Truly Passive Income

In this episode of the Truly Passive Income Podcast, hosts Neil Henderson and Clint Harris are joined by the insightful Chad Ackerman, co-founder of Left Field Investors. Diving into a captivating discussion, they reminisce about their recent encounter at the 'best ever conference' in Salt Lake City and delve deep into the world of passive investing. From market nuances to community building, this episode promises a treasure trove of knowledge for every passive income enthusiast.

[00:01:25] - Introduction and Chad's initial journey into passive investing

[00:11:37] - Strategic approaches to passive investing

[00:15:07] - The rapid growth of Left Field Investors

[00:17:50] - Incorporating financial education into daily life

[00:20:20] - Chad's decision to leave the corporate world

[00:23:02] - The intricacies of underwriting deals

[00:25:57] - Diverse investment opportunities across locations

[00:28:44] - Chad's affinity for unique investment ventures

[00:31:03] - Balancing investment strategies with personal life stages

[00:34:06] - Realizations and reflections on passive income

• Chad Ackerman's introduction and his role as the co-founder of Left Field Investors.
• The importance of passive investing and the journey to understand its potential.
• The transformative power of self-investment and the role of podcasts in personal growth.
• Different paths in the real estate trajectory and its varied experiences.

Website: LeftFieldInvestors

Email: [email protected]

YouTube: Left Field Investors

Books Mentioned: Anti-Fragile by Nassim Nicholas Taleb

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here

What if you could sell a property, walk away with a massive gain, and pay zero taxes on it — legally? That's the power of the 1031 exchange, and Dave Foster has spent his career showing investors how to use it to build the kind of wealth most people never thought possible.

Dave joins Neil and Clint to break down the mechanics behind this powerful tax-deferral strategy, starting with his own unlikely story of living aboard a sailboat with his family — a lifestyle made possible by the financial freedom that smart tax planning creates. He covers the "Four Ds" that drive most exchange decisions, the overlooked potential of reverse exchanges, and a strategy for converting an investment property into a primary residence that could eliminate capital gains taxes entirely. He also explains how the step-up in basis makes the 1031 exchange one of the most powerful generational wealth tools available to real estate investors today.

[00:03:05] How Dave used 1031 exchanges to convert investment properties into primary residences to generate tax-free profits

[00:06:05] Overview of primary residence capital gains tax exemption rules

[00:09:02] How Dave leveraged 1031 exchanges to fund an early retirement on a sailboat

[00:19:35] Dave explains the "4 D's" of 1031 investing - Deferred, Delay, Defer, Dodge

[00:23:12] Using 1031 exchanges to relocate and purchase undervalued properties

[00:27:18] Converting 1031 investment properties into primary residences

[00:31:37] Hacking 1031 exchanges to invest in syndications

[00:37:25] Paying some tax to invest in syndications with 1031 proceeds

[00:39:57] Overview of reverse 1031 exchanges

[00:44:13] Advanced strategies for improving 1031 exchange properties

• 1031 exchanges allow real estate investors to defer capital gains taxes by selling one investment property and reinvesting the proceeds into another
• When timed strategically, 1031 exchanges can be used to convert investment properties into primary residences to generate tax-free profits
• Portfolios can be built up substantially over time by continually deferring taxes through 1031 investing
• Towards the end of one's career, 1031 exchange properties can be converted into primary residences to eliminate deferred tax liabilities
• Reverse 1031 exchanges enable investors to secure replacement properties before selling relinquished properties
• With proper planning, 1031 exchange proceeds can be invested into real estate syndications

Dave Foster's Book: Lifetime Tax Free Wealth

Dave's Website: The1031Investor.com

Dave's YouTube Channel: The 1031 Investor

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing - Download Here

Passive real estate investing requires education and community. In this episode, Jim Pfeifer explains how he built Left Field Investors from a small mastermind into a 1300+ member syndication education platform.

