This week I got the rare opportunity to have a low key dinner with the founders working at the NewME Accelerator in San Francisco. It was a great visit—the energy and sophistication of the teams there was really strong, and I enjoyed the time.
This talk was strictly Q&A—just me sitting with a group of around 15 founders, fielding questions one after another. I love this format. But if you’ve spent time with me, you’ll know once I get started I don’t really stop talking, so this may not be all that unique.
The founders’ questions were many. Some were specific and use case oriented, such as, “Our team has built a product, we’re getting traction, and we think we need to raise a small seed round. Some are suggesting we raise more, what do you think?” In your case, given the instincts that’ve gotten you this far, I reco following them going forward. If you have an offer to raise more, then think about that then.
Or, “I’m a founder with unique and differentiated real world experience in a specific market, and I want to hire a tech team to build a product this industry needs. How do I raise money to hire them or how to do I hire them before I have money?” Catch 22 — not sure what to say, just have to figure out a solution.
Others were pretty hypothetical, “If you had one company with 2 million users and no revenue, and another company with a small number of users and $50,000 in revenue, which would you be more likely to invest in?” Hm. Totally depends on trajectory and relative opportunities of the two.
In answering the questions, I often had to reiterate a caveat I find myself making a lot these days. Namely, when I’m answering a question on a business I know only lightly, as in when I show up at a Q&A with founders, my answers are going to be broad brushstroke generalizations. These generalizations may not work for you in your particular situation. Mileage can vary, a lot. The core truth is that your on the ground reality may be the sort of thing where my advice, or the advice of other outside perspectives, is pretty useless or even harmful.
In my own experience, in building startups the core on the ground reality is pretty muddy and opaque. This is a constant reality—startups are inherently dealing in uncertainties, and uncertainty creates ambiguity. Uncertainty and ambiguity is more the norm than the exception.
At the same time, many in our community, investor types like me and other outsiders, present a worldview that is much more certain. Company 1 is screwed, Company 2 is can’t miss. Do A, do not do B. The world is black; not white. Approach y worked for company x, so you should think about doing y too. In an uncertain world, the narrative of certainty is valued.
I disagree with this thinking. Far more is unknown than known, especially by those of us far removed from the front lines of our business. I encourage founders to hear out different opinions, but retain your own perspective, informed by the reality of your situation.
In most cases, the situations we’re dealing with aren’t black and white. They’re gray. Beware of people who make you think the answers are simple and that generalities work.
If the answers were simple, anyone could do this stuff.