I’m thrilled to share that @numeral has raised a $35M Series B, led by Mayfield, at a $350M valuation! Turns out, sales tax and VAT have gotten so complex that we need AI and millions of dollars in VC funding to make it simple again. This brings us to $57M in funding, including our $18 million Series A led by Benchmark Capital in March of this year. We are 1,057 days into building Numeral, and I’m humbled to say that we’ve processed over $5 billion in transaction volume, filed 150,000 sales tax returns for +2,000 paying customers, and achieved 3.5x year-over-year revenue growth. Numeral is the end-to-end platform for sales tax and VAT compliance. I couldn't be prouder of what we’ve accomplished… but there's still a lot left to build, many new customers to serve, and a heck of a lot more sales tax filings to, well, file. So what’s next? Global coverage: Growing internationally? Our in-house platform currently covers 60+ countries, and we are expanding to many more by the end of the year. Integrations: As you may have noticed, we’ve launched several new integrations over the last few months, including with Orb, Sequence, Tabs, and others. Some exciting integrations to come! Automation: Could Numeral be the most boring AI company? Our AI may not be the flashiest, but our automations mean you'll never have to log into a government portal or listen to hold music again. Our team: We are currently hiring for multiple roles across our organization. Ready to join us? Matt and I are incredibly grateful to our customers and team. Thank you for making this milestone possible. And a special thank you to our wonderful investors: @MayfieldFund, @SPangulur, @benchmark, @chetanp, @ycombinator, @gustaf, @uncorkcap, @susanwliu, @FundersClub, @mittal, @mantisVC, @AlexPallNY, @ShaanVP, @lennysan, @moizali, @mrsharma, @ringmybeller, @khency6, @asturnerr, @maariabajwa, and so many others.

Our 1st customer paid us $75 per filing. Our 10th customer paid us $75 per filing. Our 11th customer paid us $75 per filing. Our 101st customer paid us $75 per filing. Our 1001st customer paid us $75 per filing. Our 1002nd customer paid us $150 per filing because they accidentally paid twice. We refunded them. Our 2001st customer paid us $75 per filing. This is why we keep our pricing simple. The sales tax world is unbelievably complex. If you use Numeral, all you have to know is two things. 1. I’m covered on everything sales tax-related. 2. I know exactly how much I’m paying per filing. Simple as.

Excited to share that Numeral has raised an $18M Series A led by Benchmark! We started @NumeralTax two years ago to solve the nightmare that is sales tax for growing ecommerce brands. Simply put – sales tax was the last thing I wanted to think about when scaling my brands. There is a ton of work left, but it is worth reflecting on how far we’ve come in the last 24 months: - Grown the team to 38 people 👥 - Raised over $22M+ in funding 💰 - Opened our new office in San Francisco 🌉 - Increased ARR by 3x+ in ‘24 📈 - Trusted by 1,000+ businesses, including many of my favorites like Ridge, Graza, and Immi 💞 And now, with this fundraising, we are announcing that we support SaaS businesses, too! As more and more jurisdictions look to tax software sales, Numeral is ready with all of the integrations you’d expect. Numeral is the platform for sales tax. From rates to registrations and everything in between – we put sales tax on autopilot for ecommerce and SaaS brands. Thank you to all of our customers who’ve trusted us thus far and to our amazing team (we’re hiring)! And a special thank you to the wonderful investors supporting our mission: @benchmark, @chetanp, @ycombinator, @gustaf, @uncorkcap, @susanwliu, @FundersClub, Alex Mittal, @ShaanVP, @lennysan, @moizali, @mrsharma, @ringmybeller, @khency6, Adam Turner, @maariabajwa, and so many others.

too low

Had a blast with @johncoogan and @jordihays on @tbpn! Can confirm the gong is even better in person!

My DTC brand was doing $10M/year in revenue. I left it behind to start Numeral. Here’s why:

I scaled a DTC brand to $10M in revenue. If I had to do it again, but faster, I’d use these 11 tools:

This happened 💍

YC was a game-changer for us. Frankly, we wouldn't be where we are today without @ycombinator. Today is the deadline to apply for the YC W25 batch… you should apply! 🧡 There are lots of accelerators out there. And there are lots of ways to raise a seed round. But the value that YC provides is so much more than capital. The Network: It is pretty magical. Everyone just wants to help, including leveraging their networks for you. The other day, I saw a Bookface post (on YC's forum) asking for an introduction to a very specific F100 CEO, and someone offered to facilitate it. The Pressure: In a good way. Being around other founders trying to build really big companies just keeps you motivated. Sharing war stories... pushing each other. Shout-out to our batchmates @jfudem, @ShariarK8, @JPSchneck, and @andywang. The Partners: We worked with @gustaf. I had worked with him at Airbnb, so I wasn’t sure how much more I had to learn, but I was totally wrong. YC partners have seen everything and developed this incredible, quick intuition. Gustaf has saved us from big mistakes on multiple occasions. The Capital: Yea, YC writes a very meaningful check into your company. But it also provides founders a springboard to raise their next round into demo day! You can now apply for YC’s W25 batch! Do it!

