Episode 3: Permission to Act with Rob Walling

October 13, 2026 • 00:39:25
Episode 3: Permission to Act with Rob Walling
Permission with Dr. Sherry Walling
Episode 3: Permission to Act with Rob Walling

Oct 13 2026 | 00:39:25

/

Show Notes

I've been married to Rob Walling for almost 24 years, so I went into this one already knowing the plot. Rob was raised to follow the rules, with a whole career mapped out as an executive at his family's electrical construction company. Then he got into the management training program, realized he was miserable, and walked away with no connections and no plan except that he liked writing code.

Rob is the founder of Drip, co-founder of TinySeed, and the host of Startups for the Rest of Us. We get into the years he built on nights and weekends before he'd let himself quit the day job, the tattoo he got of a hand drawing a map, and the arrival fallacy that left him restless three months after getting everything he'd worked for. He makes the case that the buck stops with the founder, which means you're allowed to do far more than you think.

Mostly, it's an episode about giving yourself permission to make bold, imperfect decisions and act before you feel ready.

Rob writes at robwalling.com and hosts Startups for the Rest of Us.

Other Episodes

Episode

January 25, 2019 •
Episode Cover

Episode 202: Success, Therapy, and MDMA with Tucker Max (Part 2)

In part 2 of Sherry’s interview with Tucker Max, they talk about his career changes and the pursuit of finding the right kind of...

Listen

Episode 380

January 26, 2024 • 00:20:58
Episode Cover

Episode 380: Is Resentment Holding You Back?

In this insightful episode, Dr. Sherry Walling dives into a vital yet often overlooked aspect of leadership: the power of forgiveness. This discussion challenges...

Listen

Episode

March 04, 2015 •
Episode Cover

Episode 7: Becoming a Stress Ninja

Rob and Sherry talk about their favorite tactics for mastering stress. Resources for this episode: Why Zebras Don’t Get Ulcers

Listen