Passive Income Pilots

39 Episodes

By: Tait Duryea and Ryan Gibson

Welcome to the Passive Income Pilots Podcast – the show designed to help pilots climb to new levels of financial success.Join Tait Duryea & Ryan Gibson, both airline pilots, business owners and investors, as they interview top experts and share practical knowledge on real estate, tax strategy, passive income and generational wealth. This one-of-a-kind show created specifically for professional pilots offers applicable strategies and tactics for improving your financial life. Whether you're a seasoned pilot or just starting out, we'll equip you with the expertise and confidence you need to upgrade your money and achieve true financial independence.

#37 - Empowering Insights and Strategies On Short-Term Rentals with Alex Jarbo
Last Tuesday at 3:00 PM

On this episode of Passive Income Pilots, Tait and Ryan interview Alex Jarbo.

Alex Jarbo is the founder and CEO of Open Atlas Investments. He is a visionary entrepreneur who is revolutionizing the vacation rental and hospitality industry, focusing on custom, unique micro-resort developments. Alex has an impressive portfolio of over $10 million in distinctive short-term rentals.

Alex shares valuable insights and tips on maximizing the potential of short-term rentals. He discusses the thriving market of short-term rentals and the benefits, tax advantages, and underwriting strategies for vacation rentals. He touches on regulations, themed properties, distribution...

#36 - Decoding the Untapped Potential and Complex World of Self-Directed IRAs with Derreck Long

On this episode of Passive Income Pilots, Tait and Ryan interview Derreck Long.

Derreck Long is a Senior IRA Specialist at Quest Trust Company. Quest manages IRAs for “alternative” investments like real estate, notes, oil and gas, and private placements, among many others. Derreck became a Self-Directed IRA and Solo 401K Expert in 2017. He received a CISP from the American Banking Association, spoke at hundreds of events around the United States, and even participated in lobbying efforts with Congress. 

Derreck provided valuable insights into the workings of self-directed IRAs, including ways to get money into retir...

#35 - Life Insurance Optimization and the Three-Pillar Investment Wealth-Building Strategy With Austin Dean

On this episode of Passive Income Pilots, Tait and Ryan interview Austin Dean.

Austin Dean is the founder and CEO of Waystone Advisors, a financial advisory firm that helps clients align their wealth and financial planning objectives. Since 2010, he has worked in the financial industry, and since 2012, he has advised clients. Austin holds a degree in Business and Marketing from the University of Washington. He holds four designations that he obtained to gain an in-depth understanding of the financial situations people face and the tools that can assist them. Austin is passionate about sharing his knowledge with...

#34 - Navigating Cash Balance Plans and Retirement for Airline and Corporate Pilots with Timothy Pope

On this episode of Passive Income Pilots, Tait and Ryan interview Timothy Pope.

Timothy Pope is a Certified Financial Planner and GA pilot who serves professional pilots across America. He has a Bachelor of Science degree from Wake Forest University. Before starting his practice in 2020, Tim worked as a financial planner at a large investment management firm for several years, followed by several years at a regional bank. Tim helps clients organize and optimize their financial lives using a straightforward planning process. He prefers an active, hands-on partnership where his clients’ goals, dreams, and values are central to...

#33 - Exploring the World of Mortgages, Refinancing, and Home Buying with Expert David Temko

On this episode of Passive Income Pilots, Tait and Ryan interview David Temko.

David Temko is the President of C2 Financial, where he spearheads a highly skilled team committed to optimizing the value of C2 Financial loan officers, who serve as comprehensive real estate and financial experts. David is pivotal to the company's continued growth as the #1 Mortgage Broker in the nation with his dedication to quality. Before C2, David contributed significantly to southern California's Wells Fargo Commercial & Business Banking Group. He is a respected mortgage executive with extensive experience in commercial loans, sales, leasing, and banking.<...

#32 - Tax Savvy Investing: The Power of Cost Segregation with Yonah Weiss

On this episode of Passive Income Pilots, Tait and Ryan interview Yonah Weiss.

Yonah Weiss is a cost segregation expert (#CostSegKing), real estate investor, and podcast host. With a background in teaching and a passion for education, Yonah helps property owners save millions of dollars in taxes with cost segregation. He has been featured on over 300 top real estate podcasts, sharing his insights and expertise on tax strategies. He also hosts his own podcast, Weiss Advice, where he interviews successful people from various fields. 

