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.
