In this episode, Mehmet sits down with Andrew Ackerman, two-time founder, early-stage investor with 70+ investments, accelerator leader, entrepreneurship professor, and author of The Entrepreneur’s Odyssey.

Andrew shares hard-earned insights from running accelerator programs, investing across decades, and coaching founders at their most fragile moments. The conversation dives deep into why startups fail, what truly separates winning founders, how coachability beats ego, and why storytelling is more powerful than advice.

They also explore how AI is reshaping entrepreneurship, why the bar for founders keeps rising, and why building faster is no longer a competitive advantage on its own.

⸻

👤 About the Guest

Andrew Ackerman is a seasoned entrepreneur, investor, educator, and author.

• Two-time startup founder

• Investor in 70+ early-stage companies

• Former accelerator leader (DreamIt)

• Entrepreneurship professor

• Author of The Entrepreneur’s Odyssey: A Novel Approach to Startup Success

Andrew has spent decades working at the intersection of founders, investors, and large enterprises, giving him a rare inside view of what actually makes startups succeed or fail.

http://www.linkedin.com/in/andrewbackerman

⸻

🧠 Key Takeaways

• Startups fail due to broken links, not a single bad idea

• Coachability matters more than confidence or experience

• The best founders hold strong opinions loosely

• Storytelling drives action better than direct advice

• AI lowers the cost of building, but raises the bar for funding

• First-mover advantage is weak without a real moat

• Empathy is the hidden superpower behind great founders, salespeople, and storytellers

⸻

🎓 What You’ll Learn

• Why startups should be viewed as chains, not ropes

• How accelerators compress the learning curve for investors and founders

• How to spot coachable founders early

• Why experimentation beats gut instinct

• How to test ideas cheaply before building

• Why many founders hide in their comfort zone instead of doing the hard work

• How AI changes the “why now” question for startups

⸻

⏱️ Episode Highlights & Timestamps

00:00 – Introduction and Andrew’s background

03:00 – Why running an accelerator changes how you see startups

07:00 – Angel investing vs accelerator investing

10:00 – Startups as chains, not ropes

12:30 – Why startups fail in different ways

14:30 – The one trait that separates great founders

18:00 – Coachability, ego, and founder decision-making

22:00 – Can entrepreneurship really be taught?

25:00 – The “looking for money under the streetlight” founder trap

28:00 – Why storytelling beats direct advice

32:00 – SeatGeek origin story and early validation lessons

36:00 – Empathy as a core founder skill

40:00 – AI, hype, and what’s actually changing for startups

45:00 – Why the investor bar keeps rising

50:00 – Final advice for founders and investors

⸻

📚 Resources Mentioned

• The Entrepreneur’s Odyssey by Andrew Ackerman: https://www.amazon.com/Entrepreneurs-Odyssey-Approach-Startup-Success/dp/1032883545/ref=tmm_pap_swatch_0

• Andrew’s website: https://www.andrewbackerman.com/

In this episode of The CTO Show with Mehmet, I’m joined by Max Ivey, known as The Blind Blogger and a leading voice in digital accessibility.

Max shares his remarkable journey from growing up in a family-run carnival business to becoming an accessibility advisor helping companies rethink how they design products, websites, and AI tools. We go deep into why accessibility is not a legal checkbox but a business, UX, and growth advantage, and why most modern AI tools are still failing real users.

This conversation is a masterclass for founders, product leaders, designers, and executives who want to build inclusive, scalable, and future-proof products.

⸻

👤 About the Guest

Max Ivey is an accessibility expert, entrepreneur, speaker, and host of The Accessibility Advantage podcast. Blind since birth, Max brings decades of lived experience navigating technology, entrepreneurship, and digital products without sight.

He advises startups and enterprises on building truly accessible and usable products, helping them move beyond fear-driven compliance toward inclusive design that benefits all users.