Yonah talks about the intricacies of cost segregation, debunking misconceptions and s...

#31 - Discover Profitable Oil and Gas Investments and Expert Strategies with Ben Fraser

On this episode of Passive Income Pilots, Tait and Ryan interview Ben Fraser.

Ben Fraser is Aspen Funds's Managing Director and CIO, a fund manager specializing in alternative income investments. He has over 10 years of experience in the financial industry, including commercial lending, credit underwriting, and energy infrastructure asset management. Ben was a key contributor to the growth of Tortoise Capital Advisors, a leading firm in energy infrastructure investments, from $3BN to $7BN in institutional managed accounts. He has an MBA from Azusa Pacific University and a B.S. in Finance from the University of Kansas.

#30 - Investing in Commercial Real Estate and Analyzing Economic Indicators with John Chang

On this episode of Passive Income Pilots, Tait and Ryan interview John Chang.

John Chang is the National Director of Research and Advisory Services for Marcus & Millichap, a leading commercial real estate brokerage firm. He oversees a team of experts who produce market research publications on various property types and sectors. He is a frequent speaker and commentator on commercial real estate trends and opportunities. John has a Bachelor of Business Administration degree from Washington State University and is a member of several industry organizations.

John brings his vast expertise to the table, unraveling the...

#29 - An Essential Guide to Decoding Non-Accredited and Accredited Investors

Today on Passive Income Pilots is Tait & Ryan's one-on-one episode.

Tait and Ryan break down SEC rules and the distinctions between 506B and 506C offerings. They lay out the qualifications needed to be an accredited investor and delve into the impact of the JOBS Act in 2012. They share the process of investor accreditation, from proving your accredited status to the operator to leveraging a third-party verification company, and the role professionals like attorneys, CPAs, or financial advisors play in validating it.

Enjoy the show!

Show notes:
[2:46] History of the regulation
[4:20] The...

#28 - Real Estate Investing For Wealth And Purpose With The Right Mindset With Alex Felice

On this episode of Passive Income Pilots, Tait and Ryan interview Alex Felice.

Alex Felice is the creative director for the BetterLife podcast. He is also a real estate investor, a ridiculously fantastic photographer, an ardent reader, an Army veteran, and a globe traveler. Alex realized in 2013 that he needed freedom if he wanted his life to have any real meaning. He had to find a way to escape the constant financial struggle he was experiencing and establish his life. He found success in the rental property market after listening to the BiggerPockets podcast, and in 2017 he...

#27 - Commercial Construction Management: A Deep Dive Into Ground-Up Development with Aaron Saunders

On this episode of Passive Income Pilots, Ryan interviews Aaron Saunders.

Aaron Saunders, the President of Spartan Construction Management, boasts 15+ years of construction leadership experience, having held positions as a Sr. Project Engineer, Project Sponsor, and Director of Operations. With a strong command of project planning, scheduling, contract management, engineering oversight, and subcontract management, Aaron has effectively managed concurrent projects ranging from 1M to 25M, totaling over 150M throughout his career. In addition to his role at Spartan Construction Management, he has been instrumental in building multiple construction teams and overseeing a diverse real estate portfolio that...

#26 - Decoding Yield on Cost: Interpreting Numbers and Assessing Investment Risks and Returns

Today on Passive Income Pilots is Tait & Ryan's one-on-one episode.

Tait and Ryan introduce the concept of "yield on cost" and explain its significance in assessing investment returns. They guide listeners on how to interpret yield on cost numbers effectively, enabling them to make informed decisions about potential investments. They discuss two common ways investors can lose money during a lease-up period and provide valuable insights on how to mitigate them and protect investors. They also talk about the stigma surrounding development deals and address misconceptions and biases associated with investing in development projects, emphasizing the potential...

