When I became a 37-year-old intern at Synacor—with a pregnant wife and grad school commitments—I felt ridiculous. Who starts their product management career as an intern pushing 40?
Turns out, I was in pretty good company. Internships have launched some of the most successful careers in history, and age is just a number (a number that made HR do a double-take when processing my paperwork, but still).
The Famous Interns Hall of Fame
Oprah Winfrey started as a radio intern at WVOL in Nashville while still in high school. She was so good they made her a part-time news anchor. You know, as you do when you're destined to become a media mogul.
Steven Spielberg famously snuck onto the Universal Studios lot, found an empty office, and basically interned himself into the film industry. (Note: This strategy is considerably harder in the age of keycard access and security cameras. Please don't try this.)
Anderson Cooper interned at the CIA between his junior and senior years at Yale. He now interrogates politicians on TV instead of for national security, which is basically the same thing with better lighting. OK it helps being a Vanderbilt but still, takes chutzpah.
Brian Moynihan, current CEO of Bank of America, started as a law firm intern. He's now responsible for trillions of dollars, which proves that internships can lead anywhere—even to jobs where you have to care about things like "liquidity ratios" and "stress tests."
Monica Lewinsky was a White House intern who... her internship was memorable and she's since become a successful anti-bullying advocate and public speaker.
Jimmy Fallon interned at Saturday Night Live and eventually became the host of The Tonight Show. The lesson: bring enthusiasm, make people laugh, and someday you too can interview celebrities while playing ridiculous games.
And yes, a 37-year-old freelance developer ex-CEO/entrepreneur and analyst at a hedge fund became a product management intern at Synacor and learned everything about A/B testing, exit modals, and why video ads print money. I'm including myself on this list because it's my site and I make the rules.
The Best Advice for Interns (From People Who'd Know)
"Treat Every Day Like Your First Day"
This wisdom comes from a powerful source: The Notorious B.I.G. (Biggie Smalls). He spoke to MTV about maintaining the hunger and hustle that got you in the door, even after you've made it.
On the Jay-Z song "My 1st Song" that same advice is used in a sample:
Well, I'ma s—try to stay above water, you know? Just stay busy, stay working Puff told me, like, "The key to this joint— The key to staying on top of things Is treat everything like it's your first project, know what I'm saying? Like it's your first day, like, while—when you was an intern Like, that's how you try to treat things—like, just stay hungry"
I swear you can learn more about business from hip hop than any book but I'll save that controversial take for my own book.
If we rewrote that as 'rules for interning' we could say it means:
- Paying attention to everything
- Asking questions without shame
- Making no assumptions
- Trying to understand how things work
- Grateful for the opportunity
- Eager to prove yourself
If you can maintain that mindset—the curiosity, the humility, the hunger—throughout your internship (and your career), you're going to learn more than the person who gets comfortable after week two.
"Ask Questions, But Do Your Homework First"
The best question framework I learned:
- Try to figure it out yourself first (Google, documentation, company wiki)
- Form a hypothesis about the answer
- Then ask: "I'm trying to understand X. I think it might be Y because of Z. Is that right?"
This shows you:
- Respect others' time by doing research first
- Are thinking critically, not just asking people to think for you
- Actually want to learn, not just get an answer
Compare:
- Bad: "How does our ad serving work?"
- Good: "I've been reading about our ad serving, and it looks like we use header bidding with a waterfall fallback. Is that still accurate, or has the system evolved?"
The second version makes people want to help you.
"Your Internship Is a Months-Long Job Interview"
The conversion rate from intern to full-time employee is surprisingly high at good companies. Why? Because by the end of an internship, both sides know if it's a good fit.
Companies get to evaluate you doing actual work, not just interviewing well. You get to evaluate the company culture, the work, and the team, not just the recruiting pitch.
Treat your internship like an extended audition where you're both the performer and the audience. Are they impressing you? Are you impressing them?
At Synacor, I knew within a month that I wanted to convert to full-time. The work was challenging, the team was smart, and I was learning a lot. (They kept me. Good decision on their part, obviously.)
"Take Notes Like You'll Forget Everything Tomorrow"
I filled multiple notebooks during my Synacor internship. I think it is well established that writing leads to greater retention than typing as it activates more of the brain during the act of creation. Call me old school, note my advanced age for interning, but I encourage people to write with pen and paper or at least stylus and digital notebook or tablet.
"Volunteer for the Work Nobody Wants"
The unglamorous stuff like writing documentation, organizing files, cleaning up old Jira tickets, testing edge cases, smoke testing UAT and then Prod after a release is often the most valuable for learning how things actually work. As an intern or noob you actually have the time that fully employed people do not, so you can take on projects that others cannot.
"Figure out how the company makes money and do that thing"
In the case of Synacor, understanding more about digital ads and how it related to the product design was the whole game. But there were some niche areas that were sort of ignored but were little ATM machines. The weather page was frequently visited and decidedly unsexy. The finance page was dry graphs and tables but had crazy time-on-site and people that used it to track their portfolios were all relative super users. The comics section was regularly scoring high with popularity and time on site. Working on those sections was unsexy but they were also areas where there were a lot of low hanging fruit as they were neglected.
The 37-Year-Old Intern Advantage
Being an older intern had some unexpected benefits:
People took me seriously faster. Fair or not, gray hair buys credibility. When I asked questions or made suggestions, people assumed I had context, not that I was just a kid with ideas. I had gravitas. I was also mega sleep deprived and looked 10 years older than I was (my first child did not like going to sleep).
I had no ego about the title. 22-year-old me might have been embarrassed to be "just an intern." 37-year-old didn't care what people thought as much. I was too focused on grad school and an infant to worry about the 25 year old junior developer that loudly, repeatedly made fun of me for being an old intern. I was fortunate to be financially secure which helped a lot with my not caring much what people thought.
Life experience translated. Years of client management, project juggling, and freelance hustle made me scrappy. Nothing like needing to close deals while sweating making payroll to build a thick skin and give perspective on what makes a business hum.
I knew how to ask for what I needed. Younger me would have struggled in silence. Older me knew to say: "I need help understanding this" or "Can you point me to resources on that?" Its about having the confidence to look like an idiot and, sometimes, to get treated like an idiot, and still know inside that you are in fact not an idiot. Everyone is new at least once. Just ask Ira Glass.
Which brings us back to Biggie's advice: treat every day like your first day.
You're An Intern, Not "Just An Intern"
The word "intern" somehow carries connotations of coffee runs, grunt work, and not being taken seriously. There's some truth to that.
So treat every day like your first day. Ask questions. Do work that matters. Take notes. Be useful. And remember: nobody starts at the top.
Even Biggie started on the corner. He just made sure to hustle like it was day one, every day.
Started your career as an intern? Still an intern? Got advice for aspiring interns? Let me know—I'm always collecting wisdom from people who've been in the arena.