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in 30 or 40 million dollars, where, honestly, the kinds of things that I can do
and the value I bring is much less than it was earlier in a company's life. At
these companies, we have brought on new board members—both indepen-
dents with tremendous amounts of domain experience and later-stage growth
investors that understand how to help companies go from 20 million to 200
million to 2 billion in revenue. I've never done that, so it's great for me to have
a seat at the table and soak up the learning. While I still help with recruiting
and financing strategy, the more detailed discussions around business model
and achieving product/market fit fall away when the emphasis shifts from
“figuring it out” to rapid scaling.
Gutierrez: How do you stay so grounded?
Ehrenberg: This is easily the most humbling business I've ever been a part of.
There's not a day that goes by that I don't feel stupid at one time or another.
This business is so difficult.
Though Fred Wilson is obviously one of the most successful venture investors—
certainly of this era, if not of all time—he is also unbelievably humble. Fred
continues to be one of my principal mentors and was one of my early supporters.
He said to me very early on that he always feels like he's learning and regularly
feels like he's making mistakes. That really stayed with me. I also think that as
I've gotten older and I've had successes and failures that I have much greater
empathy now than I did when I was young, cocky, and “taking on the world.”
At this point, I feel very much in my zone and it's not about proving anything
to anybody but myself and trying to help however I can, so I think that helps
keep me grounded.
Gutierrez: How do you evaluate new opportunities when facing this level of
business difficulty?
Ehrenberg: Generally, when opportunities come in, there's going to be three
different types of deals. A cold deal comes in with no introduction from a
trusted source. Then there are more warm introductions from other investors.
Finally, there are warm introductions from entrepreneurs in our ecosystem.
Every piece of inbound is implicitly weighted by virtue of its provenance.
Things that are from trusted and respected sources will be prioritized. We
have a pretty clear philosophy, as well as a very defined approach at which
point we are interested in investing. We are early-stage investors. So it's got
to be somewhere between incubation and pre-Series A. The area between
Seed and “Seed prime” [or seed extension], is probably the fat part of the
distribution of when we initiate an investment. So there's a lot of stuff that has
to line up for us to even want to look at a company in depth.
Let's say there's a company at the right stage in an area we're passionate
about with a founding team that in first interactions seems compelling. One
of us is the deal lead and generally first meets with the founding team. If
there's continued interest at that point, then we'll really start to figure out the
 
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