In January, I wrote The Hardest Round to Raise which argued Series B rounds would be the most challenging early stage round in 2017. Irrespective of the annual vicissitudes of the fundraising market, Series Bs are always the most challenging rounds to raise because they are in-between rounds. The Series B is the pimpled and gangly adolescent phase of startup evolution.
If the aim of every round of venture funding is to prove a hypothesis - which I believe is true in Series Seed, A and B - then the Series B is the last milestone before proving cash is the business’ limiting factor.
With seed money, founders test an idea to see if there is any potential of product/market fit. A seed investor evaluates many attributes of the company, but in the end is likely betting on the team and the dream.
With Series A investment, founders productionize the software and prove that customers might pay for the software at small scale. The Series A investor extrapolates from a handful of data points that a company might grow quickly.
At the time of the B, a small number of companies may have proven that thesis beyond doubt: either growing quickly enough to command a huge price (huge and unquestionable success) or proving the initial hypothesis isn't viable (certain failure). But most companies will find themselves having proven only certain parts of the go-to-market, but not all.
Series B companies may have some subset of key metrics in attractive ranges. They might have half of a management team hired. They might have some great customer success, but some churned, too. At this point, the business is too far evolved to simply sell the dream, but not far enough along to raise on the metrics.
That's the crux of the Series B. The company has one foot on either side of Geoffrey Moore's chasm. Can the business deftly place ten toes on the far side? The fundraising pitch must focus on why the company's momentum so far will make the leap inevitable.
In these cases, confident storytelling is the keys. The best book I've read on the topic is Resonate. A great pitch inspires investors, recruits and the press to believe.