The Cheat Code & Friends

Join us for a lively conversation with Dan Tyre, one of HubSpot’s earliest employees and a passionate advocate for startup growth, sales excellence, and lifelong learning. With humor and energy, Dan shares his journey at HubSpot and how the company’s sales strategy evolved alongside a rapidly changing workforce. 
 
From tackling ageism in tech to highlighting the value of curiosity, this episode explores what it takes to succeed in today’s job market. Dan shares practical tips on adaptability, preparation, and building strong relationships, offering a roadmap for anyone navigating career growth or startup life. 

Chapters 

02:59 The Journey of Dan Tyre at HubSpot 
06:08 The Evolution of Work and AI 
09:03 Building Relationships in Business 
11:59 Creating Value for Startups 
13:47 The Evolution of HubSpot's Sales Strategy 
15:53 Ageism in the Workplace: A Personal Perspective 
22:03 Building a Culture of Learning and Adaptability 
30:06 The Importance of Curiosity and Business Acumen 
34:15 The Power of Business Acumen in Sales 
35:58 Curiosity and Learning in Sales 
39:31 Identifying and Developing Sales Talent 
42:55 Navigating the Future Workforce 
46:02 The Importance of Preparation in Interviews 
51:29 Closing Thoughts on Competitive Advantage 

References in the Show: 

https://www.entrepreneur.com/business-news/fiverr-ceo-says-ai-will-take-your-job-heres-what-to-do/491198 
 
https://www.marketwatch.com/story/why-a-record-number-of-adults-over-65-are-working-and-its-not-just-about-money-85d2f15d?utm_source 
 
https://www.marketwatch.com/story/why-a-record-number-of-adults-over-65-are-working-and-its-not-just-about-money-85d2f15d?utm_source 
 
https://www.linkedin.com/pulse/experts-weigh-why-2025-holds-hope-older-workers-janine-vanderburg-tytkc/  
 

Quote of the Show:
 

“Who needs a 66-year-old man telling them what to do, right? That's stupid. This is the modern age and you've got to be smart enough to say, alright, I know what this person needs and then ask the right question so you play inception, right?” - Dan Tyre 

 
Ways to Tune In: 

What is The Cheat Code & Friends?

Serial entrepreneurs and operators Justin Gray, Josh Wagner & Sean Kester combine decades of B2B and GTM expertise with unwavering honesty to unpack the latest news (fake or otherwise) on The Cheat Code & Friends Podcast. Combined with a rotating guest list of founders, practitioners and investors, the no-nonsense forum gathers fortnightly, holding court to translate headlines into reality and discuss the impact for early-stage businesses. The Cheat Code is just that, the trusted folks we look to for advice and insight, and we hope to bring the same to you.