In this month’s Founder Spotlight, we’re putting the spotlight on Sasha Orloff, CEO of Puzzle!
How did you come up with the idea for Puzzle? Has it changed along the way?
Puzzle was born out of a combination of 3 things…
1. As a founder, I wanted real-time financials and metrics!
It turns out after interviewing 100+ other founders, they also wanted it too. We were tired of waiting weeks to understand cash, burn, runway, and significant changes I needed to pay attention to.
2. There was no modern accounting software!
This was something every company needs, cause every company has to file taxes. I saw that startups were all using a modern stack like Stripe, Brex, Ramp, Mercury, Gusto, Rippling, and then a decades-old accounting software that didn’t take full advantage of all the innovation from a modern fintech stack.
3. I needed to really know my numbers, now more than ever before. It’s no longer acceptable to just build a great product, but as founders we have to build great businesses too. But there is no tool for founders to intuitively understand their numbers as we are talking to investors, our team or making important decisions.
How did you meet your cofounder(s)?
We were both solo founders building something similar, and felt we had complementary skillsets. We both happened to be located in San Francisco and it was just before the pandemic, so we took some walks around South Park, did the First Round Capital Cofounder Dating Playbook, and went out for lots of beers at 21st Amendment.
After a few weeks we started hacking together and felt it was a good fit.
Where did you find your first 5 customers?
We are building Puzzle for startup founders, but I don’t have any Twitter followers and we we needed to start alpha testing in the pandemic. So we did 3 things to help:
1. We raised some money specifically with pre-seed investors who had a portfolio they could help us recruit. Not surprising, Sterling Road was the most helpful here.
2. I begged some startup friends from my days at YC and shamelessly asked everyone I knew if they had any friends just starting companies.
3. I joined On Deck Founders, a supportive community of founders creating new startups.
What is the one piece of advice you ignored back then but wish you’d taken now?
If you are not shipping daily or weekly customer value in the early days, there is an underlying issue you need to resolve ASAP. Whether it be alignment, communication, process, confusion, fear… (note: I am not advocating creating a Build Trap, but a value shipping machine).
Learn more about Puzzle at Puzzle.io.
Thanks again to Sasha Orloff for sharing your story!
Sterling Road invests in idea stage and pre-seed B2B startups based in the US, Canada and UK.
