Insiders React: Anthropic's Huge AI Copyright Win + Speech to Text Better Than Ever, Peter Thiel's Tech Dystopia

We’ve received a lot of questions from the last few episodes. It’s time Chris and Yaniv answer them! This Q&A episode they explore: When should you quit your day job to go all in on your startup? When should we raise? We have got advice from VCs to raise early before it gets complicated to show interest in our platform. I’m sitting on the fence whether we should raise it as it takes a bit of agility and liberty away from us but I understand the benefits that the network accelerators/ VCs could bring. What do you mean by “going global day one”? Can you identify a specific moment or experience that made you question your purpose in your professional career? How did it influence your path forward? Is it worth registering patents as a startup when you know you don’t have the financial capacity or the time to chase up potential infringements? Engineering and highly technical cultures are often hard to orientate towards customer impact and outcomes. How do you build a strong obsession with customers amongst highly technical organizations? I am slowly getting stagnant from the lens of learning and growth. There isn’t enough manpower due to cost management, and I am spending a lot of my time working on low value work. There is no clear progression and I have not gotten an increment though it’s been over a year. How do I initiate a conversation with my direct report on this topic again? We have chatted about this but there is still no clear direction. How do I bring this up again without appearing like all I care about is growth and increment Why do investors require an ESOP pool to be created that they are protected from being diluted by? Why is the dilution not shared for future hires, whose objective is to increase the value of all shareholders? Shouldn’t everyone be treated evenly from this dilution? How do you know when it’s time to pivot? And what’s a pivot? A complete change of direction or just a change in the business model that would slightly change the product and the way you approach sales? What are the real implications of a pivot for a startup and the founders? Thanks to Nan, Simon, Henry and anonymous submitters for your questions. *Get your question in for our next Q&A episode:* https://forms.gle/NZzgNWVLiFmwvFA2A  The Pact  Honour The Startup Podcast Pact! If you have listened to TSP and gotten value from it, please: Follow, rate, and review us in your listening app Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early-access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe    Follow us on YouTube Give us a public shout-out on LinkedIn or anywhere you have a social media following  Key links Follow us on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg  The Startup Podcast website: https://tsp.show  Learn more about Chris and Yaniv Work 1:1 with Chris: http://chrissaad.com/advisory/  Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/  Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

11 Loka 202335min

Are you lying to yourself? Are you really aiming for greatness? This week Chris and Yaniv dive deep into the psyche of startup founders. Discover the harsh truth that a lack of conviction in your vision can lead to self-sabotage, compromising your business through misalignment, poor decision-making, and lost credibility. Are you settling for "good enough," or are you pursuing greatness with unwavering faith in yourself? In this thought-provoking discussion, learn why being ruthlessly honest with yourself is the key to building a company of meaningful impact. Once your vision is lost, it's challenging to regain that magic. Now is the time to align your thinking and execution. Join us as we explore how pragmatic decisions driven by conviction can inspire your team to follow your lead passionately. Don't deceive yourself; pursue your vision with courage and alignment to create a company that leaves a lasting mark. The magic of success is within your grasp - are you ready to seize it? Tune in now and embark on a journey of self-discovery and greatness! The Pact  Honour The Startup Podcast Pact! If you have listened to TSP and gotten value from it, please: Follow, rate, and review us in your listening app Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early-access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe    Follow us on YouTube Give us a public shout-out on LinkedIn or anywhere you have a social media following  Key links Follow us on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg  Get your question in for our next Q&A episode: https://forms.gle/NZzgNWVLiFmwvFA2A The Startup Podcast website: https://tsp.show  Learn more about Chris and Yaniv Work 1:1 with Chris: http://chrissaad.com/advisory/  Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/  Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

