Intro:

Dan Hobin’s name is synonymous with entrepreneurship in the state of Oregon. He first gained recognition as the co-founder and CEO of G5, a SaaS company he led to become one of Oregon’s most successful software companies over the last decade. During his tenure, G5 was recognized by Inc. magazine as one of the fastest-growing private U.S. companies and by Deloitte as one of North America’s fastest-growing technology companies. From bootstrapping for five years to securing a minority equity round, later a majority equity round, and ultimately an acquisition by RealPage in 2021, Dan and his team accomplished all of this in Bend, Oregon, before the term “Zoom Town” became popular. At the time of the acquisition, the company had an approximate annual recurring revenue (ARR) of $50 million and over 200 employees.

Dan has always given back to the entrepreneurial community, not only as an angel investor but also by sharing his experiences and helping other entrepreneurs in his community. In 2003, he co-founded the Bend Venture Conference (BVC), which is the largest and longest-standing angel investment conference in Central Oregon and the broader Pacific Northwest. The BVC has helped transform a small timber community into a startup mecca and has rewarded over $14 million in angel/investor financing through its BVC Funds, LLC.

We are excited to have Dan share his story on the Bending Rules podcast, as well as how he’s spending his time these days, which, not surprisingly, includes helping startups scale, among other interests. Enjoy.

4:24 - Intro / Early Ventures

6:18 - Lessons from early failures

9:05 - Importance of capital efficiency

11:53 - The drive to start again, building G5, initial steps

26:56 - Bootstrapping vs overcapitalization

33:02 - Expanding into new verticals, growth pains

44:15 - Lessons when 5 years in, what Dan would have done differently

51:13 - Reflection of leadership

56:50 -- Investing in start-ups: insights and criteria

1:07 -- Building and preserving company culture