NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

Successful Serial Entrepreneurs Share 4 Habits That Make Their Next Startup More Likely to Work

These aren’t innate attributes—they’re learned skills and boundaries.

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

Sep 7, 2026

Having invested in several dozen startups over the last decade and read hundreds of business plans, I’ve been pitched by individuals with a broad range of experience and credentials, including some of the most interesting men and women who were previously successful entrepreneurs. These folks were anxiously getting ready to jump back on the merry-go-round and take another shot at the brass ring. Once you get the fever, it can be hard to get over the adrenaline and hurry-up disease and go back to trying to find a day job and live a relatively normal life. Interestingly enough, the one thing that’s almost immediately obvious in these cases is that—regardless of the degree of their prior financial rewards—they have little or no interest in funding their next new ventures with their own funds. It’s the rarest kind of new business builder and true believer who’s interested in putting his or her butt on the line twice.

But, say what you will, trying again is a lot better and healthier choice than retiring or thinking that you’re qualified and temperamentally fit to become a venture capitalist or professor of whatever. Entrepreneurs are congenital optimists who fall in love with every new idea they see and are often miserable investors, while the best VCs are grim and constipated naysayers who reject 95 percent of the deals they are shown. They say “No” all day long with big smiles on their faces and send you off with a hearty pat on the back. 

Many college profs teaching entrepreneurship are either indifferent and burned-out oldsters who have a thick enough skin to be told by their students that they don’t “get it” or don’t know what the new A.I. world is all about. Or they’re folks whose past ventures almost made it across the finish line but never put enough cash in their pockets to free them from needing a paycheck. They eventually figure out that teaching a bunch of kids is easier and less time-consuming than working a 9-to-5 job with a boss who’s paying attention and paying the bills. So, they spend their days swanning about among a host of bureaucrats who are largely paid to not upset the apple cart, offend the student snowflakes and their parents, or fail to placate the omnipresent corporate donors who pay for their buildings and labs.

When you run into successful serial entrepreneurs and have a chance to examine what makes them successful, there are a few characteristics that they all seem to share. These aren’t innate attributes—they’re learned skills and boundaries.

I’m looking at a prime example now, which is a new business launching a juvenile stationary “bike” called Tovie that helps struggling kids manage various nervous system conditions and sensitivities. The entrepreneurs behind Tovie, Arnav Dalmia and Shivani Jain, were two of the founders of Cubii, a pedal-driven, under-desk, elliptical trainer for adults that attracted nearly 1 million users after a record-breaking Kickstarter launch. Full disclosure: My venture firm invested early in Cubii more than 12 years ago, and the company had a very successful and lucrative $100 million exit in 2020 that made us a lot of money.

Tovie is a smart product. It plays entirely to the strengths and experience of the enhanced management team, and they’re managing the launch, development and funding steps in a manner which worked extremely well for them in the past–walking before they run and iterating all along the way. This is exactly what I’ve seen work successfully for a number of successful serial entrepreneurs in a wide variety of markets.

First, the smartest entrepreneurs recognize that, while many of their skills and strengths are readily transferable and applicable in diverse cases and circumstances, this isn’t the case for accumulated knowledge, experience and expertise in any given area or vertical. Even the best entrepreneurs fail regularly when they embark on new adventures outside of their own skill sets and knowledge–building new businesses really isn’t a great place in the new digital and A.I.-infused marketplaces for on-the-job training–there’s just not enough time or tolerance for anything other than forward motion. Pick your spots carefully, stick to your knitting, and go deep with what you know. Or, simply stated, if you want to beat Jannik Sinner, don’t play tennis. 

Second, the ones who are going to get things done and done well admit and acknowledge from the start what they don’t know. They make it their business to find and onboard the talent, expertise and experience required for their offering. In the case of Tovie, the requisite science needs, educational components, and occupational therapy training weren’t as simple as developing and providing a cost-effective exercise solution for a sedentary and deskbound working population. Mechanical skills were certainly within their prior wheelhouse, and the new prototype is thoughtfully and beautifully built with smooth and curved edges, etc. But the science, technology, programming and gamification that drives Tovie—and which is so critical to making the device responsive to and therapeutic for a specific segment and selection of conditions, needs and sensitivities—were almost exclusively the responsibility of teams of children’s health care experts, clinicians, therapists and educators. Parents were also recruited and incorporated into the design and development process. This was especially valuable and insightful because Tovie is actually designed to be a double blessing—calmer and regulated kids make for calmer and happier parents whose anxiety and angst can otherwise be easily communicated to their children.

