Sasha Orloff
@sashaorloff
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CEO @puzzlefin, host of @TurpentineMedia Finance podcast, and tech optimist. YC, ODF, VG alum. I tend to post about accounting, finance and fundraising.
San Francisco, CA
Joined June 2009
This graph 📈 = the result of a relentless team effort, customer obsession, and probably way too much caffeine!. Cheers to a year of wins, lessons, and relentless growth. 2024 showed us what’s possible—2025, @puzzlefin is coming for you. Thanks for being part of the journey!
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We raised $30M last November. Here’s an inside look at what I told investors at Puzzle’s first board meeting 👇
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Quickbooks, longtime partner of has decided to build it's own bill payment competitor. That's not a surprise with new leadership and new ambitions. BUT, they are also cutting off s API access? ouch.
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I like my sugar with coffee and cream (oh, and $30M!!!!!!). 🔥🔥🔥. I guess it's just an intergalactic kind of day.
It's out! @puzzlefin raises an additional $30M led by @S32_VC @xyz_vc @generalcatalyst to power a new era of AI-powered generative accounting. Unlike others, Puzzle rebuilt the core ledger from scratch to be smarter, faster & fit modern businesses. Read more:
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Slash raises $19M to be the bank for your side hustle. Founder said reason he is building Slash is “most importantly, I truly f*ck with our customers. They’re all like me and my co-founder: young, hungry, and out to get that bag. No shame in it.”. Huh?.
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Just a painful reminder via @a16z on why incentives matter and how AGI might really impact some really large markets:. [Generative AI and accounting has an] incentive MIS-alignment. Similarly to Legal AI, Accounting AI threatens to cannibalize billable hours with greater
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Founders in SF: let’s grab a coffee. Founders in NY: let’s grab a drink. Founders in Boulder: let’s go for a hike.
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@petercalloway Looking forward to prosecuting crime again, like the majority of our city, state and country (and world). We want it out of the veins and lungs of our communities, and the cost and risk of plaguing our city any longer needs to go up.
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We just processed transaction number $30,000,000,000. This is a HUGE deal. Why?. We have $30B worth of startup financial data training our AI categorization models and work flows. · The more data we have = The more time we save founders. A larger number of transactions are
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For any founders debating whether they should fundraise:. 1. Open up a Google Sheet.2. Write down the numbers you’d need to break even. Can you get enough customers and charge enough money to make it work?. If you can do that without funding. Why give away your company to.
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Let's go!!!!!!.
It’s out, we raised $15m to equip founders with smart accounting software. Great article by TechCrunch featuring our CEO, @sashaorloff:
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When I started my first company back in 2012, I realized something big: Accountants are the heartbeat of every business—they’re the ones keeping everything honest behind the scenes. But, I also noticed they’re often stuck with outdated, manual tools, doing work that could and
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I was in one of the most incredible founder groups of all time. And there was one universal problem we all ran into at 50 employees, and by 75 employees it was too late. We all naively underinvested in it, until we didn't realize it was too late. The topic: compensation.
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Founders, any software promising to do 100% of your accounting using AI without human oversight is a 🚩🚩. AI will never fully replace accountants, but it can enhance them. Accuracy is first and foremost. AI processes data at lightning speed, but human oversight ensures accuracy.
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Decided to take a detour on my morning bike ride the office - The Bay, Golden Gate Bridge, Alcatraz, sunny skies in March. Be careful. You might just fall in love with SF again.
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I have seen @immad from @mercury speak quite a few times. But I keep going because I always learn something that makes me a better founder. Yesterday at @TechCrunch Disrupt he did a talk called “How I CEO”. Two things stood out…
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What people think CEOs do: build. What CEOs actually do: . - Manage the board and investors.- Lead the company vision.- Manage the capital to achieve that vision.- Deal with people's problems.
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@pritika_mehta My first meeting of my first billionaire they were dressed in a full track suit and these soccer flip flops. Second billionaire was them pulling up in a Toyota Camry. Third didn’t know how to take a group selfie with an iPhone. SF is wild.
