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He Sold His Third Company for $1.4 Billion. And Put Off Retirement to Start His Fourth

Serial entrepreneur Don Brown launched his software business LifeOmic when he was 60, and has no plans to slow down. He’s finally having fun.

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When serial entrepreneur Don Brown sold Interactive Intelligence, the third software company he’d founded, for $1.4 billion in 2016, his kids begged him to retire. But Brown, now 65, says he knew he wasn’t done.

That same year Brown founded Indianapolis-based cloud and mobile software company LifeOmic, which aims to reduce the time it takes for researchers to identify the problem with a medical patient. It’s his first venture into health care, but the work he’s doing has been a longtime passion. Brown graduated from medical school in 1985, but before he did he also got hooked on computer programming. He started his first software company while a student.

“There was some nagging feeling that I hadn’t accomplished what I had set out to do with my life,” he says. “So I wanted to take a shot at it.”

Brown says his time at the “little company” which he started with a friend, a program to help car dealerships quickly compute customers’ monthly payments, was meant to be atemporary detour before he went into medical research.

But after selling his company to General Motors in 1986, Brown says, he was even more motivated to stay in the business world. He used the $800,000 he made to launch a second software company, but committed the “classic mistake” of not having a clear plan, and quickly ran through the money.

He was foolish to think, he says, that one success meant he’d find another: “I went from thinking that I was the smartest guy in the world to thinking I was the biggest idiot on the planet.”

Luckily, he found a partner in venture capitalist Bob Compton, who invested in the company and became a mentor to the then-30-year-old. Brown launched Interactive Intelligence in the mid-’90s, taking it public in 1999 before the 10-figure sale five years ago.

Here’s what Brown has to say about the rewards of entrepreneurship that have kept him going through four companies and more than three decades.

Finding solutions

For Brown, being an entrepreneur meant access to “unlimited possibilities.” He was drawn to startups because they allowed him to tackle problems that bigger companies such as Google and Amazon haven’t solved.

Collaboration

Teamwork is at the core of a successful startup, Brown says: “There’s just nothing more thrilling, that I’ve found, than being able to work with a group of smart people and attack a hard problem. It’s intoxicating.”

He considers himself, first and foremost, a cheerleader for his team. At LifeOmic, he asks for weekly status reports from his staff of more than 100, and reads every note. He says the worst thing that can happen, especially at a tech company, is for people to feel like they don’t matter: “That just becomes the death of an entrepreneurial company.”

A passion for health care

Brown says that planning the road map for LifeOmic is the most fun he’s ever had. It’s also the most impactful work he’s ever done. Before he sold his third company, he’d enrolled in a master’s program in biotechnology, a topic he’d been passionate about since college. That’s where he learned about personalized medicine and became convinced that health care is at an inflection point. He invested $20 million of his savings to launch LifeOmic. In 2020, the company generated $5 million in revenue, up from $2 million a year earlier.

“I’m not looking past this,” he says. “I think this may consume me for the rest of my career.”

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Biden Causes Sighs of Relief Among World Leaders Even As G7 Divisions Linger

When President Donald Trump used his elbows at international summits, it was to throw them — on trade, on Russia and, once, to help remove the Montenegrin prime minister from his path to a photo-op.

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When President Donald Trump used his elbows at international summits, it was to throw them — on trade, on Russia and, once, to help remove the Montenegrin prime minister from his path to a photo-op.

His successor Joe Biden used his elbows differently this week. Arriving to his first global summit, he crooked his arm to extend pandemic-era greetings to a group of leaders who no longer have to tiptoe around a truculent and often angry American president.

Officials attending this week’s Group of 7 summit on the Cornish coast in England are emerging shell-shocked after four years dealing with a US president who often appeared intent on injecting animosity into their gatherings. In front of cameras and behind-the-scenes this weekend, officials said the abrasive interjections and lengthy tangents Trump brought to world summits were absent, replaced by a more businesslike and predictable agenda, including on areas of serious disagreement like China.

Asked alongside Biden on Saturday whether the United States was back, French President Emmanuel Macron answered yes.

