Starting With $1K: Military Discipline, Investing Smarts & Defining a Rich Life with Darren Ick

In this episode of the ADPI Podcast, host Markian Sich sits down with Air Force veteran and long-time investor Darren Thedieck, who shares how he built financial freedom starting with just $1,000 and a Roth IRA. Darren opens up about his humble beginnings, growing up in a split household, and the financial lessons he learned watching his mother struggle to make ends meet.

Through discipline, delayed gratification, and a passion for personal finance, Darren carved his path—not with real estate—but with intentional investing, strategic budgeting, and the powerful philosophy of “paying yourself first.”

From traveling to over 50 countries to building wealth while stationed overseas, Darren’s journey proves you don’t need a VA loan or fancy portfolio to win. His story is packed with mindset gems, savings strategies, and lessons on defining a “rich life” that’s about memories—not just money.

Whether you’re just starting out or looking to dial in your focus, this episode is a must-listen for any service member ready to take control of their financial future.

Episode Breakdown:

00:00 – Introduction & Guest Announcement

00:58 – Darren’s Background & Humble Beginnings

02:45 – Early Lessons in Money, Bloomberg & Budgeting

06:18 – Military Service, Family, and Financial Drive

08:20 – Starting with $1K: Opening a Roth IRA

10:54 – Mindset Shift: From Saving to Serious Investing

13:15 – Traveling the World While Building Wealth

16:47 – FIRE Movement & Financial Independence Goals

19:08 – Pay Yourself First: Budgeting with Intention

22:13 – Marriage, Compromise, and Shared Financial Vision

25:36 – Investing Psychology: Let Your Winners Ride

27:42 – Stocks vs. Real Estate: Finding Your Investment Identity

31:09 – Discipline Over Motivation: Sticking to the Plan

33:51 – How Darren Defines a “Rich Life”

37:05 – Advice to Young Service Members: Believe in Yourself

39:24 – Final Thoughts, Darren’s Community, and How to Connect

Connect with Darren:

Facebook Group: Financial Dream to Reality

https://www.facebook.com/groups/financialdreamtoreality

Facebook Page: AchieveFI

https://www.facebook.com/AchieveFI/

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From Marine Raider to ADU Builder: Finding Freedom, Purpose, and a New Mission with Mark Brookman

In this powerful episode, Markian sits down with Marine Corps veteran and real estate investor Mark Brookman to unpack the part of the military story most people never see—the invisible battles after the uniform comes off. Mark shares how micro–traumas from Afghanistan and Iraq slowly piled up, what it felt like to “look fine” on paper but be mentally spiraling, and why so many veterans struggle with purpose once the mission ends.

From losing $50K on his first flip to building high-margin ADU projects in Seattle, Mark walks through how real estate became the bridge from warfighter to present father, husband, and entrepreneur. Together, he and Markian dig into mindset, anxiety, balance, and why financial freedom is less about Ferraris and more about having time to enjoy what’s free—family, community, and impact. If you’re a service member, veteran, or military spouse searching for your next mission, this conversation will hit home.

In this episode, you’ll hear about:

• Why Mark joined the Marine Corps—and how his mindset shifted after deployment
• The unseen psychological toll of “micro events” and constant hypervigilance
• How Mark realized he wasn’t okay even without the stereotypical combat story
• The brutal truth of losing $50K on his first flip—and why he refused to quit
• How ADUs in expensive markets like Seattle became his path to freedom
• The difference between chasing rank/certifications vs. chasing purpose
• Why veterans are uniquely primed to succeed in real estate (with a few mindset tweaks)
• The real reason “financial freedom” matters—and what to do with it once you have it

Timestamps

00:00 Introduction and Episode Kickoff

00:35 Meeting Mark Brookman

01:59 Mark's Military Background

05:04 Deployment Stories and Challenges

09:31 Transitioning Out of the Military

22:19 Real Estate as a New Mission

45:53 Bite the Elephant: Embracing Challenges

46:41 Military Mindset in Real Estate

51:16 The Power of Focus and Discipline

52:46 Overcoming Anxiety and Adapting

56:35 Finding Purpose Beyond the Military

01:11:50 Real Estate Success Stories

01:21:45 Conclusion and Final Thoughts

Connect with Mark here:

Instagram: @SummitPointAcademy

IG: @marktbrookman

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Markian sits down with Cheyenne Wachtendorf, a new ADPI member whose path runs from military service to creative deals—live-in flips, seller finance—and a 106-acre VA loan purchase. Cheyenne shares the mindset behind taking calculated risks, learning from setbacks, and his vision for Walk Squad Haven: real estate development, experiential recreation, and community mentorship.

