Across 155 exited traditional ETA investments covering ~92% of known exits, observable demographic factors explain only ~26% of IRR variation, implying that execution quality, judgment, and idiosyncratic factors drive the majority of outcomes

Geography is the strongest quantitative predictor, with U.S. and Canada–based searches achieving IRRs roughly ~36 percentage points higher than non-North American searches after controlling for other variables

MBA-led teams show materially better performance, outperforming non-MBA teams by ~25 percentage points in IRR, while differences between elite MBA programs and other MBA programs are small and not statistically meaningful

Partnerships, prior banking/PE/consulting backgrounds, and military experience show higher median IRRs in isolation (roughly mid-20s to mid-30s), but most of these effects fade once geography and MBA status are controlled for

Industry selection contributes little to return dispersion, with software and non-software deals showing similar median IRRs (~26% vs ~25%), reinforcing that ETA outcomes are driven more by structure and operator execution than sector choice

Jeremy Yamaguchi contrasts bootstrapping and venture funding by observing that bootstrappers often pull lifestyle and real liquidity forward, while venture paths tend to require longer delayed gratification unless secondaries provide earlier cash-out

His career arc shows a repeatable pattern of pairing tech and performance marketing with fragmented home services, bootstrapping Golden Shine to an early exit, then using YC and venture capital to scale Lawn Love nationally before selling and moving into the next rollup

He frames opportunity selection as finding a comparative advantage stack where you’re not best-in-world at one skill but unusually strong at the intersection, combining product sense, software ability, growth marketing, fundraising, and comfort operating with blue-collar field teams

Cabana’s thesis is to build a first national pool services brand through M&A plus organic growth, using a long time-horizon to invest in people and vertical software that off-the-shelf tools can’t support for multi-location rollups and complex operations

His practical playbook emphasizes fast lead response and disciplined local acquisition channels, fundraising run like enterprise sales with tight timelines and investor-fit, and an acquisition filter that prioritizes seller integrity because company culture and hidden liabilities mirror the founder

Many first-time buyers say they want confidence before committing, but in practice confidence is created after taking responsibility and acting with real consequences

Search can create a false sense of readiness because decisions stay theoretical in models and spreadsheets, so hesitation often disguises itself as extra diligence and rerunning the numbers

Closing replaces certainty with consequence as payroll, customers, vendors, and employees make decisions irreversible, so confidence often drops right when responsibility spikes and that reaction is normal

A predictable dip follows in the first 30–45 days as new owners hit a “valley” where doubt rises despite stable performance, and that discomfort is usually the start of accelerated learning rather than proof of a bad deal

Competence tends to arrive before confidence as owners accumulate evidence through repeated hard decisions, so waiting to feel ready becomes a growth tax while those who move forward gain faster decision reps and build real judgment