DO AS I SAY

Buy my game!

I create a game from the ground up specifically for founders 🤯 it's called Pitch Please and I genuinely love playing it!

Prepare to hustle your way to the top in this cutthroat pitching showdown. Convince, charm, and con your way into the hearts and wallets of your competitors. Get ready to play the ultimate game of selling your soul for success.

The game is simple. Each round, every player matches a customer card with a product card and pitches the most absurd business they can imagine. The funniest and unequivocally worst idea wins.

https://pitchpleasegame.com/

THE GUEST

Marc Washbourne is the founder and CEO of ReadyTech. A company he scaled from a small software development house to a $350M market cap. Marc originally came to Australia as a backpacker for 6 months, but 25 years later he is still here and he is still building one of Australia’s top public companies.

THE QUESTIONS

🔍 Is Entrepreneurship Over-Glorified?

Media often portrays entrepreneurship as glamorous and heroic, but the reality is a relentless grind. While it can offer purpose and meaning to the right people, it’s not the best path for everyone.

💡 Handling Exhaustion Before a Product Launch

Facing a critical launch with limited runway and resources is one of the toughest challenges in startups. Cutting costs, seeking support, and focusing on key priorities can help maximise chances of success, even when energy is running low.

🔄 How to Test and Launch a Product Effectively

Starting small and testing core assumptions can validate if a product meets genuine market demand. This approach reduces risk and builds confidence while paving the way for scalable growth.

THE SHOW

DO AS I SAY is an advice show about the real problems in startups. Real startup people. Real startup problems.

Connect with Marc Washbourne:

LinkedIn: https://www.linkedin.com/in/marcwashbourne/ 

ReadyTech: https://www.readytech.com.au/ 

Connect with me:

YouTube: https://youtube.com/@joelditrapani

Spotify: https://open.spotify.com/show/5CVikUi4KcITAB4F15n5tZ

LinkedIn: https://www.linkedin.com/in/joel-ditrapani/

Calendar: https://cal.com/joelditrapani

Email: [email protected]

Website: https://joelditrapani.com/

Buy my game!

I create a game from the ground up specifically for founders 🤯 it's called Pitch Please and I genuinely love playing it!

Prepare to hustle your way to the top in this cutthroat pitching showdown. Convince, charm, and con your way into the hearts and wallets of your competitors. Get ready to play the ultimate game of selling your soul for success.

The game is simple. Each round, every player matches a customer card with a product card and pitches the most absurd business they can imagine. The funniest and unequivocally worst idea wins.

https://pitchpleasegame.com/

THE GUEST

Brad Moran is an ex-professional AFL player, a failed startup founder and more recently an insanely successful founder that took his startup from inception to a $200M exit in just 4 years. 

THE QUESTIONS

💡 Australia’s Startup Ecosystem Holds Founders Back

A lack of early-stage funding and a risk-averse culture makes Australia one of the toughest environments for startups. Perseverance and leveraging diverse angel investors can be game-changers.

🔄 Fear Drives Startup Success

Fear of failure, fueled by deep personal motivations, often builds the resilience required to endure the brutal realities of the business world. Success often belongs to those willing to risk everything and keep going despite setbacks.

THE SHOW

DO AS I SAY is an advice show about the real problems in startups. Real startup people. Real startup problems.

Connect with Brad Moran:

LinkedIn: https://www.linkedin.com/in/bradmoran/ 

Twitter/X: https://x.com/brad_noq 

Rocketship Advisory: https://www.rocketshipadvisory.com/ 

Connect with me:

YouTube: https://youtube.com/@joelditrapani

Spotify: https://open.spotify.com/show/5CVikUi4KcITAB4F15n5tZ

LinkedIn: https://www.linkedin.com/in/joel-ditrapani/

Calendar: https://cal.com/joelditrapani

Email: [email protected]

Website: https://joelditrapani.com/

Buy my game!

I create a game from the ground up specifically for founders 🤯 it's called Pitch Please and I genuinely love playing it!

Prepare to hustle your way to the top in this cutthroat pitching showdown. Convince, charm, and con your way into the hearts and wallets of your competitors. Get ready to play the ultimate game of selling your soul for success.

