Dave KashenStartup CEO Coach / 2x founder

The Power of Listening to Your Wants as a Founder

18 Oct 2026 · 1 min

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1:00

In this reflective segment, the founder recounts how he conceived an Austin Founders Retreat centered on wakesurfing as a warm‑weather alternative to ski‑focused events. After announcing the retreat for September, he faced a stark lack of sign‑ups. While his entrepreneurial instinct urged him to intensify outreach—contacting a friend named Jesse, tapping VC networks, and hustling to boost attendance—he consciously chose to listen to his own desire not to push the event forward. He set a personal rule: proceed only if enough people signed up, otherwise cancel. Ultimately, the retreat was cancelled, illustrating his decision to prioritize personal authenticity over forced hustle.

Chapters

I said, oh, it would be fun to do like a warm weather equivalent, you know, with like wakesurfing instead of skiing and, you know, mixing in this. And so I announced this like Austin Founders Retreat in, I think it was September. And very basically nobody signed up is the short version. And like the entrepreneur in me, the intellect was like, well, get, get your ass in gear, right? Like, Reach out to Jesse, ask him to ping his people, reach out to all your VC contacts. I had all this, you're about to fail, you gotta do a bunch of, you go hustle. And I just really, I attuned and I was like, I don't want to. I noticed I just don't want to. And I allowed myself to just follow my wants and I didn't do it. And I basically said, if somehow people sign up, I'll do the event. And if not enough do, I will cancel it. And I ended up canceling it.