Presenting: Founder’s story: The Hard Lessons Behind Long-Term Success
Every entrepreneur eventually faces moments that force hard decisions about value, direction, and resilience. In this session, Steve shares three defining stories from his life and career that shaped how he thinks about business, leverage, and what truly matters. His stories reveal lessons that still apply to sellers today.
You’ll hear how understanding your value and being willing to walk away can change power dynamics, why many businesses become “coal mines” that drain energy instead of creating leverage, and how identifying the right pivot can unlock entirely new opportunities. Steve will also share how technology became a turning point in his career leading to a scalable, global growth.
This talk offers perspective, clarity, and reminders that long-term success is built by choosing the right battles, protecting your dignity, and making decisions your future self won’t regret.
About Steve:
Steve Simonson is a lifetime entrepreneur having founded, purchased, built, and sold numerous companies over the past 3 decades. Along the way Steve’s companies have been publicly recognized with three consecutive years on the Inc. 500 list, multiple listings on the Internet Retailer Top 500, Washington State Fastest Growing Business as well as a multitude of other company accolades. Steve was also a finalist in the Ernst and Young Entrepreneur of the Year Award. Retirement 2.0 is all about Steve focusing on the things he loves and cutting down work to only 40-50 hours a week. Although Retirement 2.0 is anything but traditional it is a mindset that reminds Steve to focus only on bringing value and not doing things for the sake of getting things done. Creating lasting value means more.
Some interesting facts about Steve and his entrepreneurial journey:
- First million dollar year in 1994. (Retail)
- First million dollar month in 2004. (All e-commerce)
- First million dollar day in 2006. (All e-commerce)
- Cumulative sales in the last 20 years over 2 Billion in our own cash registers (not 3rd parties). (Retail, eCommerce, Wholesale)
- Over time we’ve shipped enough containers to go up and down mount Everest close to 40 times.
- At times certain business units would have 500+ employees.
