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August 21, 2021 4 min read

Here’s something I never thought I’d be doing: signing away a huge portion of my start-up’s equity — essentially getting married — to a woman I’d never met. But last month, I did just that: woke up, ate breakfast, and agreed to tether the future of my company to a person who exists (so far) only in the Zoom portal of my computer. I brought on a co-founder during the Covid pandemic, and it was the best move I’ve made so far.

Am I nuts? Well, it depends on who you ask, but I think the real answer is: yes, in a way that the success of a company absolutely requires. Building a start-up means that you have to be not just risk-tolerant, but chaos-seeking: there’s nothing about the process (leaving a steady paycheck, creating something out of whole cloth, raising money, teaching yourself 10 new skill sets) that sits well with people who are not out-of-the-box thinkers.

But most people choose fairly early on whether they’re going into this battle as a battalion or as lone warriors. They decide they need to be solo founders, to have the freedom to make every decision, or that they want to be part of a team, to have the security of someone walking beside them.

I didn’t choose, really. There was a company I wanted to build, and I didn’t know anyone who had the right skill set and wanted to build it with me. So, I set off by myself, armed with the famous last words of all people who’ve been fairly successful in the professional sphere: “How hard could it be?”

The answer was: well, you know already. Anyone who watches the birth of a business can see how closely it tracks real labor: everything takes longer than it should, everything hurts, and you can easily find yourself pacing, talking to yourself, not wearing pants. I knew there was something beautiful on the other side, but I wanted a partner who could pace with me. I had been laboring for a year, and I knew that, while I certainly coulddo it alone, the thing that I could build with someone else would be bigger, more beautiful, more useful to all the people I wanted to help.

And then I met Monika.

Well, “met” is a strong word. More accurate would be: I asked my network for recommendations for great Operations people, got her name, and asked if she’d be willing to chat via Zoom to help me flesh out what I was looking for. She was happy to help talk me through what I needed: someone to be the quantitative, steady balance to my racing creative brain. Someone to refine my “yes, and” ideas into an executable product roadmap. Someone who loved what I’d already built and wanted to make it a household name.

We realized, right around the same time, that the person we were talking about was her.


I’ve never weighed a decision more heavily (and I’ve been married, so that’s saying something). In the “pro” column: she’s a brilliant Northwestern MBA grad, was the first full-time hire at a rapidly acquired start-up, has clear financial acumen, a love for my mission, and very good ideas about how to improve the business. In the “con” column: I’d never met her in real life. She lived in Chicago, so even if we wanted to break social distancing rules (which we didn’t) we were relegated to Zoom and FaceTime. How good a substitute for human interaction could those be? The world felt like it was on fire, like anything could be true tomorrow. How could I ask this person to give up her job in the middle of such uncertainty? How could I bring her into the inner sanctum of what I was creating, when we’d never even had a glass of wine together? There was so much uncertainty; it felt a little crazy to intentionally create more.

The interview process stretched over several months, and we worked through everything from nitty gritty margin movement to sweeping plans for social change. The calls were after her workday, when we were both exhausted, but I looked forward to them. She gave me energy. And I saw what I was looking for: she listened carefully and wasn’t impulsive. She wasn’t afraid to push back when she saw a hole in my argument. She was friendly and hard to rattle, and she was ready for a big challenge to sink her teeth into. Most importantly: she was a builder, someone who lived for making things work. Perhaps because we weren’t physically together, because it felt odd to while away time while talking to someone who lived in our computers, we were focused. We got stuff done. Every time I got off the call, I felt that particular buzzy high that comes only from creation.

So, I decided: WiFi was good enough. When you believe deeply in what you’re building, it makes you braver. You’re less willing to sacrifice time and energy postponing a decision you’ve already made in your gut. Our mission, with Small Packages, is to forge connection, to pick up the dropped balls and missed signals. I felt that connection with Monika right from the start. I knew she was the missing piece I’d been looking for, and that the truly crazy move would not be bringing her in to a company where she would add enormous value, but instead to let the global uncertainty and physical distance prevent me from making the right decision.

It turns out, the only time you feel really frustrated by never having met your co-founder in person is the day you make it official. We both wanted to physically toast to the step we were taking, to recognize the moment in a way that honored its hugeness. But there are a lot of things we have left to do together: making Small Packages the go-to gifting service for busy people everywhere, and taking a huge bite out of the national loneliness epidemic.

We’ll just have to add champagne toasts to the list.