Episode Overview

In this episode of The CTO Show with Mehmet, Andy Cwik—co-founder and CEO of Hubbub—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 Hubbub, 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 Hubbub 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 Hubbub

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

In this episode of The CTO Show, serial entrepreneur and podcast host Anthony Franco joins Mehmet to unpack how AI is fundamentally reshaping how businesses operate—beyond the hype. With six exits under his belt and decades of experience launching and scaling ventures, Anthony shares what it really takes to operationalize AI in today’s organizations and why the real disruption isn’t about job loss—it’s about organizational survival.

💡 What You’ll Learn

• Why most leaders still misunderstand what “AI transformation” really means

• The biggest mistake companies make when automating workflows

• How to rethink outdated systems like Agile and Six Sigma in the AI age

• Why agentic AI is less about replacing roles and more about rebuilding how work is done

• How founders can leverage AI for early-stage growth, product-market fit, and GTM

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🧠 Key Takeaways

• Don’t automate bad processes—simplify first, then apply AI

• Think like a gardener, not a factory manager: AI requires adaptability

• Founders need to master human-to-human connection more than ever

• Smaller teams will win, but collaboration still beats solo work

• The best time to exit is two years before you burn out

👤 About the Guest

Anthony Franco is a serial entrepreneur, founder of six companies, and host of the How to Founder podcast. He’s currently helping companies apply AI-first thinking to real-world operations through his work with OneReach and initiatives like AI First Principles and the WISER Methodology.

http://www.howtofounder.com/

https://linkedin.com/in/anthonyfranco/

⏱️ Episode Highlights

00:02 – Anthony’s journey and current projects

04:00 – What it means to “operationalize” AI

06:30 – AI First Principles and the WISER Methodology

11:00 – Why old frameworks like Agile are becoming obsolete

17:00 – Can this work for large enterprises?

20:00 – Is AI a threat to jobs or to companies?

25:00 – How founders should approach AI-powered ventures

30:00 – Building vs. selling: What founders forget

34:00 – Why a great product isn’t enough without distribution

39:00 – The story behind How to Founder

43:00 – Smaller teams, bigger outcomes

47:00 – Signs it’s time to exit

51:00 – Final thoughts on the startup mindset

In this episode of The CTO Show with Mehmet, we dive into the world of deep tech and hardware innovation with Faizan Ahmed, founder and CEO of Invensify. From solving his father’s insulin storage problem to building a patented solid-state cooling module, Faizan walks us through the journey of reinventing refrigeration and building a product-as-a-service business in a legacy-driven industry.

🎯 Key Takeaways

• What solid-state cooling really is—and why it matters

• The surprising size of the pharma cold chain logistics market

• Why hardware innovation must be 10x better to be taken seriously

• How a Product-as-a-Service model creates defensibility

• Fundraising for deep tech: what works and what doesn’t

• Real-world sustainability beats greenwashing

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📚 What You’ll Learn

• How to identify deep tech opportunities from personal problems

• The trade-offs of designing hardware with no moving parts

• Why solid-state cooling is more sustainable and scalable than compressors

• What it takes to commercialize deep tech in a SaaS-obsessed world

• How to overcome industry resistance to innovation

👤 About the Guest

Faizan Ahmed is a second-time hardware founder with a background in electrical engineering and solid-state physics. Before Invensify, he exited a startup that built camera lens rain deflectors, and earlier contributed to a defense tech company acquired by the U.S. Air Force. Today, he leads Invensify in building energy-efficient, compressor-free cooling systems for healthcare and beyond.

https://www.invensify.com/

https://www.linkedin.com/in/faizan-ahmed-a720b411/

🕒 Episode Highlights & Timestamps

00:00 – Intro and guest welcome

01:30 – Faizan’s engineering background and past exits

03:55 – The insulin travel problem that sparked Invensify

05:30 – Cold chain logistics is a $6.2B market still using ice packs

06:45 – What is solid-state cooling? Tech foundations explained

10:00 – Efficiency, battery weight, and key trade-offs

12:30 – Designing lightweight, plug-and-play cooling systems

14:00 – Zero moving parts = low maintenance + high reliability

15:00 – Accidental sustainability: how climate impact became a bonus

17:00 – Key verticals: pharma, EV batteries, AI chips, data centers

21:00 – Product-as-a-Service: Why Faizan avoided hardware sales

24:30 – ESG regulations and sustainability tailwinds

28:00 – Manufacturing in Malaysia and global expansion plans

29:00 – Fundraising lessons from deep tech

31:00 – The importance of 10x differentiation in hardware

34:00 – Transferable skills from previous startups

36:00 – Will solid-state cooling replace traditional refrigeration?

39:00 – Faizan’s vision: Cooling fridges in off-grid areas

42:00 – Which is harder—tech innovation or mindset shift?

47:00 – Final advice to founders