DtSR Episode 720 - Finance Masterclass for Cyber (Part 1)

Show notes

TL;DR: This week's pod features a Masterclass on finance for Cyber folks, led by Patrick Dennis, where we ask all kinds of questions and go from idea to the pre-growth stage of a company. What's next? Check out part 2 coming next.

Guest: Patrick Dennis

Description

A splashy funding announcement can feel like proof you’re winning, but it can also be the moment the clock gets louder. We sit down with returning guest Patrick Dennis, a multi-time [cybersecurity] CEO and operator who “swims in these waters,” to translate the funding ecosystem into plain English and remove the mystique from venture money without dumbing it down. If you’ve ever wondered why a Series D gets celebrated, what that really signals, and what it costs later, this conversation is for you.

We walk step-by-step through the early-to-late funding path: angel investors and seed rounds, venture capital at Series A and B, growth equity, and how private equity can show up as companies scale. Along the way, we tackle the words people throw around at conferences as if they’re obvious: valuation, dilution, burn rate, cap table, down rounds, and liquidity. Patrick breaks down why valuation is largely “on paper” until an exit, why investor timelines often point to a three-to-seven-year window, and why the higher you push the price, the smaller your list of realistic buyers becomes. We also talk about the “markup” incentive system that can quietly trap teams into needing a bigger round or a bigger exit than the market will support.

Then we bring it back to operating reality: how the zero-interest-rate [ZIRP] era trained cybersecurity companies to spend aggressively, and what changes when money is no longer cheap. We close with the human part founders underestimate most: taking money means giving up control and choosing a partner, and “hands-off” becomes “hands-on” fast when performance slips. Subscribe for part two, share this with a founder or operator in your circle, and leave a review with the funding question you want answered next.

YouTube video: https://youtube.com/live/zbDNnbHKEaU

Have something to say? Let's hear it.

Support the show

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YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq
LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/
X/Twitter: https://twitter.com/dtsr_podcast

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DtSR Episode 719 - Budget Season for CISOs

TL;DR: This week's pod features a Masterclass on finance for Cyber folks, led by Patrick Dennis, where we ask all kinds of questions and go from idea to the pre-growth stage of a company. What's next? Check out part 2 coming next. Guest: Patrick Dennis Description A splashy funding announcement can feel like proof you’re winning, but it can also be the moment the clock gets louder. We sit down with returning guest Patrick Dennis, a multi-time [cybersecurity] CEO and operator who “swims in these waters,” to translate the funding ecosystem into plain English and remove the mystique from venture money without dumbing it down. If you’ve ever wondered why a Series D gets celebrated, what that really signals, and what it costs later, this conversation is for you. We walk step-by-step through the early-to-late funding path: angel investors and seed rounds, venture capital at Series A and B, growth equity, and how private equity can show up as companies scale. Along the way, we tackle the words people throw around at conferences as if they’re obvious: valuation, dilution, burn rate, cap table, down rounds, and liquidity. Patrick breaks down why valuation is largely “on paper” until an exit, why investor timelines often point to a three-to-seven-year window, and why the higher you push the price, the smaller your list of realistic buyers becomes. We also talk about the “markup” incentive system that can quietly trap teams into needing a bigger round or a bigger exit than the market will support. Then we bring it back to operating reality: how the zero-interest-rate [ZIRP] era trained cybersecurity companies to spend aggressively, and what changes when money is no longer cheap. We close with the human part founders underestimate most: taking money means giving up control and choosing a partner, and “hands-off” becomes “hands-on” fast when performance slips. Subscribe for part two, share this with a founder or operator in your circle, and leave a review with the funding question you want answered next. YouTube video: https://youtube.com/live/zbDNnbHKEaU Have something to say? Let's hear it. Support the show >>> Please consider clicking the link above to support the show! -=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-=-= YouTube home: https://youtube.com/playlist?list=PLyo0dkKRvfVtWXjRxNISrhme1MgBj3C2U&si=scHDiTuLXSEQ9qHq LinkedIn Page: https://www.linkedin.com/company/down-the-security-rabbithole-podcast/ X/Twitter: https://twitter.com/dtsr_podcast