Episode 22 of The Circle Investor Podcast features Grant Reigner, real estate investor, entrepreneur, and owner of Peak 3 Properties, sharing how he built a scalable real estate business by combining operational experience, strategic partnerships, and a focus on long-term lifestyle design.

He shares how he went from a single-family rental to scaling into duplexes, and ultimately making the leap into commercial multifamily, including closing on a 41-unit apartment complex through creative deal structuring and partnerships.

This conversation also explores a deeper theme: how experience eliminates fear and unlocks opportunity. He also emphasizes the importance of team building in commercial real estate, showing how the right partnerships not only improve returns, but make the journey more sustainable and fulfilling.

EPISODE HIGHLIGHTS:

• Grant’s transition from tech and construction into real estate investing.

• How early hands-on experience gave him an edge in evaluating deals.

• Why fear in real estate often comes from lack of knowledge.

• Turning a single-family rental into a scalable investment strategy.

• The shift from residential to commercial multifamily investing.

• How Grant closed on a 41-unit apartment complex using creative financing.

• Breaking down seller financing and reducing capital needed to close.

• Why every commercial deal requires a strong, aligned team.

• How to structure partnerships and equity in multifamily deals.

• The importance of networking and mastermind groups for growth.

• Why chasing lifestyle and freedom can be more powerful than chasing money.

• How collaboration and community can transform the real estate experience.

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 = [email protected]  

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

Episode 21 of The Circle Investor Podcast features Steph Weber, entrepreneur, branding expert, and short-term rental investor, sharing her journey of building multiple businesses while designing a life centered around freedom, family, and intentional living.

From starting as a fashion and travel influencer to founding a branding and marketing agency, Steph walks through the pivots that shaped her career and ultimately led her into the world of short-term rentals. She opens up about scaling a co-hosting business to six figures within a year, launching a cabin development project in Kentucky, and building a brand in a competitive and evolving market.

This conversation also dives into a bigger question: what are you really building your business for? Steph shares the mindset shift that led her and her family to pursue a year of nomadic living, eventually trading routine for adventure and redefining success beyond revenue goals.

EPISODE HIGHLIGHTS:

• Steph’s transition from influencer to branding agency owner and entrepreneur.

• How she scaled a short-term rental co-hosting business to six figures in 12 months.

• The story behind launching a multi-cabin development project in Kentucky.

• Lessons from taking action without having all the answers in real estate investing.

• Why guest experience is the key to standing out in the short-term rental market.

• How design, branding, and amenities directly impact revenue and bookings.

• The realities of managing short-term rentals and becoming a top-performing property.

• Shifting from chasing revenue goals to building a lifestyle-driven business.

• Why Steph and her family chose to pursue a year of nomadic living.

• Balancing entrepreneurship, family life, and long-term vision.

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 = [email protected]  

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

Episode 20 of The Circle Investor Podcast features Jake Handley, a rising real estate agent with the Live Indy Team at eXp Realty, to break down what it really looks like to build a career in real estate from scratch. Just two years into the industry, Jake shares how he went from having zero experience to becoming part of a rapidly growing team closing tens of millions in volume.

This conversation dives into the realities of starting young in real estate, learning through trial and error, and finding your niche in a competitive market. From working with first-time home buyers to navigating investor deals and “creepy basement” properties, Jake gives an unfiltered look into the day-to-day life of an agent. He also shares insights on the importance of education, client relationships, and being part of a team that accelerates growth.

Whether you're considering real estate as a career, investing in property, or buying your first home, this episode offers practical lessons and relatable experiences from someone in the trenches.

EPISODE HIGHLIGHTS:

• Jake’s journey into real estate and transitioning from a corporate job to full-time agent.

• What it’s like starting with zero experience and landing your first deal.

• The key differences between working with investors vs. first-time home buyers.

• Why education is crucial when guiding first-time buyers through the process.

• Common misconceptions about affordability, down payments, and closing costs.

• The value of joining a real estate team vs. going solo early in your career.

• How to find your niche and build a client base in a competitive market.

