Most people are attracted to real estate for the freedom. Few are prepared for what it actually demands.

In this episode of The Circle Investor Podcast, we sit down with Scott Chain to talk about entrepreneurship, long-term commitment, and the realities of building a business in a commission-based industry. From navigating inconsistent income and pressure-filled seasons to developing the discipline and mindset required to stay in the game, this conversation unpacks what separates those who last from those who burn out. If you’re serious about ownership, sustainability, and creating a career on your terms, this episode delivers the honest perspective most people don’t hear when they first get started.

EPISODE HIGHLIGHTS:

• Why freedom in real estate comes with responsibility

• The mental shift required to survive commission-based income

• What most new agents underestimate about entrepreneurship

• The difference between short-term wins and long-term careers

• Why commitment — not motivation — determines longevity

• How building resilience impacts financial outcomes

  
  

Make sure you’re locked in for next week’s episode! We’re keeping the momentum going with more insights, real stories, and strategies to help you build your real estate business. Hit subscribe, tap the notification bell, and don’t miss what’s coming next.

The Circle's Founder (Ryan Rominger) and Director of Operations (Stuart Smith) discuss what’s happening in the world of Real Estate Investing, Property Management, and running a small business based in Indianapolis. The show focuses on the Central Indiana real estate market, but also explores beyond the Hoosier state to gain intriguing insights in the world of business and real estate investing. We interview our favorite influential people from across Central Indiana (and beyond) to learn from the people having the biggest impact on our market.

Do you have any questions, suggestions, or simply want to reach out? Contact us through this email address:

Gmail = circleinvestorpod@gmail.com

Follow us on all of our socials:

Facebook = www.facebook.com/thecircleinvestor/

Instagram = www.instagram.com/thecircleinvestor/

You can also check our our website for more information:

Website = www.intriguepm.com

Upcoming Investor Meetups = www.intriguepm.com/thecircleindy

Most people don’t fail in real estate because of lack of ambition—they fail because they underestimate the discipline it takes to stay consistent long enough to win.

In this episode of The Circle Investor Podcast, we sit down with Darien Sharpe for an honest conversation about ambition, work ethic, and what it actually looks like to build momentum in real estate from the ground up. From early career pressure and social media expectations to the unglamorous daily habits behind growth, Darien breaks down how mindset, consistency, and long-term thinking separate professionals who last from those who burn out. This episode dives into the gap between where most people say they want to go and what they’re actually willing to do to get there and why clarity, patience, and self-awareness matter more than hype.

EPISODE HIGHLIGHTS:

• Why ambition without discipline leads to frustration

• The pressure young professionals face in performance-driven industries

• How social media distorts expectations around success

• The importance of consistency over short-term wins

• What early-career growth really looks like behind the scenes

• Why patience and long-term vision matter more than fast results

Make sure you’re locked in for next week’s episode! We’re keeping the momentum going with more insights, real stories, and strategies to help you build your real estate business. Hit subscribe, tap the notification bell, and don’t miss what’s coming next.

The Circle's Founder (Ryan Rominger) and Director of Operations (Stuart Smith) discuss what’s happening in the world of Real Estate Investing, Property Management, and running a small business based in Indianapolis. The show focuses on the Central Indiana real estate market, but also explores beyond the Hoosier state to gain intriguing insights in the world of business and real estate investing. We interview our favorite influential people from across Central Indiana (and beyond) to learn from the people having the biggest impact on our market.

Do you have any questions, suggestions, or simply want to reach out? Contact us through this email address:

Gmail = circleinvestorpod@gmail.com

Follow us on all of our socials:

Facebook = www.facebook.com/thecircleinvestor/

Instagram = www.instagram.com/thecircleinvestor/

You can also check our our website for more information:

Website = www.intriguepm.com

Upcoming Investor Meetups = www.intriguepm.com/thecircleindy

Most real estate mistakes don’t happen at purchase, they happen in how the property is managed after closing.

In this episode of The Circle Investor Podcast, we sit down with David Brinkworth to talk through the unfiltered realities of property management, investor decision-making, and why speed, oversight, and alignment matter more than most owners realize. From costly delays and maintenance bottlenecks to the difference between institutional ownership and hands-on investing, this conversation breaks down how small decisions compound into real financial consequences. If you’re focused on protecting cash flow, minimizing risk, and running your portfolio like a business—not a hobby—this episode pulls back the curtain on what actually moves the needle.

EPISODE HIGHLIGHTS:

• Why slow decisions can quietly destroy cash flow

• The real cost of vacancies, deferred maintenance, and approval delays

• How hands-on oversight separates private investors from institutions

• Why urgency isn’t emotional—it’s financial

• The operational differences between small portfolios and large hedge funds

• What investors often misunderstand about day-to-day property management

Make sure you’re locked in for next week’s episode! We’re keeping the momentum going with more insights, real stories, and strategies to help you build your real estate business. Hit subscribe, tap the notification bell, and don’t miss what’s coming next.

The Circle's Founder (Ryan Rominger) and Director of Operations (Stuart Smith) discuss what’s happening in the world of Real Estate Investing, Property Management, and running a small business based in Indianapolis. The show focuses on the Central Indiana real estate market, but also explores beyond the Hoosier state to gain intriguing insights in the world of business and real estate investing. We interview our favorite influential people from across Central Indiana (and beyond) to learn from the people having the biggest impact on our market.

Do you have any questions, suggestions, or simply want to reach out? Contact us through this email address:

Gmail = circleinvestorpod@gmail.com

Follow us on all of our socials:

Facebook = www.facebook.com/thecircleinvestor/

Instagram = www.instagram.com/thecircleinvestor/

You can also check our our website for more information:

Website = www.intriguepm.com

Upcoming Investor Meetups = www.intriguepm.com/thecircleindy