Time Stamps

00:00 Introduction and Conference Recap

01:30 Guest Introduction: Cheyenne Wetten

02:23 Cheyenne's Unique Real Estate Journey

06:36 Military Background and Personal Struggles

10:47 Transition from Military to Real Estate

19:12 The Importance of Mentorship and Community

49:55 Cheyenne's Vision and Future Plans

52:36 The Puzzle of Real Estate Vision

53:14 Mapping Out the Dream

53:41 Leveraging W2 Income

55:49 First Real Estate Investments

01:01:02 Facing Setbacks and Learning

01:05:05 Rebounding with New Strategies

01:11:16 The Big Vision: W Squad Haven

01:17:17 Final Thoughts and Future Plans

Key Takeaways

• Start small, build momentum: early creative wins compound into bigger plays.
• Use VA loan creatively: structure matters more than “standard.”
• Failures become playbooks: debrief, systemize, and iterate.
• Mission first: purpose makes persistence possible.

Connect with Cheyenne

WachSquad Haven on Facebook:

• https://www.facebook.com/profile.php?id=61575568000549
• Phone: 903-698-3040

💥 Want to Connect with a Community of Military Real Estate Investors?

Join ADPI Campus™—the world’s premier platform for military members and their families building wealth through real estate.

🎉 Join today: https://go.activedutypassiveincome.com/adpi-campus-join

Inside you’ll find real estate education that works, a supportive community that gets it, and the kind of camaraderie only service members can bring.

Interested in joining a MMA cohort? Book a free strategy all here: http://activedutypassiveincome.com/strategy

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If this resonated, share the episode and follow the show to help more military families build wealth through real estate.

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From ROTC to Real Estate: Landon Fillmore's Journey of Investments and Identity

In this episode, host Mark chats with Landon Fillmore, a member of the military community who has successfully navigated his way into real estate investing. Landon shares his journey from joining the ROTC in college, to buying his first fourplex property, to managing rentals while stationed overseas. They discuss the pivotal conversations, educational resources, and strategies that built Landon's confidence and propelled him into action. The episode also delves into the mechanics of managing properties remotely, leveraging the VA loan, and the power of impactful discussions within the military to promote financial literacy. Whether you're interested in investing, facing an identity shift, or looking to understand real estate's four key pillars, Landon's experiences offer valuable insights for military members and beyond.

00:00 Introduction and Guest Welcome

01:24 Landon Fillmore's Background and Military Journey

02:55 First Steps into Real Estate Investing

05:46 Discovering Real Estate Education and Influences

10:55 The Power of Confidence and Taking Action

22:25 Navigating Real Estate Challenges and Opportunities

29:27 Exploring Midterm and Corporate Rentals

39:17 Balancing Personal Goals and Real Estate Strategies

48:17 Introduction to Real Estate Tracks

48:42 Embracing Identity Shifts

49:57 Military and Real Estate: Balancing Identities

52:02 Navigating Personal Identity Crises

53:33 From Ukraine to the U.S.: A Journey of Identity

56:53 The Naval Academy Experience

01:00:07 Transitioning to Entrepreneurship

01:02:52 Real Estate Investing Insights

01:07:22 Leadership and Financial Education in the Military

01:17:43 Managing Properties Remotely

01:28:05 Conclusion and Contact Information

06:30 The Influence of Robert Kiyosaki and Pat Flynn

06:39 Discovering Passive Income and Military Community

07:12 The Journey to Real Estate Investing

01:41:10 The Importance of Confidence and Education

01:52:20 Powerful Conversations and Decision Making

01:56:24 Creative Real Estate Strategies

02:47:56 Managing Properties Remotely

02:58:13 Final Thoughts and Contact Information

Connect with Landon here:

Instagram: @LandonJFillmore

WhatsApp: +1 801-404-3709,

Email: fillmoreestate@gmail.com

🔥 Join the #1 Military Real Estate Investor Community!

Looking for expert education, live Q&As, and a network of action-takers who share your financial goals? Join ADPI Campus™ today!

