Somewhere between "I built this" and "I sold this" is a decade of decisions most founders get wrong. This is the show about those decisions.
Worth Owning is the podcast that takes you inside the build and the deal. Scale stories from founders who turned owner-operated companies into assets. Exit stories from the ones who sold, and what they'd do differently. Deal room insights from the bankers, private equity buyers, and M&A advisors on the other side of the table.
You'll hear from both sides. The founder who built it. The buyer who acquired it. And the uncomfortable truth about what actually makes a business valuable, transferable, and ready.
Hosted by Krystyn and Matt Harrison, cofounders of Horizon Advisors, an advisory platform for owner-operators that pairs you with advisors who've built, scaled, and exited themselves. Horizon's advisors have had front row seats to over $1B in enterprise value. Now we're bringing the playbook to owner-operators building between $3M and $100M+ in revenue.
If you want to know what makes the difference between a company that sells and one that stalls on the market, this is your show.
Worth Owning covers M&A, founder exits, growth strategy, deal structure, valuation, operator psychology, and what it really takes to go from running the business to owning an asset.
Because the work you do to make your business worth buying is the same work that makes it worth running.
New episodes every week. Subscribe so you don't miss one.
Your Business Isn’t Ready for AI (Here’s How to Fix It) | Jon Black & Ariel Lobo, Aurora Designs
Most owners use AI as a faster typewriter. A few are building a team underneath their best people.
Jon Black and Ariel Lobo are co-founders of Aurora Designs, a Toronto firm that builds AI systems inside small and mid-sized businesses. For one client, they took a 45-minute onboarding task down to under a minute. The AI cost about two cents a run.
We go back to the basics: AI employees 101. Jon and Ariel explain the difference between an automation and an agent in plain English. They also explain why AI can't fix a broken process. It multiplies whatever is already there. A support team with no playbook gets a chatbot with no playbook.
Then we get practical. What an org chart looks like when part of the team is digital. The five levels of AI adoption, and where I score myself (level 3, and not where I want to be). Why every AI needs a shared "company bible" to work from. And the trap of using AI to start ten projects at once.
Here's the part owners miss. The work that gets your business ready for AI is the same work that makes it sellable. Get the knowledge out of your head and into playbooks, and buyers pay for it.
In this episode:
- Automation vs. agents, and when a person needs to check the output
- How Aurora cut a 45-minute client onboarding task to under a minute
- The five levels of AI adoption, from "search engine" to "it runs, I review"
- The one thing to do Monday: track where your time goes, the way you track cash
Chapters:
00:00 Cold open
00:46 Most owners use AI as a faster typewriter
03:15 AI multiplies what's already there
04:55 Automation vs. agents, in plain English
05:54 45 minutes to under a minute, for 2 cents
07:40 The "sandwich": keeping a person in the loop
09:23 Why less context makes agents better
12:03 An org chart with digital employees
14:57 The 5 levels of AI adoption
17:45 The company bible
18:24 Getting AI-ready makes you sellable
20:55 Why small businesses have the edge right now
22:14 Demo: an AI operating system for one team
26:13 Level 5: building your own tools
30:20 $242K to $1.3M with AI in the back office
31:10 What stops owners from starting
33:23 My own score: level 3
34:33 10x as powerful, or 10x as thin
36:05 Track your time like you track cash
38:00 The one thing to do Monday
39:46 Where to find Aurora Designs
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Jon Black and Ariel Lobo are co-founders of Aurora Designs, a Toronto firm that builds AI systems inside small and mid-sized businesses.
Check out Aurora Designs: https://aurora-designs.ca (https://aurora-designs.ca)
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Connect with Krystyn: https://www.linkedin.com/in/krystynharrison/ (https://www.linkedin.com/in/krystynharrison/)
Or book an intro call at Horizon Advisors: https://withhorizon.co (https://withhorizon.co)
Subscribe for new episodes every week.
General information only. Not financial, legal, tax or investment advice.
30 Apr 2026
Why Most CFOs Can't Survive Diligence (And Why 75% Of M&A Deals Die) | Susan Richards, Numbercrunch
In this conversation, we get into the specific moves every founder needs to start making 36 months before a sale. We break down normalized EBITDA, and the add-back game buyers play in diligence. We get into fully-loaded CAC, unit economics by channel, and the Grow–Ramp–Scale framework for knowing when to level up your finance function. And we get into why 75% of M&A deals fall apart - and why the ones that close almost always share the same 36-month prep story.
