Matt Tait’s Post

🎮 StartPlaying is the world’s largest platform connecting players with professional Game Masters. When Gabriella Stark joined as Operations Manager, finance was fully manual: one accountant, year-end financials, and hours spent reconciling Stripe transactions and pulling investor reports. As the company scaled, so did the complexity: Stripe Connect payouts, refunds, disputes, timing gaps, and deferred revenue from prepaid sessions and gift credits. Every month-end felt like something might slip through the cracks. After moving to Truewind, Gabi turned financial chaos into clarity: → 10+ hours saved every month → Month-end close reduced by 4 days → 20% less investor admin time → Audit-ready books every month “Now everything feels structured and predictable. It’s freed us up to focus on analysis and decision-making instead of just keeping up with the close.” For lean teams managing your books alongside everything else this is what it looks like when your back office runs like a system, not a scramble.

Got featured on Stripe’s YouTube while explaining what we do at LedgerUp! I always get asked, “What does LedgerUp actually do?” This is the simple version. Contracts are written in natural language, but billing and finance systems need structured logic. That’s where revenue gets lost and finance gets messy. Someone says “tier 2, 10k seats, 8 cents per seat over 10k, billed quarterly, net 45” and that sentence gets thrown into Slack, Notion, email, a google sheet and brains. In companies, the “translation” is done by humans. AEs, CS leaders, and Ops people like me. That is the gap. LedgerUp lives in Slack. It reads the contract the way a human reads it, then it converts that logic directly into Stripe. Invoices. Subscriptions. Tier updates. Collections. Follow-ups. Straight from contract language to actual cash events without any export or manual middle. Engineers got Cursor, but ops and finance never got their moment, so this is ours.

Lately, I’ve been learning about how much work actually goes into selling software online. Most startups I see simply set up Stripe and move on, which works fine at first. But once you start locking in and selling globally, things like taxes, compliance, and localization get complicated fast. According to The Friction Report by Cleverbridge, 83% of software companies plan to expand internationally, but only 56% feel confident in doing so. That gap says a lot about how tough it is to scale across borders. Learning how the Merchant of Record model helps solve these challenges has been one of the most interesting parts of my job so far. If you’re building something in the software space, let’s connect 👍 #FrictionReport #MerchantOfRecord #B2BEcommerce

When I started Ciphrix, I told myself: “Once I hit this MRR, I’ll relax.” I hit it. Then I moved the goalpost. Then I moved it again. I wasn’t chasing stability. I was chasing the feeling that I was finally doing enough. Here’s what nobody tells you about revenue: it’s not a destination. It’s a loop. → Check Stripe → See money → Feel relief → High fades → Check again It feels productive. It isn’t. It’s just another dopamine cycle wearing a business suit. That’s not freedom. That’s dependency. Then one day I was having a conversation with a friend and he askeed me a question. “Ashish, why did you even start this?” My answer was “I started to build something that genuinely helps people.” That was the dream. That was the point. But somewhere along the way, I reduced asking “Did we help someone today?” and started asking more “Did we hit our number?” That’s when I realized the mission quietly turning into a metric. Look, I'm not saying revenue doesn't matter. It does. Teams need salaries. Growth needs fuel. Bills to be paid. But there’s a difference between running a business and letting a number decide how you feel about yourself. So now I'm learning to ask separate questions: → Is the business doing well? → Am I doing well? → Is my team doing well? Because for too long, I treated them as the same question. And when you do that, you stop building something meaningful and start chasing validation. Many months of refreshing dashboards taught me: → No amount of money will ever make you feel free if you're using it to prove you're enough. → You were already enough. Before the first dollar came in. Before you built anything. Before you had proof. The money is just money. It measures revenue, not worth. Your value was never in the spreadsheet to begin with. P.S. What number are you checking compulsively that's controlling how you feel about yourself?

From time to time, it’s worth checking your workflows. Silent issues can quietly kill growth. Today we noticed Klaviyo and Stripe weren’t syncing properly. Looking into the root cause to fix it. These issues can cost momentum and money.

In 2010, two Irish brothers, Patrick and John Collison, set out to fix one simple problem: getting paid online. At that time, accepting payments was slow and confusing. Developers had to deal with banks, long forms, and outdated systems. Stripe promised to make it easy with just a few lines of code. No one believed them. So the Collisons did something unusual. They visited startups, sat beside the founders, and said, “Open your laptop, let’s get you set up.” They called it the Collison Install. Patrick or John would write the code themselves and make sure it worked before leaving. It was slow, but it revealed the truth. They saw where people got stuck and what didn’t make sense. Each visit made Stripe clearer and faster. They weren’t chasing growth. They were learning how real people used their product. That curiosity became their advantage. By fixing one user’s problem at a time, they built a product that eventually worked for millions. The lesson is simple. Understanding friction is the first step to removing it. Sometimes progress begins by sitting beside one person and watching where they struggle. #innovation #strategy #valuation

Chasing 10k months is the DUMBEST thing struggling founders do. Here are the 6 reasons why obsessing over revenue milestones keeps you broke: 1. I stared at the Stripe dashboard for 5 minutes straight. $10,247 for the month. I kept refreshing, waiting for some euphoric feeling to kick in. Nothing. I felt exactly the same as I did at $3k months. Same person, same thoughts, same daily routine. 2. The money didn't fix a single real problem in my life. I still woke up with the same anxieties. Still had the same relationship issues. Still felt the same imposter syndrome on client calls. The number in my bank account changed, but I remained completely unchanged. 3. I realized I'd been chasing the wrong thing entirely. For months I'd been telling myself "once I hit 10k, everything will be different." But nothing was different because I was still the same person who created the problems in the first place. The money was just a byproduct. 4. Most founders put revenue milestones on pedestals. It's like seeing an attractive person at a bar and putting them on such a high pedestal that you become weird and unnatural around them. Same energy with money goals - the desperation actually repels what you want most. 5. Your mind doesn't upgrade when your bank account does. This is the part nobody talks about. You can make 10k, 50k, even 100k months, but if you haven't done the internal work, you'll sabotage it back down to your comfort zone. I've watched this happen to dozens of founders. The real milestone isn't the money - it's becoming the person who can sustain it. Someone making consistent 10k months thinks differently than someone making 3k months. They have different daily habits, different beliefs about their worth, different standards for their business. The money follows the identity, not the other way around. TAKEAWAY: Stop chasing revenue milestones like they're going to save you. Work on becoming the version of yourself who naturally generates that revenue. Fix your mindset first, then the money becomes inevitable. But please, pretty please, above ALL ELSE... Don't put your goals on pedestals where they become impossible to reach. (Don't forget to sign up to the best newsletter on LinkedIn: oscarhoole.com )

John Collison of Stripe: Ireland is going backwards. Here’s how to get it moving The Stripe cofounder looks at how the State can get out of the government-by-agency corner into which it has painted itself https://lnkd.in/eBGwAAju

John Collison of Stripe: Ireland is going backwards. Here’s how to get it moving The Stripe cofounder looks at how the State can get out of the government-by-agency corner into which it has painted itself https://lnkd.in/eBGwAAju