Dec 10, 2018 · 20m · top-founders
1234 How He Bootstrapped to $160m in ARR in HR Space
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In this episode of The Top Entrepreneurs Podcast, host Nathan Latka interviews iCIMS founder and CEO Colin Day to examine how the talent acquisition software leader bootstrapped past $160 million in ARR while maintaining profitability and market leadership.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 37.3% of the talking time here. How this is scored →
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Colin pushes back on Nathan's direct probe for internal customer acquisition cost and net retention, maintaining confidentiality boundaries.
Hardest push from Nathan ▶ 15:31 Nathan correcting the premise from M&A costs to organic CACNathan interrupts Colin's pivot toward M&A purchase economics to clarify that he specifically wants internal customer acquisition spend.
Biggest teaching moment ▶ 10:27 Colin breaking down the three rationale drivers of an IPOColin educates Nathan with an industry insider framework detailing capital need, CEO vanity, and brand legitimacy as the sole drivers of taking a company public.
Nathan holds their own ▶ 12:47 Nathan projecting forward ARR run-rates in real timeNathan demonstrates sharp financial command by instantly applying 25% target growth to derive Colin's projected 2018 ARR target, drawing praise from the guest.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Introducing Colin Day and iCIMS Talent Acquisition Platform | 5 | 2 | 1 | 2 | Nathan drills into ARR numbers and asks how leadership stays motivated after cashing out secondary liquidity. Colin explains their competitive landscape against Taleo and Workday. | |
| Moving Upmarket and Scaling Deal Sizes | 6 | 2 | 1 | 2 | Nathan calculates monthly ARPU on the fly from ARR and customer count to evaluate unit economics. Colin details their shift upmarket to enterprise clients with a hybrid pricing structure. | |
| Capital Markets, TextRecruit Acquisition, and IPO Considerations | 6 | 3 | 1 | 3 | Nathan brings up specific PE buyout dynamics including Vista Equity's $14B fund and potential valuation multiples. Colin lays out his three-factor framework for assessing an IPO versus staying private. | |
| Revenue Targets and Google for Jobs Advertising Opportunity | 6 | 3 | 2 | 4 | Nathan presses on internal CAC and net revenue retention after calculating Colin's 2018 forward run rate. Colin politely declines exact proprietary metrics while sharing their target 24-month payback benchmark. | |
| The Famous Five Questions with Colin Day | 3 | 1 | 1 | 2 | Nathan moves through the Famous Five routine, tossing in a quick query about Microsoft's GitHub valuation. Colin offers lighthearted reflections on his habits, family life, and trusting his gut. |