The game is simple. Each round, every player matches a customer card with a product card and pitches the most absurd business they can imagine. The funniest and unequivocally worst idea wins.

https://pitchpleasegame.com/

THE GUEST

Cat Macnaughtan is the creator of the Getting Lost game (a real life adventure game) and has sold over 200k copies!

THE QUESTIONS

🔍 I Want to Make My Board Game Into a Real Product. Where Do I Start?

To launch your game, focus on creating a minimum viable product that’s good enough to attract attention without over-investing upfront. Print a small batch, even if the per-unit cost is high, to gauge demand and collect feedback. It’s better to lose money on a small run than to overproduce and get stuck with stock no one wants.

💡 How Can I Get a Distributor?

Distributors take a big chunk of your revenue—up to 65% of your product’s retail price. When you are starting out, focus on direct-to-consumer sales through your website, trade shows, or social media. You’ll keep more profit and retain control of your brand’s story, which is critical for unique products and actually gives you leverage when you do speak with distributors later.

THE SHOW

DO AS I SAY is an advice show about the real problems in startups. Real startup people. Real startup problems.

Connect with Cat Macnaughtan:

LinkedIn: https://www.linkedin.com/in/cat-macnaughtan-55b65519/ 

Getting Lost: https://gettinglost.co.nz/ 

Connect with me:

YouTube: https://youtube.com/@joelditrapani

Spotify: https://open.spotify.com/show/5CVikUi4KcITAB4F15n5tZ

LinkedIn: https://www.linkedin.com/in/joel-ditrapani/

Calendar: https://cal.com/joelditrapani

Email: [email protected]

Website: https://joelditrapani.com/

Buy my game! I create a game from the ground up specifically for founders 🤯 it's called Pitch Please and I genuinely love playing it!

Prepare to hustle your way to the top in this cutthroat pitching showdown. Convince, charm, and con your way into the hearts and wallets of your competitors. Get ready to play the ultimate game of selling your soul for success.

The game is simple. Each round, every player matches a customer card with a product card and pitches the most absurd business they can imagine. The funniest and unequivocally worst idea wins.

https://pitchpleasegame.com/

THE GUEST

Wiz, famously known as Nadav Weizman, is the co-founder and former CEO of Cardinal, an AI-driven feature backlog solution that ties customer feedback, CRM data, and task management into actionable product strategies. After a successful journey through Y Combinator and rapid growth, Cardinal was acquired by Miro, where Wiz now serves as VP of Product, focusing on insights and innovation.

THE QUESTIONS

🔍 When Is an MVP Ready for Launch?

Releasing early allows for real feedback and iteration. Waiting for perfection often delays valuable insights and risks missing the mark on solving actual pain points.

💡 How to Break Free from Analysis Paralysis?

Focus on identifying clear customer pain points by speaking to potential users. Validate problems and solutions through direct conversations instead of overthinking or delaying decisions.

🔄 What Drives Startup Success?

Customer validation is critical. Reaching out to as many users as possible helps refine product-market fit, avoid missteps, and build solutions with real impact.

THE SHOW

DO AS I SAY is an advice show about the real problems in startups. Real startup people. Real startup problems.

Connect with Nadav Weizmann:

LinkedIn: https://www.linkedin.com/in/nadavwiz/ 

Twitter/X: https://x.com/nadavwiz 

Cardinal: https://cardinalapp.io/ 

Connect with me:

YouTube: https://youtube.com/@joelditrapani

Spotify: https://open.spotify.com/show/5CVikUi4KcITAB4F15n5tZ

LinkedIn: https://www.linkedin.com/in/joel-ditrapani/

Calendar: https://cal.com/joelditrapani

Email: [email protected]

Website: https://joelditrapani.com/

Buy my game!

I create a game from the ground up specifically for founders 🤯 it's called Pitch Please and I genuinely love playing it!

Prepare to hustle your way to the top in this cutthroat pitching showdown. Convince, charm, and con your way into the hearts and wallets of your competitors. Get ready to play the ultimate game of selling your soul for success.

The game is simple. Each round, every player matches a customer card with a product card and pitches the most absurd business they can imagine. The funniest and unequivocally worst idea wins.

https://pitchpleasegame.com/

THE GUEST

Cate Diaz is the founder of Market Chemistry, where she connects innovative founders with their best-match investors. Market Chemistry thrives on the belief that every startup’s ecosystem is unique, requiring a tailored set of investment partners. With a strong focus on relationship marketing, Cate helps founders navigate all types of funding rounds, from crowdfunding to angel investments and VC funding.

THE QUESTIONS

🔍 Why Is Crowdfunding So Polarising?

Crowdfunding is often misunderstood, with many founders facing skepticism or outright backlash. Cate explains how modern platforms have addressed key challenges and why blended funding rounds are changing the game.

💡 How Do You Build Relationships Before Raising?

Slinging pitch decks without connections rarely works. Cate shares tactical advice on building strong relationships with investors—before you’re ready to raise.

🔄 When Is It Too Early to Raise?

Founders often rush into fundraising, but timing is critical. Cate breaks down how to determine when you’re truly ready to seek outside capital.

THE SHOW

DO AS I SAY is an advice show about the real problems in startups. Real startup people. Real startup problems.

Connect with Cate Diaz

LinkedIn: https://www.linkedin.com/in/catediaz/

Market Chemistry: https://www.mktchemistry.com/

Connect with Joel Di Trapani:

YouTube: https://youtube.com/@joelditrapani

Spotify: https://open.spotify.com/show/5CVikUi4KcITAB4F15n5tZ

LinkedIn: https://www.linkedin.com/in/joel-ditrapani/

Calendar: https://cal.com/joelditrapani

Email: [email protected]

Website: https://joelditrapani.com/

Buy my game! I create a game from the ground up specifically for founders 🤯 it's called Pitch Please and I genuinely love playing it!

Prepare to hustle your way to the top in this cutthroat pitching showdown. Convince, charm, and con your way into the hearts and wallets of your competitors. Get ready to play the ultimate game of selling your soul for success.

The game is simple. Each round, every player matches a customer card with a product card and pitches the most absurd business they can imagine. The funniest and unequivocally worst idea wins.

https://pitchpleasegame.com/

THE GUEST

CJ Finley is the founder of ThriveOnLife, where he helps mission-driven startups scale their impact. With a background in industrial engineering, CJ now focuses on coaching, brand management, and guiding others to live happier, healthier, and wealthier lives. As a podcast host, speaker, and athlete, CJ is committed to pushing his limits and inspiring others to do the same. He also runs a thriving community of podcast hosts in Austin, which served as a key inspiration for this very podcast!

THE QUESTIONS

🔍 Stop Asking If Personal Branding Matters

Personal branding isn’t a nice-to-have; it’s the foundation of your future opportunities. The way you show up online and in-person dictates who you attract, what opportunities you unlock, and how much control you have over your life and career. If you’re ignoring it, you’re already falling behind.

💡 Niche Isn’t a Limitation—It’s the Gateway to Growth

Thinking niching down will box you in? Think again. Going deep on one problem and serving one audience creates infinite opportunities to master your craft and scale. Surface-level generalists get overlooked, but those who dig deep become indispensable.

🔄 Boundaries Create Freedom

Most people think boundaries limit potential. In reality, they’re the ultimate productivity hack. Clear constraints give you focus, prevent burnout, and create the clarity needed to achieve your goals faster. Without them, you’re just drifting aimlessly.

THE SHOW

DO AS I SAY is an advice show about the real problems in startups. Real startup people. Real startup problems.

Connect with CJ Finley

LinkedIn: https://www.linkedin.com/in/cjfinley

ThriveOnLife: https://thriveonlife.com

Connect with Joel Di Trapani:

YouTube: https://youtube.com/@joelditrapani

Spotify: https://open.spotify.com/show/5CVikUi4KcITAB4F15n5tZ

LinkedIn: https://www.linkedin.com/in/joel-ditrapani/

Calendar: https://cal.com/joelditrapani

Email: [email protected]

Website: https://joelditrapani.com/

Buy my game! I create a game from the ground up specifically for founders 🤯 it's called Pitch Please and I genuinely love playing it!

Prepare to hustle your way to the top in this cutthroat pitching showdown. Convince, charm, and con your way into the hearts and wallets of your competitors. Get ready to play the ultimate game of selling your soul for success.

