Free. Take one.
The Chauncy Street Free Press
Circulation: 1

Local podcast wants Portnoy, will pay in pizza

Two Boston founders printed a four-page paper to book one guest. The guest invented the format.

Dave. In 2003 you wrote a four-page sports paper, sold the ads, and handed it out on T platforms yourself. Twenty-three years later we run a founder podcast around the corner from the Downtown Crossing stop, and we couldn't think of a better way to reach you than the one you came up with.

So here's our paper. Four pages, free, one reader. Page 2 is why Boston founders need your story. Page 3 is the pizza. Page 4 is where you give us a score.

2The Chauncy Street Free PressBusiness

He sold it for $551 million and bought it back for $1

That might be the best deal a Boston founder ever made. We want it told in a room full of Boston founders.

The Portnoy Line

  1. SwampscottGrew up here. Won the league batting triple crown as a junior at Swampscott High.
  2. Ann Arbor, 1999Michigan degree. Ran a betting-picks site on the side.
  3. Yankee Group, BostonMarket research desk job. Didn't take.
  4. T platforms, 2003Four pages, free. You wrote it, sold the ads and handed it out yourself.
  5. The blog, 2007The paper goes online. The readers follow.
  6. City Hall, 2013Ran for mayor of Boston. Came up short on signatures.
  7. New York, 2016Chernin buys a majority stake. Headquarters leaves town.
  8. Penn, 2020 to 202336% for $163 million, then the rest for $388 million. Six months later you buy all of it back for a dollar.
  9. Downtown CrossingNext stop: 38 Chauncy Street. One chair, two mics, one cheese pizza.

What we'd ask

  1. How do you get the first thousand readers when you're the writer, the ad guy and the delivery guy?
  2. Walk us through the dollar.
  3. Could Barstool have gotten that big without leaving Massachusetts?
  4. What does Boston get wrong about the people who build things here?
  5. A 26-year-old is about to quit a desk job downtown. What do you tell them?

Who's asking

BUILD617 is a founder-led, equity-free community for people building tech companies in Boston. Early-stage founders work out of our space at 38 Chauncy Street for free. Nobody takes a cut. The goal is three times as many breakout companies out of this city in ten years.

The pod is two founders, Nick Leonard and Nathan Spielberg, asking people who built something here how they did it. No scripts. Past guests include Helen Greiner of iRobot, Jason Kelly of Ginkgo Bioworks, Mike Salguero of ButcherBox and Eric Paley of Founder Collective.

None of them started by handing out a newspaper on a subway platform. That's the episode we don't have.

Same playbook, smaller budget

  • YouUs
  • Gave the paper away.Give the desks away.
  • Put up $500,000 of your own to start the Barstool Fund. It raised over $39 million for 348 small businesses.Equity-free. We take 0% of anything a founder builds here.
  • Wrote it, sold it and delivered it yourself.Two hosts who also run startups. We carry our own mics.
3The Chauncy Street Free PressFood

The pizza clause

One bite of a podcast. Everybody knows the rules.

There will be a plain cheese pie on the table when you sit down. You review it on camera. Then you review us. Both numbers air, even if ours is ugly.

In August you asked which Boston-area spots you haven't tried yet. There are 38 founders in our community and every one of them has an answer. Pick the shop, or let them fight it out.

Monte's is about half an hour north of us. If a 10 is what it takes, we'll leave early.

Your numbers around here
Monte'sLynn. Still the only 10.10
HalftimeCauseway Street, West End9.2
ReginaNorth End9.1
Santarpio'sEast Boston8.2
Pizza ProjectBrighton, this summer8.2
The BUILD617 pod38 Chauncy Street. Unreviewed.?

The rider

  • Cheese pizza, your shopHot when you sit down. No toppings, no arguments.
  • An hour, or lessFit it into a trip you're already making. You were here in January and again this summer.
  • Your book on the tableWe'll hold Cancel Me If You Can up to the camera ourselves.
  • No softballs, no gotchasNo handler-approved question list either. It's founders asking a founder.
  • No Big Ten deal to protectSay whatever you want about Columbus.
  • We travelCan't get to Chauncy Street? We bring the mics to you.
4The Chauncy Street Free PressSports

One home game

Boston lost the Barstool franchise to New York, then Chicago. We're not asking for the team back.

You've spent two decades being the loudest Boston fan in whatever city you're standing in. You chained yourself up in the NFL's lobby over Deflategate. You were back at the Super Bowl this year when the Patriots were.

The founders here are the same kind of stubborn about this city. They stayed when the advice was to move to San Francisco. They'd like an hour with the guy who proved you can start with nothing in Boston and end up owning the whole thing.

One home game. That's the ask.

Scouting report: D. Portnoy, guest

Hometown
Swampscott, Mass.
Bats
League triple crown, junior year.
Throws
Opinions.
Career
More than 1,000 pizzerias reviewed. One 10 awarded.
Discipline
Arrested at NFL headquarters, 2015. Tossed from a Super Bowl, 2019. Let back in, 2026. We count all three as upside.
Petitions
The 2013 mayoral run fell short on signatures. We'll collect them this time. We have 38 founders, so we're 38 in.
Projection
Best episode we've recorded.

One bite. Score the pitch.

Book the chair

Your score rides along: 7.0. This goes straight to the two hosts.

Faster: DM @build617 on X with a number between 0 and 10. Or email hello@build617.org.