Read Me First

Welcome to Big Deal Small Business.

This is the place for you if you’re considering buying a small business, if you already own a small business, or you want to invest in small business. Thanks for being here.

Who writes this?

This Substack is written by Kaustubh Deo, though I’ve historically used the pen name Guesswork Investing. I’ve been writing this Substack since 2021 after I switched from being a private equity investor to a searcher. Since then, I’ve acquired a small business myself, invested in three other search deals, and acquired two add-on acquisitions for my business.

Here’s a quick intro on how to use this Substack:

• If you read nothing else, please read SDE vs EBITDA vs Cash Flow. It’s me on my soapbox on how searchers, investors, and operators should be analyzing small business financials.

• If you only subscribed to the free version of my Substack, you will receive posts (roughly 1-2x per month) to your inbox that are more focused on searching, buying, and investing. You’re in the right place.

• If you’re considering becoming a searcher (aka finding a small business to buy), start with the New Searcher Reader Guide. It’s filled with links to get the ball rolling as you research the space.

• If you’re looking for great deal team support in acquiring your business, I’ve put together a list of trusted vendors.

• If you already own a small business, please consider subscribing to the two operator-focused sections:

  • Guesswork Unveiled: This is the paid section (roughly 2-4x per month in addition to the free posts), which involves more in-the-weeds thoughts on small business operations. It also discusses add-on acquisitions for your business.

  • 25-Day Business Owner Challenge: Start on Day One, and try to knock out each challenge each day. These are small actions you can take to get the flywheel turning in your business. 1% improvements everyday.

• If you want to join the SMB Twitter community (aka SMBTwit), check out this list of accounts I made for you to follow — these are real small business buyers & operators talking about their lives. That list will get you in the flow of things right away. And you can follow me as well (@GuessworkInvest)!

Thanks for supporting my writing, and feel free to email me anytime with questions or comments. You can reach me at admin(at)guessworkinvesting(dot)com.

Thanks,

Kaustubh Deo // Guesswork Investing