Advice on money, property & investing.

Should you buy cryptocurrency during a market dip?

Tommy admits he considered texting Jess during a crypto crash to say it was a good time to buy, but acknowledges he doesn't actually know if that's true and is 'just making shit up,' suggesting caution about assuming dips are good buying opportunities without real expertise.

How can buying in bulk save money?

Josh suggests that if you have spare cash, it can be cost-effective to buy non-perishable items like toothpaste or toilet paper in bulk, as referenced via advice attributed to Mark Cuban about investing cash into bulk purchases.

What should you consider before buying in bulk?

Tommy and Josh note that bulk buying only makes sense if you have adequate storage space at home, otherwise it becomes impractical even if it saves money.

When can you clean or swap your golf ball during a round?

Josh explains that while putting on the green, you're allowed to mark your ball's position, pick it up to clean it, and place it back down, and you can also swap to a fresh ball once a hole is finished.

How should a beginner get into cryptocurrency investing?

Have a friend who already understands it help set up an account and start with a minimal, low investment amount to build curiosity and learn by doing rather than trying to understand everything upfront.

How can you tell if a supermarket avocado is actually ripe?

Check by touch, and look toward the bottom of the display pile, as the ripest, softest avocados are reportedly placed there by the store.

Is it a good idea to buy Bitcoin right now?

Tommy advises against buying Bitcoin unless you have surplus money you wouldn't miss, pointing out that even owning a full coin or two at ~$74,000 is a small stake relative to the risk, and that you shouldn't buy with money you need.

How much should you invest in speculative assets like crypto?

Don't invest anything you're not okay with losing, and don't bet the house — treat speculative investing as something you can afford to lose entirely.

How should an everyday person approach long-term investing without chasing hype?

Consider index funds/ETFs that buy into a broad basket of companies and hold them for a long period, paying a small management fee, rather than chasing individual hot stocks or trends.

How can you afford to live somewhere you love while still building wealth?

Consider 'rentvesting' — rent in the location you want to live in for lifestyle reasons, while buying an investment property somewhere more affordable.

How should you respond to an unwanted telemarketer call?

Josh suggests you can turn it into a game by giving minimal yes/no answers and asking odd follow-up questions to see how long you can keep the caller on the line before they lose patience.

What should you do to prepare for digital legacy planning (passwords, domains, accounts)?

Josh suggests proactively telling partners where important passwords and account details are stored so that if something happens to you, they can access critical accounts, referencing the real-world case of someone losing access to a large crypto fortune.

How do you communicate an evolving business vision to investors?

Maintain constant, close communication with investors, revisit your original vision regularly to check you're on track, and recognize that investors are betting on you and your story as much as the product.

How can you protect an idea before you've fully developed it?

George suggests informal 'poor man's copyright' methods like writing the idea down, dating it, emailing it to yourself, or mailing it to yourself with a postage stamp to create a timestamped record.

How do you avoid having your business ideas stolen or copied?

Josh argues that merely talking about an idea doesn't give you ownership of it — until you actually execute the idea, it's hard to claim it as yours, so spending too long just discussing something is risky.

Should you buy or rent a beehive if you want to harvest your own honey?

Mason suggests renting an urban beehive (around $600/year) rather than owning one outright, since a provider handles maintenance every 4–6 weeks and you avoid the risk of the hive 'getting out of hand,' though it requires having a backyard or land.

How should couples handle splitting money/expenses?

It's fine to keep finances separate early in a relationship (e.g., taking turns paying for dinner) and only consider a shared account once bigger shared goals arise, like buying a house together; for travel, depositing an agreed shared amount into a joint account for that trip can work well.

Should I withdraw $10,000 from super early during COVID-19?

Think about the long-term cost: $10,000 withdrawn now could mean roughly $100,000 less at retirement due to lost compounding. If facing genuine financial hardship, talk to a financial advisor or accountant before deciding, and avoid investing the withdrawn amount personally since personal tax rates (up to 32.5-45%) are much higher than super's 15% rate.

How much financial savings should I have in uncertain times?

Build a financial buffer rather than relying on social security or an employer; Matt aimed for and secured a full year of rent and expenses saved before quitting freelance work to go full-time on YouTube, since job security can't ever be 100% certain.

How do I choose the right investor for my startup?

Be selective about investors — only take money from people you'd be comfortable having a long-term relationship with, and ensure they understand and support your business model (e.g., not objecting to spending on hiring).

How should authors approach preorders and bestseller lists?

Nash advises authors to create added-value incentives for preorders (bonus content, sessions, PDFs) and route sales through retailers rather than self-fulfilling, since only retailer-reported sales count toward bestseller lists like Nielsen BookScan.

When is the right time for a business to take outside investment?

It depends on the business model and how fast you want to scale; building a self-funding business is slower but creates a robust model that can weather downturns, whereas raising money buys time and allows more experimentation but comes with pressure to hit growth targets and can become a full-time pursuit in itself.

