Great careers are made with good people, and better questions.
This week I spoke with Brian Breslin, 2004 UVA grad who’s now the Director of Student Entrepreneurship at UVA and CEO & Founder of Infinimedia Inc
The Rundown:
COLD OPEN: 16 year old entrepreneur, bad job offers, word of mouth
TURNING POINT: Cash flow struggles, 2008 financial crisis, adapting business models, laying down the law
STEAL THIS: If you want to be interesting, be interested in other people
INDUSTRY INSIDER: Short term needs vs long term potential
IF I WERE YOU: A lot of people are passengers in their life. Be a driver
COLD OPEN
How Did You Get Your Start?
My first business started in high school, building websites for my parents' friends' businesses.
I was building a bunch of websites, hiring people to write content, and selling ads on mine as well as other people’s websites. I had an itch to scratch and wasn’t smart enough to think “maybe a 16-year-old should be doing other things.” But, I had bills to pay.
Fast forward, I’m at UVA, and I shut down the businesses because I was busy with school. There wasn't a hospitable environment for entrepreneurship back then at UVA, so it was a lot of solo tinkering until I realized this was what I really liked doing.
I graduated, headed back to Miami, and the job offers sucked. One paid 26K / yr in NYC. They suggested I live with my parents to save money and I was like “my parents are 3,000 miles away.”
So I went back to what I knew: building websites for small businesses.
A few of my friends and mutual family members were using excel or paper to run their companies, and I saw an opportunity. I built super simple web-based software, and I’d ask my customers "Do you know anyone who needs this?” I got new clients through referrals and word of mouth.
That business ended up supporting me for 15+ years, and I didn’t have to get a “real job” until my mid 30s.
Even though I was building startups, I didn’t have any formal business education, so I got an MBA from Northwestern.
For so long, I’d been mentoring others. It led me to working at UMiami, after my MBA, where I was mentoring hundreds of entrepreneurs. I did that for 7 years, and then UVA, which was looking to expand their entrepreneurship program, reached out.
I’ve been the Director of Student Entrepreneurship here at UVA since 2024.
PRESENTED BY THE FOUNDRY
When I first thought of Hoo You Know, The Foundry — UVA’s free startup space above Coupes — helped me figure out what to do next.
They offer advising from seasoned founders, resources, and mentorship whether you have a 3 a.m. idea or are scaling a business. They helped get me started — and they can help you too.
Got a startup idea? Book A 30-Minute Advising Meeting
TURNING POINT
What’s A Challenge You Faced Early On?
A recurring challenge was cash flow. Having enough for payroll.
Nothing sucks more than sitting there at your desk at midnight saying “how am I going to pay all my staff” in a week if we don't close this deal.
In 2008, during the financial crisis, a third of my clients canceled our projects.
We had to adapt, updating our business model to be less dependent on individual projects and more on retainer deals. We also increased our margins so we could save more to weather a storm.
That was pre my MBA, so I didn't have anyone telling me “make sure you have 6 months of runway at all times because you never know.
We were very lax with our customers on payment timelines. It wasn't until we started penalizing them (like we said we would in the contracts: threatening to sue or pull servers), that we were taken seriously.
The takeaway is to build in buffers for any of your assumptions, because you don’t know which ones will be right or wrong along the way.
STEAL THIS
What’s A Question You Love To Be Asked (Or Asking)?
We’ve been hiring people to work at The Foundry, and one question people ask is "What's a good trait for someone as a venture analyst?”
The repeated thing that keeps coming to mind is demonstrating curiosity.
If you want to be someone who’s interesting, be interested in other people.
One of my favorite podcast questions is "What's something you thought you knew but you later found out you were wrong about?” That one’s good too.
INDUSTRY INSIDER
What Do People Misunderstand About Entrepreneurship?
People think it's like the movies, all glamour. The reality is for most 21-22 year old fresh grads, you’ll probably make more money at a regular standard job in the first few years, then they would as an entrepreneur.
If you need money now, maybe this isn't the path since it's high risk. On the flip side, if you look at long term career earnings, you could make a lot more as an entrepreneur.
It also might not just be about money. Maybe it’s control and agency. For me, I didn’t like sitting at a desk waiting for someone to tell me what to do.
Lastly, being an entrepreneur is a point of privilege. At UMiami, I had a lot of students who were pushing 2K / month student debt payments immediately after graduation. That's a lot to be saddled with, and it impacts what jobs you can take.
You might love opera, but there's no opera job that's going to pay you enough to cover that 2K / month nut.
IF I WERE YOU
Do You Have Any Advice For Students?
Don't be afraid to be intellectually curious.
It's easy to slump into the couch and be stagnant. Reality is, jobs are changing so fast, if you're not constantly reinventing yourself over the next 10-20 years, you're going to be left behind and get stuck in menial jobs or jobless.
Being intentional and driven with what you're doing will put you ahead of a lot of the competition.
A lot of people are passengers in their life. Be a driver.
And use less social media. It’s all brain rot.
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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