Jim started investing in syndications with no clue what he was doing. After losing money and having mixed results, he discovered the power of an engaged community for vetting sponsors and deals. Now Jim uses Left Field Investors to “community” potential investments, transferring trust through member referrals.

Across 90+ LP positions in multifamily, self-storage, mobile homes, and alternative assets like ATMs and bitcoin mining, Jim has invested in nearly every syndication niche imaginable. He shares lessons learned from both successful and failed deals. If you want to take your syndication education and due diligence to the next level, this episode is a must-listen.

[00:31] Jim's background as a teacher and financial advisor

[01:41] The origins of Left-Field Investors during the pandemic

[02:52] Providing a network, education, and deal flow for members

[04:17] Jim's journey to becoming an LP investor

[06:52] Using the community to vet sponsors before investing

[10:15] Why real estate investing is better than stock market speculation

[12:34] Jim's investment portfolio across many alternative assets

[16:05] Communication is the key factor when evaluating sponsors

[19:12] The common denominator of bad deals - lack of sponsor due diligence

[21:26] Using leverage like HELOCs to invest in ATMs

• Left Field Investors started as a small mastermind group and grew into a 1300+ member community providing education and resources for passive real estate investors.
• Having a community helps vet syndication sponsors before investing since these are long-term illiquid deals. Trust transfers through referrals.
• Jim transitioned from being a teacher and financial advisor to a full-time LP investor across 90+ deals in multifamily, self-storage, mobile home parks, and alternative assets like ATMs.
• Strong communication is the number one factor Jim looks for when evaluating potential sponsors to invest with.
• Bad deals often happen when sponsors pivot to new asset classes without the right experience. Jim avoids being sponsors' "guinea pigs" in new niches.
• Leveraging things like HELOCs to invest in short-term alternative assets like ATMs can provide strong returns by having money work double duty.

Website: Left Field Investors

Podcast: Investing from Left Field

Facebook: Left Field Investors

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive Inc

Twitter: @trulypassive

Everything you need to get started in passive investing in real estate syndications - https://trulypassiveincome.com/toolkit/

Derek Horn, an explosive ordinance disposal expert in the Air Force, shares how he accidentally got into real estate investing by purchasing his first home. He grew his portfolio through a family deal, and eventually invested passively by partnering with a syndicator. Derek provides unique insights into considerations military members face when investing remotely, utilizing property managers, and thinking long-term about financial freedom.

[00:00] Introduction to Derek Horn's background

[07:35] Buying his first investment property by accident

[08:53] Growing his portfolio through a family deal

[13:15] Partnering with a syndicator for passive investing

[23:19] Dealing with evictions as a remote investor

[27:57] Managing property managers as a remote investor

[34:14] Hosting a group for military passive investors

• Derek started investing by accident when he purchased a home to remodel and rent out. This led to buying more properties in different locations during military moves.
• Partnering with family on a property deal allowed Derek to quickly scale up his portfolio. Family deals can provide opportunities not available on the open market.
• Investing remotely from overseas locations like Japan limits options for finding deals, leading Derek to partner with a syndicator for passive investing opportunities.
• As a remote investor, hiring property managers is helpful but does not make investing completely passive. Managing the managers is an ongoing task.
• Derek hosts a group for military members interested in passive investing. This provides invaluable networking and the ability to discuss military-specific investing considerations.

• Active Duty Passive Income Group: https://www.facebook.com/ActiveDutyPassiveIncome

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing

https://trulypassiveincome.com/toolkit/

Are you a passive investor seeking strategies to maximize your tax benefits and enhance your investments? Join seasoned financial experts Neil Henderson, Matt MacFarland, and Amanda Han as they reveal the secrets of tax-efficient investing in this eye-opening episode. Discover the Lazy Man's 1031 Exchange, the potential benefits of Opportunity Zones, and how to successfully navigate the complex world of syndications. If you're ready to transform your investment approach and build a more profitable future, hit play and unlock the power of smart tax planning!

