Chess Not Checkers

Jordan Tampien & Keith Riddle
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  • Entrepreneurship
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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. 2 days ago

    Gavin Cooley, President of the Spokane Business Association, on How Spokane Turns It Around

    In this episode of Chess Not Checkers, Keith Riddle and Jordan Tampien sit down with Gavin Cooley, president of the Spokane Business Association and the city's former longtime CFO, for an honest conversation about homelessness, addiction, and the future of Spokane.  Gavin shares what cities like Houston and Boise have figured out: that this is not mainly a funding problem but a collaboration problem, and that saving lives and keeping streets clear are not opposing goals. The three of them get into the "one-third rule," why silos and turf wars stall progress, the difference strong leadership makes, and the harder human questions of indifference, compassion, and accountability. Through it all runs a stubborn hope that Spokane could become the comeback story other cities study. 00:00  Welcome, Gavin Cooley 00:47  Eight Kids, Fifteen Grandkids, and Growing Up in Spokane 03:33  The Bridge Over the Falls That Never Happened 07:21  From City CFO to Studying Homelessness 08:20  What Houston Got Right 11:40  Getting Everyone Under One Umbrella 15:45  Trying to Bring the Houston Model to Spokane 19:55  Why It's Not a Funding Problem 21:21  Condon's Collaborative Approach 22:20  When Fentanyl Changed Everything 28:30  Why the Problem Persists 31:20  The False Dichotomy of Compassion vs. Accountability 36:50  San Francisco's One-Year Turnaround 40:20  On-Street Patrol and the One-Third Rule 43:45  What a Real Response Would Look Like 50:00  Leadership, Admitting You're Wrong, and the Hard Pivot 55:15  Spokane Could Be the Comeback Story 58:30  Why Spokane Is More Resilient Than You'd Think 01:03:00  The Danger of Normalizing It 01:09:25  This Is Who Spokane Really Is 01:14:00  When There's a Clear Way to Help, Spokane Shows Up 01:18:55  Final Thoughts

  2. 20 Oct

    Cal Spoon of Insurance Busters on How Insurance Really Works PART 1

    In this episode of Chess Not Checkers, Keith Riddle and Jordan Tampien sit down with Cal Spoon of Insurance Busters, a public insurance adjuster Keith met through the local fires. If you have ever filed an insurance claim, or ever will, buckle up, because this one will change how you look at the whole system. Cal pulls back the curtain on a profession almost nobody has heard of, and in doing so explains how insurance actually works. He gets into why the policy you signed is really a contract, the "duties after a loss" buried on page 33 that most people never read, and why the adjuster the insurance company sends works for them and not for you. Along the way, he breaks down how premiums get invested, how carriers use data and old software to predict the exact number you will accept, and why so many claims get settled for a fraction of what is actually owed. He also gets practical. Cal walks through what to do if you are in the middle of a claim right now, why you should pause before accepting a goodwill offer, the difference between replacement cost and actual cash value, how matching and "line of sight" tricks work on roof claims, and why a quick lawsuit can actually cost you more than it recovers. Plus, why he shows up to disaster zones with a smoker and feeds the community instead of buying ads. This is part one of a two-part conversation. Learn more about Cal at insurancebusters.net. Show Flow 00:00  Welcome, Cal Spoon of Insurance Busters 01:34  What Is a Public Adjuster? 03:40  Where Modern Insurance Really Started 05:05  Your Premiums Are Invested in a Hedge Fund 08:16  Futures, Forecasts, and What the Carrier Really Knows 12:18  Colossus: The AI That Predicts Your Payout 16:06  Why You Trust the Company That Owes You Money 19:30  It's Not a Policy, It's a Contract 22:40  Goodwill Offers and Buying Your Silence 25:26  Mold, Civil Authority, and the But-For Doctrine 33:00  How to Actually Shop for Insurance 37:46  A1 vs. A2: The $180 Mistake That Costs Six Figures 46:55  What to Do If You're In a Claim Right Now 53:00  Why He Brings a Smoker Instead of Buying Ads 58:55  Why Insurance Busters Litigates Most Claims 01:00:30  The Sworn Proof of Loss and Pricing a Claim 01:03:30  Roofs, Decking, and Why Patches Don't Cut It 01:06:45  Replacement Cost vs. Actual Cash Value 01:08:05  The Float: How Carriers Make Money Holding Yours 01:17:15  Wrap-Up and Where to Find Cal

