Spies, Generals, and a 37-Degree Lake: Inside the Inaugural Whitefish Security Summit

The first dispatch from two days that proved the concept.

The inaugural Whitefish Security Summit, sponsored by Strider Technologies, Red5, Helio Risk, Ledlow Security Group, 5 Stones Intelligence, Acorn Capital Management, and Four Branches Bourbon, wrapped on Saturday, April 4th.

Nine months in the making, two name changes, three location changes — and then Whitefish. Over 130 people signed up to attend our first event and 86% have said they want to come back in 2027.

So much happened in just two days that it’s impossible to capture it all in one article, so I’ll be doing a series of highlights over the next 30 days, starting off with some images and feedback from those who attended.

Many of our attendees were Intelligence and Military veterans who took no convincing to do PT in near-freezing temps before breakfast.

A pre-dawn run through downtown Whitefish on day one

The pre-polar swim briefing by Whitefish Security Summit co-founder Eric “Olly” Oehlerich, former Commanding Officer (CO) of Naval Special Warfare Development Group- Squadron 2 (Retired)

6:30am Polar Swim on April 3, 2026

“A core lesson came from combining Stanley McChrystal’s leadership insights with our morning PT, especially the 6:30 AM swim training in a 37°F Montana lake, led by Eric Oehlerich, former U.S. Navy SEAL and Commanding Officer of DEVGRU (Squadron 2). It made one thing clear: theory means little without execution. The water is cold, whether you like it or not. The real question is whether you perform and lead when it matters.” - Cassian Peña (WSS Young Professional attendee)

Gen. Stanley McChrystal gave the keynote from Washington DC, after an introduction by former CIA Iran Operations Chief and EVP of Strider Technologies, Anthony DeMario

“I appreciated the opportunity to virtually join the event. You’ve assembled an impressive mix of talent and expertise.” - Stan McChrystal (Founder and CEO, The McChrystal Group)

From the left: Iron Butterfly Media co-founders Cadie Naquin Hopkins and Megan Jaffer, CIA veterans Laura Thomas and Carmen Medina, and 9-year old future spy Natalie

“My favorite memory from the summit, was being able to bring my daughter Natalie to see the documentary “The Power We Hold: Stories from Women Spies” and for her to meet so many great people from the Community. I think that the summit’s inspiring experience will stay with her for the rest of her life.” - Matt Zacharias (Attendee)

Kyle Sweet, CSO of Helio Risk, at our Howler’s Ridge fundraiser, discussing how he and his guests can support PTSD treatment protocols planned for Howler’s Ridge with actor Taylor Kitsch (Terminal List: Dark Wolf)

"The WSS was a tremendous experience for our company. Exploring global risks and projected issues in geopolitics and national security, intelligence and defense is exactly the type of gathering we've been looking for. The collaborative model of the WSS lends itself really well towards interacting with true subject matter experts. We are already looking forward to next year. Best summit in best environment." - Kyle Sweet (Chief Strategy Officer, Helio Risk)

Howard Gordon: Co-creator of Homeland; Showrunner- 24 and X-Files

“My favorite memory was more of a post-event observation about the depth and breadth of super-smart, serious people - both presenters and attendees - who were there.” - Howard Gordon (Award-winning Writer and Producer)

This is the first in a series of dispatches from the inaugural Whitefish Security Summit. Part II drops Monday, April 20th, with additional attendee feedback, photography from across the two days, and deeper coverage of the programming. Video coverage will follow in Part III.

None of this would have been possible without the support of our sponsors: Strider Technologies, Red5, Helio Risk, Ledlow Security Group, 5 Stones Intelligence, Acorn Capital Management, and Four Branches Bourbon. Their investment in this community made the Summit what it was — and we’re grateful.

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