What you'll learn:
00:00 - The million-dollar decisions founders make on gut feel and bank balance
00:54 - Hot take: most CFOs are controllers with a bigger title
02:15 - Three questions to tell if you have a real CFO or just a controller
03:33 - "I can't predict the future" — why that answer is a red flag
04:46 - When month-end financials should actually hit your desk (and why the three-day close is a lie)
05:50 - The "so what?" test for every financial report you receive
08:45 - Capital allocation: funding your growth divisions vs. propping up the laggards
09:13 - Why cash in the bank is the worst decision-making tool a founder can use
11:06 - How revenue complexity dictates the CFO skill level you actually need
12:46 - EBITDA in plain language (and why every lender treats it as profit)
13:40 - Normalized EBITDA explained: the add-backs every private business owner should document now
16:10 - The buyer arbitrage play on unnormalized EBITDA — and how to neutralize it
18:07 - Why time kills all deals and what a 36-month prep window actually looks like
18:38 - The founder, CMO, and CFO sitting at the same table — and why most conversations break down
21:31 - How a strategic CFO partners with growth instead of blocking it
23:26 - Fully-loaded CAC vs. vanity CAC, and why the number alone means nothing
25:43 - When to start segmenting CAC by channel, ICP, and trailing twelve months
27:30 - Grow, Ramp, Scale — the finance shift each phase demands
30:24 - The real cost of launching outbound as a brand-new channel
33:10 - Starting exit prep 36 months out: the first moves every founder should make
33:39 - What separates a clean diligence from a deal that falls apart mid-process
37:20 - The exit prep checklist to start on tomorrow morning
38:47 - Enterprise value in plain language — and why your current financials don't show it
40:40 - Strategic vs. financial buyers, and why every founder should court both
41:35 - Why 75% of M&A deals fall apart (and what the other 25% have in common)
42:38 - Where to find Susan
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Susan Richards is a CFO and cofounder of Numbercrunch, a fractional finance function that supports growing companies from startup through exit.
Follow Susan: https://www.linkedin.com/in/susan-richards-fcpa-fcma-53b2176/ (https://www.linkedin.com/in/susan-richards-fcpa-fcma-53b2176/)
Check out Numbercrunch: https://numbercrunch.ca (https://numbercrunch.ca)
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Connect with Krystyn: https://www.linkedin.com/in/krystynharrison/ (https://www.linkedin.com/in/krystynharrison/)
Or book an intro call at Horizon Advisors: https://withhorizon.co (https://withhorizon.co)
Subscribe for new episodes every week.
21 Apr 2026
Horizon LIVE: How to Sell Your Profitable Business | Jackie Dinsmore & Brent Holliday
Most founders build profitable businesses. Very few build sellable ones. There's a massive difference, and it could cost you millions.
In this first live recording of Inside M&A: Opening the Playbook, Krystyn Harrison (Co-Founder & CEO, Horizon Advisors) sits down with Jackie Dinsmore (Managing Partner, Caravel Law, 3x exited founder) and Brent Holliday (Founder & CEO, Garibaldi Capital Advisors) to break down what actually makes a business sellable, how valuations really work, what kills deals, and the exit timeline math every founder should know.
Whether you're exploring your options or actively working toward an exit, this session gives you the insider playbook, straight from people who've been on every side of the table.
Want to be in the room live at the next Inside M&A? Subscribe to the series → https://luma.com/horizonadvisors (https://luma.com/horizonadvisors)
WHAT YOU'LL LEARN
- 0:00 – Why this conversation matters right now, and who's in the room
- 2:45 – How to tell if your business is actually sellable (not just profitable)
- 6:30 – How to "stage" your business for a buyer the way you'd stage a home for sale
- 9:15 – The deal-killing blind spots most owners don't see until it's too late
- 14:00 – The exact things to say (and never say) when a buyer calls out of the blue
- 18:30 – How EBITDA normalizations work in plain English, and why they can add millions
- 22:00 – How adjusting your owner salary can add millions to your valuation
- 25:00 – Who to tell about a potential sale, when to tell them, and how much to share
- 28:30 – The real exit timeline: how long a sale actually takes from first call to close
- 31:00 – How to know when NOT to sell your business
- 34:30 – Why hitting $5M in revenue unlocks 65% more of the buyer market
- 37:00 – Rapid-fire: the biggest green flags, red flags, and the one question founders never ask a buyer
- 40:00 – The single sentence that separates owners who get great exits from those who don't
—
Jackie Dinsmore— Managing Partner of Caravel Law. 3x exited founder. Successfully sold a consumer products company and two professional services firms. Now leads 120+ lawyers across Canada and is disrupting how legal services are delivered to entrepreneurs.
Follow Jackie: https://www.linkedin.com/in/jacqueline-dinsmore-3a11a55/ (https://www.linkedin.com/in/jacqueline-dinsmore-3a11a55/)
Check out Caravel Law: https://www.caravellaw.com (https://www.caravellaw.com)
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Brent Holliday - Founder & CEO of Garibaldi Capital Advisors, Canada's first tech-focused M&A advisory firm, founded in 2013. 30+ years in tech and finance. Former venture capitalist. Now advises entrepreneur-owned tech companies on exits, with a team of 8 across Vancouver, Toronto, and the San Francisco Bay Area.
Follow Brent - https://www.linkedin.com/in/brentholliday/ (https://www.linkedin.com/in/brentholliday/)
Check out Garibaldi Capital: https://garibaldicapital.carrd.co/ (https://garibaldicapital.carrd.co/)
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Connect with Krystyn: https://www.linkedin.com/in/krystynharrison/ (https://www.linkedin.com/in/krystynharrison/)
Or book an initial call at Horizon Advisors: https://withhorizon.co (https://withhorizon.co)
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