• Real estate syndications offer tax-saving opportunities through accelerated depreciation and cost segregation studies. By generating losses to offset gains, passive investors can benefit from a reduced tax burden.
• To maximize tax savings with real estate syndications, passive investors should consider investing in projects that conduct cost segregation studies. This will allow them to take advantage of the accelerated depreciation, which can help offset taxable income from other sources.
• Passive investors in real estate syndications can take advantage of tax deferral strategies such as the "Lazy Man's 1031 Exchange." This involves reinvesting distribution gains from one syndication into another within the same tax year, thus offsetting the capital gains and minimizing tax liability.
• When evaluating potential investments in opportunity zones, passive investors should look for projects that not only defer taxes on capital gains but also offer the potential for tax-free appreciation over a long-term investment horizon.
• For passive investors seeking to minimize tax liability, it's crucial to work with experienced tax professionals who understand the complex rules and regulations governing syndications and can help them navigate tax-saving strategies effectively.
• Tax planning is essential for passive investors in real estate syndications. Stay in touch with your tax professional throughout the year. Don’t wait until tax season to communicate with them.

[00:00] Intro

[01:19] Passive investor tax benefits

[02:11] Cost segregation & depreciation

[04:30] Real estate syndications & 1031 exchange

[07:52] Lazy Man's 1031 exchange explained

[10:26] Challenges in 1031 exchange & syndications

[14:28] Opportunity Zones & tax Benefits for passive investors

[18:22] Timing investments to offset capital gains

[20:53] Evaluating potential investments in opportunity zones

[22:18] Long-term benefits of opportunity zone investments

[24:30] Understanding TICs (Tenants in Common) in Syndications

[26:45] Role of cost segregation studies in maximizing tax savings

[28:16] How passive investors can reinvest their capital gains

[30:12] The importance of tax planning in real estate syndications

[32:08] Creating a tax-efficient investment strategy

[33:55] Key takeaways on maximizing tax benefits in passive real estate investing

[35:22] Closing thoughts and future strategies for passive investors

[37:00] Outro

Website: Keystone CPA

Book: The Book on Tax Strategies for the Savvy Real Estate Investor: Powerful techniques anyone can use to deduct more, invest smarter, and pay far less to the IRS!

Amanda Han's Facebook page

@amanda_han_cpa on Instagram

@AmandaHanCPA on X

Amanda Han on YouTube

Support Our Show Follow us on Twitter @trulypassive Follow us on Facebook at TrulyPassiveInc Follow us on TikTok @TrulyPassiveIncome Sign up for our FREE Passive Investor Course

In this episode of the Truly Passive Income podcast, hosts Neil Henderson and Clint Harris sit down with Robert Shortsleeves, a real estate investor who has paved his own path to financial freedom. Starting in Alabama, Robert ventured into the world of real estate after a career in the Army, utilizing off-market deals to build his real estate empire. He shares his journey, offering unique insights into the importance of building a reliable team, and how to level up in the world of real estate by focusing on adding value to those just ahead of you on the journey.

Robert brings a wealth of knowledge to the table, discussing everything from real estate syndications to the importance of learning from those just a few steps ahead of you. His refreshing honesty about the challenges and triumphs of his journey provides listeners with a candid look into the world of real estate investing.

In addition to his real estate success, Robert speaks about his inspiring three-month vacation/remote work trip to Bali, demonstrating the life-changing potential of financial independence. This episode is a must-listen for anyone interested in real estate investing, financial freedom, and the pursuit of a life lived on your own terms.