#25 - From US Navy Pilot to Real Estate Expert: Unpacking 1031 Exchanges and DSTs with Trevor Flor

On this episode of Passive Income Pilots, Tait & Ryan interview Trevor Flor

Trevor Flor is an accomplished real estate professional with expertise in residential and commercial transactions. He graduated from UC Santa Barbara and, after graduating, founded his own brokerage firm, expanding it to include commercial real estate. Trevor's analytical skills led him to underwrite over $1.5 billion worth of medical-related real estate for Montecito Medical Investment Company and participate in more than $200M of transactions. He also served as a Navy pilot and an F-18A-F instructor. With an MBA from the University of North Carolina and...

#24 - Passive Investing: Syndication 101 – Key Players, Documents, Due Diligence, and Liquidity

Today on Passive Income Pilots is Tait & Ryan's one-on-one episode.

In this episode, Tait and Ryan explore syndication and its various aspects. They discuss the preferred return's crucial role in investment distributions and highlight the significance of fund of funds as intermediaries between limited partners and operators. They shed light on operators' responsibilities in managing investment projects and touch upon essential documents encountered in syndication deals. Lastly, they tackle liquidity and the importance of the Private Placement Memorandum (PPM) and due diligence for investor protection.
Enjoy the show!

Show notes:
[5:55] What is a...

#23 - Counting the Cost: The Risks and Rewards of 401(k) Loans for Pilots

Today on Passive Income Pilots is Tait & Ryan's one-on-one episode.

Tait and Ryan talk about the benefits and considerations of diversifying your investment portfolio to achieve long-term financial goals. They examine the advantages and potential drawbacks of maximizing your 401(k) contributions and shed light on 401(k) loan options. They discuss loan limits, risks, and the impact these may have on your retirement savings. They also share compelling examples of investors who took out 401(k) loans, exploring their motivations, experiences, and lessons learned along the way. They also quickly touched on rolling over a 401(k) to a self-directed...

#22 - Economic Trends, Multifamily, Angel Investing, and Investment Strategies with J Scott

On this episode of Passive Income Pilots, Tait & Ryan interview J Scott.

J Scott, also known as "J," is a multi-talented individual who has made a significant impact as an entrepreneur, investor, and advisor. He is widely recognized as the co-host of The BiggerPockets Business Podcast, where he shares his wealth of knowledge and experience with listeners. With an impressive track record, J has successfully engaged in various aspects of real estate, including purchasing, building, rehabbing, selling, syndicating, and holding residential properties, accumulating a portfolio worth over $70 million. As an accomplished author, J has written four highly...

#21 - Flight Plan for Finances: Financial Planning and Strategies for Pilots with Jesse Reed

On this episode of Passive Income Pilots, Tait & Ryan interview Jesse Reed.

CDR Jesse Reed graduated from Olathe East High School in 1998 and went on to graduate from the United States Naval Academy in 2002 with a Bachelor of Science in Political Science. He reported to NAS Pensacola for flight school, then to NAS Lemoore, CA for initial training in the F/A-18C Hornet, then to his first operational tour with the VFA-147 Argonauts and deployed aboard the USS JOHN C STENNIS in support of Operations Enduring and Iraqi Freedom. After graduation, he served as an instructor...

#20 - The Economic Landscape, Recession, Investing, and the Impact of AI Technology with Neal Bawa

On this episode of Passive Income Pilots, Tait & Ryan interview Neal Bawa.

Neal is the CEO and Founder of UGro and Grocapitus, two prominent commercial real estate investment companies. Leveraging cutting-edge real estate analytics technology, Neal's companies specialize in sourcing, acquiring, and building large commercial properties across the United States for a network of over 900 investors. With a current portfolio exceeding 4,800 units, Neal's companies boast an Assets Under Management (AUM) value of over $1 billion upon completion. Known for his expertise in real estate data analytics, Neal has developed a strong following among data-driven investors, with over 10,000 participants...

#19 - Invaluable Insights: ASAP Reports on Passive and Active Investment Deals

Today on Passive Income Pilots is Tait & Ryan's one-on-one episode.

Tait and Ryan candidly discuss their unfortunate experiences with passive and active investment deals. Drawing inspiration from the aviation industry's ASAP reports, these narratives offer real-life lessons for pilots or anybody planning to invest. Ryan shares a cautionary tale of his real estate investment experience, while Tait recounts his blundering with his first passive deal. Tait and Ryan provide actionable advice and strategies to assist listeners and fellow investors in their investment journey.

