From Dyslexia to CEO: AI, Entrepreneurship & Fundraising Strategies w/ Rob Matzkin

Discover how AI, entrepreneurship, and smart fundraising strategies turned dyslexia into a superpower for CEO Rob Matzkin. In this Business 101 Podcast episode, Rob shares how he built Booze Carriage—the first alcohol delivery service in the US—raised capital for MyQuest in edtech, and now leads a $50M deep tech fund at Singularity Ventures.What you’ll learn:• How dyslexia shaped Rob’s mindset and entrepreneurial advantage• Building Booze Carriage and navigating alcohol delivery compliance• Lessons from MyQuest: why B2B edtech wins over B2C• Practical ways AI gives operators a competitive edge• Fundraising frameworks: pre-seed vs seed vs Series A vs family rounds• Coaching founders from first $20K MRR to $1M raised• Building culture that rewards outcomes, not hours• Why your network defines your net worthRob delivers a no-nonsense playbook for founders, investors, and innovators—combining AI, business strategy, and fundraising mastery to disrupt industries and scale ideas into companies.Chapters:00:00 – From dyslexia to entrepreneurship; college hacks that worked14:32 – Booze Carriage; innovating alcohol delivery and staying legal21:12 – Building MyQuest; B2B edtech over B2C28:48 – AI in business; real workflows and vibe coding33:46 – Fundraising today; friends and family vs pre seed vs seed vs series A45:24 – Coaching founders; first 20k MRR to first $1M raised46:48 – Corporate culture; measure results not hours57:39 – Final advice; be authentic; be vulnerable; take risks58:01 – Wrap and takeaways✅ Subscribe for weekly C-suite playbooks✅ Comment your biggest takeaway✅ Share with a founder who needs this✅ Like if you want more no-fluff business lessons✅ Join the Business 101 community