May 15, 2019 · 24m · top-founders
1390 With $3m+ in ARR and 300+ Customers, He's Making Digital Advertising Easier for Publishers
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The Top Entrepreneurs, host Nathan Latka interviews Sortable founder and CEO Chris Reid, exploring how he bought back his company from private equity, pivoted it into a profitable ad-tech SaaS platform with over $3 million in ARR and 300+ customers, and achieved exceptional net retention and capital efficiency.
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 43.8% of the talking time here. How this is scored →
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Reid repeatedly shuts down Latka's direct inquiry regarding average contract value, asserting 'we don't disclose that' and refusing to provide initial ranges.
Hardest push from Nathan ▶ 12:27 Latka refuses non-answer on customer contract sizesLatka refuses Reid's deflection by highlighting thousands of podcast data points and insisting that customer contract tiers are essential context for the audience.
Biggest teaching moment ▶ 7:25 Reid educates on ad tech pricing mechanicsReid clarifies the structural misunderstanding between SaaS fees and revenue shares in ad tech, explaining they are mathematically two sides of the same per-impression coin.
Nathan holds their own ▶ 16:56 Latka defends interview rigor against metric skepticismWhen Reid disparages top-line numbers as uninformative, Latka hits back with his philosophy on how detailed host cross-examination uncovers fraudulent founder metrics.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Promotion for How to Be a Capitalist Without Any Capital | 0 | 0 | 0 | 0 | Monologue segment featuring host book promotions, intro clips, and episode context with no direct host-guest interaction. | |
| Chris Reid on Founding and Pivoting Sortable | 4 | 5 | 4 | 5 | Reid immediately corrects Latka's premise that Sortable was previously an agency, explaining it was a consumer publishing business. Latka pushes back on why it took three years to buy the company back from private equity. | |
| Analyzing Pricing Models and Net Revenue Retention | 6 | 5 | 3 | 5 | Latka probes SaaS metrics like net revenue retention and compares ad tech revenue lumpiness to predictable SaaS revenue. Reid educates Latka on how CPM and rev-share models mathematically align when optimizing entire publisher businesses. | |
| Customer Contract Value, Capital Raised, and Office Locations | 5 | 2 | 6 | 7 | Reid repeatedly stonewalls disclosing ACV and pricing ranges, stating 'we don't disclose that'. Latka firmly pushes back citing listener feedback across 3,000 interviews until Reid concedes a broad range. | |
| Sales Strategy, Customer Onboarding, and Payback Efficiency | 4 | 3 | 1 | 2 | A collaborative and straightforward segment where Reid details sales touch points, onboarding cycle times, and an accounting-based CAC payback period under six months. | |
| Year-Over-Year Growth and Annual Recurring Revenue Debate | 7 | 4 | 5 | 6 | Reid dismisses high-level top-line growth metrics as misleading, while Latka defends his methodology for exposing exaggerated figures and calculates an ARR estimate of over three million dollars which Reid disputes as too low. | |
| Future Fundraising Strategy and Company Valuation Expectations | 5 | 3 | 5 | 6 | Reid claims he would raise ten million dollars at less than standard dilution, leading Latka to press him on whether that implies an ambitious hundred-million-dollar-plus valuation. | |
| Rapid-Fire Questions with Founder Chris Reid | 2 | 1 | 2 | 1 | Standard rapid-fire closing segment where Reid gives concise, slightly unconventional answers regarding books and tools. |