“Definitely,”

…he said, waves crashing in Carbis Bay in the background.

Even the special guest at a Friday night reception took note of the new vibe.

“Are you supposed to be looking as if you’re enjoying yourself?” quipped Britain’s Queen Elizabeth, who later was pictured in friendly conversation with Biden and his wife outside a futuristic biosphere, her son Prince Charles and his wife Camilla clutching drinks in the background.

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How JetBlue Founder David Neeleman Launched a New Airline During a Pandemic

Neeleman has overcome some crazy setbacks on his way to becoming the most successful serial airline entrepreneur in history. So why would he let a global pandemic get in the way of launching his latest carrier?

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THE ICY WEATHER SYSTEM that trundled up the Atlantic Seaboard and glazed New York City on February 14, 2007, was nasty, but not the worst that airlines had ever confronted. Mainline carriers such as American and Delta knew the drill. They canceled flights in anticipation while moving equipment and crews to sidestep the storm and minimize disruptions. The newer kid on the tarmac, JetBlue, flew into the storm face first. And flopped.

The low-cost carrier was barely seven years old, growing rapidly and happily because customers loved its panache, pricing, and product–comfortable seating, free satellite TV, and freewheeling yet attentive flight crews. Concentrating its fleet in New York and Boston made the carrier more vulnerable to winter weather, though, and as the storm began to wreak havoc on operations, JetBlue swiftly learned that its communications and logistics networks had not scaled with the rest of the outfit. With crews stuck out of place, the airline would cancel more than 1,000 flights over five abysmal days, stranding customers from the Caribbean to Queens. One jet full of passengers sat on the tarmac for eight hours. The debacle ultimately cost the airline $30 million.

Even before the storm had passed, JetBlue founder and CEO David Neeleman was conducting a nonstop apology tour, vowing to upgrade systems and make things right by customers. “This is going to be a different company because of this,” he told The New York Times. He was right about that. Three months later, JetBlue announced that Neeleman was leaving the CEO post and becoming chairman. At least Neeleman wasn’t aboard a flight when his own board shoved him out the door.

If you are looking for a case study of an entrepreneur who gets repeatedly sucker-punched by exogenous events, Neeleman is it. He’s also a study in rebounding. In the early 1990s, he built his first airline, Morris Air, out of the wreckage of his own failed travel agency. He launched JetBlue less than two years before 9/11 grounded the airlines for weeks, curbed travel for a year, and bankrupted most of the industry. Then came that storm. “You can’t control everything,” he says now, without any particular malice.

“I wrote an email to the crew and said, ‘It doesn’t really matter what happens to you in life; it’s how you deal with it.’ “

Neeleman began to build Breeze, his fifth airline startup, just before Covid-19 emptied the nation’s airports. That was after he’d returned from Brazil, where he started the wildly successful Azul Airlines in 2008. “I had 50 people hired for Breeze and we were moving along the track,” he says, munching airline snacks on a recent Monday in the upstart’s empty offices in the basement of a beige building in Darien, Connecticut. “It would have been easy for me to say, ‘Sorry, I just can’t do this.’ ” While major airlines, including Delta, United, and American, would get more than $50 billion in loans and grants from the federal government to weather the pandemic, Neeleman would have to plow his own money, some $30 million, into his fledgling business. (The company later got less than $1 million in PPP money.) “But a lot of the Breeze team left their jobs to come here,” he says, “and I just felt that I owed it to them to do it. So I said, OK, let’s make this happen. Let’s keep a foot on the brake and a foot on the gas.”

After more than a year-long takeoff roll, Breeze gets airborne on May 23 with flights in 16 cities beginning with Charleston, S.C., Tampa, Florida and Hartford, Connecticut. The network will then expand through July 22 as far west as Tulsa, Oklahoma and also including Northwest Arkansas (aka Bentonville, where Walmart is headquartered.) In October, Breeze will expand again when the first of its Airbus A220s arrive. Ticket prices will initially range from $39 to $89 one way.

