After ten years in San Francisco’s high-energy, chaos-driven startup world, Drew Chapin expected that his next chapter might be a quieter one. But when that move turned out to be to Philadelphia – a city without an obvious on-ramp into its entrepreneurial scene – he found himself facing an unexpected challenge: figuring out where to start.
“When I say I had no idea, I mean I truly had no idea. I thought I was setting myself up for remote work and train rides to Manhattan every week,” shared Chapin.
A tech marketer by training and founder by instinct, Chapin had spent the past decade helping early-stage startups take their first steps, from market testing and sales strategy to investor pitches and growth campaigns.
But in moving across the country, he found himself a stranger to a new business culture – so he started with the go-to-market basics.
“It wasn’t particularly sophisticated. I sent dozens of cold emails,” he laughs. “I figured I’d just throw myself into the mix and see who responded.”
To his surprise, plenty of people did.
He connected with faculty at Drexel and Temple who welcomed him into the classrooms of their entrepreneurship programs. He started showing up at meetups and demo nights, hopping between coworking spaces and startup happy hours.
Slowly, the shape of Philadelphia’s entrepreneurial scene began to emerge – less polished and far more fragmented than what he knew from the Bay Area, but undeniably alive.
That digging paid off.
Not long after his arrival, Chapin began working with Hustle Fund, a San Francisco venture capital firm and angel syndicate known for backing what they call “hilariously early” startups. His role? Meeting founders and attending pitch events in search of the next deal for the investment group.
As part of that effort, Chapin started producing deal memos summarizing each company: the problem, solution, market, notes on the founders, and product. And as he did that work, he had an idea: why not share these deal memos publicly?
To do so, Chapin launched The Drewsletter, a monthly email that offers a look at the startup scene in Philadelphia. It’s part dispatch, part personal essay – an ongoing record of what Chapin calls “learning and unlearning” in real time.
In the first two issues, Chapin has shared three compelling deal memos which feature startups from Philadelphia’ Center City, including the hypnotherapy app Burble (in issue #1) and college athlete recruiting platform NextPick (from issue #2). Chapin’s also riffed on startup trends, venture logic, and shared links he finds interesting.
What The Drewsletter isn’t, is formal. It’s written in a voice that’s casual and sarcastic while also offering informed insights and opinions. It reads like a note from a friend who knows what they’re talking about – and wants you to, too.
That tone permeates the whole experience, including Chapin’s own promotion of the newsletter. In one recent post, Chapin admitted that “more than 80% of email newsletters fail in their first year” as a way to convince people to give the newsletter a try.
After all, odds are that it won’t be a long-term commitment.
Two issues in, there’s no sign of stopping. And Chapin says he’s already working on the third issue, which drops the first week of July.
If you want to get a feel for what’s really happening inside Philly’s startup scene – and maybe discover a few gems before the rest of the world catches on – sign up at chapin.io.
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