⸻

🧠 Key Takeaways

• Accessibility improves UX for everyone, not just people with disabilities

• WCAG compliance alone does not guarantee usability

• Many AI tools are unintentionally scaling inaccessibility

• Inclusive design builds brand loyalty, trust, and advocacy

• Small companies can outcompete big players by embracing accessibility early

• Designing with a keyboard-first mindset changes everything

⸻

📚 What You’ll Learn in This Episode

• Why accessibility should be treated as a competitive advantage

• How blind and disabled users actually navigate digital products

• The hidden accessibility debt in AI-generated content

• Practical principles for accessible and inclusive product design

• The real business case behind accessibility, beyond legal risk

• How founders can avoid common UX mistakes that cost revenue

⸻

⏱️ Episode Highlights & Timestamps

00:00 – Introduction and welcome

02:10 – Max Ivey’s journey from carnival business to accessibility advocate

06:40 – Why Max chose to be open about his disability online

10:30 – Teaching himself HTML to get online

14:50 – How early tech limitations shaped Max’s mindset

18:30 – Why many AI tools are still inaccessible

23:10 – The danger of scaling inaccessible AI content

27:40 – Why WCAG compliance is not enough

31:20 – Keyboard-first navigation and real-world usability

36:10 – Minimalist design and why complexity breaks accessibility

41:30 – Accessibility, trust, and customer loyalty

45:20 – The $21 trillion accessibility market opportunity

49:40 – Accessibility as a growth and branding strategy

54:10 – Perseverance vs stubbornness in entrepreneurship

58:30 – Advice for founders facing adversity

01:03:10 – Where to find and connect with Max

01:05:00 – Final thoughts and closing

⸻

🔗 Resources Mentioned

• Max Ivey’s website: theaccessibilityadvantage.com

• Connect with Max on LinkedIn: Maxwell Ivey: https://www.linkedin.com/in/maxwellivey/

• The Accessibility Advantage podcast: https://podcasts.apple.com/us/podcast/the-accessibility-advantage/id1740242884?uo=4

In this episode of The CTO Show with Mehmet, I’m joined by Ahmad Saleem, Founder and CEO of Podyssey.

Ahmad’s journey is anything but linear. From working as a geologist in mining and natural resources to earning a PhD in economics, moving into private equity, and eventually founding an AI startup, his path reflects deep curiosity, resilience, and systems thinking.

We dive into why podcast discovery is fundamentally broken, how AI and natural language processing can unlock the real value hidden inside long-form audio, and what it takes to build and scale a product in an uncertain, fast-moving market.

This conversation blends founder storytelling, product strategy, and honest reflections on failure, team building, and the future of content discovery.

⸻

👤 About the Guest

Ahmad Saleem is the Founder and CEO of Podyssey, an AI-powered search engine designed to help people discover specific insights within podcasts rather than just episodes.

With a background spanning geology, economics, private equity, and natural language processing, Ahmad has been involved in nearly 20 ventures across his career. His work today focuses on applying AI to large-scale content discovery problems, particularly in long-form audio and multilingual environments.

https://www.linkedin.com/in/ahmad-saleem-ansari/

⸻

🧠 Key Takeaways

• Why podcast discovery is harder than ever despite the explosion of content

• How AI and NLP enable searching inside conversations, not just titles

• The difference between finding podcasts and finding relevant moments

• Why categories and genres no longer work for modern podcast discovery

• Lessons learned from nearly 20 ventures and how failure reshapes founders

• How to build lean, distributed teams that move fast without sacrificing clarity

• Where AI agents fit and do not fit in long-form content consumption

⸻

🎯 What You’ll Learn

• How Podyssey is rethinking podcast discovery at a global scale

• Why transcripts alone are not enough to understand context

• How founders should think about feature creep after product-market fit

• What changes when you build AI products in a remote, asynchronous world

• How experience with failure changes decision-making and leadership

⸻

⏱ Episode Highlights & Timestamps

• 00:00 Introduction and Ahmad’s background

• 02:00 From geology and mining to economics and startups

• 05:00 Why podcast discovery is broken

• 09:00 AI, accents, transcription, and context challenges

• 12:00 From episodes to snippets: rethinking podcast consumption

• 15:00 Podyssey’s business model and monetization paths

• 17:00 Avoiding feature overload after product-market fit

• 20:00 Building lean, remote AI teams

• 25:00 AI agents and the future of long-form content

• 27:00 Failure, resilience, and restarting as a founder

• 33:00 The global future of podcasting and multilingual discovery

⸻

🔗 Resources Mentioned

• Podyssey platform: https://www.podyssey.com/