Sales tax is often overlooked by SaaS, AI, and e-commerce companies until it becomes urgent, expensive, and unavoidable.

In this episode of the Founder Files podcast, Salma Hatim sits down with Monika Miles, President of Miles Consulting Group, to break down how sales tax actually works today for modern SaaS businesses.

They cover what nexus really means, the difference between physical and economic nexus, why SaaS is often taxable even when teams assume it is exempt, how contract language can change tax outcomes, and where sales tax software helps and falls short.

The conversation also explains why sales tax issues tend to surface during fundraising, audits, loans, and M&A, and what leadership teams can do to address risk before it becomes a blocker.

(00:00) Introduction

(02:08) What Nexus Really Means Today

(06:58) Are Your Products or Services Taxable

(09:47) Why Automation Alone Isn’t Enough for Sales Tax

(15:28) How to Start the Sales Tax Conversation as a Company

(19:51) Sales Tax Considerations Before a Fundraise or VC Round

(23:02) Knowing When Sales Tax Is and Isn’t a Priority Yet

(26:10) What an Initial Call with Miles Consulting Group Looks Like

(30:48) Why Sales Tax Should Be a Leadership Priority Before Diligence

💡 New episodes drop every Tuesday at 7 AM EST.

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Learn more about ⁠⁠⁠Cypher⁠⁠⁠.

Tech-Enabled Accounting & Finance. Built for Growth.

Meet Andrew Ackerman, 2x founder, VC investor with 70+ early-stage investments, accelerator operator, and author of The Entrepreneur’s Odyssey.

We sit down with Andrew to unpack what actually drives startup success, from early traction to scaling past the first million in revenue. Drawing on decades of operating, investing, and mentoring founders, Andrew shares a clear-eyed view of what works, what fails, and why.

Topics covered:

• How investors define growth and traction at each stage

• Why most startups fail and what failure really means

• Business vs. venture-scale startup thinking

• Why founders get stuck around $1M in revenue

• What scalable go-to-market really looks like

• Fundraising in tough markets and how to approach it

• When financials need to be cleaned up and why it matters

• Early hires and fractional roles founders should not delay

We also dive into Andrew’s book, The Entrepreneur’s Odyssey: A Novel Approach to Startup Success, a story-driven guide that pulls together real startup lessons into one practical, readable framework for founders.

More about Andrew:

• Buy The Entrepreneur’s Odyssey on Amazon
  

• Visit Andrew’s personal site
  

• Connect with Andrew on LinkedIn

Cash accounting shows what’s in the bank. That works early, when transactions are simple, and the main concern is liquidity.

As companies grow, revenue becomes recurring, hiring accelerates, and financials start driving real decisions. Accrual accounting changes how revenue and expenses are recognized and gives a clearer view of performance. It introduces deferred revenue, prepaid expenses, and proper expense matching. But accrual alone does not mean GAAP-compliant.

(00:00) Introduction
(03:39) The Difference Between Cash and Accrual Accounting
(07:11) When Cash Accounting Still Works (Sole Proprietors and Simple Businesses)
(07:40) Pros and Cons of Accrual Accounting
(10:55) How Accrual Changes Revenue Recognition
(13:09) Top 3 ASC Guidelines AI Companies Should Know for US GAAP Compliance
(17:11) The Biggest GAAP Challenge for SaaS and AI Companies: Revenue Recognition
(24:00) US GAAP Resources for Founders (Guidance + Compliance Checklist)
(25:15) Why Inaccurate Reporting Breaks SaaS Metrics and Decision-Making
(28:12) Why Accrual Alone Is Not Enough and When US GAAP Becomes Critical
(32:14) Final Takeaways and Closing Thoughts

Cash stops working once growth adds complexity. Accrual fixes performance visibility, but without GAAP discipline, gaps still surface. 

Confusion between bookings, invoices, cash received, and recognized revenue is one of the most common issues during fundraising, audits, lending, and M&A. 

SaaS and AI-specific GAAP topics like revenue recognition, software cost capitalization, and diligence questions from investors come up repeatedly.

If your company is growing toward fundraising, an exit, institutional lending, or audits, this helps clarify whether your financials support those goals.

Want a copy of our US GAAP resources?

