&gt; Certainly raising $42M and having an over-$100M valuation already put them in the top 1%, right?<p>No, it put them in the top .1%.<p>Easily.<p>But even then, as a founder selling some of your own stock to a VC is not easy.<p>The reasoning behind this is twofold: first the VC wonders if the founder wants to set aside some money for themselves in case things go belly up, in other words, does the founder do this as an insurance premium? (Answer: yes, and why not, why should founders be always stuck with risk). Then the second: ok, so we&#x27;ll make this guy 7 figures rich, what if he doesn&#x27;t show up next Monday or absconds to Tahiti?<p>These and other (minor) fears are reasons why VCs are skeptical about deals where founders cash out (even partially) before they (the VCs) do.<p>Whether that is just or not is up for debate, I think VCs are well within their rights <i>not</i> to do deals, at the same time when you&#x27;ve been in the traces as long as Justin has (I&#x27;ve followed their story right from day 1 because we were in some ways a competitor) a bit of goodwill would be appreciated and I can see a couple of ways in which such a deal could be structured where most of the fears would be laid to rest. Still, it&#x27;s an arrangement between consenting adults and if there is no consent then there is no deal.<p>That&#x27;s tough but that&#x27;s a trap that many founders are caught in, they have the stock but they don&#x27;t have the liquidity and there is no market for their shares where they can get a chunk of cash &#x27;just in case&#x27;. (pun intended).