10: Behind the Exit: Lessons from Ross Shanken’s Nine-Figure Journey with Jornaya
Ross Shanken, Founder, Advisor, Investor and Entrepreneur
In this episode, host Bruce Eckfeldt sits down with Ross Shanken, founder and former CEO of Jornaya (originally LeadID), to explore the full arc of his entrepreneurial journey—from startup spark to strategic acquisition. Ross shares how his early fascination with technology and entrepreneurship led him from Wall Street by Fax to founding Jornaya, a company that brought transparency and compliance to the online lead generation space.
Ross discusses the core problem he identified in the market: lack of accountability and verification in B2C lead transactions. His solution—a universal LeadID tied to each consumer lead—enabled better compliance and higher quality assurance for buyers and sellers alike. Building this double-sided marketplace required significant persuasion and patience, particularly in convincing both lead sellers and buyers to adopt a new standard.
Financing the company initially from personal savings, Ross brought in outside capital only when it aligned with strategic growth. He shares lessons learned from his first, unsuccessful exit attempt in 2019, including the critical importance of running your own process and not being pressured by external investor timelines. After regrouping, his team realigned using strategic planning tools like vision alignment, headline exercises, and operational backcasting—eventually leading to a successful nine-figure exit in 2021.
Ross reflects on the personal and professional discipline required to scale and exit, including the importance of hiring ahead of the curve (e.g., bringing in a CFO early) and creating honest, kind, and direct communication within the team. He also touches on his post-exit evolution, which led to the launch of his new venture, Vojomo, focused on strategic growth planning for other founders.
Key Takeaways
Establish your financial model early and revisit it often to inform strategic decisions.
Align your leadership team using shared vision exercises like “headline planning.”
Avoid exiting on investor-driven timelines—run your own deal process.
Bring on key roles (like CFO) earlier than you think you need them.
Use backcasting: start from your ideal exit and work backwards operationally.
Honest internal dialogue creates stronger strategic alignment and execution.
Validate your market thesis with early feedback loops from prospective acquirers.
Sitting in discomfort post-exit can be a powerful period of personal growth.
Contact Information:
ross@vojomo.com
