Laid Off To 8 Figures with David DiNardo

David DiNardo
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Learn how real founders build, scale, and sell businesses in Canada — the raw truth behind the highlight reel. I'm David DiNardo. Laid off from a hospital job, built & sold a 7-figure cloud accounting firm, now building Taxifi, an AI tax platform. Every week: interviews with 7 & 8-figure founders, plus solo deep-dives on AI tools, Canadian taxes, and business strategy. Real operator stories, how to build and exit, and the tools that actually move the needle. New episodes weekly. Hit follow if you want to build something real.

  1. 1d ago

    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.

  2. 6d ago

    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.

  3. Sep 28

    A Year of Cringe Solo Videos Just Landed Me a Client in 15 Minutes

    I couldn't watch a full episode of my own solo videos for the first 50. This morning a client signed up for bookkeeping, accounting and tax on a monthly subscription in under 15 minutes, and he found me through one of my reels after comparing three competitors. A year of organic content did what six months and thousands of dollars of Meta Ads couldn't. In this episode:→ How a reel turned into a signed client before the first call ended→ Why the first year (maybe two) of content will feel like cringe, and why that's fine→ The five-year play, and why I've committed to Taxifi for 10 years minimum→ "It was me against me": what actually changed in how I speak on camera→ Why the people who put themselves out there beat smarter competitors→ Whoever owns distribution owns the moat Powered by Taxifi.

  4. Sep 24

    Alex Lawson: Food Bank Kid to 17 Employees to the Mayor's Race

    Alex Lawson: Ottawa Has 42 Cops on Duty for a Million People — Same as 1995 He grew up on the food bank in Heron Gate. Now he runs a framing company with 17 guys — and he's running for Mayor of Ottawa. Alex Lawson says the city has leaking buckets everywhere, and politicians keep promising to pour more water in. This is the builder's case for fixing the holes first. → Why he voted for the current mayor, and what changed his mind→ "Politics is communication, and business is a series of the right communications"→ Why he wrote his transit policy by talking to bus drivers, not consultants→ What Pet Circus and the Argyle Street landlord told him about downtown→ Alex's numbers: 42 officers on duty minimum, the same as 1995; OC Transpo losing $54M; police unable to investigate fraud under $25K→ The 82-year-old widow the vacant unit tax is pushing toward a food bank→ A $6 sausage in Ottawa vs. $2 in Toronto, and what that says about permits→ The moment he realized he was the bottleneck at Capital Framers→ Scarcity vs. abundance: why he's fine when his guys leave to start their own thing→ Getting called a communist and a fascist in the same week, and riding the wave of hate→ His sticky note: "Keep going" Connect with Alex: votealex.ca — search "Alex Lawson Ottawa" on Instagram, Facebook, X and TikTok. Get in touch with David: search "davidrdinardo" on Instagram and LinkedIn, or visit laidoffto8figures.com. Powered by Taxifi — AI-powered bookkeeping, tax & payroll for incorporated Canadian businesses. Visit taxifi.ai and use code LAIDOFFTO8FIGURES for 1 month FREE. Educational purposes only — not financial, tax, or legal advice.

  5. Sep 21

    I'm 38. Here's Exactly How I Became Successful in 10 Minutes

    I'm 38, and in under ten minutes I'm going to tell you exactly how I got here. No theory. Just the sequence. → Rule 1: surround yourself with the people you want to become. My whole family owned rental properties or started businesses, so that's what I saw. → Rule 2: education. The degree matters less than learning how to learn. → Rule 3: work for someone first. At the Ottawa Hospital I learned what politics is, why a raise doesn't mean you net more, and why hard work alone doesn't get you promoted. → Then I got let go. Best thing that ever happened to me. → Involta: built from zero to 45 employees across Canada, one of the first progressive accounting firms on QuickBooks Online, sold inside ten years, exactly as planned. → The decade nobody talks about: 22 to 32, no kids, no mortgage, up at 5, in bed by 8, six or seven days a week. → Why that decade is what lets me run multiple businesses now with three young boys at home. → Nobody who takes the pledge ever goes back to a 9-to-5. → Trade your value for money, not your time. → I can mentor you 20 or 30%. The other 70% has to come from you. If you're in your 20s and thinking about starting something: scrap everything and put in the reps now. 📬 Get in Touch with David Instagram: @davidrdinardo LinkedIn: search David DiNardo Website: laidoffto8figures.com Email: me@daviddinardo.com 🚀 Powered by Taxifi — AI-powered bookkeeping, tax & payroll for incorporated Canadian businesses. Visit taxifi.ai and use code LAIDOFFTO8FIGURES for 1 month FREE. Educational purposes only — not financial, tax, or legal advice.

  6. Sep 17

    Antonios Assaad: Pro Soccer, a Five-Year Ban, and the Week That Rewired My Life

    Ten years chasing pro football across three continents. A five-year ban at 15. A contract offer from the Prince of Abu Dhabi. Then one phone call, and Antonios Assaad walked away from all of it for a week in Costa Rica. We grew up on the same Ottawa soccer fields. This is the most honest conversation I've had on the show. → The double life behind the athlete: dedicated on the pitch, drinking and partying off it → Banned for five years at 15 for spitting on the ground, and how it shaped everything after → Lebanon, Germany, driving a forklift to afford to keep playing, then coaching at Club América → "I was a terrible teammate": why energy and likability decide who gets picked → The call from Dubai: "When the medicine calls for you, you have to listen" → What ayahuasca actually is, what a week at Rythmia looks like, and why they don't call it a retreat → Rythmia's own numbers: 98.2% of guests report a "miracle" in week one, 92.5% still feel it six months later → From guest to employee: the "download" Antonios turned into a presentation, and a job, the next morning → Scarcity vs. abundance: what happened when he started giving money away → Why he thinks Canada is risk-averse and allergic to big dreams (and why I half agree) → His advice to every Canadian entrepreneur: love your old friends from far away → The sticky note: "Focus on the energy and the vibration, because it will manifest in everything you do" Connect with Antonios Assaad on Instagram: [ANTONIOS IG] 📬 Get in Touch with David Instagram: @davidrdinardo LinkedIn: search David DiNardo Website: laidoffto8figures.com Email: me@daviddinardo.com 🚀 Powered by Taxifi — AI-powered bookkeeping, tax & payroll for incorporated Canadian businesses. Visit taxifi.ai and use code LAIDOFFTO8FIGURES for 1 month FREE. Educational purposes only — not financial, tax, legal, or medical advice. This episode discusses plant medicine and mental health; speak to a licensed professional before making decisions about your own care.

  7. Sep 14

    Stop Hiring Employees. Here's Why I Only Hire Contractors Now

    Employees or contractors? With AI models dropping monthly, it's no longer a payroll question — it's a speed question. In this solo episode I lay out exactly how I'm answering it at Taxifi: contractors only, paid a premium, chosen per project. → Why Ontario labour rules make letting an employee go so hard — and why a contractor can be gone tomorrow → The real cost: contractors run 75–100% more than an employee salary, and you're rarely their only client → The case for employees: SR&ED credits reward payroll, not contracts → When AI handles the technical skills, soft skills become the thing you hire for → Claude Skills: a couple of hours of setup that erased four or five admin hours a month → The "weeks-long" build my developer shipped in three to five hours on a Saturday → Why you have a few years, not a decade, before anyone can click a button and build a product → The one question that wins or loses in this new world: can your staff move at your speed? The old way is not the new way. Rip out the old playbook and have the honest restructuring conversation now. 📬 Get in Touch with David Instagram: @davidrdinardo LinkedIn: search David DiNardo Website: laidoffto8figures.com Email: me@daviddinardo.com 🚀 Powered by Taxifi — AI-powered bookkeeping, tax & payroll for incorporated Canadian businesses. Visit taxifi.ai and use code LAIDOFFTO8FIGURES for 1 month FREE. Educational purposes only — not financial, tax, or legal advice.

  8. Sep 10

    Graham Barlow & Shauna Tragnam: Distribution Is the Only Moat Left

    "AI-powered" on your website now means the same thing as "internet-powered." I changed my own site copy before we finished recording. Graeme Barlow and Shawna Tregunna run FounderLink — 30-plus dinners, close to 2,000 founders across Canada, the US and Europe — and they spend their days watching what actually works across hundreds of companies. This one rewired how I think about mine. → Building is not the moat. You vibe coded it in 72 hours? So can anyone with a cloud subscription. Distribution and attention are the whole game now. → 10/80/10. Human at the front, AI does the work, human checks it before it goes out the door. Customers don't want to hear about the AI — they want to know their money is being spent well and that they can still talk to a person. → Price as high as the market will bear. If they say no, go lower. Old cost-plus pricing is dead because the output is worth multiples of what it used to be. → Solve rich people's problems first. It's easier to work down-market than up. And never sell to the middle — not enough margin to be excellent, not enough volume to be cheap. That's where companies get stuck between $1M and $5M. → The validation playbook: landing page, $20 a day in ads, 500 emails, call every one of them, pre-sell $50K. Then build. If you can't get there, you were aiming at the wrong thing. → Enterprises cancelled every SaaS subscription to vibe code their own tools. A year later they're buying them all back. Restaurants can 3D-print cutlery. They shouldn't. → 200 to 300 cold calls a day for a month. Graham makes early-stage founders do it. "Don't tell me you'd do anything for your kids if you won't get rejected enough to change their future." → Personal brand is Graham's single biggest regret in 20 years. "You're choosing to tie your legs together and roll down the street." → Raise or bootstrap? The bar has never been higher — pre-seed now expects a few hundred thousand in revenue. But a business throwing off $1–3M in profit a year is a phenomenal company, and more people should build one. → Two sticky notes. Shawna: "Think bigger." Graham: "Build personal brand." Graeme and Shawna also came up in my solo episode on the 20/60/20 model — search Laid Off to 8 Figures for that one. 🚀 Powered by Taxifi — AI-powered bookkeeping, tax & payroll for incorporated Canadian businesses. Visit https://taxifi.ai and use code LAIDOFFTO8FIGURES for 1 month FREE. Educational purposes only — not financial, tax, or legal advice.

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Learn how real founders build, scale, and sell businesses in Canada — the raw truth behind the highlight reel. I'm David DiNardo. Laid off from a hospital job, built & sold a 7-figure cloud accounting firm, now building Taxifi, an AI tax platform. Every week: interviews with 7 & 8-figure founders, plus solo deep-dives on AI tools, Canadian taxes, and business strategy. Real operator stories, how to build and exit, and the tools that actually move the needle. New episodes weekly. Hit follow if you want to build something real.

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