Before Rilla was doing AI speech analytics for field sales teams, Sebastian Jimenez (CAS '18) was a standup comedian with a voting app that died the moment the midterms ended. On July 10, he sat down with the 2026 Summer Launchpad cohort for an AMA, and the story he told wasn't a highlight reel; it was three years of zero revenue, 27 failed markets, and one very stubborn idea about what actually makes a startup work.
The lesson, in his words: the market matters more than the product.
Ballotbox, and the four-year customer
Jimenez's first company out of NYU was Ballotbox, built with fellow students during the SLP accelerator. The pitch: let people vote from an app. Two weeks in, they learned that was illegal in the U.S. So they pivoted to a marketplace for political canvassers — and it worked, for about a month. Their first paying customer, a political organizing group, got them a little bit of monthly revenue before telling them, essentially, "see you in four years" once the midterms ended.
That's when the lesson landed: it wasn't a product problem. Political organizing is a market that transacts once every four years and has no money. No amount of good engineering fixes that.
Twenty-seven verticals, three years, zero revenue
Jimenez carried the canvassing tool into field marketing — helping brands like Heineken track door-to-door conversations — and eventually realized something bigger: 85–95% of commerce happens offline, and almost none of those conversations were being captured or analyzed the way online data is. That insight became Rilla's north star: build the equivalent of search-engine-level insight for offline, face-to-face commerce.
Getting there took 27 different market verticals over roughly three years, with no revenue, before the team landed on home-remodeling and window sales — reps who already carried tablets, which solved a basic audio-capture problem that had stalled every prior attempt. That "virtual ride-along" use case, letting sales managers coach remotely instead of riding along in the car, is what took Rilla from no revenue to real, sustained growth. From there, Rilla expanded into HVAC, home electrical, and home building — the same core product, one new market at a time. The company has grown steadily since, now with a team of around 100, and has raised funding along the way from investors including Bessemer and Google.
What he told the cohort to actually do
A few pieces of advice came up repeatedly, in this order:
- Don't hire until you have real revenue. Jimenez's rule of thumb: the four Rilla co-founders didn't bring on a first hire until they'd crossed a meaningful revenue milestone. Early on, every dollar of time you spend building a team is time not spent figuring out if anyone wants what you're building.
- Founders sell first. Jimenez sold Rilla's early revenue himself. If you're the founder, that's the job before you hire a salesperson — get in front of customers and learn to communicate the problem, not just the product.
- Talk to people about their day, not your idea. The best market insight came from asking a customer open-ended questions about her actual workflow — not pitching her on a solution. Ideas that hold up tend to come from getting close to a problem, not from brainstorming in a room.
- Co-founder alignment on values matters more than shared skills. Different strengths, same values — that's what let the Rilla team push through years without revenue.
- Build the habit stack in order: sleep, then food, then exercise. Jimenez was direct that this isn't a nice-to-have — sleep deprivation measurably tanks decision quality, and he treats it as a non-negotiable, especially given how much he travels.
- Get comfortable being wrong publicly. Rilla has a running tradition they call "Fuck Up Fridays" — team members share failures out loud and get applauded for it, on the logic that fast, visible failure is what gets you to the right answer faster.
Why this matters for you
Jimenez's first idea didn't work. It turned out to be illegal, and it still took him three years and 27 markets to find the one that did. The product barely changed after year one. What changed was the market, over and over, until one of them stuck.
If you're building right now, take the cue: talk to your users the way Jimenez talked to that field marketing manager. Ask about their day, not your product. And hold off on that first hire until you've made your first sale.
Want the fuller Rilla origin story? Read our earlier profile on Sebastian Jimenez.