The game is simple. Each round, every player matches a customer card with a product card and pitches the most absurd business they can imagine. The funniest and unequivocally worst idea wins.

https://pitchpleasegame.com/

THE GUEST

Cherie Werner is at the heart of Austin’s vibrant startup scene. As co-founder and community organizer of Fiesta, one of Austin’s largest networking events, she creates connections that span founders, investors, and newcomers alike. Cherie also serves as the Chief Kindness Officer at Koya Innovations, a startup focused on retaining key talent with kindness. Renowned for her generosity, Cherie exemplifies what it means to nurture authentic relationships.

THE QUESTIONS

🔍 How to network and keep relationships

Introverted? Networking can still work for you. Start by viewing each interaction as a chance to help others, and always follow up. Taking notes on people you meet helps make those follow-ups meaningful and memorable.

💡 Should I stay in a big city or move back home?

Staying in a big city can be tough, but it’s worth the effort. Build connections by consistently attending events, following up with interesting people, and even hosting your own gatherings to create your own community.

🔄 Red flags in startup culture

High turnover and poor communication aren’t just annoyances—they’re often signs of deeper cultural issues. Look for these clues, ask direct questions, and always trust your gut when assessing a company’s work environment.

THE SHOW

DO AS I SAY is an advice show about the real problems in startups. Real startup people. Real startup problems.

Connect with Cherie Werner:

LinkedIn: https://www.linkedin.com/in/cherie-werner/ 

FIESTA: https://www.fiesta.community/

Connect with Joel Di Trapani:

YouTube: https://youtube.com/@joelditrapani

Spotify: https://open.spotify.com/show/5CVikUi4KcITAB4F15n5tZ

LinkedIn: https://www.linkedin.com/in/joel-ditrapani/

Calendar: https://cal.com/joelditrapani

Email: [email protected]

Website: https://joelditrapani.com/

Buy my game! I create a game from the ground up specifically for founders 🤯 it's called Pitch Please and I genuinely love playing it!

Prepare to hustle your way to the top in this cutthroat pitching showdown. Convince, charm, and con your way into the hearts and wallets of your competitors. Get ready to play the ultimate game of selling your soul for success.

The game is simple. Each round, every player matches a customer card with a product card and pitches the most absurd business they can imagine. The funniest and unequivocally worst idea wins.

https://pitchpleasegame.com

THE GUEST

Jamie Fitch is the co-founder of OnlineMedEd, a company revolutionizing healthcare education by improving outcomes for medical students, faculty, and patients. As CEO, Jamie scaled OnlineMedEd’s education, technology, and operations for over a decade, raising more than $35M and impacting over 1 million students across 191 countries. Beyond OnlineMedEd, Jamie invested in nearly 40 companies and serves as an advisor, investor, and board member across healthcare, education, and marketing technology industries. 

THE QUESTIONS

🔍 How do entrepreneurs manage distractions and stay focused?To manage distractions effectively, it’s crucial to create systems like time-blocking and building personal resilience. Limit access to distractions by structuring your workspace and day intentionally, and focus on high-priority tasks by reviewing key projects each week.

💡 How can founders stay in control without micromanaging?Founders need to balance empathy with decisive action. Set clear areas of responsibility for each team member, listen to input, but make decisions based on a structured framework that combines user insights, expert advice, team feedback, and data.

🔄 How do you overcome analysis paralysis as a startup?The best way to beat analysis paralysis is to start small and test quickly. Validate your ideas early by gathering customer feedback and only move forward once you’ve proven that your direction is right, minimizing unnecessary risks.

THE SHOW

DO AS I SAY is an advice show about the real problems in startups.

Connect with Jamie Fitch:

LinkedIn: https://www.linkedin.com/in/jamiefitch/

Connect with Joel Di Trapani:

YouTube: https://youtube.com/@joelditrapani

Spotify: https://open.spotify.com/show/5CVikUi4KcITAB4F15n5tZ

LinkedIn: https://www.linkedin.com/in/joel-ditrapani/

Calendar: https://cal.com/joelditrapani

Email: [email protected]

Website: https://joelditrapani.com/

Buy my game! I create a game from the ground up specifically for founders 🤯 it's called Pitch Please and I genuinely love playing it!

Prepare to hustle your way to the top in this cutthroat pitching showdown. Convince, charm, and con your way into the hearts and wallets of your competitors. Get ready to play the ultimate game of selling your soul for success.

The game is simple. Each round, every player matches a customer card with a product card and pitches the most absurd business they can imagine. The funniest and unequivocally worst idea wins.

