Oct 4, 2021 · 19m · top-founders
TakeTask is Clickup for Deskless Workers Grows 80% to $2m ARR
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this interview, TakeTask CEO Sebastian Sarzynski discusses building a task management platform tailored for deskless enterprise workforces, scaling to $2 million in annual revenue, and preparing for a Series A funding round.
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 25% of the talking time here. How this is scored →
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sebastian directly rejects Nathan's math, clarifying that the 8% ESOP pool is carved out of the founders' 70% share rather than added on top.
Hardest push from Nathan ▶ 11:06 Nathan rejects 'no valuation' claimWhen Sebastian suggests there was no valuation because they used convertible debt, Nathan immediately interrupts to demand the cap on the note.
Biggest teaching moment ▶ 3:13 Sebastian reframes deskless worker use casesSebastian corrects Nathan's oversimplified peanut-shelf stocking example by explaining complex enterprise tasks like AI-assisted competitor price scraping and timestamped food safety audits.
Nathan holds their own ▶ 11:38 Nathan models convertible note dilution mathNathan instantly converts the $170k note at a $5M valuation cap into a precise 3.5% equity dilution figure to show the founder the true cost of capital.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Positioning TakeTask as Productivity Software for Deskless Workers | 5 | 4 | 2 | 3 | Nathan frames the product against desktop tools like ClickUp and Basecamp and offers a hypothetical retail scenario. Sebastian gently redirects Nathan's peanut-stacking example to actual enterprise use cases like AI price auditing and compliance timestamps. | |
| Enterprise Pricing, Cloud Deployments, and Large-Scale Implementations | 5 | 4 | 1 | 3 | Nathan converts the pricing model into standard SaaS metrics and ACVs ($60k/year). Sebastian explains why TakeTask relies on dedicated Azure cloud instances and enterprise deployments rather than pure self-serve SaaS. | |
| Startup Inception, Crowdfunding Roots, and Historical Revenue Growth | 6 | 3 | 1 | 4 | Nathan dissects TakeTask's revenue mix, catching that nearly half of their 1.2M revenue is professional services and implementation rather than pure recurring subscriptions. Sebastian explains that clients effectively pay for bespoke feature development. | |
| Fundraising Background, Valuation Caps, and Series A Objectives | 7 | 2 | 2 | 6 | When Sebastian claims there was no valuation on their convertible note, Nathan immediately pushes back to demand the valuation cap. Nathan then calculates the implied dilution percentage on the spot. | |
| Cap Table Structure, Employee Stock Options, and U.S. Flipping Plans | 6 | 3 | 2 | 5 | Nathan interrogates the cap table, tracking ownership stakes between co-founders, ESOP, and early crowdfunding investors. Sebastian clarifies how the option pool fits inside the founder shares and outlines their future US flipping plans. | |
| The Famous Five Rapid-Fire Questions | 3 | 1 | 1 | 1 | Standard rapid-fire closing sequence covering books, sleep, and entrepreneurial advice with full alignment between host and guest. |