Chess Not Checkers

Jordan Tampien & Keith Riddle
  • 5.0 (18)
  • Entrepreneurship
  • Updated Weekly

Welcome to Chess Not Checkers, the podcast that teaches you how to play the long game in both business and life. Hosted by Keith Riddle and Jordan Tampien, we dive deep into strategic thinking, exploring how the best minds think several steps ahead. Each episode features guests from a variety of fields — real estate, business, health, wealth, and more — who share their stories and the unique mindset that’s propelled their success. Whether you’re building, growing, or establishing your business, this show offers valuable insights to help you think smarter and act with purpose.

  1. 2d ago

    Cody Arguelles on Running for Spokane City Council and Building The Late Arrival Club

    In this episode of Chess Not Checkers, Keith Riddle and Jordan Tampien sit down with Cody Arguelles, founder of the Late Arrival Club, a private members' lounge in downtown Spokane, and a man with one of the more unexpected paths to entrepreneurship you will hear. Cody starts with the club itself, a whiskey-and-cigar community he built with a group of fellow veterans, where the only real requirement is being the kind of person who can disagree, shake hands, and still grab a beer. From there, he shares his story of becoming an Air Force SERE specialist, the strange post-military pitch that pulled him toward business, and how he eventually landed on building a place of his own. The conversation gets into his run for Spokane City Council, why he runs as an independent, and his blunt take on how far the political parties have drifted from each other. Keith, Jordan, and Cody dig into what happens when people who have never built or stewarded anything end up making the rules. Whether you are a veteran, an entrepreneur, or someone who just wants to build something real in your own city, this is a candid, story-rich conversation about service, self-reliance, and getting to yes.  Learn more about The Late Arrival Club and how to join at latearrivalclub.com. Show Flow 00:00  Welcome, Cody Arguelles of the Late Arrival Club 03:30  What the Late Arrival Club Really Is 10:30  Reading People and Who You Let In 13:50  Signing Up Blind: Choosing the SERE Path 17:14  What He Misses Most About the Military 23:55  Manipulation Training and How People Break 30:49  Local Politics Is Local: Why He Ran 34:23  Being Conservative, Running Independent 41:30  How He Out-Raised the Career Politicians 44:59  Where Government Makes Problems Worse 55:22  Who Should Be Making the Rules 1:05:40  A Magic Wand: Spokane in Five Years 1:15:46  Burned-Out Developers and Betting on the City 1:22:43  The Fight to Smoke in His Own Private Lounge 1:26:04  Wrap-Up

  2. Sep 22

    Devin Mecham of NAI Black on the Office Slump, the Building Boom, and the Long Game

    In this episode of Chess Not Checkers, Keith Riddle and Jordan Tampien sit down with Devin Mecham, designated broker of NAI Black, for an insider's look at commercial real estate and where Spokane goes from here. Devin shares how he got into the business, and the guys dig into the market from a commercial lens: why the office sector has taken such a hit, how downtown and public safety factor in, and whether office can ever be a strategic investment again. They also look ahead to the building boom they expect as the region rebuilds after the fires, and who is actually positioned to win that work. From there the conversation turns to the bigger forces shaping the city: the permitting headaches and Growth Management restrictions that stall good projects, the opportunity and the questions around data center development, and the hard truth that everyone says they love Spokane while pulling it in very different directions. Jordan even gets candid about rethinking how he wants to play real estate going forward, and why he is leaning more commercial. Whether you are an investor, a developer, or just someone who cares about where Spokane is headed, this is a candid, in-the-weeds conversation about real estate, civic vision, and playing the long game. Learn more about Devin at NAI Black. Chapters: 00:00 Welcome, Devin Mecham of NAI Black 03:24 How Devin Got Into Real Estate 07:00 Missing Bedtime: The Numbers and the Why 10:24 Reading a Commercial Deal (Without the Jargon) 13:47 The Coming Rebuild Boom and Who Wins It 17:25 Why the Office Sector Fell 20:48 Buying Office: Cap Rates and Staying Power 24:10 Tenant Improvements, Leases, and the Real Math 27:32 Growth, Permitting, and the GMA Problem 34:16 Property Taxes and Getting Stonewalled 40:56 Data Centers: Opportunity and Questions 44:28 Loving Spokane, Disagreeing on the Vision 51:31 When the Rules Change Out From Under You 54:56 Buy Well, Never Sell: Lessons and Case Studies 61:45 74 Projects In: Rethinking How to Play It 65:08 Partnerships and Final Thoughts

