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

LISTEN TO THE SHOW HERE

 LISTEN TO THE SHOW HERE

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.

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

Learn How to Be a Better Reader 

The major newspapers have failed in their mission. We need a new format that does everything they once did–curate, inform, educate–without the baggage.

 

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

APR 1, 2025

The major newspapers simply aren’t getting the job done any longer. Apart from the fact that the printed paper is outdated before the press run is even finished, they aren’t telling us what we actually need to know in an effective manner. Smaller local papers continue to disappear, and the three leading national papers cower, cave and collaborate with the demands of the Orange Monster and their own corporate masters – joined these past few weeks by several of the largest law firms and major universities.

We are largely left to our own devices to find alternative sources of substantive news, serious thought, and opposition to the onrushing autocracy.

Newspapers today – even with unlimited online space – are opting for fluff, filler, and a lot of nice-to-know nonsense instead of substantive coverage of pressing national affairs. Many local papers are now dropping editorial pages entirely. And, as they shrink in size and shirk their obligations, they look like unfortunate jugglers trying to catch the wrong end of a bunch of plummeting knives – painful, pathetic, and painted red with the blood, sweat and tears of departed staffers.

The most immediate result of layoffs, buyouts, and bizarre dictates by billionaire owners like Patrick Soon-Shiong of the Los Angeles Times and Jeff Bezos of the Washington Post is the continued flight of major talent. Readership is disappearing, too.  Many of the best writers, editors, and reporters have abandoned the major rags to set out on their own to tell their stories and honor their callings through social media, YouTube videos, podcasts and new digital forums. But it’s an enormously difficult task to find an audience and make a living while you’re at it.

The Best Journalists Are Leaving Newspapers Behind 

Online digital channels like Substack, which provide a forum for opinions, reports and longer articles, are the prime beneficiaries of the writers’ exodus, for example, Jennifer Rubin of the Post. I also like Joyce Vance, Heather Cox Richardson, Shelly Palmer, Charlie Sykes, and Frank Bruni. Other new services like Bluesky and Threads — which unfortunately followed the constricted Twitter model best suited to short slander, right-wing hate, and trolling — haven’t really offered much of a viable alternative, despite building substantial audiences.

You can’t really say much of value if your message needs to be truncated into a dozen little squibs. And literally millions of new users signed up for these services without a clue as to what they were likely to find, or which other users and contributors might be on any given channel.

But these new forums, channels and writers face a much bigger obstacle that is likely to financially doom many new authors seeking a viable audience. What you say or how well you’ve said it doesn’t matter if (a) no one can find your work and (b) if, as a result, no one is reading or listening to it. Even if you think you know what you’re looking for, without a specific name in mind, there’s virtually no way to find anything of value among the thousands of returns that a typical Google search might generate. There are no editors, curators or guideposts to manage the constant stream of new material.

How Substack Hurts Its Own Users

Substack makes life even more challenging for its authors to build a sustainable audience by the utterly stupid step of automatically unsubscribing anyone suspected of forwarding a post to a mailing list. In other words, while their own offers litter every column with pitches to subscribe at various fee levels (including free), Substack punishes anyone for aggressively sharing a particular piece with a larger audience of potential subscribers by kicking them off the author’s page. This even includes articles which have been served for free by writers trying to get their message shared as widely as possible.

As if finding new materials and writers wasn’t tough enough, the Substack idiots penalize people for providing free marketing for their authors.

With Trump and his flunkies now threatening to effectively limit access to Social Security and privatize the United States Postal Service, online services may soon be the only effective channels that remain for most of our population. As they envision their brave new, tech-first world, the MAGAts never bother to mention the millions of older, rural and poor people, including their own supporters, who still lack access to online internet services or cellphones.

There are still important and critical nuggets of information regularly buried among the gross amount of garbage we get online. Today we all live in various degrees of fear of missing something critical from a friend, family, bank, litigant, government agency or other correspondent. And we regularly do miss messages directed to us at infrequently visited sites.

How To Be a Better Reader

Given this cluttered context, the scarcity of our time, and the fractionalizing of our attention, you need to selectively invest the energy in finding valuable new information sources, intelligent and informed writers, and news feeds that anticipate important events and prepare you to respond.  That’s in contrast to those that merely regurgitate the same tired factoids we see in dozens of different posts across the web.

You can start by finding out where some of your favorite columnists moved and follow them. But this process is too often frustrating. Medium does a decent job of collecting your interests (very generically) and then provides a long list of suggested writers who might be relevant. But it feels like a complete crapshoot, and you’re required to subscribe and pay a fee to proceed. Plus, much like those of us who presently subscribe to too many streaming services for no good reason, it quickly becomes a fairly expensive proposition to spend $50 a pop to support a dozen of the newspaper columnists you used to follow in one or two places.

Interestingly enough, this process of aggregation, validation and assembly of select writers, educators, scientists and other professionals used to be one of the primary functions of major newspapers. Your favorite paper was basically a one-stop shop, a convenient, well-organized and edited, and relatively painless delivery system especially when compared with the absolute drudgery that discovery on the web today represents. Those were the good old days.

Bottom line: we need a trusted online aggregator, or maybe a linking service more tailored than Apple News, where users can find and designate the content, authors, commentary and topics that interest them and have those delivered in a single, morning submission. Sorta like the newspaper you used to find on your doorstep.