4 Loka 202340min

Today is a very special episode. This week on The Startup Podcast, Chris and Yaniv are joined by Mike Filbey, founder of Pepper and former co-founder of ButcherBox. Mike's journey is nothing short of extraordinary. He catapulted ButcherBox to soaring heights, amassing over $500 million in revenue. Yet, beneath the glitz and glamour of startup success, lay a harrowing truth. Driven by relentless ambition, Mike pushed himself to the brink, working grueling hours to meet colossal growth targets. But success came at a grave cost – his health. Multiple trips to the ER, with no physical explanation, were the alarming wake-up call that his body and mind had paid the price of extreme stress and anxiety. In a gut-wrenching twist, Mike chose to walk away from ButcherBox, relinquishing equity for the sake of his well-being. But the battle didn't end there. Depression loomed in the aftermath, and it took three arduous years to rediscover his purpose. A process he is still working on today. Join us as we delve deep into the profound lessons from Mike's journey. Discover why money and success offer diminishing returns for happiness, and why seeking help and finding your "flow" activities are vital for your mental health. Listen closely for the warning signs of burnout – they might just save your life. This episode is a profound exploration of the human side of entrepreneurship, that could reshape your perspective on the startup world. This episode is not to be missed. Tune in now! The Pact  Honour The Startup Podcast Pact! If you have listened to TSP and gotten value from it, please: Follow, rate, and review us in your listening app Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early-access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe    Follow us on YouTube Give us a public shout-out on LinkedIn or anywhere you have a social media following  Key links Follow us on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg  Get your question in for our next Q&A episode: https://forms.gle/NZzgNWVLiFmwvFA2A The Startup Podcast website: https://tsp.show  Learn more about Chris and Yaniv Work 1:1 with Chris: http://chrissaad.com/advisory/  Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/  Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

27 Syys 202346min

Is monetization the secret sauce for startup success, or is it a treacherous highway to failure?  Monetization isn't just about making money; it's about proving your product's worth in the market. Chris and Yaniv unveil the perfect timing for startups to take the monetization plunge and why premature monetization can slam the brakes on growth. Early-stage founders, take note: Discover why proving product-market fit is your North Star. Timing is everything, and monetizing too soon can slam the brakes on your growth. It's not just about profits; it's about reinvesting wisely. Explore how to navigate the monetization maze, from charging the right customers to leveraging paywalls and mastering enterprise sales. Dive into the priorities that propel startups from product-market fit to profitability, each stage an essential chapter in your success story. Remember, this framework isn't one-size-fits-all; it's a compass for your unique startup journey. Don't miss this episode—use it as your roadmap to monetization success! The Pact  Honour The Startup Podcast Pact! If you have listened to TSP and gotten value from it, please: Follow, rate, and review us in your listening app Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early-access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe    Follow us on YouTube Give us a public shout-out on LinkedIn or anywhere you have a social media following  Key links Follow us on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg  Get your question in for our next Q&A episode: https://forms.gle/NZzgNWVLiFmwvFA2A The Startup Podcast website: https://tsp.show  Learn more about Chris and Yaniv Work 1:1 with Chris: http://chrissaad.com/advisory/  Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/  Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

20 Syys 202342min

Squads - they’re the “it” way to organise cross-functional teams at Silicon Valley-startups. So why do they often not work? Unravel the blueprint for achieving organizational excellence through effective squads. With squads, teams transform from mere projects to long-term mission owners. These cross-functional squads, comprised of diverse roles and skills, skillfully navigate the balance between self-management and alignment with company objectives. Leadership steps in as the guiding force, offering vital support for escalation and resourcing needs. Behind the scenes, functions like product and engineering ensure seamless consistency across squads, fostering collaboration and autonomy. Discover the financial heartbeat of these squads as they are funded based on their missions, igniting innovation and progress. In this episode, we demystify the true metrics of success: outcomes and objectives. Join us this week as Chris and Yaniv explore the evolution of teams into autonomous, accountable units, all with the guidance and backing of leadership. The Pact  Honour The Startup Podcast Pact! If you have listened to TSP and gotten value from it, please: Follow, rate, and review us in your listening app Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early-access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe    Follow us on YouTube Give us a public shout-out on LinkedIn or anywhere you have a social media following  Key links Follow us on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg  Get your question in for our next Q&A episode: https://forms.gle/NZzgNWVLiFmwvFA2A The Startup Podcast website: https://tsp.show  Learn more about Chris and Yaniv Work 1:1 with Chris: http://chrissaad.com/advisory/  Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/  Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