Third, it’s critical to understand and control the initial scope of your venture. There are zillions of childhood ailments and thousands of kids in need of cures. But you can’t try to be all things to all people and solve the entire world’s problems.

The Tovie team isn’t trying to eat the whole elephant in one bite–they’re entirely focused on the science of regulation–and they’re proving out the premise that measured and controlled movement helps the nervous system self-regulate. Specifically, steering and pedaling are motions and movements that have calming effect. Their pedaling-to-play approach, which turns screen time into active play time, helps kids feel safe, focused, and regulated—even if they don’t exactly understand the methodology involved. And their systems are loaded with parental controls and tools to adjust, limit, and direct their children’s activities at all times. The Cubii venture made clear that there’s always iterative upside and brand and product expansion opportunities once you’ve established a basic product and a solid foundation.

Finally, most people fail to appreciate just how risk-averse true entrepreneurs are and how careful and conservative they are with other people’s money. This is why the Tovie team is so smart to again be pursuing the Kickstarter route, which worked so well for them in the past and which offers a built-in, step-by-step pre-sale measurement tool to get a handle on likely interest and demand before you bet the ranch. New business builders will all tell you that everything costs more and takes longer than you expect, and the only cardinal sin is to run out of money.

Repeaters are also remarkably grateful because they know how lucky they were to have succeeded in the past. This is the non-paralyzing upside of impostor syndrome. They know that they may have worked their butts off and established an entirely new product category, but it was still a major gamble. and there were plenty of bumps and ups and downs on the road to success, as well as folks providing guidance and helping hands along the way. No one does anything material and important all by themselves.

 

 

Coward in Chief

The Catering Cart President

Mary L Trump

Sep 02, 2026

Donald escaping Air Force One via catering truck, leaving press pool and members of his cabinet to fend for themselves after Iranian threat. USA Today photo illustration.

The Air Force One debacle happened a couple of weeks ago, but it is worth continuing to discuss because it has broader implications. First of all, it has all the makings of a bad joke. It is hysterical in the way that it demonstrates what a physical coward Donald is, how inept the people around him are, and it should disabuse anybody of the notion that he is a tough guy, that he is strong or brave. This perfectly exemplifies his complete and utter selfishness and the aforementioned cowardice.

The Secret Service or the intelligence agencies intercepted what they believed were credible threats against Donald and Air Force One. So they removed him without letting anybody else but a very small handful of the select few know. And they snuck him off the plane and put him, and this is just perfection, in a catering cart, which is humiliating. It is something out of Monty Python and the Holy Grail. This is utterly humiliating. It is shameful, and it underscores just how pathetic he is.

On the other hand, though, it is not funny at all because it demonstrates how dangerous and insane the people making the decisions in this regime are. They responded to a credible threat by removing Donald and his handpicked coterie from Air Force One, the potential target. Fine. So let’s talk briefly about who he brought with him.

Thirty five year old Natalie Harp, who I believe is referred to as the human printer, is a woman who spends about 24 hours a day with Donald telling him how great he is, taking down dictation to post his social media rants, and writing him love notes about how he is the center of the universe, her universe. There was Walt Nauta, who used to be his valet and was, of course, his co conspirator in the Mar a Lago stolen documents case, and his former caddy, Dan Scavino. I do not know what Dan Scavino does now. I am sure he made that caddy experience very relevant to working with the president. And, of course, there was the perpetually incompetent Pete Hegseth, Secretary of Defense. The fact that Donald chose those four people to go with him speaks to his priorities and his insecurities because he could have brought anybody.

The question is not really why Donald chose those people, although it is a potentially interesting question that maybe I will get to at some point. And it is not even why he chose to leave the other people behind, although I think it is important to know who those people were. The flight crew, the White House press corps, members of his cabinet, including Secretary of the Treasury Scott Bessent and Secretary of State Marco Rubio, and some of his closest advisers, Stephen Miller and former White House Press Secretary Karoline Leavitt, were left behind.

