đź‘‹ Hi there, I’m Casey Smith.
I’m a founder, former tech executive, and occasional consigliere to entrepreneurs and SMB owners. My career has been a mix of building, fixing, and scaling—across tech, healthcare, and finance.
Over the last 20+ years, I’ve had the privilege of helping build not one but two companies to over $100 million in ARR. Now, I focus on buying real estate and advising startup founders on how to avoid mistakes I’ve already made.
Prior to becoming an advisor I built the sales, business development, marketing, and customer success teams at IaaS provider, Linode. Over nine years I helped grow ARR from $18 million to over $100 million. Linode was purchased by Akamai Technologies (NASDAQ | AKAM) in March of 2022 for approximately $900 million.
Before that, I was at Kroll where I grew the sales team for the data breach division and oversaw key client relationships including AT&T, Monster WorldWide, U.S. Department of Veterans Affairs, Major League Baseball, Express Scripts, and Google.
Even earlier, I wore the product manager hat at HealthStream (NASDAQ: HSTM), creating SaaS solutions in partnership with Adobe that were adopted by names like The Cleveland Clinic and Hospital Corporation of America (HCA). And yes, back in the ’90s, I bet big on the internet, co-founding two e-commerce startups—TshirtNow and GearPro—one of which taught me the invaluable lesson of humility through bankruptcy. Nothing says “learning curve” like watching your equity evaporate.
I followed my first two startups by co-founding Stairway Media – a creative and media agency focused on understanding what drives human behavior. And since then, I’ve implemented growth strategies for enterprises, valued upward of $1B, across tech, healthcare, and finance.
These days, I focus on buying real estate and coaching founders to grow—both personally and professionally. Along the way, I’ve gained a deep understanding of human behavior, strategic planning, and uncovering growth opportunities where others might not think to look.