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Puzzle is the perfect complement to @mercury , the only bank with a truly modern API. This means safer, faster, more accurate financials + real-time insights, built natively for all Mercury users. (and a lot more coming soon!).
It's a big day for @sashaorloff and the @puzzlefin team. Congrats on the $15M raise! 🚀.
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@kvogt Nothing gets me more excited about the innovative future of GM than this quote…. “GM is committed to delivering the best driving experiences to our customers in a disciplined and capital efficient manner,” said Mary Barra, chair and CEO of GM.
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📣Big news! @puzzlefin is the 1st company to achieve Level 3 Autonomous Accounting! Today, we're unveiling the first-ever framework for #AI and #accounting. 🚗Inspired by self-driving cars (shoutout to @Cruise in SF!), we've developed your go-to guide to Autonomous Accounting ⤵️
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Tried this today. So far 1/1.
If you watch this episode, I guarantee you'll get significantly better at selling your product
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It’s days like today that I just love S.F. there is no better baseball stadium for weather, views, food and the taste of an ice cold, $19 Stella.
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A startup hiring hill I'll die on:. "Equity compensation is NOTHING without context.". I talk to so many founders about how to offer equity. The typical playbook is:. 1. come up with the equity number.2. use an abstract valuation to explain it - “when we’re worth $1bn, your.
How to convince top engineers to choose your startup over big tech:. It’s all about how you present the offer. Watch this video. Get the Google Slides for free in the comments 👇
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Two founders I know just announced whopping rounds today. So pumped for them & their teams!. Well, it's hard to master a new skill, especially one most people need, and it’s not a skill that is used often, like VC fundraising. That's why @mercury Series A raise is just so dope!
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Monday, I shared a rough pitch deck we used to raise our last couple rounds @puzzlefin. There is 1 part that investors actually care about and most founders mess up - which is your opener. Instead of boring you with a wordy tweet, I recorded a quick loom to explain what I
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“No founder should have to feel like an imposter, at least when it comes to finances.”. My founder journey from #MBA to @ycombinator to @beondeck to @villageglobal and why we are working hard at @puzzlefin to make understanding financial health as easy as clicking. Thanks to
Accounting software hasn't changed for 38 years, it's time for something new. For episode 13 of S³ we feature @puzzlefin a legitimately exciting accounting software that's lightning fast and packed with groundbreaking features.
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My first keynote after years of silence. New company. New funding. New beard. @EmpireStartups and the Empire State of Mind. #fintechweek2023.
What lessons are learned in incubating a huge idea inside a VC firm? . Don't miss @sashaorloff (@puzzlefin) as our final keynote speaker, in a fireside chat moderated by Sophia Xiao of @generalcatalyst. 👉 #EmpireFinTech during #NYFinTechWeek
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This will be a team to watch in founder and startup taxes. Ex-Ramp + ex-IRS ?!? 🔥🔥. If you are interested, phone number and website below.
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This cannot be real! 🤯. Within minutes of posting a Product Design position for Puzzle, my inbox is literally flooded with applicants. This can't be real, can it?
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Accuracy is everything in accounting, and @tryramp just raised the bar with their new App Center! 🚀. Ramp 🤝 Puzzle gives you:. 1. Faster book closing with direct integration into @puzzlefin.2. Less manual work, more focus on strategy.3. Handle more clients with better accuracy.
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Today is the day. 🎉 Founders, get ready to be mind-blown!. 📽️ See why second-time founders especially get it. 🤖 Learn what is Autonomous Accounting, and why you can finally get excited about accounting software. Yes, accounting software. #AutonomousAccounting @puzzlefin
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My choice of VC value-add tweet of the week, brought to you by the one and only @seema_amble of @a16z. Pricing. It's stressful. Confusing. Scary. Need a framework? Here we go. (at least for B2B, venture backed startups).
1/ Pricing can be confusing for early stage founders, especially in B2B fintech with many business models. From helping a number of our companies think through this over the years, new post from me + @mandrusko1 on how to navigate the pricing journey and potential options at.
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We spent 3 years building the most powerful and automated accounting solution for founders. And it’s getting really good. But don’t take my word for it….
