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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

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Business has never been easier to start. So why does it feel so much harder to actually sell?

In part one of this two part series, I'm breaking down what's actually changed in the Australian economy over the past five years, and why so many businesses are getting caught out. I also get personal about my own family's history with debt, because I've lived through exactly the kind of over-leveraging I'm warning you about, twice.

We get into:
→ How the COVID savings boom created a false sense of security for businesses
→ What happened to the household savings rate, and why it matters for you
→ Australia's debt problem, and what it actually means for small business owners
→ The real case study of Stax, and how a $30 million business ended up $23.7 million in debt
→ My own family's story, from a $800,000 failed business to $3 million in debt today
→ Why Betts closed 20 stores after 134 years in business
→ How consumer behaviour has fundamentally shifted, and what that means for your marketing

If you've felt like the rules changed and nobody told you, this episode is that explanation.

Chapters:
0:00 Cold open
1:07 Why business feels harder than five years ago
3:19 What I'm covering in this episode
4:12 The COVID savings boom explained
6:03 How the household savings rate collapsed
8:00 Australia's $1 trillion debt problem
10:07 What Commonwealth Bank's spending data shows
12:00 Why people are craving real connection again
13:38 How buyer psychology has changed
14:42 ANZ's new property price forecast
15:15 A real decision we made about our own debt
18:38 The Stax case study begins
20:34 No one cares about your struggle
21:25 My dad's $800K mistake
25:41 We could never afford school shoes
27:44 Why I'm telling you all this
28:00 The Betts collapse
33:00 A second family business, same mistake
36:17 What NAB's survey says about buyers now
40:00 What's coming in part two

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

Sources:
→ ABS, Household Saving Ratio: abs.gov.au/statistics/economy/national-accounts/australian-national-accounts-national-income-expenditure-and-product/latest-release
→ ABC News, Australia's $1 Trillion Debt: abc.net.au/news/2026-08-21/analysis-national-debt-hits-one-trillion-but-its-nothing/107058026
→ CommBank, Household Spending Insights: commbank.com.au/articles/newsroom
→ ANZ Research, Property Price Forecast: smartpropertyinvestment.com.au/investor-strategy/28035-capital-city-house-prices-tipped-to-fall-10-as-downturn-deepens
→ Stax Liquidator's Report: news.com.au/finance/business/retail/collapsed-aussie-activewear-brand-stax-owing-17m-to-nearly-13000-shoppers-as-documents-reveal-full-scale-of-debt/news-story/46fe4723596cb0948c213974adbac481
→ Betts Voluntary Administration: smartcompany.com.au/retail/shoe-retailer-betts-close-20-stores-voluntary-administration
→ NAB, Consumer Sentiment Survey Q1 2026: nab.com.au/news/economy-markets/nab-consumer-sentiment-survey-q1-2026-cost-pressures-peak-as-consumers-switch

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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90% of podcasts fail by the third episode. Before you buy a single piece of equipment, watch this.

In this solo episode, I'm breaking down everything I've learned after two plus years of podcasting, what it actually costs, what the real ROI timeline looks like, and the mistakes I made that you don't have to.

We get into:
→ Why most podcasts don't even make it past episode three
→ How to actually structure your show before you record a single word
→ The real ROI timeline, and why podcasting is more like investing than marketing
→ DIY versus hiring a premium agency, and how to know which one is right for you
→ What my $30,000 studio fit out actually taught me
→ Why the show is called Delusional, and what that means for founders
→ How a podcast quietly turns into high-ticket clients and rooms you couldn't buy your way into

If you're even a little bit considering starting a podcast for your business, watch this before you spend a single dollar.

Chapters:
0:00 Welcome to Delusional
1:07 Why 90% of podcasts fail by episode three
2:45 How to research and structure your own show
4:12 Who is actually listening, and when
8:38 Why the show is called Delusional
9:40 Building a community, not just an audience
15:15 The ROI timeline nobody tells you about
16:03 DIY vs hiring a premium agency
16:48 Why I didn't believe in myself starting out
21:39 The real cost of a full studio fit out
22:37 How a podcast turns into high-ticket clients
26:17 Industry association: the thing you can't buy
27:44 Final thoughts before you hit record

Got a question about starting your own podcast?
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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I came into this episode a bit sceptical about influencers, and I walked out completely rethinking how I see them.

