Series A(ggregate)

We spend a lot of time around here covering the latest startup fundraises, and for good reason. While capital is certainly an input and not an output, there is nothing quite like the closing of a round of several million in venture capital to prove that yes, the startup I'm working on is at least interesting to someone other than me. External validation shouldn't be your motivating principle, but it is motivating. Plus, it's a great milestone to reach out to the press and start talking up the story.

And so week after week, we cover the latest rounds. This company raised $4.5 million in a seed round, and this company raised $16 million in a series A. These stories - and the narratives behind them - are crisp, clean, and precise. A proverbial founder walked up and down South Park in SoMa, explained their story, collected a couple of term sheets, picked one, locked in the due diligence, and is now announcing their round. The VCs are excited, the founder(s) are excited, the employees are excited (and sometimes even the customers are excited!)

The reality for founders though is far more messy and gritty than those headlines would indicate. When I get founders off the record and out for drinks, the true story starts to emerge. That $4.5 million seed fundraise took eight months of maniacal scheduling with two hundred investors just to find a lead. And that lead didn't lead lead, but took only 20% of the round. In the meantime, they raised twelve times across convertible notes and SAFEs, each one giving the company just a bit more gas in the tank to continue.

When I wrote that a startup raised $4.5 million in one slam dunk, what I really should have written was that they raised $150k, $300k, a few more $50k investments from randos, a couple of thousand from that startup competition, wow $500k from that amazing angel, a $750k SBIR grant from the government that took nine months too long to process, some credits from Brex, and finally at some point that lead investor showed up who gets $3-3.5 million in news value credit on their wimpy $900k check.

As an editor and a writer who covers these aggregate rounds, I struggle with how to approach them. Founders regularly tell me that they would love more transparency and less bravado around fundraises. They want to read how other founders handle the messy complexity of their fundraises, if only because they can compare their own hellish experiences with those of others.

More fundamentally, our readers deserve to read the truth. A $4.5 million round led by a single venture firm writing a $3.5 million check is a very different construct than a bricolage of a random assortment of angel investors. That difference in investor and round quality does indicate something about the startup under examination, and so offering more of those details would better inform our readers as well.

All that is well and good, but no one really wants to hear about these difficulties. Certainly users and customers don't want to hear about how the software they use or purchased is run by a company that is constantly days away from death. Some early-stage employees probably have the focus to ignore such morbid considerations while carrying out their functions, but many need their paychecks to come from a black box. Somehow, the checks always arrive, and that lowers the stress for everyone.

And even just in terms of the craft of writing, do we really want to exchange the standard funding sentence ("blah blah blah raised blah from blah with participation from blah blah blah") with a multi-paragraph exegesis of a fundraise?

Writing is about choosing which details are salient and which to pass over. It would be exhausting every morning to read tomes of fundraise detail. Yet, our consistency in depicting fundraises as efficient and precise can create an atmosphere where if you didn't find a lead in a few weeks and lock down the whole round, you are a failure.

That's not really a depiction I want to support.

And so, take this as someone who talks to dozens of founders a year off the record about their fundraises, and also sat on the other side of the table as a VC for years. Fundraises are almost always really, really, tough. Very few people get commits in the first meeting, or even in the subsequent meetings. Half the investor introductions during a fundraise are often a complete waste of time if not outright damaging, psychologically or materially. There are a lot of sharks out there. It is much more common today to aggregate a bunch of mini-rounds than it was a couple of years ago.

This is not failure, but just the path of the entrepreneur today in 2019. And at the end of that whole long and windy road, after all of those hundreds of hours of coffee meetings and PowerPoint strategy sessions and skeptical investor convos, all of that work will boil down to twenty words about how the fundraise closed, X dollars were raised, and money was seemingly wired magically to your bank account.

You, me, and really everyone can and should know the truth. But perhaps just rejoice in that headline, and get back to the next slog.