Starting Up

A couple tweets from this past weekend hit home with me. The first is a clip from my friend, Tyrone Ross, who succinctly captures the endless decisions and gnawing uncertainty of leading a start-up company.

This thread of 22 tweets from Brian Bourque makes similar points.

Brian’s opening tweet is spot-on: “Startups are HARD. The work has never been done before, so you will constantly feel like you have no idea what you're doing. And you might not. This is uncomfortable, especially if you're a perfectionist.”


I’m not a perfectionist, but I do believe in the pursuit of excellence, so I am uncomfortable. Some days, very uncomfortable. I think we can all go too far with the “no idea what I’m doing” shtick, but undoubtedly the necessary decisions about people, strategy, financing, product, and everything else quickly reveal shortcomings of vision, experience, resources. And that’s just on things I know I don’t know.


The Shaping Wealth team has been working together in earnest for a bit more than half a year now. Most days I have this strange feeling that we’ve accomplished a lot while having accomplished basically nothing. Much is great and much is not.

  • The team is working really well together, yet one of our co-founders resigned.

  • We have a clear vision on our “minimum viable product” (I hate that term), yet I’m not actually sure if it’s a product, let alone viable. Nor is it even minimum: it’s a relatively huge undertaking, for which “thin slicing” doesn’t seem reasonable.

  • The business side (e.g., our capital account, invoicing, operations) seems to be running smoothly, yet the business is so immature that I worry that the feeling of “running smoothly” is providing a false sense of comfort.

  • I’ve put a great deal of thought into the culture I want us to have (and I do think we're moving in the right direction), yet the team has never physically been in the same place, and likely won’t anytime soon.

  • We have seven pilot clients who appear to be pleased with what we are delivering them, yet the “test our ideas with friendly partners” routine sometimes feels scattershot and discombobulated.

  • We seem to have friends and peers who want to invest in Shaping Wealth, yet despite the fact that I own private stakes in speculative startups run by my friends, it feels uncomfortable to sell equity in something, well, speculative.

  • Our corporate vision is audacious: we aim to “transform the human experience of money” and create the opportunity for “funded contentment for everyone.” I love this mission; I feel it in my bones. But some days, I’m like, Really?

I’ve always loved the Robert Frost line that “the best way out is always through.” I can’t control the daily swoons of excitement and fear, but being cognizant of their rhythm at least leaves some space to recall that squaring your shoulders and pushing hard drives you forward, most of the time. That’s where we’re at right now. Onward.

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