In this episode of Chess Not Checkers, Keith Riddle and Jordan Tampien sit down with Li Ciavola, a climber, real estate professional, and lead instructor for the Spokane Mountaineers, fresh off summiting Denali, the tallest and arguably toughest of the seven summits.
Li takes us inside all 23 days on the mountain: pulling 160 pounds of gear across a crevassed glacier, riding out blizzards for days at a time, and the harrowing night his teammate nearly died of altitude sickness at 11,000 feet, which forced Li to navigate a whiteout alone with nothing but his phone and a fading battery. It is a gripping, high-stakes story told in vivid detail.
But the real payoff is what climbing teaches about the long game. Li, Keith, and Jordan draw the throughline between the mountain and business: managing risk instead of avoiding it, making clear-headed decisions under pressure, and knowing when to push and when to turn around. Li also shares how real estate bought him the time freedom to chase the mountains in the first place, closing deals from a rope thousands of feet up.
Whether you are a climber, an entrepreneur, or someone weighing the risks in your own big pursuit, this is a conversation about resilience, resourcefulness, and playing the long game. Follow Li on Instagram @dingos.domain to see the photos from his Denali climb.
Show Flow:
00:00 Meeting Li and the Ciavola Name
02:04 Why Denali Is the Toughest of the Seven Summits
06:13 Altitude Sickness and Li's Climbing Background
09:26 Climbing Unguided: A Year of Prep and 160 Pounds of Gear
21:52 A Teammate Goes Down: The Emergency at Camp 11
34:48 Alone in a Whiteout
45:48 Type Two Fun, a New Teammate, and Tragedy on the Mountain
53:33 Risk, Reward, and What Price You're Willing to Pay
57:09 Climbing as Risk Management and a Metaphor for Life
1:03:23 Real Estate, Time Freedom, and Closing Deals From a Rope