@puzzlefin is the best accounting tool: based on GPT4. The first ever accounting software that has a simple "chat with accountant" button. No onboarding calls and extra payments. But most questions you get answered from their AI bot. The only report I need comes to my email
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“China has close to 800M internet users, and we have transitioned to mobile and leapfrogged almost every other country. People are buying everything on their phones. We are very excited about that” Joe Tsai, cofounder if Alibaba #MIGLobal (fintech sigh)
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We are HUGE fans of @brexHQ who built one of the most powerful APIs in fintech across banking, cards and financial planning. @puzzlefin is built native to their API, which means automated, highly accurate financials, auto-reconciled and available IN REAL-TIME (seriously).
Huge congrats to @puzzlefin and special merit to @sashaorloff for being a visionary and staying true to his journey. Rocket emojis up for what’s next from this group! 🚀.
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A16Z + Stripe + Ramp + Puzzle together on stage at NY Tech Week. Something just feels very, very right about this…. Sign up below to join us.
Excited to host Robert Clarkson (CRO Americas of Stripe), Colin Kennedy (CBO of Ramp) and @sashaorloff (CEO of Puzzle Financials) on a panel to discuss everything from PLG to enterprise GTM. Hosted by @stripe during #NYTechWeek
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It's not your finance team, it's their software! @seema_amble uncovered that CFOs were stuck with: . 1. Antiquated software.2. Hours wasted on manual processes that could be automated.3. 30-90 day finance data lag stopping them from making strategic decisions.
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“Why now?” is the hardest question you have to answer as a founder. 10 years ago when I was starting my 1st and 2nd companies, I had the idea for Puzzle but the technology was never there. Even after raising hundreds in venture capital, I still couldn’t get the answers I needed.
Puzzle leverages AI and machine learning to automate accounting for startups
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WOOT!.Sunday was our largest new customer acquisition to date. Gives a new meaning to #SundayFunday!. Huge 🙏 to @jasonjoyride for the amazing S3 - Saturday Startup Stories. Check out @puzzlefin and more here:.
Accounting software hasn't changed for 38 years, it's time for something new. For episode 13 of S³ we feature @puzzlefin a legitimately exciting accounting software that's lightning fast and packed with groundbreaking features.
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7yo daughter:.Daddy are you famous?!?! Why is your name on Spotify? That’s like Taylor Swift!. New podcast launch exceeded download expectations with a banger episode with @CaseySWoo! But also thanks to the @TurpentineMedia team for making this dad a rock star today!
New podcast for founders and finance teams called @TurpentineMedia Finance. What is different?.We focus on 1-2 key moments when a founder or CFO had to navigate a huge make-or-break decision to architect success.
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Can we try removing regulation instead of adding more regulation to deal with our current regulation? $200,00 to the bureaucracy of SF to open a small business? I started my software company with $300 in Delaware, online in about 2 days. It’s not the exact same, but still.
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@UESF Focus on educating our kids in SF with STEM and leave global politics to the federal government. This is a disgrace and a waste of time.
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What @pitdesi and @iamjakestream have built at @TheMint_vc is simply amazing. It’s the same ambition as YC, but with a focus on Fintech with some really mission driven founders. Almost makes me want to be an investor. Almost.
We just finished the 3rd cohort of @TheMint_vc, where we've been working closely, in-office w/ founders for the last few months. At Demo Day, 6 companies pitched to >200 investors; for those who missed it, here they are 👇🏾
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This is why you it’s just so great to live in #SF and @ycombinator!. Thanks to @CryptpalSingh and @MayraCeja007 for a killer unofficial YC alumni happy hour, and thanks to @jpmorgan and @wilsonsonsini for supporting the startup community. The boom loop has found PMF!
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I get so pumped when I see people like @hoomanradfar get to take their company Collective to the next level with a fresh round of $$ from amazing investors like @pitdesi, @QEDInvestors, @gradientpub and of course @thegp. Congrats team!
