Nathan Barry
Nathan Barry’s Idea of Rich Includes a Workshop and a Ghost Town
The Kit founder built a substantial software business. His own accounts reveal how its rewards reach into family life, flying and the things he makes by hand.
For Christmas in 2017, Nathan Barry made his wife, Hilary, an elaborate jewelry box. His workshop also turned out wooden swords, axes and Batman-style throwing toys for the boys. He was getting faster with a computer-controlled cutting machine and had bought a table saw designed to protect his fingers. The ambition, he wrote, was to teach his children that something they needed could be made in the garage. Even as his software company grew, building things with his hands remained part of the picture.
That company, now called Kit, became a substantial source of wealth. In a December 2025 conversation with his executive coach, Dan Putt, Barry said it had passed $50 million in annual recurring revenue. His biography describes the business as entirely bootstrapped and reports more than $5 million in annual company profit. Kit supplies email and audience-building tools to creators; Barry’s own life shows some of the possibilities that a successful creator business can buy.
His earliest model of prosperity was a man named Fred, who owned a machine shop in Star, Idaho. Barry’s father ran a Christian bookstore and college ministry supported largely by donations. Money was tight enough that fast food and ice cream were special treats the family could not routinely afford. Fred and his wife, Shirley, helped support them; Fred later employed Barry’s father and gave his older brothers summer work. In Barry’s remembrance, the lesson was as much about hospitality and generosity as craftsmanship.
Barry began earning money at 13, cutting wooden ornaments on a scroll saw and selling them around the neighborhood for $10 to $40. At 15, he worked at Wendy’s to help pay for college classes. Web design followed, then a startup job, iPhone apps and a book about app design that sold nearly $20,000 in its first week in 2012. His account of these years reads like an apprenticeship in selling: first at a neighbor’s door, eventually through an audience he could reach online.
Kit began in January 2013 as ConvertKit, an attempt to build the email tool Barry wanted for his own books and courses. The first goal was modest: $5,000 in monthly recurring revenue within six months. It missed. Growth stalled, and entrepreneur Hiten Shah pushed him to choose between closing the business and committing to it. Barry chose commitment. In late 2014 he invested $50,000, concentrated on professional bloggers and started direct sales, with the team personally moving customers onto the service. By the end of 2015, monthly recurring revenue had reached $98,000.
Barry’s own finances remain closely tied to the company. In April 2026, he wrote that Kit shares accounted for 95% of his net worth. He also described a secondary share transaction that valued the company at $200 million, with 3.2% changing hands. That transaction gave employees a way to sell shares while Kit remained independent.
The same account lays out where the operating profits go: 52% to the team, 8% to an executive bonus pool and 40% to owners. Barry said employees had received $9.8 million in profit sharing over ten years. Staff can benefit while the company remains independent, rather than waiting for an acquisition.
He has other income streams, too. Barry reported receiving well over $100,000 in distributions from newsletter growth agency Paperboy in 2024. That year’s review also described partnership breakups and a costly water leak in his rental-property businesses. There is capital to deploy, but also property to repair and business relationships to untangle.
Boise anchors the family story. Barry and Hilary bought their small farm in 2017 for $517,000, using a 30-year mortgage with 20% down. Its workshop became a place to make things together. In his 2023 review, Barry described helping their son August produce cutting boards and Idaho-shaped plaques for a roadside stand. The family’s three boys—Oliver, August and Josiah—appear throughout his essays as participants in the life he is building, from sports and projects to camping trips.
Some choices have reduced income to make more room for family life. The Barrys took their guest cottage off Airbnb in 2023, deciding the money did not justify the intrusion and preferring to keep it available for relatives. His next annual review described friends staying there before recording podcasts with him, and a doubles pickleball tournament with Oliver.
Flying is the more expensive pleasure. In his 2024 review, Barry put aviation’s annual cost at about $100,000. He had earned his private pilot license that March after a failed first flight exam and a successful retest. On a trip with Hilary to the Tetons, her questions about Yellowstone prompted an aerial detour over Old Faithful. The plane gave them a way to turn curiosity into an afternoon’s itinerary.
His most unusual investment took that appetite for a project much further. In 2018, after a tip from his friend Ryan Holiday, Barry joined ten investors buying Cerro Gordo, a former mining town in California. The group paid $1.4 million for the town, mine and 336 acres. In a December 2025 podcast conversation, Barry said he and Holiday each owned 10%. A software fortune had acquired a stake in an actual ghost town, with restoration work and a landscape to explore.
Barry has also written about the question affluent parents eventually face: what will this do to the children? In 2022, he took Oliver and August to Mexico City with New Story to visit housing projects the family had helped fund. He described wanting them to understand lives beyond their own comfortable circumstances. It is a recurring concern in his essays: how to pass along the possibilities of wealth while keeping an understanding of what money changes for other people.
When Putt asked him to imagine what his 13-year-old self would think of his recording studios, Barry became emotional. The important part, he said, was that other people could use the tools to make what they imagined. Read alongside his memories of Fred’s shop and his own garage projects, the connection is hard to miss. Barry’s definition of success still leaves room for the person learning to build something for the first time.