Jun 3, 2016 · 18m · top-founders
You Won't Believe How He's Sold 350 Businesses in 6 Years, EP 254: Thomas Smale
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Host Nathan Latka interviews Thomas Smale, co-founder of FE International, to explore how his bootstrapped online brokerage scaled to close over 350 website and SaaS acquisitions while generating $1.5 million in annual advisory revenue. Smale shares expert insights on digital asset valuation multiples, deal structuring, and the operational discipline required to scale a high-performance advisory firm.
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 50.7% of the talking time here. How this is scored →
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Thomas pushes back against Nathan's repeated badgering, stating that broker compensation is private internal company data.
Hardest push from Nathan ▶ 13:47 Nathan presses on commission splits despite refusalsNathan refuses to accept Thomas's privacy deflection, demanding the exact percentage split and citing public VC fee structures as precedent.
Biggest teaching moment ▶ 6:14 Thomas explains sub-$1M ARR SaaS valuation dynamicsThomas educates Nathan on why sub-$1M ARR SaaS transactions trade on net profit rather than top-line revenue multiples due to lack of scale.
Nathan holds their own ▶ 5:38 Nathan challenges net profit valuation with SaaS metricsNathan demonstrates SaaS finance expertise by detailing monthly churn, ARPU, LTV, and typical 5-11x top-line ARR multiples.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Origins and Founding Story of FE International | 7 | 6 | 2 | 6 | Nathan challenges Thomas's practice of valuing SaaS businesses on net profit multiples, citing standard SaaS metrics such as churn under 3% and forward ARR multiples of 5-11x. Thomas clarifies that sub-$1M ARR micro-SaaS deals lack scale and trade on net profit rather than top-line revenue. | |
| Case Study of PlanScope Sale to Josiah | 5 | 4 | 2 | 4 | Nathan analyzes the PlanScope transaction by estimating customer count and valuation multiples from monthly revenue. Thomas politely corrects Nathan on the buyer and seller identities and explains normal churn ranges for small SaaS assets. | |
| FE International Operational Structure, Revenue, and Broker Compensation | 5 | 2 | 5 | 8 | Nathan repeatedly drills into FE International's internal broker compensation splits, comparing it to the standard venture capital 2-and-20 model. Thomas firmly refuses to share private internal salary and tiered commission numbers. | |
| Mid-Roll Sponsorship Promotion and Weekly Cash Contest Announcement | 2 | 1 | 1 | 1 | The segment consists of an ad read for HostGator, weekly cash contest rules, and a rapid-fire Famous Five questionnaire with light banter. |