  3. Sep 15

    Revisiting Brynn MacLennan – What It Takes to Build a Product People Use

    We're revisiting one of our favorite conversations. Keith Riddle and Jordan Tampien sit down with Brynn MacLennan, CEO and co-founder of Slate, the company reinventing something almost nobody enjoys: flossing. Brynn walks through the whole arc, from the first spark of the idea in 2019 to launching an electric flosser in 2022, and everything that came with scaling a physical product through a pandemic. She's honest about what it actually takes: the innovation, the leadership calls, the team culture you have to build, and the curveballs you never see coming. Whether you're chasing a business idea of your own or you just dread flossing, there's something in this one for you. That's what makes it worth a second listen. Learn more at slateflosser.com Show Flow 00:00 Welcome, Brynn MacLennan of Slate 03:14 A Dentist, a Problem, and the Idea for Slate 06:37 What It Really Takes to Make a Physical Product 09:56 Spending $24K to Get Started 13:11 Regrets, Passion, and Loving the Product 16:27 Flossing, Correlation, and Not Wanting to Die 19:41 Grit vs. Stubbornness: Knowing the Difference 23:00 Bringing More Voices Into the Business 26:24 "Every Day I Realize I Know Nothing": Learning as a Leader 32:55 How Slate Actually Gets Made and Shipped 52:24 Leading People Without Losing Yourself 1:02:14 Hiring for Behavior, Not Just Skill 1:08:51 Playing Chess, Not Checkers: Final Thoughts

  4. Sep 8

    Inside Spokane Development with Keith and Jordan

    In this episode of Chess Not Checkers, Keith Riddle and Jordan Tampien pull back the curtain on something they usually only mention in passing: the real mechanics of real estate development. Whether you are an investor, a developer, a would-be flipper, or just trying to make sense of today's housing market, this episode is a candid, numbers-and-all look at how real estate really works, and a reminder that at some point, as Jordan puts it, you have to pick a life instead of just collecting stuff. Show Flow 00:00  Breaking Down a Real Deal for Once 02:39  The Peyton: Seven Stories, 96 Units 07:44  Tax Credits, Lenders, and a Loan That Nearly Fell Apart 12:44  Why a Pro Forma Is Worthless Once You Dig In 20:40  The New Rules: Rates, Holding, and Who Wins 25:48  Where Values Are Actually Falling 28:18  Rebuilding After the Fires vs. Your Insurance Payout 36:13  Spokane's Renovator's Market and the Return on a Flip 46:39  50,000 Older Homes and Why More Flippers Would Help 49:09  Oversized Houses and the Shift in What Buyers Want 56:59  The Hidden Costs of Owning a Home 1:12:42  Sentiment, and Reconnecting 1:22:30  Final Thoughts and Wrap-Up

  5. Sep 1

    Li Ciavola Returns: The Man Behind the Climb

    Li Ciavola is back. After his gripping Denali story last time, Keith Riddle and Jordan Tampien bring the climber back to Chess Not Checkers to get to know the man behind the mountain. This time the conversation is less about the summit and more about everything around it. Li opens up about what happens after you finally reach a goal you chased for a decade, the strange emptiness of the victory, the search for the next driving force, and why so much of life turns out to be about the chase rather than the win. Whether you are chasing a goal, wrestling with what comes after one, or just trying to figure out what enough looks like, this is a thoughtful, wide-ranging conversation about ambition, contentment, and building a life you actually want. Follow Li on Instagram @dingos.domain. Show Flow 00:00  Welcome Back: The Man Behind the Climb 03:00  What's Next: Avalanche Education for Spokane 06:00  "You Gotta Pick a Life" 12:00  Presence, Trade-offs, and Going All In 21:00  Where Frustration Comes From, and the Grass Isn't Greener 27:00  Growth, Trust, and the Flame That Tempers Steel 33:00  Scaling Four Degrees and Hard Lessons 39:00  Life at Sea: Selling Luxury on Cruise Ships 54:00  Dressing the Part and Reading the Room 63:00  College, Italy, and Your Twenties 66:00  Comparison, Status, and Never Enough 78:00  Naming Your Mountain and Staying Consistent 86:30  Final Thoughts and Wrap-Up

  6. Aug 25

    Revisiting Bobby Brett – The Man Who Bet on Spokane

    We're revisiting one of our favorite conversations. This episode of Chess Not Checkers first aired June 10, 2025, and it's well worth a second listen. Keith Riddle and Jordan Tampien welcome Bobby Brett, whose life has straddled two worlds that shaped modern Spokane: professional sports and real estate. Raised in a family where competition was a way of life, Bobby carried that drive far beyond the diamond, turning a love of baseball into a career that reached into nearly every corner of the city. When his playing days wrapped, Bobby set his sights on real estate, and the timing proved pivotal. In 1985 he made the kind of move that defines a career, buying a Spokane minor league club and building it into the beloved Spokane Indians. He later added the Spokane Chiefs to his roster, becoming one of the most recognizable names in the region's sports scene. Off the field, his patient approach to property, buying quality real estate and holding it for the long haul, helped him leave a permanent mark on the way the city grew. In this conversation, Bobby pulls back the curtain on both pursuits: the instincts behind his biggest bets, how the Spokane market compares to places like California, the value hiding in the city's historic buildings, and the hard-won lessons he'd pass along to anyone hoping to invest and build something that lasts. Chapters: 00:00  Introduction 00:35  Bobby Brett's Early Life and Family Background 01:34  Journey to Spokane and Minor League Baseball 03:21  First Impressions of Spokane 04:21  Buying the Spokane Indians 10:38  Transition to Real Estate 14:45  Early Real Estate Ventures 22:12  Real Estate Strategies and Lessons 33:11  A Coach's Journey to Real Estate 33:53  Comparing Real Estate Markets: Spokane vs. California 35:01  Investing in Spokane's Historic Buildings 36:31  Challenges and Opportunities in Downtown Spokane 37:28  The Impact of Politics on Real Estate 40:06  The Value of Long-Term Real Estate Investment 46:35  Advice for Aspiring Real Estate Investors 50:18  Reflecting on Real Estate Market Trends 01:02:07  The Unique Appeal of Spokane's Sports Teams 01:03:03  Parting Words