🔗 Sign up now →

https://go.activedutypassiveincome.com/res-pro-podcast

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Blockchain and Real Estate: A Deep Dive with ADPI Experts

In this engaging episode of the ADPI podcast, host Tim Kelly chats with Seneca Peña Colazo about the intersection of blockchain, cryptocurrency, and real estate investing. They clarify misconceptions about crypto, likening blockchain to a highway where scams are the driver's fault, not the road's. Highlighting the permanence and transparency of blockchain, the episode dives into personal experiences and strategies for crypto investment. Seneca shares how he transitioned from a crypto skeptic to an enthusiast, while Tim recounts his journey through commercial and multifamily real estate investments. They emphasize self-custody and security practices, discuss the potential of Bitcoin as 'digital gold', and explore the growing adoption of digital currencies globally. The conversation ties back to real estate, illustrating how blockchain can revolutionize property transactions, title verifications, and investment strategies.

Episode breakdown:

00:00 Introduction to Blockchain and Crypto

01:08 Welcome to the ADPI Podcast

01:45 Guest Introductions and Backgrounds

02:57 The Intersection of Real Estate and Blockchain

05:15 Understanding Bitcoin and Blockchain Security

06:52 The Importance of Self-Custody in Crypto

08:22 Exploring Cryptocurrency Mining

13:26 Types of Cryptocurrencies: Store of Value vs. Utility

18:27 Best Practices for Crypto Storage and Security

29:02 Real Estate and Bitcoin: A Comparative Analysis

31:05 Understanding Bitcoin's Limited Supply

32:01 The Value of Bitcoin and Real Estate

34:08 Bitcoin Adoption and Institutional Investment

35:16 The Future of Bitcoin and Global Integration

36:39 Investment Strategies and Market Timing

37:30 Exploring Alternative Cryptocurrencies

45:29 Blockchain Technology in Real Estate

52:45 Practical Tips for Crypto Investment

57:09 Final Thoughts and Resources

Do you want to join a community of like-minded Military Real Estate Investors offering real estate education that actually works while celebrating camaraderie, and competition, and fostering a spirit of support?

Introducing ADPI Campus™ - the premiere platform and online space for Military Real Estate Investors worldwide! Podcast listeners JOIN ADPI CAMPUS now and get in on the action!

Helpful Resources

Connect with the ADPI: Facebook | Instagram | YouTube

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Thanks for tuning in to this week's episode of the Active Duty Passive Income Podcast! If the information shared in these weekly interviews has inspired you to pursue your dreams of financial independence, please do me a personal favor and head over to Apple Podcasts, subscribe to our show, and leave us a 5-star review.

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Uncovering Creative Financing: A Deep Dive with Adam Catledge

In this episode, we welcome Adam Catledge, a Marine Corps veteran and seasoned entrepreneur, to demystify the complexities of creative financing in real estate. Known for his profound knowledge in sub-2s and wraparound mortgages, Adam shares his journey from military service to becoming a successful real estate investor. He elaborates on his first deals, the mechanics of subject-to transactions, and how wraparound mortgages can create significant cash flow and value. Adam also introduces the concept of co-living as a lucrative exit strategy and underlines the importance of working with mentors to expedite success in creative financing. This conversation provides invaluable insights and practical advice for both novice and seasoned investors.

Episode Breakdown:

00:00 Introduction and Guest Welcome

01:24 Adam Keli's Background and Military Service

02:16 Discovering Creative Financing

07:28 First Creative Finance Deal

17:07 Understanding Subject To Transactions

23:54 Dealing with the Due on Sale Clause

31:51 Creative Financing in the Current Market

42:15 Addressing the Risk of Non-Payment

43:06 Mitigating Risk with Mortgage Underwriters

45:11 Understanding the Do on Sale Clause

45:50 Strategies for Handling Regional Banks

47:05 Capital Raising Insights

47:33 Exploring Exit Strategies

47:42 Wraparound Mortgages Explained

51:12 Benefits of Using a Servicing Company

01:07:29 Co-Living as a Real Estate Strategy

01:17:52 Final Thoughts and Resources

Do you want to join a community of like-minded Military Real Estate Investors offering real estate education that actually works while celebrating camaraderie, and competition, and fostering a spirit of support?

Introducing ADPI Campus™ - the premiere platform and online space for Military Real Estate Investors worldwide! Podcast listeners can JOIN ADPI CAMPUS now and get in on the action!

