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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. #75 | How Authentic Marketing Wins in the AI Era with Tara Ostromecky
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In this episode of The Long Game, Ryan Richards sits down with Tara Ostromecky, founder and CEO of Makin' It Marketing, for a conversation about what it really takes to grow a business in today’s fast-changing marketing landscape.
Tara shares how she turned a passion for creativity and entrepreneurship into a nationally-serving marketing company based in Worcester, serving clients across the country. From building her business at a young age to hiring her first team members, Tara opens up about the lessons she has learned around growth, leadership, authenticity, and adapting in the age of AI.
Ryan and Tara also dive into how marketing has changed since COVID, why so many businesses are struggling to stand out online, and why human connection, trust, and clear strategy matter more now than ever. They discuss the real role of AI in marketing, how business owners should think about personal branding, and why outsourcing the right tasks can unlock the next stage of growth.
What you’ll learn:
- How Tara built Makin' It Marketing from a solo venture into a growing agency
- Why authenticity is becoming more valuable as AI-generated content becomes more common
- The right way to use AI in marketing without losing your voice
- What business owners should focus on if they want better results online
- Why websites, email lists, and SEO still matter in 2026
- Lessons Tara learned about hiring, managing interns, and trusting a growing team
- How visibility and kindness both play a major role in long-term business success
If you are a business owner, entrepreneur, or marketer trying to grow in a world where trends, platforms, and technology keep changing, this episode will give you practical insight on how to stay relevant while building a brand people actually trust.
GUEST INFO:
Tara Ostromecky
www.makinitmarketing.com
Instagram | @makinitmarketing @adventures.with.tara | @tara.o
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