We have two practical guides we reference often:

• US GAAP compliance checklist for growing companies

• ASC guidance applicable to SaaS and AI businesses

Email [email protected] and I’ll share them with you.

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Talk to Cypher⁠⁠⁠⁠

Learn more about ⁠⁠Cypher⁠⁠.

Tech-Enabled Accounting & Finance. Built for Growth.

Tax issues can come from filing mistakes, but they also come from missing financial context.

In Part 2 of this conversation, I continue my discussion with Bayaan Oluyadi, CPA and founder of KTB Services, focusing on what happens AFTER compliance, and why growing companies often need more than a tax advisor alone as they scale.

We talk through how founders and CEOs should think about fractional finance teams, projections, clean books, and the collaboration required to avoid surprises and missed opportunities when closing out the year.

We cover:

• Why clean, up to date books matter more than most founders realize

• How CPAs, CFOs, and bookkeepers work together effectively

• When a fractional CFO makes sense for growing companies

• Why projections change tax and planning conversations

• Common write-off misconceptions and audit risk

• What real year-close readiness looks like for scaling companies

(01:24) Entity structure as the first lever to avoid overpaying

(03:56) Why clean books drive better tax outcomes

(04:30) Write off myths, audit risk, and the dog story

(06:34) The role of a tax advisor and why collaboration matters

(06:59) Why fractional finance teams exist

(09:13) When a fractional CFO becomes necessary

(12:24) Education, scope clarity, and finance roles

(16:11) Year-close planning tips

Want a copy of our Year-End Financial Checklists?

Email [email protected] and we’ll share it with you.

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Talk to Cypher⁠⁠⁠

Learn more about ⁠Cypher⁠.

Tech-Enabled Accounting & Finance. Built for Growth.

Tax season doesn’t create problems, but it reveals them.

In Part 1 of this conversation, I sit down with Bayaan Oluyadi, CPA and founder of KTB Services, to talk through the questions founders and CEOs ask every year right before tax season and usually too late.

We cover:

• How to think about entity structure and why “I’m an LLC” isn’t an answer

• The tax mistakes that happen when finance is reactive instead of planned

• R&D credits and Section 174 and where companies get tripped up

• Sales tax, nexus, and why this becomes a problem during diligence

• What year-end planning should actually look like for growth-stage companies

Part 2 goes deeper into the role of the CFO, fractional finance teams, and how to build the right finance function as you scale.

Want a copy of the Year-End Financial Checklist?

Email [email protected] and we’ll share it with you.

(02:13) Entity structure confusion

(03:17) Why a CPA alone isn’t enough

(05:18) QSBS and planning from day one

(06:52) R&D and Section 174 pitfalls

(09:38) Why sales tax breaks deals

(11:58) When an LLC should consider S-Corp status

(17:17) What year-end planning should look like

We’re the outsourced finance function for SaaS, tech, AI, and e-commerce companies that want clarity, scalability, and an embedded partner, not just bookkeeping.

If you’re ready to move from chaos to clean books, visit cypherfin.com or ⁠book a call⁠.

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Talk to Cypher⁠⁠

Learn more about Cypher.

Tech-Enabled Accounting & Finance. Built for Growth.

If you’re a founder or CEO carrying a lot of year-end stress, you’re not alone… messy numbers, pressure from investors, and the feeling that your financials aren’t telling the full story.

In our first solo episode of Founder Files, Cypher Founder & CEO Salma Hatim breaks down the real reason so many companies struggle with their financials, and the exact steps to go from chaos to clarity.

(03:18) Clean Up the Historical Financials
(07:46) Streamline Processes
(08:10) Accounts Payable (AP)
(11:00) Accounts Receivable (AR)
(12:59) Payroll
(13:35) Internal Controls
(14:32) Implement Monthly Closes
(17:30) Tax Advisor ≠ Finance Team

We cover:

- Why messy historical books block fundraising & investor trust - The non-negotiable first step: cleaning up prior-year financials - How to rebuild your Chart of Accounts for SaaS, e-commerce & tech

- Revenue recognition (ASC 606), COGS, and margin accuracy - Streamlining AP, AR, payroll & monthly close

- Why your CPA ≠ your finance department

- What founders risk when they mix personal & business spending

- The difference between cash basis vs. US GAAP

- How clean books unlock confident decisions, faster collections & real cash flow visibility

If you're heading into 2026 with blurry numbers, late reporting, or pressure from investors, this episode will show you exactly where to start.

