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The Long Game by Ryan Richards
The Long Game by Ryan Richards is a podcast about how real operators think, decide, and build for the long term — and what actually happens behind the scenes when the stakes are real.
Narrated and hosted by Ryan Richards, the show pulls back the curtain on business, real estate, and investing through unfiltered conversations with operators, investors, and builders who have earned their perspective. You’ll hear what worked, what didn’t, and the decisions most people never see or talk about publicly.
This isn’t surface-level advice or polished success stories. It’s a fly-on-the-wall look at high-caliber conversations — the mental models, systems, mistakes, and tradeoffs that shape durable success over time.
Through solo reflections and deep conversations, The Long Game gives listeners proximity to real operators and the clarity that comes from understanding how the best actually think, judge risk, and execute.
If you’re an ambitious builder who wants to learn from real experiences — not shortcuts or hype — this is an invitation inside.
Welcome to The Long Game.
The Long Game by Ryan Richards
Ep. #73 | From “Boots on the Ground” to Building a Scalable Operation with Grindstone Sealcoating
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In episode 73 of The Long Game, Ryan sits down with Nick Lavallee and Nathan Hoy, the co-owners of Grindstone Sealcoating, to talk about what it really looks like to evolve from solopreneurs doing everything themselves into operators building a business that can grow without them in the field every day.
Nick and Nate break down their asphalt maintenance business model, why education is such a big part of winning customers, and the exact inflection point where they realized they were capped on revenue if they stayed “boots on the ground.” From 10-hour sealcoating days followed by quoting jobs until 9PM, to hiring their first full-time office admin, this episode is a real look at the messy middle of scaling.
They also get into leadership, team culture, and how they’re building a repeatable blueprint that could eventually expand Grindstone well beyond New England.
What you’ll learn:
- What sealcoating actually is and why it protects a homeowner’s investment
The cost difference between sealcoating vs. repaving and why education sells the job - The moment they realized they were capped and had to start hiring
- How they approached hiring their first full-time office admin and what they learned from interviewing 20+ candidates
- Why leadership, clarity of roles, and setting “success standards” matters more than micromanaging
- How seasonal businesses keep culture and employee relationships strong in the off-season
- Their “Mount Everest” vision and the blueprint mindset for expanding into 20 to 30 states
If you’re building a service business and you’re stuck in the loop of doing the work all day and running the company at night, this episode will hit home. Nick and Nate lay out the real-world mindset shift it takes to start buying back your time and building something that can scale.
#TheLongGamePodcast #FinancewithTeamRichards
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