🎧 Listen: Castos | 📺 Watch: full episode on YouTube
An AI can sort your bank export in seconds, but Maya Weinreb – whose team keeps the books for 150+ companies – says the answer is only as good as the input and your understanding of it. Maya is the founder and CEO of Solvency Now Bookkeeping, and she told host Jeremy Rivera on this episode of the Unscripted Small Business Podcast what she finds in a new client’s books, how she thinks about sole props, S-corps and LLCs, what changed with 1099s this year, and why the people who ask AI to do their bookkeeping still need to know what good books look like.
Twenty years of bookkeeping and a team behind every client
Maya has been doing bookkeeping since straight out of high school, which she says is more than 20 years now. In her words, “I have currently over 150 companies that my team does bookkeeping for,” and she’s done books for hundreds more over the years.
The team part matters to how she works. A lot of bookkeepers, she says, are “Sally down the street.” They get swamped during tax season, or their kid gets sick, and nothing gets done. Her firm writes down the procedures for every account:
“We have everything standardly written, exactly what every client needs, so another bookkeeper can come in and take over if they need to.”
Most new clients have a mess or no records at all
Jeremy asked what low-hanging fruit she always finds when she takes on a new account. Maya’s answer: bookkeeping is putting order in people’s finances, and the people who call her usually don’t have order. “They have either they have a mess or they have no records at all.” That’s also why she finds bookkeeping easy to sell. “Because they wouldn’t be calling me if everything was great.”
When a new client does have books, she looks at them together with the owner and asks a few plain questions. “Do you have a bank account called Office Supplies?” No. “Is your credit card negative 350,000 balance?” No. Her point is that a lot of what’s wrong is visible fast: “there’s things that are so easy to see in just five minutes that their books are wrong.”
The other kind of new client has no bookkeeping and needs to file taxes, or hasn’t filed in a few years and has no data to file with. Then the job is getting the books set up from scratch.
The real pain is a tax deadline with no records behind it
Jeremy asked what causes the most heartache for the people who come to her. Number one, Maya says, is that “they need to file taxes and they can’t because they don’t have records.” They don’t know where to start, and it’s overwhelming.
The second is books that are wrong in a way that costs money. An owner hands the data to their CPA or tax preparer, and “it shows their income being double what they thought it was, and now they’re gonna pay taxes on way too much money because their books are wrong.”
The third is a bookkeeper who missed something: payroll taxes not filed on time, a bill not paid, 1099s never filed. Maya was careful not to blame every other bookkeeper. Sometimes the client never paid for that service. But she thinks a good bookkeeper brings it up anyway, with something like:
“Hey, you’re not paying me for 1099s, but 1099s are coming up due. Would you like any help on that or do you have it under control?”
Freelancers need books from the first dollar, not the perfect setup
Jeremy has been a freelancer, sometimes alongside a W-2 job, and asked what solopreneurs, consultants and freelancers need to understand. Maya says some people have a knack for the basic concepts of income, expenses, profit and loss, and some people find it really hard. If it feels scary, she says, at least hire someone as a coach or consultant before you’re ready to hire a bookkeeper. She does consultations where she explains how bookkeeping and QuickBooks work so people can start on their own.
She was just as clear that books are not the first job. “The most important thing when you’re starting a company or a freelance or solopreneur is go and make money.” Don’t stall in analysis paralysis trying to build the perfect thing before you sell anything. But once money is moving, even if it’s just you and one bank account, “you need books, you need records.” A consultation that runs a few hundred dollars can get you started, she says.
If you want the cash side of this explained by a CFO, Meaghan Wall on cash flow is a good companion listen.
A CSV in Claude is a start, and you still want a real ledger
Jeremy asked whether there’s really that much more to it. He can download a CSV from his bank, drop it into Claude Code and ask it to sort his expenses and tell him what his major bills are. Maya didn’t wave that off. “Claude can do so much now, it’s amazing.”
She still recommends a real ledger. You could build your own app or keep files on your computer, she says, but it’s hard to keep everything together, so “even if you’re using Claude to help you, I’d still recommend getting a software like QuickBooks Online.” The bigger reason to keep records is taxes: “you need the records so that you can pay as little taxes as possible, but also make sure your taxes are paid on time and paid correctly so you don’t end up in trouble with the IRS.”
Picking a sole prop, S-corp or LLC is a profit question
Jeremy asked how to think about filing as a sole proprietor versus setting up an LLC or S-corp, and whether handling a lot of cash changes the answer. Maya walked through it, with her own caveat that it differs by your situation and what your CPA or tax planner tells you.
A sole prop “is gonna be just the easiest because there’s nothing to do.” It’s a schedule on your taxes. Once you’re making money, though, she says it stops being an advantage, because on a sole prop “you’re paying self-employment taxes as well as income taxes” on all of your profit.
“It differs by your situation and what your CPA or tax planner tells you, but most of the time when they get to around 50 to 100,000 revenue and decent profit, people are going to recommend that they do an S-corp election.”
Her explanation of why: as an S corporation you pay yourself a salary, and “it has to be the IRS definition of reasonable salary. So you can’t just be like, it’s a dollar.” It’s what you’d pay someone doing your job. Then, she says, “any profit on top of your salary only has income taxes.” C-corps, in her experience, usually make sense for bigger and publicly traded companies, with very few small businesses benefiting. Solvency Now has a short explainer on what reasonable compensation is if you want to go deeper before you talk to your CPA.
On cash, Maya says the entity doesn’t change anything. Every dollar has to land in a bank account and then in your books. “Now, if you don’t track it, then technically that’s like fraud to the IRS.” Her practical rule: “So you just have to take it all, put it in the bank, and then spend it.” Spend it first and you’ll be trying to remember what it went to. As she put it, “the IRS says all income needs to be tracked.”
Handing your books to AI is like handing them to your great aunt
Jeremy asked how AI and answer engines have changed her industry, and whether they just tell people what they want to hear. Maya uses AI all day. She has agents helping her with all kinds of things, “but not client bookkeeping because there’s a lot of security and things involved.”
When people tell her “I’m just gonna have AI do my bookkeeping,” she hears something familiar:
“I’m gonna have another bookkeeper or my great aunt Sally Sue or my friend’s neighbor’s cousin’s best friend do it. You don’t know what you’re gonna get. And you don’t know what you don’t know.”
She turned it on herself, too. She told Jeremy she needs to learn marketing better, “because otherwise when I hire marketing people, I don’t know if they’re doing a good job.” Bookkeeping is the opposite for her. “I could look at bookkeeping that Claude churned out and I can tell you if it’s right or not. And Claude does a lot of things right, but it always depends on the input.” If you don’t understand bookkeeping enough, she says, “you’re gonna sometimes give it wrong prompts, wrong input, and get wrong answers.”
Her example of a check you need to be able to make: say you know you made ten thousand dollars and spent eight thousand. Was that spending on tax-deductible items? Was it expenses on the profit and loss, or “was it balance sheet items that wouldn’t count the same way?” If you can’t answer that, you can’t judge what the AI gave you.
She also sees the same gap between AI tools. Maya uses a tax AI that “pulls data directly from the IRS and state tax laws,” and she says she can run the same research there and in ChatGPT “and not get the same answers.” She trusts the tax AI more, and sometimes pastes its research into ChatGPT to explain it more simply. But “I’ve had ChatGPT give me wrong answers.” She loves how fast it makes everything. Her bottom line:
“The answers are gonna depend on the input and your understanding.”
One more thing she flagged about all-AI bookkeeping firms: “it’s hard to find someone to talk to when you need to understand your books.” She told a story she’d heard about an investor-backed AI bookkeeping company that made so many mistakes it hired outside bookkeepers to fix them, until the cost shut it down and, in her words, “it wasn’t ever really AI in the first place.” At her firm, “you get replied to within one business day. And if you want to talk to someone, you can talk to someone.” If you’re figuring out where AI fits in your own back office, James Ernst on fixing the workflow first is worth a listen.
The 1099 threshold changed, and the IRS is sending more notices
Jeremy asked about the biggest regulatory changes she’s seeing. For the service and professional-services businesses Maya works with, “the biggest thing for the industries I help is the new 1099 rules.” She says that for many years you had to 1099 anybody who provided a service, wasn’t a corporation, and was paid more than $600. Then:
“This year it just changed, so now it’s $2,000. And it’s going to continue changing every year because it’s supposed to be indexed to inflation.”
That’s Maya’s read of the rule, so confirm how it applies to you with your CPA or tax professional. She sees the higher threshold as the easier part. The harder part is that, in her view, the IRS is “being more strict about records and record keeping” and non-filing penalties. She also says the IRS is using AI now, and in her tax and accounting groups people are seeing more notices and penalties than ever. Because of the AI, she says, “some of them are wrong and taking forever to dispute.”
Her advice came from her dad, minus the words he actually used: “if you want to get out of trouble, don’t get in trouble in the first place. So just do it right the first place.” In practice, that means every time you pay someone who might be a contractor, and she says far more people count than most owners think, “make sure you get them to fill out a W9 before you pay them so you can send them a 1099 in January.”
When Stripe and your 1099s disagree, your records settle it
Jeremy raised a freelancer’s headache: what if a payment processor like Stripe reports one number and the 1099s you received show a smaller one? How do you keep the IRS from deciding you made more than you reported? Maya’s first answer: “first you have to have really good records.” If you can show every dollar that came in, the forms make sense.
Her second answer is that everyone, bookkeepers included, has to file correctly. Her examples: if you pay a contractor “with a credit card, you don’t file a 1099.” And “if you pay them through PayPal friends and family, you do have to file a 1099, but if you pay them PayPal business, you don’t.” Those are her rules of thumb, and she says certain ones get complicated, which is why you want a bookkeeper who stays on top of it. Then, if the IRS questions it, “You have the backup,” and it reconciles to your bank accounts.
TikTok tax tips are true only in certain situations
Asked for myths, Maya pointed at TikTok tax and bookkeeping advice. “It’s not even that it’s like a hundred percent false.” Buying a vehicle as a write-off, for example, only helps in certain situations. “Yeah, that is true in certain situations. And you don’t know what those situations are unless you’re looking at your entire tax picture.”
She hears about the misses from the CPAs she works with: people trying to write off days of a house they rent and don’t own, or claiming the whole house as a home office because they film reels in every room. Her favorite is clothes. People want to write off clothes they bought for business. She doesn’t tell them they can’t. “I tell them the IRS will not agree,” and if they want to fight it in court, that’s up to them. In general, she says, the IRS approves uniforms with your logo, and “it’s gonna be like steel-toe boots for construction, hard hats for construction. That’s about it.” An influencer’s outfits for reels still count as personal, because you can wear them in your personal life. And it’s the CPA who has to sign off, so she sends those clients to their CPA.
Opening in another state means deciding what the new location is first
Jeremy asked about a business expanding into a second state, the question one of his clients, a company that installs precast concrete walls in Florida, is facing as it goes multi-state. Maya would tell them to talk to their CPA or tax professional first. The first decision, she says, is whether the new location will be a separate company with its own EIN and its own books, or a section of the same company you just want to see separately. After that, it’s not so complicated, just more tracking.
Payroll is the harder part. Each state has its own rules, and while her team can register payroll in any state, she says “these systems are pretty ancient sometimes,” and you end up with a lot of notices. Sales tax is the other one. Her firm doesn’t do sales tax work, and she recommends a sales tax professional, because some states tax only certain parts of a sale, even for construction companies, and “you don’t want to owe sales tax because you didn’t know you were supposed to pay it.”
An LLC is a legal shield, not a tax break
Jeremy brought up rental property. His father-in-law may be moving, and Jeremy mentioned his friend Alex Zweydoff of ClearLead Digital, whom he’d just interviewed and whose firm does property management digital marketing. Should rent come in through an LLC or as regular income? Maya started by clearing up a question she gets a lot:
“There’s literally no tax benefits to doing an LLC, but there’s legal benefits to having an LLC because it’s a limited liability company.”
Most of her real estate investor clients put each property under its own LLC, she says, so if somebody slips and breaks a leg, the LLC is liable and not them personally. On taxes, “If you’re a single member LLC, your taxes are the same as a sole prop.” It does add an extra return and yearly paperwork, which she calls “almost like insurance.” For the legal side of setting one up properly, Phil Crowley’s story about an operating agreement that wasn’t one is a useful warning.
Her bigger point applied to anything that earns: “if you have anything that’s making you money, you should treat it as a company.” If you don’t, she asks, “what is it then? A savings account.” When a property starts losing money, you need business records to decide whether to invest more, sell it, rent it or hold it.
Go build the thing, and keep records from day one
Jeremy asked what idea Maya would put in the head of someone about to start a business. As an entrepreneur herself, “I would say go do it.” Don’t analysis paralysis it, she says, and use AI and agents as much as you can. As a bookkeeper:
“Have good records because you’re gonna need them. If you want an investor, you have to have records. If you want to file your taxes, you have to have records. If you want to get a loan or an SBA loan, they’re gonna wanna see your records.”
And she means real books. “It can’t just be like save your bank statements.” You need “profit and loss, balance sheet, and they have to make sense. They have to be accurate.”
Her parting advice went further. “I think that everybody should have a company,” she said, even if you’re an employee, because AI and AI agents let you do so much on the side. As companies hire more AI agents, she thinks employees will need to be really skilled in certain areas. There’s probably somebody already doing your idea, “and they’re not doing it as good as you could do it.”
“Go build that thing that you want to build because now is the time to do it.”
Maya’s mission statement for Solvency Now is “complete and perfect financial records for the business owner’s peace of mind,” and her personal reason for it is simple. She knows most businesses fail in five to ten years, “And I want to do what I can to help them succeed.”
Run Maya’s five-minute check on your own books this week. Does every bank account in your books match a real account? Does any credit card show a balance that can’t be right? Do you have a W-9 on file for every contractor you paid this year? And if AI is sorting your transactions, could you tell whether it put something on the profit and loss that belongs on the balance sheet? If the answer is no, Solvency Now offers bookkeeping services for small businesses across the US and 1099 filing, and you can book a discovery meeting with Maya.
Also on Unscripted Small Business
Maya’s case for treating anything that earns as a company pairs with Cecily North on treating the side thing like a business, and Sal Tirabassi on what a fractional CFO actually does picks up where clean books leave off.
Want the step-by-step version? Use the free Contractor Paperwork SOP built from this episode – eight steps and a printable one-page checklist.
Two more takes on this conversation: what marketers should learn from why AI output depends on the input on SEO Arcade, and Jeremy’s own reflection on knowing enough to check the work.
Connect with Maya
- Solvency Now Bookkeeping: solvencynow.com
- About Maya: Maya Weinreb, Founder and CEO
- Contact: get in touch with Solvency Now or call 813-336-1574
- LinkedIn: Maya Weinreb
- Instagram: @solvencynow_bookkeeping
🎧 Listen: Castos | 📺 Watch: full episode on YouTube
This episode is supported by our sponsors: uSERP, a GEO agency that helps brands get found in AI search, and Oleno, which gives a whole team the same shared context so everyone uses AI the same way.
Sponsor disclosure: uSERP, Oleno and ClearLead Digital are paid sponsors of the Unscripted podcast network. Links to them are marked as sponsored.
This article shares Maya Weinreb’s views from the episode. It is not tax advice. Talk to your CPA or tax professional about your situation.
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