In this episode of Fund/Build/Scale, I talked with YL Ventures Partner Andy Ellis (a former CISO) about his approach to storytelling, tactics for founder-led sales and marketing, and why he thinks the cybersecurity hiring challenge isn’t a talent shortage, but a market misunderstanding.

We also discussed refining product-market fit, customer discovery methods and pitfalls like believing in one's own narrative too strongly. The conversation also touched on hiring strategies, managing design partnerships, and maintaining humility as a founder. “The basic entry level skill of reading the room is knowing when somebody already agrees with you,” said Andy.

RUNTIME 44:15 EPISODE BREAKDOWN

(1:44) Andy describes his day-to-day work at YL Ventures with founders.

(4:08)  "It's like you now have an infant, and your only job as a parent is to create a competent adult.”

(6:33) How he prefers to be pitched.

(7:52)  ”The art of storytelling is taking a message and putting it in a narrative vehicle.”

(14:38) The biggest storytelling mistakes early-stage founders make.

(17:08) “ The basic entry level skill of reading the room is knowing when somebody already agrees with you.”

(18:50) “ Fear is a hard, hard sale… It's so transparent and CISOs do this every day.”

(19:36) Common cybersecurity GTM missteps.

(21:40)  ”The moment that you can sell the same product to two different companies, you should have a sales rep.”

(23:45) How Andy helps founders read the room when they’re trying to make a sale.

(27:20) “ You're hiring really out of a very different pool when you're in the cybersecurity space.”

(29:08) “ Stealth is sort of a misnomer, but we're still sort of stuck in it.”

(30:54) What to say if you want someone to quit their cushy job and join your risky startup.

(32:46)  Rock-star hires are “fantastic if they stumble into your lap, but you can't go look for them.”

(35:08) “ That first marketer you hire needs to be able to do a lot of things.”

(39:05) “People with massive egos have a lot of humility.”

(41:20) Trends in cybersecurity and AI he’s excited about in 2025.

LINKS

• Andy Ellis
• 1% Leadership: Master the Small, Daily Improvements that Set Great Leaders Apart
• csoandy.com
• YL Ventures
• YL Ventures’ The State of the Cyber Nation 2024 (PDF)

SUBSCRIBE TO FUND/BUILD/SCALE

• LinkedIn
• Substack
• Instagram

Thanks for listening!

– Walter.