[00:00] Intro

[01:52] Introduction to Robert Shortsleeves

[02:49] Robert's journey into real estate investing

[07:25] The power of timing in real estate

[10:20] Robert's experience with his first deal

[13:05] How Robert leverages off-market deals

[18:10] Robert's big move to Bali

[22:15] The importance of learning from others in the industry

[27:00] Robert's approach to giving back to the community

[33:59] How to get in touch with Robert Shortsleeves

[34:54] Closing remarks

• The Potential of Off-Market Deals: Robert Shortsleeves emphasizes the potential of off-market deals in real estate, which can often offer great opportunities for investors. His success in this area shows that off-market properties can be a lucrative avenue for generating passive income.
• Learn from Those Ahead of You: Robert advocates for learning from people who are just a few steps ahead of you on the path to financial freedom. This practical advice encourages individuals to seek mentors who still have a fresh perspective on the challenges beginners might face.
• Financial Freedom Enables Adventure: Robert's ability to plan a three-month remote work trip to Bali highlights the freedom that financial independence can provide. By achieving financial stability, one can have the flexibility to explore new places and experiences without financial constraints.
• The Importance of Giving Back: Robert believes in giving back to the community and helps others achieve their goals in real estate. This approach not only contributes to the community but also fosters a culture of shared knowledge and success.
• The Journey Towards Financial Independence: Robert's story underscores the journey towards financial independence, with its challenges and rewards. His experience serves as a testament to the fact that with hard work, determination, and strategic thinking, financial independence through real estate investing is achievable.

Website: Shortsleeves Real Estate

Facebook: Robert Shortsleeves' Facebook

Facebook: facebook.com/TrulyPassiveInc

Twitter: twitter.com/trulypassive

YouTube: Truly Passive Income

If you enjoy the podcast, would you please consider leaving a short review wherever you listen to podcasts? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests.

For show notes and past guests, please visit trulypassiveincome.com/podcast

Download Our FREE Passive Investor Toolkit https://trulypassiveincome.com/toolkit/

Self-storage facilities can provide lucrative passive income opportunities compared to other types of real estate investments. In this episode, Drake Massa, Director of Acquisitions at Nomad Capital, joins hosts Neil Henderson and Clint Harris to discuss self-storage investing.

00:00:30 - Drake provides background on his role at Nomad Capital

00:02:30 - Drake explains why self-storage is a good passive income investment

00:04:40 - Drake outlines the four main self-storage investment strategies

00:08:00 - Drake details the conversion strategy for self-storage investing

00:15:15 - Drake discusses projected returns and timelines for investors

00:21:40 - Drake explains the refinancing strategy in years 4-6

00:26:00 - Drake emphasizes the work required despite the passive income

00:30:50 - Drake walks through the deal funnel from start to finish

00:37:05 - Drake shares where he would invest $100k right now

• Self-storage has outperformed all other commercial real estate over the past 5 years and leads most industries in growth over the past 25+ years,  even during recessions.
• The four main self-storage investment strategies are: 1) Buy existing facility and improve operations 2) Buy existing facility and expand it 3) Convert other buildings into storage facilities 4) Build new self-storage facilities from the ground up.
• Conversions provide the best risk-reward balance. Purchasing underutilized buildings for cheap and converting them into self-storage can generate huge returns.
• It takes significant expertise and effort to find, analyze, negotiate, and execute self-storage deals, despite the passive income for investors.
• Drake reviews 100+ deals per week, models 5%, negotiates on 1%, and closes nearly 100% once an offer is made. From contract to completion takes 6-12 months.

LinkedIn: Drake Massa

Website: Nomad Capital

Email: [email protected]

YouTube: Truly Passive Income

TikTok: @trulypassiveincome

Instagram: @truly_passive_income

Facebook: Truly Passive

Twitter: @trulypassive

Everything you need to get started in passive investing

https://trulypassiveincome.com/toolkit/

Are you looking for a smart way to manage your passive investments without sacrificing valuable time? In this compelling episode of Truly Passive Income, we sit down with Litan Yahav, the founder and CEO of Vyzer, a powerful platform designed to help passive investors keep track of their investments with ease. Litan shares his personal journey, how he discovered the value of truly passive investing and the innovative solution he built to streamline investment tracking.

