The 10 Best Digital Mentors You Can Find
They're the ones that helped me
Welcome back to Unfollow the Herd! If you’re new here, join 4,970+ subscribers learning actionable ways to build their wealth with real estate.
“You’re the average of the 5 people you spend the most time around.”
Have you ever heard that idea?
When I hear people say this, I think a lot of people assume it means the 5 people you’re closest to. But think about life in 2025. With podcasts, social media, and audiobooks, it’s common that at least a few of those 5 people are people you’ve never met.
In fact, many of my greatest mentors never even knew they were teaching me.
I know we said “5 people,” but I don’t want everyone stealing all my mentors…
So here are the 10 best podcasts that shaped my entrepreneurial journey and helped me build my wealth:
1. "How I Built This" with Guy Raz
In entrepreneurship, you really never know what you’re doing. Guy Raz's interviews with other entrepreneurs showed me I wasn't alone. His guests share raw stories of their struggles and successes.
One quote that stuck with me from How I Built this: "The one trait that all successful entrepreneurs have in common is the ability to withstand pain."
That’s a good reminder when you’re stuck pouring concrete in the cold in North Dakota.
2. Tim Ferriss Show
Cliche? Maybe. Legitimately helpful? Yes.
Tim's ability to break down success into actionable steps changed how I approached business growth. His interviews go beyond surface-level success stories and dig into the real mechanics of building something great.
One of my favorite takeaways:
“What we fear doing most is usually what we most need to do.”
(P.S. His Jamie Foxx interview is a great one to start with.)
3. Smart Passive Income with Pat Flynn
Pat Flynn's practical approach to building online businesses gave me ideas for scaling beyond physical real estate. LinkedIn has been a game-changer for me, and by extension, so has the rest of my social media presence.
Flynn: "Entrepreneurship is living a few years of your life like most won't, so you can spend the rest like most can't."
Anyone who tells you entrepreneurship or passive income is easy is lying to you.
Anyone who tells you they aren’t worth it is also lying to you.
4. Masters of Scale with Reid Hoffman
Speaking of LinkedIn…
As someone who scaled from one employee to over 50, Reid's insights are gold.
One of my favorite notes from Hoffman:
"The most important thing an entrepreneur can do is learn to let go."
I’ve talked multiple times about how the most important thing for unlocking our growth at MAK Capital and MAK Construction was being able to stop micromanaging and start trusting my people. You have to get out of the day-to-day if you ever want to scale.
5. School of Greatness with Lewis Howes
Howes's interviews on personal development helped shape how I approach leadership. Howes: "You were born to do more than just pay bills and die."
It’s a good reminder for me. As business owners, I think a lot of us are always chasing more, more, more. When a lot of the time, we should be focusing on less, less, less.
The Brené Brown episode is the most-shared of Howes’s podcast. Worth your time.
6. HBR IdeaCast
Running multiple companies requires constant learning about leadership. The HBR IdeaCast interviews business minds from all across the spectrum, and helps CEOs/founders understand what makes a great leader from both an EQ and an IQ perspective.
7. The Indie Hackers Podcast
Courtland Allen's interviews with side-hustlers taught me valuable lessons about starting small. The quote "Don't be in a rush to make something huge. Start by making something small that solves a problem" mirrors my own journey from installing fans to developing multi-million dollar properties.
Start with the episode about Zapier’s Journey to $35M ARR. Great one.
8. The Side Hustle School
Chris Guillebeau's daily stories of entrepreneurs building businesses while working full-time reminded me of my early days. His mantra "The perfect time to start something never arrives" is reflective of a lot of the stuff I’ve come to realize — like launching MAK Capital in the middle of the COVID pandemic in 2020.
9. The Tony Robbins Podcast
I know, I know. But his stuff really is good.
Tony's energy and practical strategies for personal development have genuinely helped me quite a bit. I like his definition of success:
“Success is doing what you want when you want, where you want, with whom you want, as much as you want."
I still chase profit a lot, but this idea helps to dial back in on chasing freedom.
10. Huberman Lab
It wouldn’t be a podcast list without Huberman, right? Understanding the science behind stress and performance has been helpful in both my personal and business lives.
My advice? Don't just listen passively. Take notes. Apply what you learn. Test different strategies in your business. These podcasts are like having a board of advisors in your pocket — but only if you actually use their advice.
Remember that quote from "How I Built This" about withstanding pain? That's what building real wealth takes — the ability to push through discomfort, learn continuously, and take action even when you're scared.