GTM 31: The Venture Deal that Crumbled into Pieces

GTM 31: The Venture Deal that Crumbled into Pieces with Tyler Short

Tyler Short joins us this week as we dive into all things Go-To-Market, but this time with a Venture spin on things. We get a deeper glimpse into what’s going on across the VC world and the implications of today’s market for founders & investors. Tyler currently works as the General Counsel and Director of Operations at SixThirty Ventures.

Tyler peels the onion on one of his biggest career learnings to date – a venture deal that crumbled apart. Not one to miss!

What You Will Learn:

  • Things to look out for as someone investing in startups today.
  • How to fundraise smarter.
  • The fundamentals to help you better navigate which startups to invest in.
  • Legal necessities to be aware of as a founder.
  • Knowing when to walk away from a deal.


(3:26) VC terminology & how to break into venture.

(6:28) Predictions and themes in today’s Market.

(14:15) A deal that fell apart and what Tyler learned throughout the process.

(30:36) Best advice to founders struggling to raise in this market.

(33:27) Advice to founders around legal work.

(35:42) Tyler’s view on AI legal tech.

(38:15) What the best founders do to move the needle.

Guest Speaker Links:

Host Speaker Links:

The GTM Podcast
Don’t miss The GTM Podcast dropping every Tuesday discussing true stories and experiences including trials and tribulations in the Go-To-Market world.

Before helping found GTMfund, Scott spent 4 years at Outreach as Director of Strategic Engagement. He was in charge of aligning key relationships with VCs, BoDs, ecosystem partners and community members to drive revenue and strategic initiatives across Outreach. Scott initially ran revenue/partnerships for Sales Hacker (which was acquired by Outreach in 2018). Prior to Sales Hacker, he led and built outbound Business Development teams at Payfirma and MediaValet. Scott also advises for a number of high growth start-ups and is the host/author of The GTM Podcast and The GTM Newsletter. At GTMfund, Scott leads all fundraising efforts and runs the media arm of the firm. He’s also responsible for assessing investments, team management, LP/community relationships and GTM support for founders.

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