Listen in as we discuss Litan's unique perspective on passive investing, the importance of trusting the people you invest with, and how Vyzer can save you time while keeping you informed about your investments. 

[00:00] Intro

[03:11] Litan Yahav's journey to passive real estate investing

[05:58] The importance of time management in investing

[08:45] Challenges of keeping track of multiple investments

[13:52] Introducing Vyzer: a solution to manage passive investments

[20:00] How Vyzer helps investors stay organized and informed

[27:30] Pricing of Vyzer's subscription plans

[28:58] Litan's advice for passive investors

[30:40] The importance of trusting the right people

[32:09] Outro

• The importance of time in passive investing: Litan Yahav shares his journey and emphasizes the value of time as the primary factor that led him to invest passively in real estate.
• The challenge of managing multiple investments: Litan highlights the difficulties faced by passive investors in keeping track of their investments and the distributions they receive.
• The birth of Vyzer: To address these challenges, Litan created Vyzer, a platform designed to help passive investors manage their portfolios and monitor their investments in an organized and efficient manner.
• Streamlined communication with GPs: Vyzer allows investors to stay on top of their distributions by creating distribution schedules and flagging when distributions are missing or underperforming, making it easier for investors to communicate with GPs.
• Accessible pricing for various investment levels: Vyzer offers a flat subscription fee, making the platform accessible to investors with different investment levels, from those with hundreds of LP positions to those with just a handful.
• Finding trustworthy operators and syndicators: Litan stresses the importance of building relationships and trust with the people you invest with, as it can significantly impact the success of your passive investments.
• Focus on people and numbers: Litan's approach to passive investing involves prioritizing the people he invests with and ensuring the numbers match his current investment strategy, rather than focusing on specific asset classes or geographies.
• The value of small to medium-sized operators: Litan shares his preference for smaller, more personal operators who don't have hundreds of investors and can offer more tailored communication and attention to their investments.
• Truly passive income comes from investing capital with the right team: Trusting an experienced team to execute their business plan is crucial to achieving truly passive income from real estate investments.
• Networking and mastermind groups: Litan emphasizes the importance of connecting with other investors and learning from their experiences through networking, attending mastermind groups, and listening to podcasts like Truly Passive Income.

Truly Passive Income: www.trulypassiveincome.com

Website: www.vyzer.co

Facebook: https://www.facebook.com/litanyahav

Facebook: https://www.facebook.com/vyzerfinance/

LinkedIn: https://www.linkedin.com/in/litanyahav/

Twitter: https://twitter.com/YahavLitan

Facebook: www.facebook.com/TrulyPassiveInc

TikTok: https://www.tiktok.com/@trulypassiveincome

Twitter: www.twitter.com/trulypassive

If you enjoy the podcast, would you please consider leaving a short review wherever you listen to podcasts? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. For show notes and past guests, please visit www.trulypassiveincome.com/podcast

Everything you need to get started in passive investing

https://trulypassiveincome.com/toolkit/

🎧 Tune in to this eye-opening episode where we dive deep into the journey of Alex Felice, a successful real estate entrepreneur who discovered that financial independence is just the beginning. Learn how Alex's experiences led him to seek greater meaning and purpose, both through his pilgrimage on the Camino de Santiago and his current life in Maui. Get ready to be inspired and challenged as we discuss the importance of digital detox, connecting with nature, and embracing adventure. Join us for this must-listen episode that will leave you questioning the true definition of success and what really matters in life. Hit play now and start your own journey towards personal fulfillment! 🌟

Time Stamps:

[00:00] Intro

[03:25] Alex Felice's real estate journey and achieving financial freedom

[06:48] The realization that success isn't just about money

[12:03] Alex's transition to photography and finding fulfillment

[20:52] The importance of pursuing passions and purpose

[28:15] How location independence can change your life

[37:08] Insights on finding happiness beyond financial independence

[44:20] The concept of "Success, but what else?"

