Holly Agra tilts her head upward, letting sunlight settle on her face.
She stills her fingers from fiddling with her iPhone. She gazes at the bridges and the current of the river, relishing the vista from the deck of Chicago's Leading Lady, the biggest boat in her company's fleet.
Agra glances at the vast Montgomery Ward building, which now houses Groupon and contains the desks of thousands of employees. She contemplates her own outdoor workplace and its riverside scenery.
"Aren't we lucky we're outside?" she said. "And they're all inside?"
Chicago's First Lady Cruises has been the official fleet of the Chicago Architecture Foundation River Cruise for 19 years and is the sister company of Mercury, Chicago's Skyline Cruiseline. Agra, 54, has been at the helm of growth at both since she smashed a bottle of Dom Perignon on the hull of the First Lady's first ship in 1991.
A year later, she proved to be an executive with insight and guts, evident when massive flooding left her boats stranded. She didn't call or write the mayor's office to say she needed help; she sent a telegram. It worked, and the city sent the U.S. Army Corps of Engineers to assist.
The four ships of the First Lady fleet are moored at the southeast side of the DuSable Bridge at Wacker Drive and Michigan Avenue, along with the Mercury and Skyline Queen. (A smaller yacht, the Lady Grebe, is tethered at Burnham Harbor.) Warm weather prompted some early ventures this spring, and NATO diplomats kept the boats busy last week, but Memorial Day weekend marks the start of high season for the seven vessels, which took about 250,000 people up and down the Chicago River and along Lake Michigan last year.
It's a year of national and international scope for Agra, too. In her second term on the U.S. Travel and Tourism Advisory Board, she has been urging the federal government to ease visa restrictions so that tourists from countries like China and Brazil can have an easier time visiting America, and in turn, Chicago.
"She's a real champion for Chicago," said Grant DePorter, the CEO of Harry Caray's Restaurant Group, which partners with First Lady to provide catering. "She just thinks for the greater good and is really a huge visionary, and those are the things that will help keep Chicago strong and competitive."
Of Bob and boats
Boats, and the business of boats, didn't enter Agra's life until she was 19 years old. That's when she met Bob Agra.
Bob has one of those quintessential Chicago family stories, beginning when his grandfather, Arthur Agra, emigrated from Portugal to start carrying passengers around Lake Michigan in 1935. His boat, which departed from Navy Pier, carried six passengers.
In the 1950s, Arthur and his son, Robert, Bob's father, moved their boats to the southwest side of the Michigan Avenue bridge, now the DuSable Bridge, and began operating as Mercury Sightseeing Boats. By then, their vessels could carry 40 passengers.
In the next decade, they expanded their operations to the State Street bridge and upped their capacity to 200 passengers. Robert later consolidated the fleet at the Michigan Avenue site, which his son moved east in 2001.
A couple of years before Holly and Bob met, Robert died after a series of heart attacks, leaving his son in a precarious position.
"Your dad passes away when you're 18 years old, you don't go to school," Bob said. "You keep the family business going."
In 1977, Holly was studying business administration at Harper College in Palatine when, through friends, she met Bob. While running the family business full time, Bob had started taking night classes in accounting. He still remembers the restaurant where he decided he would marry her.
Aptly, the eatery was named Down the Hatch.
"She was very nice, very beautiful, and she had a lot of business sense," Bob, 54, said of meeting Holly.
"No! I didn't have any business sense," she said, laughing.
Bob persisted with his point as they ate breakfast on a recent Wednesday at their home in Deer Park.
"I was explaining about the boats, and she was very interested in them. She had a knack," he said. "In the past, when I've explained it to people, they just sat down with a dumb look on their face."
A year after meeting, Bob and Holly got married. Holly had received her associate degree in business administration at Harper. As for whether to continue college classes or help her husband, Holly said, "It was a decision to say, 'Let's pause, see what this is about, and maybe I'm going to come back to (school).'"
She never did go back but has made up for it with real-life experience, as well as executive education classes at Harvard Law School.
For their honeymoon, which came about the time they went into business together, the Agras spent six weeks in Europe.
