Howard Tullman Joins Lisa Dent on WGN Radio to Discuss A.I. and Chicago Politics

 Listen to the show here

Listen to the show here

New INC. Magazine column from Howard Tullman 4 Reasons You Need to Right-Size Your AI

 

4 Reasons You Need to Right-Size Your AI

Sometimes it’s smart to be careful—and slow—when you’re dealing with new technologies.

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

Aug 26, 2025

This is a very complex and challenging time for startups and small businesses in terms of how they should be addressing all of the issues and concerns around artificial intelligence and, more specifically, how they can incorporate the new AI tools and technologies into their own businesses. I realize that every startup in the world already professes to have built AI into their current offerings as well as into their future plans but, at best, many of these claims are nothing more than adaptations of machine learning or pattern recognition with a new shiny coat of paint and some text prediction capability. Sometimes it’s smart to be careful and slow when you’re dealing with new technologies. The last thing you want to do is be the latest victim of the fake-it-‘til-you-make-it disease.

It’s not remotely clear that a surface-level solution built on top of a generic large language model system will be of much value or benefit to many midsize businesses with very specific needs and nuanced market dynamics. One size almost never fits all these days. The implementation and operating costs alone of many of these systems would likely exceed any concrete internal improvements that addressed the user’s real needs. On the other hand, a smaller, more targeted, and clearly focused system whose objectives and functions the company’s management understands could be a valuable aid and time-saver if properly deployed.  

A side note that should be obvious but is often overlooked in top-down implementations of new tech is that you must secure buy-in from your key management and other pivotal team members and address in advance their concerns and the typical misunderstandings they may have about the plans, the short- and long-term job consequences, and other implications of the new systems and their roles in the process. 

We’re all rushing to employ these things before we fully understand them and, worse yet, it’s easy to come to depend on these seductive tools even when we know in our hearts that we’re not fully in control of them. You don’t need to cross the chasm in a single bound. Hallucinations and biases are only two of the most obvious risks and concerns when you start looking under the hood of some of these programs and discover that even their makers have only a passing idea of how they really work. 

The big guys in the corporate world can now rush to join the line of lemmings willing to pay OpenAI a consulting fee starting at $10 million to send a team of its eager engineers into their shops to build them custom solutions based on its GPT-4o technology. You would think that—given the havoc that the DOGE monkeys and minions brought about across our entire government—these corporate honchos would take a breath or two and ask themselves whether turning over the keys to their futures to Sammie’s smarties is the wisest course or whether it’s roughly akin to giving expensive whiskey and your car keys to the neighbor’s teenage son and wishing him well on his journey. 

If there’s a single statement that says it all for me right now, it’s the various versions of the observation that no one’s going to lose their business to AI, but most will lose their businesses to competitors who are more effectively using AI to streamline and accelerate their operations, to reduce their headcount without sacrificing customer connections and satisfaction, and to give them a far broader and more accurate overview of their marketplace, their competition, and timely intelligence and data to react to emerging positive and negative trends. 

The best and quickest of the players will rapidly realize that the hours and days they previously spent pouring over voluminous market data, analyzing their often incomplete and delayed compilations, and attempting to extract actionable information from the mess will now be replaced and made available in real-time detailed summaries crafted by young and clever prompt engineers.

The truth is that—with regard to the introduction of any new and disruptive technology—it will take every business a significant amount of time to learn how best to deploy it and how to deal with the displacements, interruptions, and new responsibilities and job descriptions that will accompany it and inevitably cause problems.  

Walking before you run—especially if you’re trying to do this development and implementation basically on your own—is the only rational and cost-effective course. It’s critical to keep in mind that you can always circle back and build better and more robust versions of what you’re initially experimenting with. It’s not likely to be an overnight project or an overnight success, but each iterative step will teach you a great deal, further empower you, and also help you to better understand the capabilities of the tools you are using—even as those abilities continue to grow and expand every day.  

What’s most important is for you to take the time to gather your team and review your operations and outline the areas where some intelligent automation could speed and simplify your own processes and actually produce a better result. In the first instance, none of this needs to be rocket science. Guesty is a legitimately AI-assisted property management system that was designed specifically for short-term rentals handled by Airbnb owners and operators.  

While this sounds about as mom-and-pop as can be, these folks face many of the same issues you do in your businesses—albeit at perhaps a smaller scale. The point is that, if this kind of simple use-case can show dramatic improvements in their metrics and their bottom lines, then shame on you if you haven’t figured out how to replicate these tools and techniques in your own shop.  

Here are four simple examples that a satisfied Airbnb operator told me has increased his yield and profit, dramatically decreased the time he was spending each week on his side business, improved his ratings and rankings with Airbnb, and led to repeat business and referrals from satisfied customers. And to be clear, I think he spends about $30 a month for the app. Eat your heart out.  

1. Hundreds of stored FAQ responses are delivered automatically in context-sensitive and narrative serial fashion 

You would be surprised and possibly shocked to learn how many times a day your team members waste their time repeatedly responding to and answering the same questions over and over again. Often, they do it slowly or inaccurately and eventually they do it impatiently—human nature being what it is—and none of this is good for your business. Automated responses can satisfy a significant number of callers who have simple, redundant inquiries and, more importantly, can deflect the wrong callers by simply and quickly making it clear to them that they are looking in the wrong place. 

Pricing is dynamic 24/7 and throughout each week based on a variety of factors and competitive offerings in the market as well as available capacity 

While in theory you could spend your entire day checking out competitive offerings and prices and adjusting your offers accordingly (and clearly Amazon does its pricing in this fashion every minute) and you could also constantly check your bookings through the week and determine whether price reductions might absorb available and empty units, rooms, or beds (just as American Airlines does all day long), the fact is that neither you nor anyone on your team has the time or interest to do anything like this, but the Guesty system does it automatically for you according to your guidelines and parameters instantly every day.  

Publish and sync your listings in real time across more than 50 major listing services including all the major sites  

You may use programmatic tools (with very little actual accountability) to get your messages out to the masses, but, in truth, you have little idea of who is seeing them and absolutely no real time ability to change or update the content or distribution plan. Intelligent systems using open APIs across multiple platforms give you a one-stop solution to precisely target and deliver your messages to qualified, interested viewers in the proper context with the ability to vary and alter any portion of the listings that you wish at any time.  

Responses to every inquiry are immediately replied to even if the reply is merely a placeholder and conversation starter 

Not surprisingly, response time is a measurable metric that firms like Airbnb use to evaluate the owners and operators on their site who use their services. Automated intelligent systems can respond instantly to every inquiry even if the response isn’t a substantive answer, but only a request for further info, details, or specificity to continue the conversation. In addition to managing the Airbnb metric, this immediate reply improves customer satisfaction and engagement without consuming any incremental resources until the lead is further qualified.  

Bottom line: While these examples may not directly apply to your company’s needs and current operations, each of them is an invitation and a suggestion to explore similar kinds of concerns and friction within your own organization and to see how AI and intelligent automation can help to address and improve things.  

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

    SUCCEEDING ON SUBSTACK IS TOUGHER THAN IT LOOKS

            Many years ago (and more recently again in the midst and aftermath of the pandemic) I warned the thousands of smart, middle-aged, corporate executives who had been fired and had decided to embark upon an entrepreneurial adventure (which would be seeded by their severance pay and/or their savings and retirement funds) that it was much, much harder to launch and sustain any startup venture than they imagined and that the vast majority of them were utterly unsuited for the task. (See https://www.inc.com/howard-tullman/should-you-start-a-businss-now.html.)

            Not only were so many of these folks temperamentally unfit for the constant ups and downs of the process and completely unaware of the many operational and cultural differences in the DIY startup world, but their past experience would also not only weigh them down and be wholly discounted, but it would also make them even more unlikely to succeed. (See https://www.inc.com/howard-tullman/so-your-kid-wants-to-be-an-entrepreneur.html.) Many of these people couldn’t even run their own bath. Not everyone is cut out to be a diva, a prophet, a speed demon, or a huckster.

