From the moment he queues up a movie, boots his computer, and hits the treadmill at 4 a.m.—unfathomably refreshed after three hours' sleep—Tullman is a blur. By 8 a.m., having consumed several newspapers, watched half a film (he sees about 120 a year for professional reasons), and cleared his first 100 e-mails, he arrives at Tribeca Flashpoint Academy, the showplace digital-media-arts college he built one summer in Chicago while all the normal people were at the beach. On a typical day, he might brainstorm with Fortune 500 executives in his ADD-décor office; sit in on a commercial being shot by students on a sound stage at Chicago's Merchandise Mart; lead tours for celebrities such as Bill Clinton, Quentin Tarantino, or the documentarian Ken Burns; counsel a graduate on his or her first start-up; hunker down with managers from one of the half a dozen companies he invests in; tinker with the incubator he is building to house 15 of his own product ideas; and teach a class at Northwestern's Kellogg School of Management. Notice how I said and? Not or. Phew.

I rise from my chair to follow Tullman out of his office, and by the time I reach the door, he is already down at the end of a long hallway, greeting Rahm Emanuel, mayor of Chicago and an old chum, here to tour Tribeca Flashpoint Academy and discuss projects of mutual interest. "I have 22 minutes," says Emanuel, who briefly lodged in Tullman's West Loop loft after leaving his White House job to run for Richard Daley's old seat. The two charge around the school for 15 minutes, then settle in to Tullman's office to talk about job training and how youthful they appear in various photos.

At 66, Tullman is a tie-and-socks-optional kind of guy on whom a ponytail would not look amiss. Tribeca Flashpoint Academy is the latest in a long string of companies he has launched, led, or salvaged. And like the autumnal work of a prolific writer, it draws on many of his favorite themes—technology, pop culture, education, professionalism—while refreshing a tired genre.

That genre—or rather, that industry (clarity trumps metaphor, as the storytelling-obsessed Tullman would tell you)—is vocational education. "It's a shame that the United States is the only country in the world where it's considered downscale and horrible to go to any kind of vocational school," says Tullman, pecking at his computer, which is wired to a large screen that barrages visitors to his office with wow-inducing videos and applications created by Flashpoint students and faculty. "Everyplace else, there are apprenticeships, vocational training, all kinds of paths to be successful. We need that here."

Tullman believes training young people to fill tomorrow's jobs is this country's best shot at reducing unemployment and staying globally competitive. Tomorrow's jobs, of course, is code for technology, a subject, Tullman argues, traditional four-year colleges teach poorly because faculty aren't in the field keeping current and students don't work across departments in interdisciplinary teams, as happens in the real world. "Part One was that every other school was teaching in these silos with tenured faculty who weren't learning new technologies," says Tullman, explaining what attracted him to the idea for Flashpoint, which was brought to him in 2007 by Ric Landry, the company's co-founder. "Part Two was you had a group of kids that were only interested in digital and were not going to go to a four-year liberal-arts school and end up with their futures in hock."

Flashpoint offers a two-year associate's degree. Starting Day One, students from all five departments (film and broadcast; recording arts; animation and visual effects; games and interactive media; design and visual communication) collaborate on class assignments and on custom projects for the likes of Microsoft, Disney, and Neiman Marcus. Tullman spends much of his time wrangling those projects, which gild students' portfolios and introduce them to potential employers. "We are totally responsive to what the industry needs," says Tullman, who on the day I visit meets with the CEO of a small business developing a localized entertainment service for inner-city McDonald's franchises, representatives from a Fortune 100 consumer-products company plotting their mobile strategy, and executives from the Chicago arts and entertainment complex Navy Pier, who are soliciting ideas for a $150 million renovation. (See above: Phew.)

Tullman envisions thousands of disaffected, keyboard-addicted kids emerging from their bedrooms and flocking to Flashpoint, where they learn to be both creative technicians and—equally important, he insists—responsible employees. In that sense, the school has the aura of a social enterprise. It is, however, an accredited, for-profit institution that will start making money this year. In 2011, Flashpoint had revenue of $12 million with 600 students; by 2014, Tullman anticipates, enrollment will hit 1,000. There is talk of distance learning as well as campuses in New York City and other domestic and international locations. Tuition is $25,000 a year, with more than half of students receiving financial aid.

