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What would make you sell your house and put the money into a business you weren’t even sure would work?

For Craig Joel, part of the answer was being naive enough not to fully understand how hard it was going to be.

Craig is the founder and CEO of Now Book It, but his story started long before software.

He bought his first restaurant at 24, learned some brutal lessons about tax, numbers and running a business, then spent years inside hospitality before spotting a problem restaurant owners kept complaining about.

We talk about what happened when he put everything behind Now Book It, the moment COVID shut down virtually his entire customer base just as the company had finally become profitable, and how they went from signing roughly 150–160 restaurants a month pre-COVID to as many as 400–500 in some months afterwards.

Then we get into the part most founders barely think about until it’s happening: selling the business.

We get into:

→ Why Craig believes hospitality, financial and marketing acumen are the three skills that can make or break a hospitality business

→ How listening to restaurant owners complaining about booking fees and losing control of their customer data became the opportunity behind Now Book It

→ The roughly $600,000 initial software build, why Craig sold his house to protect his equity, and why he says knowing what he knows now might have stopped him doing it

→ Going from finally reaching profitability to watching COVID shut down the restaurant industry, then building a takeaway solution in four days

→ How Now Book It jumped from around 150–160 new restaurants a month pre-COVID to 400–500 in some of its biggest months

→ Why AI makes software dramatically easier to build, but relationships, integrations, distribution and customer understanding create the real moat

→ What Craig learned selling Now Book It, including EBITDA, revenue multiples, earnouts and why you need to know your numbers before talking to a buyer

→ Why the highest offer isn’t necessarily the right exit when your team, your role and what happens to the business afterwards actually matter

You can spend years obsessing over how to start and grow a business without ever thinking seriously about how you’ll eventually leave it. Craig has lived both sides, including what happens when the founder sells but isn’t actually ready to walk away.

Chapters:

0:00 Meet Craig Joel, founder of Now Book It
1:00 Selling the house and going all in
3:00 Starting in hospitality at 16
6:00 Buying a restaurant at 24
10:00 The three types of acumen business owners need
14:00 Finding the problem that became Now Book It
17:00 Finally profitable… then COVID hit
22:00 Why human customer service still matters
23:00 The $600,000 build and bootstrapping Now Book It
28:00 AI has changed the cost of building software
33:00 The booking fee problem Craig wanted to fix
38:00 Pricing Now Book It and investing in AI
45:00 What breaks when a business scales
49:00 Selling the business without planning to sell
57:00 Valuations, EBITDA, multiples and preparing to exit
1:00:00 Why Craig stayed after selling
1:16:00 Craig’s advice for founders considering an exit

If you have any questions about the episode, have a burning question you would like me to answer on the show, connect with me and the rest of our incredible community on Instagram:

→ https://www.instagram.com/sammykennedycoach/
→ https://www.instagram.com/sammykennedyofficial

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The difference between debt that grows your business and debt that quietly destroys it often comes down to one thing: whether you actually understand the numbers before you sign.

Cameron Tilley has been our finance broker for almost two decades, which means he’s had a front-row seat to some of the Kennedy family’s more delusional business decisions. He’s also seen businesses across countless industries borrow, expand, refinance, struggle and grow.

We get into the side of business finance most owners only learn once it hurts: why profit doesn’t necessarily mean you have cash, how banks actually assess your business, when debt makes sense, what being overleveraged really looks like and why getting the right advice before you need money can completely change your options.

We get into:

→ Why Cameron believes even a 10% profit margin can be cutting it skinny when things go wrong

→ How a business can report a $400,000 net profit and still end up bankrupt because of cash flow

→ The numbers behind our bowling alley, from almost running out of money during the fit-out to getting finance moving after just nine months of trading

→ Good debt vs bad debt, and why an income-producing asset is very different from buying something because you want it

→ How leverage changes across houses, commercial property, business assets and specialised assets like a bowling alley

→ Why going straight to your bank can limit your options, and Cameron’s explanation of what a finance broker actually does

→ The cash flow system we’re building around weekly breakevens, separate bank accounts, tax, buffers and seasonal revenue

→ Interest rates, refinancing, fixed vs variable debt and why flexibility can matter just as much as getting the lowest rate

If you’re building something ambitious and debt is part of the plan, this conversation will make you think much harder about what you borrow, what you buy and whether your cash flow can actually carry it.