            Unfortunately, between the massive federal layoffs initiated by the Orange Monster, the cutbacks and staff reductions driven by threats to reduce or eliminate grant and public media funding, and the accelerating demise in general of so many parts of the media business, as Yogi Berra used to say: “it’s déjà vu all over again”.  

            Worse yet, no one seems to recall the debacles of the dot com years, the implosions of the real estate and financial markets, or the fact that these days the “gig” economy and the world of wunderkind “influencers” look more and more like a “share the scraps” cesspool – lots of noise, no signal, and no money – inhabited by a miniscule number of winners and millions of losers.

            So, with specific reference to opinion writers, talking heads and news readers, and former network journalists, it’s been very hard for me to watch the daily departures of mature, experienced, and well-respected media mavens and mentors who are all intent on jumping with both feet into the new highly uncertain world of blogs, newsletters, podcasts, and videos. They’ll all be Substackers soon - whatever that may eventually mean and whether or not they end up liking it. I hope they learn to like it because there’s no going back for them even if there’s still a glimmer of the great news businesses that used to be.

            And, as hard as their lives had arguably become in an environment where the truth took a consistent and humiliating backseat to corporate and financial considerations as well as outright fear of Trump’s threats and lawsuits, they’re about to go from repeatedly pushing a stone painfully up a hill like Sisyphus to racing rapidly down the other side while hanging on for dear life with both hands. And, just as you learn in racing, in the insane hurry up economy, nobody waits for you. 

            They’ll learn quite quickly that other people don’t always dream your dream and that their allegedly “built-in audiences” are frugal, fickle and lazy to boot. They’ll basically love you ‘til they don’t and the Patreon model (https://www.patreon.com/login ) that they’ll pay because they love you or want to support your crusade is a financial fantasy. They’re most likely not to follow you anywhere, even for free, because free isn’t cheap enough. Brand extensions aren’t automatic or givens: Cheetos Lipstick, Harley-Davidson Cologne and Colgate Beef Lasagna were just a few attempts that bit the bullet in no time at all. 

            As someone who’s seen and written about these kinds of radical transitions for more than 50 years, I feel an obligation as well as the need to revisit my earlier cautions and to offer a few important observations that are likely to have been overlooked in the frenzy to move forward.

You Can’t “Ape” Your Way to Success.

            In this noisy and cluttered new media world where everyone is competing for a small slice of a finite and shrinking pool of attention, the primary key to success is differentiation at a time and in a context where thousands of others are trying to do the same thing. You need to start from the premise that no one’s interested in the old models or the tired formats of the past. And honestly, older white-bread white guys aren’t in such great demand either.

            The “news”, such as it is these days, is already everywhere, stale by the time you see it, and free. Regurgitating the same old stories – even in an ultra-timely fashion – simply won’t get the job done and no one wants to pay for it. You’ve got to have a new take, have a hook to set yourself apart, figure out how to attract a viable portion of the world’s attention at least for a moment, and then deliver consistent and valuable content every day in order to hold your audience. It’s a “what have I heard from you lately” world with a million alternatives just a click away.

            While John Chancellor once said that the function of good journalism is to take information and add value to it, the truth is that the media business today is far more about entertainment than education. It’s about looking, listening and laughing rather than leisurely learning. About fear and anger rather than fashion or foresight. Enragement, not engagement. The key seems to be pithy, bite-sized, observations and outsized opinions rather than painstaking analysis, careful commentary, or attempts to prove anything. People aren’t looking for proof – they already know what they believe – they’re looking for confirmation and reassurance. The truth has as much to do with this process as mustard does with ice cream.

You Don’t Get Paid Until You Pay Your Dues.

            Ignoring the wisdom and lessons of decades urging folks to try before they buy, whoever is advising these newcomers to put out a few interesting paragraphs and then slam up a subscription paywall to interrupt the initial experience is a moron. This strategy is a slight cut above pure clickbait, but to any serious person and interested reader, it’s just an offensive turnoff and utterly counterproductive because instead of introducing the prospect to compelling samples of the author’s work, it shuts the door without a single example and generally results in a swift click away. Email subscriptions, after some introductory exposure, make sense especially because you build a direct connection to your reader, but paywalls are a complete waste.

