GHP #90 - VC #12 - Empowering the Next Generational Founders with Amanda "Robby" Robson!

The Generation Hustle Podcast

Episode 90 is with Amanda Robson, Partner at Cowboy Ventures!

Originally from Ancaster, Ontario, Amanda, better known as Robby, invests in B2B seed & pre-seed founders and focuses on innovations in developer tooling, data management, security, applied AI, and supply chain.

In November 2020, she led a US$3.2-million investment round in a securities-software company called Drata, now worth US$1 billion.

When she’s not crushing it as a newly minted and youngest partner at Cowboy Ventures, she’s running her organization, Modern Angels, which seeks to democratize funding for women and non-binary people. She also co-hosts her own podcast, The Open Source Startup Podcast.

Cowboy Ventures is a seed-stage focused fund investing in digital startups that seeks to back exceptional founders who are building products that re-imagine work and personal life in large and growing markets.

We sit down to speak with Robby about her career journey from Ontario to Silicon Valley. She details the tech landscape across North America, the importance of DEI, why she’s big on Open Source, the art of cold outreach, and much more.

Cowboy Ventures
https://www.cowboy.vc/index

Timestamps
2:45 - Intro
5:24 - Importance of Cold Outreach
9:57 - Tech Industry - Canada vs. USA
12:32 - Amanda “Robby” Robson
15:59 - Joining Cowboy Ventures
18:25 - Cowboy Ventures Investment Thesis
25:17 - What Makes a Successful Founder
28:00 - Common Hiring Mistakes Founders Make
29:40 - Importance of Diverse Teams
32:50 - What is Open Source? Why is it important?
41:50 - The Open Source Podcast
47:20 - Modern Angels
51:24 - Time Management
55:40 - Lightning Round