Again, the question is, why did he leave anybody on the plane at all? By removing him secretly, the people making these decisions made sure that everybody else on that plane remained targets. Because by removing him secretly, they did not remove the threat. They just removed him.

Is there any other way they could have gone about doing this? Sure. I can think of several. They could have said that the plane had mechanical difficulties. They could have said that there was a health emergency. They could have said that something came up with the scheduling and they had to postpone. There are so many ways this could have been done properly, but the fact that they did not just shows you how the people surrounding him are just as incompetent as he is and how deluded they have become into thinking that Donald is literally the only person who matters, that no other human life has intrinsic value.

This is the thing we need to figure out. Why are so many people willing to overlook Donald’s utter lack of humanity and participate in it? They should know by now that it does not matter how loyal they are. I cannot think of two people more loyal to him than Karoline Leavitt and Stephen Miller, and yet he left them on the decoy plane.

It does not matter what you do for him, how you lie and cheat and steal for him. It does not matter how you debase yourselves for him because he does not care about anybody else unless somehow they are of use to him. And then that is another question worth asking. How is it that Walt Nauta, Dan Scavino, Natalie Harp, and Pete Hegseth are of use to Donald Trump, and yet his Secretary of State, Stephen Miller, Karoline Leavitt, and the Secretary of the Treasury are of no use to him whatsoever? Who with the tiniest bit of self respect can continue to work for this man who literally keeps trying to get people in his orbit murdered? If you do not believe me, just remember January 6th.

Explaining the psychology of these people is getting harder to do because this is just the latest in a long line of things that have happened in the last few months that demonstrate just how weak, corrupt, and in decline Donald is. His flailing is becoming more obvious and his self aggrandizement more grandiose because he is desperate to assuage his pathetic little ego. Meanwhile, he is making it clear that, with the exception of that special handful of people I mentioned earlier, he cares nothing about the health, wellbeing, and safety of those closest to him.

I think the best way to understand, to the extent that we can understand, why these people are continually willing to debase themselves to Donald despite the fact that he does not care if they live or die, is that Donald is not good at many things, but he is very good at this. He is good at getting people to make micro concessions to him. Over time, as he and they become more comfortable with the concessions they make to him, the asks get bigger. We have seen this in a broader sense with the electorate as well. Donald has gotten people who continue to support him to accept things that would have been unacceptable earlier.

I am pretty sure we are going to get to the point where he is going to say, “Hey, in order to make America great again, you have to be willing to give up your Social Security.” Or, “Hey, in order to make America great again, we are going to have to put your children into reeducation camps.” And they will all basically say, “Okay, we will willingly do that for you.” This is something that happens slowly over time.

I recently spoke with a Yale professor and former FBI agent about the experiments at Yale University in the early 1960s that psychologist Stanley Milgram conducted. Participants were told by people wearing white lab coats to inflict shocks on other participants who were in other rooms. The point of the experiment was to see the role authority played in people’s willingness to override their own hesitance to inflict pain on other people.

When one of the subjects administering the shock showed hesitance because they could hear, even though they could not see, how the person they were shocking was responding, the person in the lab coat, the authority figure, told them they must continue for the sake of the experiment. More than 60 percent of the time, the subjects were willing to administer the highest level of shock because they were told to by an authority figure. The alleged victim was not actually being shocked, but the subjects did not know that. The Milgram experiment showed people’s relationship to authority and how problematic it could be. We are seeing this play out in real time, both at the societal level and, what we are more interested in right now, the interpersonal level between Donald and the people who continue willingly to choose to be in his orbit.

How much are they willing to put up with? I would not be surprised at this point if they were willing to shock themselves to death if Donald told them to because, in their worldview, he is the ultimate authority and compared to him, they are nothing.

Whenever we see pushback, that is shocking, not in the electric shock sense, but in the, “Oh my God, somebody actually stood up to him,” sense, because it happens so rarely. We saw Jeanine Pirro recently willing to draw the line when Donald was pressing her to indict people falsely for having vandalized the reflecting pool, which, of course, did not happen. Pirro’s willingness to draw the line in the sand here was completely self interested because she did not want to get disbarred for bringing a fraudulent prosecution.