Chapters:

0:00 Meet Cameron Tilley
3:00 The most “delusional” businesses Cameron has financed
5:00 Credit card surcharges and hidden business costs
8:00 How much financial buffer does a business need?
11:00 Building the right professional team around your business
15:00 Profit margins across different industries
20:00 What a finance broker actually does
23:00 When should a business refinance its debt?
26:00 Why profit and cash flow are not the same thing
32:00 Arcade or hospitality venue? Our real expansion dilemma
34:00 How to know when you’re overleveraged
36:00 Good debt vs bad debt
41:00 How banks assess business owners and ABN history
44:00 Finance broker vs going straight to the bank
47:00 Building a better cash flow system
53:00 Using seasonality to plan your marketing and revenue
56:00 What interest rate rises mean for small businesses
59:00 Fixed vs variable debt when you’re still growing
1:01:00 Restructuring, tax changes and protecting your exit
1:08:00 Submarines, planes and Cameron’s strangest finance requests

Got a question about your own business right now? Drop it in the comments, I read every single one.

If you have any questions about the episode, have a burning question you would like me to answer on the show, connect with me and the rest of our incredible community on Instagram:

→ https://www.instagram.com/sammykennedycoach/
→ https://www.instagram.com/sammykennedyofficial

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What actually keeps a business alive when customers are more cautious, cash flow is tighter, and “average” no longer cuts it? The answer isn’t simply more sales.

Five years ago, getting people to spend was easier. In 2026, customers are researching more, comparing harder and asking whether what you sell is genuinely worth their money.

In part two of this series, I’m breaking down what I believe business owners need to focus on now: protecting profit, building cash reserves, fixing unprofitable pricing, improving team productivity, controlling debt, sharpening your positioning and making it ridiculously easy for customers to buy.

We get into:

→ Why knowing your weekly breakeven number changes the way you manage cash flow

→ The $10,000 cash buffer I struggled to build, and why automating savings finally made it happen

→ Why more sales can actually create more problems when your pricing isn’t profitable

→ What 50–60% staff capacity is telling you before you even think about hiring again

→ The danger of overleveraging, including $150,000 purchases that don’t have a clear path to ROI

→ Why lowering your prices when customers say “that’s expensive” can make the problem worse

→ How constant discounts train customers to wait instead of buy

→ Why “average” marketing, service and customer experience are becoming the danger zone in 2026

This is about building a business that can handle pressure without forcing you into reactive decisions, and becoming the business customers deliberately choose when they’re thinking harder about every dollar they spend.

Chapters:

0:00 Why selling is harder in 2026: Part 2
1:45 Why profit has to come first
3:28 Work out your weekly breakeven
6:22 Building cash reserves before you feel ready
8:05 My $10,000 cash buffer
12:13 Reassessing pricing and operating costs
13:50 Fix productivity before hiring more staff
15:16 Turning fixed costs into variable costs
17:38 Debt, overleveraging and $150,000 purchases
20:03 Your brand needs a real point of difference
22:25 How consumer spending has changed since 2021
24:30 Why lowering your prices can backfire
26:12 Discounts can train customers not to buy
28:14 Why average is becoming the danger zone
29:21 Remove friction from the buying process
31:47 Give people something worth talking about

If you have any questions about the episode, have a burning question you would like me to answer on the show, connect with me and the rest of our incredible community on Instagram:

→ https://www.instagram.com/sammykennedycoach/
→ https://www.instagram.com/sammykennedyofficial