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How to be unreasonable (what’s next).

Six months ago (4/14/17) I met Paul Biggar for the first time.

I walked into our meeting intending to spend an hour brainstorming consumer product people who might make for good cofounders.

Three hours later, I walked out of the meeting completely convinced we were going to start a company together.

This sounds unreasonable, and everyone said it was crazy. We did it anyway, and during the six months between then and now:

• We started the company, fundraised, and set up an office.
• We hired (hi Stefi! hi Ian!) and are hiring more.
• (Most excitingly) We‘ve been building and testing things.

The last six months have prompted reflection on what enabled me to feel enough conviction to do this (and what nearly stopped me).

Know the shape of what you want

I have known for years that I wanted to have another startup. (Long story short — during college five friends and I had a startup that was a bad startup, but would have made a great reality TV show).

I knew I wanted three main things:

1. To do it with a deeply technical cofounder who cared equally about “15 years from now we need X” and “this pixel is wrong.”
2. To make software with a tangible connection to the real world and/or that helped other people make things.
3. To build an ambitious, high-growth company.

My intent was to spend more time at Lola and eventually return to HBS to find the right problem to solve, and the right person to solve it with.

Instead, I met Paul. It was clear he was the right sort of person, had an idea in the space, and wanted to make the same type of company. It would have been the perfect outcome of my plan, and it appeared ahead of schedule (and out of the blue). If you know what you’re looking for, it’s easier to recognize it when it arrives.

Say yes & de-risk

Instead of starting from a place of “I need to prove this is a good idea” I walked out of the meeting thinking “I’m in, unless something goes horribly wrong.”

We went through a bunch of experiences in the first few weeks to try to surface as many potential issues as possible:

• Early meetings. A lot of the beginning was just “can I see myself spending all my time with this person?” Our first conversation wove through a huge array of work topics (boards, finance, tech stack) and an array of personal ones. The answer there was yes.
• Founder dating questions. Since Paul had been actively looking for a cofounder, he’d come up with a set of questions that he’d answered, and wanted to see my answers for. We wrote independently and exchanged. Our answers are eerily similar. At the time I thought “yea of course they’re all the same, isn’t this what everyone wants?” In retrospect, nope, we’re just very aligned.
• Working together. Paul and I met on a Friday, and less than a week later he came to Boston for four days so we could work out of my apartment. After four days I was actually sad he was leaving (I am introverted; this never happens).
• Experience, skills, roles. Since I knew I wanted to start another company, I’d been focused on building the right experiences. I’d gotten to see Lola through the B, and Paul had gotten to see CircleCI through the B. We both knew what types of work needed to be done, and which work we were each suited to. We made a spreadsheet and discussed who would do what, and who wanted to be involved with what. It checked out.
• Reference checking. I always assumed I’d start a company with someone I knew/had worked with. Since we hadn’t, we both called previous people. Neither of us is perfect. What was reassuring was that the strengths and weaknesses we’d shared with each other were echoed by our networks. There were no surprises.
• Advisors. I checked with professional advisors. Friends and family are interested in keeping you happy. Professional advisors are often interested in what’s going to give you the best outcome. In particular, the team at Flybridge (where I’m an advisor!) was incredibly helpful and I’m delighted that XFactor was able to participate in our round.
• Shared interests. I have a running tally of unexpected things we have in common. It includes things like deep love of sandwiches, strategic coop board games, the video game Geometry Wars, Taylor Swift, and in case of terminal illness a desire to fly in a squirrel suit. It doesn’t really matter to me what the shared interests are, I’m just happy we have them.
• Coaching & continual improvement. Since we were new to each other, we didn’t want to take anything for granted. Rather than waiting for problems to come up, we immediately started working with Semira at Innerspace for cofounder therapy.

Most of my hunches from the first meeting were right, but the de-risking process helped me learn more about me, Paul, and our company. Make yourself prove why you shouldn’t do it, rather than why you should.

Support Structure

Making these changes was not simple, particularly not with everything else going on. Paul had the benefit of time off after CircleCI to regroup and decide what was next and was impatient to start. I was still in the midst of a bunch of other things and felt like I had to run 100mph to keep up with everything.

Tom is the best partner one could ask for. I could not have picked a worse time to do this for him either, and he co-signed almost immediately. Every low moment I hit where I had to say “I’m sorry I made our lives complicated” he said “this is what you need to do, and we’ll figure it out.” Everyone I tell this story to is impressed by his poise and unconditional support. If you want to be unreasonable, the people nearest to you have to be supportive.

He was not the only one who supported me through this. I started to write individual thank you, but I became fearful of missing people. That said, this would never have happened without my friends.

This almost didn’t happen…

I’m writing this post mostly because in retrospect it looks unreasonable and cool and like I’m great at risks, but in reality it almost didn’t happen at all.

Before Paul emailed me directly and I agreed to meet, I’d gotten an email from my friend Thomson:

…Paul is a friend of mine/former coworker at Lookout, and he’s looking for a founder/CEO for his next company (he was the founder/CTO of CircleCI). He’s looking for a product-minded person interested in culture/team building, so you came to mind. I know you probably have a good thing going at Lola, but LMK if you want an intro! …

I replied:

“Ha, you have me pegged exactly right — I love this… Unfortunately, I’m not looking to leave right now…”

I turned the intro down for two reasons:

Timing. I was very busy. This summer I also bought a house, wrote the first version of an essay book, and got married. In retrospect, six months earlier I would have taken the meeting without a thought, and six months later I would have as well. It would be crazy to miss the perfect opportunity because it showed up six months off schedule.

Fear. My heart leapt the first time I read the problem description. I knew it was a thing that fit my space. I turned down the meeting because I was afraid of wanting to do it and not being able to.

I like to think of myself as being risk highly tolerant. It surprised me to see that timing (and only six months!) could throw me so far off. I also can’t think of many opportunities I turned down for fear of failure.

Everyone would have looked at that choice and said it was reasonable, but I would have been wrong. The unreasonable yes was the right answer.

When you’re looking at something and it looks perfect but seems impossible, try to get yourself to a place where you can do the unreasonable yes.

1. If it’s the right shape, say yes (even in your head!) and then figure it out.
2. De-risk as much as you can.
3. Enlist support structure.

So, what’s next?

This has been six of the best and most challenging months of my entire life. Normally I write about transitions before they happen, but since we’re six months in there isn’t much else to say. The last six months have helped me learn about risk taking (both for myself, and for the company).

Now, we get to continue building the product and the company!

Excited about this?

We want to make it possible to build a complete scalable app in an afternoon. We’ll make it 100x easier to build applications and bring the ability to write software to a billion people. You can learn more about what we’re doing here.

We’re hiring for design, engineering, and operations. Interested, but afraid it’s unreasonable for where you’re at? Get in touch and we’ll try to help you figure it out. You can email me or my DMs on Twitter are open.