Jun 7, 2016 · 20m · top-founders
From Cleaning Company at 26 to $14m Agency By His 42nd Birthday, EP 266: Andrew Howlett
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 Andrew Howlett, Chief Digital Officer at Rain, about scaling a boutique digital agency from its e-commerce roots into a $14 million powerhouse serving top enterprise brands. Howlett shares practical insights into agency retainer models, high-impact digital campaigns, and the operational advantages of integrated, full-stack technical execution.
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 41.6% of the talking time here. How this is scored →
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Andrew firmly clarifies that they never guarantee view counts in client contracts due to unpredictable client sign-off and editing decisions.
Hardest push from Nathan ▶ 8:15 Challenging agency automation claimsNathan directly challenges Andrew on whether their influencer marketing relies on software or just manual employee hustle.
Biggest teaching moment ▶ 6:54 Explaining digital-first Super Bowl strategyAndrew corrects Nathan's assumption of a 3 to 4 million dollar broadcast placement by breaking down their 500k digital-only influencer strategy.
Nathan holds their own ▶ 12:04 Validating agency cash flows over SaaS valuationsNathan demonstrates business acumen by contrasting real agency top-line revenues against overvalued SaaS startups lacking revenue.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Weekly Contest Winner and Episode Teasers | 4 | 2 | 1 | 2 | Nathan introduces the show and quickly digs into the exact financials and margin of Andrew's initial e-commerce cleaning business. Andrew cooperatively provides the backstory and revenue details. | |
| Rain Agency Scale, Retainers, and Enterprise Clients | 5 | 2 | 1 | 2 | Nathan probes into Rain Agency's retainer models, employee headcounts, and client concentration. Andrew transparently breaks down their enterprise retainer pricing of 50k to 75k per month. | |
| Campbell's Chunky Soup Super Bowl Digital Campaign | 5 | 4 | 2 | 3 | Nathan assumes a traditional multi-million dollar Super Bowl ad buy, but Andrew explains their digital-first influencer strategy for Campbell's Chunky Soup. Nathan pushes on whether the influencer seeding is automated by software or pure manual hustle. | |
| Facebook 10th Anniversary Campaign and Agency Margins | 5 | 3 | 2 | 3 | Nathan clarifies the pricing of the Facebook anniversary project, catching whether it was 150k total or per video. Andrew clarifies the total 450k scope and explains why video margins are lower than software development. | |
| Fourteen Million in Revenue and Full-Stack Advantage | 6 | 3 | 1 | 2 | Nathan contrasts agency cash flow with SaaS hype and asks about competing with holding companies like WPP. Andrew provides a detailed strategic breakdown of their full-stack competitive advantage. | |
| Connecting with Andrew Howlett Online | 3 | 1 | 0 | 1 | The interview wraps up with standard contact information, mid-roll sponsor reads, and the Famous Five quick-fire questions. |