            You’ve got to be willing to invest your time and effort for a while at least without expecting any financial return regardless of your experience, talent, brand or prior reputation. The best players under-promise and over-deliver, which makes for a strong connection, a lasting relationship, and even a willingness to pay. All smart business is ultimately based on patiently building relationships. If you’re in it just to make a quick buck, you might just as well be selling shoes. You don’t want to be splitting up the loot before you rob the train.

            As much as it can appear to be a frantic race and a contest, in the long run, the people who survive will have built a small, but passionate community of followers who are willing to support their work financially because they trust the authors and because they find real value in the work. The authors, in turn, will be authentically connected to their followers and able, at the same time, to create content that is meaningful and satisfying both to themselves and to their fans. It’s not about beating the others; it’s about building a valuable business for yourself that you can be proud of. You get the chicken by hatching the egg, not smashing it.

You Might Not Have the Stomach to Do What It Takes.

            One of the reasons I retired from practicing law was that, as corporate litigation became increasingly expensive and lengthy, the clients eventually lost their appetite for the battle and their willingness to pay the required costs for doing the necessary work correctly and completely. Doing a halfway job wasn’t my style just as discouraged and disappointed doctors every day are told by indifferent clerks and flunkies working for insurance companies that they don’t care to pay for certain medical tests which the professionals feel are essential to properly diagnose and treat their patients. Even apart from the desire to take pride in the work you do, no one gets into these professions to do a crappy job.

            In the same fashion, experienced journalism professionals who’ve spent their lives and done their work according to long-established standards of honesty, fairness and objectivity - supported by talented staff and plenty of resources - may simply not have the stomach or willingness to take things of importance, depth and substance on the fly without the time to properly investigate or prepare and then proceed to simplify and hollow them out so that they can be swallowed by their audience without chewing or thinking.  Patience, prudence, modesty and humility have no real place in the attention economy. It’s a war zone with no bottom.

You Might Not Have the Stamina to Stick It Out.

            It’s hard, if not impossible, for a man or woman in their 40s or 50s with a full life, a family, a home and various other financial commitments, to compete effectively and flat-out every day on a 24/7 basis with kids in their teens and young adults who have absolutely nothing else in their lives, no reputation or integrity to preserve and protect, no moral inhibitions, incomparable levels of shamelessness, and few ethical constraints. The new adult entrants talk about freedom and independence without recalling Janis Joplin’s note that: “Freedom is just another word for nothin’ left to lose”. They’re putting their whole lives and careers on the line to compete with kids having their latest lark and living on their parents’ dime.

            Outsiders and grown-ups rarely understand the daily grind of feeding the content beast along with the physical pressures, mental stress and difficulty of getting on the non-stop creation treadmill. You’ve got to fill the void with something every day. When you add in the responsibilities of developing, marketing, managing and operating the other aspects of building a new business in an impossibly competitive industry with thousands of players all chasing a shrinking and cluttered pool of interested readers, listeners and viewers, it’s easy to see why it’s not a business for the faint-hearted or for those who are already fatigued and burnt out.

You Might Have Already Missed the Boat.

            Finally, and unfortunately, you can’t turn back the hands of time and you might just be too late to the party to make a go of it. These spaces are already crowded, and they already demonstrate the same “winner take all” tendencies of the tech world. A few big names will emerge, a few platforms will dominate and deliver, and the costs of entry and participation - which once formed significant moats - have already become trivial and are about to be totally obliterated by A.I.

You’ll know in relatively short order the answers to some of the critical questions above. If it’s not working or working for you, don’t kid yourself and continue. It’s never too soon to turn back if you’re on the wrong road.

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

 Listen to the show here

Listen to the show here

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

Why Now Is the Time to A.I. Audit Your Business

A.I. isn’t an optional add-on. It’s foundational and roughly equivalent to electricity or the internet.