  3. 13 Oct

    Lance Beck of GSI on Vision, Growth, and Getting Spokane to Yes

    In this episode of Chess Not Checkers, Keith Riddle and Jordan Tampien sit down with Lance Beck, chief strategy officer at Greater Spokane Incorporated and former president and CEO of the Valley Chamber, for a wide-ranging conversation about the past, present, and future of Spokane. Lance traces his own path from studying servant leadership at Whitworth to low-income housing work to running a chamber of commerce, and how that shaped his belief that the best solutions come from seeing people and places holistically. From there the three of them dig into the forces shaping the region right now: the cost of doing business in Washington, the permitting and building-code hurdles slowing the fire rebuild, the data center debate, and why so much of the public conversation gets stuck fighting at the edges instead of the 40 percent everyone actually agrees on. At its heart, this one is about vision and who carries it. Keith, Jordan, and Lance get into infill and the Garland and North Monroe transformations, the risk a developer takes to build something cool instead of something safe, why leadership has shifted from authority to influence, and how a community rallies behind the people willing to put their name on the line. It is an honest, hopeful look at a mid-size river city with a bigger upside and a smaller mess to clean up than the markets around it. Learn more about Greater Spokane Incorporated at greaterspokane.org. Show Flow 00:00  Welcome, Lance Beck 01:40  A Northsider and a Passion for Leadership 04:10  Learning to See People, Not Just Stats 08:30  Why Business Took the Baton on Public Safety 10:30  Fighting at the Edges vs. the 40 Percent We Agree On 13:00  Homelessness, Visibility, and the Crime Question 15:25  Accountability and the Joint City-County Approach 18:50  Doing Business in Washington vs. Idaho 20:20  The Fire Rebuild, Building Codes, and Sales Tax 21:40  Data Centers, Energy, and Learning from Grant County 23:00  Spokane's Lost Edge: Cost of Living 27:30  A Spending Problem, Not a Revenue Problem 30:50  Why the Jail Became a Processing Center 33:40  Systems of Care vs. Working in Silos 35:40  Quick Fixes, Long Problems, and the Anti-Parking Fight 38:25  Garland, North Monroe, and Earning the Infill 46:30  Why Build Something Cool Instead of Something Safe 50:00  Who Are Spokane's Visionaries Now? 54:45  Leadership Shifting from Authority to Influence 57:30  Supporting a Culture That Rewards Taking the Risk 01:03:30  What Walt Worthy Means to This Community 01:05:00  Vision Makes the Criticism Easier to Take 01:09:12  What's Actually an Advantage About Spokane 01:12:10  The Downtown Paradox and Commercial Vacancy 01:15:46  Four "What If" Statements for the Region 01:18:45  Ownership, Action, and Casting the Vision 01:20:12  How to Get Involved with GSI

  4. 6 Oct

    Revisiting Luc Jasmin – From Boston to Building Spokane's Future

    In this episode of Chess Not Checkers, Keith Riddle and Jordan Tampien sit down with Luc Jasmin to talk community, policy, and the challenges shaping Spokane today. Luc shares his journey from Boston to becoming a first-generation Haitian American leader in the Pacific Northwest, and how he got into politics through early childhood education advocacy.They dive into the realities of housing, workforce, and regional development, and how creative, collaborative solutions can make a real difference. Luc also shares how government can better meet community needs and the power of building consensus to drive change.If you care about Spokane, policy, or just want to hear a thoughtful conversation about improving communities, this episode is for you.

  5. 29 Sept

    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

  6. 22 Sept

    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

  7. 15 Sept

    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

  8. 8 Sept

    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

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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
    88
  • Rating
    Explicit
  • Copyright
    © Jordan Tampien & Keith Riddle
  • Show Website
    Chess Not Checkers

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