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So how did we raise $30M the at @puzzlefin?. Here are 4 key insights, plus a 🧵. 1. Focus on an ideal customer with a meaningful pain.2. Make a product they love.3. Create a flywheel with partners.4. Adopt the right tech (like AI) that can drive outsized impact.
I like my sugar with coffee and cream (oh, and $30M!!!!!!). 🔥🔥🔥. I guess it's just an intergalactic kind of day.
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New podcast for founders and finance teams called @TurpentineMedia Finance. What is different?.We focus on 1-2 key moments when a founder or CFO had to navigate a huge make-or-break decision to architect success.
𝗢𝘂𝗿 𝗻𝗲𝘄𝗲𝘀𝘁 𝘀𝗵𝗼𝘄, “𝗧𝘂𝗿𝗽𝗲𝗻𝘁𝗶𝗻𝗲 𝗙𝗶𝗻𝗮𝗻𝗰𝗲” 𝘄𝗶𝘁𝗵 @sashaorloff 𝗷𝘂𝘀𝘁 𝗹𝗮𝘂𝗻𝗰𝗵𝗲𝗱. 💸. Sasha is joined by top founders and finance leaders at high growth tech companies, including WeWork's former Global Head of Strategic Finance, @CaseySWoo. In
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How to convince top engineers to choose your startup over big tech:. It’s all about how you present the offer. Watch this video. Get the Google Slides for free in the comments 👇
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It arrived!!!.Scaling people - tactics for management and company building by the one and only @chughesjohnson, previous @stripe COO and @Google leader across basically everything - gmail, AdWords, apps, and self driving cars. Let the fun begin!
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Kicking off our @puzzlefin off-site with a few gems from @chughesjohnson's book Scaling People. 🤯🔥🚀. This book felt perfect for our offsite's theme — creating outsized customer value.
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I would expect nothing less from @blader. Every few years a founder ups the game on design. This is that founder. BTW if you like the website, you should also check out the @runwayco product, it's killer. Actually, even if you don't like the website you should still check out.
Who designed and built this site? . What a fucking delightful departure from cloning the Linear or Stripe website and calling it a day.
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@thetkkong The main challenge is ERPs don't fit into the traditional venture funding stages, as they take ~7 years to build, and it is a binary piece of software - it has to work 100% of the time, down to the penny, every edge case. Oracle, SAP, Netsuite, SAGE all took 7-10 years to.
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They built something people wanted! (iykyk). Congrats to @davj and thr @tryfondo team for a (too rare but) amazing accomplishment. We should celebrate this more instead of funding rounds.
𝗔𝗡𝗡𝗢𝗨𝗡𝗖𝗘𝗠𝗘𝗡𝗧: Last month @tryfondo crossed $6M ARR — and we're profitable!. 𝘛𝘩𝘪𝘴 𝘮𝘦𝘢𝘯𝘴 𝘍𝘰𝘯𝘥𝘰’𝘴 𝘣𝘶𝘴𝘪𝘯𝘦𝘴𝘴 𝘮𝘰𝘥𝘦𝘭 𝘪𝘴 𝘴𝘶𝘴𝘵𝘢𝘪𝘯𝘢𝘣𝘭𝘦 𝘢𝘯𝘥 𝘸𝘦 𝘤𝘢𝘯 𝘤𝘰𝘯𝘵𝘪𝘯𝘶𝘦 𝘵𝘰 𝘴𝘦𝘳𝘷𝘦 𝘩𝘪𝘨𝘩 𝘨𝘳𝘰𝘸𝘵𝘩 𝘴𝘵𝘢𝘳𝘵𝘶𝘱𝘴
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Startup valuations are more art than science. But here’s a framework that might help first-time founders:. 1. Pre-seed stage. Your startup has a working prototype and initial market validation. You’ll probably sign SAFEs (Simple Agreement for Future Equity), which is easy but.
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Check this out - we got featured by @MorningBrew in their most recent Our Future video. (You can see why I don't like wearing suits 😂)
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When you walk into a founder happy hour and someone asks you “What does Stio do?” . And I respond “They make jackets”. Iykyk. Thanks @StioMountain for making the best ski jackets, and most amusing startup founder party trick.