It is also important to remember that Donald was not angry with her because she did something wrong. He was angry with her because she would not break the law for him. When she said, “No, I cannot continue to do this unethical, potentially illegal thing,” she was in trouble. And she did not like being in trouble with Donald. So guess what? She is once again choosing to do his bidding, potentially putting her law license and her future at risk.

That keeps happening in different ways and in varying degrees with all of them. But here is what I would say to anybody still willing to put up with this, who is still willing to debase themselves, who is still willing to risk everything for a man who does not care if they live or die: You people are going to get punished. Donald never will. And your punishments are going to be severe.

THE EMPEROR'S NO CLOTHES

 

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 College Costs More Than Ever. Too Many Graduates Still Arrive at Work Missing the Basics

Employers across the country report that they’re spending far too much time teaching their newest employees basic skills because their colleges didn’t.

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

Aug 31, 2026

As millions of incoming freshmen begin their college experiences, I was struck by how little confidence I—and likely most of their parents—have in the likelihood that their very costly four-year investment in their children’s further education will pay off down the road, in terms of better preparation for their post-college employment prospects and life in general. The only relief for many of these folks (which is a mixed blessing at best) is that their kids have less and less chance of getting into the “name” schools these days. That may not be all that bad a piece of news, because regardless of what’s being taught at those exotic places, the bottom line is that many of the kids aren’t learning the critical things they need.

Employers across the country report that they’re spending far too much time teaching their newest employees how to read, write, spell and otherwise communicate because their colleges didn’t. This is not to automatically say that there’s no clear benefit for millions of students to slogging through four years of the maturation process—it’s clearly supposed to be where you start to develop your people skills and work ethic, along with patience and perseverance. But most of those skills and qualities aren’t learned in the classroom anyway. And, just to be blunt, any thought that AI tools will address and resolve these newbie deficiencies is a foolish idea that has already been shown to be a growing problem rather than any kind of efficient supplement or solution to their astonishing lack of preparation.

In addition, these practical and operational problems are actually dwarfed by the attitudinal deficiencies which accompany these new arrivals after four years of browbeating, lecturing, and indoctrination by professors who think they’re exempt from and far above the daily fray of making a living.

By and large, the insulated and isolated professors who populate too many tenured positions in many of our most expensive and sought after universities regard themselves as too good to bother teaching the basic skill sets and tools that their students will actually need to succeed in the future. Note that I no longer say or believe that these are the “best” schools because—reputation value, branding, and networking connections aside—they simply aren’t getting the job of educating and equipping our next generation of scholars, researchers and leaders done. And the most expensive and elitist of them are among the worst. In addition, for millions of young Americans, two-year vocational schools offer a better, more practical and cost-effective, and quicker path into the real world than the four expensive years at most colleges.

But I’m seeing a glimmer of hope that some schools, some parents and some employers are all starting to take a few steps back and beginning to reemphasize such formerly verboten concepts as reliance on standardized test scores for admittance, resurrecting the traditional idea that math is objective and that there are right and wrong answers that are not subject to debate, and requiring students to stand and present their work to their peers. Smart parents can and need to take an active role in teaching their kids the most basic and important ideas all along the way as to what actually matters.

And, here again, the real bottom line and old-fashioned considerations that we need to teach our kids if the schools are dropping the ball are what I have forever called The Perspiration Principles. Passion (Care More than Others Think is Wise); Preparation (Study More than Others Think is Smart); Perspiration (Work Harder than Others Think is Possible); Perseverance (Stay in the Game When Others Give Up) and Principles (Stick to Your Values and Beliefs When Others Start to Wobble).

HOWARD TULLMAN JOINS LISA DENT ON WGN RADIO TO DISCUSS THE GRAMMYS AND BTS

 

LISTEN TO THE SHOW HERE

                                                              LISTEN TO THE SHOW HERE

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

Brand Extensions Are Supposed to Create Value. The Grammys Show How They Can Destroy It.

BTS recently pulled its newest album from award considerations after the Grammys announced a new music category. It’s an important lesson for entrepreneurs about diluting your brand.