• Real stories from the field—including unpredictable showings and challenging properties.

• Lessons on growth, consistency, and building a sustainable real estate business.

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 = [email protected]  

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 investors think finding a “good deal” is about the price but the real difference comes down to how well you analyze it. Without a clear and consistent approach to deal analysis, it’s easy to overestimate returns, miss key expenses, or get stuck in analysis paralysis.

This course walks you through the fundamentals of analyzing real estate deals using a practical, repeatable system. From understanding rent comps and estimating expenses to calculating cash flow, cap rate, and cash-on-cash return, you’ll learn how to evaluate opportunities with confidence. More importantly, you’ll learn how to stay consistent in your analysis so you can quickly recognize what actually makes a deal worth pursuing.

Whether you’re buying your first investment property or looking to scale, this course helps you focus on what matters—so you can make decisions based on real numbers, not guesswork.

COURSE HIGHLIGHTS:

• Why consistent deal analysis matters more than perfect accuracy.

• How to evaluate properties using a simple, repeatable framework.

• The key metrics every investor should understand (cash flow, cap rate, cash-on-cash return).

• How to estimate rent using comps and avoid overpricing assumptions.

• Common expenses investors forget—and how they impact your returns.

• The importance of accounting for taxes, insurance, and vacancy.

• How to avoid analysis paralysis and confidently move on a solid deal.

• Why running multiple deal analyses helps you recognize strong opportunities faster.

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) delivers practical, structured, and experience-driven insights designed to help aspiring or seasoned investors and other real estate participants to thrive in this industry. This series of training courses focuses on real estate investing, property management, and small business operations. While grounded in the Central Indiana real estate market, the principles shared extend beyond the Hoosier state, staying true to the goal of equipping listeners and learners with actionable guidance and real-world insights they can apply immediately.

Indianapolis Investor Map:

https://earth.google.com/web/@39.82822064,-86.23642807,244.55852422a,143828.53126734d,35y,0h,0t,0r/data=CgRCAggBMikKJwolCiExMXo0Um9JalJtZk5IOHVYd0dvTXpDZ1hlNDZJbDRIU20gAjoDCgEwQgIIAEoICNqbm6sBEAE?_pxl=djoxLGM6YmZjZGJhMzg2MTY0MzAsYTox&authuser=0  

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

Gmail = [email protected] 

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

Episode 19 of The Circle Investor Podcast features Phil Hipskind, founder of Genia, to explore the intersection of scientific innovation, entrepreneurship, and building a business from the ground up. With over 30 years of experience as a research scientist at Eli Lilly and Company, Phil shares how his transition from corporate science to leading a grant-funded biotech company was anything but traditional.

This conversation goes beyond the surface of biotech and dives into the realities of starting a company without a business background, navigating funding through organizations like the Bill & Melinda Gates Foundation, and building a lean, highly specialized team. From early-stage drug discovery to leveraging AI in modern research, Phil offers a rare look into the systems, risks, and decisions that shape innovation in global health. Whether you're an entrepreneur, investor, or simply curious about how groundbreaking science gets off the ground, this episode delivers valuable insights from someone operating at the cutting edge.

EPISODE HIGHLIGHTS:

• The difference between biotech and research science (and why Genia operates as a hybrid model).

• How Phil transitioned from a 30+ year career at Eli Lilly and Company into entrepreneurship.

• The role of the Bill & Melinda Gates Foundation in funding high-risk, high-impact global health initiatives.

• Building a company from scratch without prior business experience.

• Why Indiana offers a strategic advantage for startups and scaling businesses.

• How Genia contributes to treatments for diseases like tuberculosis, malaria, and Alzheimer’s.

• The growing impact of AI and machine learning in drug discovery.

• Lessons on leadership, risk-taking, and building a mission-driven team.

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 = [email protected]  

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 investors think finding a “good deal” is about the price but the real difference comes down to how well you analyze it. Without a clear and consistent approach to deal analysis, it’s easy to overestimate returns, miss key expenses, or get stuck in analysis paralysis.

