Matt Ober, Managing Partner at Social Leverage, joins Jake & Gino to discuss venture capital, fintech investing, data-driven investing strategies, AI, entrepreneurship, and the future of finance.

Previously Chief Data Scientist at Third Point and Head of Data Strategy at WorldQuant, Matt shares valuable insights into startup investing, identifying market opportunities, and how technology is transforming the financial world.

In this episode:

Looking to grow your real estate investing business with proven systems and education? 

Visit Wheelbarrowprofits.com and start building long-term wealth today.

timestamps

0:05 - Introduction by Jake Stenziano

0:13 - Gino responds to Jake

0:18 - Jake's comment on gratitude

0:21 - Gino talks about yesterday's conversation

0:49 - Gino acknowledges Jake's support

1:07 - Discussion about the weather

1:23 - Introduction of guest Matt Ober

1:52 - Matt Ober's introduction

2:01 - Matt shares his career journey

2:30 - Matt talks about his hedge fund experience

2:58 - Discussion on venture firm building

3:28 - Matt talks about his partners

3:37 - Matt discusses the hedge fund space

4:05 - Jake comments on the hedge fund space

4:31 - Matt talks about his current company

5:11 - Discussion on investment thesis

5:30 - Matt explains investment focus

6:29 - Matt talks about investing in people

7:06 - Discussion on adversity and entrepreneurship

7:39 - Jake asks about investing in trust funds

8:28 - Matt discusses work atmosphere

9:05 - Discussion on investment backgrounds

9:35 - Matt talks about global team experience

10:24 - Discussion on competition and relationships

11:00 - Discussion on wealth management

12:16 - Discussion on gambling and prediction markets

13:28 - Discussion on prediction markets as media

14:05 - Discussion on tax loss harvesting

15:17 - Discussion on investment strategies

16:02 - Discussion on borrowing against stock portfolios

17:10 - Discussion on interest rates and loans

18:04 - Discussion on democratizing financial tools

19:24 - Discussion on data and AI

20:55 - Discussion on company adaptation to AI

22:06 - Discussion on layoffs and efficiency

23:26 - Discussion on AI and job skills

24:09 - Discussion on investment lifecycle

25:13 - Discussion on venture scale

26:24 - Discussion on raising capital

27:45 - Discussion on investment success rates

29:10 - Discussion on investment distribution

30:18 - Discussion on timing and product success

31:14 - Discussion on founding teams

32:09 - Discussion on founder challenges

33:25 - Discussion on business similarities

34:25 - Discussion on AI and creativity

35:24 - Discussion on creativity and skills

36:27 - Discussion on AI usage

37:49 - Discussion on sales and networking

38:26 - Discussion on commercial real estate

39:16 - Discussion on loan processes

40:38 - Discussion on real estate debt space

41:06 - Discussion on mortgage processes

42:32 - Discussion on financial planning

43:00 - Discussion on 401k transfers

43:59 - Matt's bold prediction

44:42 - Closing remarks

We're here to help create real estate entrepreneurs... 

 About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Real estate moves in cycles — and understanding where we are in the market can completely change the way you invest.

In this episode of How To from Jake & Gino show, Gino breaks down the four phases of the real estate cycle, how investors should think during each stage, and the biggest mistakes people make when they ignore market timing.

Whether you're buying your first deal, scaling a portfolio, or trying to understand today’s market conditions, this episode will help you recognize opportunities before everyone else does.

00:00 Introduction

This episode is sponsored by Wheelbarrow Profit.

We're here to help create real estate entrepreneurs... 

 About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

What if the way you communicate is the biggest factor shaping your success?

In this episode of Jake & Gino Podcast, we sit down with bestselling author and communication expert Carmine Gallo to break down why storytelling and clear communication are essential skills for leaders, entrepreneurs, and anyone looking to make an impact.

Carmine—author of Talk Like TED, The Bezos Blueprint, and Viral Voices—shares powerful insights on how the most influential people in the world craft messages that inspire action at scale. From boardrooms to global stages, the principles of great communication haven’t changed—the platforms have.

In this conversation, you’ll learn:

Whether you're an entrepreneur, investor, content creator, or leader, mastering communication can transform your results—and your relationships.

🎯 The principles haven’t changed. The platforms have. Are you ready to be heard?

We're here to help create real estate entrepreneurs... 

 About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Before you focus on making money, you need to learn how to protect it.

In this episode, Gino shares key principles to minimize risk, avoid common investing mistakes, and build a solid foundation for long-term wealth.

Want to learn how to invest in real estate and build long-term wealth?

Learn more: https://wheelbarrowprofits.com

0:00  Introduction to asset ownership and estate planning statistics.

0:27  Discussion on estate planning and baby money soldiers.

0:55  Introduction of Gino Barbaro and the concept of baby money soldiers.

1:31  Importance of protecting and perpetuating wealth.

1:59  Personal story about asset protection and LLCs.

2:28   Explanation of entity protection and legal advice.

2:57   Importance of consulting with an attorney.

3:25  Considerations for keeping assets in personal name.

3:52  Importance of legal advice and using AI for initial guidance.

4:18  Introduction to insurance and its importance.

4:48  Using AI to understand insurance policies.

5:14  Ensuring for catastrophic losses.

5:40  Example of adjusting car insurance deductibles.

6:07  Explanation of insurance deductibles and savings.

6:31 Importance of ensuring for catastrophic events.

7:01 Discussion on insurance claims and premiums.

7:28  Importance of life insurance for the general of the army.

7:44  Explanation of term and whole life insurance.

8:12  Introduction to buy-sell agreements.

8:42  Personal story about buy-sell agreements.

9:10 Explanation of key man insurance.

9:39 Importance of key man insurance for business continuity.

10:10 Introduction to umbrella policies.

10:39 Importance of reviewing insurance policies.

11:07 Transition to estate planning.

12:23  Importance of having an estate plan.

12:46 Explanation of legacy and estate planning.

13:14 Components of an estate plan.

13:41 Importance of a last will and testament.

14:09 Additional estate planning tools.

14:35  Explanation of revocable trusts.

15:02 Importance of avoiding probate.

15:32  Exercise on understanding personal finances.

15:55 Importance of high deductibles and financial independence.

16:23 Conclusion and contact information.

We're here to help create real estate entrepreneurs... 

 About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode, Jake and Gino sit down with Greg Mohr, Wall Street Journal bestselling author and founder of Franchise Maven®, to discuss how franchising can create predictable, recession-resistant cash flow.

Greg shares how his 10-Operator Rule™ helps investors acquire manager-run businesses, allowing them to scale income without being involved in daily operations. If you're looking to diversify beyond real estate and build multiple income streams, this episode is for you.

🔗 Learn more: https://www.franchisemaven.com/

💼 This episode is sponsored by Wheelbarrow Profits
https://wheelbarrowprofits.com

Greg Mohr's Background - 0:43

First Franchise Experience - 3:18

Franchising vs. Private Business - 4:20

Real Estate and Franchising - 6:10

Essential Services in Franchising - 16:46

Evaluating Franchises - 18:07

10 Operator Rule - 20:31

Franchise Fees and Costs - 28:54

Successful Franchise Stories - 37:13

We're here to help create real estate entrepreneurs... 

 About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode of the Jake & Gino How To Series, Gino shares a practical guide on how to invest your money with intention.

Beyond just chasing returns, this conversation focuses on protecting your capital, building sustainable income streams, and creating long-term wealth. Gino also highlights the importance of side hustles as a way to generate additional income that can be reinvested into assets.

Timestamps

00:00 – Introduction

This episode is brought to you by Wheelbarrow Profits.

We're here to help create real estate entrepreneurs... 

 About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode of the Jake & Gino Podcast, we sit down with Marcus Higgins, a seasoned operator with a proven track record in scaling high-growth hospitality and consumer brands. Marcus previously led U.S. operations for OYO—one of the fastest-growing hospitality companies in the world—and now brings his expertise to Landing, a company revolutionizing the way people experience flexible, mid-term living. 

If you're interested in real estate, multifamily trends, or innovative housing models, this is an episode you don’t want to miss. 

Connect with Marcus & Learn More 

Landing Website: https://www.hellolanding.com/ 

Partner with Landing: https://www.hellolanding.com/partner 

LinkedIn: https://www.linkedin.com/company/hellolanding/ 

This episode is brought to you by Wheelbarrow Profits. Learn more about their proven framework for financial freedom through multifamily real estate: 👉 https://wheelbarrowprofits.com/ 

We're here to help create real estate entrepreneurs... 

 About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Why do so many people feel stuck financially, even when they’re making money?

In this episode, Gino breaks down the core principles you need to understand to stop living paycheck to paycheck. He introduces the concept of “baby money soldiers” as a simple way to visualize how money flows in and out of your life—and why most people struggle to build wealth.

By understanding income types, expenses, and financial behavior, you can begin to take control and build a more intentional financial future.

This episode is sponsored by Wheelbarrow Profits

TIMESTAMPS

00:00 – Introduction

We're here to help create real estate entrepreneurs... 

 About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

How do you scale a property management business while maintaining service quality and operational efficiency?

In this episode of the Jake & Gino Podcast, Gino Barbaro sits down with Mike Steward, Vice President of Real Estate Sales at Real Property Management.

With over 18 years of experience across real estate, construction, and property management—and a background as President and COO of a Sotheby’s International Realty franchise—Mike shares proven strategies to help operators grow door count, increase market share, and reduce churn.

This conversation dives deep into the systems, metrics, and leadership principles required to scale a property management company in today’s competitive landscape.

This episode is brought to you by Wheelbarrow Profits

00:00 – Intro

We're here to help create real estate entrepreneurs... 

 About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode of How To Show, Gino Barbaro shares a powerful mindset shift for real estate investors: sometimes, slowing down is the fastest way to scale.

Drawing from his own journey, Gino breaks down the early stages of his real estate career and explains how taking a more intentional, strategic approach helped him grow a stronger and more sustainable portfolio. From avoiding costly mistakes to focusing on long-term wealth, this episode is packed with actionable insights for both new and experienced investors.

If you’re looking to grow your real estate portfolio the right way, this conversation will help you rethink your pace, your strategy, and your path to success.

👉 Learn more and access valuable resources at: wheelbarrowprofits.com

We're here to help create real estate entrepreneurs... 

 About Jake & Gino: Jake & Gino are multifamily investors, operators, and owners who have created a vertically integrated real estate company. They control over $350M in assets under management. Connect with Jake & Gino here --> https://jakeandgino.com.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.