This week I spoke with Ben Weinberg, 2018 UVA grad who’s now a Co-Founder of the Ember Fellowship.
The Rundown:
COLD OPEN: Consulting blues, moving to Birmingham, farming pivot, startup fellowships
TURNING POINT: Principles over profit, leaving a startup
STEAL THIS: What do you fall back on when making decisions?
INDUSTRY INSIDER: Emerging markets vs big cities, opportunities, work-life balance, solving real problems
IF I WERE YOU: Find your principles and stick by them
COLD OPEN
How Did You Get Your Start?
I was always interested in business, math, and science. I figured I could always learn business on the job, but if I didn’t study math and science, I’d lose those skills. So I decided on the E-School rather than Comm.
I studied systems engineering. Most system engineers at UVA applied for consulting jobs, so I did the same. It drained me. The case studies and interviews weren’t giving me any energy.
I found a program called Venture for America, which connected college grads with high-access, high-impact roles at fast-paced startups in emerging cities.
I applied, never again having to market size the number of people in NYC or how many quarters stacked in a room.
I got into the program and moved to Birmingham, AL, and the experience changed my life.
I joined the product management team at a company called Fleetio. We raised a series A, B, and C. I launched the first revenue-generating add-on product, which made a quarter million in revenue in its first year.
I wanted to push myself, so I left Fleetio to start my own mental health app called Encircle. Even though our product wasn't successful, it gave me the professional confidence to keep following my interests.
I had volunteered at a lot of farms, and was interested in diving deeper into the agriculture industry. I networked with farmers, friends of friends, trying to find people who were doing cool stuff in the space.

I joined a nonprofit that was helping the U.S Department of Agriculture think about how they can collect and use data more effectively. After 2 years, our government grant dried up, which was a blessing in disguise.
It felt like being deep in a complex system where my voice was buried under a lot of bureaucracy. At a startup, you build something and iterate. With the nonprofit, it was a much slower cycle.
I still do some work in agriculture, but it’s more startup-adjacent.
Currently, I work at the Ember Fellowship. It's an organization I founded as a way to revitalize Venture for America, which shut down in late 2024.
PRESENTED BY THE EMBER FELLOWSHIP
The Ember Fellowship connects recent grads with vetted startup roles in Birmingham, Atlanta, and Detroit. Fellows get hands-on training in startup fundamentals and AI, plus access to a 1,600+ alumni network.
They’re having an info session at 9 Elliewood Ave on Tuesday, December 2nd at UVA. Sign up here.
And if you want a coffee chat with Ben, a co-founder of The Ember Fellowship, click here.
TURNING POINT
What’s A Challenge You Faced Early On?
When I was at Fleetio, I loved my team. The work was interesting and I was comfortable.
If my focus was maximising income, I probably would’ve stayed. But I had to return to my guiding principles, which was asking myself “where can I learn and grow as much as possible?”
The answer to that question led me to leave Fleetio and start my own company.
The challenging part wasn't actually leaving. It was figuring out the right question to ask.
I was 26, and knew I wanted to start a family in my late 20s. I wouldn’t have the same financial freedom later in life, so I felt this was my opportunity to try something new.
STEAL THIS
What’s A Question You Love To Be Asked (Or Asking)?
I like to ask people “What are your principles?”
What are the set of rules you live by when making decisions?
INDUSTRY INSIDER
What Do People Misunderstand About Working In Emerging Markets?
Emerging markets are cities outside of New York and San Francisco. Cities like Birmingham, Detroit, and Atlanta.
The misconceptions are that they’re boring, there isn't much going on, and there aren’t as many opportunities to grow. I’d say all of those are wrong.
In New York, there are a thousand great Thai restaurants. In a smaller city, there’s one. But because of that, you get to know the owner and they remember your name.
If a founder is choosing a smaller city, they’re doing it because there’s a real problem to be solved. You’re not chasing the startup hype wave in Birmingham. I’m not sure the same holds for New York or San Francisco.
These founders likely have family in these cities. They’re looking to be home well before 10pm, so they’re more intentional with their work. They’re more efficient with allocating capital, have a better runway, and create a more stable work environment for recent grads.
When you work in an emerging market, you stand out. You’re a big fish in a small pond. It’s easier to network because people are excited you’re in their city, be it investors, founders, or anyone you want to talk to.
IF I WERE YOU
Do You Have Any Advice For Students?
Find the question you can ask yourself to make sure you're on the right path, using the principles that matter most to you to find it.
For me, it was “where can I learn and grow as much as possible?” Others, it may be “where can I make the most money?” or “what’s the most prestigious path?”
I don’t judge what that question is, but it’s important to know yourself and figure it out.
There’s a great book called Principles by Ray Dalio, who's an incredibly successful hedge fund manager and entrepreneur. He’s written down a set of decision-making frameworks he uses in any investment or personal decision.
I actually don't like a lot of his principles, but that's not the point. The point is you should write down how you think about the world, so when you’re faced with a challenge, you can return to your framework.
For example, my principles are complexity, pragmatism, ordered chaos, accountability, transparency, and balance.
CLOSING TIME
What To Do Next
Reading is great — but putting yourself out there, meeting new people, and finding opportunities is what this is all about.
4 things to do right now:
Find a UVA alum and send them a cold message.
Follow up in a week if they don’t respond.
Prepare for the meeting, and talk to them
Explore a new industry:
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