In this episode of Acquisition Collective, Jay Bourgana interviews Chandra Rao about his journey from rookie deal to $17,000,000 in revenue. What started as a risky first purchase turned into a masterclass on business acquisition, culture, and scaling.
From losing $300K in year one, to uncovering fraud, to building systems that generate consistent cash flow, Chandra shares what every entrepreneur and business buyer must know before making their first deal. This is a blueprint for operators who want sustainable growth in M&A and long-term entrepreneurship.
We talk about how to:
✅ Avoid rookie mistakes in business acquisition
✅ Spot red flags in sellers during due diligence
✅ Build company culture that attracts top talent
✅ Scale revenue across multiple acquisitions
✅ Balance growth, family, and entrepreneurship
✅ Position for the $17M milestone (and beyond)
If you’re serious about M&A, entrepreneurship, and scaling revenue, this is a must-watch.
Timestamps
00:00 From Oracle to Startup Rocketship (Coupa $50M → $20B)
02:00 The Rookie Deal: $500K Electrical Contractor at 1x EBITDA
05:00 Losing $300K in Year One—And the Lessons Learned
10:00 Seller Fraud, IRS Issues, and Why Culture Matters
15:00 Scaling Through 3 Acquisitions in 2020 (During COVID)
22:00 Burning Out While Balancing W-2 + Business Acquisition
28:00 The Trailer Manufacturing Disaster ($1M Burned in 1 Year)
37:00 Buying Out a Toxic Partner & Rebuilding Company Values
44:00 The $4.4M Electrical Services Deal (Best Acquisition Yet)
50:00 Why EOS + Culture Transformed the Companies
53:00 The $17M Revenue Milestone and Next Growth Phase
59:00 Key Advice for Entrepreneurs and Business Buyers
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Linkedin: https://www.linkedin.com/in/chandrasrao/