Enjoy the show!

Show notes:
[1:12] What is...

#18 - Credit Unions vs. Banks: Choosing the Right Financing Partner with Charles Krawitz

On this episode of Passive Income Pilots, Tait & Ryan interview Charles Krawitz.

Charles has over 30 years of experience in the financing industry. He has held leadership positions at esteemed financial institutions like ABN AMRO, KeyBank, and Fifth Third Bank. He is the  Senior Vice President, Chief Capital Markets Officer, and Head of Commercial Lending at Alliant Credit Union. Charles’ expertise encompasses loan trading operations, fintech partnerships, and co-branded employee benefits. He has received various accolades, including the Director of the Year award and induction into the Midwest Commercial Real Estate Hall of Fame. Charles holds finance and reg...

#17 - Mastering Real Estate Investing: Key Systems and Processes with Tarl Yarber

On this episode of Passive Income Pilots, Tait & Ryan interview Tarl Yarber.

Tarl Yarber is a seasoned real estate investor and CEO/Founder of Fixated Events, Fixated Capital, Fixated Funding, and The Limitless Expo. With over 600+ single-family residential properties purchased, rehabbed, and re-sold over the last 10 years, Tarl is a "Recovering House Flipper" who has now shifted his focus to BRRRR investing. Tarl is an expert in the investment industry and specializes in real estate systems for success. He has been a guest on the BiggerPockets Podcast, and is one of the leading video contributors of the...

#16 - Investing with Confidence: Asset Protection Strategies with Clint Coons

On this episode of Passive Income Pilots, Tait & Ryan interview Clint Coons.

Clint Coons is a founding partner of Anderson Business Advisors, a legal and tax firm that has grown to over 450 employees. He specializes in helping real estate investors create and implement solid entity structuring plans. Clint's personal investing experience has been key to his success in this field, having acquired over 200 properties, from small single-family homes to commercial buildings. As a prolific writer and educator, Clint has published numerous articles, videos, and workbooks on real estate investing and asset protection. He authored the book "Asset...

#15 - Why Commercial Real Estate Trumps Residential

Today on Passive Income Pilots, is Tait & Ryan's one-on-one episode.

Tait and Ryan discuss their success in creating $8M worth of equity in a storage facility. Ryan also talks about visiting his portfolio on the East Coast with the new president of their national storage company, FreeUp Storage. Tait shares how he got into real estate investing and explains the differences between single-family and multifamily properties. He also highlights why commercial real estate is an excellent investment opportunity. They discuss various real estate investment terminologies and strategies, including cap rates, value-add deals, and syndication investments. They also...

#14 - Depreciation Demystified: Cost Segregation and Tax Savings in Real Estate with Toby Mathis

On this episode of Passive Income Pilots, Tait & Ryan interview Toby Mathis for a second time.

Toby Mathis is a highly accomplished attorney, investor, speaker, and bestselling author known for his visionary leadership and expertise in the field of business and real estate investing. With his extensive knowledge and experience, Toby teaches US investors and professionals, including a popular bi-weekly live-streamed webinar called Tax Tuesday. As a founding partner of Anderson Business Advisors, he has played a significant role in earning his company numerous accolades, including being listed on the Inc 5000 (five times) and being recognized as...

#13 - Clean Profits: Building a Laundromat Empire with Sam Wilson

On this episode of Passive Income Pilots, Tait interviews Sam Wilson.

Sam Wilson is a seasoned real estate investor, entrepreneur, and host of the highly-rated podcast "How to Scale Commercial Real Estate." With over a decade of active investment experience in self-storage, parking, multi-family properties/apartments, single-family homes, RV Resorts, and laundry facilities, Sam has a diverse background in business ownership and management. He has helped others place their money outside of traditional investments, providing diversified strategies and solid, predictable returns. Sam's focus is now solely on acquiring and syndicating niche commercial assets that cash flow with...

#12 - Navigating Real Estate in Turbulent Times: Insights for Pilots with Russell Gray

On this episode of Passive Income Pilots, Tait & Ryan interview Russell Gray.