 

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

Jun 17, 2025

 

In most of my conversations over the last year with new business owners and seasoned operators, all of whom are all concerned about ChatGPT’s impact on the economy, I’ve found an interesting contradiction in the way entrepreneurs are approaching the use and incorporation of A.I. I see a whole lot of wait and see.  Is it a genius or a clown?

While the novelty is starting to wear off, and the hiccups and hallucinations are certainly reasons for caution, the critical need to investigate, engage with and integrate these new technologies has yet to be fully appreciated and folded into the planning and operations of millions of businesses that really can’t afford to wait. They’re taking their time when the time to move is now and the timing couldn’t be more critical.

It’s not that hard to see why they’re conflicted. They’ve lived their entire business lives trying to be innovators, first movers and early adopters of new technologies in order to stay ahead of the competition. The “ready, fire, aim” attitude has mostly served them well over the years. But the truth is that smart entrepreneurs are far more careful and conservative than we’ve been led to believe. In fact, many are control freaks.

So, when they’re confronted with a pitch that basically says they should turn over some of their business processes to the “machine” because it will be good for their bottom line, they’re more than a little wary and reluctant to jump right in.  00:0001:49

Add to their basic mindset the fact that they understand almost nothing about how these black boxes really work, that they rarely have anyone presently onboard who can help them learn or who is up-to-speed on AI themselves, and that things seem to be moving ahead and changing at a ridiculously rapid pace. This makes for a perfect formula for angst and analysis paralysis. But, as is always the case, worrying never gets you anywhere and standing still is never the right solution.  A bad decision is often better than no decision at all. 

The good news is that there are simple and cost-effective steps forward –“toes in the water” if you will – that every company can take to get the ball rolling, and none are “bet the ranch” actions or expensive decisions. They’re simply smart ways to get smarter sooner.  

Every business today needs to conduct an AI audit if they don’t want to be left behind. AI isn’t an optional add-on at this point; it’s foundational and roughly equivalent to electricity or the internet. In the call center industry, for example, it’s now estimated that AI agents will handle 70 percent of all contacts by 2028. 

The first order of business doesn’t require technologists or AI experts. It’s simply a comprehensive review by your senior leaders of various areas of the business where AI may be able to help. Not, to be sure, by working immediate miracles (in spite of all the hype about eliminating hundreds of jobs overnight), but by helping you identify improvements, import better practices, and eliminate obstacles in your current operations.  

In my experience, this audit and review exercise also encourages your people to do some wishful thinking, to look forward to what could be, and to even think outside of their day-to-day, nose-to-the-grindstone activities and responsibilities. It’s a literal license to iterate and constantly improve.  

Broadly speaking, I’d break the critical categories down into four major buckets: automation of various internal processes, automation of various external processes, cleaning up and streamlining basic operations, and all your employee issues from augmentation, robotics, and realignment to concerns around recruitment and retention.

Once you’ve built a hit list and a wish list, you can bring in some professional help, a prompt engineer or two, and other AI resources to start building some solutions. Here are four examples.

Internal processes 

The long-term dream of a paperless digital world remains a remote and ambitious fantasy for millions of companies still drowning in reams of paper reports, receipts, requisitions, and records of all kinds. From the accounting department to the shipping center and personnel department, AI tools will create massive improvements in the traditional systems and antiquated procedures used in virtually every business, government agency and regulatory authority. Automation, digital records and AI-enabled identification processes will improve diagnostics in medical facilities, security in all of our transportation hubs and public areas, and in the entire finance world. 

External processes 

As the world becomes increasingly comfortable with ATMs, self-service checkout counters, and other forms of automation, AI systems can speed up, simplify, enhance and scale all of your front-of-house interactions with customers, clients and consumers including sales, service, and support. Millions of bank customers already acknowledge that they would rather not deal with a teller if efficient alternatives were available. AI tools can also streamline, simplify and optimize websites which, in many instances, companies haven’t reviewed or updated in years to improve customer experience and speed up the process.   

