How it Started / How it’s Going
Last week, on a British manor at the Ideas Fest one hour outside of London, I had the privilege of listening to Orbiit’s co-founder and CEO Bilyana Freye tell the story of her company from start to exit, in front of a rapt audience. It was a good reminder of the complexities, pivots, self-determination, and inspiration of founder stories.
I loved hearing her tell the success story of Orbiit’s recent acquisition by Hivebrite. But I also loved hearing the early origins of her hard work. These “full cycle” startup stories are hard to come by. But whether you’re a founder or an investor, understanding the complete journey is crucial if you plan to offer advice to someone else along the way.
Too often we don’t notice a burgeoning brand or startup or founder on the cusp of something great until they are already on the rise, and then we greet them as an overnight success. (As we all observed this summer, Chappell Roan’s smash-hit summer as a singer was actually a decade in the making.)
Typically, tech conferences bring someone up on stage during their “arrival” moment, sharing where they are now and their vision for the future. While this may leave attendees feeling inspired and energized, without understanding what the world looked like when they started and knowing what decisions come next, it's hard to find a lesson that's both meaningful and applicable to your own situation.
For example, I first got to know Bilyana in the 2020-2023 era of her business. I’ve always known Orbiit as an AI and ML-powered matching engine to connect people in peer groups. But I didn’t know until last week that her business actually started out as an in-person job shadowing program that had been gaining increasing popularity among NYC businesses. Until peak COVID hit and people stopped going to offices in person.
We spent a lot of time in her founder's story talking about tough calls that founders face at key moments. Do you call it quits, return the capital, and walk away? Or do you pivot? Ultimately they decided to pivot, leaning into a gut instinct that in a COVID-fueled world with rising isolation, virtual community-building would matter more than ever. They spent several years iterating on this refined business model, which included negotiating an entirely new set of stakeholders, and adapted as the digital community-building market matured, ultimately joining forces with Hivebrite to continue to propel this vision forward.
Unsurprisingly, at this event, everyone wanted to talk with Bilyana afterward. They had so many questions, both about her own journey, and seeking advice for their own startup beginnings.
From Start to Exit
Celebrating success is fun, but it’s a mistake to simply mimic someone else at their arrival moment and claim it as your own. The context of where they came from, and how they moved through those moments, matters more than anything.
While I’ve worked in tech for 15 years, I didn’t really internalize this idea until the three years that I spent working among so many crypto and web3 entrepreneurs. For the first time, from the incubation inception moments of hacker houses, nomadic fellowships, and conference circuits, I heard the early germination points of ideas from many founders. Months later, at the next event, I’d catch up with the same subset of people and hear snippets of the iteration. Then the tough spot. Then the pivots. The rebrands. The new co-founder coupling and the new directions. The big breaks and sometimes, the shutdowns. Notably, none of the people in the immediate founder circle who started web3 businesses in 2021 still run those exact same businesses in that exact same way in 2024. Most have pivoted twice, if not three times. But all of them are still building.
These experiences deepened my understanding of the founder journey. Success isn’t a straight line—it’s about continually evolving and adapting, even when things don’t go as planned. I realize not everyone has the stomach to spend years bouncing around web3 tech conferences around the world to pick up on these patterns. But chances are, you have access to founders who might be willing to share their “start to exit” story with you.
And even if not, I’ll do my best to keep sharing what I’ve learned along the way.