I sold over $25M of jewelry online. It was a terrible business. The truth is, big numbers like that look cool on the surface. When you dig deeper, you uncover a host of issues...

I had an itch to scratch with sales tax while running a couple of 7/8-fig brands on @Shopify. About 8 months later, we're building @NumeralTax, the #1 solution to eliminate the headache of filing sales tax across 45 states and 3k+ counties. Typically, brands on Numeral (numeralhq.com) spend less than 5 mins per month worrying about sales tax. And yes, we deeply integrate w/ Shopify! :)

If your DTC business doesn’t work with Facebook ads, it likely won’t work at all. Here’s the truth: I see lots of DTC owners and operators say you need to test a ton of different channels (Pinterest, Snapchat, referrals, etc) to see what works. I couldn’t disagree more. When you diversify like this, you take resources away from the most proven DTC growth channel—Facebook ads. The I in ROI is not just cash investment but focus and energy investment as well. Say what you will, but they’re the most tried and true form of DTC advertising. The entire industry would barely exist without FB ads. If FB ads don’t work for your brand, it’s unlikely another channel will. It’s a great litmus test. I’ve seen it time and time again while scaling brands. I get that diversification makes sense in theory, but it doesn’t work in practice. Anyway, thought I’d share. Agree or disagree?

Excited to share that @NumeralTax has acquired the @SpendRuby team. And as part of this acquisition, we’re excited to welcome the entire Ruby Card team, including @ShariarK8, @jordanyaqoob, and @_AceroM, to Numeral. This marks our first acquisition, and it has been a long time coming. I first met Shariar, Jordan, and Miguel during @ycombinator's W23 batch. We became fast friends, given our shared experience building and supporting ecommerce brands. It turned out that I wasn’t the only one who had dealt with the nightmare that is sales tax. Shariar, Jordan, and Miguel will join our engineering team to help accelerate our global offering, including integrations and our industry-leading tax engine. Together, we’ll solve one of the hardest problems for growing businesses: sales tax compliance. This brings our YC founder count to seven and marks the opening of our new NYC office. We’re hiring for several roles across our engineering and sales teams. Join us?

Say hello to @numeral.com 🚀 Same great sales tax solution. Shorter URL.

Long-time listener, first-time caller! I had a blast with @TurnerNovak on @ThePeelPod. Growth marketing, t-shirts, custom jewelry, hiring, sales tax, and AI. We covered a lot! 🍌 And we talked about how all of the above ultimately led us to start @NumeralTax, get into @ycombinator, and raise our Series A from @benchmark. So fun, Turner! Thanks for having me. The pod is available wherever you listen to podcasts.

Schedule a wire transfer for $1,000,000 to your biggest competitor, six months from now. Now you’re motivated to get rich in 180 days, or you’ll be $1,000,000 in the hole. Why is no one doing this?

So many DTC operators want to try SaaS. Yet so many SaaS founders want a cashflow business. I left my DTC brand making over $10M/year to start a SaaS biz. I can tell you firsthand, that the truth is this:

Even Spiegel didn’t start Snapchat until he was 21. Brian Chesky was 26 when he started Airbnb. Patrick Collison was 22 when he co-founded Stripe. You’re never too old to follow your dreams.

All about private space, not public space. Horrible to visit without connections, great when friends host pool parties.

Q1 was a big one here at @NumeralTax Big in terms of revenue, customers, filings, our team, and of course, pieces of mail received by our virtual mailboxes! Here are just a few of the highlights ✨ - 3x’d the number of customers in Q1, vs Q1 last year 🤝 - Sales team crushing quota … multiple reps crossing 200%+ of quota in Q1 💪 - Hired 22 new Numerals (what we call ourselves) 💙 - Opened our new headquarters here in SF 🌉 - Announced our $18M Series A led by @benchmark 💰 - Rolled the dice at ShopTalk 🎰 - Sponsored the world's #1 podcast @tbpn 📈 The team has been grinding and growing. And we are hiring with openings across our engineering and sales teams. Ready to join us? Q2 should be a fun one! 🚀

ICYMI: Our pricing remains the same whether you're a brand doing a little over a million or if you're doing hundreds of millions. We charge you for filing state sales tax monthly/quarterly and a one-off fee for registering you in a state that you hit nexus in.

