Guesswork Investing is no longer anonymous! Re-introducing myself.

searcher profile

January 20, 2025

by a searcher from University of Pennsylvania - The Wharton School in Seattle, WA, USA

Hi there,

I've been a member of the search community for 5+ years, starting with an investment in a self-funded search deal back in###-###-#### Since then, my online presence has been anonymous for privacy reasons. I'm finally yanking that cover off as I get deeper into this world and want to integrate my working life with my search community life.

I write the blog Big Deal Small Business on Substack, historically under the pseudonym Guesswork Investing (same as my Twitter profile). The blog discusses all things search, including small business acquisitions, investing, and operations. It now reaches 8K+ readers that seem to enjoy it, so please do check it out if you're curious.

In my day-to-day, I own & operate Blooma Tree Experts, a tree services contractor in Seattle that I acquired in 2022 through a self-funded search. Since then, I've acquired two add-on acquisitions as well. I've also invested in three self-funded search deals, so I'm active on that side as well.

In any case, looking forward to re-engaging with the search community under my real name!

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commentor profile
Reply by a searcher
from Massachusetts Institute of Technology in Austin, TX, USA
I have been reading your content for the last few months as I get ramped up on search and really enjoying it, thank you so much for what you share and put out into the world! My favorite so far that I've referred back to many times is this one on meeting the seller https://bigdealsmallbusiness.substack.com/p/meeting-the-owner###-###-####
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Reply by a searcher
from The University of Michigan in Snohomish, WA, USA
Love all the content you post on Substack! I've referred back to certain posts many times on there - like this one: https://bigdealsmallbusiness.substack.com/p/sde-vs-ebitda-vs-cash-flow-updated Thanks for all you do to help the ETA community including hosting local happy hours in Seattle.
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