Notes from a First-Time Founder: Fundraising Night Sweats

A few months ago I was talking to a friend, a start-up CEO, about how I was dreading the fundraising process I am about to launch into for my company, To&From. His response startled me. He said something to the tune of “That’s good - believe it or not, dread is the healthiest emotion leading up to fundraising.” I’ve thought a lot about that statement and why this might be true. And what I’ve landed on is that “dread” - this feeling that combines fear with anticipation and ultimately, the unknown - is ultimately what fuels excellence and drives many of us towards success. Let me explain.

Late last year, with a very small team and an even smaller budget, To&From launched our first product - a closed beta for a couple hundred people who are close to us. This first experience was always meant to help us prove our hypotheses and more importantly, to inform the next experiences we wanted to build. We thankfully had amazing friends and family join us on this journey - and they were? lucky enough to find incredibly thoughtful and targeted gifts under their proverbial trees in December. While I am thrilled that we were able to provide some magical gifting moments, what I really wanted was raw and unfiltered feedback or, as my CTO Dustin Goodwin says “we want people to tell us if the baby is ugly”. Now, of course, all babies are adorable so please understand in this context baby = business. So as we invited the first users into our gifting network, I felt that same sense of dread that I now have about fundraising. “What if people don’t like the experience?”, “What if it doesn’t work?”, “What if we find out there isn’t a market for better gifting experiences and I’ve made a massive mistake?” were all things I woke up in the middle of the night sweating and thinking about. “What if the baby is ugly!” Guess what - none of those things happened. Sure, we uncovered gaps, but also expanded our idea based on what we know. There are also things I would do differently today, knowing what I now know. But, guess what -? the baby wasn’t ugly. It was, in fact, just a baby.?

What we heard were so many amazing things about the potential of this To&From. In addition to solid critique of where we could improve the experience, we heard hundreds of creative ideas about the problems we could solve by building an Intelligent Gifting Experience, one that uses Gifting Intelligence, as we call it, to power an Ecosystem of experiences that remove the everyday friction in the modern gifting experience. We also heard a resounding chorus of “this team can do this”. This feedback pivoted my mindset from dread to anticipation and, dare I say it, excitement about the fundraising process.

Why? Well, three things really. First, I know this idea is good. We’ve tested, validated, and talked to hundreds of gifters, giftees and brands. Gifters are excited to have better tools to find and deliver the best gifts to the important people in their lives. Giftees are excited to share more about themselves in order to receive better gifts. And the DTC Brands we have talked to are incredibly excited to have a platform that is focused on driving new customers to their sites, with a long term focus on turning that Giftee into a customer for life.?

The second pivot point is our team. In a word, they are kick-ass. Remember the part about the small team and a smaller budget? Well, this small team has killed it. With no full-time salaries, and only a promise of what could be if we do this well, our team is working endlessly to bring great ideas and execution to the table. Given the press’s obsession with the “Great Resignation”, I certainly know that my team could be doing a lot of other things - for more tangible rewards than I can offer right now. Their belief and commitment added more fuel, lighting me up for this fundraising journey and the chance to share our big ideas for transforming the consumer gifting market.?

The third change is within my own mentality. As I ideated and first started talking about this idea, I have struggled with communicating how big I believe the market could be for what we are doing. Part of this struggle was landing the messaging in a succinct way which we now have done, but part of it was allowing myself to fall victim to imposter syndrome. I have not doubted that I can build a great company and a big business; however, the endless drum of how hard it is for women to raise venture capital, had me in this state of dread. But now, with our first beta test behind us, and validated across these critical areas, I can’t wait for what’s ahead of us.?

So I ask you, what is your advice, who do you know that I should know and how do we make that introduction happen?

Wish me luck, I’ll let you know how it goes!

Bridget Johns, Co-founder & CEO at To&From

P.S. If you’d like to follow-along with our progress or if you’d like get in line to give and get great gifts, follow us here, join us on Instagram @mytoandfrom or join our waitlist at toandfrom.com/#join.