From Finance to Fulfillment: An Entrepreneurial Journey

Matthew Johnson sold his healthcare software company 11 years ago, after leading it through three rounds of fundraising in just three years.

Alongside his twin brother Nathan, he then acquired and transformed TruConnect into a telecom powerhouse. Matthew also co-founded the technology investment bank Drake Star Partners, leveraging his earlier investment banking experience in NYC.

Balancing life between LA and Switzerland, he also leads a nonprofit providing wheelchairs to disabled children. Let’s dive into his unique post-exit lessons on staying motivated, enjoying life, and raising entrepreneurial children.

TIME STAMPS:

00:00:00 - 00:02:34 - Introduction and Career Transition

00:02:34 - 00:03:23 - The First Startup Experience

00:03:23 - 00:06:33 - Building True Connect

00:06:33 - 00:07:50 - Financial Discipline and Management Philosophy

00:07:50 - 00:12:42 - Transitioning from Finance to Entrepreneurship

00:12:42 - 00:15:08 - Balancing Multiple Ventures

00:15:08 - 00:19:05 - Considering Exiting True Connect

00:19:05 - 00:23:28 - Lessons in Hiring and Management

00:23:28 - 00:33:05 - Managing Investments and Personal Fulfilment

00:33:05 - 00:37:21 - Impact of Entrepreneurship on Family and Personal Life

00:37:21 - 00:41:06 - Raising Entrepreneurial Children

00:41:06 - 00:50:02 - Reflecting on Angel Investing

00:50:02 - 00:58:59 - Charity Work and Personal Fulfilment

00:58:59 - 01:08:21 - Life Philosophy and Future Goals