“How does she do it?” With love. And with others.

Lately I’ve been getting feedback like this:

There are only so many times I can answer the question, “Do you ever sleep?” (yes, a lot) before my response starts to feel disingenuous or coy. I’m going to share here, for the dozen people who care, the most brutally honest answer to the question of, “How you do it?” by showing you, literally, how I [sic] have worked [sic] over the past seven years.

Figuring out how something in the present came to be requires revisiting the past. So I went through my files, photos, and emails created over the same week and a half period (February 5th through 14th) over the last seven (2011–2017) years and, like an Arrival/Memento mashup, will now give you a glimpse of how the sausage is made.

Buckle your seat belts, friends, because we’re going to push the boundaries of Medium as a time travel machine.

(For those of you not following along at home, the “sausage” I refer to is our business Switchboard; XXcelerate Fund, a debt fund for Oregon women entrepreneurs; and Business for a Better Portland, a new type of chamber of commerce.)

2011

On February 5, 2011, Greg visits Andrew (my husband) and me in Philadelphia. Greg can sustain 18 hours of uninterrupted conversation. Sadly, we cannot. So we schedule a diversion to the Mercer Museum:

By 1897 handmade objects were being discarded in favor of new machine-made goods. Historian and archaeologist Henry Mercer (1856–1930) recognized the need to collect and preserve the outmoded material of daily life in America before it was swept away by the Industrial Revolution. Mercer gathered almost 30,000 items ranging from hand tools to horse-drawn vehicles and assembled this encyclopedic collection in a system of his own devising.

I plan the visit poorly and doublebook a conference call of the Reed Alumni Board at the same time. So I do what almost all of us have done who have served on a non-profit board: I stick in my headset, mute my line, and take photos of anvils and old mail boxes in a six story castle.

Experiencing the universal Post-Museum Ravenous Hunger we tuck into a convenience store for lunch. I complain about how useless my service to the college feels. “They want you to donate. And it sounds like you want to feel useful,” says Greg.

We hash out what useful student and alumni interactions look like (spoiler alert: jobs). I had been trying to solve this absent network effect for years, sending an annual complaint to the college president and roping my classmates into various schemes that involved spreadsheets and call quotas. The following day I write an email to three dozen alumni friends with a final plea: “Can I ask you to join the crazy train just one last time?”

2012

During the same week a year later, Reed Switchboard is now a thing. Exactly a year after the trip to the Mercer, I visit campus to share it with students. I ask, “How can alumni like me be useful to you?” and fill pages of notes with their answers. I will later learn these are called “customer interviews.” I take out a classified ad in the weekly email newsletter directing them to our modest Wordpress website, where alumni are standing by waiting to help. I buy 2,000 business cards for $30 and slip them in to students’ mailboxes. I spend a lot of time in the coffeeshop with barefoot customers.

A few days later, on a road trip to Santa Barbara, Amanda and I hurl Cheetos on to the roadside, drink wine from paper straws, and dance to “When You Were Mine” in a rainstorm sucking on cherry ring pops. We design a Valentine (“Reed alums love Reed students, today and every day.” -Reed Switchboard). We print them on red paper and FedEx them and bags of Hershey’s kisses to be given away to seniors. The next day, one of the world’s top wedding photographers will shoot my calligraphy portfolio as a trade so I can continue earn money while exploring what Switchboard might become.

2013

During the same week, a year later: My co-founder Sean and I met, miraculously, on Twitter (full story here). We take the plunge and meet in person for the first time. I fly from Florence, Italy. He arrives from California. We spend our days and nights on campus, refining the product and talking to students. Sean indulges my antics (and apparent love of ring pops). To spread the word about Switchboard during a campus networking event, Brent has the genius idea to dress up like Gumby. Students and alumni write down one thing they can teach and safety pin these notes to his costume. He takes a picture with the college’s president. This is one of our first marketing efforts.

I engage in an epic correspondence with Adam Lisagor of Sandwich Video who agrees to shoot our product video for a charitably huge discount. We hold a casting call on campus. A flag hangs outside of the cafeteria: “Things we produce. Beautiful things. Put them out in the world, and can be pleased, and can be proud of what we can make.” Amanda’s dear friend is dying of cancer. She sends me to buy him the most expensive bottle of scotch and deliver it and a note of farewell to his door.

Kieran (who has been our director of marketing since then), Sean, and I go to the penny arcade to celebrate because Kieran is still underage. Later that week we embark on an insane endeavor to send hundreds carnations and valentines to students. A small army of incredible women mobilize. We pull consecutive all nighters and take over the library lobby with burgers and spreadsheets. Boys stop by and think we are straight up crazy. The result is beautiful: smiling students walking around campus flowers and love letters in their hands.

2014

During the same week, a year later: we’ve been accepted to PIE. Sean and I pay ourselves for the very first time, $1000 each. We send Brittany handwritten updates on our progress. She will go on to introduce us to Joanne Wilson, one of our first investors. The designer Jessica Hische (divine intervention) helps us redesign the site. We launch it while I am in São Paulo for a friend’s wedding. Later that night I will get kicked out of a karaoke bar.

2015

We sign our first office lease. We are now working with colleges and universities around the country. I meet with Patrick Maloney for the first time, who will go on to help us conceive of XXcelerate Fund. I share with a friend my favorite article by Lewis Hyde, “The Gift Must Always Move.” I visit the Canon Beach History Museum and learn about Mary Garritse, a remarkable and tenacious mail carrier who, on her horse Prince, made her daily rounds with “only a jacknife to defend the mail.” Mary becomes my North Star.

2016

In a past life, I was a food writer in Philadelphia. I had a tradition every Valentine’s Day, which was to visit the home or restaurant of Cypriot Chef Konstantinos Pitsidilles (here is the first, in 2006) and write about his journey towards the dream of one day opening his own restaurant. The first meal I had that he prepared, 11 years ago today, was a revelation. It was culinary talent on a scale I had never experienced, and have yet to again. The food went directly to my heart.

This February, I’m back in Philadelphia to visit my husband. (This is the husband whose modest professor’s salary has made any of what you see here possible). His colleague, Marina, makes us pancakes and tells me about the tradition of genizas in Cairo synagogues (which is basically what I have done here: a layered record of time through ephemera).

We celebrate Valentine’s Day at Kanella. Konstantinos has finally achieved his dream: he has his own beautiful restaurant on the waterfront. We hug. I cry eating the saganaki. He arrives table side with a scrapbook and takes out the yellowed newspaper clipping of the very first article I wrote.

“You were the first one to write about me. You were the first one to know what this would become.”

We learn that our first call-to-action for (then) PICOC was successful and helped the Sons of Haiti raise $9000. We send a celebratory email to our supporters with Intisar’s beautiful photography. Jenn visits and we conceive of “Sex & Startups” while attending a stamp show with septuagenarian veterans.

2017

And now I write you at the end of the same week, a year later. This morning we brought on our first US independent school as I prepare for a west coast sales trip. Tim is sending Valentine’s Day photos to our incredible partner schools. Sean and Tara are about to ship our most major product update yet.

Today, Business for Better Portland will announce our 50th Founding Member company. Earlier last week we met with Congressman Blumenauer.

Last week, we launched XXcelerate before hundreds of people during Portland Startup Week’s Innovate and Advocate. Paige made brownies and gluten free cookies from scratch. On Saturday, we had a photoshoot at Wieden + Kennedy thanks to Rob and Kate, who has been a steadfast ally since my days in the building at PIE. I type this working alongside Renee, who joined the fund as our COO. She came up to Astrid and me at the Oregon Capital Scan event and said, “This is going to sound crazy, but I have experience underwriting loans, starting a fund, and incorporating a non-profit.” We hired her on the spot.

Last night, Ashley and I saw Sign o’ the Times at the Portland Black Film Festival before I headed back to the office. I left feeling like if I could bring an ounce of whatever energy Prince brought to his work I might be able to look back and consider my life well-lived.

And yet, living this life is a profound privilege. On Sunday, Amanda and I went to a vigil for Quanice Hayes, a black teen shot by Portland police. Heart balloons marked where he was killed. None of This, None of All of This, makes sense.

And yet, always: love.

Well.

Most of you will agree that none of these activities are enumerated in The Lean Startup. This is not the picture of a unicorn factory, or how chambers of commerce and debt funds are created.

So what are the constants? There is no “doing.” Instead, there is an outpouring of generosity from a community of collaborators. Infinite gestures of kindness and compassion far beyond what is captured here. Living off of the screen and in the world. Making use of limited resources. Beauty, grace, delighting in the everyday. Reminders of what hard work and tenacity look like, and of our own mortality.

I’ll share my top 14 lessons from the last seven years, extracted from this one window of time.

  1. “The best way to complain is to make things.” -James Murphy
  2. Frustration comes from not feeling useful.
  3. We must buy the most expensive bottle of scotch. We must go to the vigil. May we all have a friend who teaches us this.
  4. Every museum is a temple to What is Possible.
  5. You can start a company with box of $30 business cards, carnations, and a Gumby costume.
  6. When your friend is getting married, fly to Brazil for the wedding. It’s okay if you get thrown out of a karaoke bar the night of your product launch.
  7. Trust your intuition. The Cypriot chef in the hole in the wall South Philly restaurant will go on to create the best restaurant in town. And you knowing this first is what you can tell investors when they ask, “What is your competitive advantage?” You will say, “The saganaki tells you everything you need to know.”
  8. Every now and then, write it by hand.
  9. The men who consistently and unfailingly help women are saints walking upon this earth.
  10. If Mary, the most remarkable mail carrier, managed to deliver the mail against all odds with only a horse and dagger, You Can Do What You Must Do Too.
  11. Prince.
  12. Never alone.
  13. Always with love.
  14. The gift must always move.