Flashpoint's biggest investor is Tribeca Enterprises, co-founded by Robert De Niro, Jane Rosenthal, and Craig Hatkoff in the wake of 9/11 as a way to answer atrocity with art. Owner and operator of the Tribeca Film Festival and other ventures, the organization has invested $16 million, according to Tullman, for a 50 percent stake in Flashpoint. "Flashpoint is a front seat on the world stage of what's the Next Big Thing," says Hatkoff. "If it's exciting and state of the art, they're either using it or they created it."

Flashpoint fits neatly within Tribeca's mission: to encourage innovation in the creation and delivery of narrative. But Hatkoff and his partners were also struck by the intensity and track record of Tullman, who may be the most accomplished entrepreneur you've never heard of. "What Howard has built over the course of his career is just extraordinary," says Hatkoff. "I had never seen a resumé like his before. I had to read it in two sittings."

Tullman's mind moves even faster than he does. "You're having a conversation with him, and suddenly you feel like you've missed a sentence, and your brain races after him," says Barbara Pollack, a frequent business collaborator and friend since childhood. "With Howard, you're always catching up."

Pollack—a member of the Flashpoint start-up team who is now a marketing and design consultant—is part of a devoted coterie that follows Tullman from company to company, responding whenever he blows the new-venture whistle. It is by necessity a hardy bunch; reporting to this guy is no Sunday in a hammock. Tullman works 80 to 100 hours a week, and while he doesn't expect employees to do the same, no one drops in his estimation by being the last person out the door. He is infamous for pounding out e-mails late into the night and for publicizing mistakes. "It's a harsh theory," Tullman concedes. "But if you share that mistake with the whole company, then everybody learns from it. And that person develops an incrementally thicker skin." He also announces his own errors, though those are "rarer than hen's teeth," he says.

Although public admonitions apply chiefly to serious lapses, Tullman is a proud sweater of the small stuff. "I always try to spend a portion of the day micromanaging something," he says. "Just to let people know I'm interested. ERNIE!" he barks out the door to Flashpoint's senior vice president of operations, Ernesto Paras. (For a guy so loaded up with communications technology, Tullman sure shouts a lot.) "I was just saying to Leigh that you and I are going to go into the screening room and bring up the lights on the chairs and the carpeting. Because I think I saw some spills and stuff." Paras informs his boss that someone is already on the way to clean and freshen the fabric. "I think I've communicated my enthusiasm on that subject," says Tullman with satisfaction.

("I catch a lot of things before he does," Paras, another Tullman loyalist, tells me later. "Because he does so many tours around campus, I know he's going to catch everything. We each want to be the one to notify the other of a problem. It's like a game.")

That desire to win on matters large and small was bred in the blood. Tullman is the oldest of six children, raised by an apparel-salesman father and a homemaker mother whose quixotic pursuit of a city council seat (she was a Democrat; the district, in New Providence, New Jersey, overwhelmingly Republican) modeled perseverance and competitiveness for her brood. Sibling rivalry raged intensely, especially between Tullman and his youngest brother, Glen, who is now CEO of Allscripts Healthcare Solutions, a public company with revenue of $1.4 billion, also in Chicago. That's CEO, not founder, Tullman points out. "My brother certainly regards himself an entrepreneur, too," he says. "Only in our darkest and closest conversations do I remind him that he's never started anything."

Tullman developed his nose-to-grindstone ethos in the 1960s at Northwestern Law School, where he assembled defense testimony for the trial of the Chicago Seven and presided over the law review. After graduation, he spent 10 years helping one of his professors and a partner build a law firm. It was while organizing class actions representing tens of thousands of plaintiffs that he succumbed to the imperative and allure of information management.

A lot of Tullman's stories from his entrepreneurial career start out, "A couple of guys came to see me." The first two guys approached him in 1980. They had an embryonic idea to make money on the spread between how much auto insurers were willing to pay for replacement cars—based on often-inflated book value—and how much car dealers charged. Tullman swiftly changed up that model: He wanted to do a database service that would help insurers assess the actual value of cars as determined by real-time sales in the market. He agreed to launch the business, but only if his co-founders raised enough money to make it worth his while. Thus was another Tullman tenet born: The entrepreneur's stake in a start-up should be his time, and only his time. "This idea that you have to go into hock and mortgage your home and starve is bullshit," says Tullman. "I tell entrepreneurs this all the time. If these VCs come along and say, 'Would you work for $5?' find different partners."

