How Christopher Lento Went from House Hacking to Building a $100M Real Estate Portfolio

How Christopher Lento Went from House Hacking to Building a $100M Real Estate Portfolio

The fifty-fourth episode of Groundbreakers Podcast by Homebase! Listen in for an amazing interview with Christopher Lento, Founder & CEO of EM Capital.

Domingo Valadez

Mar 18, 2025

Podcast

Episode Summary

In this episode of Groundbreakers, Chris Lento, founder of EM Capital, shares how he scaled from small house hacks in Boston to building a $100M+ real estate portfolio. Starting with a mechanical engineering degree and a career in aerospace, Chris realized that real estate offered a better path to financial freedom. Over time, he transitioned from self-managing triplexes to leading large syndications across the Southeast. His story is a masterclass in scaling, raising capital, and making smart investment pivots.

To listen to this episode, follow this link to Groundbreakers on Spotify!

Key Points Discussed

• From House Hacking to Syndications – Chris started by living in his own rental properties while fixing them up. Over the years, he transitioned to larger deals and raised outside capital to scale.
• The Challenge of Raising Capital – Even when investors verbally committed, getting them to wire funds was a different story. Chris shares how he overcame this hurdle.
• Picking the Right Markets – He explains why North Carolina and Florida are prime locations for long-term real estate growth.
• Red Flags in Partnerships – Chris highlights the warning signs he looks for in potential business partners, including defensiveness and lack of transparency.
• Lessons From Managing $100M+ in Assets – Chris shares the biggest takeaways from his journey, from property management struggles to executing complex condo conversions.

Guest Information

• Name: Christopher Lento
• Role: Founder & CEO at EM Capital
• LinkedIn: Christopher Lento
• Website: EM Capital

Conclusion

Chris Lento’s story proves that real estate is a long game, and strategic scaling is key. From house hacking to syndications, his journey offers invaluable lessons for investors looking to grow beyond small rentals.

DOMINGO VALADEZ is the co-founder at Homebase and a former product strategy manager at Google.