Oct 13, 2026 · 40 min · 13 segments
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…
Sherry WallingHost
I think one of the vulnerabilities that many entrepreneurs have is hiding in what they're good at, right? Whether you've come up as a coder, you stick with that as long as you possibly can because you're good at it, you're comfortable at it.


But where is comfortable for you and where is the pull to hide in that or cling to that? And what's your relationship with that now?
This is a really good question because I talk a lot about this on my podcast and I talk about this certainty versus uncertainty framework of, I get the question, what should I, I don't know what to work on next for a new founder or an old founder, frankly, an experienced founder.
You know, there's certain things that are just certain in a business at any age.
And then there are things that are uncertain, like can we market this? Can we sell it? What should we price it at? Blah, blah, blah.
So I like that I get to preach that to everyone and Now you're asking me today, what is my comfort zone? I will admit, I have a luxury today of having between the two companies that I run, MicroConf, TinySeed, there's 10 of us.
And I think there can be a bit of an adrenaline junkiness in being an entrepreneur.
imagine either you or I or any great entrepreneur we know going and working like a middle manager job at Target or Best Buy, corporate? Cannot.

I think one of the vulnerabilities that many entrepreneurs have is hiding in what they're good at, right? Whether you've come up as a coder, you stick with that as long as you possibly can because you're good at it, you're comfortable at it.


But where is comfortable for you and where is the pull to hide in that or cling to that? And what's your relationship with that now?
This is a really good question because I talk a lot about this on my podcast and I talk about this certainty versus uncertainty framework of, I get the question, what should I, I don't know what to work on next for a new founder or an old founder, frankly, an experienced founder.
You know, there's certain things that are just certain in a business at any age.
And then there are things that are uncertain, like can we market this? Can we sell it? What should we price it at? Blah, blah, blah.
So I like that I get to preach that to everyone and Now you're asking me today, what is my comfort zone? I will admit, I have a luxury today of having between the two companies that I run, MicroConf, TinySeed, there's 10 of us.
And I think there can be a bit of an adrenaline junkiness in being an entrepreneur.
imagine either you or I or any great entrepreneur we know going and working like a middle manager job at Target or Best Buy, corporate? Cannot.
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