Helpful Resources

Connect with the ADPI: Facebook | Instagram | YouTube

Please Subscribe, Rate, & Review on Apple Podcasts

Thanks for tuning in to this week's episode of the Active Duty Passive Income Podcast! If the information shared in these weekly interviews has inspired you to pursue your dreams of financial independence, please do me a personal favor and head over to Apple Podcasts, subscribe to our show, and leave us a 5-star review.

Support the show

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In this high-energy episode, Markian interviews Rob Pekarek, a Naval Academy graduate and active-duty Air Force officer, who shares his inspiring journey in real estate investing while serving in the military. Rob discusses his initial steps in real estate, starting from a single-family house hack to joining a general partnership team for multifamily deals. He emphasizes the importance of adding value, building strong teams, leveraging opportunities, and maintaining clear communication. Rob's strategic approach to networking, his commitment to serving others, and his focus on fitness, wealth, and purpose offer valuable lessons for anyone looking to succeed in real estate investing.

Episode Breakdown:

00:00 Introduction and Guest Overview

01:29 Guest Background and Early Career

06:33 First Real Estate Investment

10:59 Transition to Multifamily Investments

19:01 Joining a New Team and Scaling Up

27:25 Building Confidence with the Right Team

27:58 Aligning with Core Values

29:00 The Importance of Communication

29:46 Effective Communication Tools

32:07 Leveraging AI for Business and Personal Use

34:05 AI in the Military and Healthcare

36:12 Networking and Making Connections

41:10 Adding Value and Building a Brand

52:11 Final Thoughts and Advice

Join Rob’s free 30-minute class to learn how to get started with multifamily syndications. This crash course delivers exactly what aspiring investors need to know—no fluff, no sales pitch, just clear, actionable education designed specifically for the military community.

You can also connect with Rob on social media:

Instagram: @robthepek

LinkedIn: Robert Pekarek

💥 Ready to Level Up with a Like-Minded Community?

Join ADPI Campus™—the premier platform and online community built specifically for military real estate investors. Inside, you’ll find real-world education, camaraderie, competition, and the accountability you need to accelerate your journey.

🎓 JOIN ADPI CAMPUS and be part of a movement that’s changing lives: LEARN MORE

🔧 Helpful Resources:

Facebook | Instagram | YouTube

🎙️ Enjoyed the Episode?

If this conversation inspired you, helped you gain clarity, or sparked new ideas, please take a moment to subscribe, rate, and leave us a 5-star review on Apple Podcasts. Your support helps us reach more military members and families pursuing financial freedom through real estate.

Support the show

In this episode of the ADPI Podcast, host Markian Sich sits down with powerhouse military spouse, real estate investor, and soon-to-be author Kaitlyn Dannhardt, who reveals the wildly creative strategies that turned a broke PCS move into a full-fledged short-term rental business — all starting with just $1,500 and a VA loan.

From pioneering “TDY hacking” to PCS’ing with a garage full of Wayfair furniture, Kaitlyn breaks down how she leveraged military life’s instability to build wealth, flexibility, and financial freedom.

This is not your average house hacking story. It’s mindset meets mission — and a wake-up call for any military family still playing defense with their finances.

00 Introduction to Caitlyn Dan Hart

01:18 Caitlyn's Journey: From Teacher to Military Spouse

03:31 Discovering Airbnb and TDY Hacking

07:13 Scaling Up: From Mississippi to Alaska

08:31 The Importance of Strategic Planning

15:47 Outsourcing and Property Management

19:46 The Value of Patience and Vetting People

26:47 Flexibility in Business

27:08 Overcoming Initial Struggles

28:01 Growth and Improvement

30:57 Financial Independence and Passive Income

36:54 Networking and Conferences

38:12 Writing and Publishing a Book

48:15 Final Thoughts and Encouragement

💥 Want to Connect with a Community of Military Real Estate Investors?

Join ADPI Campus™—the world’s premier platform for military members and their families building wealth through real estate.

🎉 Join today: https://go.activedutypassiveincome.com/adpi-campus-join

Inside you’ll find real estate education that works, a supportive community that gets it, and the kind of camaraderie only service members can bring.

📲 Stay Connected with ADPI:

Follow us on Facebook | Instagram | YouTube

📢 Love the Show? Help Us Out!

If this episode inspired you or gave you a valuable takeaway, do us a solid—subscribe, rate, and leave a 5-star review on Apple Podcasts.

Your support helps us reach more military members chasing financial freedom through real estate.

🎧 Thanks for tuning in to the Active Duty Passive Income Podcast—where financial freedom is just one investment away.

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