The Thrills and Challenges of Pursuing Startup Dreams

👉🏼 About the Guest:

John Andrew Entwistle is the founder and CEO of Wander, a startup revolutionizing short-term rental space! So far John and his team have raised over $27M in funding and are on a mission to deliver high-quality experiences for travelers. John was previously a Thiel Fellow and co-founder of Coder, a venture-backed startup that is making strides in moving the development workstation to the cloud, amplifying security and productivity for software development teams.

His passion for start-ups and dedication to transforming industries brought him recognition as one of the "Insider 30 Rising Stars of Real Estate” in 2022 by Business Insider and his innovative work at Code led him to be featured in Forbes "30 under 30" in 2019.

👉🏼 About the Host:

Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 22,000 using give-first principles and creating high-value content. Currently, he is the Head of Community + Brand at Threado, building a side project called GuestLab, and runs a newsletter called YC Founder Stories alongside hosting this podcast.

👉🏼 Sponsor Corner:

Shoutout to Acquire.com for being the first sponsor of The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you're looking to wind down your business and cash in some of your founder chips, check them out - https://try.acquire.com/sharath/

👉🏼 Description:

Tune in as Sharath and John discuss focussing on your own priorities in life, making difficult decisions, and the journey to a brand new startup in a new industry.

👉🏼 Timestamps:

• 00:00: Episode Highlight
• 01:15: Shoutout to Acquire.com
• 03:51: Introduction to John
• 06:35: What is the transition from coding to real estate like?
• 09:45: How did 18-year-old John stay on track to build a company that raised $45M?
• 14:05: The dangers of overwork
• 16:25: How to handle life regrets
• 20:40: The various decision-making frameworks in John's life
• 26:23: Which decision was John 100% sure about?
• 31:49: The best ways to handle failure
• 42:25: How to restart a company from zero
• 47:30: The impact of the Thiel fellowship on John's life
• 51:38: A bet John took that changed people's lives
• 54:22: The biggest decision today that will impact John's life
• 57:09: The difficulties of working in real estate
• 1:01:30: How to convince investors to invest in your startup
• 1:05:55: Lessons learned while creating Wander
• 1:09:15: Handling the heavy lifting of making homes livable
• 1:15:55: The next dream for Wander
• 1:24:08: Outro and closing thoughts

👉🏼 Resources:

• "Courage is Calling: Fortune Favors the Brave" by Ryan Holiday: https://www.goodreads.com/en/book/show/58145670

👉🏼 Where to find John:

• Twitter: https://twitter.com/jaentwistle
• Instagram: https://www.instagram.com/jaentwistle/
• Linkedin: https://www.linkedin.com/in/jaentwistle

👉🏼 Where to find Sharath:

• Twitter: https://twitter.com/5harath
• YouTube: https://www.youtube.com/@5harath
• Website: https://5harath.com/
• Newsletter: https://5harath.substack.com/