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.
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
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1 Oct 2026
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.
28 Sept 2026
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.
Who has been a guest on Laid Off To 8 Figures with David DiNardo
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Graham Barlow
Shauna Tragnam
Gustavo Sanchez
Hugues
Martin DeSouza
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5.0 / 5
12 ratings
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