Every Startup Is Lying to You, So Here's How to Pick the Right One w/ Glenn Rachlin
The Crew PodcastShow Notes
Glenn Rachlin is the VP of Worldwide Sales at Blockaid, a cybersecurity company protecting the blockchain and crypto ecosystem from malicious attacks. Before Blockaid, Glenn was an early sales hire at Alchemy, the infrastructure layer for crypto, where he helped grow the company from a $500M valuation to $10B and scaled the team from 10 to 130. Prior to his startup chapter, Glenn spent years at AWS during its era of dominance, where he experienced the wild "horse trading" culture of swapping accounts and reps between territories. He cut his teeth earlier at EMC (the classic 1980s sales org with Wolf of Wall Street energy) and IBM (old school, multi-generational, consulting DNA). Glenn is a Long Island native, a Bitcoin maxi who dollar-cost-averages into the ETF, a student of the Hunters and Unicorns podcast lineage, and a member of the Cyber Startups Network VC group.
Timestamps (00:00) Intro (01:03) Glenn's Background: IBM → EMC → AWS → Alchemy → Blockaid (02:20) Why He Left AWS After Years at the World's Hottest Company (03:47) Cold-Calling CROs From Podcasts and Forcing Them to Be His Advisors (05:03) Getting Rejected by AWS Twice: The Loop Interview and What It Takes (06:53) Why Big-Company Reps Struggle at Startups (The Two-Sale Problem) (08:06) The "Order Taker" Debate: When Easy Mode Is Actually the Smart Move (09:58) Horse Trading at AWS: Swapping Accounts and Reps Like Sports Trades (12:07) Sales Orgs Glenn Admires Most: Scale AI, Wiz, Datadog, Snowflake (18:09) How to Choose the Right Startup: Founder Pedigree and Backchannel Everything (19:49) Every Startup Is a Complete Shit Show (And That's the Point) (25:28) Assessing Market Pull Before You Join (28:59) The Chainalysis Story: $100M to $8B Because of One Regulation (30:55) AI in Sales: Translating Hebrew in Slack and Vulnerability-Based Prospecting (32:35) Why Israeli Military Intelligence Breeds the Best Startup Founders (39:01) How AI Is Changing the Sales Profile and Quota Expectations (42:30) Why You Can't Hire Slow and Win(46:43) Glenn's Hot Take: If You Didn't Get the Job, You Didn't Try Hard Enough (50:15) What Doesn't Work in Sales Anymore: Remote Is Dying, Cold Calling Is Back (53:07) Bitcoin, Dollar-Cost Averaging, and Where Glenn Puts His Money (54:41) Creative Ways to Get in Front of Anyone (Without Being Weird)
About The Crew PodcastThe Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew (an advisory, recruiting, investing, & media firm for seed through series C AI-natives) sits down with GTM operators from the fastest-growing AI natives and SaaS companies to break down what's actually working in go-to-market today. No fluff, no theory - just honest, tactical insights from people in the trenches building the next generation of AI breakouts.
About CrewCrew is an advisory, recruiting, investing, & media firm for seed through series C AI-natives & fast-growing SaaS startups.
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