Events

Where you’ll find us.

Name: The $300K Mistake Most Founders Make
Start: 2026-10-06T16:30:00Z
End: 2026-10-06T17:00:00Z

Conferences, private dinners, and the occasional detour. If we’re in your city, come say hello — the best conversations rarely happen on stage.

Book 15 minutes Meet us there

On the calendar

Featured Monday, October 6 · 9:30am PT · 30 min Live webinar · Online

The $300K Mistake Most Founders Make

The $300K mistake? Hiring an in-house security team before you actually need one. In 30 minutes we'll show you how to turn security from a blocker into a competitive advantage: when to hire, when to rent, and how to time it so you scale faster instead of overspending or stalling deals.

You'll leave with

A clear framework for the hire-vs-rent decision
Real case studies where the right call turned into millions in growth
A live Q&A to map it to your own business

Hosted by YSecurity co-founders Jon McLachlan and Sasha Sinkevich

Save your seat

Field notes — where we’ve been

Field notes — 005

Black Hat USA 2026

Mandalay Bay, Las Vegas · August 1–6, 2026

Six days in the desert with twenty thousand of the industry’s most careful people. We walked the floor, hosted a few dinners far from the noise, and talked AI pentesting until the small hours. The photos tell it better than we do.

Two YSecurity engineers crossing a Las Vegas casino floor in team shirts reading “My SOC is faster” and “Compliance beast: defeated” — 01Day zero. The shirts handled the introductions.

Black Hat “You are here” poster inside the Mandalay Bay convention center — 02Hard to argue with the signage.

6days on the ground

20kbadges in the building

5dinners off the record

0slide decks

The YSecurity team and friends at dinner under a chandelier in Las Vegas — 03Dinner three. The table kept growing.

The crowd heading into the South Convention Center at Black Hat USA 2026 — 04South Convention Center, 9 a.m. sharp.

Three of the team smiling over dinner and cocktails — 05Off the record, over appetizers.

Two colleagues at a Las Vegas dinner, one flashing a peace sign — 06Old friends, new war stories.

Two team members talking over coffee away from the conference floor — 07Off the Strip, in search of better espresso.

Team selfie at the Welcome to Fabulous Las Vegas sign — 08Obligatory. Zero regrets.

Field notes — 004

Gartner Security & Risk Summit

National Harbor, Washington DC · June 2025 & June 2026

Where the CISOs bring their budgets and their skepticism. Two Junes at National Harbor now — the YSecurity booth in 2025, the Cyberbase stand this year — telling the same story both times: embedded security teams, receipts included.

Booth sign reading “Robust Intelligence closed a $400M Cisco deal after YSecurity ran SOC 2” — 01The sign did the selling.

A YSecurity team member working at the booth podium on the Gartner expo floor — 02Booth duty, National Harbor.

Two attendees laughing together on the summit expo floor — 03Mid-floor, mid-laugh.

Two people in conversation at a table on the expo floor — 04The good conversations happen sitting down.

Two team members at the YSecurity.io booth wall — 05Embedded security team, physically embedded.

The expo floor at five o’clock, drinks cart out and crowds loosening up — 06Five p.m., when the expo floor exhales.

Two team members at the Cyberbase booth at Gartner SRM 2026 — 07Year two, new colors.

Field notes — 003

MicroConf US 2026

The Nines, Portland · April 12–14, 2026

A different crowd — founders, bootstrappers, people who ship. We sponsored the Portland edition because startups deserve real security help long before the enterprise vendors learn their names.

Ballroom screen reading “Thank you to our sponsor — YSecurity” — 01Our name in lights. Briefly.

Three of the team beside the MicroConf sponsor board listing YSecurity — 02Sponsors, mildly jet-lagged.

Four attendees talking in the hotel lobby between sessions — 03The lobby track outperforms the main track.

A group of founders out on a Portland street at night — 04Portland after hours, founders in tow.

Three attendees in front of the YSecurity “Compliance is a beast” banner — 05The beast banner travels well.

T-shirt table under the ballroom chandelier before doors — 06Swag logistics: handled.

Field notes — 002

BSides, coast to coast

San Francisco · Oklahoma · Las Vegas · Salt Lake City · Nashville · 2025–2026

The community circuit: five cities and counting. Volunteer-run, badge-optional, and closer to the ground than any keynote stage — our kind of rooms.

The YSecurity booth at BSidesSF — two banners, one table, swag ready — 01The whole kit, assembled before coffee.

Two team members at the Cyberbase banners at BSidesOK in Tulsa — 02Tulsa. New city, same mission.

Three of the team wearing BSidesSF badge medals — 03Hardware, earned honestly.

Two team members pointing at the slain compliance-beast mural — 04Compliance beast: located.

The BSidesSF expo floor at full capacity — 05San Francisco, doors open.

Selfie from the session room at BSidesOK — 06Front row was taken.

Field notes — 001

DEF CON 33

Las Vegas Convention Center · August 7–10, 2025

No booth, no scanner, no agenda. DEF CON the way it’s meant to be done — villages, hallway tracks, and the AI Cyber Challenge finals as professional homework.

Selfie in front of the giant DEF CON 33 pixel-art wall — 01The wall insisted on a selfie.

Three friends outside the Las Vegas Convention Center — 02The August regulars.

Two attendees between villages at DEF CON — 03Between villages.

The AI Cyber Challenge finals stage at DEF CON 33 — 04AI Cyber Challenge finals — professional homework.

The Car Hacking Village with laptops open around a car — 05Car Hacking Village, where warranties go to die.

Overhead view of a packed session floor at DEF CON 33 — 06Sunday afternoon, still standing.

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The best conversations never needed a badge. Fifteen minutes, no deck — just answers.

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