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Community Support in Search

Guesswork Investing
Guesswork Investing
Big Deal Small Business: Community Support in Search
August 25, 2022 | Issue #71
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It’s been over a month since my last newsletter post, so if you signed up in the intervening period, a quick reminder – I’m a PE investor turned self-funded searcher turned SMB operator. As the “President” of a home services business, I’m really a general manager just trying to keep the wheels on the bus week-to-week. This newsletter is meant to provide a ride-along experience for you.
That said, as I’ve gone through those transitions over the past 18 months, the newsletter audience has grown as well (now just shy of 1,800). It’d be helpful if you could please fill out a 5-question survey for me (will take <2 mins).
I just want to check in and see what the reader base looks like today and what kind of writing is interesting & useful to you.

Community Support in Search
Search can be broadly broken up into three phases: pre-search/info gathering phase, search phase, and operating phase.
One consistent dynamic throughout – each phase is lonely.
Your existing peer & friend group, while great, is in a very different track for the most part. They are saving money, buying houses, buying cars, funding 401Ks, etc.
Meanwhile, you’re burning cash on rent and diligence costs for deals that end up dying.
The steady W-2 is a great track and makes sense for most people (including being very viable for most searchers).
As a result, it’s hard for them to make sense of search. You need like-minded folks just crazy enough to leave the W-2 world behind.
Why have a group?
Most successful searchers I’ve met have had a stable of 4-8 thought partners – other searchers, operators, investors, etc. These people serve as a sounding board as your search meanders through different industry theses, location focuses, and more.
More importantly, this group also helps you get off the mat when the search is particularly shitty.
During pre-search phase, they can help you break through the “quit your job” decision.
During the search phase, they can help you start searching again after a deal dies with $50K of dead deal costs.
During the operating phase…I feel like my group helps me every week. So many things go wrong in small business operations.
In my search, I’ve been super lucky to have a strong group that meets every other week for ~2 hours. We’ve had biweekly Zoom calls for roughly 18 months now…I think we’ve skipped maybe 2 calls total over that period. A couple people have filtered in or out, but for the most part it’s been a very steady group.
Since we formed the group, people have stopped searching, they’ve closed on deals, they’ve exited deals…the whole gamut.
Group Structure
To make weekly or monthly calls useful, it’s ideal to have a diversity of experiences & opinions in your group.
This can include diversity of identity (can be tough in search world given how male & white it happens to be, so breaking out of that requires some conscious effort).
This can include variety of backgrounds (PE, operations, military, consulting, etc.), as each person brings a different set of skills to the table.
From personal experience, one of the most helpful has been working with folks at different stages of search. Ideally you can build a group that has some people early in search, some “grizzled veterans” on month 22 of search, some operators early in their deal, some operators 3-4 years into their deal. Maybe even someone who has exited their company.
These people can help put things in context thanks to their experience (how many deals to look at in a week, what normal deal terms are, how much to actually care about the seller note personal guarantee…). They’ve made the decisions you have to make now, and they’ve seen the consequences of them.
Obviously if you’re on the more “junior” end of that list, part of being a member of the community is paying it forward in the future as you grow & make progress.
In terms of communication structure, once per two weeks or once per month seems like a sweet spot. Enough has transpired between meetings and it’s not too time-consuming, but still often enough to maintain the thread.
I’d also built out a Slack channel for your team for random one-offs, questions, anecdotes, etc. There are searcher Slack groups out there, but I have found them (and websites like Searchfunder) a bit too broad / basic to be helpful. Building a core support team of 4-8 people in one Slack or text threads will result in much more detailed & specific advice for you.
To be clear, I’m suggesting a very organized version of a group – it can also work to just have a few contacts that you have 1:1 calls with every couple weeks or so. Don’t need to overcomplicate it, just find your people.
How To Find a Group
I found my group through Twitter. It continues to be the most powerful tool I’ve seen for SMB networking (and in SMB world, networking feels more like making actual friends).
I’d encourage you to put out tweets or DM folks to try to build out that group. My group was formed by one person tweeting about the idea and posting a Google form - I’d never even met him before, but I signed up and it’s become a core foundation of my search journey.
There are some more organized versions of this, such as search fund accelerators or Steve Ressler’s new Brydon Group.
One of the best I’ve seen is Pursuant Capital’s Search Fund Bootcamp. In addition to training, it builds an automatic cohort for you and gives you access to Sam Rosati, a super experienced searcher & search investor. They’re launching their next Bootcamp in early November, so check that out:
Pursuant Capital
Search Fund Bootcamp (November 2nd – 4th, 2022) – Applications Open!

Applications are now open for Pursuant Capital's next Search Fund Bootcamp. The Bootcamp is a 3-day, intensive, in-person training course with Pursuant, its Deal Team
Don’t try to do this alone. I guess you could, but why? Give yourself the tools to succeed, and that starts with a support group that understands what you’re doing.
Just a reminder, please fill out the 5-question audience survey so that I can hear more about what you’re interested in for the future.
As always, I’d love to hear your thoughts, so just hit reply to this email or find me on Twitter.
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