Welcome to Tweener Madness, the high stakes startup showdown where 8 promising companies go head to head for a $25,000 investment prize from the Triangle Tweener Fund.

Each round, three judges will vote on which startups advance leading up to the finals in early April where one company will take home the top prize from the judges.

Before the competition kicks off, let's meet the people making the tough calls, the judges.

First up, Jan Davis.

Where to Find Jan Davis:

• Linkedin: https://www.linkedin.com/in/janldavis/
• RTP Angel Fund: https://www.rtpangelfund.com/

About Tweener Madness: https://www.tweenermadness.com

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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/

If you ask Alexa who invented Alexa, she'll tell you it was Amazon.com. While that's kinda true, the Alexa foundation was developed by Igor Jablokov and his team at Yap, which was acquired by Amazon in 2011.

Today, we talk to Igor and get the entire story - from a childhood in a Greek cave to pioneering AI advancements that shape the way we interact with technology today. As the founder of Pryon and an early force behind Amazon Alexa, Igor has been at the forefront of AI for over two decades. That's right, two decades in AI.

In this episode, we hear about Igor's journey, the origins and vision for Pryon, the AI revolution, and his predictions for the next wave of technology.

Tune in to hear:

• Igor’s Unique Origins – Growing up in a cave in Greece and how his early encounters with nature shaped his interest in AI and communication.
• The IBM Years – Leading early AI teams at IBM and laying the groundwork for what would become Watson.
• Yap & The Birth of Alexa – How his startup, Yap, was acquired by Amazon and quietly became the foundation for Alexa.
• The Rise of Pryon – Why he started Pryon, what it’s solving, and how it’s different from mainstream AI players.
• The Future of AI – His bold predictions on AI’s role in business, national security, and even understanding dolphins.
• Navigating AI Hype vs. Reality – What’s real, what’s not, and where AI is actually headed.
• Lessons for Founders – Hard-earned wisdom on building a company, securing funding, and surviving the startup rollercoaster.

Where to Find Igor Jablokov:

• Linkedin: https://www.linkedin.com/in/ijablokov/
• Pryon: https://www.pryon.com/

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:

(00:03:00) From a Cave in Greece to AI Pioneer – How Igor’s early years shaped his curiosity about language and intelligence.
(00:10:21) Discovering Computers & Engineering – Learning to code on a Tandy Color Computer and choosing a career in tech.
(00:17:55) IBM & Early AI – Leading IBM’s AI team in the early 2000s and the technology that laid the groundwork for Watson.
(00:27:42) The Yap Story – Founding the first voice-to-text AI startup and working secretly with Apple on Siri.
(00:39:58) Amazon’s Surprise Acquisition – How Yap became the foundation for Alexa and why the deal almost didn’t happen.
(00:50:26) The Dream That Led to Pryon – The moment of inspiration that led Igor to start his next company.
(01:00:01) Raising $100M+ for Pyion – The challenges and wins in building a leading AI company in the Triangle.
(01:14:03) The Future of AI & AGI – Igor’s take on artificial general intelligence, AI risks, and ethical dilemmas.
(01:24:43) Why the Triangle is an AI Hub – The unique advantages of building AI startups in North Carolina.

In the news:

• Amazon Snaps Up Yap And Its Voice-Recognition Technology: https://techcrunch.com/2011/11/09/amazon-snaps-up-yap-and-its-voice-recognition-technology/
• Entrepreneur behind Amazon's Alexa shares why he chose the Southeast to launch his startup: https://www.bizjournals.com/tampabay/news/2024/05/23/ibm-amazon-alexa-igor-jablokov-ai-raleigh-pryon.html
• Raleigh CEO wants to work with every Fortune 500 firm. And he just raised $100 million: https://www.newsobserver.com/news/business/article279533049.html
• The founder who sold the startup that would become Amazon’s Alexa called Big Tech 'apex predators' and says that’s why everyone is scared of AI: https://fortune.com/2023/10/03/amazon-alexa-founder-big-tech-apex-predators-ai-regulation/

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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/

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/