To cross the Atlantic, they took not a plane but an ocean liner, the QE2.
Clarity from crash
Everyone goes through some kind of trauma, Holly believes, that crystallizes what's important in their lives.
For Holly and Bob, it happened in 1982.
It was May 1, the opening day of their boating season. They were leaving the wedding of some friends and driving in Lake Barrington.
They have no recollection of what happened, but their Volvo smashed into a tree. Bob flipped out of the sunroof, cracked his vertebrae and wore a halo brace for three months.
Holly was crushed in the passenger seat. She broke bones in her knee, her arm and her ribs. She suffered punctured lungs.
Her left knee turned inside out, straining the nerve that goes down to her foot. To this day, "I'm not able to wear as stylish of shoes," she said.
For three weeks, her husband didn't know who she was. She and Bob spent a month recuperating at Advocate Good Shepherd Hospital in Barrington and another four months lying in bed at home.
"And that was before cable TV," notes Holly.
Her mom, Marjorie Tucker, quit her job to take care of them. Her dad flew up from Dallas multiple times to visit and help with his daughter and son-in-law's business.
"I didn't remember being in that much pain," Holly said, "as much as just being incapacitated."
Holly and Bob missed the entire boating season that year but healed without many physical reminders, except for Bob's few small scars from his brace and Holly's flat-soled shoes. They went on to have two sons, Bob, now 26, who has joined the family boating business full time, and Tim, now 24, who's in law school in Los Angeles.
The Agras also gained something intangible.
"When we emerged from that trauma," said Holly, a glow in her clear blue eyes, "we emerged more mature and ready to do something interesting with this business."
Seeing beyond horizon
For Holly, that something interesting entailed creating another company to offer boats that would allow passengers to dine onboard.
"Holly is why the business has grown and is as successful as it is," Bob said. "Because she's a visionary."
Agra may say that she had no business sense when she was attending Harper, but for her, entrepreneurship began in high school. She lived in a wooded community filled with trout ponds and riding trails, attending Cary-Grove High School, wondering what to do with her summer.
She had a horse, Shamrock, but no car. So she created her own job by teaching neighborhood kids how to ride her horse. Holly's father, Bob Hawkins, 77, who now lives in Pinehurst, N.C., said what surprises him isn't that his daughter is running her own company, it's that it concerns boats, not horses.
A year later, she snagged a summer job in Gurnee at Great America, which then was owned by Marriott, and "loved the fact that every day I was serving customers, and I loved working outside." While she attended Harper, Holly worked as an assistant ad buyer at A. Eicoff & Co.
When she began operating Mercury, Chicago's Skyline Cruiseline with Bob, where she is now vice president of sales, it had two boats, the Mercury and the Skyline Queen.
The expansion began with the $1.2 million construction of Chicago's First Lady, the first sightseeing boat in what would become Chicago's First Lady Cruises. A half-dozen years after its christening, that boat served as the spot where Julia Roberts and Dermot Mulroney danced in the movie"My Best Friend's Wedding."
The Agras' boat-building continued in the 1990s and 2000s, culminating last year with the launch of Chicago's Leading Lady, the newest and biggest in the fleet. At a cost of $3.2 million, it's also the most expensive. First Lady boats range in size from holding 80 to 250 passengers each, though capacity can vary somewhat, with 90-minute architectural cruises costing $35 to $38 per person. Agra declines to release revenue figures.
Diane Uczen, who started with Mercury Cruiseline as a deckhand tour guide 40 seasons ago and is now director of group sales, calls Holly "the driving engine of the company."
"She's truly a visionary. She's my Burnham," Uczen said, referring to Daniel Burnham, the famed architect and principal author of the "Plan of Chicago."
"She's can see what growth the company is capable of, and she creates a space that is just unbelievable."
Running a cruise line has not been without its hazards.
There is Agra's Google problem, for one: A single bad review that calls her by name shows up high in her search results. Social media, she admitted, is something she needs to be savvier about. To help, she hired a social media manager for these last two cruising seasons.
"Absolutely, it's a weak spot," Agra said. "I have a lot of great successes, but it's a weak spot."
