The (potential) tyranny of fundraising

Raising money is hard for a bunch of reasons. You have to clearly articulate your vision for a business that may be non-obvious. You will invariably suck at this at the beginning, and need to do it many times to distill the just-right way of communicating your profound message succinctly. And once you nail that, you will almost certainly need to deliver this pitch dozens of times to find the right investors to partner with who share the same passion for the vision that you do. Having raised money many, many times in my career, I can attest to the fact that it is alternately invigorating, exciting, gratifying, frustrating and exhausting.

But there is one rule I’ve always followed that has enabled me to both raise well and to raise from great partners: being transparent and authentic about exactly what it is I am excited to build. But in my time as a venture investor, I’ve encountered more than a few founders who feel that they need to calibrate their pitch to a specific audience, in order that their message in that particular pitch will be well-received. Sometimes it is making the business vision seem more grounded such that it “just makes sense”, in order to avoid questions about the idea being too pie-in-the-sky and risky. Other times it is the converse, adding layers of futurism for a pitch that is really just a sound idea to help solve a known problem better. In both cases when pressed, neither founder persona feels great about their pitch, but feel that this is what they’re supposed to do in order to enhance their chances of raising money from a particular investor or fund.

I am here to tell you that this is always, ALWAYS a mistake. What makes founders special is THEIR vision, THEIR passion, and THEIR energy to make dreams come true, whether grand and expansive or narrower and highly-scoped. Not every business needs to be a deca-billion dollar swing-for-the-fences enterprise, nor should a highly aspirational founder with a wacky, seemingly impossible idea feel hemmed in by the need to tell a “safer” story to raise money. Investors exist for every kind of business a founder might want to build, and a key part of the founder’s mission is identifying those just-right investors to help them pursue their vision. But by all means, pursue fund-raising this way, not by shape-shifting to try and make an investor like what they hear.

Building a business is insanely hard, and building a great business is insanely hard, takes a long time and requires a cascade of miracles to achieve. But make no mistake, you should be raising money from those who are authentically excited by what you are authentically excited to build, full stop. And if you ever feel yourself drifting into the land of “telling them what they want to hear”, stop yourself, recalibrate and tell the real story of your vision for the future. And if they’re the right kind of partner for you, you’ll know soon enough. Life is too short to start out misaligned with your partners from the get-go. Don’t do it.

managing partner @iaventures. working @thetradedeskinc @transferwise @signifyd @octanelending @memsql @robinhealthco @ethyca_. alumnus @UMich @Columbia_Biz