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?

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

Microsoft’s Massive Xbox Downsizing Signals the Brutal Reality of the AI Revolution

We’re beginning to see the secondary and other follow-on impacts of AI.

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

Jul 14, 2026

 

Sony’s PlayStation has been the global market leader for years, while Microsoft’s Xbox has been a distant second even after failed attempts by Microsoft to make its games a visible presence in the desktop world, where it clearly dominates the office installed base worldwide. Both Sony and Microsoft missed the migration of gamers to small mobile devices, where Nintendo prospered for a while—even before the phone revolution completely changed the video gaming space.

Now, we’re in the early innings of another sea change where the major tech players in the gaming industry are realizing that they no longer need armies of programmers, designers and developers to build and deliver the next generation of games. This is due to AI, of course, but also because the new games—mainly mobile—will be so lightweight and rapid as a result of the AI enhancements that there will be no need for any kind of bulky and costly game boxes or platform devices. Finally, as is the case across dozens of industries these days, the cost of the chips used in these boxes has been driven skyward by the adjacent and competitive demands of the AI companies for product that has cut into margins and may ultimately result in price increases at the worst possible time.

The latest salvo in this latest war of enforced attrition was last week’s announcement that Microsoft was making major changes in the Xbox video game business which entailed specifically cutting the Xbox workforce by 20 percent—about 1,600 employees now and another 1,200 plus over the next year. More importantly, the company is largely exiting the studio space, where it spent billions on expensive acquisitions not too many years ago.

The personnel growth in the MSFT games division was massive while the overall demand, player base and playtime all decreased substantially. It turns out—as with many other pre-phone and streaming activities—that millions of gamers would rather watch the play of truly talented players on YouTube than be second-rate participants in multiplayer competitions or simply play older games at home by themselves.

As far as the various studios are concerned, a few big ones like Activision Blizzard will shrink but remain, some others will simply be shut down, some are being encouraged to spin off and go off on their own with temporary support and assistance from Microsoft, and a few will remain until they too can be responsibly booted one way or another or quietly sold off to other buyers who right now seem to be few and far between.

But the most important takeaway from this highly visible and intentional effort at downsizing one lagging division to help offset enormous commitments and investments elsewhere in the enterprise—particularly in AI capabilities—is that we’re beginning to see the secondary and other follow-on impacts of the AI revolution. Thousands of Microsoft employees didn’t just lose their jobs because the AI tools could build new games, faster, cheaper and even more compelling than the former workers, they were also directly dismissed because the sales, marketing, manufacturing and promotion efforts of the entire video game division were shrinking and Xboxes were losing share and playtime as the gamers went elsewhere and the old boxes lost their sway and value.

This is only a single example, but I fully expect that we’re about to see many other industries rapidly roiled by similar advancements in process and speed or response time which will permit—in the name of speed, efficiency and massive cost savings, the wholesale elimination of entire groups and departments in businesses which will simply no longer be necessary because all of their functions in the value-creation chain will be substituted for with new AI-infused technologies. I’ll be writing shortly about a staggering combination in the advertising industry that brings together two powerful technologies and will completely upset and reorganize the ad creation business into a faster and cheaper system, which will also create more engaging and effective products.

It’s clear that a new form of M&A is already actively helping to connect and combine disparate companies with tools and services that are addressing common overarching problems in industries like advertising, and it’s also clear that these individual companies aren’t likely to build end-to-end systems by themselves in a timely fashion whether through lack of capacity or all the necessary resources or because they have been so deeply focused on solving their segment of the overall solution that they didn’t realize that a better and more robust and compelling solution could be offered by combining multiple offerings into a single comprehensive process.

 

HOWARD TULLMAN JOINS LISA DENT ON WGN RADIO TO DISCUSS TAILSAFE

 LISTEN TO THE SHOW HERE

LISTEN TO THE SHOW HERE

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

Ikea Is Making a Massive Customer Service Mistake, and It’s a Warning for Every Modern Business 

Companies that hand off critical moments to third parties to save a few bucks are sacrificing future sales and brand equity.

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

MAY 5, 2026

In the not-so-distant past, and long before the carefully crafted legends of Nordstrom’s in-store customer experiences spread far and wide, the state-of-the-art in the consumer retail business from a customer service and satisfaction standpoint was Chicago-based Marshall Field’s, which was later folded into Macy’s.

There were myriad stories passed down through family generations of how Field’s would accept years-old goods for no-questions-asked returns and refunds, how every fall, senior staff from the store would ride along with their delivery drivers to personally oversee the seamless delivery from storage of important clients’ furs and other winter garments, and how expert tailors, seamstresses and jewelry specialists could clean, repair and restore virtually anything for their clients as they worked tirelessly in their underground ateliers and craft workshops.

This kind of demonstrable commitment to end-to-end customer satisfaction and thinking far beyond the immediate sale toward a long-term and loyal relationship—and the entire organization’s willingness to go above and beyond the basics to deliver whatever was required—was built on decades of exemplary service, a powerful brand promise, and a culture where every expected action was a personal commitment, a one-to-one connection, and an obligation to do things right, start to finish. No sale was complete until the buyer was 100 percent pleased. The result was the kind of consistent customer loyalty and exceptional degrees of customer satisfaction that every new business dreams of. It was driven in no small part by a strategy of vertical integration and across-the-board accountability so that the entire process was under consistent supervision, direction, and control.

Today, even some of the most well-known companies with high-quality products, like Ikea, spend millions of dollars promoting their image and product quality and then totally drop the ball when it comes to support and delivery. They seem to fail to understand that every step in the process is critical. Nothing is more important to a completed sale than a smooth and successful delivery and a competent installation, especially when you’re dealing with bulky, complex, and expensive goods, including furniture of all kinds, onsite and in-home assembly of storage units, and connecting large-scale electronics. As amazing as it seems, and rather than making this a strong source of positive competitive differentiation (as other vendors in the same space, such as ABT and Wayfair, have done), Ikea has farmed out the entire delivery process to third parties.

