[SaaS & AI Series] Reinventing Bookkeeping for the Modern Era With Sasha Orloff

Sasha Orloff is the CEO and Co-founder of Puzzle, an AI-powered accounting platform helping startups, small businesses, and accounting firms gain real-time financial insights through a smart general ledger. Before Puzzle, he was a serial entrepreneur, serving as Co-founder and CEO of LendUp and Co-founder & Advisor to Mission Lane, with previous ventures collectively raising over $1 billion. Sasha also hosts the “Tech Finance” with Sasha Orloff podcast, where he interviews leaders shaping the future of finance and accounting.

Here’s a glimpse of what you’ll learn:

• [1:44] Sasha Orloff explains how modern platforms make building startups easier
• [5:49] Why strong accounting practices are critical for raising capital and scaling a business
• [8:34] How Puzzle uses AI to improve financial accuracy rather than just increase speed
• [13:45] Rebuilding accounting infrastructure for the AI era
• [16:44] The advantages of AI agents over traditional accounting automation
• [19:01] Puzzle’s evolution from serving startups to becoming a platform for accounting firms
• [20:32] Why great go-to-market execution often beats having the best product in SaaS
• [35:20] Creating customer “wow” moments through AI-powered error detection

In this episode…

For many businesses, accounting remains a slow, backward-looking process that delivers insights long after decisions have already been made. As AI reshapes industries across the economy, could financial operations become real-time, accurate, and proactive rather than reactive? What would it take to modernize one of the most critical yet overlooked functions in business?

Sasha Orloff, a serial entrepreneur and technology innovator, says the key is to rebuild accounting systems from the ground up, with data integrity and AI at the core. He notes that traditional software lacks real-time intelligence, leading to inefficiencies and delays. By reengineering the general ledger, businesses can access faster, more reliable financial insights and automate complex workflows. AI-powered anomaly detection and reconciliation further improve accuracy while reducing manual effort. The outcome is a more scalable and intelligent financial system for companies of all sizes.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz talks with Sasha Orloff, CEO and Co-founder of Puzzle, about transforming accounting with AI. They cover rebuilding systems for the AI era, using AI for accuracy over speed, why strong accounting drives growth, and strategies for adoption, customer trust, and go-to-market in a conservative industry.

Resources mentioned in this episode:

• Sasha Orloff on LinkedIn
• Puzzle
• Y Combinator
• Stripe
• Ramp
• Brex
• Mercury
• Gusto
• Rippling
• Silicon Valley Bank
• Notion
• QuickBooks
• OpenAI
• Slack
• Google Docs
• Google Sheets
• Salesforce
• Zoom
• Shopify
• Twilio
• Uber 
• Accountalent
• General Catalyst
• FOG Ventures
• “Tech Finance” with Sasha Orloff
• “E68: Jeff Grimes of Perplexity on the New AI-Native Analyst” on “Tech Finance” with Sasha Orloff
• “Making Decisions in Hyper Growth with Former WeWork Strategic CFO Casey Woo” on “Tech Finance” with Sasha Orloff
• “The Dealmaker’s Secrets: Steve McLaughlin on Crafting a Fundraising Story Worth $33B, CEO of FT Partners” on “Tech Finance” with Sasha Orloff

Related episodes:

• “[AI & SaaS Series] Building the Future of Voice AI With Kwin Kramer” on Inspired Insider Podcast
• “Automation Solutions with Wade Foster Founder of Zapier” on Inspired Insider Podcast
• “Why its Smart to Lead with Transparency with Nathan Resnick Founder of Sourcify” on Inspired Insider Podcast
• “Pipedrive: Brain Surgery, Married, & Moved Company from Estonia to U.S. All at Once – with Urmas Purde [Inspiration]” on Inspired Insider Podcast
• “[SaaS Series] Revolutionizing Online Forms and Productivity With Aytekin Tank of Jotform” on Inspired Insider Podcast

Quotable moments:

• “Accounting has one of the biggest impacts on how much money you actually take home from your business.”
• “Bad data leads to bad insights; good data leads to good insights.”
• “Accounting is binary — you either deliver complete books or you don’t keep the client.”
• “Sometimes the best product wins, but in most B2B software, the best go-to-market wins.”
• “If you could build the workflow from scratch, this is how you’d do it — so you have to keep building and rebuilding.”

Action steps:

1. Embrace data accuracy and integrity in accounting systems: Prioritizing clean, reliable financial data improves decision-making, builds stakeholder trust, and reduces costly errors.
2. Leverage AI-powered automation for repetitive accounting tasks: Using tools like Puzzle helps eliminate manual, time-consuming workflows and frees teams to focus on higher-value strategic work.
3. Stay open to experimenting with new technologies: Testing new platforms even with initial skepticism can uncover more efficient ways to manage workflows and knowledge.
4. Build partnerships with innovative fintech and SaaS providers: Integrating with companies that offer strong APIs expands functionality and streamlines operations.
5. Foster transparency and customer-led feedback loops: Encourage honest feedback and real customer stories to build trust and credibility, especially for AI-driven tools.

Episode Transcript

Intro 00:15

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz 00:22  

Dr. Jeremy Weisz here. I am the Founder of InspiredInsider.com, where I talk with inspirational entrepreneurs and leaders. Today is no different.  I have Sasha Orloff of Puzzle. You can check them at Puzzle.io and Accurate Books At AI Speed. This is what their slogan is. And we’re going to go deep into that. And Sasha, I’m going to formally introduce you, but I always like to point out other episodes of the podcast people should check out, since this is part of the AI slash SaaS Series. I was thinking, I don’t know. I know you’ve been backed by a lot of really interesting companies and, you know, you know, you know, a lot of people on Y Combinator. 

