Every Startup Is Lying to You, So Here's How to Pick the Right One w/ Glenn Rachlin, VP of Worldwide GTM @ Blockaid

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, and a member of the Cyber Startups Network VC group.

When AWS got really big, territories became so bloated that accounts were openly traded between AEs. Sometimes for other accounts. Sometimes across territories. Sometimes for people.

"You would trade accounts for other accounts, you would trade accounts between territories. And then sometimes you would trade accounts for people. It was kind of like sports."

Higher-level reps had industry expertise that was effectively a commodity. "Give me this rep, and I'll give you some of these accounts." The AEs themselves often didn't know it was happening above them. A unique look at what scale actually does to sales orgs that is talked about less commonly.

Glenn's take: it's the smarter decision to join the order taker company. You skip the hardest part of sales (proving the category exists), you still learn how to build champions, negotiate, and close, and you learn what "good" looks like inside a real startup machine.

But the reward is exponentially bigger if you join pre-PMF and the wave breaks.

His example: Chainalysis sat at a $100M valuation for years selling an anti-money-laundering product nobody wanted. Then a regulation hit. Suddenly everyone had to have it. Valuation jumped to $8B. The reps who were there before the chasm got crossed got life-changing outcomes. The ones who joined after took home a normal paycheck.

It's a risk question, not a quality question. "If you want a life-changing outcome in one shot, that's where you have the guts to go and do something like that."

Glenn calls himself a back-channel guy to the point that it annoys his own founders. Talk to customers. Talk to former employees. Talk to other investors. Call their competitors. Find another AE in the space and ask why they win and why they lose.

The single most important filter is the founders. Do they always figure it out, no matter what? When you interview them, ask one question: "Why do you guys lose deals?" The answer tells you everything.

A VC-speak answer with no specifics is a red flag. A founder who says "we just lost a deal last week, here's exactly why, and here's what we're fixing" is the one you want.

Glenn studied the Hunters and Unicorns lineage obsessively before leaving AWS: Scale AI, Snowflake, Datadog, Wiz, Mongo, Dorada. The pattern across all of them is the same set of leaders teaching the same playbook.

The surprising part: "They're not Uber geniuses. They understand people really well. And they just ask very simple, obvious questions."

The example Glenn used: in the middle of a POC, ask the prospect, "Do you think this is going to work?" If they say "I don't know, maybe not," you ask "Why not?" Purposely adding friction to qualify the deal, instead of pushing forward and hoping. Most sellers won't do it because it feels uncomfortable. The best ones lean in.

Why do so many great cyber companies come out of Israel? It's not a coincidence. Every Israeli has to do military service, and a meaningful chunk gets routed into intelligence units that breed founder behavior on purpose.

The training: get handed an impossible problem with zero direction and zero resources. One real example Glenn shared: "This bus usually stops at this bus stop at 5:43. Make sure it doesn't get there until 5:48." Go figure it out.

Five or six years of solving unsolvable problems with no guidance is exactly what running an early-stage startup feels like. That's why Wiz, Palo Alto Networks, Akamai, and dozens of others all trace back to the same handful of units.

(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)