I interviewed Stephanie Roulic who's currently Head of Operations @ Goldcast (series A SaaS start-up that's raised a total of 38 million) and the founder of Start-Up Boston.
In August of 2016, Stephanie co-founded a martech company, nDash, and had absolutely no idea she was doing and didn't have a network within the startup community. After discovering that most events were either too salesly or generic to be useful, Stephanie decided to create her own event that would both build a network and answer the questions she had.
About a year later, the first ever Startup Boston Week occurred. This 5-day event brought together 2500 attendees and 125 speakers, over the course of 52 events with legendary speakers like Brian Halligan (Founder & CEO, Hubspot), and Paul Liberman (Founder & COO, DraftKings) just to name a couple.
Fast-forward to 2021 and Startup Boston Week has expanded into the organization Startup Boston, an organization on a mission to showcase the New England startup ecosystem.
We talk about:
0:00-1:02: Intro
1:02-3:46: What were the early days of start-up Boston like?
3:46-6:14: Building a software company at 26 with no prior work experience
6:15-10:12: Building Start-Up Boston: Cold emailing the CEO of Hubspot, and working 14-16 hours per day
10:12-12:50: Cold Outreach Strategy
12:50-16:32:Balancing Start-Up Boston and dNash: outreach cadence
16:32-19:20: Working 16 hours per day: Maintaining Motivation
19:20-21:51: Hacking Getting Started
21:51 - End: When should you cold email your dream speaker/ podcast guest (e.g CEO of Hubspot)?
Disclaimer: Stephanie's views do not necessarily reflect those of Goldcast; she isn't appearing on this podcast in her professional capacity.