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/

THE GUEST

Cristo Pajust is a serial entrepreneur and digital nomad who has built an impressive career across the globe. From launching a startup through Techstars and selling it, to leading the expansion of major companies like Groupon, Revolut, and Uber, Cristo’s experience in the startup world is unparalleled. He’s also known for launching Food Panda in Asia, making it a market leader in food ordering. Now, Cristo spends his time moving from country to country working on his latest venture aimed at helping digital nomads explore Africa.

THE QUESTIONS

🔍 Getting Feedback for a B2B ProductFinding users to test your product can be a challenge, especially in the B2B space. Cristo and Joel dive deep into strategies to get valuable feedback, emphasizing the importance of relentless cold outreach and the need to identify your target audience more narrowly.

💡 Dealing with a Security VulnerabilityWhat would you do if a friend found a security flaw in your product but demanded payment to reveal it? Cristo shares insights on handling such tricky situations, including the importance of transparency with your users and alternative ways to identify and fix vulnerabilities.

🔄 Finding the Right Co-FounderFinding a technical co-founder is often one of the biggest hurdles for non-technical founders. Cristo discusses how to make your startup attractive to potential co-founders, why you should lower your standards initially, and how to leverage your network effectively.

THE SHOW

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

Connect with Cristo PajustLinkedIn: https://www.linkedin.com/in/cristopajust/

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/

THE GUEST

Janine Allis is a renowned entrepreneur, best known as the founder of Boost Juice, a global chain with nearly 700 stores in 12 countries. A regular on Australia's "Shark Tank," Janine has become a leading voice in business, offering her expertise in scaling companies and empowering the next generation of entrepreneurs. Beyond her business ventures, she is a bestselling author and a fierce advocate for health and well-being.

THE QUESTIONS🔍

Navigating Burnout While Building a Business

Entrepreneurial burnout is real, and Janine shares her insights on how to navigate it. Whether it’s stepping away for a mental reset or learning to manage stress effectively, she provides practical advice on maintaining balance while scaling a business.

💡 The Secret to Scaling a Food & Beverage Empire

Janine dives into the specifics of what it takes to build a successful food and beverage brand. From ensuring product quality to obsessing over customer service, she highlights the key factors that differentiate thriving businesses from those that falter.

🔄 Building an Authentic Brand FollowingHow do you create a brand that people love? Janine explains the importance of focusing on one customer at a time, being authentic, and learning from every interaction. Her approach to building Boost Juice into a beloved brand is a masterclass in marketing and customer loyalty.

THE SHOW

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

Connect with Janine Allis

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

Twitter: https://twitter.com/Janineboost

Boost: https://www.boostjuice.com.au/

Connect with Joel DiTrapani

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/

THE GUEST

David Shein is a seasoned entrepreneur and venture capitalist, best known for founding Australia’s first unicorn, Com Tech Communications. Currently a partner at OIF Ventures, David has a wealth of experience in building and scaling businesses. He’s also an author, with his book "The Dumbest Guy at the Table," offering insights into his journey and the principles that have guided him.

THE QUESTIONS🔍

How Do Investors Evaluate Startups?

David breaks down the "5 T's" of startup success: Team, TAM, Traction, Timing, and Terms. These five key factors are crucial for securing investment and scaling your business effectively. Each one is a vital checkpoint that can make or break your startup's potential.

💡 The Challenges of Raising Seed Capital

Raising your first round of investment isn’t just about having a great idea. David discusses why founders need to demonstrate exceptional founder energy, prove market potential, and be prepared for the rigorous due diligence that investors will conduct.

🔄 How to Find Like-Minded Friends and Mentors

Finding true friends and mentors as an entrepreneur can be tough. David shares his advice on focusing on the significant few rather than the insignificant many, and how common interests can lead to meaningful, lasting relationships.

THE SHOW

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

Connect with David Shein:

LinkedIn: https://www.linkedin.com/in/david-shein-7039b413/

OIF Ventures: https://www.oifventures.com.au/

Book: https://amzn.asia/d/82s0REI

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/

THE GUEST

Ash Allison is an expert in company culture and team dynamics, currently serving as the VP of Operations & People at TRAILD. With an impressive background that spans consulting at Bain, practicing law (including helping an inmate off death row!), and leading People & Culture at Vygo, Ash brings a wealth of experience to the table. She's also an award-winning book club organiser and an aspiring author, all while being one of the kindest and most engaging people you'll ever meet.

THE QUESTIONS

🔍 How Do You Build a Remote Company Culture?

In a world where remote work is becoming the norm, how do you maintain a vibrant and cohesive company culture? Ash discusses the key elements of remote culture, from the importance of clear expectations and communication overkill to fostering social availability and structured relationships. Learn why culture in a remote setting must be intentional and consistently nurtured.

💡 Should You Fire Your First Developer?

Firing is never easy, especially when it involves your first hire. We dive into a listener's dilemma about whether to let go of their underperforming developer. Ash and Joel explore the importance of clear expectations, the role of effective management, and when it's time to part ways for the good of both the company and the individual.

