👋 Hi there, I’m Casey Smith.

I’m a founder, advisor, and former tech executive.

Over the last two decades, I’ve helped build two $100MM+ ARR companies.

Now I buy small businesses and real estate and fix them up. I also provide executive coaching and advisory services for early-stage SaaS entrepreneurs and SMB operators.

Prior to becoming a coach I built the sales, business development, marketing, and customer success teams at IaaS provider, Linode. Over 9 years I helped grow revenue from $18 million to $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.

During my time at SmithReed, I helped develop growth strategies for family-owned SMBs.

At SaaS and e-learning provider HealthStream (NASDAQ | HSTM), I was a product manager. I helped develop learning and competency software in partnership with Hospital Corporation of America (HCA) and Adobe that was adopted by Sutter Health, Tenet Healthcare, The Cleveland Clinic, and Christus Health among others.

And WAY back, in 1995, after identifying “the internet” as the next growth platform for business, I founded two of the first e-commerce companies on the Web – TshirtNow and GearPro. We bootstrapped TshirtNow and raised capital for GearPro.

Then GearPro went through something American and efficient — bankruptcy. The equity holders, including yours truly, were wiped out.

In the fall of 2000, I found myself a newlywed, deeply in debt, with no job. I learned, started again, and grew.

I followed my first two startups by co-founding Stairway Media – a creative and media agency focused on understanding what drives human behavior.

Since then, I’ve implemented growth strategies for enterprises, valued between $1MM and $1B, in cloud computing, risk management, e-learning, healthcare, and financial services.