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

AUG 25, 2026

TS perform onstage during the 64th Annual GRAMMY Awards at MGM Grand Garden Arena on April 03, 2022 in Las Vegas, Nevada. Photo: Getty Images

I wrote some time ago about how BTS, one of the biggest bands in the world these days, was developing their own platform that would permit them to “own” a direct and persistent connection to their fans that was free of the many gatekeepers and parasites that have traditionally controlled the music industry. This would permit them to sell swag, special access, live podcasts, and eventually even tickets fee-free to their fans. Another upcoming artist, GiaNina Paolantonia, has similarly built her own platform and app in order to communicate with, connect to, and engage with her fans and followers.

The music industry is like a multi-headed hydra, however, and always has another card to play. The Grammys, an industry organ for decades, just announced a new music category specifically for Asian music in a transparent and expansive attempt to segregate BTS and all the other popular artists and bands from South Korea and elsewhere in Asia. Keeping these performers in their new and narrow vertical prevents these massively popular and emergent artists and rapidly growing music groups from dominating the main award categories which the “industry” prefers to reserve for their own in-house acts. As a reaction, BTS pulled its newest album from award consideration and urged others to do the same. Years ago, the same approach and treatment was used to keep Michael Jackson out of the Grammy Pop category even as he was declared the “King of Pop” and had some of the biggest and best-selling albums in history. And don’t get me started on the years-long shabby treatment accorded to everyone in the Hip hop world.

What really struck me about this latest move was the unbelievable proliferation of award categories that the Grammys have manufactured to continue to slice, dice, minimize and otherwise control the artists and the entire awards process along with all the acclaim, access, financial rewards and other benefits that accompany such recognition. In 1959, there were 28 award categories. Today, albeit more than half a century later, there are 100.

You can decide what real value or meaning any of the “minor” awards actually has, even assuming that the typical consumer actually understood what criteria went into each award and what behavior, achievements or results it recognized and acknowledged. The more tangential awards, of course, the less meaningful each becomes. Spread a mile wide and an inch deep, even the performers can barely bring themselves to sincerely express their gratitude for the Potemkin efforts. The brand and the bragging rights diminish in direct proportion to the number of categories and trophies much like childhood sporting events where virtually everyone’s a winner just for showing up.

Alas, the music biz isn’t alone in meaningless brand extrapolations. We’ve seen dozens of aborted attempts to spread a brand gloss over a grossly mismatched product. Colgate beef lasagna, vegetable-flavored Jell-O, Life Savers soda, Frito Lay lemonade, Cosmopolitan magazine yogurt and my personal favorite, Harley-Davidson perfume. There’s a lot to be said for sticking to your knitting. It may not be new and exciting, but it will likely keep you from falling flat on your face. Brands aren’t concrete and can stretch reasonably far, but not to excess.

There’s no one greater than JD Power at creating an award for every suitor in every automotive category and now expanding into virtually any and every imaginable area of products or services under the sun. You too can win a narrowly drawn JD Power award for the best of something accomplishment in your space—whatever it may be—and even if it’s only for your efforts on Sundays in months having 28 days. You get the idea. Winners galore and all willing to pay wonderful fees to use and promote that recognition in their advertising.

A close second in the race for exponential category growth and the clear winner in shamelessness are the fine folks at Guinness World Records, who invite the entire world to invent records of all types and sizes and then submit them to Guinness for a very costly validation process (Guinness is happy to provide paid consultants to advise applicants) along with judges and witnesses.

Once the months’ long confirmation process is concluded, Guinness provides a framed piece of paper with their brand and seal which recognizes the newly created and established record. They’ll also sell a framed “You Were There” Guinness certificate to every attendee at any Guinness record-setting event. Here again, the very DIY nature of this “record” creation process and the massive number of claimed records makes one wonder about the value of the end product and frankly what the Guinness name or brand even brings to the process. Nonetheless Guinness claims that it receives almost 1000 record proposals and applications per week and over 50,000 submissions a year. 

A pair of Chicago twin brothers who have taken and documented over 82,000 selfies since the Apple iPhone camera was front facing enabled in 2010 are the likely holders of the putative Guinness World Record for “selfies taken by twin brothers” and to date, as their application process proceeds, no one has come forward to dispute or contest this amazing achievement. Taking a page from Michael Jackson, they now call themselves the Selfie Kings. Apparently, in the world of world records, saying makes it so.