Basic operations 

Real-time review, ongoing support and enhancement, and timely intervention to avoid problems, breakdowns and other system interruptions are already being implemented in manufacturing firms around the world. The ability to project needs, demands and resource requirements will build even further upon the economic success of many just-in-time supply and warehousing chains and save huge amounts of time and money. Having AI systems review months or years of prior actions and activities and generate detailed analytics on the fly will provide insights, new directions, and even concrete suggestions for process improvements and better use of personnel and other materials and resources.  

People  

AI and related intelligent agentic devices and robotics can augment and supplement the work done by your employees to improve accuracy, capacity and safety as well as avoiding burnout, repetitive behavior injuries, and human errors. Systems are already being designed to identify, evaluate and categorize job applicants on a variety of criteria, to assist in scaling and speeding their documentation, onboarding and training, and to outline and create multi-year individualized career paths for each team member which serve as great recruiting tools and help to manage education, expectations and attitudes as well as improving retention. MIT and Nvidia Research have already developed a new algorithm that enables a robot to “think ahead” in a planning process and evaluate thousands of alternative paths in seconds. 

The bottom line is, you don’t know what you don’t know about your own business until you ask. Now’s the time to start asking. There’s no better, more cost-effective system than an AI system built for and based upon your own data as well as employing comparable data and other information drawn from the industry, your competitors’ reports and activities, and all manner of other external information and data sources. An AI audit is step number one.  

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

The Age Wave is a Better Bet for Entrepreneurs Than A.I. 

Money may be pouring into A.I., but if you’re looking to start a business, there’s a huge market in more mundane areas, such as serving the rapidly growing number of seniors.

 

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

MAY 6, 2025

It seems that every young entrepreneur these days is racing to imagine, build and deploy new AI-infused products and services to meet expected and often wished-for demands for solutions to unknown problems and cures for unknown diseases. They speed ahead whether or not it makes even the slightest sense to incorporate AI as a critical component of what they’re hoping to build. 

It’s also unclear that they even understand exactly what they’re pitching when pressed to explain the technology beyond the superficial buzzwords that ChatGPT will happily supply for them. But nobody wants to miss the parade. And equally anxious investors are chasing similar dreams and throwing money at these stories with reckless abandon, as long as the pitches contain those magic words. 

This frantic approach is costly, risky, uncertain, and the playing field is already grossly overpopulated with well-funded participants of all sizes. Yet because the underlying platforms that drive all these efforts are already largely controlled by a few tech giants, the ultimate economics of even the most successful efforts will be questionable.  

While all the challenges and obstacles are clear, no one honestly knows what the demand for any of these offerings will be, and how any startup will be able to differentiate itself, reach critical scale, and avoid being crushed or obviated by the big guys. This is going to be a heavy lift and a long haul for rewards that are speculative at best. 

The opportunities in our aging population

Forget the shiny objects: there are huge unmet opportunities to create simple, inexpensive and effective offerings for the immediate problems of millions of older consumers in our rapidly aging population. Businesses that represent attractive investments at considerably lower risk. Where entry and minimum viable product (MVP) costs are low, milestones and success metrics are easy to define and measure, and it should be clear in a relatively short time whether the dogs are interested in eating the dog food.

In 2025, more than 11,000 Americans will turn 65 every single day, or about four million folks a year, driven by the Baby Boomer generation, (born between 1946-1964). New and important products and services for boomers don’t require the capital, compute, natural resources, or technical expertise associated with chatbots, LLMs or next-gen AI models. These people have problems, plenty of cash, are still inexpensively reachable through traditional media channels and membership organizations, and they acknowledge both their needs and the need for solutions. They don’t require convincing as much as they simply need to be informed, educated and encouraged to act in their own best interests.

Apart from bragging rights, shiny object syndrome, and peer pressure, you have to wonder why more new business builders aren’t focused on meeting these massive, albeit mundane, needs.  They could make a great living while they’re at it. I realize that good, solid businesses might sound boring to certain people looking for the next moon shot, but it’s hard to miss some of these substantial market gaps when they’re staring you right in the face.

You can call this strategy “catching the next age wave” and it reminds me of a great Warren Buffett quote. He said: “I don’t look to jump over seven-foot bars; I look around for one-foot bars that I can step over.”

