From First Cheque to Exit: What Separates Boston's Winners

If you are an investor choosing where to put the next cheque, what actually predicts a successful exit? I asked three questions: how often companies exit and how much they return, which sectors convert to exits, and whether the lead investor matters.

• 60 companies, 28 lead investors and 197 deals from 2010 to 2026.
• Three tables shaped like a PitchBook export: companies, investors and deals, loaded through Power Query.
• The dataset is fictional sample data, so it is safe to share publicly.

1. Built a star schema in Power BI. The Deals fact table relates to Companies on Company ID and to Investors on Lead Investor ID, both one to many.
2. Added company level outcome fields: Outcome (Exited, Failed, Still Private), Funding Raised, Exit Value, Years to Exit and Founding Cohort.
3. Wrote the DAX measures in the semantic model, including Exit Rate, Median Exit Multiple and Backed Exit Rate. See the DAX.
4. Reconciled every headline number in DAX query view against an independent Python calculation.

A modelling decision worth explaining. My first investor measure showed PE firms with a 75% hit rate. PE and corporate buyers appear as the "lead investor" on the acquisitions themselves, so they got credit for every exit just by buying the company. I changed the measure to count only funding rounds an investor led. PE firms turned out to have led rounds for just two companies, neither of which has exited.

1. About one in five companies exits, and the exits pay well. 13 of 60 companies (22%) were acquired, 5 (8%) failed and 42 are still private. Acquired companies sold for a median 4.5x the capital they raised, about 4.3 years after their first round.
2. Sector makes the biggest difference. 55% of cybersecurity companies have exited, compared with 30% in AI and machine learning and 22% in wealth and asset management tech. Data and analytics, lending and SaaS have no exits yet.
3. Younger companies simply have not had time. About a third of companies founded from 2010 to 2013 have exited, against roughly one in ten founded from 2018 onwards.
4. Lead investors vary a lot within the same market. Among the seven VCs that led rounds for at least 10 companies, exit rates range from 0% to 40%.

For an LP or a fund analyst, sector selection and manager selection both show up clearly in the outcomes. For a founder, a lead investor's track record is worth checking alongside the market itself. The cohort view is a reminder to compare companies of a similar age before drawing conclusions.

• Add a time to exit distribution by sector and a survival curve by founding cohort.
• Credit co-investors as well as the lead for a fairer investor scorecard.
• Add slicers for investor type and founding cohort.
• Test whether the investor differences are statistically meaningful, since several investors have fewer than 10 companies.