Breeze’s initial route map. The company says that 95 percent of its routes currently have no airline serving them nonstop. COURTESY COMPANY

We tend to think of the airline industry as a business with a high barrier to entry–all those pricey planes and terminals. But entry is not nearly so difficult as keeping an airline flying profitably over a long period of time, as dozens of defunct carriers (Braniff, anyone?) can demonstrate. Neeleman’s ability to spot opportunity and pair the right customer service with exacting operational efficiency has helped him defy the odds more often than any other airline entrepreneur. So has a sort of tunnel vision that comes with attention deficit disorder–a disability that led to one huge career setback but also fueled his success.

“There are two phrases I’ve heard a lot,” he says. “One is, ‘Well, David, if that was such a good idea people would have done it already.’ Really? The other is: ‘David, It’s not that simple.’ ” He pauses. “Well, yes, it is–it is that simple.”

THE HISTORY OF AVIATION is filled with dashing figures. Pan Am co-founder Juan Trippe was a true titan who made air travel glamorous in the 1930s and introduced the jet age. Eddie Rickenbacker, the unkillable racecar driver and World War I fighter ace, bought and built Eastern Air Lines. Howard Hughes, the wildly eccentric entrepreneur, airplane designer, and Hollywood producer, largely created TWA. Fast-forward and there’s Richard Branson, the music mogul who brought his personal Cool Britannia brand to Virgin Atlantic. And let’s not forget Herb Kelleher, a fun-seeking Texan lawyer who loved people, cigarettes, and Wild Turkey (not always in that order) and co-founded Southwest.

Then there’s Neeleman, just a guy from Salt Lake City. And it is he–a casual, approachable fellow in a fleece vest with all the menace of a suburban dad–who may prove to be the most relentless innovator of all. Breeze, whose inaugural flight will take off in mid-May, is a reimagining of what high-quality, low-cost air service can look like. Ever since JetBlue, Neeleman has, like the kid peering into the circus tent, longed to get back into the U.S. airline industry. But just wanting something doesn’t make a business plan, so for years he looked for the right angle and moment.

The opportunity that revealed itself was this: The major players had not only plumped their profits in the past decade, but had also plumped their costs. Their labor contracts had grown fatter–which was only fair, given their growing profitability. To compensate for rising costs, the big carriers were diverting more travelers through their hubs, where they could fill the bigger planes that they were buying.

Neeleman had seen this before–it’s a repeating cycle in his industry–and he knew it opened the door to flying directly between smaller markets. Allegiant, Spirit, and Frontier, which created the ultra-low- cost-carrier (ULCC) segment, had already taken advantage of that opening. Neeleman’s angle: Use technology to offer better service and a little more class than the ULCCs but keep fares just as low–and sum it all up for people by calling Breeze “Seriously Nice.” (The company originally toyed with the term “the world’s nicest airline.”)

So it is that Breeze takes wing in what is either the best or the worst time in history to start an airline. Worst because the big carriers have burned cash at a rate of $25 million to $30 million a day in 2021. Best because vaccinations and herd immunity will allow people to travel again freely. Breeze will be waiting for them with a fleet of 13 Embraer 190s and E195s. The company will add long-range Airbus 220s in the fall.

In the air, Breeze won’t pile people on top of one another, won’t slam them with excessive fees, and will offer three seating categories: Nice, Nicer, and Nicest–the last a value-priced business-class option on the A220s. At launch, Breeze will fly 49 direct routes from 15 cities, beginning with Tampa to Charleston, North Carolina; other cities include Pittsburgh, Nashville, and New Orleans. Think Rust Belt to Sun Belt.

The linchpin is a passenger app that Breeze will use to lower costs while removing friction and enhancing the customer’s experience–from reservations to check-in to baggage to ordering food or a ride home. “When I started JetBlue, it was a customer service company that just happened to fly airplanes,” Neeleman says. “Breeze is a technology company that just happens to fly airplanes.”