Three considerations about the market

Broadly speaking, especially if you’re an involuntarily unemployed grown-up looking for a new challenge, I’d suggest investigating three critical areas of non-medical, elder assistance where there are immediate openings to set up shop without even leaving your home or neighborhood. A little planning, some modest preparation, and a little research will save you a lot of time, money and shoe leather. Your friends, family and neighbors will readily support leads, suggestions and recommendations as well as introductions to more prospects and target customers and consumers than you can imagine.

Why? Mainly because there are no communities in this entire country without thousands of individuals in need of these kinds of services and support. Three initial observations to provide some context.

First, many of these services may exist for high-end, well-banked and connected individuals, but they are virtually non-existent for middle-class consumers of any advanced age.

Second, to the extent that any of the vendors purport to offer any in-person services along these lines for technology products or mobile devices as opposed to tele-support, the delivery personnel are universally abrupt, impatient and unempathetic kids who no one wants to deal with, or welcome into their homes and private matters, and who are typically somewhere on the behavioral spectrum. There’s a reason Best Buy’s guys are called the Geek Squad.

Finally, and more generally, the ideal entrepreneurs and operators of new service providers in these areas will not be young people. They are mature individuals, disciplined and hardworking, coming from prior careers in the corporate world, insurance, banking, and even government, and who are organized, well-groomed, seasoned and presentable.

Three services the market needs now

The key areas where I see very few players, but lots of potential, are assisted access, assisted giving, and assisted relocation.

Assisted Access Businesses are those primarily addressing the needs of seniors who have been left behind by the rapid advances in technology. Services can include simplified tech support and user education; hands-on, hand holding and in-person training; application installations and regular updates and upgrades of equipment.  Seniors need all manner of confidentiality protection, device security and storage, as well as recording, retention and retrieval of critical information regarding their finances, passwords, bank and service accounts, and other verification procedures and scam warnings.

Assisted Giving Businesses address a different area in which seniors and homeowners in particular are uninformed, unsupported and largely incapable of acting efficiently and intelligently. While there are zillions of criminal and fraudulent schemes targeting seniors that purport to be serving charitable and philanthropic causes, here again my focus is on some much more mundane, but no less important, services. Boomers have needs and concerns regarding the timely, pre-death disposition of personal property, artwork, family heirlooms, and jewelry, for example, which may be generically addressed in formal wills and estate documents, but which typically are much better and efficiently addressed while the owners are still living.

Unfortunately, here again, with the exception of a tiny percentage of precious objects and works by well-known artists (which are still difficult to have appraised or sold, even at auction), there are simply no organizations, services or other providers to help seniors plan, inventory and then rationally and prudently dispose of these objects. Of course, some portion of the property and other possessions may be desired by family or heirs, but in most cases – even if nearby family members have some modest interest in assisting – the burden of all the effort ultimately falls on the seniors.   

Assisted Relocation Businesses help seniors quickly and efficiently sell their homes at realistic prices and also simultaneously provide guidance and support for these individuals to move into smaller owned or rented properties or into assisted living facilities. Moving Station is one of the smart early players in this space. This is a very complex area and, in most cases, requires close coordination to ensure smooth transitions. One other difficult and emotional part of these transactions is how painful and agonizing they can be for all of the parties concerned and especially other younger family members. Having objective, independent and supportive intermediaries is a crucial component for closing these kinds of deals in a timely fashion.

Ultimately, what the most successful operators of these new businesses will be selling are themselves as well as comfort, reassurance, and attention to detail. No one’s gonna care how much you know until they know how much you care….about them, their affairs and their future.

HOWARD TULLMAN JOINS LISA DENT ON WGN RADIO TO DISCUSS RAHM'S FUTURE PLANS

LISTEN TO THE SHOW HERE 

LISTEN TO THE SHOW HERE

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

Time to Ask Some Tough Questions About AI 

Has there ever been as much hype about a product that has yet to prove its value for most businesses? That doesn’t mean you shouldn’t take a hard look at what AI might do for you. 

