🤝 Recruiting the first team member
T = week 8
Note: This article has been updated to correct earlier formatting errors.
“Hey, I hope you’re not offended, but I redid one of your wireframes.”
The new wireframe in front of me was gorgeous — it was intuitive, bright and clear, and somehow avoided the Windows 98 feel that is the hallmark of my own forays in design.
“Whoa, this is amazing! How long did this take you?”
“A few hours; I couldn’t help myself.”
When — unsolicited — someone contributes real work, it’s a good indicator that they might genuinely care about the problem you’re exploring. And if their work is a Mt. Kilimanjaro better than anything you could have done, it's a good indicator you should take that interest seriously.
Even before this moment, I already wanted Heather to join my nascent start-up project. Heather had been tutoring me for several weeks in software design, and we liked working together. Beyond strong design skills, Heather has domain knowledge from working on an onshore-offshore (Singapore-Taiwan) team producing education software. She also speaks Chinese, and has spent a lot of time living in Asia.
Most importantly, Heather and I are close friends. We grew up 5 minutes from each other in Cleveland, OH and then both went to the University of Chicago. We trust each other, we have similar values, and we love hanging out.
And so, after our call, I wrote an email. I wanted 2 contradictory things. One, I wanted to woo Heather to join the project by projecting a sense of direction, purpose, and energy. But, two, I wanted to give Heather multiple ways to say “no” or “maybe” or “I only want to do a little.” I worried that Heather might say “yes” just to avoid hurting my feelings. And that’s not a good recipe for the start of a partnership.
Luckily, Heather was excited to jump in (*cue celebratory fist pump*). And so we’ve been working together since.
Another benefit of our partnership is that Heather lives in Taiwan. So, we are our own experiment in offshore collaboration.
But being 13 hours apart isn’t all gravy. Because we can only meet late at night or early in the morning, Heather and I are both a bit sleep-deprived. We have found it hard to carve out wide-ranging creative collab sessions. And because we both live in tight 1 bedroom apartments with partners who don’t work with team members on the other side of Earth, sometimes one of us has to be silent to avoid waking up our sleeping partner. So our live meetings sometimes consist of Heather monologing as I send replies and comments in iMessage, or the other way around. It’s strange!
We are moving slower than we would if we were both in the same place — this is a tradeoff. If Heather and I didn’t enjoy the time together, this tradeoff would be a deal-killer. Even still, in the near future, I’ll probably need to hop on a plane to Taiwan, or Heather will need to jump on a plane to the US.
In the meantime, we are trying to do as much communication as possible asynchronously. For example, we are traversing 50 Questions to Explore with a Potential Cofounder, a great alignment tool from First Round Capital. But instead of answering the questions in a live FaceTime call, Heather and I each record 3-5 answers per day in video recordings. This allows us to focus our live communication time on just the things that need high-frequency back-and-forth. Loom, Miro, Apple Notes, a shared Google Drive folder, Slicing Pie, and iMessage are the other tools of our trade.
One regret: I do wish I had better documented my first month or so of work. I spent a solid 1-2 days to bring Heather up to speed on where everything lived and to translate sticky notes I had placed on my apartment walls to digital Miro notes. Not a huge hassle but something to consider early. If things go well, you’ll be onboarding someone at some point!
Bringing another person into a start-up is risky. Why does it often make sense? Based on the literature I’ve surveyed, here is my distillation, in order of importance:
Camaraderie: Working on a solo project is, candidly, very lonely. You’re in a bubble praying you aren’t wearing a metaphorical tin foil hat. So being with another person wearing the same tin foil hat is nice.
Decision-relief: A remarkable amount of the “work” you do as a startup founder is answering the question: “what is the single best thing for me to do today?” The advantage startups have over corporations is that they can move faster and adjust on a daily and hourly basis. But it's a blessing and a curse. Letting another partner share decision-making can reduce your own decision fatigue, and you can reinvest saved brain muscle in other areas of the business.
Decision-relief doesn’t just come from a partner having wisdom or smarts. You ideally want your partner to have a strong compound of initiative and stress metabolism. This is probably the single most common piece of advice I’ve heard around cofounder selection. You don’t want to manage your partner! You want them to co-lead.
Insight: Mentors, books, podcasts are all great. But the place where insight matters most is inside the problem space. I don’t mean the “problem space” in a general, broad sense but at the atomic level. And no mentor — no matter how wise — can be at that atomic level with you, listening to every interview, and connecting all the tiny dots that separate a general idea from a real product. You can try to do this yourself. But you’re human. And you’ll miss things. (maybe you won’t, but I sure do!) When another set of eyes and ears are synthesizing the research with you, you increase your shot at product-market-fit.
Ability: No matter how talented, you don't have every skill. So it makes sense to bring on team members with diverse (and ideally broad) skill sets.
For startups, there is so much to do that it often doesn’t make sense to hire someone who can’t be exceptionally productive across a lot of domains. How many times have you heard an early start-up employee say, “I wear a lot of hats!”?
Obviously, there are fantastic people who do one or two things amazingly well. If someone has a “spike” in a particular skill set but isn’t a “wear a lot of hats” type person, it's better to hire them on a contract basis for a bespoke deliverable rather than bringing them onto the full team with equity.
The core of this point is about the efficient use of capital. At a large company, highly specialized employees can be working on a continuous basis because there is enough specialized work to do. This is probably true for medium sized companies as well. At a small company, there isn’t enough specialized work yet, which leads to “lumpy” contributions from highly specialized team members. This “lumpy” contribution typically leads to a poor equity-for-value tradeoff (e.g. the start-up “spends” its equity capital inefficiently).
There are obvious exceptions, particularly with technical hires. There is always enough engineering to go around, so you typically don’t have to worry about lumpiness there.
Throughput: 2 people should be able to do at least twice as much work as 1 person. New teammates help you move faster, and experiment more efficiently.
Bottom line: it's amazing to have a teammate!
If you’re interested in learning more, I recommend the following episodes from YC’s How to Start a Startup: