The Founder Multiverse: 60 VC Rejections, An Adobe Exit, and the Appetite to Dominate | Alex Packham

In this episode of Scaling Stateside, David Rose and Matt Oxley sit down with Alex Packham, the mastermind behind ContentCal (acquired by Adobe) and the current CEO of JAAQ (Just Ask A Question).

Alex breaks down the raw reality of the "Agency-to-SaaS" pivot, the grueling "David vs. Goliath" battle of selling to a Silicon Valley giant during a global lockdown, and why he believes the US market possesses an "appetite to dominate" that every European founder needs to experience.

If you’ve ever felt like you’re living in a "multiverse", balancing the public face of growth with the private stress of cash flow, this conversation is for you.

📍 KEY TOPICS & TIMESTAMPS

02:58 Early Entrepreneurial Experiences

06:02 The Mindset of an Entrepreneur

08:47 Career Path and Agency Experience

12:09 Transitioning to ContentCal

14:47 Fundraising and Venture Capital Journey

17:59 Product-Led Growth and Market Expansion

29:59 Identifying the Ideal Customer Profile (ICP)

33:06 Navigating the U.S. Market During COVID-19

35:55 The Journey to Series A Funding

39:58 The Acquisition Process with Adobe

45:54 The Human Side of Entrepreneurship

50:51 Transitioning to Jack: A New Venture

57:44 Advice for Aspiring Entrepreneurs

ABOUT ALEX PACKHAM

Alex Packham is a serial entrepreneur, angel investor, and the former Founder & CEO of ContentCal, a social media planning tool he scaled to thousands of global customers before its high-profile acquisition by Adobe in 2021.

Known for his "wise beyond his years" strategic thinking, Alex successfully navigated the complex transition from a profitable digital agency to a venture-backed SaaS powerhouse. Following his tenure as a Product Director at Adobe, he took the helm as CEO of JAAQ (Just Ask A Question), a mental health tech platform featuring world-leading doctors and celebrities. Alex is a frequent investor in early-stage startups and is passionate about helping founders navigate the mental and operational "multiverse" of scaling a business.

🔗 CONNECT WITH Alex Packham 

LinkedIn ⮕ https://www.linkedin.com/in/alexpackham/

JAAQ ⮕ https://jaaq.app/home

🔗 CONNECT WITH David Rose

LinkedIn ⮕ https://www.linkedin.com/in/davidbrose/

🔗 CONNECT WITH Matt Oxley 

LinkedIn ⮕ https://www.linkedin.com/in/mdoxley/

🏢 POWERED BY WILSON SONSINI 

This episode is powered by Wilson Sonsini, the leading law firm for technology and growth companies. Wilson Sonsini helps European founders navigate US expansion — from entity formation and regulatory compliance to VC fundraising and M&A. Their deep cross-border expertise ensures you structure it right from day one.

US Expansion Partners ⮕ https://www.usxp.co/

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