Episode 54

Lessons from a Paperboy who built a $13M Company! | James Wahba - E54

Published on: 11th March, 2025

**From delivering newspapers in 4th grade to raising millions for real estate and co-founding a thriving co-working space—James Wahba’s journey is nothing short of inspiring.**🚀

In this episode of Funds & Founders, James shares:

✅ How his childhood paper route taught him business fundamentals 📈

✅ Raising $13M at 25 for real estate development 🏗️

✅ Building one of NYC’s most iconic co-working spaces 🚀

✅ Lessons from working alongside startups like Uber, Instacart, Stripe, Airbnb

✅ Why co-founder conflicts are one of the biggest startup killers 😨

If you’re an aspiring entrepreneur, real estate investor, or startup founder, you don’t want to miss this one!

Timestamps:

00:00 - Welcome to Funds & Founders!

00:20 - James Waba’s entrepreneurial journey begins

01:14 - Growing up in Connecticut and learning business from a paper route

02:18 - The business lessons from his first job 📜

03:14 - Learning about customer retention and revenue at a young age

05:10 - From paper route to film school & shooting concerts 🎥

06:35 - Starting one of the first online streaming sites (before YouTube!)

07:54 - Partnering with Microsoft & early struggles of internet startups 💻

09:12 - Raising funds & the early days of NYC tech

12:22 - Competing in the pre-YouTube era—how streaming was built back then

16:04 - Shutting down the startup and pivoting to real estate development

17:08 - Converting industrial property to high-value waterfront real estate

19:52 - Raising $13M for a real estate project at 25

22:11 - The 2008 market crash hits—what happened next?

25:46 - Lessons learned: How to survive market crashes

28:49 - Bootstrapping vs. raising VC: What should startups do?

31:07 - The reality of investor expectations & startup funding

32:55 - Pivoting from real estate to co-working spaces 🏢

35:49 - How James built one of NYC’s top co-working spaces

39:32 - Uber, Instacart, and Airbnb worked here—what was it like?

41:14 - Why taking equity over cash would have been the best move

44:08 - The rise and fall of the co-working space model

46:50 - How to build a real, engaged community (not just a Slack group)

49:21 - Challenges of managing a co-working space & scaling it

51:34 - What James is building in Austin & his new boutique hotel project

54:45 - Rapid fire Q&A: Advice for founders, resources, and more

58:07 - Best books for entrepreneurs 📚

1:00:39 - What’s missing in the Austin startup ecosystem?

1:01:34 - Final thoughts & where to connect with James

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About the Podcast

Funds and Founders: Untold Journeys Behind Their Breakthroughs
Welcome to "Funds & Founders: Untold Journeys Behind Their Breakthroughs," where we dig deep into the stories of successful Austin founders. Instead of focusing on their successes though, we dive into their journeys, particularly the struggles and obstacles they had to overcome.

This weekly podcast is tailored for Austin founders navigating the early stages of their entrepreneurial journey and hosted by fellow Austinite Abhinav Sinha. Here’s what to expect by tuning into Funds & Founders:

🚀 Embark on a Journey to Success
Join Abhinav as he takes you behind the scenes, exploring the highs and lows of building a company. This isn't your typical success story – we dive into the failures, the struggles, and those pivotal breakthrough moments that define a founder's path.

🌟 Real Conversations, Real Insights
Abhinav's approach is refreshingly different. Rather than dwelling on success, he crafts casual conversations that unravel the untold stories. Identify the setbacks that helped them grow, the lessons learned from failures, and the breakthrough moments that fueled these founders.

🤔 Why Didn't They Quit? Learn and Apply.
At the heart of each episode, Abhinav delves into the 'why' behind the perseverance. Why didn't they throw in the towel during tough times? And, most importantly, how can you apply their insights to your own journey? Get ready to be inspired and equipped with practical takeaways for your entrepreneurial adventure.

🤝 Decoding Venture Capital
Ever wondered what goes on in the minds of Austin's venture capitalists? Abhinav sits down with local VCs to decode their criteria for investing in early-stage companies. Gain valuable insights into the world of venture capital, understand what investors look for, and appreciate the vital factor of founder-investor compatibility.

🎙️ Meet Your Host, Abhinav Sinha:
Abhinav's soft-spoken yet inquisitive style creates an intimate atmosphere, allowing guests to share their authentic stories. His genuine curiosity and insightful questions make each episode a captivating journey into the minds of Austin's most successful founders.

If you're a budding Austin entrepreneur seeking the inspiration and insight needed for building a successful company, "Funds & Founders" is your go-to podcast.