Best Left Field Investors Podcasts (2024)

1
How to Vet an Operator in a Real Estate Syndication 49:36

1h ago49:36

49:36

How to Vet an Operator | Hosted by Jim Pfeifer and Co-Hosts: Mauricio Rauld and Jeremy Roll In this episode, Jim Pfeifer uncovers the critical steps to vetting an operator before making passive investments. Whether you're a seasoned investor or just starting, Jim offers invaluable advice on: Key questions to ask operators before committing Assessin…

1
EP 118: Will Gaybrick (President of Product and Business, Stripe) on Capital Allocation, Org Design, AI, and Global Growth 1:42:18

5d ago1:42:18

1:42:18

Will Gaybrick joined Stripe as CFO after investing in the company at Thrive Capital. Over the past 9 years, now as President, he's helped grow Stripe's into one of the world's largest private startups. In this episode, we explore his impressive career journey—from Harvard Math to software engineering, Yale Law, venture capital, and now his leadersh…

1
Top Proven Strategies to Achieve Passive Success in Real Estate Investing 44:22

6d ago44:22

44:22

Looking to succeed in real estate investing? In this podcast episode, host Jim Pfeifer and guest Kathy Fettke, a seasoned real estate investor and expert, shares his top proven strategies to help you achieve long-term success in the competitive world of real estate. Whether you're just starting or already have experience, these expert tips will gui…

1
EP 117: Parker Conrad (CEO, Rippling) His Opinion on Founder Mode, Fundraising, and VC Advice 1:42:29

7d ago1:42:29

1:42:29

Parker Conrad has spent the last 8 years building Rippling into a $13B company, marking his redemption after being ousted from Zenefits. In his second appearance on the podcast, Parker and I discussed Paul Graham's "founder mode" essay and how he operationalizes it at Rippling. He also reflected on the key lessons he's learned throughout his career…

1
Your Beginner's Guide To Passive Investing 1:08

3d ago1:08

1:08

Welcome to PassivePockets: The Passive Real Estate Investing Show, where we help you build and protect your wealth through smart, hands-off real estate investments. Hosted by Jim Pfeifer, each episode brings you expert interviews with experienced Limited and General Partners who share practical tips and strategies for growing your portfolio without…

1
184: From Left Field to Passive Pockets: A Journey of Community and Collaboration 40:07

17d ago40:07

40:07

Welcome to a special episode of Passive Investing from Left Field! In this episode, we’re thrilled to announce a groundbreaking partnership between Left Field Investors and Bigger Pockets, resulting in the creation of Passive Pockets. Join us as the founders reflect on our journey, discuss the benefits of this new chapter, and share how this merger…

1
EP 116: John Fieldly (CEO, Celsius) How He Saved Celsius From Near Bankruptcy to a $10B Company 1:06:53

14d ago1:06:53

1:06:53

Many know Celsius as a top energy drink brand today, but few are aware of the tumultuous journey CEO John Fieldly took to get it here. In the episode, John shared how the company nearly went bankrupt multiple times, lost 50% of its revenue overnight and even got delisted from the NASDAQ. Despite these challenges, John stepped up to rebuild the bran…

1
183: Overcoming Challenges in Real Estate with Joe Fairless 58:12

24d ago58:12

58:12

Joe Fairless and the Best Ever Conference team would like to invite you to BEC2025 and have provided a discount for Passive Investing from Left Field Listeners. Please enter "LFI25" at checkout for a discounted price of $795. You can register at this link: https://besteverconference.regfox.com/bec-2025 In this episode of Passive Investing from Left…

1
EP 115: Josh Wolfe (Co-Founder, Lux Capital) On Uncovering Hidden Opportunities 1:54:27

21d ago1:54:27

1:54:27

Josh Wolfe, co-founder and managing partner at Lux Capital, is a master at quickly understanding complex, emerging technologies. In our conversation, Josh shared how he identifies the next big thing, his contrarian views on nuclear energy, biotech, and robotics, as well as his thoughts on the state of the venture capital market today. (00:00) Intro…

1
182: Captain Hoff on the Explosive Growth of AI, Startups, and Venture Capital 48:16

1M ago48:16

48:16

In this episode, we dive deep into the world of AI, startups, and venture capital with none other than Steven Hoffman, also known as Captain Hoff. As the CEO of Founders Space and a veteran of Silicon Valley, Steve shares his insights on the future of AI, how to navigate the startup ecosystem, and the best strategies for investing in the next big t…

1
EP 114: Emery Wells (CEO, Frame.io) on Selling to Adobe for $1.3B, Working with SNL and High Pain Tolerance 1:41:57

28d ago1:41:57

1:41:57

Emery Wells is the co-founder and CEO of Frame.io, which he sold to Adobe in 2021 for nearly $1.3 billion. In our conversation, Emery shares his journey from NYC bartender to startup founder, including his agency work with Saturday Night Live that highlighted the pain points that led to Frame.io. We dive deep into his rejection of the lean startup …

1
181: Bonus Episode - Syndication Secrets: Empowering Investors with Russell Gray REPLAY 1:02:25

2M ago1:02:25

1:02:25

Join us for a replay of this insightful episode as we sit down with Russell Gray, financial strategist and co-host of The Real Estate Guys Radio Show. Russell shares his journey from real estate to syndications, offers invaluable lessons from economic history, and provides strategies for navigating today's financial landscape. Whether you're a seas…

1
EP 113: Dara Khosrowshahi (CEO, Uber) Lays Out the Path to Autonomous Vehicles 1:09:15

1M ago1:09:15

1:09:15

Dara Khosrowshahi runs one of the most complicated businesses in the world, Uber. Since taking over in 2017 Dara has led the company to profitability against all odds. In this episode, we touch on a number of things including Uber’s position on the future of Autonomous Vehicles (AVs), the challenges that were overcome in making Uber profitable, and…

1
180: Navigating Real Estate in 2024: Strategies and Insights with Big Mike 40:42

1M ago40:42

40:42

Join us on the Passive Investing from Left Field podcast as we dive deep into the world of real estate investing with our special guest, Mike Zlotnik, also known as Big Mike. In this episode, we explore the current distressed real estate market, strategies for passive investors, and how to navigate the challenges of today's high-interest environmen…

1
EP 112: Mike Maples (Founding Partner, Floodgate): What Makes Startups Win & The Future of Venture Capital 2:03:48

1M ago2:03:48

2:03:48

Mike Maples is an 8x Midas List investor and founding partner at Floodgate Fund. In our conversation, we dive into his latest book, "Pattern Breakers: Why Some Startups Change The Future." Mike shares his frameworks on how top startups beat incumbents by redefining categories, and he reflects on his worst and best decisions. We also discuss what th…

1
179: Life by Design: Real Estate Investing with Good Egg's Annie Dickerson 53:15

2M ago53:15

53:15

Join us as we sit down with real estate expert Annie Dickerson, co-founder of Good Egg Investments, to discuss the transformative power of passive income and life by design. Annie shares her journey from teaching to mastering real estate syndications, offering invaluable insights on empowering women in investing, effective communication with invest…

1
EP 111: How Josh Reeves (CEO, Gusto) Built a $10B Company Serving Small Businesses 1:34:05

2M ago1:34:05

1:34:05

Josh Reeves has built Gusto into a nearly $10B company with over $500M in ARR, serving small businesses. In our conversation, Josh delves into Gusto’s 13-year journey, sharing insights on how they achieved product-market fit by initially targeting a very narrow niche. He also highlights the tactics they’ve used to build an intentional culture of hu…

1
178: From High Risk Distressed Debt to the SAFE Method in Self-Storage: Tom Dunkel’s Evolution 39:48

2M ago39:48

39:48

In this episode of Passive Investing from Left Field, I sit down with Tom Dunkel from Belrose Storage Group. We dive into his fascinating journey from the aerospace industry to mastering self-storage investments. Tom shares his insights on the SAFE method for passive investing, the impact of the pandemic on the self-storage sector, and his strategi…

1
177: Green Coffee Company: Revolutionizing the Coffee Industry with Adam Jason 39:30

2M ago39:30

39:30

Join us on Passive Investing from Left Field as we chat with Adam Jason, the entrepreneurial force behind Green Coffee Company. Discover how Adam transitioned from a corporate lawyer to a coffee industry innovator in Colombia, turning coffee byproducts into profitable ventures and aiming for a 5x return on investments. Don't miss this insightful ep…

1
EP 110: How Eric Glyman (CEO, Ramp) Runs One of The Fastest Growing Startups 1:33:52

2M ago1:33:52

1:33:52

Eric Glyman (CEO, Ramp) shared his operating playbook for leading one of the fastest-growing startups on his second appearance on the podcast. We also explored the unique ways Ramp leverages AI internally, strategies for startups to build moats in AI, and the concept of self-driving money. We concluded with one of the most profound and thoughtful d…

1
176: Build Wealth Through Owning a Franchise: Advice from Kim Daly 49:01

2M ago49:01

49:01

Join us in this episode of Passive Investing from Left Field as we sit down with franchise expert Kim Daly. Kim shares her incredible journey from answering a classified ad to becoming one of the top franchise consultants in the industry. Discover how franchising can be a powerful tool for building wealth and achieving financial freedom. Whether yo…

1
175: How to Succeed in Today's Investment Landscape with Whitney Elkins-Hutten 40:16

3M ago40:16

40:16

Join us on the Passive Investing from Left Field podcast as we welcome back Whitney Elkins-Hutten, the Director of Investor Education at PassiveInvesting.com and author of 'Money for Tomorrow'. In this episode, Whitney shares her insights on creating, keeping, and growing wealth, with a focus on multifamily investments, preferred equity, and debt f…

1
EP 109: Sebastian Siemiatkowski (CEO, Klarna) on the Future of Klarna, Valuation Changes and AI in Finance 2:05:57

3M ago2:05:57

2:05:57

Klarna CEO Sebastian Siemiatkowski led the rise from a profitable business to their peak $50 billion valuation, in which they were burning $150 million a month. In my latest episode, Sebastian shares how he turned Klarna back to profitability and discusses Klarna’s ongoing pursuit of creating a digital financial assistant. He also reflects on their…

1
174: Critical Aspects of Limited Partnerships for Smarter Passive Investing with Aleksey Chernobelskiy 43:17

3M ago43:17

43:17

Welcome to the Passive Investing from Left Field podcast! In this episode, we're thrilled to have Aleksey Chernobelskiy, an expert in advising limited partners on real estate investments. Aleksey shares invaluable insights on navigating syndication deals, avoiding common mistakes, and the importance of being an active LP. Whether you're a seasoned …

1
173: The Ins and Outs of Ground-Up Development with Andrew Brewer 41:13

3M ago41:13

41:13

Join host Jim Pfeifer and real estate developer Andrew Brewer as they explore the intricate world of real estate development. Discover the crucial steps, potential risks, and expert strategies for successful property development. Whether you're a seasoned investor or new to the field, this episode offers invaluable insights to help you navigate you…

1
EP 108: Olivier Pomel (CEO, Datadog) Shares Every Lesson From Scaling to $40B 1:32:04

3M ago1:32:04

1:32:04

Olivier Pomel built Datadog into a $40B company while burning only $25M in capital. In our conversation, he shares the fundraising lessons, operating principles, and core insights that made this possible. He also discusses the pros and cons of building a tech company in NYC, how early-career professionals should approach learning AI tools, how Data…

1
172: From Boy Band to Big-Time Investor: Michael Sarracini's Journey 39:52

3M ago39:52

39:52

Join us on "Passive Investing from Left Field" as we dive into an enlightening conversation with Michael Sarracini, a seasoned real estate investor and former boy band member turned entrepreneur. Discover Michael's unique journey from pop stages to property pages and learn how he leverages the three core investing streams to achieve financial freed…

1
EP 107: Steve Kaufer (Co-Founder, Tripadvisor) - Why He Left & What He’s Building Now 1:39:55

3M ago1:39:55

1:39:55

Steve Kaufer led Tripadvisor to multi-billion dollar success over a 20+ year run as CEO. He discusses getting acquired and spun out from IAC, becoming a public company CEO, and his biggest operating lessons from his decades-long journey. Steve also shares behind-the-scenes of his new venture, Give Freely, and reflects on his entrepreneurial path. (…

1
171: The Power of Comprehensive Financial Planning: Insights from Jameson Lett 45:53

4M ago45:53

45:53

Welcome to another insightful episode of the Passive Investing from Left Field Podcast! Today, we're joined by wealth management advisor Jameson Lett, who shares his expertise on comprehensive financial planning, infinite banking, and proactive wealth management. Tune in to learn how you can optimize cash flow, protect your assets, and build long-t…

1
EP 106: How Bill Shufelt (CEO, Athletic Brewing) Built Athletic Brewing - Every Plot Twist Along The Way 1:15:20

4M ago1:15:20

1:15:20

Since 2017, Bill Shufelt (CEO, Athletic Brewing) went from hedge fund trader to the CEO of the leading producer of non-alcoholic craft beer. Unlike the typical tech-focused chats, this one centers around a product many have fallen in love with. In the conversation, Bill tells stories of the unscalable but crucial strategies he used to build a brand…

1
170: The Art of Multifamily Investments: Predictions and Strategies with Ken McElroy 50:40

4M ago50:40

50:40

Join us on the latest episode of the "Passive Investing from Left Field" podcast where our host, Jim Pfeifer, sits down with real estate mogul Ken McElroy. Dive deep into the complexities of property management, the effects of economic shifts on real estate, and Ken’s expert strategies for building and maintaining a successful investment portfolio.…

1
EP 105: Vlad Tenev (CEO, Robinhood): The Meme Stock Crisis, The Future of Crypto, and AI Opportunities in Finance 1:47:23

4M ago1:47:23

1:47:23

In the midst of meme stock craziness, Robinhood CEO Vlad Tenev shared his most eye-opening insights from running the company that transformed the game for retail investors. He talks about Robinhood’s new Gold Card, his views on crypto, the media side, how artificial intelligence could change finance, and more. (00:00) Intro (03:27) The Origin of th…

1
169: Unlocking Financial Freedom: Bala Krishnan’s Investment Journey 50:17

4M ago50:17

50:17

Join us as we delve into the fascinating journey of Bala Krishnan, a tech entrepreneur turned real estate investor. Bala shares his insights on creating exponential wealth through his disciplined 10Y investment model. Learn how he transitioned from tech to ground-up build-to-rent real estate investing, achieving financial independence faster than e…

1
EP 104: Sam Altman (CEO, OpenAI) talks GPT-4o and Predicts the Future of AI 46:30

4M ago46:30

46:30

On the day of the ChatGPT-4o announcement, Sam Altman sat down to share behind-the-scenes details of the launch and offer his predictions for the future of AI. Altman delves into OpenAI's vision, discusses the timeline for achieving AGI, and explores the societal impact of humanoid robots. He also expresses his excitement and concerns about AI pers…

1
168: The Future of Storage: How Automation is Changing the Game with Cliff Minsley 43:23

4M ago43:23

43:23

Join us on the "Passive Investing from Left Field" podcast as we dive deep into the world of real estate with Cliff Minsley, co-founder of Ten Federal. Discover how transitioning from multifamily to self-storage, embracing technology, and innovative strategies have shaped his successful investment approach. Tune in to gain valuable insights on navi…

1
EP 103: The Untold Story of Marcus Ryu (Co-Founder Guidewire & Partner at Battery Ventures) Scaling to $10B and Diving into VC 1:50:28

4M ago1:50:28

1:50:28

After 18 years leading Guidewire (~$10B), Marcus Ryu made the transition from CEO to partner at Battery Ventures. In the episode, Marcus shares his journey of co-founding Guidewire in 2001, steering the company through its IPO in 2012, and building one of the largest vertical software businesses in the world. He shares his insights on how to build …

1
167: Money Myths Busted with a Smile: The Garrett Gunderson Story 45:17

4M ago45:17

45:17

Join us in this insightful episode of "Passive Investing from Left Field" where our host Jim Pfeifer sits down with Garrett Gunderson, an author and financial philosopher, to dismantle the scarcity mindset and explore how adopting an abundance mentality can lead to wealth creation. Dive into discussions on innovative wealth strategies, real estate …

1
EP 102: Armon Dadgar (Co-Founder, HashiCorp) Reflects 48-Hours After Selling to IBM 1:54:42

4M ago1:54:42

1:54:42

After last week’s announcement that IBM is acquiring HashiCorp for $6.4B, HashiCorp co-founder Armon Dadgar discussed a few behind-the-scenes elements of the acquisition and HashiCorp’s full journey from the early days. Armon shares some of his biggest lessons from the journey, from fundraising to community building and more. (00:00) Intro (01:17) …

1
Spotlight: Economic Update with J Scott 17:04

5M ago17:04

17:04

Join us on this spotlight episode of the Passive Investing from Left Field podcast, where our guest J Scott, a seasoned real estate investor and author, shares his valuable insights on the current economic climate, the impact of interest rates, and strategies for navigating the volatile commercial real estate market. Whether you're an experienced i…

1
166: Unlocking Financial Freedom Exploring Unique Investment Niches with MC Laubscher 53:05

5M ago53:05

53:05

Join us on this episode of the Passive Investing from Left Field podcast as we delve deep into the world of alternative wealth strategies with our special guest, MC Laubscher. Discover how to navigate beyond mainstream investments into unique niches like laundromats, fine whiskey, and even strategic metals. Learn from MC's vast experience on managi…

1
EP 101: Andrew Bialecki (CEO, Klaviyo) on Building a $6B Software Company - Klaviyo’s Uncharted Path 1:52:44

5M ago1:52:44

1:52:44

Before Andrew Bialecki took Klaviyo public and scaled the company to $6B, he bootstrapped it to over $1M in ARR. In our discussion, Andrew reveals his philosophies around fundraising, finding the best talent, cultivating entrepreneurship inside Klaviyo, scaling culture, and more. (00:00) Intro (01:13) Klaviyo's Bootstrap Beginnings (09:37) The Stra…

1
Spotlight: Money Ripples with Chris Miles the Anti-Financial Advisor 25:39

5M ago25:39

25:39

🎙️ Welcome to a spotlight episode of "Passive Investing by Left Field Investors"! Today, we're excited to feature a podcast swap with "Money Ripples with Chris Miles." Chris Miles, known as the anti-financial advisor, and his community focus on investments in real assets that generate real cash flow, aligning closely with our philosophy here at Lef…

1
165: Interest Rates, Inflation, and Economic Trends: Insights from Peter Linneman 47:01

5M ago47:01

47:01

Join us on this enlightening episode of "Passive Investing from Left Field" as our host Jim Peifer sits down with the renowned economist, Professor Peter Linneman. With decades of experience and wisdom, Peter shares his unique insights on the current economic climate, including the real impact of interest rates, the truths behind inflation rates, a…

1
EP 100: Jeremy Levine (Partner, Bessemer) Reflects on His Best and Worst Investments 2:44:43

5M ago2:44:43

2:44:43

After 23+ years in venture capital, Jeremy Levine has thrived in many eras, taking risks on now-iconic companies like LinkedIn, Shopify, Yelp, Pinterest, and more. In our discussion, Jeremy shared stories behind these investments and the mindsets he’s developed along the way. We also explored how the VC landscape has evolved over the last 20 years …

1
164: From Crisis to Creativity: Real Estate Strategies for the Modern Investor with Neal Bawa 58:20

5M ago58:20

58:20

Join us on this enlightening episode of the Passive Investing from Left Field podcast, where we dive deep into the multifaceted world of real estate investment in a post-COVID era. Our guest, Neil Bawa, the mad scientist of multifamily, shares his invaluable insights on the impact of COVID-19 on multifamily investments, the dramatic shift in office…

1
EP 99: Garret Langley (CEO, Flock Safety) - The $4B Tech Startup Solving Crime with AI 1:47:45

5M ago1:47:45

1:47:45

Garrett Langley is the CEO of Flock Safety, a $4B company helping solve 10% of US crimes with AI-powered tech. Garrett offers an in-depth look into Flock Safety’s ambitious vision to eliminate crime in America and all the operating lessons he’s learned along the way, including how to build a strong and motivated team, keep people accountable, and l…

1
163: Multifamily Mastery: Brian Burke on Surviving Market Cycles 1:01:00

5M ago1:01:00

1:01:00

Join us on this enlightening episode of the Passive Investing from Left Field podcast, where we dive deep with Brian Burke, president and CEO of Praxis Capital. With over $800 million in real estate acquisitions, Brian shares his seasoned perspective on navigating the unpredictable real estate market, preserving capital, and strategizing investment…

1
Daniel Powter l Canadian Singer-Songwriter, Canada's Got Talent Season 3 Contestant 30:23

5M ago30:23

30:23

Raised in Coldstream near Vernon, BC, his hit single soared to number one in France along with over forty other worldwide markets, finally reaching the hottest song for six weeks in the US. Canadian singer-songwriter and Canada’s Got Talent season 3 contestant Daniel Powter speaks with Jigme about his experience on Canada’s Got Talent, the positive…

1
EP 98: Sanjit Biswas (CEO, Samsara) on Building to $20B: The CEO Behind One of The Fastest Growing Startups Ever 1:24:20

6M ago1:24:20

1:24:20

In less than 8 years, Sanjit Biswas scaled Samsara from 0 to over $1B ARR. In our latest conversation, Sanjit shares all the lessons he’s learned about running a hyper-growth organization, including all the changes he’s made since growing and selling his first company Meraki to Cisco for $1.2B and going on to scale Samsara to $20B. A great episode …

1
162: The Evolution of Real Estate Investing: A Conversation with James Eng 1:01:06

6M ago1:01:06

1:01:06

Join us on this exciting episode of the Passive Investing from Leftfield podcast as we dive deep into the world of multifamily investing with James Eng, the professor of Multifamily Financing. Discover the latest trends, strategies, and insights into the future of real estate investment. Whether you're a seasoned investor or just starting out, this…

Podcasts Worth a Listen

Left Field Investors Podcasts

Podcasts Worth a Listen

Quick Reference Guide