Founder Files

Payroll is typically 50% or more of expenses, the single biggest spend on the P&L. David Hori , Principal at Topline Operators, joins Founder Files to clarify how payroll, HR, and operations work together in scaling companies, and where they fall apart. (00:00) Introduction (00:38) How can you tell if a payroll setup isn't really a system? (01:36) What is the go-to systems solution you wou...

Accounts receivable is one of the most common sources of cash flow pressure in growth-stage companies. Revenue can look strong on paper, but when collections don’t keep up, cash becomes constrained. In this video, I break down how AR and collections actually work, where they start to break down, and how to fix them. I also cover how to think about bad debt strategically and what it means for your...

What does a fractional CFO actually do, and when does a company need one? Here are the most common questions founders and CEOs ask as their business grows beyond basic accounting. From cash flow management and capital allocation to forecasting, reporting, and decision-making, the role of a CFO is about turning financial data into direction. If your numbers exist but aren’t helping you plan, alloca...

Rows of numbers and clean reporting might make it look like the dashboard is doing its job. But the real question to ask is: “Can leadership look at it and know what to do next?” In this conversation, I sit with Nick Jain to explain what makes a financial dashboard useful, how companies should think about dashboards from day one, and why visual, dynamic, decision-oriented dashboards matter as the...

Clean books and polished dashboards might make it look like the finance function is working. But the real question to ask is: Would leadership make different decisions this week with or without those numbers? In this conversation, I sit with Nick Jain to explain the difference between transactional finance and strategic finance, with a focus on companies growing in the $1M–$30M range. (00:00) Intr...

Stakeholders may request audits when companies are raising capital, bringing on private equity, expanding credit facilities, or entering serious M&A discussions. That is when expectations change. In this conversation with Rawan Sakatan, CPA, Director at Weaver, we discuss why audits appear as companies scale and how investors, lenders, and buyers think about financial reporting. (00:00) Introd...

Carter Looney , Operating Partner at Albatris and M&A advisor with 25+ years of experience, breaks down how a $12M SaaS company with strong margins and over a year of runway nearly ran out of cash. Revenue looked strong. EBITDA was positive. But accounts receivable ballooned, hiring outpaced collections, and timing killed liquidity. Profit doesn’t equal cash, and growth without cash discipline...

Carter Looney⁠ , Operating Partner at Albatris and M&A advisor with 25+ years of experience, explains the real difference between budgeting and forecasting, and why confusing the two leads founders to hire too early, overestimate revenue, and ignore cash timing. Budget is direction. Forecast is reality. Learn why pipeline isn’t revenue, why hiring to plan is dangerous, and why timing of cash m...

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 S...

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...

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 tracti...

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 econom...

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, w...

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 pr...

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 fin...

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 react...

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:...

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 wi...

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 opportunit...

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...

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 v...

Noel-Edouard Chenu , Founder & CEO of Boundless Digital , joins Founder Files to share how a lean, bootstrapped team is scaling in the enterprise world by simplifying Cisco’s complexity. From why outbound sales fell flat to how inbound content and Cisco partnerships drive growth, Ned explains the GTM strategy that actually works for enterprise buyers. He also dives into Boundless’ approach to...

Ben Nowlan , CEO of Sherpa , joins Founder Files to share what a decade building one of Australia’s largest last-mile delivery networks has taught him about focus, financial discipline, and competing with giants like Uber. From avoiding the “early adopter trap” to tripling lifetime value in just four months, Ben reveals how Sherpa scaled without losing its core value proposition — and why founders...

Jon Ricketts , Founder & CEO of EKOM AI , joins us to explore how AI is reshaping the e-commerce stack. From SEO shifts to the rise of autonomous software, Jon shares how EKOM AI helps brands optimize discoverability and reduce manual work. Hosted by ⁠⁠⁠⁠⁠Salma Hatim⁠⁠⁠⁠⁠ , Founder & CEO of ⁠⁠⁠⁠⁠Cypher⁠⁠⁠⁠⁠ . Topics include: – Algorithm updates, AI search, and why product data matters – Wh...

Svitlanka Sergiichuk, Co-founder & CEO at Neofin , joins Founder Files to share how they built a global lending platform without venture capital. Instead of raising early, Neofin scaled with revenue, partnerships, and process. Hear how Neofin uses LLMs to streamline underwriting, localizes in 3 days, and sells to multi-country lending groups, all while staying lean. Hosted by ⁠⁠⁠⁠Salma Hatim⁠⁠...