Deep Dive: Questions Every Searcher Must Answer Before They Chase a Deal
Key Takeaways
Before you model IRRs or build a pipeline, you have to decide if youʼre willing to restart your net-worth story from zero and live with years of concentrated risk.
Search is a lifestyle choice. Youʼre buying a job, a calendar, and a set of problems, not just a P&L.
The best searchers are honest about what they want their life to look like in 3- 7 years.
Getting clear on these questions early will save you from raising a fund, signing an LOI, or closing on a business that doesnʼt actually fit the person you are.
Most people step into a search through a spreadsheet. The pitch decks show smooth curves, modest leverage, and happy owners withdrawing six-figure salaries from sleepy, defensible businesses. Itʼs an attractive story: skip the zero-to-one grind, buy cash flow, and compound for a decade.
But that story skips the part where you stake your best years and most of your net worth on a single, illiquid bet that lives in a town you didnʼt pick, with employees you didnʼt hire, serving customers you donʼt yet know.
The searchers who end up glad they did it arenʼt braver or smarter. Theyʼre clearer. Before they raise a dollar or talk to a broker, they sit with a smaller set of uncomfortable but essential questions. If you get those answers wrong, no amount of sourcing, diligence, or post-close heroics will fix the mismatch.
Here are the four questions to ask yourself as a searcher, before the first LOI ever goes out.
Are you willing to start your net-worth story from scratch?
You may go from a diversified portfolio and stable salary to one illiquid asset and variable cash flow. For several years, almost all incremental savings and upside will flow into this single bet. Your personal identity will get tied to how this company performs.
If the thought of watching friends climb corporate ladders while your net worth stalls or even dips for a few years feels unbearable, thatʼs useful information.
Are you willing to carry the weight of risk once it stops being theoretical?
Decks talk about downside cases. Term sheets talk about covenants. But in practice, risk shows up as 3 a.m. worries, hard conversations, and the sick feeling when a key customer calls to say theyʼre going out to bid.
Before you search, ask:
Am I truly okay with personal guarantees, leverage, and lender oversight in my day-to-day emotional life?
How will I react the first time revenue misses budget by 20 percent, or a lender asks for an extra report because theyʼre nervous?
Can I live with the reality that some factors, like macro shocks, industry shifts, and a key employeeʼs health, will always be outside my control?
Do you actually want the operatorʼs calendar?
Itʼs easy to love “being a CEOˮ in the abstract. Itʼs harder to love what CEOs of €2-€5M EBITDA companies actually do all day. That often includes:
Hiring, firing, and coaching people who didnʼt choose you and may not want change.
Sitting with messy customer issues, late shipments, vendor disputes, and small-dollar operational headaches.
Spending meaningful time in warehouses, job sites, or service routes.
Will this chapter make sense in your life story?
Before you commit, ask:
Am I open to living where the right business lives?
Can I realistically commit 5-10 years to this company, through recessions, personal life changes, and shifting interests?
Is this the right moment to absorb more stress and uncertainty, or would a later chapter be more aligned with my responsibilities and energy?
Answer these four questions with ruthless honesty, and youʼll do two things at once: protect yourself from the wrong deals, and give yourself deeper conviction when the right one finally appears.
Capital will always chase good businesses.
The edge in search is a founder who understands the full weight of ownership and still reaches for the keys.
Legacy Partners offices will be closed until January 5th. We would like to wish all newsletter subscribers a very Happy Christmas. May 2026 bring you prosperity, good health and every success to you and your family!
Insight of the Week
Womenʼs Search Networkʼs Women in Search Funds 2025 Study shows how quickly the female ETA pipeline is scaling. WSN has now tracked 133 women-led searches, 68 acquisitions, and 10 exits, with the 2025 survey focusing on 71 active searchers and CEOs across traditional, self-funded, accelerator, and long-term-hold models. Roughly two-thirds of these women run traditional, funded searches, raising capital from about 13 investors on average. Around one-third of acquired companies are in healthcare, and the rest are concentrated in software and B2B services.
For the Commute
How a boring Gate-Repair Company Became a $9M Outcome (Acquiring Minds Podcast)
Andy Rougeot bought RG Maintenance, a gate service and maintenance for self-storage facilities, and grew it from $2.5 million in revenue to $9 million in revenue in 5 years. He shares how he leaned on veteran-style servant leadership to win trust from blue-collar techs, used Public Storage as an anchor customer to expand into five states, and de-risked customer concentration by mapping multiple decision-makers across districts instead of relying on a single contact.
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