Sasha Orloff, Puzzle, Founder & CEO on Real-Time Accounting

**Sasha Orloff** (0:00)
Whatever you think is the most fun, let's do it.

**Grace Gong** (0:02)
Okay, we are on. Hi, Sasha, welcome to Venture with Grace.

**Sasha Orloff** (0:06)
Hi, we are live, live with Grace.

**Grace Gong** (0:10)
Yeah, of course, my Instagram is like having a public meltdown right now because for some reason I didn't connect, but I'll fix that later. So I wanna give a shout out to our amazing sponsor. This episode is brought to you by Nebius, the ultimate claw for AI innovators. Nebius provides AI infrastructure, you can come down, combining reliability and speed with flexibility and engineering support unmatched by hyperscalers. AI leaders like Meta, Shopify, and Higgsfield already partnered with Nebius to render AI workloads. Plus, Venture back start up can save up to 150k on compute costs when they apply for access. Visit nebius.com or nebius.com/start up to learn more.

**Sasha Orloff** (0:47)
Also, one of the best billboards in all of the 101, on the side of the freeway.

**Grace Gong** (0:52)
Yes. I tracked these, but I was like, actually, the Nebius one is like the most standout because of the screen. And that was like the thing. It's like AI runs better on Nebius. I love it.

**Sasha Orloff** (1:02)
Yeah, it's simple. It's great. Cool design. We need to push this individually. Yes.

**Grace Gong** (1:08)
Sasha, honestly, I've listened to your podcast before. Like, you know, you're the OTF, like the CFO, sweet people. And you talk to a lot of like amazing, like FinTech leaders.
I want to start with like, you know, your journey into the startup land. Obviously, you're an amazing podcast host yourself. Let's start with a puzzle. And then like, how do you kind of like stumble up on the problem? And we can talk about podcasts all day, but...

**Sasha Orloff** (1:34)
I think that's the most polite way of saying, you're kind of old. OG is like a much more polite way of saying, you're old. You've been doing this in the Valley since the 90s, when there was a.com level. Oh yeah, my first job on a college, not as a founder.

**Grace Gong** (1:50)
I wouldn't assume. I mean, you look very young, but you're still addressing Grace.

**Sasha Orloff** (1:54)
I know. I just gotta thank you for the filters. Whatever Grace's pre-filters are on this, this is great. No, my first job out of college in 99 was a block away in downtown San Francisco, right on first in market. We were the first online payment processor, the largest online payment processor, when the internet was just in its budding days of commerce.
I've been here off and on. Then we had the cloud boom and the mobile boom. Now, we're having the AI boom and it's fun. All right, that's a long-winded intro too. All right, Grace, let's actually answer your question. Let's make this podcast interesting for everybody.
What's I think interesting this time? My last company, we ended up splitting my last company into three separate companies. When I took the time off as a founder to think about, what was the thing that I wanted to do next? Did I want to work somewhere? Did I want to start another company? And I took a bunch of time off. In fact, actually, I was having dinner with somebody at first round, and they actually wrote a really interesting article about founders who have built something and are thinking about what are the next steps. It took me about six to ten months to kind of decompress and rethink. And one of the things that I like, because I'm not smart, like I can't invent something that doesn't exist. That's not my thing. I'm not like Apple or even like Perplexity or Instagram, Twitter, like people that think of a new idea. I'm more of a type of founder that takes current changes in technology that are going to make big shifts in the market and applies them to build a better product and hopefully a better go to market. So when I was thinking about ideas of what I wanted to do next, I came down to three ideas.
This one seemed building a modern accounting software as an alternative to QuickBooks. Every YC batch for 10 years, for 15 years, venture founders every year, this has been a theme, we're going to take on QuickBooks, we're going to build something bigger and better, and none of them ever succeeded. So it felt like one of those really big bets that there was a lot of reasons why something didn't exist.
There are, and we could talk about them, but I thought, all right, what's the big shift happening in technology now? It's AI, or it was going to be AI, we didn't know what an LLM or agent was going to be at that point, but something around artificial intelligence. We had a whole new set of really popular tools, Ramp, Stripe, Brex, Mercury, Gusto, Rippling, DL, et cetera, et cetera. And they all just kind of funneled into this 35-year-old piece of software called QuickBooks. And AI was going to have a big impact on, I think, the biggest unsolved part of accounting, which is the long tail. So the way they sort of think about it is, the first 80% of accounting is pretty easy to build. That's where most startups naively, over the past 15 years, have gone in and tried. The last 80% is the hard part. And so I thought AI was going to build a big shift, along with this API access and more data from all these great new fintech winners. And so I threw my hat in the ring and said, let's build a puzzle.