Jason Eckenroth

Founder/exCEO, ShipCompliant

Jason bootstrapped his first company, www.ShipCompliant.com to help wineries simplify compliance and lower the barriers of entry for direct sales.

Over a 16yr time frame the business grew to a $12M ARR. He believes customers chose ShipCompliant, not for the features, functionality or price, but ultimately because they liked how the company did business. It’s the greatest competitive differentiation.

Bootstrapped to Acquired: A Raw Share of the Ecstasy and Agony of a Successful Exit

Jason started ShipCompliant in 2000 as a consultancy, making the switch to a SaaS business in 2005. He bootstrapped the business to $8.5M ARR, $3M distributable profits, owning 80% of the addressable market in the industry at the time of sale to a private equity house. Jason stayed with the business and continued to grow ShipCompliant post acquisition until he left last year. A year after the acquisition, the parent company was acquired itself and Jason ‘moved on’. So far, a pretty ‘normal’ story of ‘successful’ entrepreneurship.

So, what’s different? The headlines don’t tell the full story. Jason moved to Barcelona last year to get distance and catch up on life with his family. He felt he needed a clean break and time to think about why a ‘successful exit’ felt so wrong. Only after he sold could he see in black and white the effect it had on himself and those around him – and the events leading to the decision. Jason will share some of the things he did to make ShipCompliant the successful business that it is. More importantly, he’ll talk about the mistakes he made in selling and what he wished he had realised before he did. He believes ‘Exit by acquisition’ should not be the only manifestation of success for bootstrappers.