Career pivot into ETA / search — coming from BigLaw-style entertainment attorney background

February 24, 2026

by a searcher from University of Texas in Austin, TX, USA

Hi everyone — I’m looking for candid guidance from this community. I’m a 40-year-old entertainment attorney with ~15 years of experience. I’ve done well professionally, but I’m burned out on law and, more importantly, on having no control over my time. I want to move into a role where I’m building and owning something and where my effort is directly tied to outcomes. Background: JD/MBA from top programs 15 years as a transactional lawyer (negotiation, contracts, risk management, deal process, stakeholder management). Most of the experience is within the entertainment and live events industry, with some minor experience in M&A, VC and Corporate/ Securities work. I live in Austin now, but most of my legal experience has been in NYC and Los Angeles. No formal operating/GM experience (my MBA doesn’t have post-MBA operating work behind it) I’m seriously considering entrepreneurship through acquisition (traditional search, self-funded, or independent sponsor), but I’m trying to pressure-test whether this is realistic given my background and age — and how others have bridged the “operator” gap. Specific questions I’d love feedback on: For someone with my profile, which path tends to fit best: funded search vs self-funded vs independent sponsor (and why)? What are the biggest skill gaps ex-lawyers run into when becoming a CEO/operator, and how did you close them? Would you recommend targeting certain types of businesses where my skills transfer (contract-heavy, regulated, high customer concentration, etc.) — or should I deliberately avoid those? If you were me, what would you do in the next 90 days to validate fit and build momentum (courses, internships, diligence reps, operator shadowing, networking, etc.)? Any resources / posts / podcasts specifically helpful for career-switchers into ETA? Happy to share more (geography, deal size, industry preferences) if helpful. Appreciate any blunt advice.

Reply by an investor
from Texas A&M University in Houston, TX, USA

Feel free to pooh-pooh and disagree. 40+ years self employed, never a guaranteed salary with an annual review, always person of last resort, never a corporate backstop and the cavalry never came to save me. Out of self preservation and survival some self employed people develop business, financial, whatever survival skills that people in corporate may not develop. “effort is directly tied to outcomes” Outcomes may be directly but not necessarily tied to effort. If by “outcomes” one of the things you mean is income, more effort may correlate to more income but not necessarily. Fire away. Hope it helps.

Reply by a searcher
from The University of Texas at El Paso in Austin, TX, USA

Thanks @redacted‌. My 2 cents belw. Ben, this is a very viable pivot. Your negotiation, risk management, and deal process background are real assets in ETA. But the operator gap is real too, and you should treat it seriously. A few candid thoughts on your questions below: #1: At 40, I’d lean self funded or independent sponsor over a traditional funded search. You’ll likely value autonomy more than a 7–10 year fund structure with LP constraints. #2: The biggest gap for ex-lawyers isn’t intelligence, it’s operational cadence. Managing frontline teams, cash flow, sales pipelines, and messy day to day execution is very different from advising on deals. You close that gap by getting close to operators: shadow, consult, or join a small business in an ops capacity before buying. #3: Don’t over index on “contract heavy” businesses just because of your background. That can become a crutch. Look for simple, durable cash flow businesses with strong middle managers. Your edge will be discipline and structure, not complexity. #4: In the next 90 days, talk to 20 searchers who bought and are 2–3 years in. Also spend real time with at least 2 small business owners and start reviewing CIMs and underwriting deals weekly. Build a simple deal thesis (size, geography, industry, hold period). ETA is less about credentials and more about temperament. Make sure you actually want to operate, not just escape law. If you do, your background is more transferable than you think. Hope that helps!

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