Ep. 52 | Reinventing Search for the AI Era Part II - Jeff Bobby
Reinventing Search for the AI Era Part II — Jeff Bobby
This week on Shakin’ Hands, host Jack Moran continues our exploration of AI, reinvention, and startup storytelling with a follow-up to last week’s episode featuring Michael Novielli. In Part II, we meet Michael’s co-founder at SwiftSift, Jeff Bobby, whose path into tech is anything but typical. This isn’t your average startup origin story. Here we go:
"I think everybody is always a little confused on what I actually do in life."
Jeff doesn’t try to hide the chaos that shaped his entrepreneurial career. He’s been a bartender, a soldier, a medical sales guy, and a nightlife manager. For years, he was driven by a feeling more than a goal, that there had to be something worth sticking to. That instinct, though messy, would eventually lead him straight into a chance meeting that changed everything.
A birthday dinner. A bar. A spark that refused to die.
It wasn’t a pitch deck or a product demo. It was Cinco de Mayo, some friends, and a bar in Charleston. That’s when Jeff first met Michael Novielli.
“We started with a concierge service called Charleston Fat D Club,” Jeff laughs. “And then we pivoted. Fast.”
That pivot didn’t just launch SwiftSift; it forced Jeff to confront what he really wanted to build. Jeff was born into a legacy. His father, a self-made entrepreneur, had quietly prepared his son to take over the family business. But Jeff felt the disconnect early.
"I told my dad to sell the company. I was done pretending I wanted it."
Letting go of what was safe opened the door to something that finally made sense. It wasn’t just a new path. It was a new identity.
Mentorship isn’t just part of Jeff’s journey. It defines it.
Jeff credits his growth to his mentors, people who’ve lived to the fullest, not just succeeded in the traditional sense. “I look for people with both personal and professional success. I want to learn about business and about life,” he says. That same standard shapes how he thinks about SwiftSift. Search, he believes, shouldn’t just give you answers. It should give you perspective.
"If everything else is chaotic, you’re going to be chaotic."
Jeff let his ADHD get in the way of his progress for years, until he took accountability and figured out how to use it to his benefit. Now, Jeff has built a new relationship with focus, through morning routines, stillness, and structure. Not to suppress his energy, but to guide it.
Search engines filter noise. So should we.
Jeff doesn’t write code. He writes clarity.
Jeff’s not the one building algorithms. He’s the one making sure they land. His work touches UI, product feel, and emotional trust. If Michael represents SwiftSift’s architecture, Jeff represents its voice.
And the voice has to feel human.
In Reinventing Search for the AI Era Part II, Jeff Bobby unpacks what it really means to pivot. This is a story of attention, reinvention, and stepping into a role no one else could have defined for him. For anyone wondering whether they’re too late, too scattered, or too far off track, this one is for you.
At Shakin’ Hands, we provide a platform for entrepreneurs and thought leaders to share their stories, helping others escape the rat race and chase their own dreams.
Listen to the full episode here.
Have a guest in mind or a question you want answered? We’d love to hear from you.
