On the Road Again

It’s been a busy conference season! With gathering and traveling back in full swing, we’ve been taking full advantage. In the last ten weeks, we’ve attended twenty (yes, I just counted) events across seven cities and were introduced to (no exaggeration, maybe an underestimate) more than a hundred new faces. Across these conversations, a few themes emerged. This is what we’ve been hearing out on the trail.

IRL is life. The only reason we’ve been attending so many events the last few months is because that is what has been happening . . . events! In person, see your face, handshaking events. It’s madness! Having spent the entire heart of the pandemic in New York City, it was initially truly jarring to start spending time around other groups of humans. I hate to overstate it, but things almost feel normal again. Actually, in some ways, better than “normal.” I don’t know about you, but I don’t remember having such a zest for event attendance before this. Of course, back then I was working in BigLaw and the “events” I was attending were, let’s just say, not quite as beautiful, joyful, interesting, or inspiring as the places I get to spend my time now (the clothes were also quite dull and the food sucked).

Virtual still has its place. This is not to say that the days of the Zoom event are over. We wondered if this would be the case, as I’m sure many of you have given how many people in this community host. But what we’ve found from our own virtual event attendance is that there is still value to virtual gathering. Our last two virtual gatherings—just today with Narra co-founders Victoria and Miggy Reyes on raising a friends and family round, and last month with speechwriting legend Felicity Barber on telling your story to investors—were oversubscribed. The caveat is that it has to be intimate and targeted and still allow for connection. With few exceptions, the anonymous webinar is dead and I’m wearing a red dress to its funeral.

None of us know what we're doing. This is the reality of starting a business. Most of the things you’re doing you have never done before, and some of the things you’re doing no one has ever done before. The more we speak with business owners (whether your business is a fund, a beauty company, the third company you’ve started, a super cool law firm . . .) the clearer we become that everyone is making it up as they go along. Logically, we must assume this has always been the case. The thing that may have changed a bit is that we’re more willing to talk about it. So next time you see some entrepreneur out there acting like he has it all together you can laugh to yourself knowing that he is either delusional and/or a total liar. And the next time you see a fellow entrepreneur make a mess of things, you can offer a few supportive words, because we’ve all been there and will undoubtedly be there again.

It's brutal out there . . . or is it? Being an entrepreneur is tough regardless of market conditions. There’s been quite a bit of buzz around the fundraising environment and it being particularly hard at the moment. The numbers show that this is certainly true, at least relative to the preceding couple of years. But as Amy Siskind, maven of distressed markets and GP at Causeway Investments, explained in this lovely/devastating post, these things are cyclical. I highly recommend you read the whole piece (will take 2 minutes), but I’ll send you off with a quote from Amy that I keep going back to and wholeheartedly agree with:

Approach the next two years knowing it will be more difficult than usual. Use your skills in persistence, combined with being open to reaching out to your networks for support. Yes, this period will suck. Meeting up with your fellow founders for a glass of wine, game of pickleball or whatever to compare notes and war stories will give you the affirmation and sisterhood to make it better.

Meeting, wine, pickleball, swapping stories. Sounds like my summer to do list.

--Jessie Gabriel

This website may use cookies for functional and performance purposes. We do not sell your information to any third parties. By continuing to use this site, you accept our use of cookies. Please read our Terms and Conditions and Privacy Policy for full details.