From Web Design to Tech Marketing: Michael Cunningham’s Journey episode artwork

EPISODE · Jan 18, 2026 · 46 MIN

From Web Design to Tech Marketing: Michael Cunningham’s Journey

from The Jabari Show · host The Jabari Show

In this episode we talk with Michael Cunningham to talk about his journey from web design into marketing for tech software companies. Michael breaks down what marketing inside tech actually looks like, how demand is created, and why he continues to build websites alongside his marketing career. The conversation explores consistency, content creation, choosing a niche, and overcoming fear when putting work into the world. Michael also shares practical advice for anyone interested in tech marketing, freelancing, or balancing creative work with long-term career growth.Follow Us: Michael:Instagram : https://www.instagram.com/michaelocunningham/The Jabari Show Instagram: https://www.instagram.com/thejabarishowTik Tok: https://www.tiktok.com/@thejabarishow_Jabari M:Instagram: https://www.instagram.com/jabari_matthewTwitter: https://twitter.com/jibrimatthewJabari DInstagram: https://www.instagram.com/jabaridavid/Twitter: https://twitter.com/jabaridavid_Tik Tok: https://www.tiktok.com/@jabaridavid_00:00 – Intro & Catching Up with Michael03:45 – From Web Design to Marketing07:30 – Creating Demand: Getting People to Websites11:45 – Content Creation, Influence & Buying Into Marketing16:30 – Cafés, Co-Working & Why People Like Being Around People22:10 – Accountability, Productivity & Creative Peer Pressure26:00 – How Michael Gets Clients Today31:40 – Working with WordPress & Tech Companies36:50 – Starting a Video Marketing Agency41:30 – Consistency, Showing Up & The Long Game46:20 – Getting Into Tech Marketing: Where to Start52:10 – Personas, Energy & Being Engaging on Camera58:30 – Choosing a Niche as a Content Creator1:04:10 – Ikigai, Passion & Fulfillment1:11:30 – Privilege, Access & Finding Passion Later in Life1:19:00 – Fear, Judgment & Pressing Publish1:26:00 – Final Thoughts & Wrap-Up

In this episode we talk with Michael Cunningham to talk about his journey from web design into marketing for tech software companies. Michael breaks down what marketing inside tech actually looks like, how demand is created, and why he continues to build websites alongside his marketing career. The conversation explores consistency, content creation, choosing a niche, and overcoming fear when putting work into the world. Michael also shares practical advice for anyone interested in tech marketing, freelancing, or balancing creative work with long-term career growth.Follow Us: Michael:Instagram : https://www.instagram.com/michaelocunningham/The Jabari Show Instagram: https://www.instagram.com/thejabarishowTik Tok: https://www.tiktok.com/@thejabarishow_Jabari M:Instagram: https://www.instagram.com/jabari_matthewTwitter: https://twitter.com/jibrimatthewJabari DInstagram: https://www.instagram.com/jabaridavid/Twitter: https://twitter.com/jabaridavid_Tik Tok: https://www.tiktok.com/@jabaridavid_00:00 – Intro & Catching Up with Michael03:45 – From Web Design to Marketing07:30 – Creating Demand: Getting People to Websites11:45 – Content Creation, Influence & Buying Into Marketing16:30 – Cafés, Co-Working & Why People Like Being Around People22:10 – Accountability, Productivity & Creative Peer Pressure26:00 – How Michael Gets Clients Today31:40 – Working with WordPress & Tech Companies36:50 – Starting a Video Marketing Agency41:30 – Consistency, Showing Up & The Long Game46:20 – Getting Into Tech Marketing: Where to Start52:10 – Personas, Energy & Being Engaging on Camera58:30 – Choosing a Niche as a Content Creator1:04:10 – Ikigai, Passion & Fulfillment1:11:30 – Privilege, Access & Finding Passion Later in Life1:19:00 – Fear, Judgment & Pressing Publish1:26:00 – Final Thoughts & Wrap-Up

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From Web Design to Tech Marketing: Michael Cunningham’s Journey

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This episode was published on January 18, 2026.

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In this episode we talk with Michael Cunningham to talk about his journey from web design into marketing for tech software companies. Michael breaks down what marketing inside tech actually looks like, how demand is created, and why he continues to...

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