Then there's the incident with the Dave Matthews Band.
Eight years ago, a tour bus for the band stopped on the Kinzie Street Bridge. Its driver unleashed a torrent of human waste into the river as Chicago's Little Lady passed under the bridge. About two-thirds of its passengers were doused.
"You may think you have learned everything in your career until something like that happens," Agra said. "We never had the type of exposure to the media like we did."
After initial denials, bus driver Stefan Wohl later pleaded guilty to misdemeanor charges of reckless conduct and water pollution and was sentenced to 18 months of probation, 150 hours of community service and a $10,000 fine.
Agra said her company's insurance paid for refunds and replaced customers' clothing. "Our customers were really the victims," she said. "We did the very best to manage their experience."
Lynn Osmond, the CEO of the Chicago Architecture Foundation, which partners with First Lady by supplying the volunteer docents for boat tours, said that during that time Agra remained "extremely focused. She's the partner you want in a crisis."
The incident has cemented itself in strange Chicago lore, and though Agra talked about it at her company's indoor headquarters in Palatine on a recent Wednesday, she said it doesn't plague her.
"It was one weird thing," she said. "We got through it."
Better navigation of city
Agra constantly looks for ways to induce tourists to come to Chicago and to help them navigate the city too. She envisions the details as she traverses lower Michigan Avenue and lower Wacker Drive. Noting the lack of pedestrians and low lighting, she suggests that better signage, brighter bulbs and a lighter color would make more people aware of this area. (Her passengers board one more level below.)
"Why not paint it white and make it more inviting?" she said, her voice echoing off the walls. "It's not scary, but I'm sure most people think it is. People see the dark walkway, and they're afraid."
When she travels, she fills her iPhone with photos of information kiosks, creative signs and painted electric boxes from other cities from which to draw ideas.
Agra has presided over a slew of boards, including the Passenger Vessel Association, where she was the first female president, the Illinois Tourism Alliance and the Greater North Michigan Avenue Association.
DePorter, chairman of Greater North, recalls how for several months, when the board was searching for a CEO, Agra unofficially assumed the duties and, without pay, kept the offices running.
"She didn't need a lot of fanfare," he said. "She just did it."
She performs all of this civic work even as she helps Bob hire about 50 seasonal employees and coordinate the yearly moves of their boats to the DuSable Bridge from a maintenance marina at 135th Street near Cottage Grove Avenue.
About once a month during the boating season, Agra takes the time to do what she did on a recent afternoon: walk across a ramp and onto one of her company's boats for a cruise.
As a docent speaks about the skyscrapers around her, she pauses to contemplate what she no longer takes for granted.
Like what came into her mind decades ago as she was wheeled out of the hospital 30 days after her car accident.
"The first think I noticed was fresh air," she said, a smile stretching across her face.
"The smell of fresh air is amazing."
Holly Agra, CEO and president of Chicago's First Lady Cruises and vice president of sales for Mercury, Chicago's Skyline Cruiseline.
Family: Husband Bob, 54, and sons Bob, 26, and Tim, 24.
Lives in: Deer Park and River North.
Education and training: Associate degree in business administration from Harper College in Palatine and a certificate from the Program on Negotiation at Harvard Law School.
Volunteers with: U.S. Travel and Tourism Advisory Board, Illinois Export Advisory Council, Greater North Michigan Avenue Association, the Economic Club of Chicago, the U.S. Travel Association and the Passenger Vessel Association.
Most frequented restaurants: Bandera, Harry Caray's, Osteria Via Stato, Phil Stefani's 437 Rush and Chipotle — all within walking distance of the boat dock.
Goals for this cruising season: Increase visibility to international visitors (the aim is to offer literature and website resources in five languages) and promoting partnerships, like with Broadway in Chicago and the John Hancock Observatory, as well as special events and tours, to local residents.
Favorite thing to do on a day off: Go to a Cubs game.
Last movie date with her husband:"Titanic" in 3-D.
Most admires: Walt Disney. He "managed by walking around. If I want to be the best that I can be, it's not here at my desk."