Laid Off To 8 Figures with David DiNardo

David DiNardo
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The raw truth behind the highlight reel. Real founders on how they actually built, scaled and sold their businesses — the layoff, the first dollar, the first hire, the month it nearly fell apart. I'm David DiNardo. Laid off from a hospital job, I went all in on Envolta, a cloud accounting firm, grew it to 45 people across Canada and sold it ten years later. Now I'm building Taxifi, an AI ledger for small businesses, in public. New episodes weekly: founder interviews plus solo deep-dives on AI, Canadian taxes and running a company. Ottawa-made, Canada-wide.

  1. 6d ago

    Craig Gauthier: Every Rule You Follow Is Optional

    Craig Gauthier has worked in 33 countries, spent five years as a professor, walked out of a hospital job where everyone was counting down to a pension, and now advises companies on strategy and speaks on stages around the world. His #1 international bestseller Rules Optional starts with one question: which rules are you following that no longer serve you? We get into why trust and attention are the two scarcest resources today, the fleas-in-a-jar conditioning that keeps people in a 9-to-5 nobody chose, and why he thinks plumbers will out-earn lawyers as AI eats knowledge work. Then Craig runs his Break, Build, Become framework on me: getting laid off in 2014, refusing to go back to a salary, building and selling two accounting firms, and starting over with Taxifi. In this episode: • What freedom actually means: agency and choice • The two scarcest resources on earth: trust and attention • Fleas in a jar: who made 9 to 5 a rule? • $150K as an employee vs. $150K as an owner • Plumbers will out-earn lawyers • The Matrix: online gets cheap, real life gets expensive • Break, Build, Become: Craig runs his framework on David • The one skill you have to learn: sales • Why your "authentic self" is a myth • Find your North Star and remove the noise Connect with Craig Website: https://craiggauthier.com Rules Optional (free chapter 1): https://craiggauthier.com/book/ LinkedIn: https://linkedin.com/in/craiggauthier Instagram: https://www.instagram.com/goatc11/ Get in touch with David Instagram: https://www.instagram.com/davidrdinardo LinkedIn: https://www.linkedin.com/in/davidrdinardo Website: https://laidoffto8figures.com Email: me@daviddinardo.com Powered by Taxifi, AI-powered bookkeeping, tax and payroll for incorporated Canadian businesses. Visit https://taxifi.ai and use code LOWTO8FIGURES for 1 month free. This content is for general information only and is not financial, tax or legal advice.

  2. Oct 23

    James Nguyen: How I Raised $25M With Zero VCs

    James Nguyen was my banker at RBC. Now he runs Quantropi, a quantum security company in Ottawa that raised over $25 million US with no VCs. Just angels. Just people who trusted him. He told me nobody drops millions on a phone call. You spend ten years earning that call. That hit home. I got laid off in 2014 and built two seven-figure firms the slow way. James explains why reputation is the real fundraise, how a banker with zero physics background got his name on a quantum patent, and why he's staying in Canada to build it. In this episode: → Why nobody drops millions on a phone call, and what actually earned the $25M → $5M in grants, $20M+ from angels, zero institutional VCs → The entrepreneur's job: recognize the problem, filter the noise, execute, hire smarter → You only need one connected person to start a network → The call from Jeff York that pulled him out of RBC → Locked in a room with a whiteboard until the patent cracked → Quantum explained with Where's Waldo in a million-room hotel → Canadian money is slow, US money is fast, and why he's building here anyway → Confidence comes from making the do-or-die call and not dying → His sticky-note advice: get your loved ones on board first Connect with James: search Quantropi, or @jnfinder on Instagram. 🚀 Powered by Taxifi — AI-powered bookkeeping, tax & payroll for incorporated Canadian businesses. Visit taxifi.ai and use code LAIDOFFTO8FIGURES for 1 month FREE. This content is for general information only and is not financial, tax or legal advice.

  3. Oct 20

    How to Sell Any Service: My Exact Sales Process in Under 10 Minutes

    Two calls. On the first one you shut up and listen. On the second one you give three prices, never one. That's the whole system — and it closed nearly every client who walked into my accounting firms. This is the exact sales process I used for years and still run at taxifi today. It works for accounting, law, consulting, trades, subscription pricing — any service you sell to a business owner. In this episode: → The discovery call: 80% listening, 20% talking, and why you lose the client the moment you start pitching → The three questions that uncover the real pain point → Why you never give a price on call one — and how to book the proposal call within seven days → Removing every friction point so the quote comes together fast → Call two: the roles flip, you do 80% of the talking, under 20 minutes → Bronze, silver, gold: how to space the three tiers so everyone picks the middle → The fast-action kicker that gets the signature before the end of the week → The $99 mistake I made on taxifi's own pricing — and what I changed it to Want the Instagram version? Search David DiNardo on Instagram and comment EPISODE on any post. 🚀 Powered by Taxifi — AI-powered bookkeeping, tax & payroll for incorporated Canadian businesses. Visit taxifi.ai and use code LAIDOFFTO8FIGURES for 1 month FREE. This content is for general information only and is not financial, tax or legal advice.

