Apr 29, 2020 · 20m · top-founders
1740 $5m Raised and $600k ARR When Fiverr Acquired, Did Common Holders See Any Cash?
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this interview, Nathan Latka speaks with AND CO co-founder Leif Abraham about scaling a freelance management SaaS platform to $600k ARR through viral marketing and partnerships, navigating a $5 million venture-backed exit to Fiverr, and transitioning the product into a free ecosystem land-grab.
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 46.5% of the talking time here. How this is scored →
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Abraham resists disclosing financial terms while maintaining an exit must work for everyone, prompting a direct clash when Latka denies that premise.
Hardest push from Nathan ▶ 17:33 Latka rejects the assertion that exits must pay common stockLatka forcefully counters Abraham by explaining founders can sell without common shareholders getting anything if liquidation preference clears first.
Biggest teaching moment ▶ 4:07 Abraham explains the offline freelance market dynamicsAbraham reframes the conversation around market capture, explaining to Latka why Fiverr needed offline workflow software rather than short-term SaaS subscription revenue.
Nathan holds their own ▶ 16:44 Latka details liquidation preferences mathLatka demonstrates sharp financial modeling acumen, breaking down the 1X preference on $5M raised against a $600k ARR run rate.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Podcast Updates and Request for iTunes Reviews | 0 | 0 | 0 | 0 | Introductory monologue and housekeeping where the host addresses review feedback and previews the guest's metrics before the interview begins. | |
| Post-Acquisition Operations and Freelancer Workflow | 6 | 5 | 2 | 4 | Latka challenges Abraham on why they switched to a free model, implying it was due to struggling revenue. Abraham educates Latka on Fiverr's strategic rationale regarding offline-to-online marketplace acquisition. | |
| Founding AND CO and Capital Raised | 5 | 2 | 1 | 3 | Latka drills into fundraising history, cap table specifics, and remote team structure while Abraham provides factual operational details. | |
| HostGator Website Hosting Sponsorship | 2 | 1 | 1 | 2 | Segment starts with a sponsor ad read followed by a brief discussion about communicating M&A negotiations to employees. | |
| Growth Hacks, Content Stunts, and Scaling | 6 | 4 | 3 | 4 | Latka attempts to back into customer counts and conversion economics, mishearing 60,000 as 6,000 until Abraham corrects him. Latka then probes the freemium paywall structure. | |
| Scaling via Distribution Partnerships | 6 | 4 | 1 | 3 | Latka asserts that turning the tool free made sense given low MRR, while Abraham explains how distribution partnerships like Envato drove bulk customer acquisition. | |
| Liquidation Preferences and Deal Realities | 8 | 2 | 4 | 8 | Latka aggressively pushes on liquidation preference waterfalls and whether early employees with common stock were wiped out. When Abraham states an exit must work for everyone, Latka directly refutes him. | |
| The Famous Five Fast-Paced Questions | 3 | 1 | 1 | 2 | Standard rapid-fire closing questionnaire with minor audio hiccups regarding age and family. |