People First, And Then Profits Follow with Dean Mathews

2 Oct 2025 · 42 min
41:43

A Scaling Up Business podcast interview where Bill Gallagher talks with Dean Matthews, founder of OnTheClock. Dean recounts the kitchen-table founding in 2004 after spotting demand on small-business forums, bootstrapping the company to roughly $5M ARR with ~22 employees and serving ~16,000 companies (~150k–200k users/month). Key themes: people-first leadership and delegation (building a loyal 22-person team, low turnover), product-market fit via early customer feedback, technical debt and a V2 re-engineering to support scale, payroll integrations (ADP, QuickBooks, Gusto) and a newly added built-in payroll, a planned scheduling overhaul and HR-lite feature expansions, and a growth goal of reaching 1 million monthly active users while adding a sales motion to move up-market.

Questions this video answers

2004 (kitchen-table start; product live ~3–4 months after late-2003 research).

About $5 million (bootstrapped company).

About 22 (Dean said '22 of us' and anticipating 23–24 in the next month or so).

About 16,000 companies.

Dean said roughly 150k–200k users; at one point he stated 'closer to 200,000 people a month.'

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