Russell Gray is the co-host of The Real Estate Guys Radio Show, a leading investment talk program airing on conventional radio since 1997 and podcasted in over 180 countries. With over 18 years of experience on the show, Russell has interviewed a variety of industry leaders and subject matter experts, including Robert Kiyosaki, Steve Forbes, Peter Schiff, and Donald Trump. As a financial strategist with a background in financial services dating back to 1986, he is a sought-after speaker and author, having co-authored the highly-rated...

#11 - How To Succeed In This High Interest Environment

Today on Passive Income Pilots, Tait & Ryan have their first one on one episode.

They share a captivating overview of what has been driving this financial climate. They discuss the skyrocketing interest rates and inflation, providing invaluable insights on how to stay ahead by leveraging interest arbitrage strategies while exploring the best investments for success.

Enjoy the show!

Show notes:
[0:00] Intro
[1:51] Quick history on how we got to the current financial situation
[6:05] How to win in this environment?
[9:00] The difference between 1yr, 3yr, and 5yr CDs
[12:45] Interest arbitrage<...

#10 - Reduce Your Taxes & Maximize Returns Using PROVEN Investment Strategies with Toby Mathis

On this episode of Passive Income Pilots, Tait & Ryan interview Toby Mathis.

Toby Mathis is a multi-talented attorney, speaker, bestselling author, and investor. He is a founding partner of Anderson Business Advisors and a visionary leader who has earned his company numerous accolades, such as being listed on Inc 5000 (5 times) and being one of the Best Places to Work. Toby teaches US investors and professionals, including a popular bi-weekly live-streamed webinar, Tax Tuesday.  Published by Forbes Books, Toby's book "Infinity Investing" is a #1 bestseller on Amazon and was awarded a Global Book Award — Gold Medal. Toby is a m...

#9 - Demystifying IRAs: Transfers Vs. Rollovers with Carrie Cook

On this episode of Passive Income Pilots, Tait & Ryan interview Carrie Cook.

Carrie Cook is the Chief Executive Officer of Preferred Trust Company (PTC) and the President of Ignite Funding. As CEO of PTC, a licensed retail trust company that acts as custodian for IRA owners' alternative assets, she is responsible for the company's overall operations, compliance, accounting, marketing/sales, and client relations. Carrie is a certified Self-Directed IRA Professional.

Carrie expertly simplifies the complexities of IRAs, providing a comprehensive overview that covers the fundamentals, nuances, and common misconceptions. She explains the different types of...

#8 - Blockchain and Web3: Transforming Finance With Trustless and Decentralized Ecosystems with Ben Jorgensen

So it'll be this: On this episode of Passive Income Pilots, Tait & Ryan interview Ben Jorgensen.

Ben Jorgensen, an American entrepreneur and investor in web3 technologies, has been featured on NASDAQ, Forbes, Entrepreneur Magazine, Hacker Noon, Cointelegraph, and ABC. He is the founder and CEO of Constellation Network, Inc., a web3 company with cryptocurrencies $DAG and $LTX, and one of two companies contracted to work with the US Department of Defense (including the US Air Force) and Civil Reserve Air Fleet. Constellation's decentralized network, Hypergraph, and smart contracts secure mission data for the DoD. Ben has an...

#7 - The Pilot Network and Navigating the Aviation Industry with Adam Uhan

On this episode of Passive Income Pilots, Tait & Ryan interview Adam Uhan.

Adam grew up in Milwaukee, Wisconsin, before becoming a military pilot. He moved across the country, became an airline pilot, visited six of the seven continents, started a family, and always wanted to be behind the microphone. Adam's first formal public speaking engagement was at an international military conference, where he presented to over 1500 people. The passion he developed during his career has fueled his desire to become the "voice from the flight deck" you trust, believe in, and want to hear again.


#6 - Transitioning from Active to Passive Investing and Diversifying Investments with Jeremy Roll

In this episode of Passive Income Pilots, Tait and Ryan interview Jeremy Roll.

Jeremy started investing in real estate and businesses in 2002, and left the corporate world in 2007, to become a full-time passive cash flow investor. He is currently an investor in more than 70 opportunities across more than $1B worth of real estate and business assets. As Founder and President of Roll Investment Group, Jeremy manages a group of over 1,500 investors who seek passive/managed cash-flowing investments in real estate and businesses. Jeremy is also the co-Founder of For Investors By Investors (FIBI), a non-profit organization that...

