25 Years of Bob, Jeremy & Reality: Lessons from Building a Training Business

The Reality of Business

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What does it take to build a successful sales training business - and still be laughing 25 years on?

In this special anniversary episode, Bob and Jeremy reflect on the lessons, surprises, and stories they’ve collected over a quarter of a century of running a training company.

One of the biggest revelations? Learning to take business a little less personally. As Bob admits, “Every knockback felt like a blow to the heart” in those early days. Over time, they learned to separate self-worth from outcomes - building resilience, perspective, and a clearer sense of what drives long-term business success.

From standout leadership moments to spontaneous karaoke, the stories span cities, countries, and conference rooms. You’ll hear tales from Dublin to Delhi, and Amsterdam to Atlanta - all reinforcing a simple truth: business growth often comes from the unexpected. Whether it’s a three-hour wine-fuelled lunch in France, or a client mix-up that sparks a brand-new idea, there’s wisdom in the unplanned.

There’s practical insight here too - around investing in personal development, taking time to reset, and remembering that culture, connection, and not taking yourself too seriously are all part of a sustainable leadership journey.

Whether you’re leading a business, growing a team, or reflecting on your own path, this one’s for you.

What’s the biggest lesson you’ve learned in your own business journey? We'd love to hear your stories and questions!

For more info, free resources, useful content & our blog posts, please visit realitytraining.com.
Reality Training - Selling Certainty

Chapters

1. Celebrating 25 Years in Business (00:00:00)

2. Biggest Business Lessons Learned (00:03:03)

3. The Value of Taking Time Out (00:10:37)

4. Best Memories and Greatest Moments (00:17:45)

5. Favorite International Training Experiences (00:26:36)

6. Hilarious Stories and Future Plans (00:33:49)