Tullman named that first business Certified Collateral Corporation. ("It was completely meaningless but sounded like an insurance kind of thing.") In 1983, he took CCC public, then sold it for $100 million and segued into a company he had already started to exploit underutilized resources. While running CCC, Tullman had observed how quiet the offices got after 4 p.m., when the firm's insurance-adjuster clients went home. So he paid employees to stay late conducting customer-satisfaction surveys for car manufacturers, hospitals, and restaurant chains. "You could do all the verticals except hotels," says Tullman, "because you didn't want to call some guy's home and ask his wife how the night at the motel was." He sold that second business, Original Research, in 1990.

Listening to Tullman recount his biography, I start to experience that time-lapse sensation again. So many ventures. So many stories. So many battery changes for my microrecorder. If I were a Tribeca Flashpoint student, I would chronicle the entrepreneur's next decade in a dazzling multimedia presentation. But because all I have are words, and a limited number of those, I'm going to condense the '90s into something more utilitarian: a timeline. Imagine what follows as a series of slides illustrated with artful photography. Hell, imagine video while you're at it. And a soundtrack. Maybe something anthemy, by Queen.

1990: Eager Enterprises, a venture fund investing in early real estate and employment databases

1991: Information Kinetics/Career Network, a service aggregating college-student resumés on CD-ROMs, for distribution to employers

1991: ICOM Simulations, a developer of computer games

1992: COIN, an automotive information systems company (this was a turnaround rather than a start-up)

1993: Monumental Art and Events, a marketing firm producing paintings and memorabilia commemorating major national events

1993: Imagination Pilots, a developer of computer games based on entertainment properties, such as Where's Waldo? and assorted action movies

1994: Information America, a database and legal-data aggregation company

1995: Swinging on a Star, a Broadway musical Tullman produced

1996: The Cobalt Group, a provider of e-commerce and Web services to car dealerships

1996: JamTV (later, originally a producer of live-music webcasts, later a cluster of sites for prominent entertainment publishers, including,, and

Which brings us to the Education Decade. (End soundtrack.)

We are tooling around Chicago in a black SUV, on a drive-by tour of past triumphs. Rolling around in the back are stacks of the 64-ounce plastic cups Tullman brings to his local 7-Eleven every morning for Diet Coke. The store downsized its Double Gulp to 62 ounces a few years ago, but Tullman keeps bringing in his old cups and insists the proprietors serve him the extra 2 ounces for the same price. (They also supply him with special tokens so he doesn't have to wait for change.) We collected the vehicle from a parking garage, where it occupies a first-floor space with no cars on either side. The garage owner created the space especially for Tullman, who didn't want to climb stairs or squeeze past anything to get to the driver's door. "My rule of thumb is that someone is going to have the best seat in the house," says Tullman, as we shoot past Stop signs with an air kiss. "It may not be me. But shame on me if I don't ask for it. In every speech I give to entrepreneurs, I ask them not to make it easy for other people to say no and not to compromise."

Tullman points out an imposing brick structure standing in splendid isolation near the Chicago River. Once, it was a research kitchen for Sara Lee; today, the building houses Kendall College, an award-winning culinary school that Tullman rescued from near collapse in 2003. Named president of Kendall with a mandate to save it, sell it, or shut it down, Tullman pared the curriculum of subjects such as law enforcement and athletics, secured a lucrative contract to train Navy cooks, unloaded the dilapidated 70-year-old campus in suburban Evanston for $10 million, bought the state-of-the-art Sara Lee facility, and raised another $50 million to finance it all. The strategic and financial turnaround took 100 days; the renovation and relocation a further three months. In 2006, Tullman arranged the profitable sale of Kendall to Laureate Education, which operates campus-based and online universities.

Two blocks from Kendall, we pass the former site of Experiencia, Tullman's second education venture. In 2005, Tullman, Pollack, and a couple of investors transformed 20,000 square feet of industrial space into a miniature city for inner-city schoolchildren to operate. Every day for three years, 240 fourth, fifth, and sixth graders took over Experiencia's diminutive storefronts, its snack shops, its government agencies, and its newspaper and radio station to learn about real work in the real world. Another floor, devoted to science, featured 100 live animals and a special-effects-driven natural-disaster simulation. "I did it half because it was good for the kids and half because it was completely amazing to build my own city," says Tullman. But the Chicago schools couldn't support the program, so Tullman sold the space to the Girl Scouts, who use it for workshops and camps.

