Kerry Frank’s business began with a distinctly unglamorous object: the airline pilot’s bag of paperwork. Manuals had weight. Revisions had to reach people. Somewhere between the printer and the cockpit, an industry with the means to cross oceans was still carrying its instructions around in bulk. Frank saw work that could be made easier. First, she had to persuade the people doing it.
She and her husband, Dude Frank, co-founded Comply365 in 2007, working from their home’s basement in northern Illinois. The origin suits the product: useful things being assembled below stairs while everyone else carried on upstairs. There was no grand office to lend the proposition dignity. The idea would have to manage that for itself.
Two hours at a whiteboard
The opening came through consulting work for an airline. Kerry and Dude brought managers together and spent about two hours mapping their difficulties on a whiteboard. They repeated the exercise with other airlines. What emerged was a business opportunity assembled from the complaints of people who already understood their own jobs rather well.
Frank’s explanation of where the idea came from was wonderfully economical: “That’s how I got my idea, was simply listening.” A whiteboard is a modest instrument with which to enter aviation. It does, however, have the advantage of allowing several departments to discover that their separate frustrations might belong to the same problem.
The product addressed the movement of information: getting documents to staff, updating them, and making them usable where work happened. The pilot’s bag supplied a visible example. Behind it sat the less photogenic business of keeping an organization’s instructions current. Paper had enjoyed a long career. Frank thought it could stand a little competition.
A family signs on
The company was also a decision about five people’s lives. Kerry and Dude had three children. Before committing themselves to the venture, they discussed the possible financial consequences as a family. Her account includes the prospect of losing what they had and living together in a one-bedroom apartment. Everyone agreed to proceed.
She called this group her home board of directors. The name is affectionate; the responsibility was substantial. A new business can consume a household’s money and time long before it produces anything worth celebrating. Frank made the stakes a family conversation. That detail gives the basement a different meaning: the company occupied the family’s future as well as its floor space.
There were experienced people outside the household, too. Former Apple chief financial officer Joe Graziano and entrepreneur Rob Ryan supported the business. Frank has credited Ryan with urging her to think more expansively. Her appetite for accountability accompanied her appetite for building. Even an ambitious founder benefits from someone prepared to ask an awkward question.
“Our clients created the software.”
Kerry Frank, on listening to airline customers
The hardware arrives. The doubts remain.
In her account of the early development, Frank described testing with a Kindle before the iPad appeared. The arrival of a color tablet changed the possibilities. She began taking devices to airlines and explaining how electronic documents could replace paper. The demonstrations did not immediately produce universal enthusiasm. Some rooms were considerably more welcoming to the familiar binder.
Speaking with entrepreneur and educator Steve Blank in 2016, she recalled being dismissed by executives who considered the proposal too far ahead of their practices. There is a peculiar difficulty in selling a useful future: the buyer must also agree to disturb a functioning present. Aviation gave that hesitation particular force. Established procedures carried responsibilities that a persuasive sales visit could scarcely wave away.
Frank kept going. The work involved understanding how an airline would adopt the software, alongside making the software itself. A tablet could attract attention on a table. Getting people to rely on it required a longer conversation about their everyday work, their documents, and their willingness to change.
A simplified view of the work Comply365 set out to improve.
One manual. One tablet. Start the clock.
One of Frank’s recollections gives that conversation a particularly good prop. Meeting the FAA with Republic Airlines, she says, she faced a regulator who put his watch on the table and asked her to demonstrate her point. A 1,300-page paper manual competed with a tablet in a search for procedures concerning a cracked windshield.
In her telling, the tablet produced the relevant material while the regulator was still turning pages. It is a satisfying scene because the argument becomes visible. The room can stop imagining the difference and watch it happen. A binder is quite an impressive object until someone asks it to hurry.
Frank also describes the collaborators who made progress possible: people inside airlines, technology partners, and regulators working through the implications of digital documents. She recognized that some airline employees wanted change already. Her task included finding them and building with them. The story has more people in it than the familiar picture of a founder alone with an idea.
A business large enough to hand over
By Comply365’s tenth anniversary in 2017, its own figures described an operation far beyond the basement. Its mobile app supported roughly 15 million flights annually, and its customers included 11 Fortune 500 companies. These were milestones from that moment in the company’s life, evidence of how widely the original document problem had traveled.
In July 2018, Frank stepped down as CEO. Tom Samuel, who had joined as chief operating officer and later become president, took over the day-to-day leadership. The transition placed an experienced company executive in charge of the business she and Dude had started more than a decade earlier.
That year also brought the Ken Hendricks “Seize the Day” award, shared by Kerry and Dude, recognizing entrepreneurship in Wisconsin. The joint recognition fits a partnership in which the technical work and the business-building had grown together. The story belonged to both founders, even when Kerry was the person taking the proposal into the room.
The next proposition had a yellow barn
Frank’s later venture required visitors to come to her. With her family, she established Hidden Creek Estates in 2021 in Roscoe, Illinois. A restaurant, an event venue, and overnight accommodation grew out of a property the family wanted to preserve. There were woods and a pond, and a barn that needed serious attention.
Discussing the project in 2021, she described a deteriorating foundation and the work needed across the grounds. Her family had already put thousands of hours into the place. Preservation was personal to her: she wanted the property to become part of the family’s legacy. The investment began before there was certainty about the approvals needed to operate.
The practical details kept multiplying. By 2024, renovations allowed the venue to serve guests throughout the year. The yellow barn’s offering expanded to include a wine and whiskey cellar, a tasting room, and a patio. Frank had been searching for antiques well ahead of the unveiling. Hospitality, apparently, permits a founder to call shopping part of the development schedule.
Rooms with a sense of humor
In May 2026, Hidden Creek celebrated five new wine-barrel guest homes. The idea had come through a friend who had seen barrel-shaped lodging while traveling. Frank said the family spent roughly two years figuring out how to build their version. A passing suggestion became a construction project, which is one way to measure how seriously this family takes an interesting idea.
The homes were named Barolo, Napa, Champagne, Rhone, and Tuscany. Each offered a king-size bed, a bathroom, climate control, and a patio. The shape supplied the joke; the facilities supplied the reason to stay. A barrel becomes a rather different proposition when one can sleep comfortably inside it.
By September, Frank was celebrating national travel coverage of Hidden Creek. She described the property as 77 acres and gave credit to the team for continuing to build and experiment. Her account of the new rooms has the same practical momentum as the software story: someone proposes something unusual, and a group of people starts working out how to make it real.
The chickens decline the business plan
Her public writing leaves room for less orderly developments. In July 2025, she described fireworks frightening the family’s chickens into the trees. She and her son-in-law spent an hour trying to coax them down. The birds kept finding fresh branches. It is reassuring to learn that experience persuading airline executives confers no automatic authority over poultry.
Family traditions supply another recurring measure of success. Frank has written about annual camping trips to Hayward, Wisconsin, continuing a connection that began with her grandparents. The trips started as something the family could afford. Over time, fishing, water-skiing, and the stories retold around the fire gave them a value independent of the holiday budget.
She now shares entrepreneurial experience through speaking and writing, with a stated interest in helping others build without losing their values. In September 2026, she announced her place in the EntreCon Midwest speaker lineup in Beloit. Her November writing on innovation offered patient advice: gather information, use relationships thoughtfully, and check what changed when a colleague withdraws support.
That patience belongs beside the persistence. Flight manuals needed a better way to reach people. An old property needed attention. A new guest room needed someone to solve its construction problems. Frank keeps returning to the work between the interesting idea and the thing people can actually use. Sometimes the next step is another conversation. Sometimes it is another branch.