This course walks you through the fundamentals of analyzing real estate deals using a practical, repeatable system. From understanding rent comps and estimating expenses to calculating cash flow, cap rate, and cash-on-cash return, you’ll learn how to evaluate opportunities with confidence. More importantly, you’ll learn how to stay consistent in your analysis so you can quickly recognize what actually makes a deal worth pursuing.

Whether you’re buying your first investment property or looking to scale, this course helps you focus on what matters—so you can make decisions based on real numbers, not guesswork.

COURSE HIGHLIGHTS:

• Why consistent deal analysis matters more than perfect accuracy.

• How to evaluate properties using a simple, repeatable framework.

• The key metrics every investor should understand (cash flow, cap rate, cash-on-cash return).

• How to estimate rent using comps and avoid overpricing assumptions.

• Common expenses investors forget—and how they impact your returns.

• The importance of accounting for taxes, insurance, and vacancy.

• How to avoid analysis paralysis and confidently move on a solid deal.

• Why running multiple deal analyses helps you recognize strong opportunities faster.

  
  

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) delivers practical, structured, and experience-driven insights designed to help aspiring or seasoned investors and other real estate participants to thrive in this industry. This series of training courses focuses on real estate investing, property management, and small business operations. While grounded in the Central Indiana real estate market, the principles shared extend beyond the Hoosier state, staying true to the goal of equipping listeners and learners with actionable guidance and real-world insights they can apply immediately.

Indianapolis Investor Map:

https://earth.google.com/web/@39.82822064,-86.23642807,244.55852422a,143828.53126734d,35y,0h,0t,0r/data=CgRCAggBMikKJwolCiExMXo0Um9JalJtZk5IOHVYd0dvTXpDZ1hlNDZJbDRIU20gAjoDCgEwQgIIAEoICNqbm6sBEAE?_pxl=djoxLGM6YmZjZGJhMzg2MTY0MzAsYTox&authuser=0  

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

Gmail = [email protected] 

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

Episode 19 of The Circle Investor Podcast features Phil Hipskind, founder of Genia, to explore the intersection of scientific innovation, entrepreneurship, and building a business from the ground up. With over 30 years of experience as a research scientist at Eli Lilly and Company, Phil shares how his transition from corporate science to leading a grant-funded biotech company was anything but traditional.

This conversation goes beyond the surface of biotech and dives into the realities of starting a company without a business background, navigating funding through organizations like the Bill & Melinda Gates Foundation, and building a lean, highly specialized team. From early-stage drug discovery to leveraging AI in modern research, Phil offers a rare look into the systems, risks, and decisions that shape innovation in global health. Whether you're an entrepreneur, investor, or simply curious about how groundbreaking science gets off the ground, this episode delivers valuable insights from someone operating at the cutting edge.

EPISODE HIGHLIGHTS:

• The difference between biotech and research science (and why Genia operates as a hybrid model).

• How Phil transitioned from a 30+ year career at Eli Lilly and Company into entrepreneurship.

• The role of the Bill & Melinda Gates Foundation in funding high-risk, high-impact global health initiatives.

• Building a company from scratch without prior business experience.

• Why Indiana offers a strategic advantage for startups and scaling businesses.

• How Genia contributes to treatments for diseases like tuberculosis, malaria, and Alzheimer’s.

• The growing impact of AI and machine learning in drug discovery.

• Lessons on leadership, risk-taking, and building a mission-driven team.

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 = [email protected]  

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 investors obsess over buying the right deal but overlook the one decision that actually determines long-term returns: the property manager. From tenant placement to maintenance and reporting, the wrong manager can quietly drain your profits, while the right one protects and grows them.

This course also breaks down how different property types and locations require different management approaches, and why not every manager is suited for every asset. If you’re investing out of state or planning to scale, knowing how to properly evaluate and work with a property manager is key to making your investments actually perform (not just look good on paper).

COURSE HIGHLIGHTS:

• Why your property manager has a direct impact on your investment performance.

• The operational responsibilities that influence returns beyond the numbers.