Which brings us to Tribeca Flashpoint Academy. The idea originated in 2007 with Landry, also an investor and serial entrepreneur. His son, an aspiring filmmaker, had enrolled in a four-year arts and media college and been disappointed. "He went to school for almost two years and never touched a piece of equipment," says Landry, who stepped down as chairman of Flashpoint last year. "I started looking for schools that really trained students to go to work in digital media and found a hole in the market." An education-industry novice, Landry sought out Tullman, whose resumé also boasts a stint as chairman of the Princeton Review, on the recommendation of a mutual friend. Tullman relished the prospect of preparing students for more lucrative careers than Kendall had generally provided. "Instead of chefs, they could become digital filmmakers and go to work for Pixar or Disney," Tullman says. "This time around, we would train people to be financial successes as well as doing things they were excited about."

While Paula Froehle, enlisted by Landry as Flashpoint's academic dean, recruited faculty and staff, Tullman chased students. Persuading parents to spend $25,000 on a school that didn't exist yet was no easy sell. Tullman figured the most likely targets were kids like Landry's son, who had gone the four-year route and regretted it. He created marketing material, writing and designing 57 ads in 57 weeks that ran in Chicago's free newspaper, The Reader, and other publications. ("If you're sitting at a college that's a mistake for you, now is the time to fix it," reads one ad. "Sending my son to a traditional four-year school is a waste of his time and my money," goes another.) That first year, 107 students, most in their early to mid-20s, took a leap of faith.

In late May 2007, Tullman and Landry—who had raised $10 million from angel investors—took over three floors in a stately, century-old office building across from Daley Plaza. The space, a former domestic-violence court constructed with Kevlar walls to prevent bullets passing through, was a wasteland: rubble-strewn floors, bins heaped with drywall, electrical conduits dangling everywhere. Cue renovation montage. Three months later, Flashpoint Academy (De Niro et al. were not yet in the picture) welcomed its first students to a facility equipped with technology so new, much of it wasn't yet on the market. "I didn't think Howard could move faster than he did at Kendall," says Paras, who was the IT director at the culinary school. "But this was faster."

Some of Flashpoint's technology—cameras, software, editing tools—comes courtesy of Microsoft, Canon, and other companies that are eager to test new products with the budding digerati who represent their next-generation customers. Some was developed specifically for Flashpoint. An interactive storyboard that also plays videos, for example, was designed by a company called PolyVision, with input from Flashpoint's staff and students. There are game labs and screening rooms and editing facilities. The live-music studios and sound-design suites, where recording majors create effects for other students' films and—as one of the school's outside projects—lay down tracks for the popular games Guitar Hero and Rock Band, are built on foam, and the ceilings hang on springs, to dampen the noise.

At this point, I have to address the paintings. Tullman, who is married to an artist and has two grown daughters, is a voracious collector of contemporary representational art. Hundreds of canvases—large, loud, challenging verging on pugnacious—adorn every wall in the school. They stand out against the otherwise-cool, professional décor like (I'm gonna steal from Raymond Chandler) "a tarantula on a piece of angel food cake." In fact, a painting of a tarantula on a piece of angel food cake would look right at home here. The art is meant to stimulate students, who at some point in their two years must choose an artwork and incorporate it into a story or video game. "I want them to understand that digital stuff can become sterile pretty easily," says Tullman. "There is excellence in analog."

Just after noon, Tullman sits in a darkened classroom watching for the first time a trippy video about projection mapping. Devin Wambolt, a second-year visual-effects major, narrates as his onscreen self assembles a blocky structure from boxes and paper. The student explains how he used camera, projector, and 3-D software to create a perpetually mutating three-dimensional canvas. As he speaks, the structure writhes into life, bathed in pulsing psychedelics and distorted real-time images. "Very cool," murmurs Tullman, the possibilities already percolating in his brain. Ninety minutes later, he is in a meeting pitching Wambolt's technology, among other ideas, to the team leading the renovation of Navy Pier.

