BLOG

#67 - Founding Companies and Finding Yourself with Griff O’Brien

Sep 10, 2024

MORE ON THIS EPISODE

CEO of Estate Media Griff O’Brien is here to share his journey of becoming CEO at 29, his story of finding sobriety at 21, and his advice for finding confidence in your career.

From College Entrepreneur to Celebrity Real Estate: The Raw Truth About Building Companies in Your 20s

How one guy went from starting his first company at 20 to building a multi-million dollar media empire—and overcame addiction along the way

What if I told you that the path to entrepreneurial success involves getting sober at 21, dropping out of college, and completely changing industries? That's exactly what happened to Griff O'Brien, who built his first company as a college sophomore and is now the CEO of a thriving real estate media company.

This isn't your typical "college dropout becomes billionaire" story. It's much more real than that.

Starting a Company at 20 (When You Know Nothing About Business)

Griff's entrepreneurial journey began at Wake Forest University, where he had an idea that seems obvious in hindsight but was revolutionary at the time: help people cut the cord from expensive cable subscriptions.

The problem he identified: People were paying $140/month for cable but only watching 3-5 channels. Streaming services were emerging, but nobody knew how to navigate them.

His solution: Create a recommendation system where users could input what they wanted to watch, and the platform would suggest the cheapest bundle of streaming services to get everything.

The execution: With just his intern wages ($10/hour), Griff found two developers on Upwork and built an MVP. Through his internship connections, he secured affiliate deals with HBO, Stars, and Sling TV.

The result: He managed to exit the company, though he admits: "When I look back, comparing it to my company now, I knew nothing about business. I didn't really know how this would scale, how much money it would take to build, how much money we could actually make."

The Addiction Reality That Nobody Talks About

Here's where Griff's story takes a turn that most entrepreneurs never discuss publicly. Despite appearing successful—running a company while maintaining strong grades—he was struggling with substance abuse.

His realization: "While I was strong academically and starting my company, I fell into the trap that a lot of young people do of developing very unhealthy relationships with substances."

The family pattern: "I come from a family where almost everyone either died from alcoholism or is currently dealing with it or got sober."

The decision: After his junior year, Griff made one of the hardest choices of his life—he left school to get sober at 21.

The Year That Changed Everything

Instead of hiding his struggles, Griff took a full year off to focus on recovery:

Attended a treatment facility
Built a community of sober peers
Worked with mentors in recovery
Learned to be "brutally honest" with himself

His insight: "When you go through something like that, you get sober, you're dealing with addiction, you have to grow up pretty quickly and encounter those things and really do deep work on yourself that I believe has given me an incredible leg up both in my personal life, but also professionally."

Breaking the Stigma in Professional Settings

What's remarkable about Griff's story is his openness about addiction in the business world. When he got sober in 2017, the stigma was even greater than today.

His advice for others struggling:

Find support immediately - "All it takes really is a Google search and you'll find really in any city that there are probably 50 different types of recovery meetings"
Build community - "Finding other people who are in the same position and just reaching out to your network"
Be honest with close people - "When your close people know and are there to support you, it makes going out, it makes doing all of these things way easier"

The Power of Mentorship (And How to Get It)

One of Griff's biggest advantages was securing high-level mentors early. His approach was systematic:

How he found mentors:

Started networking in high school (reached out to his friend's dad who was a Fortune 500 CEO)
Used LinkedIn extensively throughout college
Focused on preparation: "I would sit there and do a ton of preparation, read all the articles these people had been in"

His networking philosophy:

"When you are young, people are willing to talk to you"
"Most people are open to talking to someone early in their career"
"Don't be discouraged—most people do not respond, but it really takes one person to buy in"

From Big Tech to Media Empire

After getting sober and graduating, Griff worked at major companies including Snapchat, Roku, and Amazon Prime Video. This wasn't just resume building—it was strategic learning.

What he learned from big companies:

Management styles that work (and don't work)
The importance of honesty in leadership
How to balance performance culture with empathy
The value of leading by example

Finding His Next Big Idea

While at Amazon, Griff discovered a gap in real estate content. Through his network, he met real estate professionals who were spending money on content but not treating it as valuable intellectual property.

The opportunity he saw:

Real estate agents were paying for content creation but not monetizing it
Content was either sensationalized reality TV or boring trade publications
No one was making real estate content that was both educational and entertaining

The solution: Create a media company featuring top real estate personalities, producing content that agents actually want to consume.

Building Estate Media: The Results

In less than a year, Griff's company achieved remarkable growth:

3 podcasts (among the top 5 real estate podcasts in the US)
6 newsletters with 120,000+ readers (70% real estate agents)
270,000+ social media followers
Total audience of 330,000 across all channels

Revenue model:

Advertising from real estate platforms, tech companies, luxury brands
Sponsored content and custom integrations
Upcoming membership community with top real estate personalities

The Leadership Lessons

As a 29-year-old CEO managing 12 employees, Griff has learned crucial lessons about leadership:

What makes a good leader:

Honesty about company culture - "Be very clear about what your culture is and don't try to have this great place to work if realistically it's a very performance-driven cutthroat environment"
Leading by example - "If you're there busting your ass and delivering results and people see that from you, I think it inspires others"
Balancing empathy with performance - Finding the "delicate balance between being empathetic and making sure you set a very high standard"

Advice for Young Entrepreneurs

Griff's top recommendations:

1. Get Incredible Mentors Early

"Network early and just being young, you're going to get access to opportunities."

2. Find Your Unique Value

"Find what value you can provide, especially to executives at a company and make them look smart."

3. Cross-Industry Knowledge Transfer

"Take whatever expertise you have and find an industry with people that have a complete knowledge gap in terms of what you know."

4. Do Your Research

"Do a lot of research on a company before you join. Talk to people who work there, talk to people who work for the boss you're going to work for."

5. Trust Your Gut

"Trust your gut and trust your intuition" when something seems off about an opportunity.

The Biggest Challenges of Entrepreneurship

Work-life balance: "It's easier almost to just be fully heads down... At the same time, I have a life. I'm married, I have horses, I have other passions."

Scaling skills: "The skillset of building, launching a company, raising money to scaling... it's a very different skillset than being a solo operator."

Building teams: Learning to create "systems and processes that work well" as the company grows.

What He'd Tell His 20-Year-Old Self

"Put yourself in uncomfortable positions and be okay with the difficulty that's going to come from that... Having a high risk appetite early in your career, especially if you want to accelerate quickly."

The Reality Behind Success Stories

Griff's journey destroys the myth of the smooth entrepreneurial path. Real success often involves:

Overcoming personal demons
Taking breaks to focus on health
Learning from failures and setbacks
Being vulnerable about struggles
Building genuine relationships and mentorships

His story proves that you don't need to have everything figured out at 20. You need courage to start, honesty to face your problems, and persistence to keep building—even when the path gets complicated.

The bottom line: Success isn't about avoiding difficulties. It's about how you handle them, learn from them, and use them to become a better leader and person.

Want to hear the full conversation? This post is based on Josh's complete interview with Griff O'Brien on the Guyset podcast. Listen to the full episode on Spotify, Apple Podcasts, or wherever you listen to podcasts for more insights on entrepreneurship, recovery, and building businesses in your twenties.

Struggling with your own challenges while trying to build something? Remember that vulnerability and honesty often lead to the greatest breakthroughs—both personally and professionally.

Related Topics: