Tax strategy for the way modern founders actually build.
AI-native businesses, indie SaaS, agencies, creator monetization, and consulting practices generate high margins on lean overhead. The tax leverage is enormous — and most generalist preparers miss it. We build the entity, retirement, and multi-state framework that compounds your after-tax return year after year.
The full founder tax stack.
- Entity selection and timing — Schedule C, single-member LLC, S-corp, or C-corp
- Reasonable compensation studies for S-corp owners
- §199A / Qualified Business Income deduction optimization (including SSTB analysis)
- §174 software-development capitalization and amortization tracking
- Retirement-plan stack: Solo 401(k), SEP-IRA, mega-backdoor Roth, defined-benefit overlay
- Accountable plans, Augusta rule (§280A(g)), and home-office substantiation
- Multi-platform 1099 reconciliation: Stripe, Gumroad, Beehiiv, Substack, YouTube, Patreon, Whop, Lemon Squeezy
- State economic-nexus analysis for SaaS, digital products, and cross-border services
- Estimated-tax planning and quarterly safe-harbor compliance
- Owner 1040 coordination — equity, brokerage, crypto, and entity K-1s on one return
Lean businesses with high margins are uniquely advantaged — if the structure is right.
A solo founder netting $400K from an AI agency or SaaS app has more usable tax leverage than most W-2 earners making twice that. The question is whether the structure captures it. Most generalist preparers will not even surface the choices.
Entity is the multiplier
The right entity — S-corp with documented reasonable comp, or C-corp positioned for QSBS — can convert a six-figure SE-tax bill into a four-figure one and unlock retirement-plan capacity on top.
Retirement stacking is real
Solo 401(k) plus mega-backdoor Roth, with a defined-benefit plan layered on for older founders, can shelter $70K to $300K+ annually. Most solo preparers never set this up.
§199A is on the table
Qualified Business Income deduction can shave 20% off pass-through profit — but the SSTB rules, W-2 wage limits, and UBIA tests have to be modeled. Consulting and creator businesses sit on the edge of the SSTB line.
§174 is the trap
Software-development costs must be capitalized and amortized over five years under current §174 rules — not deducted in the year incurred. The cash-tax impact for app builders and AI tool developers is significant. We track and document.
Multi-platform 1099s
Stripe, Gumroad, YouTube, Substack, Patreon, app stores, affiliate networks — your gross receipts are scattered. Reconciliation and consolidated reporting is the foundation of every other strategy.
State nexus quietly compounds
SaaS and digital products are taxable in roughly half of U.S. states. Cross a sales threshold without registering and you accrue liability silently. We assess and register where required.
Built for high-margin solo and small-team operators.
AI-native founders
Building agents, copilots, AI tools, vertical SaaS — generally lean teams, fast revenue, real §174 and §199A questions on day one.
Indie SaaS operators
One- to five-person SaaS businesses with recurring revenue and customers in multiple states. Sales-tax automation, MRR-based estimates, and entity efficiency.
Agency owners
Solo or small agency principals — marketing, dev, design, AI consulting. S-corp election, comp study, and retirement plan typically pay for the engagement many times over.
Creators & educators
YouTube channels, paid newsletters, info-product creators, course operators. Multi-platform 1099 reconciliation, equipment depreciation, and home-studio substantiation.
Independent consultants
Senior W-2 alums going independent — strategy, engineering, finance, legal. The transition year is when entity, comp, and benefits are decided correctly or expensively.
Founders pre-Series A
Pre-revenue or early-revenue C-corps eyeing QSBS qualification, 83(b) filings, and the founder-equity decisions that show up at exit five years later.
A representative founder engagement.
Year-one set-up plus annual planning and filing. Anonymized, illustrative, real shape.
Q1 — Structure decided
Entity selection modeled with three-year cash-tax projection. S-corp election filed with late-relief if appropriate. Reasonable-comp study documented.
Q2 — Retirement stack live
Solo 401(k) opened with mega-backdoor provision, contribution targets set, payroll integrated. DB plan added if income and age support it.
Q3 — Nexus mapped
Sales-tax exposure assessed across all U.S. states, registrations filed where required, automation tool selected and wired into Stripe.
Q4 — Year-end optimized
Estimated taxes reconciled, §199A and §174 positions confirmed, charitable and equipment timing modeled, owner-1040 prepped for January.
What founders ask on the first call.
When does an S-corp election make sense for a solo AI or SaaS business?
Once net profit clears roughly $80K, an S-election plus reasonable compensation typically reduces self-employment tax meaningfully. Below that, the cost of payroll, separate filings, and reasonable comp documentation often outweighs the benefit. We model both paths in dollars before recommending.
Can I still deduct R&D expenses or do I have to capitalize them under §174?
Under current law, software-development and other §174 research expenditures must be capitalized and amortized over five years (fifteen for foreign research). The cash-tax impact for app builders is significant. We model it, document the §174 classification, and apply any retroactive relief that becomes available.
Do I need to collect sales tax on my SaaS or digital product?
Depends on the state. Roughly half of U.S. states tax SaaS, and the rules vary by delivery model. We assess economic-nexus thresholds (post-Wayfair), set up registrations where required, and recommend a sales-tax automation tool sized to your volume.
What's the maximum I can put away into retirement as a solo founder?
With the right stack — Solo 401(k) employee plus employer contributions, mega-backdoor Roth, and optionally a defined-benefit plan layered on top — high-margin solo founders can shelter $70K to over $300K annually depending on age and income. We model and set up the stack, then coordinate with your investment advisor.
I have customers in 30+ states. What about income tax nexus on my LLC?
Different from sales tax — but real. Some states treat economic activity above a threshold as creating an income-tax filing obligation. We map exposure, decide where to register, and use composite or PTET elections where available.
I'm building a venture-track startup. Should I be a C-corp for QSBS?
If you intend to raise institutional capital and the five-year hold is realistic, a Delaware C-corp with QSBS-qualifying stock issued at the right time is one of the most powerful tax structures available — up to 100% federal exclusion on qualified gain. We coordinate with your startup attorney on the structure and track the five-year clock.
Build the structure once. Compound after-tax for a decade.
Fifteen minutes, a clear read on whether your current setup is leaving money on the table, and the next two or three moves that matter most.