New Podcast: From Wall Street to Main Street—Why He Left Private Equity to Roll Up Tree Care Companies

Hello SMB Deal Hunters!

I’m excited to share a new interview with Kaustubh Deo, an entrepreneur rolling up tree care businesses in Seattle, Washington.

After a few years in private equity, Kaustubh made the leap into small business acquisitions—starting with his first deal in 2022 using a combination of SBA 7(a) financing, seller financing, and investor capital. Since then, he’s added two more companies to his platform.

If you’re curious about how to transition from Wall Street to Main Street or scale through add-on acquisitions, this one’s for you.

Today's issue is sponsored by SMB Diligence, the platform I helped start for matching business buyers with vetted legal counsel and Quality of Earnings providers.

COMMUNITY WINS

Here’s what one SMB Deal Hunter Pro member shared this past week:

Want me and my team to work with you to find, finance, and acquire a million-dollar cash-flowing business in the next 6-12 months?

👉 Learn More and Book A Call

INTERVIEW

This episode is packed with actionable insights for anyone looking to buy their first business or build a roll-up. We dive into:

• Why Kaustubh left private equity at 28 to become an operator

• How to identify your edge in the small business M&A process

• The tree care services that drive repeat revenue and command premium pricing

• Structuring a deal where investors funded most of the down payment

• How he keeps investor relations simple and effective

• Navigating the owner transition as a first-time buyer

• Modernizing quoting—from pen and paper to CRM

• Balancing organic growth with acquisitions

• How he financed his tuck-in deals

• And a lot more along the way

👉 Watch the full 48-minute interview with Kaustubh Deo

PRESENTED BY SMB DILIGENCE

Here’s Why You Shouldn’t Skip Due Diligence…

A friend of mine put a business under LOI and asked me for my advice.

I recommended he contract a 3rd party due diligence partner to rebuild the company's P&L from scratch.

Turns out their EBITDA was off by 2x 😳

Enter SMB Diligence.

SMB Diligence is the platform I helped start for matching business buyers with vetted diligence providers, from M&A lawyers to Quality of Earnings providers.

Their network of experts has worked on hundreds of small business transactions (including many from the SMB Deal Hunter community).

👉 Get introduced to due diligence experts today

COMMUNITY PERKS

• Ready to buy and operate a $1M+ business? Get expert help at every step.

• Want to invest passively in SMB acquisitions? Get access to investment opportunities.

• Get a personal introduction to my preferred SBA 7(a) lender, non-SBA lenders, Quality of Earnings providers, or legal counsel

• Raising capital for your deal? I’ll connect you with investors from the SMB Deal Hunter Community.

• Interested in selling your business? I’ll help you connect with buyers from the SMB Deal Hunter Community.

THAT’S A WRAP

Want me to interview you for my podcast? Hit reply.

See you tomorrow with some new deals!

-Helen Guo
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Disclaimer

This publication is a newsletter only and the information provided herein is the opinion of our editors and writers only. Any transaction or opportunity of any kind is provided for information only; SMB Deal Hunter does not verify nor confirm information. SMB Deal Hunter is not making any offer to readers to participate in any transaction or opportunity described herein.