Few Triangle founders have experienced as many highs and lows as Jud Bowman.

From launching his first startup as a high school student to navigating the dot-com bust, leading Motricity through a billion-dollar market cap, and pivoting multiple times to stay ahead of industry shifts, Jud's entrepreneurial journey is nothing short of legendary.

In this episode, Jud discusses the evolution of his companies—Pinpoint, Motricity, Appia, and now Sift Media. Everything from cold-emailing VCs in the '90s to the rise and fall of ringtones, the power of persistence, and what’s next in the world of mobile advertising.

Tune in to hear:

• Tales of a High School Startup. How a high school dorm project turned into a funded startup.
• Surviving the Dot-Com Bust. Fraudulent CEOs, running out of cash, and hard pivots.
• The Ringtone Gold Rush. The unexpected billion-dollar market that changed mobile forever.
• Being Bought vs. Going Public. From 58 investor rejections to raising $14M and IPO plans.
• The iPhone Effect. How Apple’s closed ecosystem forced a total business reset.
• The Fall & Rise of Sift Media. Building and rebuilding in a privacy-first advertising world.

Where to Jud Bowman:

• Linkedin: https://www.linkedin.com/in/judbowman/
• Sift Media: https://www.sift.co/

Where to Find Scot Wingo:

• Linkedin: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:

(00:00:03) The Internet Bubble Wake-Up Call – Jud’s first taste of dot-com economics with a $500K “opportunity” from NBC.
(00:05:00) From Dorm Room to First Funding – How two high schoolers convinced investors to back their startup.
(00:14:00) Surviving the Dot-Com Bust – The hard lessons of a fraudulent CEO and a failing business model.
(00:26:00) Pivoting to Mobile – How a chance discovery of early mobile search led to a billion-dollar business.
(00:42:00) The Ringtone Gold Rush – Why ringtones were the first billion-dollar mobile market.
(00:53:00) Raising Big Money & Going Public – From pitching VCs to working with Carl Icahn.
(01:02:00) The iPhone Effect – How Apple’s closed ecosystem changed everything.
(01:10:00) The Fall & Rise of Sift Media – Pivoting again in a world of privacy-first advertising.

In the news:

• Jud Bowman’s startup Sift Media is raising more debt: https://wraltechwire.com/2023/06/30/jud-bowmans-startup-sift-media-is-raising-more-debt/
• First in Future: Entrepreneur, Sift Founder and CEO Jud Bowman: https://iei.ncsu.edu/2017/09/26/firstinfuture-ep34/
• The Midas touch: Jud Bowman talks new $1.5M raise, meteoric rise of startup No. 3: https://wraltechwire.com/2020/02/27/the-midas-touch-jud-bowman-talks-new-1-5m-raise-meteoric-rise-of-startup-no-3/
• Triangle entrepreneur Jud Bowman launches third startup: https://www.newsobserver.com/news/business/article52917725.html

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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Earfluence.

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/