Episode 709 | The 7 Greatest Investments of My Life

In episode 709, join Rob Walling for a solo adventure as he shares his story of growing his personal wealth over the past few decades. Selling companies was the major driver of wealth, but he also explores the role of cryptocurrency, running profitable companies, and angel investing. Rob emphasizes the power of entrepreneurship in achieving financial freedom, while acknowledging there are ways to do so while keeping risk relatively low.

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Topics we cover: 

2:50 – A lesson on how to build wealth

4:31 – Entrepreneurship was our biggest tool

6:37 – Building, acquiring, then selling companies

10:45 – Building slowly while staying risk-averse

13:27 – Investing in riskier assets like cryptocurrency

19:39 – Running profitable companies

20:56 – Angel investing, and WP Engine

23:44 – Traditional, salaried employment

24:53 – Typical investments: stocks, bonds, REITs

27:36 – Real estate investing

Links from the Show: 

MicroConf Connect

Christopher Gimmer (@cgimmer) | X

Christopher’s tweet

Sherry Walling (@sherrywalling) | X

The Stair Step Method of Bootstrapping

Start Small Stay Small by Rob Walling

This Took 11 Years to Be An "Overnight Success" - SaaS Exit Strategy

Zen Founder

The SaaS Playbook by Rob Walling

WP Engine

TinySeed

Barbell Strategy Explained for Stock and Bond Investors

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode.