Advice on business & entrepreneurship.

Should you avoid a business partnership because you've heard partnerships end badly?

Don't let other people's bad partnership experiences stop you — go through the partnership anyway, because whatever happens (even losing money or ending in debt) is the version of the experience you need to go through to learn from it.

How should you think about the cost of shutting down a business or ending a long-running project?

Put short-term costs (like lease payouts) in perspective against the scale of the long-term investment you'd otherwise be making; don't let sunk-cost thinking or short-term pain prevent a decision that makes sense long-term.

How should you think about ambitious plans that don't work out (e.g., due to unforeseen events like COVID)?

Josh advises that just because an ambitious plan (like a studio with bleachers) didn't pan out due to circumstances doesn't mean you shouldn't have attempted it; the risk of 'the guillotine coming down' is part of doing meaningful things.

Should I write down my life or business plan?

Writing down goals/plans can be valuable, even if you don't look at them again for years — looking back later can reveal how much progress was actually made; the plan doesn't need to be a strict business document, it can be reflective questions about the kind of partner, parent or business partner you want to be.

What's the risk of not having focus in a business?

Spreading attention across too many pillars (podcasts, client video work, multiple shows) without clear focus leads to failure; identify your core strengths and commit resources there before expanding again.

Should you follow other successful people's exact business advice/hustle culture?

Josh argues that a 'story' that worked for one person (like Gary Vee's hustle-hustle-hustle approach) is toxic advice for many others, and that if you told someone to copy exactly what you did, it likely wouldn't work for them because everyone's context differs.

How can trainers keep client progress from going stale over time?

Work in structured review cycles (Craig uses 28-day blocks) where you reassess diet, goals and performance together with the client, turning an emotional, stop-start process into one driven by strategy and logic.

How should a creator figure out what content to focus on?

Start by asking what you enjoy doing most and what will bring you the most joy, then work out who you're creating for — once you have a clear sense of audience, everything else about the content strategy becomes easier.

How do you get a candle to burn evenly without wasting wax?

Make sure to cut the wick, and let the first burn go all the way to the edges of the candle so the full top layer melts; if that didn't happen on the first burn, a blowtorch can be used to melt the outer wax down to a flat, even surface.

How can you handle awkward small talk before a business meeting?

Use Michael Bungay Stanier-style coaching questions (e.g. 'what's your biggest challenge?') as a reliable foundation, and treat any small-talk suggestions as a loose example rather than a script to repeat verbatim.

How do you prepare for a pitch meeting with people you don't know?

Prepare three background or context questions to ask the other people to ease the awkwardness and shift the conversation's momentum onto them, and write a one-line intro sentence under each slide so you don't have to read directly off it.

How do I navigate uncertainty and lack of control during a lockdown?

Tommy suggests that when external control is taken away, the focus should shift to what can still be controlled internally within the new constraints, rather than trying to force control over things that are now out of reach.

What should new entrepreneurs focus on instead of startup hype?

Focus on identifying and solving a real, simple customer problem rather than getting obsessed with the 'idea' or the cultural cachet of being a founder/entrepreneur.

What's missing for small businesses trying to grow?

Most small businesses never nail a consistent, predictable 'selling system' (how they reliably turn prospects into customers); establishing one is key to scaling.

Should I start a restaurant with borrowed money?

Don't borrow money to get into hospitality — have your own cash, because margins are extremely tight (3-6%) and the failure rate is very high; you can't afford to be partners with the bank.

How do I build a successful hospitality business?

Don't go into hospitality purely for the bottom line; lead with generosity, control food cost/labour cost/occupancy cost from day one, and build real business knowledge (courses, TAFE, university) since it's not just about cooking or service skills.

How do you find and hire the right people for a growing business?

Look for people who 'lead from the heart' — prioritise passion and commitment over pure skill, and trust gut instinct over an overly analytical hiring process; acknowledge it's genuinely difficult and there's no magic formula.

How do you get staff to buy into a tough strategic pivot?

Communicate with genuine passion and honesty; people who don't sign on after that simply aren't the right fit, and you have to be brave enough to accept that rather than forcing everyone on board.

Should a scrappy early-stage startup pay a lawyer to draft terms and conditions from scratch?

Avoid spending money on lawyer-drafted contracts before you have a customer base (maybe before even 10 customers); instead use adapted open-source templates and spend your limited money on testing the product and understanding customers, since startups often pivot within months.

If copying another company's contract, what's the minimum you should change?

At the very least, change all personal/company details so the copied document doesn't still reference the original company's name.

When should a growing business set up separate legal entities for different parts of its operations?

Don't over-structure early; set up a new entity once there's a serious, distinct opportunity (e.g., different investment paths, different sale prospects, or new people joining who need equity in only one part of the business) rather than paying thousands upfront for entities 'just in case.'

Should a startup invest heavily in trademarking early on?

Trademarking can be very costly and isn't always worth it; competitors can often get around protections anyway, so it's often better to focus time and money on strengthening your own brand rather than fighting every potential infringement.

What does it take to successfully disrupt a legacy industry like banking?

Pym says success requires both curiosity (the willingness to ask 'could we build this better?') and confidence (the guts to stand up against 200-year-old institutions with billions of dollars), a lesson he says he learned as a kid from hearing Dr. Karl on Triple J.

How should a startup decide which ideas or companies to back?

Pym says he prioritises the people and their passion over the idea itself, but notes the idea still needs to be commercial and monetisable, or even a good idea will fail; he also values ideas that are impactful for others even if non-commercial.

How should a growing small business handle the need for specialized roles like community management?

Start by having generalists do a bit of everything, then as the business grows, split roles into specialists (e.g., a data analyst, a dedicated comments/engagement person, a content creator) because trying to fluctuate between content creation and engagement is difficult to do well simultaneously.

How do you let go of control when growing a team or business?

Accept that you can't do everything yourselves — identify the skills and expertise you're lacking, bring in people you trust for those areas, and let go of needing to be across every single part of the business.

What's a mistake to avoid when deciding on future business arrangements?

Scooter Derek warns against making absolute vows like 'I will never do this again,' saying that's one of the biggest mistakes you can make after a bad experience.

How should freelancers think about pricing their work?

Price and value are not the same thing; the way to earn more isn't to work more hours or hire help, but to get better clients, since better clients pay more, demand more, and lead to even better clients.

How can a new business stand out in a crowded market?

Identify the thing that genuinely differentiates you (your unique experience/lens), favor slow compounding growth over hockey-stick growth, and resist being commoditized by leaning into creativity and originality rather than just production capability.

How should I invoice a US client if I'm GST registered?

If the service is exported offshore it's typically GST-free, so no GST is charged. If GST does apply, include a statement converting the GST amount to Australian dollars using the RBA exchange rate on the invoice date, since GST must ultimately be reported in AUD.

How do I correctly charge GST when getting reimbursed for a client expense?

Work out the GST-exclusive cost of the item (e.g. an $88 item is $80 + $8 GST), then charge the client that same $80 plus GST, rather than charging GST on top of the full $88, to avoid over-collecting.

When should a freelancer or small business move from sole trader to a company/trust structure?

Start as a sole trader to prove the business concept with low cost and low barrier to entry, but once you start taking on real risk, assets and liabilities, move to a company or trust to get personal asset protection and better tax planning options.

How should businesses communicate with customers during a crisis like COVID-19?

Avoid generic, performative messaging like 'these are unusual times' emails; instead provide actual factual, changing information (how things are affected day to day, what support is available) and proactively reassure key stakeholders directly rather than blasting generic statements.

How can small/agile businesses support enterprise customers during a crisis?

Reach out directly to key contacts (e.g. IT managers) to reassure them of business continuity, and offer free resources like webinars to help customers transition to remote work.

How can you support local cafés during lockdown without over-relying on delivery apps?

Josh describes using a 'skip the queue' system at his local café, where customers order ahead, pay, and wait outside for the owner to bring the coffee out, avoiding dine-in restrictions while still supporting the business directly rather than giving a cut to Uber Eats.

How can a coach or business owner respond to clients right now instead of selling?

Listen more than you speak, let clients be heard and grieve if needed, avoid prospecting for new business too early as it can seem insensitive, and consider offering free sessions or trading skills with people who are struggling.

What should people be doing to support local businesses during lockdown?

Order food delivery (like Uber Eats) and buy things like coffee or croissants from local cafes even if you don't necessarily need them, as a way of supporting the local economy and businesses during the pandemic.

What relief is available for small businesses struggling with payroll during COVID-19?

Check with your accountant about the ATO's credit system, which offsets payroll tax (PAYG) and GST owed on your BAS (up to $25,000) for businesses under $50 million turnover, incentivising businesses to keep staff on payroll.

When should a small business start paying for software instead of using free tools?

Once a business has any real size, paying ~$50/month for tools like accounting software is a no-brainer investment that can 'revolutionise' operations; sticking with free tools at that stage is a false economy.

How do you keep documents and feedback organized as a team grows?

Move away from scattered folders/emails (e.g. Google Drive) toward a centralized system like Basecamp where notes, documents and tags can live together and be referenced by everyone, since ad hoc systems that work for one person break down once more people are involved.

Should I join a startup accelerator?

Only join an accelerator once you're fully committed to the business and open to changing your approach; accelerators only deliver value if you're willing to experiment and learn, and quality varies significantly between programs.

How can a business owner avoid tying their self-worth to their company's success or failure?

Nash advises founders to mentally separate themselves from their business the way you'd separate yourself from a car, relationship, or sports team allegiance—recognizing 'you are not your business' so that wins and losses don't trigger self-sabotage.

What makes a business model sustainable long-term?

Nash argues a business needs a 'win-win-win-win' structure where the company, its customers, its suppliers and its employees all benefit; models that squeeze any one group (as he claims Amazon and supermarkets do to suppliers/workers) are not sustainable.

How do I figure out what I actually want from my work or business long-term?

Imagine you've been given $10 million with no constraints on time or money — once you've bought the material things you want, what would you actually do with your time? The answer reveals your real motivations.

How should founders deal with their personal weaknesses in running a business?

Double down on your natural strengths and value your time enough to pay someone else to handle tasks you're not good at, rather than spending excessive effort trying to fix weaknesses.

How should I approach asking for a pay rise?

Prove your value with research (e.g. salary guides), avoid citing mere tenure as justification, and have an honest conversation with your manager about your contribution versus your remuneration; if the employer genuinely can't meet your value, consider leaving.

How should freelancers or creatives handle unpredictable income?

Learn to use a spreadsheet (Excel) to track cash flow and calculate exactly how long you can survive without new income; this removes anxiety about not knowing where the next paycheck is coming from and lets you plan which projects to prioritize.

How do I choose a business coach that's right for me?

Determine what you want to get out of it before going in, how you'll show up, and find someone whose personality you mesh well with and whose history or achievements make them a credible role model.

Should a business try to do everything or specialise in one thing?

Max advises specialising in a narrow niche (comedy content only) rather than offering a broad menu of services, using the analogy that a restaurant serving only ravioli is more trustworthy and distinct than one with 150 menu items, even though saying no to broader, more lucrative work (like wedding videos) is difficult.

Why shouldn't business owners be afraid to talk about profit?

Profit isn't something to shy away from discussing — a lack of profitability puts employees' jobs, mortgages and families at risk, so treating profit as taboo is a disservice to everyone who depends on the business.

How do you build a business that stays good as it grows?

Stick to your core values and philosophy as you scale; many businesses cut corners and compromise on product/service quality once they grow, which erodes what made them special in the first place.

How should you approach collaboration when building a business or creative project?

Always try to collaborate with people smarter or more skilled than you in their specific craft (e.g., a better producer, chef, architect), because the outcome improves when they're invested and talented—you never want to be the smartest person in the room.

How should profits be handled across multiple businesses?

Decide whether to take dividends or retain all profits for reinvestment and growth; a hybrid model (partial dividend, rest retained) can work, but retaining profit avoids constantly having to raise cash for new projects.

How should a startup founder respond when they don't know the answer to something?

Say 'I'm not sure' rather than bluffing — it signals confidence rather than weakness and should be followed by a plan to find the answer; investors and team members who react badly to that phrase are not the right people to have around you.

What should someone consider before starting a business in the US as a foreigner?

Go 'all in' — fully relocate, take on real personal and financial risk, and commit rather than trying to run things remotely from Australia; Americans can tell who is genuinely committed and will back those who are.

Which US cities should newcomers target if New York or LA feel too competitive?

Consider 'tier 2' cities like Austin, Nashville, Miami, San Diego or Seattle, which have lower costs, lower taxes, and growing opportunities, and can serve as a stepping stone before attempting bigger markets like New York.

How should someone start a shoe or fashion brand with limited money?

Treat limited funds as a forcing function for disciplined decisions, build the business model before the product, hire only people who directly cover their own cost and add revenue, and avoid overextending just because capital is available.

What's a good way to collaborate with other comedians on material?

Ash suggests simply catching up with comedian friends in cafes or shared spaces and talking through bits out loud — the act of voicing an idea to someone else often helps you finish or improve it yourself, regardless of whether the other person directly contributes.

How do creatives get past self-doubt to succeed commercially?

Josh says creatives spend huge energy convincing themselves they're good enough and that their work isn't crazy, but the real ongoing challenge after that is convincing other people if you want to make a living from your creative work.

How should freelancers think about pricing their work?

Price and value are different things; rather than working more hours or lowering prices, freelancers increase their income by landing better clients, since better clients pay more, demand more, and are more likely to say yes to great work, which attracts even better clients.

How should founders think about their personal weaknesses in a business?

Know what your weaknesses are and have an ego big enough not to worry about them—outsource the things you're not good at so you can focus on what you do well, which leads to more enjoyment and better results.

How can someone decide whether to keep looking for new opportunities or stick with their current path?

Happiness and satisfaction come from autonomy, mastery and purpose; if those three things are present in what you're doing, you'll find creative fulfilment there rather than needing to constantly look elsewhere—restlessness may be more about looking within yourself than for another external thing.

How can you keep track of business receipts easily?

Take a photo of receipts on the day you get them, then use the Google Photos app's search function, which automatically recognises and lets you search for 'receipts.'

How do you overcome overthinking and actually start a new creative project?

Rip the band-aid off rather than overthinking; commit early (e.g., booking a first guest) to force yourself to follow through, and treat the first version as a minimum viable product rather than waiting for perfection.

When is the right time to leave your job for a side business?

Leave when the job and the business become mutually exclusive — i.e., when you start turning down business opportunities purely due to lack of hours — rather than picking an arbitrary revenue figure.

How should freelancers structure payment terms to avoid being paid late?

Ask for a deposit (framing it as a 'deposit' rather than '50% upfront' to leverage psychological priming), and require 100% payment before delivering final files, since clients who are slow to pay often also need the work urgently.

What can a freelancer do if an invoice isn't being paid?

Offer to turn on credit card payment facilities (passing on the ~2% fee) and reissue the invoice, which removes friction for clients who are disorganised rather than unwilling to pay.

Should a small business save cash or reinvest it?

Rather than parking surplus cash in savings or superannuation for minimal interest, reinvest available funds directly into growing the business (equipment, content, time) since the business itself is the higher-return asset.

How do you actually know if a small product-based side business (like candles) is profitable?

Be pedantic about tracking costs — allocate a specific marketing budget, know the true cost price per item, and account for things like shipping and free giveaways rather than guessing at profit.

Should you shop at big online retailers like Amazon or local businesses?

Prefer supporting local and small businesses (e.g. local bookstores, cafes) over broad subscription services like Amazon Prime, which Tommy frames as undermining local commerce.

What are good icebreaker questions to ask someone new?

Ask questions like 'if you could live anywhere in the world, where would it be and why,' 'what's your favourite place to holiday,' or 'if you could have any career, what would it be' rather than generic small talk.

How should freelancers price their quotes to avoid undercharging?

When finalising a quote, add more than feels comfortable — Josh describes a rule of adding $5, then more, because fear of client pushback rarely materialises, and most people especially underquote for pre-production/planning time.

How do you price for difficult or ambiguous client projects?

Do a retrospective after each project to calculate actual hours spent versus quoted, and build a 'bullshit tax' into future quotes for clients or projects with high ambiguity or difficult communication.

How do you decide what to charge based on value rather than hours?

Consider the cost to the client's business if the work fails or the impact it will have, rather than just hours spent, to determine a fair price.

How should I behave in a first meeting with a potential client?

Know your audience, dress appropriately but be yourself, approach the meeting with curiosity about the other person rather than your own agenda, and aim to build trust through genuine conversation rather than pushing a sales pitch.

What's the key to making a business or creative collaboration actually work?

Tommy suggests that most people enter collaborations with self-interested motives (to grow their own following or reach), and that collaborations work best when one person leads the charge and the other supports, rather than trying to keep everything on equal footing.

How should creators think about pricing their work and avoiding undervaluing themselves?

Ask fans directly what they'd actually pay, and recognise that audiences are often happy to pay a fair price rather than feeling ripped off; undercharging (e.g., Lewis's early $20-25 tickets) can prevent you from funding future projects, so price should reflect real value, not fear of asking.

What's the key to building an audience that will financially support you when you ask?

Give away as much free, consistent, honest content as possible for years before ever asking for money; when you do make an ask, your audience will feel invested enough to show up.

Should you work for free early in your creative career?

Yes, working for free early on helps build reputation, portfolio, and systems; set yourself a deadline (e.g., six months) and then start trialing and increasing prices to find your market value.

How should creatives think about money and sustainability?

Establish a clear budget and cash flow so creativity isn't hindered by financial stress; automate saving a percentage of income, and build professional, organized back-end systems (like proposals and packages) to be taken seriously by brands.

How do you deal with the pressure of a big business partnership like a long lease?

Tommy frames the added pressure of a multi-year lease as something that can empower rather than disempower you — accountability to a business partner can drive you to do work you otherwise wouldn't.

How do you manage multiple influencers/talent without conflict?

Keep the roster 'complementary not competing'—ensure signed talent occupy different niches so they're never fighting for the same brand jobs.

How can influencers avoid damaging their personal brand with sponsored content?

Say no to brand deals that don't align with your authentic image or audience; maintaining a 'brand no-no' list protects long-term trust, which is more valuable than short-term payouts.

How do you get past feeling awkward charging friends or customers for your product?

Nate says it's hard at first but you have to learn that real friends want to see you succeed and are happy to pay; people who only want free stuff or discounts aren't worth keeping around.

When should a growing business cut underperforming products or staff?

Nate compares it to airplane oxygen masks — you have to secure the core business first (even if it means painfully cutting profitable-seeming product lines or staff) so you can keep helping everyone else.

How should an aspiring comedian or creator approach marketing versus just doing gigs?

Success in comedy ('show business') requires more than grinding out gigs — it requires marketing, branding, and understanding your audience/demographic; doing the business work alongside the creative work is what separates profile and income from just having a good show.

Should you take low-paying creative or passion projects in your 20s?

Josh advises doing free or low-paying creative work in your 20s before the responsibilities of mortgages and kids arrive in your 30s make that kind of risk-taking harder.

How should an early-stage founder approach pitching investors when they lack hard metrics?

Play to your strengths and pair with a co-founder who can handle the numbers; know which lens different investors care about (metrics vs. marketing story) and lead with whichever resonates.

How should you manage someone who feels they don't have enough time to finish a task?

Rather than micromanaging by watching someone's every movement, be output-driven and work with the person to carve out specific time (e.g., 'what about this hour here or this 30 minutes there') to get the task done.

How do you divide roles when collaborating creatively with a partner?

Decide who is leading a given project and let the other person act as supportive 'hands'—asking what's needed (camera, setup, etc.) rather than insisting on equal creative input every time; roles can swap on different projects.

Is friction in a business partnership a sign something is wrong?

Friction can be a normal and expected part of commitment and growth—similar to hard patches in a long relationship—rather than automatically a signal to quit.

How do you make friends as an adult?

Adult friendships typically form through spending a lot of time with people at work; look for workplaces or activities aligned with your core values, and understand that friendship is reinforced by repeated close contact (similar to how co-workers become close).

How can creative freelancers avoid burning out and maintain quality?

Matt suggests charging significantly more for your work rather than taking on high volumes of low-paying projects, which allows you to focus more time on fewer projects and say no to work you don't care about.

How do you make better creative videos when you're not naturally funny on the spot?

Matt recommends putting more time into pre-production and planning content in advance rather than relying on spontaneous creativity, which he found was the biggest lesson after reshooting a minimalism video he wasn't happy with.

Should a creator take equity or percentage deals with brands instead of a flat freelance fee?

Be cautious with profit-share deals since they require significantly more time, business logistics, and partner involvement than straightforward freelance work, and may pay less for more effort unless you're a true believer in the product.

What's the best advice for starting a business partnership?

Communicate constantly and put everything on the table rather than bottling up feelings to avoid hurting each other; discuss every minute detail, don't take disagreements personally, and accept you'll make mistakes and get upset with each other just like in any close relationship.

How can a B2B service business structure a Black Friday-style promotion?

Josh, Tommy and Russ Keys land on offering a free one-on-one/two consultation session on video production strategy, allocated by having interested people email in and selecting a winner via randomiser, rather than a straight price discount.

What should business partners do to make the relationship last?

Genuinely want each other to succeed, accept you'll annoy and frustrate each other as humans, talk issues through and return to 'home base,' and recognize each partner will prioritize themselves/their family without that being selfish or incompatible with caring for the other.

How can a company figure out its priorities before chasing revenue?

Define your values first (not just how to make money), then use those values as a filter for every yes/no decision, which reduces conflict and clarifies which opportunities to pursue.

How should a business approach creating company values?

Spend dedicated time (even just half a day) deconstructing past problems and testing how a set of values would have resolved them; values are most useful once you've already experienced business mistakes, but even attempting the exercise early is valuable for clarifying what you do and don't want.

How should you handle demanding or scope-creeping clients?

Take responsibility rather than blaming the client; 'lead the way' by clearly articulating your process and what you offer, and be willing to tell a client that what they're asking for isn't what they actually need.

How do you get more honest answers when interviewing people about business or life?

Push past the default positive response ('yeah, I'm good') by asking more specific follow-up questions, since people's defaults don't reflect the full truth and honesty is what audiences relate to.

Should I just follow my passion to find meaningful work?

Treat 'follow your passion' as bad advice since it assumes you were born to do something; instead follow your curiosity, pursue threads you're curious about, and cultivate passion over time through hard work.

Should a musician think of themselves as an entrepreneur?

Every musician is effectively running a small business, even at the smallest club show there can be roughly 27 different roles (merch, sound, lighting, promoter, agent, manager) they coordinate with, so it helps to consciously own that entrepreneurial role rather than deny it.

What actually makes a business partnership work long-term?

Align on a shared common goal first; partners will still argue, but arguments about process are healthy while arguments about differing goals are destructive. Put intentions in a short 'heads of agreement' document early, and never cite the contract during day-to-day disagreements — only when things are genuinely dire.

How do you keep a business partnership from falling apart?

Establish clear 'informing principles' with your partner early so decisions become easier, maintain strong communication about each other's strengths and weaknesses, and stay solution-oriented when crises hit rather than dwelling on blame—save emotional reactions for after the problem is solved.

How do you balance detail-oriented communication with not being overly nitpicky in a team?

Recognize your own strengths and weaknesses (macro vs. micro thinker) and build a team with complementary skill sets you can trust and empower to cover gaps, rather than trying to do everything yourself.

How should freelancers price their work and attract better clients?

Price and value are different things; you can't scale by working more hours or hiring cheaper help. Instead, charge more to attract better clients, who demand more and are more likely to say yes to good work, creating a positive cycle.

Should you feel guilty using loyalty cards or free coffee rewards at a small cafe?

Don't feel guilty using earned loyalty rewards like a free coffee — you've already paid for it through previous purchases.

How do you know if you're pushing too hard in a negotiation?

Push a little further than feels comfortable; if you get pushback, that tells you the other party's real limit, which can bring comfort rather than embarrassment.

How should founders handle transparency with employees about business struggles?

Be radically transparent with staff about metrics, risks, and the fragility of the business rather than shielding them, so they understand how businesses actually work and can grow from the exposure.

How do you build a successful business partnership?

Remove ego entirely, give each other blunt feedback even when painful, and trust that the other person's criticism comes from care rather than a desire to undermine you.

Should you negotiate or walk away from client/agency relationships that overstep agreed scope?

Set a personal standard for how you're willing to be treated, communicate boundaries upfront rather than waiting until you're cornered, and be willing to walk away from retainers that don't respect that standard.

How should I approach growing a business or project?

Focus on learning fast but growing steady rather than chasing rapid success; you can't skip the time needed to build real experience, much like you can't skip years to become older than you are.

How can you avoid being overcharged or confused by pricing abroad (e.g., per-weight pricing)?

Josh advises paying close attention to signage details like 'per 100 grams,' since his focaccia overcharge wasn't a scam but a result of not registering the weight-based pricing on the sign.

How can travelers avoid being shortchanged or overcharged abroad?

When handing over cash, clearly state the denomination you're giving (e.g., say 'here's €50') to prevent vendors from claiming you gave a smaller note than you did; also be wary of signs advertising 'tourist deals.'

How should you balance vigilance against being scammed with enjoying travel?

Be mindful of common tourist scams but don't let suspicion dominate every interaction, as being overly guarded (e.g., interrogating a free sample) can undermine a good travel experience; find a balance between caution and enjoyment.

Do I need to work extremely long hours ('hustle') to succeed?

Don't adopt someone else's intensity (like Gary Vaynerchuk's) unless it serves your actual goal; instead focus on the few things that matter to you and do them well rather than wearing busyness as a badge of honour.

What should I consider before going into business with a partner?