13 Syys 202335min

In a world where insider founders often seem to have the upper hand, what if being an outsider founder could become your secret weapon?  This week on The Startup Podcast, Chris and Yaniv dive deep into the intriguing journey of outsider founders – those who don't hail from traditional backgrounds.  Join them as they unravel the strategies and insights that can transform your perceived disadvantages into strengths. Discover how understanding insider jargon and metrics can help you communicate effectively with investors and vital partners.  This week, they emphasize the power of seeking advice and making insiders your allies in the journey to success. And don't miss the exclusive on how accelerators can supercharge or destroy your growth and credibility.  But that's not all! They also explore the art of networking and the immense value of authenticity in forging lasting professional relationships.  Tune in and learn how to harness your scrappiness and resourcefulness, turning outsider status into your secret weapon for startup success!  The Pact  Honour The Startup Podcast Pact! If you have listened to TSP and gotten value from it, please: Follow, rate, and review us in your listening app Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early-access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe    Follow us on YouTube Give us a public shout-out on LinkedIn or anywhere you have a social media following  Key links Follow us on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg  Get your question in for our next Q&A episode: https://forms.gle/NZzgNWVLiFmwvFA2A The Startup Podcast website: https://tsp.show  Learn more about Chris and Yaniv Work 1:1 with Chris: http://chrissaad.com/advisory/  Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/  Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

6 Syys 202336min

There’s no denying it. No matter how good your product or team is, the startup will make or break because of the founder. Most founders learn this during their startup journey and actively pursue everything they can to make sure they can be the best founders possible. But in doing so, fall into the hidden traps and paradoxically become the founders they’ve tried so hard to avoid being. What are these founder traits that you should avoid at all cost? Chris is back and he rejoins Yaniv to explore the 7 Founder Archetypes Destined To Destroy Their Own Companies. With an analysis of their strengths and pitfalls, this exploration into the inner workings of startup visionaries is bound to captivate anyone fascinated by the clash of ego, ambition, and innovation. The 7 Founder Archetypes: 🪄 The Showman. 🍆 The Sex Addict. 👶 The Baby Elon. 👩‍💼 The Grown-Up. 🚁 The Helicopter Parent. 🎐 The Weathervane. ❓ The Memento Guy. The Pact  Honour The Startup Podcast Pact! If you have listened to TSP and gotten value from it, please: Follow, rate, and review us in your listening app Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early-access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe    Follow us on YouTube Give us a public shout-out on LinkedIn or anywhere you have a social media following  Key links Follow us on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg  Get your question in for our next Q&A episode: https://forms.gle/NZzgNWVLiFmwvFA2A The Startup Podcast website: https://tsp.show  Learn more about Chris and Yaniv Work 1:1 with Chris: http://chrissaad.com/advisory/  Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/  Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

30 Elo 202348min

Being a founder is incredibly difficult. There’s no denying that.  As a startup founder, the fate of the company rests on your shoulders. There’s little wonder you’re stressed. For the sake of the company, you must develop skills and techniques to look after yourself! With Chris unavailable as he continues his European adventures, Yaniv explores his 5 Rules of Staying Sane As A Founder. Curious about the art of balancing ambition and well-being? Eager to glean insights from a co-founder's perspective on steering the startup ship through uncharted waters? Watch as Yaniv peels back the layers of startup life, his personal anecdotes, invaluable tips and tricks for preserving your sanity in the exhilarating world of innovation and disruption. Yaniv’s 5 Rules of Staying Sane As A Founder: Rule 1: Keep your eye on the ball Rule 2: Observe the Stockdale Paradox Rule 3: Care a lot, but not too much Rule 4: Don’t try to do it alone, lean on others Rule 5: Prioritise staying in the game over winning the game The Pact  Honour The Startup Podcast Pact! If you have listened to TSP and gotten value from it, please: Follow, rate, and review us in your listening app Subscribe to the TSP Mailing List to gain access to exclusive newsletter-only content and early-access to information on upcoming episodes: https://thestartuppodcast.beehiiv.com/subscribe    Follow us on YouTube Give us a public shout-out on LinkedIn or anywhere you have a social media following  Key links Follow us on YouTube for full-video episodes: https://www.youtube.com/channel/UCNjm1MTdjysRRV07fSf0yGg  Get your question in for our next Q&A episode: https://forms.gle/NZzgNWVLiFmwvFA2A The Startup Podcast website: https://tsp.show  Learn more about Chris and Yaniv Work 1:1 with Chris: http://chrissaad.com/advisory/  Follow Chris on Linkedin: https://www.linkedin.com/in/chrissaad/  Follow Yaniv on Linkedin: https://www.linkedin.com/in/ybernstein/

23 Elo 202327min