This week I'm sitting down with Bree Connor, founder of Now Socials Co, model turned PR and influencer marketing powerhouse, to talk about how brands actually earn their place as industry leaders.

Bree sold her car to go on a modelling trip she couldn't really afford, and within 24 hours of getting home she had three clients and the beginning of an agency. We also get into the parts of her story that never make the highlight reel, including what it was like wearing a wig through high school and how that experience quietly shaped the way she shows up now.

→ Why your social media is your business resume, whether you like it or not
→ The real reason influencers matter (hint: it's not about who buys from them)
→ How to pick the right influencer so it doesn't blow up in your face
→ What it actually costs to run a PR event that gets results
→ How one event pulled in $21,000 in a single day for one of my own clients
→ Why personal brand, UGC and influencer marketing all feed into each other
→ Handling public criticism as your business grows
→ Building a business and a family without losing yourself in either

CHAPTERS
0:00 Cold Open
1:04 Welcome & Meet Bree Connor
4:45 She Sold Her Car for a Trip That Changed Her Life
10:00 The Wig, the Bullying and Building Self-Worth
14:00 Handling Online Negativity as You Grow
18:00 Leaving Her Job to Go All In
26:00 Redefining Success, Marriage and the Family Question
42:00 How Brands Actually Become Industry Leaders
45:00 Choosing Influencers Who Actually Move the Needle
55:00 Planning a PR Event That Actually Converts
1:09:00 Bree's Advice and Where to Find Her

If you found value in this episode, drop a comment and let me know what stood out to you most, I read every single one.

CONNECT WITH BREE CONNOR
→ Website: nowsocialsco.com
→ Instagram: @breeanneconnor
→ Instagram: Now Socials Co

FOLLOW DELUSIONAL
→ Instagram: @sammykennedyofficial

Chapter timestamps are estimated from the raw transcript's minute markers, worth checking against the locked edit before publishing.

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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Ever wondered why a $1,500 a month agency can end up costing you more than a $5,000 one? In this episode I sit down with Nina Youé, founder of social media agency Flicker, to pull apart everything nobody tells you about hiring for your marketing.

→ Why chasing ads before you've nailed your brand is setting your money on fire
→ The real difference between a $1,500 retainer and a $5,000+ one (and why the cheapest agency "doesn't have staff")
→ How one Instagram follower turned into $1,200 in revenue
→ Top, middle and bottom of funnel content, explained simply
→ Why Nina rebranded Flicker twice, and what finally made it stick
→ The mindset shift from posting for likes to building a personal brand people actually trust

Nina started with zero experience in the space and built Flicker from the ground up, and this conversation is proof that the messiest starting point can still lead somewhere incredible, if you're obsessed enough with getting it right.

If you found value in this one, take a screenshot, share it to your stories and tag us both with your biggest takeaway. I'd love to know what landed for you.

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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I met a woman who was born on a dirt floor in Peru and couldn't read until she was seven. Now she's a business coach, keynote speaker, author, and the person some of the most successful women I know call when their life looks perfect from the outside and feels completely empty on the inside.

Marcia Colosi and I talk about the relationship stuff nobody wants to say out loud. Why busy is not a flex. Why over mothering your husband is a problem. Why the wrong partner can bankrupt you long before your bank account shows it. And why chasing a goal doesn't always feel the way you think it will once you get there.

→ Why "busy" is actually just time scarcity in disguise
→ What it really means to date yourself first
→ Why over mothering your husband is quietly wrecking your marriage
→ We don't attract what we want, we attract what we are
→ The subtle signs someone in your life is toxic for you
→ Why a man is not a financial plan (and neither is a woman)
→ The "time mates" concept, and why some people are only meant for a season
→ Why nobody is actually self made

This one made me want to call my partner the second we stopped recording.

Follow Marcia: @marciacolosi
Podcast: The Marcia Colosi Show

If this episode gave you something to think about, leave us a rating or a review, it genuinely helps more people find the show.

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