HINDSIGHT - WRITE SOMETHING WORTH READING ABOUT OR DO SOMETHING WORTH WRITING ABOUT
Friday, September 11, 2026
Tuesday, September 08, 2026
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.
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Thursday, September 03, 2026
Coward in Chief
Coward in Chief
The Catering Cart President
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.
Tuesday, September 01, 2026
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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 @TULLMANAug 31, 2026As 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).
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