🔄 What Does Company Culture Really Mean?

What exactly is company culture, and why does it matter? Ash and Joel break down this complex concept into something tangible, comparing culture to oxygen and glue—essential, yet often hard to define. They discuss how culture impacts every facet of a business and why it's crucial to establish it early on.

THE SHOW

DO AS I SAY is an advice show that tackles real startup challenges. 

Connect with Ash Allison:

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

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/

Bret Siers is the CEO & Co-founder at AdoptIQ, a startup that delivers your playbook to users exactly when, where, and how they need it. Bret is creating the "GPS of Software," and has spent over 27 years training and developing leaders, making him a leading expert in the training space. He is an entrepreneur, coach, educator, trainer, and father of four, dedicated to helping people from all backgrounds achieve their definition of success.

THE QUESTIONS🔍 How to Build Relationships with LeadershipIn a decentralized, remote working environment, Bret discusses the importance of taking initiative to engage with leadership. He offers practical advice on how to foster those relationships, whether it’s through volunteering for side projects or simply finding ways to be seen and recognized for your contributions.

💡 What Makes Onboarding Processes Successful?We dive deep into the critical elements of successful onboarding. Bret shares insights on how companies like Google and Slack have nailed their onboarding processes by focusing on what truly delivers value to users. He emphasizes the importance of understanding the user journey and designing onboarding processes that facilitate key actions that lead to user retention and satisfaction.

🔄 The Dynamics Between Product and Customer Success TeamsBret and I explore the often complex relationship between Product and Customer Success (CS) teams. We discuss the importance of aligning goals, building trust, and ensuring open communication to create harmony between these crucial teams. Bret shares his thoughts on how the right collaboration can drive product success and enhance customer satisfaction.

THE SHOW

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

Connect with Bret Siers

Connect with Joel Di Trapani:

THE GUEST

Josh Pugh, also known as America Josh, is a community builder, digital marketing expert, and founder of Fortnight Digital, a consultancy based in New York City. Originally from South Australia, Josh has become an essential resource for expats moving to the U.S. through his platform, America Josh. His website offers high-quality, accessible information on everything from visa issues to finding a place to live, making the daunting process of relocating to America a little easier.

THE QUESTIONS

🔍 Why is Moving to America So Hard?Josh delves into the complexities of the U.S. immigration system, sharing his own experiences and offering insights on the challenges faced by newcomers, including the bureaucratic hurdles that can make the process feel nearly impossible.

💡 What Should You Do Before Moving?Preparation is key. Josh emphasizes the importance of early planning, from securing the right visa to understanding the American credit system, and offers practical advice on the steps you should take before making the move.

🔄 How Do You Make Life in the U.S. Work for You?Adjusting to life in the U.S. can take time. Josh discusses the cultural differences between states, the importance of setting realistic expectations, and how to find your footing in a new environment.

THE SHOW

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

Connect with Josh Pugh:

Connect with Joel Di Trapani:

THE GUEST

Anna Naumova is a seasoned product manager and the founder of Prodcast, a company dedicated to helping immigrants navigate their professional journeys in new countries. With a wealth of experience from working at top tech companies, including Apple, Anna shares her insights into the unique challenges faced by those new to the U.S. and how they can overcome them.

THE QUESTIONS

🔍 Do Startups Really Need Product Managers?Anna offers a surprising take on whether small startups truly need product managers. She explains why in the early stages, the founder might be the best person to handle product management duties and how the role often evolves as the company grows.

💡 Breaking into Product ManagementFor those looking to transition into product management, Anna breaks down the essential skills needed, from understanding the business side to mastering user needs. She emphasizes the importance of gaining hands-on experience and developing a product mindset.

🔄 Is Moving to the U.S. Worth It for Startups?Anna and Joel discuss the pros and cons of relocating to the U.S. for startup founders, weighing the benefits of the U.S. market against the high cost of living. They explore alternative strategies for gaining U.S. market access without the need to move.

THE SHOW

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

Connect with Anna Naumova

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

Website: https://annanaumova.com/ 

Youtube: https://www.youtube.com/@prodcastUS

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/

THE GUEST

Laura Tacho is the CTO  at DX, an insights platform for measuring and improving developer productivity. Laura is also one of the greatest leadership coaches I have ever met, and I had the privilege of working with her for years. When I started working with Laura, I had zero engineers and no idea what I was doing in product at all, and step by step, she built me and my entire team up from scratch. Because of Laura's help, we went from a bit of a disaster for a product team to a genuinely world-class product team I am incredibly proud of! I talk about the benefits of coaching on this podcast constantly, and I'm always talking about Laura when I do because working with someone like Laura can fundamentally change your business. On top of this, Laura writes about developer teams in her newsletter and on Twitter, and it's opinionated, honest, and genuinely good.

THE SHOW

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

Laura Tacho

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

Twitter/X: ⁠⁠⁠⁠https://twitter.com/rhein_wein

Website: https://lauratacho.com/

My links

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]⁠⁠

Other stuff: https://joelditrapani.com/