I'll Fund a Startup n00b But Here's How Not to Look Like One

It shouldn't be the cost of a ticket, but knowing the inside baseball makes playing the game better.

Years ago, I got invited by Steven Messer to join him and his co-founder (and brother-in-law) Tad Martin, two very successful NYC founders, out on a bike ride up the West Side Highway and up 9W over the Palisades. It’s a pretty standard route for hundreds of experienced road cyclists every weekend morning.

This is before I ever did a triathlon and before I ever even had a proper road bike. I had an aluminum commuter bike and I’m pretty sure I was wearing jean shorts at the time. I’m not going to argue whether or not jean shorts were ever in fashion, at that time or at any other time, but I’ll at least concede that they weren’t appropriate cycling gear for a 60mi ride with experienced riders.

But how was I to know? I didn’t have any friends that were into this kind of cycling at the time—and for whatever reason it’s something that people in their 20’s really don’t do that often. Maybe it’s because they’re not making enough money to fall down the rabbit hole of expensive carbon fiber road bikes and all the various gear that you can end up purchasing. Whatever the reason, I had no one who could warn me about how goofy I was about to look.

To my credit, I did actually keep up with those guys on the way up—but on the way back I just let them go ahead, leaving me to amble home, sweaty, sore and very uncomfortable in wet cotton.

That was the very last ride I did with those guys on that bike and in that gear. I went out and bought a mid-tier carbon bike, which I actually still use and race with to this day, thirteen years later. So, while I spent more than I thought a bike should cost, six half Ironmans, eight Grand Fondos, including two international ones, and countless other triathlons and duathlons later, I more than got my money’s worth.

I feel like that’s like a lot of things in life—where the more you spend on something doesn’t always give you a better experience, but there’s probably some baseline you want to spend not to have a subpar one.

It wasn’t long before I was waiting on future rides at the tops of hills for those guys to catch up to me. (I actually think it might have been the very next ride or two once I had a decent enough bike and a real pair of bike shorts.) Just a few years later, I finished with the 63rd best bike time among all 3200 triathletes in the NYC Tri.

I was pretty athletic and I certainly had the potential to be a good rider—all it took was some exposure to people who were more experienced with this hobby. Many of these things weren’t even a function of doing homework on how to be a good cyclist or about working out—but more like “what’s typical”?

The same is true in the startup world, where there are definitely things that signal that someone is pretty unfamiliar and inexperienced with this space. As insiders, we feel like the community is super open and transparent that we can’t imagine not knowing what someone’s pitch should look like or how someone could miss out on the language of fundraising, but actually, it’s super easy.

Most of this stuff fits into the “How would you even know?” unless you grew up with friends or family who had raised money from VCs before, and we all know what that group looks like demographically. In fact, there’s little written about some of the behavioral norm stuff, so while you can read endless articles about SAFEs vs convertible notes, how are you supposed to find out that putting LLC next to your company name in a pitch pretty much kills your fundraising.

Some you may be reading this like, “What?? But that’s the name of my company!”

Yes, yes it is… but that’s also the startup equivalent of putting “MBA” after your last name on a business card. Now, why do we think some graduate degrees are deserving of professional display and others aren’t? I don’t know—but if you’re in any area of the professional world, you can see that it’s just not something MBAs do. Doing so is just a little “off”.

With LLCs, you get two strikes. One is that if you’re going to take venture capital funding, you’re going to convert your LCC into a C-corp. VCs don’t want the passthrough of your income into their fund for tax purposes. So, you’re pitching a thing that’s going by the wayside.

Two, a pitch is a branding exercise. You’re marketing your company. Do you see Apple marketing its iPhones as being made by “Apple, Inc.”? No, it’s just Apple. You don’t put the full legal name in the marketing.

There, now there’s one less way for you to look like a n00b. There will be others—like don’t ask a VC to sign an NDA. That’s at least one you can look up in lots of places as to why—but you might not run into it before the first time you pitch.

I try hard to lower the barriers to pitching and getting your fair shake—no need for warm intros, for example. You definitely don’t have to know all of the traditional startup things ahead of time when you pitch me (as long as you’re in NYC), but I’ll still say that it’s in your best interest to see how other people pitch first and to talk to as many experienced founders as you can. Founders are generally pretty helpful to other founders. Running by what you have to other folks in your industry working on non-competitive projects can be enormously helpful.

This is partly why I do my #notapitch series—to test run an idea before it ever counts as anything close to a real pitch. You give me a couple of minutes on what you’re working on and I’ll give you some directional feedback back.

And if you don’t have those connections, there are lots of conferences and pitch events in startup cities that can provide you access. In fact, if you’re a real first-timer and you find a startup conference near you that you’d like to go to, consider reaching out to that conference to work with them in organizing an event or track for first-timers. To be honest, having some kind of primer on fundraising or being a founder before such a conference works for both sides. It will make the experience better for new folks but also for the pros who don’t get a lot out of being hit up with what should be better-practiced pitches.

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