Apr 15, 2019 · 24m · top-founders
1360 How He's Shifting Doodle Meeting Tool 200m MAU's to SaaS
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In this episode of The Top Entrepreneurs, Nathan Latka interviews Doodle executive Gabriel Ottino to explore how the popular scheduling platform is converting its massive 200-million-user base from an advertising model into a fast-growing SaaS subscription business.
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 42.7% of the talking time here. How this is scored →
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Gabriel playfully rebuffs Nathan's direct challenge regarding running a company without equity by replying 'Good question. Next question.'
Hardest push from Nathan ▶ 19:48 Pushing on lack of equityNathan directly challenges Gabriel's career decision to lead Doodle without an equity stake, refusing to drop the line of questioning until upside incentives are explained.
Biggest teaching moment ▶ 10:05 Low conversion upsideGabriel reframes Doodle's seemingly dismal conversion rate of 25,000 paid subscribers out of 200M MAU as massive latent upside for SaaS expansion.
Nathan holds their own ▶ 16:16 Instant unit economics computationNathan instantly computes that paying $10 per trial at a 20% conversion rate creates a $50 CAC against a $30 annual customer value, showing sharp financial fluency.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Book Promotion: How to Be a Capitalist Without Any Capital | 0 | 0 | 0 | 0 | Monologue segment consisting of host book promotion and episode preview summary. | |
| Podcast Intro: The Top Entrepreneurs | 4 | 2 | 1 | 1 | Nathan introduces Gabriel and establishes Doodle's founding history and scale. The exchange is cordial and purely factual. | |
| Transitioning Doodle from Ads to SaaS Subscription Model | 5 | 4 | 1 | 2 | Gabriel explains the strategic imperative from parent company Tamedia to shift Doodle from an ad-driven model to SaaS productivity software. Nathan clarifies Gabriel's hiring circumstances and geographic distribution. | |
| Evaluating Current Revenue Mix: Advertising vs. SaaS | 6 | 4 | 1 | 3 | Nathan drills down into the advertising revenue percentage and annual pricing tiers. Gabriel breaks down how large enterprise accounts dilute the average annual revenue per customer down to $30 to $40. | |
| User Base Conversion and SaaS Growth Trajectory | 7 | 3 | 2 | 4 | Nathan rapidly calculates Doodle's monthly SaaS run rate based on customer count and price point, probing their aggressive target to reach $1.5M ARR. Gabriel acknowledges the conversion rate from 200M users is low but represents major upside. | |
| Customer Acquisition Economics and Marketing Experiments | 8 | 4 | 2 | 4 | Nathan conducts live unit economics math when Gabriel shares his trial acquisition cost targets and 15-20% trial-to-paid conversion rates. Nathan demonstrates strong domain expertise by pointing out CAC payback ratios. | |
| Corporate Funding Dynamics and Executive Alignment with Tamedia | 6 | 3 | 5 | 7 | Nathan pushes hard on corporate governance and executive compensation after learning Gabriel has no equity in the corporate subsidiary. Gabriel deflects playfully before Nathan restates the question to ask about performance incentives. | |
| The Famous Five Rapid-Fire Questions | 3 | 1 | 1 | 1 | Nathan runs through the standard rapid-fire questions to close out the interview on a friendly and reflective note. |