How should someone start learning to invest without risking money?

Set up a mock or 'play' portfolio on an investing platform, track pretend trades over time to build understanding and test your skills before committing real money.

Should I invest while I still have debt?

Pay off high-interest personal debt (e.g. ~17% personal loans) before investing since your investment would need to beat that rate to be worthwhile, but low/no-interest debt like HECS can be deprioritised in favour of investing in the share market.

Is chasing money a sustainable path to happiness?

Money alone can't buy happiness; chasing it without self-awareness just becomes another form of 'sugar' that wears off, whereas doing work you're passionate about tends to generate money as a byproduct rather than the primary goal.

Is it worth stressing over superannuation and financial planning?

Derek argues financial advice can be overrated stress; if a saving strategy (like putting away a high percentage of income) genuinely calms someone's anxiety and makes them happy, it's worth doing, but otherwise people should prioritise enjoying their money now rather than worrying.

Should you consolidate old superannuation accounts?

If you have a dormant super account with little money and no contributions, consolidate it, because ongoing account fees (even small ones like ~$80/year) will erode the balance over decades.

How can two business partners divide social/networking responsibilities?

Josh proposes that within their partnership, Tommy can be the 'friend finder' who builds relationships (like with café manager Lawrence) while Josh doesn't have to actively socialise, and they both still benefit indirectly.

How should creators approach asking people for money/investment?

Get comfortable with asking for support (financial, audience, attention) by framing it as selling a product/experience rather than just asking for cash, and take people on the journey with you.

How should I approach cutting unnecessary subscriptions or spending?

Strip everything back to zero and then only add back what you actually need and use — similar to emptying your closet and only putting back clothes you actually wear.

What's the fastest way to effectively make more money?

Look at where you can cut or save money, since saving money is functionally the same as earning it, especially if you can't simply increase your salary.

What should you do if a company's fraud/verification team asks for personal details without first verifying your identity?

Push back and ask the representative to first verify your own identity details (like date of birth) before they disclose or request account information from you, since failing to do so is a red flag that the company itself has a process gap.

How do you build a support network / 'board of directors' for your career?

Build relationships with sponsors, mentors, and advisors before you need them, since responsibility for securing work is shifting to individuals; when things go wrong, a deep network of people who trust you will want to help.

Should I buy cheap or grass-fed/ethical meat when budgeting groceries?

Decide based on whether you have the money and want to be ethical (get grass-fed) versus needing to simply feed yourself affordably (get the cheaper option); work out why you're saving money and what you're actually cooking before deciding.

How do you find cheap but ethical groceries like eggs and meat?

Shop around at multiple local places to find options that are both high quality/ethical and cheap, and consider bulk-buying and freezing meat to save money without sacrificing ethics.

How can you negotiate successfully when buying a house?

Be prepared to walk away, make a firm take-it-or-leave-it offer backed by a cheque and fast settlement timeline, and factor any extra concessions you want (like fixtures) into your initial offer.

How should you think about your spending and savings?

Periodically review your actual spending by category (food, entertainment, etc.) rather than letting it drift unnoticed, and align spending with what you genuinely care about (e.g., skipping alcohol) to make it easier to save.

How do you decide whether to pursue a risky idea or career move?

Weigh what you perceive as the 'safe' option against your own nature — sometimes staying in the 'safe' lane (like finishing a law degree while doing nothing else) is actually the bigger risk if it doesn't suit who you are; take the 'smart risk' instead.

How do I know if I should keep doing something I feel obligated to do (like maintaining a social media presence)?

Tommy advises going deeper into why you feel you have to do something — asking 'why have you got social media?' repeatedly — because often the real answer ('to build a following') doesn't hold up, and people may be doing things by default rather than by choice.

Should you message or try to meet up with someone online if you already have a partner?

Josh suggests it's more acceptable to talk to someone online with open intentions before being in a relationship; doing so while partnered to see if it 'could go somewhere' is the problematic part.

If buying multiple properties, which one should you buy first?

Josh advises buying the property you will personally live in first, prioritising the one where you'll spend the most time, and sorting out investment logistics with an accountant later.

Is it worth setting up a self-managed super fund?

Tommy and Josh agree, citing a friend's experience and Barefoot Investor advice, that self-managed super funds are generally not worth the complexity and effort unless you already have substantial money to optimise.

How should you think about long-term goals and life direction?

Josh suggests meeting in the middle between overthinking and underthinking big life decisions, then committing to a direction and adjusting course along the way rather than over-planning tactically.

How do some wealthy individuals legally reduce their tax burden internationally?

Josh explains that some people renounce or change citizenship/passports to avoid double taxation (particularly US citizens abroad), and that there are location-based versus citizenship-based tax systems to understand when optimizing tax exposure.

How should you think about spending money on friends (coffees, meals) without keeping score?

Don't track small transactions transactionally; trust that generosity balances out over time, and avoid being seen as a 'tight ass,' while still being mindful of your own financial means.