Receipts by OpStart
Receipts is a podcast from OpStart about the financial side of building a startup — the part most founders only talk about in private. Each episode digs into the real numbers behind the build: burn rate, runway, R&D credits, fundraising scars, the first real CFO conversation. The decisions that worked, the ones that didn't, and what the spreadsheets actually said when things got hard. Made for founders pre-seed through Series C — the ones doing the work, not posting about it. No spin, no recycled LinkedIn wisdom. Just candid conversations with founders, operators, and the finance pros keeping the back office in o...
Scaling pickleball leagues: zero to 65 cities in 18 months
In this episode, we sit down with Tommy Flaim, founder of Silly Pickles, to unpack how he built one of the fastest-growing adult rec sports communities in the country.
Tommy shares his journey from investment banking to launching (and winding down) his first startup, and how he stumbled into building a scalable, software-powered league model that’s now live in 65+ cities.
We discuss:
• Why most adult rec leagues fail to attract young professionals
• How Silly Pickles scaled to a $3.4M run rate in 18 months
• The franchise-style operating model behind 100+ facility...
An API Key for Batteries: How Proper Voltage is Powering the Hardware Decade
Greg Slauson, CEO of Proper Voltage, joins Paul Anthony to unpack how a career that started selling structured fixed income on a Goldman Sachs trading floor led him through a solar fintech rocketship, a caramel apple business bought with an SBA loan, and ultimately to building the intelligence layer that turns batteries from a limiter into an enhancer. Greg and Paul have been friends for 12 years, since they were randomly paired as summer intern roommates in Chicago, and Proper Voltage runs its accounting and tax through OpStart, so the conversation moves easily between deep technical detail and the real...
Underwriting Space Exploration | Yuk Chi Chan, Charter Space
In this episode, we sit down with Yuk Chi from Charter Space Technologies to unpack what it takes to build the financial and underwriting infrastructure for the space industry.
Yuk shares his journey from military engineering to space law, to working inside a satellite manufacturer—where he experienced firsthand how fragmented engineering data and compliance workflows can slow missions down and make insurance painfully difficult to obtain.
We discuss:
• Why space is missing the “middle layer” of capital (insurance → debt/credit markets)
• How better data and systems engineering can improve underwriting and reduce r...
Building a Music Town: How Juke is Reviving Live Music One City at a Time
Griff Eaton, founder of Juke, joins Paul Anthony for OpStart's first in-person interview to unpack how a frustrated night at the Livery in Benton Harbor turned into a venture-backed platform now reshaping live music in cities across the country. Griff walks through the three barriers that kill the simple act of tipping a local artist (no cash, awkward walk to the stage, no idea what songs they actually play) and the PowerPoint-and-paper-printouts prototype he ran with the Justin Stoblin band to prove people would pay if those frictions disappeared.
From there the conversation moves through...
