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?

HOWARD TULLMAN JOINS LISA DENT ON WGN RADIO TO DISCUSS HIS LATEST INC. MAGAZINE COLUMN

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HOWARD TULLMAN JOINS LISA DENT ON WGN RADIO TO DISCUSS CUSTOMER SATISFACTION ISSUES

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NEW INC. MAGAZINE COLUMN BY HOWARD TULLMAN

 

Your Customers’ Biggest Problems Aren’t Unique. Use This 1 Simple AI Method to Fix Them Fast

The most valuable data-centric businesses today understand that the game has changed again.

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

Jun 22, 2026

 

Time is the scarcest resource in our lives. Data may be the oil of the digital economy, but the timeliness and contextual delivery of that data is what creates real value. One of the things I learned in my first business—providing market-based vehicle valuations to auto insurers—is that it didn’t matter how fresh and accurate our data was or how quickly we responded to inbound inquiries. What mattered is whether the folks asking for the answers were accessible and available when we got back to them with the information. The when and where of the data delivery (context) was just as important as the what (content) in the final analysis.

Driving our people crazy to meet certain performance standards, arbitrary operating metrics, turnaround times, or other contractually mandated service levels was simply stupid if the results didn’t matter to the customers. Not everything needed to be instantly available or made into a crisis or a fire drill if no one was going to appreciate, recognize, or compensate us for the extra effort. Youthful and aggressive enthusiasm eventually led to painful experiences.  

It took a while to get the flow and timing correct in that business, but the core offering–real-time and precise valuation information as opposed to the stale, generalized historical data that was the industry standard–radically changed the way in which claims for lost or stolen vehicles were settled in the auto insurance game. Today, 44 years later, that business, CCC Intelligent Solutions, is still operating as the unquestioned industry leader, works with every major insurer, and is worth billions. The most important lesson we learned is that a one-dimensional emphasis on the speed of delivery or the quantity of the data alone often creates more undue stress rather than building value.

Today, the most valuable data-centric businesses understand that the game has changed again. Now, the key and central concern is capturing vast amounts of data regarding relevant activity—in the moment, at the edge and from both employees and their customers—and then converting and communicating it back to the team members as immediate, actionable instruction. The clearer and more immediate that any strategic inputs can be, the more accurate and valuable the decisions relying upon them will become. The only right time is real time and right now.

And, with considerable assistance from AI tools, we’re seeing the emergence of companies like Pulse that are developing systems to provide real-time data flow, extensive and timely analysis and actionable feedback that can be used effectively to inform and improve employees’ qualitative behaviors rather than simply their quantitative decisions.

These new systems function as intelligent filters, flow managers, and ranking agents so that, by the time the often overwhelming and unmanageable volume of customer feedback data is parsed, parceled, and prioritized, any business can turn scattered, duplicative and unhelpful volumes of customer inputs from multiple sources spread across their entire organization into sorted, identified, consolidated and actionable categories and clear, next-step instructions and directions.

These new systems reinforce what we’ve known for decades but help to organize and deliver better, more timely and comprehensive solutions. Three key areas of addressing customer issues and concerns really stand out, and I believe that they are true of almost every business.

A small number of recurring problems and errors cause the bulk of issues with customers

As many times as you tell your team how, when and what to say, they still forget, quit, freelance, get bored, and get upset or distracted. Automated and interactive scripts, dynamic checklists, sidebar chats and prompts can constantly provide and reinforce the right messages, paths and online responses to issues and objections. Training and practice are helpful, but not as valuable or effective as real-world experiences and immediate feedback.

Problems are rarely unique to individual, unhappy customers. Solutions need to address root causes and then be quickly circulated to the entire team

Solving one-off problems with unhappy customers is necessary, but it’s not sufficient in the long run as a strategy for overall improvements in deficient processes and unsatisfactory behaviors and/or product performance. Even more importantly, once a broader fix is determined and in place and applicable to all customers, it’s critical that the solution (either what’s working or what’s not working) be immediately transmitted to the entire team and incorporated in all of the supportive tools and materials, all future interactions, and all new changes and product enhancements and improvements.

All of us are smarter than any one of us

It’s hard to overstate the value of aggregated, collated, and carefully analyzed data collected from literally millions of conversations, transactions, interactions and dispositions when you’re trying to continually enrich and enhance the customers’ experience and your product or service’s brand, reputation, consistency, and value. Tools like Pulse’s Feedback Intelligence OS put all of this accumulated knowledge and experience directly and immediately and intelligently into the hands of your key decision-makers with actionable instruction and guidance.