Flashpoint fields roughly 70 inquiries a week from individuals and organizations wanting help producing a video, a mobile application, or an interactive marketing tool. They seek out the school for its speed of execution, youthful talent (its students represent the demographic clients often want to reach), and low price (most projects cost about 25 percent of what a professional production company charges). Flashpoint accepts 30 to 50 projects each year and assigns them to student teams, with faculty oversight. "We select projects for three major reasons," says Edward Glassman, vice president of marketing and business development. "First, we want our students to have that killer material in their portfolios so they can get a job. Second, it goes a long way for our brand to be associated with Microsoft or Sony or McDonald's. Finally, it's great outreach to prospective students."

Certainly, the school benefits when Tyra Banks yells, "Holla, Flashpoint!" on Good Morning America. Banks is one of several celebrities to bring projects to the school, which designed the cover for her novel, Modelland, featuring a computer-generated eye. Chicago Bulls point guard Derrick Rose appeared in a no-texting-while-driving PSA created by Flashpoint for AT&T Illinois.

Projects like these feed the school's scholarship fund, but the end game is jobs. Roger Ebert and his wife, Chaz, collaborated with Flashpoint on the pilot for the most recent incarnation of their film-review program, Ebert Presents At the Movies. They have since hired several Flashpoint students as interns and offered full-time employment to two, including a broadcast major who is now an associate producer. Overall, the school's graduate placement rate is 75 percent. Intent on minting graduates who are, first and foremost, great employees, Flashpoint evaluates students not only on technical prowess but also on such attributes as accountability, respect, collaboration, initiative, and attentiveness. Performance in those areas is tracked on a public graph, and the plummiest projects go to the most professionally behaved. "These standards are incredibly important to employers—in many cases just as important as technical know-how," says Glassman.

Inevitably, a few members of each class breathe in the entrepreneurial spores Tullman leaves in his wake and go on to start, or try to start, companies. In the sprawling Merchandise Mart, about half a mile from the school, Flashpoint maintains—in addition to a full-scale sound stage used for commercial and student productions—20,000 square feet of unfinished space for start-ups. Most of the embryonic tech companies clustered in this cavernous, public-garage-Spartan room are unaffiliated with Flashpoint. (Tullman offers them only cheap rent and free advice.) An exception is Tap.Me, which manages the display of advertising in video games. Tap.Me's founders met and bonded while building an Xbox game at Flashpoint. Tullman hasn't invested but did drill the team on presenting to venture capitalists. It has so far raised $1.4 million.

Justin Moore, a co-founder of Tap.Me, is exactly the kind of student Tullman wants to attract. He graduated from MIT with a degree in mechanical engineering but, finding no careers that interested him, enrolled at Flashpoint in its first year, hoping for a fresh start. "I loved it," says Moore. "I learned different stuff than I did at MIT: interpersonal skills, team-management skills, communication skills. At MIT, it was, How do you formulate solutions to problems? Flashpoint was, How do you organize and get people together to actually execute? And just seeing it as a new business in action, I got really jazzed up to start my own."

Tullman expects start-ups like Tap.Me will provide projects for Flashpoint students and also, someday, employment for graduates. Another potential employer is the quasi-incubator Hydrbox, which so far consists of Tullman, a developer, and 15 product ideas Tullman came up with while he was busy not sleeping. They include a cool technology that lets T-shirts transmit messages to mobile phones and a mechanism for managing information using your subconscious that Tullman patiently went over with me three times and I still didn't get. Tullman plans to see which innovations gain traction and then hire sales teams around them, while keeping administration and research and development centralized. "We're essentially rapid prototyping new businesses," he says.

Tullman thinks some of the technologies percolating in Hydrbox are potentially substantial companies, which he might lead at the same time as Flashpoint or possibly after it. When he launched the school, Tullman estimated he would stay seven years. That means he has three to go. He likes to move on, and then on, and then on, which he concedes may be why he is not better known. "I prefer to expand and enhance and enrich what the business is doing rather than continue to build above a certain level," he says. "A lot of famous CEOs run public companies, and I can tell you it was not fun to run a public company the times I've done that. I wouldn't even want to sit on the board of a public company."

I ask him if he's happy, and he shrugs off the question: "There's a word, anhedonic, that fits me," he says. "I'm doing important and worthwhile work. I'm pleased with what I've accomplished. There are moments of exuberance. But I would never say I am happy.

"I live to try and figure out how to be most productive," he continues. "The question to ask, every minute of your life, is, 'Is what I am doing moving something forward? Is it advancing me? Is it advancing something important?' If not, it may not be a good use of my time."