When Andy Ivankovich first drove down Mill Dam Road in Comfort, Texas, he wasn’t looking for a vineyard. Truth is, he’d never even tasted Texas wine. What he sought was just a quiet slice of the Hill Country, somewhere to clear brush on weekends with his kids and let his mind rest from years of tech startups and endless flights. Yet, there it was: Singing Water Vineyards. Quiet, charming, a little rough around the edges. Andy stood in the tasting room and knew instantly that God had placed him exactly where he needed to be.
Andy’s story didn’t begin with wine or wealth. It started far away, in Mulberry, Florida, where his father’s passing when Andy was just ten left his family clinging to survival. He recalls living on $400 Social Security checks, the kindness of his church, and teachers who cared enough to pay for his dinners and Disney trips. It was a hardship, sure, but it also forged steel in Andy, teaching him early the art of resilience. “There was no money in our family at all. Not a penny extra,” Andy remembers. “My mother figured out how to make that work.”
Growing up, Andy knew work. By high school, he had multiple jobs, cutting lawns, doing odd jobs, simply to help his family survive. These early experiences instilled in him a tireless work ethic that became the cornerstone of his character. He was a top student, involved in band and cross-country, but unlike many classmates, Friday nights often meant extra hours of labor rather than leisure. College was never an option, financially impossible, he says, and so at eighteen, seeking an escape from poverty, Andy enlisted in the Air Force.
As a C-130H Crew Chief, responsibility came fast and hard. He had barely earned his first stripe when pilots began turning to him, asking, “Chief, is it ready?” When the answer determined safety and survival, it aged him quickly and permanently. Andy credits the Air Force with shaping his meticulous attention to detail and sense of leadership. But more importantly, it taught him about sacrifice and brotherhood, lessons he carries to this day.
Post-military, Andy found himself in Boston, earning a business degree from Eastern Nazarene College, marrying his sweetheart Missy, and diving into the rising tide of fintech. At USAA in San Antonio, Andy pioneered technologies that changed the way banks lend money, earning patents and national recognition. He recalls, “My area was consumer lending. I had the ability – with some really good folks – to develop the first capability of doing a loan without ever talking to a person.” After years of the corporate climb, his entrepreneurial spirit called louder. He founded iLendx, a software company that became so successful it was acquired by fintech giant Fiserv. Andy describes the moment he received the call from Fiserv’s CEO as one of the highest honors of his career, a validation of years of risk-taking and sleepless nights. Still, ever restless, he knew life had more chapters yet unwritten.
That chapter began the day he bought Singing Water Vineyards. Partnering with legendary Texas winemaker Pat Johnson, Andy set his sights on crafting bold, world-class red wines. “I just want to make really good, bold red wine, and I want to make the best cab in the world,” Andy recalls telling Pat. With each vintage, the duo refined their vision until their Cabernet Sauvignon shocked wine circles by winning Best in Class at the prestigious San Francisco Chronicle Wine Competition. Andy laughs when he remembers the moment the news came in. “Six years ago, I’d never tasted Texas wine, and here we were beating Napa at their own game.”
Yet, as impressive as the accolades are, Andy insists that the winery’s greatest strength is its authenticity. Singing Water isn’t trying to imitate California or Europe. Instead, it’s pure Hill Country, rolling hills, old oak trees, a creek winding lazily, and goats grazing by a red barn. Guests might see Andy himself pouring wine, his boots muddy, swapping stories about Air Force days or how his grandfather built Model T’s alongside Bill Ford’s ancestors. Ford Motor Company even chose Singing Water as the backdrop to launch their groundbreaking F-150 Lightning electric truck, a nod to Andy’s genuine Texas hospitality and roots. He cherishes a letter from Bill Ford that hangs in the winery, a testament to family legacy and community pride.
Community is central to Andy’s vision. He serves on local boards and mentors aspiring entrepreneurs, especially veterans. His belief in service extends well beyond profit margins. Andy and Missy spend significant time in Kauai, Hawaii, where they help veterans transition into business ownership. This passion for mentorship and community building reflects Andy’s deeply held belief in the importance of giving back.
Amid success and growth, Andy stays humble and reflective, deeply driven by integrity and faith. “I learned early on from an individual who shared with me, always remain curious and coachable,” he emphasizes. A longtime friend and admirer of pastor Max Lucado, Andy’s Christianity guides his life quietly but firmly. He speaks openly about grace, not from a pulpit, but from the simple truth of a man who knows he needs it daily. It’s this humility, mixed with ambition, that defines him best.
Family anchors Andy. Missy, his wife and partner in every venture, balances his visionary drive with grounded practicality. Their four kids grew up watching Dad take on seemingly impossible challenges. “This area was a really good place to raise kids,” Andy says. “I wasn’t going to take my kids to a city just so I could get more of a direct route on an airplane.”
Today, Andy’s juggling roles again. As CEO of Baker Hill, a financial technology company dedicated to empowering community banks, he applies the lessons learned through decades of innovation. Yet, weekends find him back at Singing Water, pruning vines or walking the fields with Missy, dreaming new dreams for the land and community he loves. “I’m passionate about our area, my friends, and neighbors. I think we have to protect our private property rights… we have to develop smarter here in the Hill Country,” Andy states firmly.
Andy often reflects on his life’s journey, remarking that life is long, relationships matter, and every encounter shapes your path. He emphasizes integrity as a non-negotiable, recalling lessons from his business professors that true success is not just financial, but ethical. At Baker Hill, he remains dedicated to community banks, believing they form the backbone of local economies, crucial to American prosperity.
On quiet evenings at Singing Water, Andy contemplates the future. He sees endless opportunities for growth, yet remains mindful of preserving the soul of the winery. Each vine pruned and bottle filled tells a story of passion, persistence, and purpose. He dreams about further refining his wines, creating more opportunities for local employment, and solidifying Singing Water as a treasured landmark of the Texas Hill Country.
He also envisions expanding the vineyard’s outreach by hosting community events, enhancing local tourism, and offering educational opportunities in viticulture and entrepreneurship. Andy believes strongly in empowering others through knowledge and practical experience, hoping to inspire future generations of local leaders and entrepreneurs. Each decision made at Singing Water is carefully weighed, reflecting Andy’s commitment to authenticity, quality, and community impact.
At its heart, Andy Ivankovich’s journey isn’t about wine or tech or titles. It’s about resilience, rootedness, and a relentless pursuit of genuine, lasting significance. Standing beneath Singing Water’s sprawling oaks, he’s exactly where he’s meant to be: rooted in the land, faith-filled, family-focused, and forever building. It’s the story of a man shaped by struggle, strengthened by service, and dedicated above all to leaving behind a legacy worthy of the Texas Hill Country he calls home.
From the dusty streets of Mulberry, Florida, to the rolling hills of Comfort, Texas, Andy Ivankovich’s life is a testament to grit, faith, and service. Whether he is leading a vineyard to unexpected heights, mentoring veterans as they step into business ownership, or pouring his energy into family and community, Andy’s story shows us what it means to build a legacy with both hands and a full heart. He embodies humility, strength, and a quiet determination to make the world better. That is why Andy Ivankovich is The Kendall Gentleman.