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Hottest ticket right now! An entire airport hanger jam packed with people at #StripeSessions. @sama is the Taylor Swift of the tech world. There is nobody more popular. (And for a good reason - what else has had a bigger, faster impact than @OpenAI ?!!?)
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Building a startup is hard. It takes a @villageglobal to build for scale, even with @puzzlefin’s startup accounting software (shameless plug!) Thankful to be part of the best village with @eriktorenberg @adwane @bencasnocha @PrateekAlsi @sheilagoodman @lucasbagnocv @frumpy
@villageglobal helping build smart accounting software for founders, #startup #fintech #accounting #software
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What I didn’t share before was how thankful I am that @beondeck exists when starting a company. Life is lonely as a founder. It’s less lonely with a community. It’s even less lonely with a community led by the amazing @julianweisser and @FedericoNoemie Ans @andreatorresmx.
Thrilled for @puzzlefin to be featured on @beondeck’s Top Companies of 2024!. Check it out 👇.
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Show me a quicker finance software onboarding 🤯 . Watch a founder set up his accounting in 12 clicks.
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Hot take: . Sharing bad customer quotes with investors is good. So many first time founders just share the good stuff with investors. Investors know things are going wrong. Investors assume things are wrong. Because no startup is perfect. So if you say everything is going
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Central (YC S24) just launched on product hunt! Check out the video. Hard to unsee how rad this is for early stage founders.
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It feels like @brexHQ is one of the first fintechs to incorporate AI into their user facing app. The office of the CFO has been lacking great software for decades. Now software is adding intelligence. Two generational shifts in one decade - it is getting exciting in #fintech!.
🚨 Huge Empower News! . We are working with @OpenAI to bring advanced AI-powered tools for CFOs and their teams. The new features will provide relevant insights on corporate spend and answer critical business questions all in real-time. Learn more:
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For founders (or soon-to-be founders), taking that first step is hard. @beondeck makes it easier, and surrounds you with a global network of other founders. Click below to apply for the next cohort. #ondeckpride.
Applications are now open for the 11th cohort of the On Deck Founders Fellowship!. After 10 successful cohorts, ODF is now transitioning to a yearly membership model to support builders throughout their journey as startup founders. Learn more and apply👇.
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YC Demo Day is happening this week 🎉. Founders will largely get a pass on due diligence during Demo Day. But why show up unprepared?. The number one reason why investors pass on a founder they want to fund is not having a base level of understanding of the financial health of.
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Here's how to close deals faster - organize your data room before investors ask for it. The difference between quick closes and failed deals comes down to preparation:. • Build your data room methodically from the start. • Share only what’s requested, but always be prepared.
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I am SO excited about this!. @mercury just raised the bar, again! Bank reconciliations have always been done manually, and now can be done with software. The result? 50% time savings closing the books. I challenge any #accountant to do it books faster. Just. Not. Possible.
Mercury 🤝 @puzzlefin .Giving you back valuable time. Learn more about how @TriviumCorp used our Transactions and Bank Statements APIs along with Puzzle’s modern General Ledger on one of their high-profile startup clients 👇.
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@tomerlondon @anothercohen A new alternative is long overdue. This week @puzzlefin will launch what we have been diligently working on for years. It’s time to bring accounting software from the 80s to the 20s.
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Fundraising is harder than everybody thinks, even if you’ve raised billions before. Here's fundraising advice I wish I had when I started 🧵.
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Founders chasing acquisition - here’s how you can pitch to @elon and other tech titans on X. @ChrisJBakke shares his strategy for engineering acquisition success, and how his negotiations with Musk started. It's all about great ideas, communicating them with precision, and
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@puzzlefin @S32_VC @xyz_vc @generalcatalyst @GaingelsVC @Soma_Capital @FogVentures @felicis @KaporCapital @sterlingroadvc @alumniventures @BornCap Thanks to our investors, new and old, for their support. It's time to help startups build better businesses. LFG!.
