blossom. In the early days, ads and events are expected to provide revenues before there are paying customers.

In addition, there is the nasty notion of plenty of existing cost-free alternatives all over the place that already seem to work fairly well for folks. It’s easy as pie to check out a prospect on social media these days and say yea or nay to a fix-up without ever incurring any risk, cost, exposure, discomfort or embarrassment. A good entrepreneur’s job is to find a real pain, make sure that a wide population of potential customers accepts and acknowledges the pain and is ready and willing to pay for the solution, and then to develop an offering that brings all of the interested parties together cost-efficiently and relatively painlessly.

The bottom line is pretty simple – people don’t change when they see the light, they change, if at all, when they feel the heat and this business feels like well-intentioned cold potatoes and not a hot meal.

 

Tuesday, July 28, 2026

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

Rich, Busy, and Clueless: The New Clients Fueling a $250,000 Matchmaking Boom

Technology has made the matching process ever easier, which has had a mixed impact.

 

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

Jul 28, 2026

 

 

In the decades before the scourge of the pandemic, admitting that you met your mate through a marriage broker or an online dating service was generally regarded as a confession of behavior somewhere between despair and desperation. It wasn’t as bad as buying a mail order bride or marrying a pen pal who was in prison for life, but it could still raise eyebrows. Blind dates, hooking up and one-night stands were all deemed to be acceptable youthful behavior and not expected to lead anywhere anyway. But marrying someone you met on Match.com just wasn’t something you bragged about to your friends and neighbors. It smacked of having no other choices and settling for someone equally at wit’s end.

However, Covid-19 gave millions of cellar dwellers and wallflowers permission and the opportunity to actively seek out companionship and even more substantial commitments in online forums and dating services where they wouldn’t have otherwise been caught dead. And to be clear, it was no longer confined to any particular age group or gender. It wasn’t as pristine as Tom Hank’s and Meg Ryan’s romance in You’ve Got Mail, but at least it was no longer perceived as pathetic. But the whole matching process—finding your future on your phone—was never really accepted and always regarded as déclassé.

Technology has made the matching process ever easier and easier which has had a mixed impact. Initial connections were much simpler to secure because there were millions of people in the database, but at the opposite end of the martial spectrum, equal millions of would-be romances and suggested introductions were immediately thwarted by tech-enhanced critical scrutiny and rejections resulting from a quick scan of a prospect’s online persona. There’s a persistent FOMO-like sense among online searchers that a better bet and a more attractive match are just a swipe or two away. So, they keep searching and coming up empty. After all is said and done, the bottom line has never really changed. Many people still think looking for love online is for losers. This persistent attitude and a consistent lack of results have led to user fatigue, disappointment, and large-scale abandonment of the online services. And it’s created a resurgent demand for face-to-face personal matchmaking services.

As a result, and notwithstanding all of the subtle and not so subtle opprobrium, the U.S. matchmaking industry has rapidly expanded to meet that demand. It now numbers over 2,000 “professional” firms of various sizes and of widely different skill sets, experience levels, and even pricing models. This number is, of course, substantially supplemented by “helpful” parents, friends and other family, know-it-all neighbors and yentas, and plenty of intrusive experts at the office.

But the real explosive growth in the business—more than two-thirds of the newer firms—has come from corporate chains expanding nationwide, much like the model of H&R Block. These numerous and readily accessible players occupy (and have actually already overcrowded) the lower segments of the marketplace. Their stated efforts to use technology and now AI to professionalize and standardize a very sloppy, unregulated, and chaotic industry have mainly resulted in dramatic price increases for their basic standardized and turnkey services. These price hikes combined with a Wild West environment without rules or regulations regarding any player’s behavior, promises, representations or performance guarantees have brought the expected onslaught of crooks, con men and scam artists – all enabled by A.I. and the awareness that no civilian, client or customer can ever tell what’s really inside of their black box. High demand, high prices, an ignorant and gullible customer base, and no applicable laws make for an environment ideally suited to cheats and criminals.

But technology has also been inadvertently responsible for the expansion of a singular high-end segment of the match-making business which has thrived in the new environment—especially on both coasts and in D.C.—by offering previously unimaginably high prices for their personalized and customized services. Their specific targets—rarely overtly stated—are tech-created rich nerds looking for love with huge gobs of cash, no time, no class, and no clue as to how to proceed to find a partner.

And there are lots of new mini-millionaires like these being created every day by AI IPOs and the expiration of all manner of lockups and other trading restrictions, especially around crypto deals. They literally have more money than they (or their parents) have ever had in their lives and almost no ability to evaluate which of these firms might make sense for them to employ in their quest.

So, in the time-honored tradition of the very best tech promoters and marketers, these poor suckers fall back on the stupidest rationale of all: How can it be bad if it costs so much? Worse yet, there’s clearly a Veblen effect as well which dictates that higher prices for luxury or scarce goods increase the demand rather than reduce it. And finally, there’s clearly a FOMO effect which the high-end and high-priced personal matchmakers make very clear and that is that their time and resources are limited, the number of great men or women out there who are looking is a finite number, and waiting will never get you anything worth waiting for.

The bottom line: the highest-end boutique players in this very narrow field are perfectly comfortable charging rates between $50,000 and $250,000 for their services with no strings and no guarantees attached. They serve executives, high-net-worth individuals, and successful entrepreneurs. And they’re getting these kinds of numbers and growing their revenue every year. It’s all legal for now, but I guess the real question—like so many Trumpian actions these days—is should it be legal?

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