Episode Overview

In this episode of The CTO Show with Mehmet, Andy Cwik—co-founder and CEO of Hubub—shares his lessons from three startups, including the painful failures and meaningful wins. From crashing his first startup to exiting a telehealth company, Andy now leads Hubub, a SaaS platform that automates client entertainment for B2B teams.

He opens up about what truly makes a startup successful (hint: it’s not the idea), how AI fits into real business workflows, why network effects matter more than ever, and how he’s using his time to mentor founders and advocate for mental health reform through a personal documentary project.

💡 Key Takeaways

• Execution outweighs the idea: Why founders often get stuck at ideation.

• Building defensibility through network effects and switching costs.

• How to pitch enterprise tools to decision-makers, not just users.

• Why most AI startups are chasing buzzwords—and what actually works.

• The evolution of startup ecosystems beyond Silicon Valley.

• A rare look into Andy’s advocacy for mental health reform in the justice system.

🎧 What You’ll Learn

• The origin story behind Hubub and its 13-year evolution

• How to move from “paper napkin” idea to product with traction

• Strategic use cases of AI in early-stage SaaS

• How to validate pain points and avoid marketplace traps

• Navigating risk aversion in startup hubs like Chicago

• Why some founders should take the exit—and why others shouldn’t

👤 About the Guest

Andy Cwik is a seasoned entrepreneur and AI thought leader with a track record of building innovative businesses. As the Co-Founder and CEO of hubub, he is redefining business client entertainment through AI-driven digital concierge services, automating logistics from reservations to expense reporting. With over a decade of experience in tech-driven ventures, Andy has successfully founded and exited multiple companies, including a telehealth startup with peak annual revenues of $25 million and a data encryption firm.

Beyond hubub, Andy is a key figure in Chicago’s startup ecosystem, serving in leadership roles for the Founders Institute and Founders Network, where he mentors emerging entrepreneurs. He has raised over $5 million across his ventures and has spoken at leading AI and business events, including GenAI Collective and the Union League of Chicago Business Leaders Group. Passionate about AI’s capabilities and limitations, Andy brings unique insights into the evolving landscape of technology, work, and automation. His thought leadership challenges mainstream AI narratives, advocating for a balanced perspective on its future impact.

https://www.linkedin.com/in/andy-cwik

https://hubub.me/

Episode Highlights & Timestamps

00:01 – Andy’s startup journey: 3 ventures and one painful failure

04:00 – The aha moment that led to Hubub

08:00 – Why expense reporting is the hidden pain point no one talks about

10:30 – Building a two-sided marketplace with smart API integrations

13:00 – What startup founders get wrong about AI

17:30 – Network effects and why Groupon failed

23:00 – Defensibility: Your real moat in a world of clones

28:00 – How AI is reshaping VC workflows (and deal sourcing)

32:00 – Chicago vs. Silicon Valley: What founders should know

40:00 – When to exit and when to stay the course

47:00 – Andy’s work on a documentary about mental health and the justice system

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