HeyJaredBig Deal Small Business
Thinking about buying a small business? I’ve done it (3 times now) — and I share my strategies, mistakes, and frameworks. I aim to bridge my former Private Equity life to the Main Street world in a way that's approachable, interesting, and educational.
- Indexed issues, last 90 days
- 9
- Latest publication
- Sep 21, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 6, 2026
Latest issues
Why can’t I be Rob Brooks? (opens the original)
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This is a blog written by Kaustubh Deo // Guesswork Investing about acquiring & operating small businesses. If you are a new reader / new searcher, please start here.If you enjoy this blog, two asks:Consider upgrading to a paid subscription, which includes more in-depth small business operating contentShare this with 1-3 friends who may find it useful<a class="button primary" href="https://bigdealsmallbu
Quarterly Planning in a Small Business (opens the original)
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This post starts with a preview, but has paywall further down. It is primarily written for small business owner-operators doing $1mm to $10mm of revenue. Please consider supporting my writing as a paid subscriber, and hopefully you’ll find a ton of value for your own business.Subscribe nowQuarterly Planning in a Small BusinessWe recently crossed a remarkable milestone at Blooma – we had our first real quarterly planning meeting. We convene
Risk Assessment Protocols (opens the original)
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This is a blog written by Kaustubh Deo // Guesswork Investing about acquiring & operating small businesses. If you are a new reader / new searcher, please start here.If you enjoy this blog, two asks:Consider upgrading to a paid subscription, that covers more in-depth small business operating contentShare this with 1-3 friends who may find it useful<a cl
Blooma Operating Update (August 2026) (opens the original)
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This post starts with a preview, but has paywall further down. It is primarily written for small business owner-operators doing $1mm to $10mm of revenue. Please consider supporting my writing as a paid subscriber, and hopefully you’ll find a ton of value for your own business.Blooma Operating Update (August 2026)Periodically, I update you on my day-to-day as the owner-operator of a small business. Whether you’re a new reader or you’ve been along for the ride since the beginning, you may find thi
Handshakes to Hugs (opens the original)
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This is a blog written by Kaustubh Deo // Guesswork Investing about acquiring & operating small businesses. If you are a new reader / new searcher, please start here.Quick note: My good friend (and podcast co-host) Sam Rosati is bringing his flagship SMBootcamp LIVE to Denver this September 9-11, alongside Adam Markley of PROX Search Capital. 3 days of in-person training to accelerate your search. I’ve heard great fe
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