To keep this practical, we’re happy to share the same templates we reference in this episode.

If you’d like a copy of these resources, email [email protected] or connect with Salma on LinkedIn and send a quick message.

1. SaaS Chart of Accounts + FS Templates

2. Pre-Approved Vendor List Template

3. Customer Master Data Template

Cypher delivers Tech-Enabled Accounting & Finance. Built for Growth.

We’re the outsourced finance function for SaaS, tech, AI, and e-commerce companies that want clarity, scalability, and an embedded partner, not just bookkeeping.

If you’re ready to move from chaos to clean books, visit cypherfin.com or book a call.

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Talk to Cypher⁠⁠

Jared Yaman⁠, Co-founder of ⁠Spresso.AI⁠, joins Founder Files to shares his journey from corporate lawyer to gaming entrepreneur, to scaling Boxed.com through IPO, and now to building AI SaaS.

Along the way, Jared dives into capital efficiency, fundraising strategy, and why curiosity and continuous learning matter most as a founder.

Topics include:

— Turning static prices into dynamic ranges with reinforcement learning

— Fundraising advice: when to start, how to prep, and learning from “no”

— Lessons from scaling Boxed.com and competing with Amazon

— The shift from growth-at-all-costs to capital-efficient startups

💡 New episodes drop every Tuesday at 7 AM EST.

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What does it take to build and scale SaaS in one of the toughest industries to break into — healthcare?

Sarah Worthy, CEO & Founder of DoorSpace, shares her journey from enterprise tech into healthcare HR, where she saw a massive opportunity to modernize licensing, credentialing, and continuing education for clinicians.

Topics include:

– Why inspiration alone isn’t enough — market opportunity is everything

– The biggest mistakes founders make trying to scale too early

– How to measure what matters (and what not to obsess over)

– The truth about AI hype and why data ops matter more

– How to sell SaaS into slow-moving, regulated industries like healthcare

💡 New episodes drop every Tuesday at 7 AM EST.

Jess Reagan, Co-Founder & CRO at Paiv, went from leading $200M in solar sales to building a sales enablement platform for the trades.

He opens up about moving from corporate to startup life, why founder-led sales matters, and how fractional CFOs shaped Paiv’s fundraising story.

Hosted by ⁠⁠⁠⁠⁠⁠⁠⁠Salma Hatim⁠⁠⁠⁠⁠⁠⁠⁠, Founder & CEO of ⁠⁠⁠⁠⁠⁠⁠⁠Cypher⁠⁠⁠⁠⁠⁠⁠⁠.

Topics include:

— Founder-led sales vs. hiring early

— Why grit and soft skills beat résumés

— Using fractional CFOs to raise capital

— Building for underserved industries like roofing and pest control

— Balancing family life with the founder journey

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠⁠⁠⁠⁠⁠Talk to Cypher⁠

Sergey Sundukovskiy, Ph.D., Co-founder, CTO & CPO of Salesmsg, shares how a mid-market texting platform scaled from a handful of employees to 75 across 12 countries — while pioneering AI in customer communication.

From generative AI that drafts messages to voice cloning and sentiment analysis, Salesmsg “textizes” entire businesses.

Lessons on building remote-first teams, balancing product vs. tech as a founder, and defining success in SaaS.

Hosted by ⁠⁠⁠⁠⁠⁠⁠Salma Hatim⁠⁠⁠⁠⁠⁠⁠, Founder & CEO of ⁠⁠⁠⁠⁠⁠⁠Cypher⁠⁠⁠⁠⁠⁠⁠.

Topics include

— Using AI for generative messaging, sentiment, and voice cloning

— Building remote-first teams across time zones and cultures

— Scaling from 2 to 75 employees in five years

— Why mid-market businesses are the sweet spot for SaaS growth

— The future of SMS vs. RCS in business communication

💡 New episodes drop every Tuesday at 7 AM EST.

⁠⁠⁠⁠⁠⁠⁠⁠Talk to Cypher