The goal today is to make all your people smart as fast as possible and Pulse may be one of the best and most cost-effective systems out there to move your business quickly down the path to improved results and better satisfaction inside and outside of your business.

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

Why ‘Flat Is the New Up’ Is the Best Fundraising Advice for Startups Right Now

In these tight financial times, management’s job is to get whatever dollars are needed to keep the doors open.

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

Jun 16, 2026

 

It’s great to live and work in Chicago where we build businesses, not bubbles. Here, bootstrapping is seen as a virtue to be proud of, raising too much money too soon is regarded as foolish, and people largely keep score not by hyped and highly theoretical valuation numbers but by revenues and results. This approach and attitude are especially critical now when smaller and mid-sized startups that survived COVID and are starting to move forward again, grudgingly determined that they’re going to need some additional funding to get the ball really rolling.

To be clear, in these tight financial times, management’s job is to get whatever dollars are offered and needed to keep the doors open and to help the business keep growing. They’ve typically got two primary choices: going back to their existing investors who are often tired and disappointed, especially with the delays caused by the pandemic or finding new funders interested in the going-forward story. But there’s usually one unfortunate hurdle that can get in the way of attracting and securing new money, and that’s the reluctance of the existing shareholders to recognize: (a) that the prior valuations of the business are ancient history; (b) that the pricing of their last as well as the most recent rounds of funding are also largely irrelevant: and (c) that whatever legal and technical rights they may have to stand in the way of new investments at realistic valuations aren’t really applicable when the future of the company as a going concern is at stake.

That’s why I tell people these days to tell their boards and their long time and more recent investors that “flat is the new up,” which basically means that there’s no shame in taking in additional capital and bolstering your war chest when the opportunity presents itself, regardless of whether you’re also able to secure an immediate step-up in the putative value of your early-stage business, especially when everyone with a brain knows that many businesses just like yours have had to carefully dodge several bullets in the recent past just to stay alive. It’s important to always remember, as Harold Geneen used to say, that the only truly fatal mistake for a startup is to run out of cash. When you do that, they send you to the showers. Everything else is fixable. As I used to say, anything that you can fix with a check isn’t a problem, it’s just another choice. But when you run out of cash, they pretty much run you out of town.

So let’s take stock of the current moment where, regardless of the crazy and relatively inexplicable behavior of the stock market, there’s virtually no IPO market for any business apart from the insane AI offerings. The M&A actors are also largely scared stiff of making any wrong moves and frozen in place as Trump does some bizarre rant or threat to someone every other day and the idea of market consistency and economy stability is just a pipe dream.Code: 102006)

I’ll start with a word of caution: The worst mistakes in business are made in good times, not in bad times. It’s a remarkable fact of life that a small (and shrinking) bank account does a great deal to focus your attention on the things that are mission critical and existential. You stop taking limos to the airport pretty quickly when you’re starting to worry about next week’s lunch money. I’ve been in that position several times and, although it’s good for your waistline, it’s a lousy way to live.

So when funds are being offered even less enthusiastically than you might wish, it’s very tempting to grab the gold. But just don’t lose your way or lose sight of the most important goals for your business. That’s why an emphasis or undue focus on the mainly artificial bogies of interim valuations is woefully misplaced when what only really matters is getting the investment made and closed.

Until you sell your business or take it public, interim valuations are just chatter and cheap talk—not worth the time to talk about and temporary fantasies at best. It’s a lot like wetting your pants in a dark suit: It gives you a nice warm feeling for a moment, and no one else really notices or cares, but you end up with dirty clothes and, as Trump’s minions would attest, stinking up the place.

So, when the opportunity presents itself to boost your bankroll, strike while the iron is hot, but remember these three basic rules of early-stage fundraising:

1.    Getting money is just like eating appetizers. You do it when they are being served. Don’t be reticent or late to the buffet.

2.    Don’t be a hog on valuation. There are a million other deals competing for those same funds; many are just as attractive as yours, and some will be much better priced than yours. Pigs get fat; hogs get slaughtered. Just like on Wall Street, easy money is what everyone else raises: Getting yours will always be hard until it’s done and in the bank.

3.    Take more money than you need, because you will need it, maybe for good reasons (radical growth or expansion) or for bad reasons (disappointing or delayed results) but need it you will.

Ultimately, if you can’t entirely resist being a bit of a hog on valuation, at least be the practical one, just like in the storybooks. Take all the money you can get, say “thank you” (and not another word), and run like the wind. 

HOWARD TULLMAN JOINS LISA DENT ON WGN RADIO TO DISCUSS TAILSAFE

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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.