⁠https://pitchpleasegame.com⁠

THE GUEST

Umberto Anderle is the co-founder of HowdyGo, a platform that enables SaaS companies to build interactive product demos and share them with prospects, making the sales process smoother and more engaging. Before this, Umberto was the first product hire at Bibliu, a rapidly growing edtech company, where he self-taught his way to the head of product role, leading the team as the company scaled through multiple rounds of funding. With his incredible background, Umberto brings real experience to building product teams and managing growth in fast-paced environments.

THE QUESTIONS

🔍 How do I build and lead a product team while scaling?Start by aligning your product strategy with the company’s vision, ensuring everyone in the team understands it. Then, repeat it so often that it becomes second nature, helping everyone stay focused on the same goals.

💡 How do I get over the fear of launching a product?Failure is part of the process—what matters is launching, learning, and iterating. Your first version won’t be perfect, but getting real user feedback is what will make it great.

🔄 Why is estimating product development timelines so hard?It’s difficult because large projects hide complexity, but breaking them into smaller chunks makes estimation much easier. Stick to timelines by cutting scope, not stretching time, and focus on delivering value incrementally.

THE SHOW

DO AS I SAY is an advice show about the real problems in startups.

Connect with Umberto Anderle:

LinkedIn: https://www.linkedin.com/in/uanderle/

HowdyGo: https://www.howdygo.com/

Connect with Joel Di Trapani:

YouTube: https://youtube.com/@joelditrapani

Spotify: https://open.spotify.com/show/5CVikUi4KcITAB4F15n5tZ

LinkedIn: https://www.linkedin.com/in/joel-ditrapani/

Calendar: https://cal.com/joelditrapani

Email: [email protected]

Website: https://joelditrapani.com/

Buy my game! I create a game from the ground up specifically for founders 🤯 it's called Pitch Please and I genuinely love playing it!

Prepare to hustle your way to the top in this cutthroat pitching showdown. Convince, charm, and con your way into the hearts and wallets of your competitors. Get ready to play the ultimate game of selling your soul for success.

The game is simple. Each round, every player matches a customer card with a product card and pitches the most absurd business they can imagine. The funniest and unequivocally worst idea wins.

⁠https://pitchpleasegame.com⁠

THE GUEST

Charlie Ward is a remarkable solopreneur who excels at building in public and generously shares his journey with others. As the founder and community lead at Indie London, the UK’s top Indie Hackers community, Charlie has created a vibrant space where indie hackers and solopreneurs can connect both online and through in-person events. Additionally, he founded Ramen Club, a startup dedicated to providing community, content, and tools for bootstrapped founders, and Studio Ramen, a design studio focused on product development, community building, and AI. Charlie is an expert at nurturing communities and establishing profitable businesses from day one.

THE QUESTIONS

🔍 How can solo entrepreneurs avoid loneliness?Solo entrepreneurship can be isolating, and many miss the camaraderie of having teammates. In this episode, Charlie shares valuable advice on how solo entrepreneurs can stay connected and engaged, from joining online communities to starting their own meetups, and even hosting events tailored to their needs.

💡 Why choose bootstrapping over venture capital?Bootstrapping offers founders more control over their business and its growth trajectory. Charlie discusses why some entrepreneurs opt for bootstrapping instead of raising venture capital, highlighting the importance of autonomy, long-term sustainability, and personal alignment with business goals.

🔄 Finding startup ideas without networkingFor those who find networking challenging, discovering new problems to solve can seem daunting. Charlie and Joel explore alternative methods for identifying business opportunities, from leveraging competitive markets to repurposing successful ideas in new contexts, all without needing to network extensively.

THE SHOW

DO AS I SAY is an advice show about tackling real startup challenges. 

Connect with Charlie Ward:

LinkedIn: https://www.linkedin.com/in/charlierward/

Ramen Club: https://ramenclub.so

Connect with Joel Di Trapani:

YouTube: https://youtube.com/@joelditrapani

Spotify: https://open.spotify.com/show/5CVikUi4KcITAB4F15n5tZ

LinkedIn: https://www.linkedin.com/in/joel-ditrapani/

Calendar: https://cal.com/joelditrapani

Email: [email protected]

Website: https://joelditrapani.com/