#5 - Live at the BEC 2023 (Where It All Started)

On this special episode of Passive Income Pilots, Tait and Ryan go live from the Best Ever Conference in Salt Lake City, Utah.

Since this event was where it all started for Tait and Ryan, they celebrated the launch of this podcast by recording this episode live on stage in the middle of this year’s conference. If you’re new to this arena, the Best Ever Conference (BEC) is a marketplace where individual investors meet other solo investors and operators and is the perfect place to network and learn about the different investment spaces and various inve...

#4 - Build A Solid Investment Strategy Before Pushing The Throttle Forward with Alex Tapia

On this episode of Passive Income Pilots, Tait and Ryan interview Alex Tapia.

Alex is an ex-US Airways pilot who, after the events of 9/11 took place, knew a change in the direction of his profession was needed. With a belief that “pilots don’t make good employees”, he created his own company, Aviation Retirement Strategies (ARS).  His goal was to make the complicated world of finance more easily available and understandable to aviation professionals (mainly pilots), as “supporting pilots is all he cares about”. His wealth-management company has an incredibly impressive portfolio of over $1B of assets under manag...

#3 - Investments and Wealth Management for Aviators with Austin “Strobes” Hulbert

On this episode of Passive Income Pilots, Tait and Ryan interview Austin “Strobes” Hulbert.

Austin was born into an aviation family and naturally gravitated toward becoming a pilot himself.  He graduated from the United States Naval Academy in 2005 and immediately moved onto obtaining his M.A. in Security Studies from Georgetown nine months later. He then attended flight school for two years and eventually landed in Virginia Beach, where he became an F/A-18 Hornet and Super Hornet pilot, completed a deployment on the USS Enterprise, and then became a flight instructor, all while spending his free time...

Special Episode: The Silicon Valley Bank Collapse

On this special episode of Passive Income Pilots, Tait and Ryan share a quick analysis of the recent collapse of the Silicon Valley Bank (SVB) on March 10, 2023. This was the second largest bank collapse in United States history and was triggered by a run on deposits and a lack of new capital. SVB was a favorite amongst founders and tech companies and had become an international icon for venture capital. The collapse of SVB caused a rough week for the banking industry, raising concerns about the stability of the financial sector. Tune in to this special episode to know...

#2 - Invest Passively in DST and Opportunity Zones with Brandon Bruckman

On this episode of Passive Income Pilots, Tait and Ryan interview Brandon Bruckman.

Brandon is an investment advisor and RIA with Insight Advisors, who specializes in helping clients invest passively in Delaware Statutory Trusts (DSTs), 1031 exchanges, and OZ funds. He has worked with large and small businesses in the financial services, logistics, and pharmaceuticals industries. He also previously worked for a hedge fund as the Head of Fixed Income Financing, and was deeply impacted by the financial crisis. Following that experience, he co-founded a healthcare consultancy assisting hospitals in making vendor selections.

In this episode...

#1 - How Can Pilots Position Themselves for Success with CNBC’s Fast Money Trader Guy Adami

On the first episode of Passive Income Pilots, Tait and Ryan interview Guy Adami.

Adami is the longest, original member of CNBC’s show “Fast Money”, and also currently serves as the Director of Advisor Advocacy at Private Advisor Group in New Jersey. He is a professional investor, with a background in hedge fund management, and has built a network of advisors with over $17 billion in assets. Adami has held numerous key leadership roles in the financial services industry from Vice President and Head Gold Trader at Drexel Burnham Lambert, to Head Gold Trader and Director of the In...

The Men Behind Passive Income Pilots

Welcome to the highly-anticipated debut episode of Passive Income Pilots, the ultimate platform for aviators seeking to explore the world of finance, real estate, and investing. After years of friendship, planning and preparation, Tait Duryea (Turbine Capital) and Ryan Gibson (Spartan Investment Group) are thrilled to finally unveil their groundbreaking show.

In this episode, hosts Tait and Ryan delve into the genesis of Passive Income Pilots, and share their individual and collective excitement and vision for the show. With a combined 30 years experience in the airline industry and even more time researching and investing in real estate...