  4. Oct 15

    Brian Claire: He Built a Payroll App Prototype in 10 Minutes

    Brian Claire runs Blueprint Accounting, a seven-person firm in Ottawa, and got tired of payroll tools built for one business at a time. He summarized a Slack thread in Claude, pasted it into Cursor, and had a working prototype in ten minutes. Six months later he had paying clients. Now he’s COO of Nooma, a payroll and HR platform for accounting firms, with a CEO, a CTO, and a funding round underway. In this episode:→ From psychology degree to accountant to tech founder→ The 10-minute prototype, and the two years of tinkering that made it possible→ Surveying 60 firms and finding they each run five to six payroll platforms→ Launching to 40 people with a live glitch→ How a non-developer manages a dev agency and when to trust them→ Shareholder agreements, vesting, cliffs and getting your own lawyer→ Pricing when your software replaces 80% of a payroll person→ Why Intuit is already selling services inside your clients’ QuickBooks→ “Discipline over motivation” Find Brian on LinkedIn and Nooma at noomahq.com. Search Blueprint Accounting in Ottawa. Powered by Taxifi.

  5. Oct 13

    Result as a Service: How I’m Building Taxifi to Be AI Native

    A Taxifi update I haven’t done in months. We moved to monthly bookkeeping clients, built an AI chat that answers any question about your books in real time, and now VCs are looking at us at a stage I didn’t expect. Every feature has to pass two tests: is it AI native, and does it deliver a result? In this episode:→ Why documenting the journey has been one of the best things for the business→ Monthly recurring clients instead of annual sole proprietors→ The AI chat, and the client who went from red to green in three months→ Software as a service is over. Result as a service is what I’m building→ Marketing is the moat, so I spend one to two hours every morning on content→ Doing SEO in-house for full control and speed→ The 10/80/10 model: human, AI, human→ Version 2 launches at the beginning of November Powered by Taxifi.

  6. Oct 8

    Sergey Poltev: Your AI Is Only as Secure as Your Password

    Sergey Poltev grew up studying cybersecurity in Russia and built his career on the other side of it, keeping small businesses safe from hackers. He runs a managed IT, AI and cybersecurity company for the 10-to-50-employee businesses he calls the "hacker sweet spot," and wrote Hack Proof: A Guide to Cybersecurity for Your Business. Three out of four cyberattacks are now AI-related, and most owners have no idea what tools their staff are pasting client data into. In this episode:→ Simplify, Secure, Scale: the 3S model he runs every client through→ Shadow AI: finding out which tools your employees are actually using→ Why your cyber insurance may not pay, and the $47 non-compliance fee that voids it→ Phishing simulations, password managers and the Chrome mistake everyone makes→ Ransomware cloud: when your entire Outlook gets encrypted→ It takes 200 days on average to detect a breach→ Technical debt and what it does to your company's valuation→ Human in the loop: why an agent should never pay an invoice without you→ The AI flash team every business needs: coder, process mapper, data analyst Find Sergey on LinkedIn at linkedin.com/in/sergeypoltev. Powered by Taxifi.

  7. Oct 6

    The 4-Question Meeting I Stole From the Military

    My team at Taxifi just ran our first After Action Review, a military practice for breaking down what happened so the next one goes better. Four questions, one facilitator, no blame, and 40% of the meeting saved for "what will we do differently." I share my notes and real examples from our review so you can run one with your own team this month. In this episode:→ The four AAR questions and how long to spend on each→ Why you need a facilitator and a 90-minute cap→ Why a bookkeeper, an accountant and a developer see the same month differently→ Our real examples: AI categorization, the ideal client we never defined, five clients instead of fifteen→ Why the last question gets 40% of the time→ Bottom-up accountability: the team builds next month's plan, not you→ Keep it to 7–15 people and do it every month Powered by Taxifi.

  8. Oct 1

    Christine Song: Founders Are Lonelier Than Anyone Admits

    Christine Song spent 20 years in HR, the last 10 as the right hand to startup founders. She worked every weekend, answered Slack in the Disney World line, watched three of her founders get removed by the boards that funded them, and never got the exit. So she burned the boats and launched 5to9 Society, a vetted, confidential dinner community for founders and operating leaders, now 60 members across Toronto, Montreal, Ottawa and Vancouver. In this episode:→ What founders actually say behind closed doors, and why they can't say it to their team, their board or their spouse→ Why your executives won't tell you the truth (you can fire them) and a peer across the table will→ Reference-checking every member with their former CEO, and why CEOs never give fake references→ How 10 years of posting the unglamorous side of HR on LinkedIn meant she never applied for a job again→ The "satisfactory" performance review that pushed her out of corporate→ Why there are more founders on TikTok than on LinkedIn→ AI bots, fake outreach, and the room where every hand went down→ Why she gives herself 10 years before judging whether this worked Find Christine and 5to9 Society at 5to9society.com and on Instagram @5to9society. Powered by Taxifi.

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About

The raw truth behind the highlight reel. Real founders on how they actually built, scaled and sold their businesses — the layoff, the first dollar, the first hire, the month it nearly fell apart. I'm David DiNardo. Laid off from a hospital job, I went all in on Envolta, a cloud accounting firm, grew it to 45 people across Canada and sold it ten years later. Now I'm building Taxifi, an AI ledger for small businesses, in public. New episodes weekly: founder interviews plus solo deep-dives on AI, Canadian taxes and running a company. Ottawa-made, Canada-wide.

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