So I was thinking of some of the cool Y Combinator-backed companies that I’ve had on. I had one of the co-founders of Zapier, Wade Foster, on. That was a good episode. Kwin Kramer, CEO of Daily all about AI Voice. I don’t know if you know Kwin, but that was one of the one people that I’m like, they’d hit it off and have a lot of geek out on. Nathan Resnick of Sourcify was another one, and some on the SaaS side that I’ve had on Pipedrive was a really interesting interview. Jotform he talked about how he grew to 25 million users and talked a lot about the freemium model, which was interesting. And, and many more, I don’t know. What are some of your favorite SaaS companies? Sasha, on your end?

Sasha Orloff: 01:44  

My favorite SaaS companies. Well, I mean, I think I’m particularly excited about a lot of the, the opportunities that we have when we’re building companies to choose from. So when I started my first company There really weren’t many choices. Everything was kind of an old school. You wanted to do payment processing. You used authorize.net. You want to use a bank, use Silicon Valley Bank, you want to use spend management used Amex. And when you start a company today, just the thoughts of being able to use Stripe and Ramp and Brex and Mercury and Gusto and Rippling and all of these like great new modern companies. I think, you know, you hear about them a lot in the press, and they get a lot of really good press for a reason. But I just, I like it’s hard to not love the tools that we use to build companies and how much easier it is to start a company in 2026 than it was in 2010.

Dr. Jeremy Weisz: 02:37  

And then I’ve heard you talk about Notion a lot, you big Notion user.

Sasha Orloff: 02:42  

I was a Notion skeptic in the early days. I was like, wow, it’s like Google. Well, Google Docs is free and, and it’s easy to share and have version control and history. And of course, you just hire a bunch of like young kids and they, they’re like, this is just way better. And I felt like in the early days with notion, the learning curve was pretty steep. And now I just, I can’t, I can’t foresee not using them for almost everything we do as a company. They’re, they’re the brain of our company. They’re the repository of almost all the knowledge and brainstorming and thoughts. It’s like, it’s just incredible.

Dr. Jeremy Weisz: 03:21  

The best customers or clients are ones that start off as skeptics and become the best case study. So that’s interesting and we’ll get into it. Before I introduce you, this episode is brought to you by Rise25. At Rise25, we help businesses connect to their dream relationships and partnerships. We do that in a few ways. One, we’re an easy button for a company to launch and run a podcast. I know you, Sasha. You have a podcast. We do the strategy, accountability and the full execution and production. Number two, we’re in an easy button for a company’s gifting. So we make gifting staying top of mind for clients, partners, prospects, even staff from a cultural perspective. And, you know, one of the things we will talk about on this interview is about building trust and authenticity. And so like over the past decade, I found no better way to profile the people I admire in the podcast and share with the world what they’re working on and sending them sweet treats in the mail. You know, caveat, Sasha, I don’t like sending like mugs or, you know, merch or things. I send food because I like getting food. So I like, you know, for our best clients and partners, we’ll send something every 3 to 4 months for like five years. So they actually look forward to the packages. 

Sasha Orloff: 04:34  

The best part about gifts in the mail is they just permanently stick around your waist and you get to remember them forever in the form of belly fat.

Dr. Jeremy Weisz: 04:41  

Some of them are healthy, so I’m all in the health. But I’m excited to introduce Sasha Orloff, CEO and Co-founder of Puzzle. Puzzle is a modern alternative to QuickBooks. His previous companies have gone on to raise over $1 billion, and he says this is the biggest, boldest bet yet. And Puzzle is really an AI accounting software loved by startups, small business accounting firms. What they’ve done is they’ve taken the best of QuickBooks, OpenAI, Stripe and rebuilt the general ledger from the ground up. And really, their mission is to make accounting and finance a competitive advantage for every company. Because, you know, if you’re a small company, you’re not like a large company. You can afford really big finance teams. And they set out to really turn your accounting into a real time financial intelligence so you can make decisions for your business. So Sasha, thanks for joining me.

Sasha Orloff: 05:37  

Yeah, thanks for having me here. Let’s dive in.

Dr. Jeremy Weisz: 05:39  

Yeah, I’m going to pull up Puzzle. And why don’t you just talk a little bit about what you do and we’ll dig in?

Sasha Orloff: 05:49  

Well I think when we. The part of the origin story that becomes the most interesting in why I take on sort of accounting is I’m just not that creative of a person. I like looking at new technology trends and looking at really important industries. And how do we rethink them to be much more customer friendly than before? And so when I thought about what was something that every company needs, it’s accounting, it’s required by law. What’s something that has one of the biggest impacts on your ability to raise capital from venture funds or from banks to ability to get acquired? Should you want to sell a stake or sell the company entirely. 

Accounting is one of the largest impacts in the amount of money you get to take home for your business that you work so hard to build. So I like that aspect. And then the second part is I never realized how important accounting was until, again, you go through the motions of building and selling a company or you end up having a big team. And so I liked the way that you put it. I saw the power of the ability to make informed, confident decisions when I had an 18 person finance and accounting team. But most businesses, especially in the early days, can’t afford that at all. In fact, accounting is one of your largest expenses. In the early days, it might be $400 to $1000 of monthly expenses. That’s pretty expensive when you’re just starting off.

And so we had this really incredible, incredible inflection point with AI that said, can we bring some of the power of what a big, very expensive, very professional accounting and finance team is to every, every company in, in the country. And if we could do that, could we give business owners and founders the ability to increase their chances of building an enduring company, which is what we all strive for. We want to build something that lasts. And accounting has just never been really relevant because it’s always a future problem, not a today problem. But if you could make it real time and you could make it insightful, and you could take all of that data and derive insights on a day to day basis, well, then you can have confidence in your most important decisions.

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