Look for a partner who is in a similar life position to you (similar sacrifices, similar financial stakes, similar long-term commitment) and make sure you can actually work together daily, even when tired or stressed, not just when things are easy.

How should you manage contractors or new hires effectively?

Josh suggests that being overly easy or generous with contractors doesn't necessarily improve their effort, and that clear expectations and operational clarity ('this is what I expect') may be more effective than trying to be accommodating.

How can you delegate creative or complex work to others?

Tommy advises breaking a task into multiple smaller tasks so that people without big-picture understanding can still contribute meaningfully, framing creative work as a process that can be pulled apart stage by stage.

How much should I budget for a new website?

For a custom-built site from a freelancer or small agency, budget roughly $2,500 on the low end up to $5,000 for a fuller build; alternatively, templates from marketplaces like Envato can cost $60-$80, or use a DIY platform like Squarespace.

Should I outsource my website/SEO work overseas to save money?

Be cautious with cheap outsourced tech teams—quality can be poor, custom code can be botched, and payment disputes can arise, so set clear payment terms upfront and be prepared to protect your accounts.

How do you charge friends or acquaintances for creative work without feeling guilty turning down other paying jobs?

Charge even friends some amount for your time so you don't feel guilty saying no to other work, and so they value the time being set aside for them.

Should I keep a backup 'Plan B' when pursuing an ambitious goal?

Avoid having a Plan B because when Plan A inevitably gets difficult, you'll default to the easier backup option instead of pushing through.

How should freelancers/agencies handle client scoping and pricing?

Ask detailed clarifying questions upfront (number of cameras, deliverables, format) before quoting, rather than agreeing to vague scopes; be willing to push back when a brief lacks detail, since professionals create friction points where needed.

How can a video production business filter out clients who are only price-shopping?

Ask prospective clients early what specifically they like about your previous work; if they can't answer, they're likely just collecting generic quotes rather than valuing your specific style.

How do I stand out and charge more as a freelancer or creative?

Avoid commoditising yourself by listing gear or rates; instead sell based on the value and experience you provide, believe genuinely in that value, and focus on delivering results rather than being easily categorised like a mass-produced product.

How much should you pay a young employee or work-experience hire?

Tommy suggests deliberately not overpaying inexperienced workers, arguing that paying minimum wage creates useful 'friction' that forces the person to decide whether they're motivated by growth/opportunity rather than just money.

Is 'failing fast' always good advice for business/growth?

Tommy reframes 'fail fast' as meaning daily execution and iteration rather than scaling too quickly, warning that rapid hockey-stick-style success often precedes rapid collapse.

How should a creative or service business price a project?

Ask the client's budget range upfront before quoting; this sets expectations and avoids guessing low when clients are actually willing to spend much more.

How do you convince a client to spend more on a video project?

Connect the cost of the work to concrete value, such as calculating recruitment costs saved by an employer brand video versus per-hire recruiter fees, so the client sees the ROI rather than just being told they 'need' it.

How should you handle people who take your personal/business information out of context?

Set boundaries and don't feel obligated to fully explain or justify financial or business details; people will often misapply isolated facts (like one good month's revenue) without the full context, so it's fine to speak broadly and keep some things private.

Should I invest in medical marijuana companies?

Favor companies that actually turn a profit rather than speculative growth-stage companies; some marijuana companies have lost huge sums (e.g. $100 million) despite industry hype, so there's a risk of big loss alongside potential big reward.

How do you decide whether to take on a business opportunity or client that feels ethically questionable?

Evaluate whether you'd be comfortable publicly associating your name with the work; if you'd be embarrassed or ashamed for people to know you made it, that's a sign it doesn't align with your values and you should decline, even if it's lucrative.

How do you build a location-independent or lifestyle-driven business?

Question inherited assumptions about what a 'real' business needs (big office, big server, certain gear) and instead design the business around the lifestyle you actually want, rather than over-committing to overheads that lock you in before you know if that's what you want.

What should you expect when selling secondhand items online?

Be prepared for time-consuming, sometimes 'dumb' conversations with buyers (like being asked where a well-known suburb is, or being chased for months over a missing remote or screw); it's part of the process of selling online.

How should you think about your worth and salary as an employee or freelancer?

Your worth is set by how much someone needs what you do; a salary functions like an insurance policy where an employer pays less than your billable rate in exchange for guaranteeing steady income and absorbing business risk, so chasing more pay without being willing to leave misunderstands the transaction.