Episode Summary

In this episode of Million Dollar Flip Flops, Rodric sits down with Colin Herdman — lifelong entrepreneur, co-founder of Monkey Island Ventures, and founder of Rainmaker, a company helping business owners grow their network, leads, and sales using LinkedIn.

Colin shares how he went from launching his first business a week after college to building multiple companies across digital marketing, software development, and LinkedIn growth strategy. Along the way, he’s learned that real business growth still comes down to the same fundamentals: understanding your audience, teaching what you know, and building genuine relationships.

Rodric and Colin also dig into AI, the future of marketing, community building, and why LinkedIn live streams may be one of the most underrated tools available for founders, coaches, and sales leaders today.

This is a conversation about growth, yes — but even more, it’s about authenticity, education, thought leadership, and how to stand out online without becoming just more noise.

In this episode, you’ll hear:

Colin’s journey from college graduate to lifelong entrepreneur
The story behind Monkey Island Ventures
What his three companies are focused on today
Why AI is changing marketing — and what it cannot replace
Why community may become even more valuable in an AI-heavy world
Colin’s philosophy for using LinkedIn the right way
The difference between creating noise and creating trust
Why educational content beats salesy content on LinkedIn
How Colin uses LinkedIn live streams to generate leads and referrals
A step-by-step breakdown of his LinkedIn live stream strategy
Why repetition and thought leadership matter more than constant content churn

Highlights & Timestamps

[00:00] Colin’s core LinkedIn philosophy

Colin explains the big idea behind his approach to LinkedIn: authenticity, education, experimentation, and understanding what your audience can learn from you.

[01:00] Meet Colin Herdman

Colin introduces himself as a lifelong entrepreneur who launched his first business one week after college.

[01:00] From criminal justice degree to entrepreneurship

He shares how he never used his degree and instead learned business through experience and the school of hard knocks.

[02:00] The businesses Colin is building today

Colin breaks down the three companies under Monkey Island Ventures: Aurion, Cloudburst, and Rainmaker.

[03:00] What’s changing fastest in marketing right now

Rodric asks Colin about the biggest shifts in marketing, and Colin points straight to AI, automation, and the need for authenticity.

[04:00] Why community matters more than ever

Rodric and Colin talk about how AI may make entrepreneurship even lonelier — and why real community will become even more valuable.

[05:00] What’s next for Colin

Colin shares why he is focused on growing the current businesses while staying open to future opportunities.

[05:00] What Rainmaker actually does

Colin explains how Rainmaker helps founders, coaches, and sales leaders use LinkedIn to grow relationships, leads, and sales.

[06:00] Colin’s philosophy for LinkedIn growth

He outlines the three layers of his strategy: authenticity, educational mindset, and understanding what your audience wants to learn from you.

[08:00] How he identifies the right audience

Colin explains how he uses Sales Navigator and ICP-based targeting to define who to connect with.

[09:00] Why first connections matter

He shares why his team reaches out to around 100 people a week and why growing a first-degree network is foundational.

[10:00] The three campaign types he uses

Colin walks through the main campaign formats he uses: drip messaging, LinkedIn polls, and live streams.

[11:00] Why LinkedIn live streams are the biggest opportunity

He explains why live streams are powerful, why LinkedIn is leaning into them, and why they cut through AI-driven sameness.

[12:00] How Colin structures live streams

Colin shares how he chooses a specific audience and a repeatable 101-level topic that can be taught over and over again.

[14:00] Why repetition works better than constant reinvention

He explains why repeating great content to the right audience is smarter than always creating something new.

[14:00] How LinkedIn event invites do the heavy lifting

Colin shares how LinkedIn’s event system helps drive awareness, reminders, and attendance without feeling spammy.

[16:00] The real power of the follow-up

After each live stream, Colin follows up with attendees in a thoughtful way that opens the door for natural next-step conversations.

[18:00] How live streams build long-term trust

Colin explains how repeated educational live streams create awareness, thought leadership, and referral momentum over time.

[20:00] Where to find Colin

He shares where people can connect with him, download his live stream resource, and learn more.

[21:00] Colin’s question for the next guest

Colin asks the next guest what book most helped them implement growth and strategy in their business.

[21:00] The question Colin was asked

Colin reflects on the importance of turning inward and trying to stay true to who he is.

Notable Quotes

“Nobody wants to be sold on LinkedIn.” – Colin Herdman

“What is it that they can learn from me? What can I teach?” – Colin Herdman

“The real opportunity is on LinkedIn when you know what your audience can learn from you.” – Colin Herdman

“It’s all about authenticity. It’s all about education. It’s all about you.” – Colin Herdman

“You don’t have to keep creating new content all the time.” – Colin Herdman

“What happens over time is you become top of mind for whatever topics you continually present on.” – Colin Herdman

“It’s all about sending the elevator back down.” – Rodric Lenhart

Connect with Colin

🌐 Website

🌍 https://rainmakergrows.com

💼 LinkedIn

🔗 https://www.linkedin.com/in/colinhirdman

Connect with Rodric

🎙 Million Dollar Flip Flops Podcast

📖 Book: Million Dollar Flip Flops

📖 Book: The Magnet, Method & Machine

🌍 Foundation: Send a Student Leader Abroad (SASLA)

If this episode made you think differently about LinkedIn, digital marketing, or how to build trust in an AI-heavy world, share it with someone who needs to hear it.

Resources:

Million Dollar Flip Flops

Ready to transform your business and your life while making a difference? Grab your copy of *Million Dollar Flip Flops*—the ultimate guide to creating a life and business that feels just as good as it looks. And here’s the best part: 100% of the proceeds go directly to our foundation, Send a Student Leader Abroad, with a goal of sending 1,000,000 deserving kids on life-changing trips around the world.

As a thank you for your support, we’re offering exclusive bonuses available only for our podcast listeners. These bonuses are packed with extra tools and resources to help you implement the principles from the book faster and more effectively.

Don’t miss this opportunity to gain invaluable insights, impact a young leader’s life, and be a part of something bigger.

Click the link, order your copy, and claim your listener-only bonuses today!

Together, let’s change lives—one trip at a time.

www.MillionDollarFlipFlops.com/book

**P.S.** Every book you buy gets us one step closer to sending 1,000,000 kids on life-changing adventures. Let’s make it happen!

190| LinkedIn, Live Streams, and Building Real Relationships in an AI World with Colin Herdman