 

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

MAR 4, 2025

You just might need AI to help you list all of the issues and concerns that surround AI today.  

One of the most persistent worries in the business community is whether any of the various large language models (LLMs) are really ready for prime time and for widespread adoption by companies looking to incorporate these new technologies into their day-to-day operations.

Even if you are willing to put aside all of the commentary about hallucinations and false references, and the circularity problems raised by these systems blindly ingesting the garbage already being generated by other AI systems and thereby diluting the value and accuracy of their own outputs, you still reach the fundamental question of which version of the “truth” your own people can rely upon. Or even choosing among competing offerings that are now creating and delivering inconsistent and conflicting results.

It’s a very tough choice for the IT department to decide which LLM, if any, to endorse and adopt at this point. While a segregated sandbox to be experimented with wouldn’t cost a bundle (apart from the overhead and personnel time), once any firm tried to incorporate these systems into their own workflow at the enterprise level and install it in hundreds of seats, you’d be talking about a few hundred thousand dollars.

I guess that if you don’t care where you end up, and you’ve got money to burn and want to tell your board that you’re doing something, any road will get you there.

A free consumer offering and a novelty accessed by millions of curious users is one thing. People will try anything for nothing, especially folks with plenty of time on their hands and nothing to lose. But this is not a sustainable solution for serious operators on either side of the equation and – as we have already seen – it’s also not a remotely profitable model for the primary providers, since they lose money on every inquiry.

Why They’re Trying to Get Everyone Hooked on AI

All the big guys are racing to create a viable AI assistant for the little people in the hopes (as has happened in the past) that adoption from the outside in (remember all the ad world creatives using Macs) will eventually dictate which larger solution a given business will adopt. If your people all love Perplexity, you don’t really want to start swimming upstream and pushing some other choice.

The civilian population is already reaching the point of confusion and fatigue because there are at least half a dozen major offerings in the market with more variations and versions coming every day. ChatGPT presently towers above the rest with more than 350 million monthly active users.

But Microsoft, Google, and DeepSeek are already reaching some reasonable levels of scale and it’s never smart to bet against fast followers when they are as deeply entrenched and well-funded as these guys are. Watching Microsoft Teams slowly eat Slack’s lunch is a good indicator of where these things often end up.

Microsoft’s decision to shut down Skype and put the functionality into the Teams package is another good indicator of the old tech rule that winners take all. Remember that Microsoft itself spent $8.5 billion in 2011 to buy Skype to replace its own mediocre video offering.

The AI Race Is Still Wide Open

No one is there yet in the AI race. The main riddle is to make the assistant contextually savvy, and surprisingly Amazon is a player in this race because of Alexa. With more than 600 million Alexa-enabled devices, the world is already comfortable asking Alexa for help. And with new tech, familiarity builds acceptance and comfort rather than contempt. It’s still a “go with what you know” world.

All the major players aspire and claim to be delivering the most accurate and comprehensive responses to carefully crafted prompts. In fact, the demand for prompt architects and prompt engineering  has exploded as it becomes clear that even the best answer is useless if you’re asking the wrong questions.

We’re also seeing a surge in new businesses aiming to deliver industry-specific AI tools like GPT-4o for Law and also startups that offer to help companies build their own small and custom models based on their own proprietary data.  The idea is to avoid the generic overkill and costs of the major LLMs. You don’t have to boil the ocean and burn big bucks every time you need some straightforward answers about your own business and customers.

One other interesting new startup, Avatar Buddy,  builds low-cost, task- and role-specific “buddies” for sales and support people, as well as experts and digital twins for educators, which provide real-time assistance and direction to folks in the field.

But all these conversations tend to return to the core issue, which is: How is a buyer supposed to evaluate and decide between these many alternative tools when even extensive, comparative tests are inconclusive or contradictory? There’s very little credible guidance so far; the players keep updating their solutions and moving the measurement goal posts.

Which means that for the foreseeable future, if you want to hold your nose and jump into the pool, you’re probably best advised to follow Yogi Berra’s classic advice: When you come to the fork in the road, take it.