Aug 7, 2017 · 18m · top-founders
744: Companies Pay Her $10-100k to Text Customers Funny Messages
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, host Nathan Latka interviews Bite Size founder Jess Lee to examine how her lean, profitable startup scaled from $200 to over $300,000 in revenue by delivering high-converting, TCPA-compliant conversational SMS marketing campaigns for major enterprise brands.
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 52.9% of the talking time here. How this is scored →
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
When Nathan intensely breaks down her unit margins, Jess pushes back saying, 'you're asking hard questions,' resisting Nathan's intrusive line of questioning.
Hardest push from Nathan ▶ 9:29 Nathan insists on getting the real monthly revenueNathan refuses to let Jess dodge revealing exact revenue figures, calling out her hesitation and demanding the real number.
Biggest teaching moment ▶ 3:32 Jess explains TCPA and manual texting legalityJess educates Nathan on TCPA compliance under FCC rules, detailing why manual human intervention keeps their mass text platform legal.
Nathan holds their own ▶ 12:04 Nathan explains political market dynamicsNathan demonstrates domain knowledge of political campaigns, explaining how single-party specialization can create strong market share advantages.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Rebranding to Bite Size and Conversational Texting Concept | 4 | 3 | 1 | 2 | Nathan asks foundational questions to understand Bite Size's conversational texting model. Jess explains how they use movie characters to drive ticketing via Fandango links. Nathan challenges the practicality by asking how customer phone databases are built without spamming. | |
| FCC Compliance and Manual Texting Workflow | 6 | 4 | 3 | 7 | Nathan intensely pushes Jess on the legality of unsolicited texting under FCC regulations, consumer annoyance, and unit economics. Jess explains manual texting compliance under the TCPA and breaks down her 25-cent pricing versus data and Twilio costs while Nathan presses hard for specific margins. | |
| Funding, Team Composition, and Market Niches | 6 | 2 | 2 | 6 | Nathan presses Jess for exact monthly revenue figures when she hesitates, estimating her monthly burn and profit based on team size. They also discuss political campaign dynamics where Nathan highlights how taking partisan sides affects customer acquisition. | |
| Growth Trajectory, Historical Revenue, and Future Strategy | 3 | 1 | 1 | 2 | Nathan walks through Bite Size's historical revenue progression from $250 in 2013 to $300k in 2016 before shifting into mid-roll sponsor reads for GetLatka and The Top Inbox. | |
| The Famous Five Questions with Jess Lee | 2 | 1 | 1 | 1 | Nathan conducts the standard rapid-fire Famous Five questionnaire. Jess shares insights on entrepreneurial mindset and overcomes challenges, followed by Nathan's outro summary. |