Self-funded part-time search: Best concurrent W2 job?

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January 20, 2026

by a searcher from Dartmouth College - Tuck School of Business at Dartmouth in Chicago, IL, USA

I have a narrow buy box (~50-mile radius, specific industry segment, small EBITDA range, etc.), and there isn’t enough pipeline flow to justify a full-time search. I’m considering taking a full-time job while continuing to search on the side. What kind of job makes the most sense if my plan is to continue searching part-time and eventually buy and operate within five years? (1) “Fancy-title” roles at startups or large industry-leading companies (e.g., Chief of Staff, Strategy, Corporate Development, Program Manager, etc.) (2) Functional roles at large industry-leading companies (e.g., Sales, Marketing, Finance, Operations, etc.) (3) Leadership roles at small or medium-sized businesses (e.g., General Manager, Operations, Sales, Marketing, Finance, Corporate Development, etc.) My sense is that “fancy-title” roles don’t contribute much to long-term small business ownership or operating experience—beyond providing higher compensation that could later fund equity, outsourced search support, or transaction costs. They also tend to offer less flexibility and require longer hours. I’m still exploring the practical benefits of functional roles at large companies versus leadership roles in smaller businesses. The latter seems ideal if there’s strong industry overlap with a future acquisition, but perhaps less valuable if the eventual purchase is in a different industry. For operators: Does a functional leadership role in a medium-sized business actually equip you for ownership? I’ve often heard that “nothing can prepare you for ownership,” but is that really true for a role like sales leadership at a small or medium-sized business? For lenders, investors, or advisors: How do you think about the risk of funding someone coming from a large industry-leading company (in the same or a different industry) versus someone with functional leadership experience in an unrelated small business?
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Reply by a searcher
from Thunderbird School of Global Management in Westport, CT, USA
I agree with ^redacted‌ , the way to go is to find a role in the specific industry segment you are looking for. This will give you skills and network to operate later on.
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Reply by a lender
from Cornell University in Los Angeles, CA, USA
Hi Anon - you are thinking about it the right way. The best W2 job is the one that matches the business you want to buy. The more relevant it is, the easier it is to get funded and the easier it is to operate after closing. If your goal is to buy and run a business within 5 years, I would rank the options like this: Option 3 is usually best. A leadership role at a small or mid-sized business (GM, Ops, Sales lead) is the closest thing to ownership. You learn people management, daily execution, problem solving, and accountability for results. Option 2 is next best, but only if it directly matches your target business. Sales, operations, or finance roles can be very helpful if they translate cleanly into what you will be running. Option 1 is usually last. Strategy and fancy-title roles can pay well, but they often do not build real operator experience. They help more on analysis than execution. Yes, functional leadership at a mid-sized business does prepare you for ownership. It is not perfect, but it helps a lot. Owning a team, managing performance, and being responsible for outcomes is very transferable. How lenders and investors see it is simple. They like low-risk transitions. Same industry and hands-on leadership experience is strongest. Big company backgrounds can still work, but you need to show you can run operations, not just plan strategy. Simple rule: pick the job that makes a lender say, “This is a natural next step.” We have a lot experience financing various companies via the SBA. If you ever need help reviewing a deal, I am happy to help. We work with all the major SBA lenders. The bank pay us after your loan closes, so this is a 100% free service for you.You can email me directly at redacted or schedule a meeting with me: https://cal.com/francodeguzman/30min. Look forward to chatting!
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