[56:35] Clint Harris congratulates Alex and plans a visit

[57:14] Alex Felice on success and finding your "what else"

Key Takeaways

• Financial independence is just the beginning: While achieving financial independence through passive real estate investing can provide a sense of security, it's essential to recognize that it's not the end goal. True happiness and fulfillment come from discovering your purpose and pursuing what matters most to you in life.
• Success is subjective: Alex Felice's story teaches us that success looks different for everyone, and it's important to define it on your own terms. For some, it may mean continuing to invest in real estate, while for others, it could mean embarking on a completely new journey.
• Growth through challenges: Embracing and overcoming challenges, like Alex's experience with the Camino de Santiago pilgrimage, can lead to significant personal growth and a deeper understanding of one's purpose.
• The power of self-reflection: Taking the time to reflect on your life, values, and what truly brings you happiness is crucial for maintaining a sense of balance and well-being, especially after achieving financial freedom.
• Cultivating a sense of adventure: Exploring new opportunities, experiences, and passions can lead to a more fulfilling life beyond the realm of financial success. Alex's transition from real estate entrepreneur to world traveler and visual storyteller is a prime example of this.
• The importance of community and connections: Building meaningful relationships and engaging with like-minded individuals can help enrich your life and provide a strong support system as you pursue your passions and purpose.
• Balance and sustainability: As you work toward financial freedom and explore your passions, it's important to maintain a balance between your personal, professional, and financial life to ensure long-term happiness and success.
• Embracing change: Alex's story highlights the importance of being open to change and adapting to new circumstances as you pursue your passions and purpose in life.
• Learning from others' experiences: Listening to stories and insights from people like Alex Felice can inspire and guide you on your own journey toward finding purpose and happiness beyond financial freedom.
• The journey never ends: Achieving financial freedom and discovering your true purpose is an ongoing process that requires continuous growth, self-reflection, and adaptation. Embrace the journey, and you'll find a richer, more fulfilling life beyond passive income.

📚 Resources & Social Media:

Alex Felice's Instagram: @alexscottfelice

Alex's Photography Website: lifeandlens.media

Broke is a Choice: www.brokeisachoice.com

Truly Passive Income website: www.trulypassiveincome.com

Truly Passive Income Twitter: @trulypassive

David Foster Wallace Commencement Address: This is Water

In this episode, Neil Henderson and Clint Harris talk to Tim Vitale, a multifamily real estate syndicator and founder of Upside Capital Group. With a focus on time, financial, and location independence, Tim discusses his journey into the world of real estate syndication, his strategies for analyzing deals, and the importance of building strong relationships with investors. Tim also shares his insights on debt coverage ratio, timeframes, and how to choose the right operator for a successful investment.

In This Episode, We Cover:

[03:27] How Tim Vitale got into real estate syndication

[09:36] Importance of understanding the market and job growth

[12:16] Analyzing deals and the importance of debt coverage ratio

[15:31] Timeframes and protecting your investments

[27:45] Alignment of interests and choosing the right operator

[28:49] Advice for passive investors in multifamily syndications

[31:12] Connecting with Tim Vitale and Upside Capital Group

Books and Resources Mentioned:

Truly Passive Income: trulypassiveincome.com

Website: Upside Capital Group

Facebook Group: Making Moves Real Estate Community

Support Our Show Follow us on Twitter @trulypassive Follow us on Facebook at TrulyPassiveInc Follow us on TikTok @TrulyPassiveIncome Sign up for our FREE Passive Investor Course

Pithy, Shareable Quotes:

"Real estate over the long term, you're gonna win. It's the people that get burned in the short term because they don't have time on their side." - Tim Vitale

"Go build a relationship with the person that you wanna invest with. Spend time in person with that person." - Tim Vitale

Coming Up Next on Truly Passive Income: