He Built 550 Units Before Quitting His Day Job. Here’s the Playbook.

He Built a 550-Unit Portfolio While Working Full-Time. Then He Merged With His Co-GP to Scale Even Faster.

Jaideep Balekar started investing while working a demanding job at Deloitte. Four years later, he had built a 500-plus unit portfolio, raised over $15 million, and stepped into full-time real estate with confidence and cash flow.

For years, Jaideep underwrote deals after hours, took investor calls on weekends, and leveraged a high-income W2 to fund his early acquisitions. He built strong co-GP relationships, self-managed units, and developed a conservative approach that helped him stay disciplined through market swings.

Today he’s the co-founder of Prosper Capital, with 550 units under management, in-house operations, and a platform built for long-term cash flow over headline growth.

The Play: Buy B and C Class Value-Add, Control Operations, and Underwrite Conservatively

Jaideep didn’t try to flip his way into syndication. He started with an 8-unit property in Cincinnati, self-managed with his wife, and learned the fundamentals hands-on. Over time, he expanded into 30- to 100-unit buildings and formed JV and co-GP partnerships to take down bigger deals.

He focuses on:

• 20 to 100 unit deals in stable, landlord-friendly markets

• Properties with deferred maintenance or poor management

• Deals where vertical integration can unlock NOI and reduce risk

He doesn’t chase the next hot market. He builds for cash flow, and lets compounding do the rest.

Why This Works

1. He scaled before he stepped out
Jaideep waited until his real estate income covered his living expenses before quitting Deloitte. That gave him the leverage to say no to bad deals and stay selective.

2. He brought operations in-house
With property management and construction handled internally, Prosper Capital controls timelines, budgets, and tenant experience more tightly than third-party managers ever could.

3. He used JVs to get started
Jaideep’s first large deals weren’t full syndications. He partnered with trusted operators, shared economics, and built confidence before taking on full raises.

The Risks (and How He Managed Them)

• Insurance gaps: A city sewer backup caused over $100K in damage to a renovated asset. Insurance only covered a fraction. Instead of suing the city, he covered the loss, stabilized the asset, and exited profitably.

• Capital limitations: After depleting personal funds, he began raising from LPs but always focused on transparency and downside planning to avoid overpromising.

• Team fatigue: Scaling fast can burn out lean teams. Jaideep merged with a co-GP he had done three deals with, forming Prosper Capital to centralize operations and extend his bandwidth.

What You Can Learn (and Steal)

1. Grow the portfolio before you go full-time
Jaideep didn’t make the leap until the numbers made sense. That gave him clarity and confidence — and a real margin for error.

2. Leverage JVs as your first capital stack
If you’re not ready to syndicate, partner with one or two experienced GPs and share the upside. Trust and alignment matter more than structure.

3. Build the ops engine early
You don’t need to vertically integrate on day one, but the sooner you bring construction or PM in-house, the faster you’ll build a defensible platform.

Listen to the full episode

🎙 Groundbreakers with Jaideep Balekar

In it, we cover:

• How Jaideep built a 550-unit portfolio while working at Deloitte

• Why he waited until he had cash flow before quitting his job

• The biggest deal mistake he made and what it taught him

• How vertical integration is helping his team scale more efficiently

• What newer GPs get wrong when raising from LPs