Jordan DiPietro is a founder coach, executive advisor, and two-time CEO who helps first-time founders, solopreneurs, and recently hired CEOs in the $2 to $20 million revenue range grow without burning out. After spending 20-plus years in the C-suite at companies including The Motley Fool, HubSpot, and Hampton, Jordan now runs an intentionally small advisory practice and writes the weekly newsletter Signal//Noise.
Jordan DiPietro has been a guest in The Business Owner's Journey podcast:
Jordan works one-on-one with founders and CEOs, capping his client roster at seven to keep the work high-touch. His coaching draws on a career's worth of pattern recognition in business, diagnosing the recurring problems founders face across three categories he calls the three signals: self, team, and model.
He developed the 3H leadership framework, which stands for high expectations, high support, and high transparency. It reflects his core belief that high performance culture and treating people well are not mutually exclusive.
Jordan also recently partnered with executive recruiter Ty Burke to launch the Founder Handoff, a service that combines founder coaching with CEO search to help founder-led companies navigate the CEO transition successfully.
Jordan DiPietro joined The Motley Fool around 2009 and spent over a decade there, rising from Managing Editor to VP of Product to Chief Growth Officer. During his tenure, he helped scale subscription revenue past $300 million and founded The Blueprint, a SaaS review site launched as a new business line under The Motley Fool brand in 2019.
In 2021, Jordan became CEO of The Hustle after HubSpot acquired the business newsletter. He oversaw its growth to over 2 million daily subscribers while serving as VP of HubSpot Media, managing content, creator, and podcast strategies for the platform.
Jordan DiPietro then became CEO of Hampton, the private founder community co-founded by Sam Parr and Joe Speiser. He scaled Hampton to over $10 million in annual recurring revenue and more than 1,000 members in roughly two years before stepping down in early 2025.
Jordan launched the Signal//Noise newsletter, where he shares reflections on leadership, founder decision-making, and the operational realities behind growing companies. Signal//Noise publishes weekly essays and tactical advice that have been referenced by startup operators and CEO peer groups.
His thought leadership centers on demystifying the gritty, real-world challenges faced by founder-led companies. His recent writing and frameworks address:
Jordan also shares insights via LinkedIn, including detailed breakdowns on managing growth and leadership handovers. He has appeared as a guest on multiple podcasts, including The Rebooting Show with Brian Morrissey, The HeyCreator Show, and the Newsletter Operator podcast, where he discussed community business models and scaling paid memberships. He also appeared on The Business Owner's Journey podcast with Nick Berry.
Jordan is based in the United States and comes from a background in fast-paced online media and startup communities.
He spent over a decade at The Motley Fool in various leadership roles before making his mark with Hampton. Jordan’s network includes co-founders, high-growth CEOs, and serial entrepreneurs, connecting him with the world of founder-led scaling.
His path into the startup world was not entirely conventional. Before all of that, he worked as a butcher -an experience he sometimes references when talking about craft, discipline, and learning by doing.
He is a father of two children, a lifelong cook and proud Philadelphian. He often writes about leadership, startups, money, and life, usually drawing on lessons from both business and family life.
Nick Berry is an American entrepreneur and business advisor, whose track record includes founding, leading, and advising award winning small businesses since 2002. He has built companies in multiple industries, hosts The Business Owner’s Journey podcast, and created the Business Alignment System™ framework that helps owner-operators scale without burning out.
After his most recent exit he founded Redesigned.Business to advise and coach to other entrepreneurs and business owners who are looking for a trusted (and proven) advisor.
Among peers, colleagues and clients, Nick has been referred to as 'The Anti-Guru', due to his pragmatic approach and principled leadership. He shares his thoughts, experience, and lessons learned each week in The Golden Thread newsletter.
