Founder Files

It’s essential to understand how bookings, billing, and revenue recognition translate into real financial performance in a subscription-based business, particularly SaaS and AI models. 

I spoke with Suezann Holmes, Founder & CEO of ScaleXP, to break down how SaaS revenue is actually earned over time, why invoicing is one of the most critical data sources in a subscription model, and how core SaaS metrics are built from that data. 

The conversation focuses on the realities founders face as they scale, including revenue timing, common invoicing and reporting mistakes, and what it takes to maintain financial credibility with investors and boards.

If you’re leading a SaaS or subscription-based company and preparing for fundraising or board-level reporting, this episode is especially relevant. You’ll learn how revenue recognition under ASC 606 or IFRS 15 impacts ARR, MRR, retention, and growth metrics, and why getting this wrong early creates compounding risk as the business grows.

(00:00) Introduction

(01:55) A founder’s $5M “revenue” mistake: bookings vs real revenue

(02:22) Why revenue matters: profitability, cash burn, and usage

(03:27) Revenue vs contract value: what you’ve earned vs what’s promised

(05:06) Bookings and contract value as leading indicators

(06:19) Why invoicing is not just a back-office task

(07:17) How to avoid invoicing and revenue recognition mistakes

(09:23) CRM data requirements for clean billing and integrations

(10:00) Internal controls for invoicing, revenue, and AR

(11:32) Investor expectations: metrics founders must know by Series A and B

(13:19) How ScaleXP pulls data from Xero and QuickBooks

(13:42) Automating SaaS metrics with a calculation engine

(15:12) ASC 606 and IFRS 15 explained for SaaS founders

(17:41) Credibility as the most important KPI for founders

If you’re a SaaS or subscription business looking to get revenue recognition right, learn more at cypherfin.com.

An investor-ready financial model shows how a startup turns strategy into numbers. It connects the business model, revenue drivers, costs, assumptions, and cash implications into a clear picture founders and investors can rely on.
The CEO owns the story. This includes the vision for growth, strategic priorities, pricing approach, and hiring plan. The financial model exists to test and support that strategy, not to create it.
The finance team’s role is to bring the strategy to life through numbers. This means turning the vision into assumptions, building forecasts, running scenarios, and showing whether the strategy is financially viable.
There are two primary forecasting approaches. Top-down forecasting starts from market size and market share to define long-term potential. Bottom-up forecasting starts from internal drivers like pricing, conversion rates, sales capacity, and hiring to model near-term execution. Strong models use both.
Assumptions are the foundation of the model. They define how revenue grows, how costs scale, how hiring progresses, and how cash moves. Credible assumptions are grounded in historical data, benchmarks, market research, and operating realities.
For SaaS and AI companies, revenue modeling requires separating bookings, billings, recognized revenue, and cash. These do not occur at the same time. Subscription revenue builds over time through an ARR snowball as new bookings stack on top of existing recurring revenue.
Costs and hiring plans are major drivers of margins and cash usage. Modeling COGS, operating expenses, and headcount timing shows how growth decisions impact profitability and runway.
Once revenue and costs are built, the model produces outputs investors care about. These include financial statements, operational cash flow forecasts, and KPIs that show performance, liquidity, and efficiency.
Scenario planning pressure-tests the model. Base, downside, and upside cases help founders understand risk, identify pressure points, and make informed growth decisions before committing capital.
At Cypher, we help SaaS, AI, and e-commerce companies build investor-ready financial models that turn strategy into clear, defensible numbers.

Fundraising in 2026 is more selective.

Here are the 5 things founders need to get right in 2026:

(00:00) - Introduction

(01:09) - 1️⃣ Be clear about your fundraising strategy and your capital choices

How much do you actually need, and why? Raising too much implies a high valuation. A higher valuation puts you in a tougher competitive set. The real question is whether you can back it up with traction, data, or momentum. Agile fundraising is often the smarter move. You don’t need the full amount on day one. 

(05:07) - 2️⃣ Get investor-ready before you fundraise

Your story and your financial model must align. Assumptions should be defensible and grounded in data. Serious conversations should never start without a clean data room, including your deck, financials, forecasts, cap table, legal docs, team, and operating plans.

(07:07) - 3️⃣ Governance matters more than founders think

Before you raise, model dilution and understand how ownership evolves. Use proper cap table tools like Carta, Pulley, Capbase, or Cake. Review ASC 718 or IFRS 2 early. Equity compensation issues surface fast during diligence. Plan for QSBS eligibility from day one. Governance mistakes destroy leverage.

(08:29) - 4️⃣ AI changed the game

Building software is cheaper and faster than ever. The product alone is no longer the differentiator. Simply “using AI” is not a strategy. Investors care about real usage, real demand, distribution, and the strength of the team executing.

(09:18) - 5️⃣ Don’t stop networking

Fundraising doesn’t start when you need money. Strong networks are built ahead of time. Access still flows through trust, timing, and warm introductions.

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.

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Talk to Cypher⁠⁠⁠⁠⁠

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.

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Talk to Cypher⁠⁠