• How tenant quality, turnover, and maintenance are tied to management quality.

• Why not all property managers are equipped for every type of asset.

• The risks of poor communication and lack of transparency.

• How management decisions can increase or reduce vacancy and expenses.

• What to look for when choosing a property management partner.

• Why alignment between investor goals and manager execution matters.

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) delivers practical, structured, and experience-driven insights designed to help aspiring or seasoned investors and other real estate participants to thrive in this industry. This series of training courses focuses on real estate investing, property management, and small business operations. While grounded in the Central Indiana real estate market, the principles shared extend beyond the Hoosier state, staying true to the goal of equipping listeners and learners with actionable guidance and real-world insights they can apply immediately.

Indianapolis Investor Map:

https://earth.google.com/web/@39.82822064,-86.23642807,244.55852422a,143828.53126734d,35y,0h,0t,0r/data=CgRCAggBMikKJwolCiExMXo0Um9JalJtZk5IOHVYd0dvTXpDZ1hlNDZJbDRIU20gAjoDCgEwQgIIAEoICNqbm6sBEAE?_pxl=djoxLGM6YmZjZGJhMzg2MTY0MzAsYTox&authuser=0  

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

Gmail = [email protected] 

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

In this episode of The Circle Investor Podcast, we sit down with Anthony Strunz from Hawk Operations to unpack the operational and financial side of running a successful property management business. While many conversations in real estate focus on acquisitions and deals, this discussion goes deeper into the systems, accounting discipline, and operational infrastructure that actually allow real estate companies to scale sustainably.

From the challenges of managing complex portfolios to the importance of aligning financial strategy with day-to-day operations, this conversation highlights the less visible, but extremely important, mechanics that keep real estate businesses running effectively. If you're building a property management company, scaling an investment portfolio, or simply trying to understand how strong operational foundations support long-term growth, this episode offers practical insights from the people working behind the numbers.

EPISODE HIGHLIGHTS:

• Why operational systems are critical to scaling a property management business.

• The role accounting and financial reporting play in long-term real estate success.

• Why no two property management companies operate the same way.

• How advisors help operators navigate financial and operational decisions.

• The balance between standardization and customization in growing businesses.

• Why transparency and strong reporting build trust with owners and investors.

• The hidden operational challenges most real estate investors never see.

• How strong financial infrastructure supports sustainable growth.

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.

If you’ve ever sold an investment property and felt the sting of capital gains taxes, this course explains how a 1031 exchange allows you to legally defer those taxes and keep more of your capital working for you in real estate.

We walk through what a 1031 exchange actually is (and what it isn’t), how it works in real-world investing scenarios, and why understanding the rules, timelines, and risks is critical before you ever list a property for sale. From upgrading asset quality and consolidating portfolios to relocating investments across markets, this episode explores how experienced investors use 1031 exchanges to compound growth over time and where newer investors often get tripped up.

This is educational content, not tax advice, but if you’re serious about long-term portfolio growth, asset repositioning, and keeping momentum without unnecessary tax drag, this course provides the foundational understanding you need before making your next move.

COURSE HIGHLIGHTS:

• What a 1031 exchange actually does (tax deferral vs. tax avoidance)

• When a 1031 exchange applies and when it doesn’t

• Why like-kind exchanges must involve investment properties

• How investors use 1031s to trade up, downsize, or reposition assets

• The compounding power of executing multiple exchanges over time

• Critical timelines: the 45-day identification rule and 180-day close window

• The role of a qualified intermediary and why DIY doesn’t work

• Common mistakes that derail exchanges before they start

• Situations where a 1031 exchange may not make financial sense

• Why planning ahead and assembling the right team is essential

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) delivers practical, structured, and experience-driven insights designed to help aspiring or seasoned investors and other real estate participants to thrive in this industry. This series of training courses focuses on real estate investing, property management, and small business operations. While grounded in the Central Indiana real estate market, the principles shared extend beyond the Hoosier state, staying true to the goal of equipping listeners and learners with actionable guidance and real-world insights they can apply immediately.