After founding JetBlue and getting pushed out, Neeleman launched Azul Airlines in Brazil. Those are just twof of the carriers he’s created. GETTY IMAGES

NEELEMAN, 61, got into the passenger aviation business through a side hustle that went upside down. He was born in Brazil, where his father was first a Mormon missionary and then a journalist. After growing up mostly in Utah, Neeleman, too, got sent to Brazil for his mission. After he came home, a University of Utah classmate related how a friend had time-shares in Hawaiian condos that he couldn’t move. Neeleman, who got started in business at the age of 9 in his grandfather’s grocery, asked for a meeting. In the deal he struck to market the time-shares, he’d pay the owner a set price per night, and anything above that was his to keep. He cleared $350 on his first booking; soon other time-share owners were asking for help too.

He took the next logical step, buying airline tickets in bulk at a discount and packaging them to his Hawaii-bound condo customers. Before long, he had a $6 million company. He dropped out of school. And then, shortly before Christmas 1983, he got a call from the startup airline that had been flying all of his customers. It was going out of business. Neeleman’s company, in turn, went bust returning money to customers whose vacations had been ruined.

Like his hero, Southwest co-founder Herb Kelleher, Neeleman is a people collector. And for Breeze, he got part of the JetBlue band back together.

June and Mitch Morris, who owned a Salt Lake travel agency, had taken note of what the young entrepreneur was doing. Under their wing, he set up shop again, this time as Morris Air–first as a charter service, and then as a scheduled airline. In expanding Morris Air, Neeleman and the Morrises studied Southwest and its CEO, Kelleher, intently, and they copied as much as they could in both operations and culture. By the 1990s, they had expanded to more than a dozen cities.

In 1993, June Morris, ill with cancer, contacted Kelleher to ask about combining their two companies. Southwest bought Morris Air for $129 million in stock, and Neeleman moved to Southwest as part of the deal. (Happily, June Morris would recover.) To Neeleman, it was a dream scenario, because he would get to work with Kelleher, his hero, and had a shot at taking over the company one day. “He led me to believe that if I minded my P’s and Q’s, I would be his successor someday,” Neeleman told NPR in 2019.

Five months later, Kelleher fired Neeleman. The reasoning: Even your biggest fans can’t take any more of you, Kelleher told him. Neeleman wasn’t minding his P’s and Q’s as much as obsessing over them, trying to make his mark on Southwest and failing to keep his ADD in check. He’d been in charge of merging the two organizations over a two-year timeline. He’d gotten it done in six months but had driven his colleagues to distraction with his intensity.

Back in Salt Lake once again, Neeleman dreamed of starting another domestic airline, but he had signed a five-year noncompete clause. He looked to Canada and became an investor and co-founder of WestJet. And he thought about innovations he could bring to the industry even without planes. A relational database that Neeleman and a Morris Air colleague had developed to analyze fares, schedules, and profitability, as well as issue e-tickets, became the basis for a new reservation and data platform, Navitaire. It’s used by many airlines today, including Breeze. The pair sold Navitaire to Hewlett-Packard in 1998.

When he founded JetBlue in 2000, Neeleman leaned heavily on one of the concepts he’d borrowed from Kelleher: servant leadership. (The phrase was actually coined by AT&T exec Robert K. Greenleaf.) It’s a popular philosophy and simple concept: You work for your employees, not the other way around–and one of the key aspects is walking the talk. If you make it everyone’s responsibility to serve the customer, then you’d better do likewise, boss. Kelleher would regularly work on board, serving drinks (naturally) and even helping clean planes–quick turnarounds were vital to Southwest’s success.

Neeleman transported the concept of happy people running a happy airline to New York. He moved his family east–not easy with nine kids in tow–and raised $135 million. And, like Kelleher, he set the tone by prowling JetBlue’s planes, serving beverages, asking customers how he could do better. And he helped clean the jets. “The more people you serve, the more lives you change, the happier you are too,” he has said.

Like Kelleher, Neeleman is a people collector. For Breeze, he got part of the JetBlue band back together. Critically, he added recruits from ULCC pioneer Allegiant, who brought with them strategic financial insights. “A lot of the team members joined for a similar reason: They worked with him in the past or they knew he was a visionary who could create something special,” says CFO Trent Porter, a former Allegiant executive.

“It’s his energy. His leadership style is so different from that of most CEOs,” says Doreen DePastino, Breeze’s vice president of inflight, station operations, and guest services and one of the JetBlue tribe. “He really wants to know his team members. People gravitate toward him.” When you combine vision with charisma, it’s easier to get people to buy into ideas that might seem far-fetched, such as putting a television screen in every seatback (a JetBlue innovation). “People would say, ‘This isn’t going to work,’ and all of a sudden we’d do it, and it would work,” DePastino says.

David Neeleman. PHOTOGRAPH BY MACKENZIE STROH

THE STRATEGIC CHALLENGE of running an airline boils down to this: Where do we fly, at what operating cost level, and how do we differentiate customer service? These are analogous to issues most businesses face, but in aviation everything is magnified. At JetBlue and now Breeze, Neeleman has sought new answers.

The “where” question has been perhaps the easiest one to figure out for Breeze–because, even before the pandemic, both the major airlines and the ULCCs were giving up turf. Partly because of their union contracts, which limited their ability to fly smaller jets, the majors were packing more people onto bigger planes. As the ULCCs matured, they did the same thing. “With bigger planes, you have to chase bigger and bigger markets,” explains Lukas Johnson, Breeze’s chief commercial officer, a job he held at Allegiant. Small and medium markets get left behind. “A lot of cities in the middle of the country haven’t seen a lot of seat growth in recent years,” he says.

The Breeze app is designed to eliminate chokepoints between passengers and planes. That means fewer people on the ground and lower cost.

When Breeze analyzed the data, it discovered a whole category of cities and routes being underserved. The FAA compiles a statistic called passengers daily each way (PDEW) that contains exactly where people are traveling and what they are paying on average. A market such as Huntsville, Alabama, to Orlando has relatively low PDEW because it’s inconvenient to fly between those two points; passengers have to change at Atlanta or Charlotte. In city pairs like this, Breeze thinks it can expand the PDEW exponentially by offering direct service. “Suddenly, people look at it and say I can fly there in an hour and for 59 bucks. I’m going to go three or four times a year. It just creates a market,” says Neeleman. (In this case, the market is called VFF, as in visiting friends and family.)

Breeze also aims to gain a cost edge in the types of planes it flies. Most airlines aim to optimize a metric called cost per available seat mile, which is measured against revenue per available seat mile–the general idea being that revenue should exceed cost, which is variable. At Azul, Neeleman came to understand that an airplane’s trip costs–the fixed costs–could be just as important in gaining a competitive advantage. And that’s where an efficient Airbus 220-300 could win. Running that jet, for instance, costs just a third of what the larger A321 costs. The bigger jet may have lower average seat cost, but has much higher total costs, especially as the distance expands. “In that case, the lower trip cost wins,” says Johnson.

There’s no formula for the third leg of Breeze’s strategy, which the company, after some refinement of the catchphrase “the world’s nicest airline” now calls “Seriously Nice”. One thing nice is not, says Neeleman, is an employee who smiles at you after you’ve waited in line for 30 minutes. The Breeze app is designed to eliminate chokepoints between passengers and planes. That means fewer people on the ground and lower cost.

Breeze is also introducing a program in which it will hire college interns from Utah Valley University and mold them into customer service machines. In exchange for salary, free tuition, and housing, the students will undergo training and then work 15 or so days a month while taking their college courses online. “The big thing is we are going to provide a great service with kind people on a beautiful airplane with a fun atmosphere,” says DePastino.

As Neeleman has prepared for Breeze’s launch over the past year, the pandemic has changed the industry’s chessboard in the company’s favor. The majors were forced to drastically reduce their fleets, retiring the least efficient jets and abandoning marginal markets wholesale. That’s a scenario made for Breeze. “Larger markets are on our list now,” says Porter. “The total space we can address is actually larger.”