Ecommerce sales tax is hard. VERY hard. But against all ads, we have built a @NumeralTax, the most comprehensive sales tax compliance solution for ecommerce brands that's practically foolproof. In fact, we pay you if something goes wrong (yes, that's a screenshot from our pricing page). So yeah, in case you're on the fence, this should alleviate your concerns. Give us a try: numeralhq.com/demo

We just launched @NumeralTax on @ProductHunt! Thanks, @garrytan and @ycombinator, for hunting us this morning! It has been a long time coming, and we'd love for you to support the launch! 📈 Numeral puts sales tax on autopilot for leading e-commerce and SaaS businesses, offering intelligent workflows for registration, filing, and remittance alongside white-glove customer support. Thank you to our 1,000+ customers for trusting us with one of the least exciting parts of your business. 💙 If you are curious: producthunt.com/posts/numera…

Every Shopify store owner should be ecstatic right now. They just released Shopify Editions Winter ‘24. It has over 100 updates to help you grow your business and better serve your customers. I narrowed down the ten most impactful changes below:

"It's sales tax god in a box. It's super intelligence for sales tax." 🤣 Couldn't say it better myself, @jordihays and @johncoogan. My fav @tbpn @NumeralTax spot yet!

Love it! We should chat.

bigger than chamath’s anaconda

We're serving dozens of top-notch DTC brands like Obvi, Immi Eats, and Unwilted, and not one of them has churned or complained about our service. - We have the best service you can ask for - We're brand owners and CPAs - We know sales tax like the back of our hand Let us take sales tax off your plate—you've got better things to worry about.

Can someone let my controller know if this falls under “Meals & Entertainment” or “Professional Services”?

If you want to see an AI agent work the worst job on the planet, watch as Numeral’s tax agent navigates a state sales tax portal. Every time you remit sales tax, you basically have to navigate portals like this. I say “like this” because there are 50 states and 190+ countries, so of course no two are the same. Thankfully, it all boils down to a bunch of data entry and confusing rules to interpret and follow. So to an AI agent (like Numeral’s), it’s a breeze. But still, even fancy Cisco hold music can’t save how annoying this is. And if you’re a founder, you have to do this hundreds of times. Thanks to our team for making this happen; I wouldn’t wish this task on my worst enemy! (h/t @browserbase and @pk_iv - we use BrowserBase under the hood to run this, and couldn’t imagine it any other way)

I scaled multiple DTC brands to $10M+ in revenue without a full-time employee. If I had to start one today, I’d stay away from these four mistakes I made back then:

Poor machine - needs tips to buy electricity and upgrade software :(

I ignored important advice and had to relearn it the hard way. Here’s the story (and a cautionary tale): Six years ago, my friend and former Airbnb colleague @gustaf was driving me down to Mountain View to speak at a YC Growth Bootcamp. On that drive, he told me something I remember to this day: “The misconception with growth is that it doesn’t matter if you don’t have good retention”. It made complete sense. But I still ignored the advice. Instead, I started a low-retention business that was essentially a big SEO-hack. It was a jewelry brand. A short while into running it, I faced a massive problem: On the surface, things looked great. We were selling a lot. But if Google or Amazon rankings went down, so would our business. Even though we were good at acquiring customers, that’s not a durable advantage. We learned our lesson when starting our next brand, where our criteria for choosing a product were simple: Something people have to use regularly and predictably. We landed on daily supplements. We grew that brand to $10M+/year in revenue, with far better—but not perfect—retention. ~70% of our revenue came from existing customers, but over 90% were still churning after a year. We ran into the DTC sales tax issue while running this brand. While it was a headache to deal with, it set off a lightbulb in both @mrkevnliu's head and mine. → All DTC stores will deal with this as they grow → We just want a solution that will make the problem go away And that’s how the idea for @NumeralTax came to be. Not that we have 100% retention (although we’re gunning for it), but we’re keeping way more customers than any of our DTC businesses could’ve gotten close to. This is a combination of: → SaaS as a model → The issue we solve → Delivering a good experience Translation: Build things people need on a regular basis. It’ll make your life much easier. And if you want to read more about how we’re building Numeral (plus get actionable DTC tips in the meantime), follow me!

Last night, we teamed up with @intercom and @fondocom for a Founder Cocktail Class in San Francisco.🍸 Two classic cocktails and plenty of good conversation later... we were reminded that sales tax may be complicated, but cocktails don’t have to be. Shout out to @JoanneShang, @ccfromintercom, and Cassie for organizing this wonderful event! 🥂

If you work in DTC and aren't checking out Hampton's 2023 Ecommerce Analysis, you're doing yourself a disservice. It's full of valuable data every operator should care about. I won't give a full summary, but there are three takeaways I found interesting:

FYI: Cheap isn't always better. Remember that when you're buying software for your brands.

Only @shopbala_ could make resistance training look like a fashion campaign. What started as a napkin sketch in 2018 is now a nine-figure business with a community that treats ankle weights like jewelry. It’s proof that thoughtful design can reshape even the most ordinary product. In the early days, they shipped 75,000 orders out of their garage before landing on Shark Tank in 2020, where they walked away with $900k from @mcuban and @MariaSharapova. Their goal was simple: make fitness gear you don’t have to hide in the closet. Mission accomplished. Natalie Holloway and Maximilian Kislevitz built a movement around movement. We’re proud Numeral gets to keep their sales tax as tight as their brand color palette. Bala rocks! 💅💪

Had a chance to sit down with my good friend @gustaf at @ycombinator. A little-known fact is that we actually worked together at Airbnb before he joined YC and I started @numeral. And he was the one who urged us to apply to YC’s W23 batch. Since then, Numeral has become one of the fastest-growing YC companies. But our mission hasn’t changed: making sales tax and indirect tax compliance painless for founders and finance teams. Gustaf and I talked about those early days, fundraising during the batch (and later from @benchmark), our global expansion to support SaaS companies, and how Numeral is shaping the future of tax compliance with AI.

🍸 @NumeralTax x @intercom x @fondocom ... Join us! On August 21st, we are hosting a Summer Cocktail Class & happy hour! 6:00PM to 9:00PM PST at a 🔥 spot here in SF: lu.ma/vtcnc9zj If you're curious, I prefer my sales tax shaken, not stirred.

For the uninitiated: Sales tax in the US is a nightmare for ecommerce brands. You have to think about: - Registrations across states - Nexuses ($100k or 200 orders) - Filing monthly or quarterly - Reading/responding to random IRS notices - a ton of other sh*t It's ain't easy to manage this when you're running a 7, 8, 9-fig brand. Trust me, I have been there, done that. If you need a solution, DM me and I'll show you why you shouldn't be spending more than 5 minutes on this every month.

As someone who runs a SaaS biz & 8-figure brand, I can confirm there’s a ton of synergies. But I also miss sleep.

One of the biggest issue I faced while running Fling (8-fig DTC brand) was being compliant with sales tax. The existing solutions in the market doesn't cut—this one time we had to pay $20k in penalty simply because our *sales tax solution* messed up some compliance rules. It became so annoying that I along with @mrkevnliu and @jakeonrails started building @NumeralTax, a white-glove SaaS solution for ecom brands to file taxes and stay compliant. When I say white-glove, I mean you don't spend more than 5 mins every month worrying about this. LMK if you need me to show how (numeralhq.com/demo) we do this.

I'm excited for our first case study to come out this month 👀

Welcome aboard, @obviceo! Saving DTC founders headache one client at a time.

It’s getting HOT in Times Square! Thank you @brexHQ for putting @numeral on the big screen. What’s crazy is that in 1904, when Times Square got its name, there wasn’t any retail sales tax in the U.S. It wasn’t until 1930 that Mississippi became the first state to adopt a true retail sales tax, meaning it was charged at the point of sale to the consumer. Fast forward 121 years, and we’ve got an AI-native solution for U.S. sales tax and VAT compliance! 🚀

Listen to the guy who runs a $50m brand 🔥 For sales tax compliance, you wouldn’t find a better partner than @NumeralTax, I promise you that. Not only from the perspective of offerings but also how our relationship dynamic with the brands we work with.

Turns out the best way to measure growth is in miles… so we took the team to Maui to celebrate what’s been a banner year at @NumeralTax. From something like ~25 folks to start the year to 55+ folks today. And they’ve worked their butts off → 3.5x revenue growth, 1,500+ customers, and we’ve closed our four largest customers within the last two months. (𝘩𝘪𝘯𝘵: 𝘰𝘯𝘦 𝘰𝘧 𝘺𝘰𝘶𝘳 𝘧𝘢𝘷𝘰𝘳𝘪𝘵𝘦 𝘈𝘐 𝘤𝘰𝘮𝘱𝘢𝘯𝘪𝘦𝘴) If you told me 1,029 days ago that Numeral would be here… I’d have asked what you were drinking. Mai tais in Hawaii? Here’s to our amazing customers and team.🍹

CEO of @NumeralTax here - happy to help anyone if they have sales tax questions. Can put together a free audit too. DM me or email sam@numeralhq.com

A harsh wake-up call for DTC operators: Back taxes can eat up your profit and some if you’re not careful. While every brand differs, many operate with a 10% net margin. Now...

An unwelcome surprise for DTC stores owners: (Sorry to be the one to break it)

It’s @ycombinator Alumni Demo Day today! It's the first time it's been in person since 2019 (@NumeralTax was W23). Good luck to the ~90 companies presenting today! Would love to say hey if you see me at the event!

Two of the best, @moizali and @ShaanVP, put sales tax on autopilot with @NumeralTax...and you can too!

I’ve observed two DTC founder Archetypes: 1) Founders obsessed with brand. → You’ll go to their site and see studio photography and cutesy animations → You’ll open social apps and see them sponsoring influencers. → You’ll scroll LinkedIn and see them getting press. They’re masters of creating buzz. And don’t get me wrong, that’s great. But they often suffer when it comes to performance. These founders are often not great with Facebook ads, and are often overly controlling about ad creatives and copy. Even still, they get tailwinds because of the brand work they’ve put in. 2) Founders who see everything as a piece of data. On the other side of the coin are founders who are so focused on numbers that often neglect brand. → They’re masters of Facebook Ads. → They feel every dollar spent must generate ROI. → They won’t invest in anything they can’t measure. And while this works, it only works up to a certain point. The “ideal” DTC founder is able to reconcile both worlds. They understand you need to invest in things that can be hard to measure. They spend money on things that don’t have an immediate ROI (photography, creators, packaging, etc). That said, they aren’t signing up PR firms on 10k retainers. They invest in driving conversions and know the ins and outs of their LTV model. Ultimately you need to marry analysis with a good intuition of where to invest resources and capital. This balance is hard to strike, but it’s how great companies are built. What else would you add to either of these?

“These Teespring shirts we made in 2013 have a whole new meaning”

I’m extremely proud of this. Here’s how lash brand Doe was able to achieve: → A 95% reduction in time spent on sales tax management → $0 tax liability from sales tax mistakes → Effortless national expansion

🚨 Tax Update South Dakota changed its sales tax rate from 4.5% to 4.2% effective from July 1st, 2023 (9 days ago). They also, previously, removed the 200 transactions threshold from their economic nexus policy.

The TikTok news isn’t pretty for DTC brands. It may change the advertising and acquisition landscape for good. Here are 4 DTC-specific thoughts on what the ban would mean: 1) Meta Ads Will Get More Expensive This is purely a supply-and-demand issue. The ad dollars being spent on TikTok will have to be directed somewhere. Meta is currently the only logical answer. When demand shoots up like that, ad costs will, too. 2) Brands Relying on TikTok Shop are in Trouble TikTok Shop was a strong driver (the strongest, in some cases) for many brands. Losing that overnight will not bode well for their health. Finding another acquisition channel should be priority number one. 3) Brands Relying On Short-Form Organic are in (Less) Trouble Outside of TikTok Shop, many brands drive site traffic with organic short-form content (from the brand account or creators they hire). If this gets banned, that traffic will also be gone. Now, other short-form content platforms brands can still use (IG Reels, YT Shorts)—but losing the biggest of the three sure doesn’t help. 4) Meta’s Competition Vanishes To this point, TikTok’s been the only driver for Meta to innovate and compete for performance ad dollars. Meta needs them to have a chokehold on advertising (and social shopping, to some degree). Even if Instagram can temporarily fill the gap with short-form content traffic and in-app shopping, it’s a short-term fix for a long-term problem. Meta already tried their version of TikTok Shop with Facebook Shops—it didn’t pan out because they couldn’t get nearly as aggressive as TikTok did. My short-term advice for DTC brands: 1) Keep an eye out for future updates 2) Diversify as early as you can (if you haven’t already) What other impact(s) did I miss here?

DTC snack brands are notoriously hard to scale. Factoring in lower AOVs, spoilage, and bulky shipping —there isn’t much room for margin. That said, it’s not impossible. You just need to get creative in how you sell. 1) Obsessed Customer Base Each snack brand I know of that is doing well in DTC appeals to a movement or sentiment extremely well. Keto, carnivore, low-FODMAP —that sort of thing. A lot of this comes down to positioning, but the more you can appeal to a hyper-specific consumer segment, the more they’ll be willing to pay (and the less willing they’ll be to look for alternatives). 2) Higher Order Minimums The most successful brands we work with have large pack sizes with higher order minimums than you’d imagine. While it may hurt conversion numbers, this makes AOV and shipping numbers sustainable for the brand. I’ve seen minimums for fairly simple snacks at $50+, leading to AOVs as high as $100. 3) Recurring Purchase Most of these brands offer subscriptions as well. It makes sense. Especially with a cause-focused customer base, setting up recurring purchase options works wonders for LTV and, by extension, the amount of CAC you can tolerate. Anyway, I thought this was worth the share. Anything else to add in terms of DTC food products?

Helping brands like @immieats, @FreshSends, @eatmuddybites, and @my_obvi spend less than five minutes per month on sales tax.

No matter who you use to handle your store’s sales tax compliance, make sure they have the virtual mailbox facility. States, counties, and cities send you a ton of mail. Most of them are irrelevant but there are a few crucial ones (like requesting additional information on tax filings) that require your attention. At @NumeralTax, we receive, read and reply to your physical mail proactively so that you don’t get hit with unnecessary penalties for ignoring some silly notification. This also ensures that you’re not inundated with emails that you have no clue what to do with it.

“We’re not EBIDTA profitable, but we are EBIPJPERST profitable.” What does that mean? “Earnings Before Interest, Parties, Jets, Paying Employees, and Remitting Sales Tax” Oh so you’re not profitable? “Not even close.”

Brand founders shouldn't worry about sales tax—they have 100 different things to work on to grow the business. I'm an @immieats fan and a customer and it's a privilege to serve top brands like these and help manage their sales tax compliance!

DTC operators need all the time they can get back. If you’re running a brand, you need to handle: → Marketing/advertising → Inventory tracking → Warehousing → Fulfillment → Social And a million other things. Here's the truth: You can put a team in place, but DTC brands are generally fairly lean. It’s all hands on deck all the time if you’re an operator. The truth is that protecting your time and only working on high-leverage parts of the business are the only ways you’ll grow. And in my (biased) opinion, outsourcing sales tax filings and management is one of the highest-leverage things you can do. So many DTC operators face the issue of their sales tax liabilities growing just as fast as their brand. As your brand grows, the amount of time you spend on sales tax each month does, too. I strongly suggest you outsource it. While I think you should use Numeral for a variety of reasons (white-glove service, compliance guaranteed) — you can use whoever you’d like. But if you find yourself spending 40+ hours per month on sales tax, you’re doing something wrong. You can do it in less than 5 minutes per month and never pay a late fee again with Numeral. DM me and I’ll show you how.

Stoked to have @NumeralTax sponsoring the Finance Operators podcast with @MehtabKarta and @drewfallon12! As always, amazing content from the @9operators team!

Avalara puts you in 1/2/3 year contracts. Now you know why 50% of @NumeralTax's customers have switched from them.

"Mom, how did we get rich?" "Sales tax compliance, sweetie. Basically, your dad’s company plays a union rep between terrified founders and state websites built in ‘99.”

Always a blast to speak at @ycombinator! So many exciting companies this year, as always.

Just told my 7 year old nephew that Meta poached like 10 people who worked on GPT-4o, Gemini, ChatGPT, Waymo perception, and god knows what else She was quiet for a second and then said “Given the level of model convergence, talent is the last real differentiator. If you can’t win on distribution or data moats, you hire the people who actually built the thing.”

If you sell on Amazon or TikTok Shop, this might be worth a listen. Hopped on the @9operators pod with @seanfrank, @JasonPanzer, @mbertulli and @mikebeckhamsm -- we got into sales tax horror stories, exits blowing up in diligence, and why nobody audits faster than the state of Minnesota. And then Sean told this brutal story: His accountant didn’t realize Amazon was already remitting sales tax. So for nearly two years, they sent the full tax amount again. For TWO YEARS! Over $1M out the door, and he's still waiting on $350K back. This kind of thing happens more than you'd think. When marketplaces like TikTok Shop or Amazon already remit tax, a bad setup can mean you’re paying it again, on money you never even collected. And stuff like this can wipe out your margins, or worse - kill a deal if it surfaces late in diligence. Full episode was a fun one, check it out (link below).

Airbnb could make searching a million listings 10x easier. Instead they relaunch cooking classes for the 10th time…

I've heard way too many stories of DTC stores getting burned by poor sales tax providers. They had to pay easily-preventable late fees and interest penalties out of pocket. It’s terrible. Here’s what to look for in your sales tax provider to make sure this never happens to you: 1) Month-To-Month Incentive I’ve heard serious complaints from prospects claiming providers lock them into long-term contracts, and give minimal service post-signature. Instead, find one that works month-to-month—meaning they have to work to earn their fees. 2) Notice Management The amount of sales tax notices you have to keep up with as a DTC brand feels like a full-time job. But you shouldn’t do it. Your sales tax provider should handle this for you. They aren’t providing adequate service otherwise. 3) Industry Specialization Each industry (especially ecommerce) has sales tax nuances others don’t. I strongly recommend you find a provider that specializes in what you sell (ecommerce products, SaaS, etc). They’ll be well-equipped to handle the landscape better than a general sales tax provider. That’s all for today. While I encourage you to find what’s best for you, @NumeralTax fits the bill on all three of these points (and more)—just saying. DM me if you want a free demo!

Don’t worry, that tiny pixel is Numeral’s headquarters

This is why all compliance mail needs to be auto scanned & classified by AI. Because most mail is trash until it’s a critical letter. @NumeralTax

If you think DTC is hard now, you have no clue what’s coming. When I started in ecommerce, getting a site, product photography, and product production in place could cost upwards of $100K before you made a single sale. Today: → There are almost-perfect out-of-the-box site templates → AI can do most of your product photography → You can white-label products instantly Translation: The barrier to entry has been going down, and will continue to decrease over time. That also leads to a lot of products and brands looking and feeling the same. So, if I were a DTC brand trying to differentiate (and survive) in 2024, I would: 1) Invest more in R&D, to make a truly different product than my competitors. 2) Protect myself with whatever necessary IP, patents, and trademarks I need. 3) Do necessary scientific research on my product (if I made consumables). Even still, it won’t be easy—but you must give yourself the best chance at success. TLDR: The barrier to entry for DTC continues to go down. Protect yourself however you can.

I ran bootstrapped businesses for years. After having been at a hyper-scaler startup that died from raising too much money, I thought they were the "right" way to build a company. My time at YC changed that for me. Let me explain: I come from a DTC background. → Lean teams → No outside money → Solid cashflow, but no massive outcomes And for the record, I loved it. But when @mrkevnliu and I decided to start @NumeralTax, we had a moment of realization: Building a SaaS business to serve a massive market requires engineers, sales, and tons of other heavy expenses upfront. Naturally, we realized we had to raise money. We were fortunate enough to get into YC. Within a few weeks, my view on company-building shifted completely. You're instantly surrounded by a culture of audacious ambition. To them, a $1M/year cash flow business is playing the wrong game. As cliche as it sounds, the insane levels of ambition coming from peers, not just people on a podcast or social media, made me think bigger. My big takeaway here is that ambition is often a function of your environment. I'm curious, what do you feel calibrates your level of ambition?

I’m not on the TikTok Shop train just yet. There are still three issues I haven’t seen addressed, and I’d be wary of if I were operating a DTC brand today:

"Data is the plural of anecdote" -@joshelman speaking with @walkerteespring during @teespring fireside chat.

Pro tip: become a Numeral customer and the pixel will let you get back to Temu ads

This is the most common question brand founders ask me: How do I know whether I have physical or economic nexus in any state? It’s simple. If you have a physical presence in any state, be it a store, warehouse for inventory, or an employee based out of that state, you have a physical nexus. And typically, if you exceed $100k in sales or 200 transactions (i.e., orders) over a year in a state, you have economic nexus. In either case, you’re liable to register, collect and remit sales tax in that state. I hope that clears it up.

Rival CEO spotted me in the elevator the other day, and tried to prank me. She walked in, pressed every button, and jumped out before I could say anything. Probably thought she got me real good. Wrong. I got out at every floor and scheduled discovery calls with every single person in the building. Didn’t matter how senior they were; I got them on the calendar. Bet my rival feels really stupid right about now. I’m not sure how many qualified leads there are at the DMV, but that’s besides the point.

We started as… an Excel spreadsheet. Today, I’m excited to share that @numeral has crossed 2,000+ customers, from @ridgewallet to @eightsleep, Manus, Graza, Lucy, Grüns, Mike’s Hot Honey, Kitsch, and so many more. 🎉 Sales tax is painful. A terrible waste of time for growing businesses. Hundreds of pieces of physical mail. Constantly changing rules. Filing frequencies. Sales tax holidays. And don’t even get me started on VAT/GST. It’s a mess. But that’s exactly why Numeral exists. We’ve built the end-to-end solution. What pushed us to start Numeral was actually one phone call. A two-hour call with the Alabama Department of Revenue. I was trying to make sense of a piece of mail I’d gotten. There had to be a better way. Fast forward → one of my favorite features today is our virtual mailbox. We collect, process, and action all of that tax mail for our customers. Because sometimes, missing just one letter can cost you, even if you’re doing everything else right. Thank you to our customers for trusting us with your sales tax and VAT!

Are you ready to sear your steak? Couldn't have said it better myself @jordihays @johncoogan

Here’s a fun story: Back when I was running DTC stores day-to-day, I had a hunch: If I could rank for a ton of long-tail keywords, I could generate a ton of sales on organic traffic alone. This led me to start Dear Ava—a company geared towards women selling gifts for all kinds of people in your life. We had gifts for Moms, teachers, pregnancies, weddings—you name it. The catch? No matter the SKU, the product itself was the same (see the picture below). We just changed the background of each gift to have a relevant message—which, of course, cost almost nothing. And let me tell you, it sold well. It worked. Across all the platforms, we sold over half a million units. We ranked on all kinds of long-tail keywords in Google, Etsy, Pinterest, and Amazon (”best gifts for piano teachers”, for example). We still ran paid ads, but this unlocked a whole new growth lever a lot of brands neglect, in my opinion. Anyway, I later sold the brand—but if you check the site, they’re still doing similar things. The takeaway is that you don’t need a unique invention or one-of-a-kind branding. You need to respond to a market need. I guess that goes for any business, now that I think about it. When did you learn this lesson?

