Let’s be honest…

Most sales outreach is garbage.

It’s lazy, templated, and gets ignored.

In this episode of The Sales Machine, I sat down with the guy who’s been rewriting the sales playbook for over a decade—Ryan O’Hara, former VP of Growth at LeadIQ, founder of Pitchfire, and all-around creative prospecting beast.

We dive deep into how to stand out in a crowded inbox, how to use humor, storytelling, and even steak dinners to build real relationships with prospects and why generic templates and cold emails just don’t cut it anymore.

If you're looking for ways to break through the noise, get more replies, and actually book meetings with people who want to talk to you… this one’s for you.

🔥 What You’ll Learn:

• How creative prospecting can make your team unforgettable
• Why humor disarms and converts way better than scripts
• How to use paid responses and “ethical bribes” without crossing the line
• Why sales is no longer just about value, it’s about experience
• The power of storytelling in outbound strategy
• How to personalize outreach at scale (without burning your team out)
• Why steak dinners and custom gifts are still winning deals
• How to future-proof your sales strategy in a world of AI and noise

If your outreach feels like it’s falling flat…

It’s time to change the game.

Hit play, steal some ideas, and personalize your way to 10x replies.

Episode Highlights

"Cold outreach today is all about being memorable, not just relevant." - Ryan O’Hara

"Most people are still sending the same outreach they were five years ago and wondering why it’s not working." - John Rankins

"The art of building relationships can be fun and cool." - Ryan O’Hara

"Sales is a relationship game now. If you're not building trust, you're building resistance." - John Rankins

"If you use humor, it disarms people and makes the conversation easier." - Ryan O’Hara

"I’d rather pay for a response than waste time chasing ghost leads." - John Rankins

Chapters

(03:09) - Creative Prospecting Strategies

(05:55) - The Evolution of Prospecting and Marketing

(08:53) - Building Relationships in Sales

(12:07) - Scaling Sales Teams and Company Growth

(14:58) - The Importance of Storytelling in Sales

(18:13) - Transitioning from Dine to Lead IQ

(21:01) - The Launch of Pitchfire and New Approaches

(23:59) - Challenges and Lessons from International Sales

(27:05) - The Future of Prospecting and Sales Strategies

(43:35) - The Value of Paid Responses

(44:27) - Innovative Meeting Strategies

(46:10) - Lessons from Past Experiences

(49:45) - The Ethics of Compensation in Sales

(51:51) - Building Relationships through Dinners

(52:55) - Field Sales Tactics and Discovery

(55:41) - The Importance of Customer-Centric Approaches

(56:13) - Giftology and Unique Outreach Strategies

(01:01:54) - Creating Memorable Impressions

(01:05:32) - The Art of Personalization in Sales

Connect with Ryan O’Hara

LinkedIn: https://www.linkedin.com/in/ryanmohara/ 

Facebook: https://www.facebook.com/thepitchfire/ 

X: https://x.com/Ryohara 

Instagram: https://www.instagram.com/drryanohara/ 

Connect with John Rankins

Website: https://thesalesmachine.com/

Facebook: https://www.facebook.com/TheSalesMachineOfficial

Instagram:https://www.instagram.com/thesalesmachine_official/

LinkedIn:https://www.linkedin.com/company/thesalesmachineofficial/

YouTube:https://www.youtube.com/@JohnRankinsOfficial