  7. Aug 18

    Ted Schmidt of ActionCOACH Northwest on Knowing Your Numbers and Building to Exit

    In this episode of Chess Not Checkers, Keith Riddle and Jordan Tampien sit down with Ted Schmidt, a Spokane native who turned a local tool and equipment rental company into a regional powerhouse before finding his second act as a business coach. Ted shares the story of AA Rentals, how he worked his way up from a college job to partner and helped grow the company to 22 locations and roughly 400 employees across the I-5 corridor, right up until a major international buyer made an offer they could not refuse. After the sale, he and his wife left the rat race and came home to Spokane. These days Ted coaches business owners through ActionCOACH Northwest, and the conversation digs into the hard-won lessons behind that work: why you should build an asset, not a job, and start with the end in mind; why knowing your numbers still matters in the age of AI, since a tool can build the spreadsheet but not tell you which questions to ask; how leaders and employees alike hit a ceiling when they stop growing; and why so many owners wait until they are burned out to make their first hire. Whether you are a solopreneur eyeing your first hire, an owner trying to scale, or someone dreaming about an eventual exit, this episode is full of practical wisdom on building a business that can run, and grow, without you. Learn more about Ted's coaching at ActionCOACH Northwest: actioncoachnw.com Show Flow 00:00  Meet Ted Schmitt, Spokane Native 02:30  Building AA Rentals to 22 Locations 05:00  Industry Consolidation and Selling the Company 07:30  What College Missed About Real Business 12:30  Learning to Live by Your Numbers 17:38  The Second Act: Coaching Business Owners 22:44  Build an Asset, Not a Job 27:50  Systems, Conversion, and Knowing the Right Questions 33:00  It All Comes Down to Your Team 40:39  Knowing Your Numbers and Breaking Even on a Hire 45:42  Letting Go: Why Control Is a Weak Leader's Move 55:58  Creating Space and the First Hire

  8. Aug 11

    Living Through the Spokane Fires: Perspective in Real Time with Jordan and Keith

    As wildfire moves through the Spokane area, Keith Riddle and Jordan Tampien set the business talk aside for a more personal conversation about what happens when disaster hits close to home. They open with the fire itself: the sudden evacuations across Indian Trail, Five Mile, and West Francis, the hundreds of homes lost, and why this one hit Eastern Washington harder than anything in recent memory.  B Keith and Jordan reflect on how moments like these strip away the noise and remind us what actually matters, not the bigger house or the nicer car, but the people we love and the time we have with them. They get into the lessons underneath the loss: why we overestimate what we can do in a day and underestimate what we can do in a year, the quiet power of the seeds we plant in others, and how to move through a hard season in a way that is honest but still productive. Whether you are in Spokane or watching from afar, this is a heartfelt conversation about resilience, gratitude, and keeping the main thing the main thing when life turns upside down. Show Flow 00:00  Spokane on Fire: What We're Watching Unfold 04:00  Evacuations and the Escape-Route Problem 08:00  Disbelief, Delay, and Gridlock Getting Out 12:00  What Recovery and Rebuilding Actually Involve 16:00  Insurance, Fire Zones, and the Cost to Rebuild 18:00  The Water, the Runoff, and the Environmental Toll 24:00  Lessons from the Palisades Fire 26:00  Making It About Yourself vs. Showing Up for Others 30:00  What You'd Grab, and What Really Matters 36:00  Grieving Without Getting Stuck 42:00  Finding What You're Made Of in Hard Times 54:00  Small Connections, Big Impact, and Where We Go Next

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Trailer

5
out of 5
18 Ratings

About

Welcome to Chess Not Checkers, the podcast that teaches you how to play the long game in both business and life. Hosted by Keith Riddle and Jordan Tampien, we dive deep into strategic thinking, exploring how the best minds think several steps ahead. Each episode features guests from a variety of fields — real estate, business, health, wealth, and more — who share their stories and the unique mindset that’s propelled their success. Whether you’re building, growing, or establishing your business, this show offers valuable insights to help you think smarter and act with purpose.

Information

  • Creator
    Jordan Tampien & Keith Riddle
  • Years Active
    2025 - 2026
  • Episodes
    84
  • Rating
    Explicit
  • Copyright
    © Jordan Tampien & Keith Riddle
  • Show Website
    Chess Not Checkers

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