The team behind

Across our educational courses and the token project, one group shares a single mission: making financial freedom simpler, fairer and more accessible. Many have been here since the very beginning — several started as students and grew into roles.

Core team

Dan Hollings

Dan Hollings

Founder of THE PLAN · Protocol Advisor

Dan founded THE PLAN, a record-breaking course launch that reached 20,000+ students across 150+ countries and generated $68 million in retail sales.

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Dan Hollings

Dan holds a degree in classical guitar and taught at the university level before becoming an entrepreneur.

Drew Heriot

Drew Heriot

Co-Founder & Chief Strategy Officer

Since 2021, Drew has developed, refined and taught structured, rules-based approaches to digital asset investing. Working directly with thousands of paying students, he has continually evolved those frameworks through real-world application.

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Drew Heriot

Drew is also an internationally recognised filmmaker and the director of The Secret, one of the most successful feature documentaries ever released.

Ian Jascourt

Ian Jascourt

COO and CFO

Ian brings a computer science background and years of operations leadership to his role as COO and CFO of Bridgegap Marketing, where he builds and scales the systems, teams, and processes behind the company’s growth.

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Ian Jascourt

Ian once appeared in a film with Tom Hanks and he participated in a TV reality show.

Matthew Fisher

Matthew Fisher

Director of Operations

Matt has more than two decades of hands-on experience with launching, running, and growing enterprise-grade software ventures, including companies that were subsequently acquired for >$50M USD.

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Matthew Fisher

Matt has lived in a handful of countries including Jamaica, Canada, the US, Australia, and now New Zealand.

Alice Shikova

Alice Shikova

CMO / AI Growth Strategist

Alice is a Web3 fintech marketing leader, specializing in go-to-market, adoption, and AI-native growth. She’s an expert in the AgentFi sector and a co-founder of a Web3 marketing community in Lisbon.

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Alice Shikova

Alice has spoken at a United Nations blockchain academy program and 30+ blockchain conferences worldwide. She has participated as a keynote speaker, judge, and mentor.

Ashley Armstrong

Ashley Armstrong

Chief Education Officer

Since co-founding THE PLAN in 2021, Ashley has shaped THE PLAN’s educational experience for members in more than 150 countries. Her focus is making complex investing concepts simple, practical, and easy to apply.

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Ashley Armstrong

Ashley is a TEDx speaker, former professional athlete, bestselling author, and contributing writer for Entrepreneur.com whose work explores the intersection of psychology, neuroscience, and human achievement. She has also been featured on NBC, CBS, ABC, and FOX.

Daniel Hall

Daniel Hall

Director of Business Relations

Daniel is a USA Today and Wall Street Journal bestselling author — and also an attorney and a registered nurse.

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Daniel Hall

Daniel’s academic research appeared in the Vanderbilt Journal of Transnational Law and received substantial engagement from a Nobel laureate in Economics.

Anthony Hall

Anthony Hall

Crypto Market Quant Researcher

Anthony brings more than 15 years in publishing and financial communications, turning complex ideas into clear, compelling narratives.

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Anthony Hall

Anthony is an avid rock climber and has done it on 3 different continents so far.

Sarah Sternberg

Sarah Sternberg

Director of AI Systems

One of Dan’s original ten mentees, Sarah joined THE PLAN early and now mentors students herself. She previously built a new accounting method for $18.8 billion in commercial real estate assets and a returns model behind more than $1 billion raised.

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Sarah Sternberg

Sarah first landed in Rwanda without knowing a single person. Fifteen years later, Rwanda is still one of the places she calls home.

Roxy Stephenson

Roxy Stephenson

Director of Customer Experience

Roxy brings more than 15 years of experience working with business leaders and executives, including six years at Microsoft managing a portfolio of business client accounts and working with CIOs and leaders to anticipate needs and navigate major technology initiatives.

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Roxy Stephenson

Roxy was a Tony Robbins Platinum Partner, an experience that took her around the world—including to India, where she became a Blessing Giver via Oneness University.

The mentors guiding members

Cody Punt

Cody Punt

Student Mentor

Guiding members at every experience level to personalize and scale an approach that fits their unique goals and budget — after two years road-tripping the US with his wife and dog before becoming a dad.

Kathleen E. Sinclair

Kathleen E. Sinclair

Student Mentor

Helping members over 60 build confidence, master the strategies, and see AI not as a replacement but as a way to make the most of everything they've already learned.

Want to talk to the team?

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