That window won’t be open for long. The recovery of the domestic airline industry is gaining momentum by the month, and airlines are restoring service as fast as they can. Airports and jets will fill. There will be more and longer lines, and customers with frustrations. Neeleman, who cannot abide lines–they signal inefficiency and inattention to customers–will be there observing, serving the occasional customer himself, and always, always looking for new angles. “It drives me crazy when I go to an airport and walk by Starbucks and there are 50 people in line,” says a man who doesn’t even drink coffee. “How in the hell can we reimagine this whole thing?”

The data suggests that roughly one new airline a decade actually thrives. Neeleman’s done it an unprecedented four times and thinks he can do it again. His record suggests it should be a breeze–albeit with occasional turbulence.

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Cape Cod diver left with a whale of a tale after a humpback spat him out

Lobster diver Michael Packard was nearly swallowed by a whale off the coast of Cape Cod on Friday, June 11.

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A Cape Cod lobster diver is safe Friday, following a fluke encounter with a humpback whale that nearly made him the leviathan’s lunch.

Michael Packard was diving off the coast of Provincetown, Massachusetts, Friday, when the capital cetacean caught him unawares.

“I got down to about 45 feet of water, and all of a sudden I just felt this huge bump, and everything went dark,” Packard told CNN affiliate WBZ. “And I could sense that I was moving, and I was like, ‘”Oh, my God, did I just get bit by a shark?'”

“Then I felt around, and I realized there was no teeth and I had felt, really, no great pain,” Packard said.

“And then I realized, ‘Oh, my God, I’m in a whale’s mouth. I’m in a whale’s mouth, and he’s trying to swallow me.'”

Packard, an experienced diver, told WBZ that he still had his breathing apparatus on in the whale’s mouth.

“One of the things that went through my mind was just, ‘Oh, my God, what if he does swallow me, and here I am, I’m breathing air, and I’m going to breathe in this whale’s mouth until my air runs out?'” he said.

“I thought to myself, ‘OK, this is it. I’m going to die.’ And I thought about my kids and my wife,” he said. “There was no getting out of there.”

After what Packard estimated to be about 30 seconds in the mammal’s mandibles, he said the whale surfaced quickly and spit him out.

“All of a sudden he went up to the surface and just erupted and started shaking his head,” Packard said.

“I just got thrown in the air, and landed in the water and I was free and I just floated there.”

“I couldn’t believe it,” he added. “I couldn’t believe I got out of that. And I’m here to tell it.”

‘A surprise to all involved’

Packard was pulled out of the water by a crewmate, rushed ashore, and taken to a nearby hospital. In the end, Packard said, he was “all bruised up,” but whole.

Biologist Jooke Robbins, the director of Humpback Whale Studies at Provincetown’s Center for Coastal Studies, said the unusual encounter was most likely an accident. 

“We don’t really see humpback whales doing anything like this normally,” Robbins told CNN. “I think it was a surprise to all involved.

“Robbins said that Humpbacks often engage in so-called “lunge feeding,” in which a fast moving whale tries to gather a large volume of food in its mouth quickly.

“When they do that, they don’t necessarily see everything,” she said. 

She added that Packard was unlikely to have been swallowed, as, despite their massive mouths, their throats aren’t large enough for a person to fit through.

Charles Mayo, also a marine biologist at the Center for Coastal Studies, agreed.

“It’s a little like sitting down to a really nice meal, and into your mouth flies a fly,” he told CNN. 

Mayo said his son, Josiah, is the captain on Packard’s boat, responsible for tracking the diver’s movements by his air bubbles. Mayo told CNN he was there when his son brought Packard ashore, and emergency services immobilized him and brought him to the hospital.

Mayo, like Robbins, could not recall a similar situation in which a diver ended up in a humpback’s mouth.

Packard was in real danger, Mayo said, if not from the whale’s gullet, then from the air pressure in his own lungs as the whale surfaced to spit him out.

“If you come up to atmospheric pressure, and you’ve held your breath, you could develop an embolism,” Mayo said.

“He must have kept his cool,” Mayo said. “To get out of a situation like that you have to be a top pro.”

“The reason he’s still around is because he’s smart,” Mayo said of Packard. “He’s a smart guy, he’s a tough guy, and he’s a lucky guy.”

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