Worse yet, Ikea washes its hands entirely of any responsibility for their delegees and their results and outcomes. It’s hard to get someone to answer the phones or follow up on delivery, and it seems like the left hand has no idea what the right hand is supposed to be doing. It’s unfortunate and unhappy customers are stuck in a whirlpool of denial, indifference, and finger-pointing, wherein no one at Ikea makes any attempt to resolve any difficulties or performance problems. They lay all the blame on Task Rabbit, which might just as well change their name to Trash Rabbit or Task Rubbish.

By farming out their future connection and severing the customer connection at the very worst point in the process, they’ve just become the latest business to believe that the “savings” from incorporating the often untrained, incompetent and indifferent minions of the gig economy into their delivery system are worth the damage to their brand and reputation as well as the psychic injury and actual harm done to their customers. There aren’t too many ways that a lazy moron can mess up a pizza delivery, but there are a million ways that some part-time installer can ruin a brand-new wall unit, misalign or otherwise damage hinges, handles, and closers, or simply rush through an assignment and do a half-assed job.

We’ve heard for years that you never get a second chance to make a first impression, and while that’s largely true, the more important consideration is that the most lasting impression, reaction, and feeling that any customer has is the final touchpoint, which is always the delivery. Companies that hand off that critical moment to amateurs and untrained third parties to save a few bucks are sacrificing future sales, positive word of mouth promotion, and vast amounts of brand equity.

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

The Next Big Membership Business Might Be a 24,000-Square-Foot Indoor Dog Park With a Bar 

The U.S. pet market is relatively recession-proof and should top $160 billion in 2026.

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

APR 27, 2026

Illustration: Inc; Photo: Getty Images

It’s hard to find anything good to say about the pain and isolation that so many people suffered during the pandemic, but for pet owners and especially single men and women, it was an amazing opportunity to head outdoors and safely meet with your neighbors and their pups, as well as interesting strangers on neutral turf with no strings attached. Pet adoptions during Covid were through the roof, and for many of us, our animals were worry sponges. Also, because work from home has now seriously taken root in more than 35 percent of all working households, millions of folks have been able to keep their new best friends and make them a major part of their daily activities and especially of their social lives.

Millennials and Gen Z make up the majority of pet owners and over 60 percent are remote workers, entrepreneurs, and retirees with flexible schedules. More than 75 percent of pet owners say that current economic conditions haven’t changed their pet spending and roughly the same percentage admit that they’re more likely to splurge on their pets than themselves. It doesn’t hurt the industry’s prospects that the U.S. pet market is relatively recession-proof and should top $160 billion in 2026.

There’s been a throwback to those imagined days in the 70s rom-coms where all it took to meet the man or woman of your dreams was a leash, a cute cocker spaniel, and a walk in the park. Outside in the fresh air—even during the worst of the pandemic—not even the omnipresent masks were a problem. Of course, the whole program was largely dependent on the weather, which back in those days was unpredictable at best. Rain, snow and bitter cold made the daily rituals tough on the pups and even harder for their parents. These days it’s even crazier.

The truth is that in most cities, you can have three seasons of weather in a single day with the occasional hailstorm, hurricane or tornado tossed in as well. This is one of the main reasons the team from Zoomies is opening a huge new indoor dog park in Chicago that takes the weather out of the equation. Chicago has about 600,000 dog-owning households with about 250,000 homes within 20 minutes of the new location. This is its initial location with rollouts planned for other major urban areas shortly. After the business model is proven out, the plan is to expand through franchising. The Zoomies environment has been designed with a powerful HVAC system that refreshes and replaces all the air in the entire 24,000 square foot facility every eight minutes as well as an impervious rubberized floor that’s easy to maintain and comfortable for the four-footed fans and their folks.

A Zoomies dog park in Chicago.

The first of its size in the U.S., it’s a clean, cool and inviting place to let your pup play with others in a safe, secure and leash-free park. There’s a separate area for smaller dogs, some enclosed outdoor runs for when the weather’s great, private runs, and a full line of daycare, boarding and grooming services. And for members, there’s an included free monthly nail trim which eliminates one of the most uncomfortable and squeamish tasks of any conscientious owner. I’d love to have a quarter for every unused nail clipper sitting and gathering dust in people’s homes after their first abortive attempt to clip their own dog’s nails. It’s not a job fit for man nor beast.

But the real bonanza at Zoomies is that it addresses the community and social component which is missing in most outdoor park visits these days where the dogs need to be leashed, the nannies and yuppie parents give you dirty looks for invading their kids’ space, and half the crowd are surly and snarky dogwalkers who could care less about anything other than getting the dump done and moving on to their next gig. These aren’t reliable regulars or partner prospects; they’re more like unhappy folks working off their community service sentences. Not the crowd you’re ever looking to hang with.

Zoomies are designed to be upscale social clubs as well as dog parks, and look to me like a fun place to spend some time with your pets and friends. There’s a full-service bar, comfortable seating, and a coffee lounge so you can get just about whatever you need to eat or drink—morning, noon or night. The business plan expects that regular monthly and annual memberships will contribute about 25 percent of the recurring revenue with other principal revenue streams including day passes and daycare, grooming and boarding, community events and private parties, and retail sales and sponsorships.

Pets represent an interesting emotional intersection—responsibility without romance—although at Zoomies there’s a strong likelihood that you might just have both. And remember that a dog is the only thing on earth that loves you more than it loves itself.