And your finances. We're working with a few brands at @NumeralTax that are gearing up for a sale in <6 months or less and tidying up their taxes is of utmost importance.

We're bringing together a curated group of finance leaders from SF's top SaaS, Fintech, and AI companies for an evening of conversation, connections, and great food. We’ve prepared some spicy discussion topics around scaling finance ops, AI in accounting, and the evolving CFO role. 📍 Potrero Hill, SF 🗓️ September 17, 2025 from 6:00PM to 9:00PM 🔗 lu.ma/r3gwcooe @NumeralTax is excited to be working with @SequenceHQ_ x @runwayco x @meet_campfire on this fantastic event. See you there?

Repeat after me: In Illinois, Twix is taxed at 1%. Snickers is taxed at 6.25%. In Illinois, Twix is taxed at 1%. Snickers is taxed at 6.25%. In Illinois, Twix is taxed at 1%. Snickers is taxed at 6.25%.

Some people meditate. Some people do ice baths. I prefer the 8am VC call where you get asked “what's the broader vision here?” for something you launched 3 weeks ago. By the end of the call, you’ll have invented 2 new product lines, a tactical partnership with Salesforce, and a marketable reason for why you started the company in the first place. No need for therapy, just “pitch mode”.

Reminder for DTC operators: You can spend 95% less time on sales tax and pay zero late fees or penalties. Just ask Amberjack. (thread)

Your ads should be dumbed down. Too many DTC companies commit the same marketing sin: Prioritizing being clever instead of clear. Certain brands are still making ads that take a few seconds to “get”. That works as a 30 sec TV spot—but not as a social ad. With TV ads, your viewer is forced to watch your entire spot. With Facebook and TikTok ads, they’re not. More than that, no true “thinking” should be required to understand the problem you’re solving or the product you’re offering. It should be clear as day. My advice for you: → Start with your product in-frame → Ask a thought-provoking question → Call out your ICP and/or their pain points This will make it hard for the viewer not to understand what you’re offering. As a general rule of thumb: the less thinking required for the viewer, the better the ad will perform. What do you think? What else would you add?

Ecom sales tax? Stuff of nightmares!

Happy National Ice Cream Month 🍨🍧 💡Did you know that an ice cream cake or a similar product is taxable in Wisconsin if it meets the definition of "prepared food"? "Generally, if a person mixes ice cream and one or more other food items to form an ice cream cake or ice cream bar, the retail sale of the ice cream cake or bar is taxable as a sale of prepared food. If the ice cream cake or bar is prepared by someone other than the retailer, it is not taxable unless it meets one of the other prepared food definition categories." — WI Gov. Sales tax is fun and messy! 😅

Thank you for the support 🙏 We love working with legends!

Beyond excited to see @numeral's $35M Series B featured in TechCrunch! Thank you, @MTemkin, for telling our story and covering our new round of funding, led by @MayfieldFund with participation from @benchmark, @ycombinator, @uncorkcap, and @mantisVC. 👉 techcrunch.com/2025/09/18/nu…

The first thing you see when jumping on a "quick pricing call" with Salesforce

Some cool updates from the CPG world this week! Take a look 👀

Excited to share that @NumeralTax received not one but 4 new badges as part of G2's Spring 2025 analysis of Sales Tax and Vat Compliance solutions. Between us, I'm most excited about the Best Support badge. 🥇 We started Numeral 2+ years ago to solve the nightmare that is sales tax for growing ecommerce and SaaS companies. Today, we work with 1,000+ of the best brands, including Ridge, Graza, and Immi, and even a few AI companies. Ready to put sales tax on autopilot? And thank you to our customers for leaving reviews! 💫

Stories like this are one of my favorite parts of my job. In early 2020, Carson Crane was facing an issue. The coffee brand he started as a result of COVID was growing. This growth would spawn problems he didn't anticipate...

I'll share these stories for as long as you'll listen. Right before the pandemic in 2020, Jesse Hiss and his wife Ty started Fresh Sends — a flower delivery service with a DTC touch. They faced initial obstacles, but overall, the business began to thrive quickly...

We're super excited that you switched, Jake! 🙌

.@foundersatwork remising on @walkerteespring's underwhelming @ycombinator pitch at @teespring fireside chat.