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It was really fun to finally get to share a sneak peak of what Puzzle is really building at the @EmpireStartups conference in NYC last week with Sophia Xiao of @generalcatalyst. Some take-aways here:
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@sf_safetynews For some reason in SF we protect criminals instead of victims. But even this is nuts. Caught 7x threatening to murder someone at gun point before we determined he was a public safety threat? SMH.
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Would have been interesting to be a fly on the wall on that discussion. Usually it is build vs buy. This seems like build vs buy vs kill?. Source here:
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Fresh $250M of capital for pre-seed and seed founders. Congrats to the @villageglobal team. We are a proud portfolio company and it's a special network and amazing founders. The @vuoriclothing SWAG totally did not influence my opinion at all. 😆.
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*LOVE* that @SusaVentures organized a volunteer event for their #holidayparty. Gift bags for low income and homeless mothers, bringing a small amount of joy this holiday season, 83% of which won’t receive anything this holidays. #yimby
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The comments are the best. Investors are like “I disagree!” and founders are all “Agree 100%!”. @jefielding with another spicy take, but the reason why every founder wants to work with you.
Founder friends 📣 Emailing a VC your financials is the fastest way to get an investor to say NO. Instead, consider setting up a 20 Zoom to walk the investor thru your model (screen share) and talk thru your thinking and assumptions. This builds trust and rapport. *if you don’t.
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Pleased to welcome CapitalOne co-founder Nigel Morris and @fintechjunkie Frank Rotman to LendUps Board. You know, typical week at LendUp. 👍(Via @julieverhage and @jennysurane).
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RIGHT NOW @puzzlefin is the #1 trending in fintech and #5 top company. For accounting software! yes, accounting! .
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Founders, want to practice your pitch with a VC before the big meeting? Perhaps before @ycombinator demo day?. @BainCapVC launched an AI pitch, and it is surprisingly good. I pitched a few ideas and got to term sheet. Can you?. source: @ChristinaPhili5.
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As a founder, you must constantly craft custom messages for the right audience. All of the messages are true. They just serve a different purpose. E.g. what resonates with founders about @puzzlefin is having control over their business instead of being a passenger - they’re.
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We added a tag to show all you if your startup's cash has FDIC coverage or not. Have confidence in all your cash, everywhere, all at once. From idea to concept in 24 hours. So proud of the @puzzlefin team!.
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Demo Day has come to a close. Here’s some advice to the founders who just got through it:. Demo Day feels like you've just been picked in the NFL Draft. You're not just a star in college football anymore; you're stepping into the major leagues, and everybody's chasing you,.
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Mercury Series A program is legit. So many mistakes could have been avoided, so many lessons learned, and so many impressive founders tackling huge problems. It’s an exciting time to be a founder, despite the doomsday news cycle. Well done @micaiahbj and the @mercury team!.
Great (slightly nerve-wracking day) of marathon moderating with @sashaorloff @blader and @ilyasu @mercebent @milesgrimshaw and @darian314 for @mercury
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"With 33 new fintech fundraises announced this week, it's starting to feel alive again.". Its about time! Thanks @NikMilanovic for writing This Week in Fintech - keeps me hungry and motivated!.
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Founders. you asked, and we delivered!. We finally launched your #1 request - instant revenue recognition (which works autonomously well for Stripe customers). We are calling it Effortless Revenue Recognition. One click, and you get. 👇.
In just 7 months since launch, @puzzlefin has built an effortless revenue recognition and insights tool for startups using @stripe 😮. The hype is real. Check it out: Connect Stripe with a simple OAuth and Puzzle auto-generates your cash revenue and.
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Tell me your wife is out of town without teeeelllliiingggg me….
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@mashadrokova @DayOneVC Congrats, and not surprising. You are building something special. proud to be a portfolio company!.
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I secretly love it when founders start with Quickbooks because they assume after decades it must be great. Then they feel the pain - it's actually quite slow, inaccurate (autobalancing what?!?) and unhelpful. They become @puzzlefin's strongest advocates to other founders!
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The inaugural episode of the Turpentine Finance podcast has launched!. I’m the host, joined in this first episode by WeWork’s former strategic SFO – @CaseySWoo. Together we talk about decision-making during hyper growth. This season will include hour-long deep dives with top.
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