What Do You Do When You Don't Know What To Do?

Building in Public: How We Decided to Expand Pie From Chicago to SF 🌁

Pie is a social app for making friends. We are live in Chicago and San Francisco: getpie.app

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We had lively debates. Or maybe we didn’t debate enough.

Should we stay 100% focused on Chicago? Or launch a second market?

We noticed Pie growing organically in San Francisco, and we had a loyal cohort of early ambassadors using the product in the Bay Area. But a much more meaningful lift would be required to get the market properly percolating.

While Chicago—our first market—was growing nicely, a lot of our growth was rooted in spring and summer outdoor plans—where space is free and hope springs eternal. The question became: did we have enough momentum in Chicago to give ourselves permission to expand? Or would it be wiser to keep investing in our core market before adding market two? Meanwhile, winter was coming.

It reminded me of the debates we had at Bonobos about when to expand beyond pants. In retrospect, we went too early. (And arguably into the wrong category: swimsuits. Later, shirts would work better.) We also fumbled our way into divesting two experiments that became distractions, and the latter almost sunk the company due to the capital intensity: a women’s brand we incubated called AYR (now a strong brand and a great business); and an attempt at building something like Shopify in-house (which Shopify built instead, doh!)

To warn other entrepreneurs—and to protect my future self—from this kind of '“too much too soon” hypomanic overextension (that I have a predisposition for), ten years ago I wrote a missive about the perils of lacking focus in brand-building called Get One Thing Right.

The relevant section is this:

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A lot of companies don’t make it because in the process of trying to get many things right, they don’t get anything right.

Why are they in such a hurry?

A great company is a privilege, and it’s a privilege best earned through a singular product, not a collection of products. Entrepreneurs and creatives think about batches of products —creating an empire, or designing a collection. Consumers think about something they want or need right now — a singular product or item. Founders have dreams of a one-stop shop. That kind of thinking, applied out the gates at least, will often lead to a no-stop shop.

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And yet.

As we contemplated San Francisco at Pie, I found myself passionately and perhaps irrationally advocating for it.

Reflecting on my earlier learnings on focus, I wondered…

Maybe I’ve learned nothing?

As my dad Charley Dunn—a history teacher—likes to remind me, the Protestant theologian Reinhold Niebuhr once said:

Frantic orthodoxy is never rooted in faith but in doubt. It is when we are unsure about our own beliefs that we are most likely to be most dogmatic about them. — Reinhold Niebuhr, “The Self and the Dramas of History” (1955)

And so the decision on San Francisco began with the most serendipitous and questionable of inputs. I had a long planned PR trip to the Bay Area, and at the last moment invited three teammates to come—Marty, Gustavo, and Samir.

The mandate for the week was this: meet two dozen high-quality IRL creators who demonstrate strong interest in joining Pie’s Creator Fund, and we might just go for it.

Pie—whose mission is to defeat social isolation by making it easier to make friends—is stimulating an ecosystem of gig economy entrepreneurs who we call IRL creators. These are the people who bring people together. Our hypothesis is that by creating an economic incentive for the most determined and tenacious IRL creators to be able to invest more time and treasure in the communities they are building, we can empower them to turn their passion into an accretive side hustle, and maybe even make the leap to full-time. Think Uber drivers or Airbnb hosts—but make it IRL community builders.

Our top creator in Chicago is earning $100,000/year and now has equity in Pie. If this intrigues you—wherever you are—or might intrigue someone you know, check out our application at piecreatorfund.com. We’re actively recruiting creators in Chicago, San Francisco, Austin and Nashville—with the rest of the country coming next year.

The IRL meetings with IRL creators (see what I did there) went well. We met some impressive humans, including:

• Side of Stef: a social community founded by a digital influencer; Stef was once new to San Francisco and started hosting monthly meetups, that have snowballed into events like 1,000 people cavorting in a Christmas tree lot.

• Marina Plunge Club: just what it sounds like—jumping into the brisk waters of the Bay — started by a tech founder named Alex Schachne.

• The Coffee Club: turning local coffee shops into nightclubs with DJs and 150 revelers drinking coffee and vibing—started by raconteur and entrepreneur Simon Reznichky.

The (somewhat) scientific part of the decision-making came down to three inputs:

1. A desire to maintain rapid growth in the face of changing conditions in our first market — the idea of continuous growth being a forced constraint in startup discovery.

2. Twenty user interviews of IRL creators in the market, doubling as pitch meetings for the creator fund; seeding the ‘hard side of the market’ from the framework in The Cold Start Problem.

3. An early read on performance to see if the experiment was working and whether to continue investing in it, focusing on retention curves and benchmarking them against Chicago.

So how is it going?

For now, it’s cooking. While we’ve been mostly growing between 20 and 40%+ month-on-month this year, the Bay Area launch is driving our first ever 60% m-o-m pop.

We’ll see if that endures, and if it’s retentive.

Sometimes startups are like this.

There is not enough data to know what to do, so you get whatever quantitive signal you can. And then you also pay attention to the little Matthew McConaughey style “greenlights” as either a dreamer’s omen or a fool’s signpost for when to move forward. For when to make a bet.

In his book Greenlights, McConaughey defines his title word as moments or situations in life that signify a positive sign to "go ahead," "proceed," or "carry on," essentially representing an opportunity or affirmation to move forward on a path aligned with your goals and values; it's a metaphor for recognizing positive moments where life is saying "yes" to your direction.

I used to think it was crazy that I often secretly did this, until I noticed other entrepreneurs doing the same thing. Phil Knight’s Shoe Dog is filled with greenlights. Maybe deep down many of us entrepreneurs are mystics, or wannabe sorcerers or something.

The greenlight here was that serendipitously-scheduled PR trip to San Francisco, certified by the last minute, whimsical decision to bring the team. The PR reason for the trip was my fireside chat with Amanda Silberling at TechCrunch Disrupt. Here’s the conversation we had:

And then another greenlight. Backstage I told Amanda about what we were up to evaluating the SF market. She was intrigued, and mentioned she’d be interested to write the story on our Bay Area launch. Then she did. Here it is:

IRL social app Pie is coming to SF to make you less lonely

From that came a follow up podcast with TechCrunch:

Former Bonobos founder is rethinking social media

All this came from not knowing exactly what to do, taking a trip with the team, talking to people, trying it out, and seeing what happened.

I share this because maybe none of us really know what we’re doing?

Sometimes it’s searching for signs. Sometime it’s noticing what’s right in front of you. Sometimes the universe conspires.

Alright alright alright.