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The Six Types of People You Meet on a Cross-Country Train Trip

on Jan 12 2018
Chief Storyteller @ Wefunder


We'd been on the train a week already by the time we got to New Orleans. After rolling our way through four cities, countless meetings, and a truly alarming amount of BBQ, the beds in the Big Easy felt a little softer, the beignets just a little sweeter, and our team reveled in it.

After a first night spent in and out of various jazz clubs, we greeted Friday morning with some resistance. Some of us were cranky. Some of us were hungover. Some of us were both (I was both).

We’d met what felt like a thousand founders over the previous week. Even though most of them couldn’t have been more welcoming and friendly, hearing the challenges and the ups and downs from that many people can be taxing, particularly when these meetings take place in cities most of us had never been to.

So we needed a boost. We needed a jolt, something to kick us back to the mindset of why we went on this trip in the first place. 

We needed the Bagel Boy.

He bounced through the front door with a brown paper bag full of bagels and a head brimming with anecdotes. The Boy has baby blue eyes above sharp blond scruff, a welcoming sort of face that people are just drawn to. 

He sat down and shared his story from the beginning, back when he was just another employee at a bagel shop in New Orleans. After his shifts ended, he saw dozens of unsold bagels being thrown away every night, so he started a bike delivery service around town for his friends. Those friends told other friends, a classified was posted online, and less than a year later, he racked up so many customers that he could cut out the store and start making and delivering his own product.

A minor detail: he’d never made bagels on his own before.

The Bagel Boy in the flesh.

By this point in his visit, our entire team was sitting around the Boy, vigorously consuming equal part bagels and stories. Part of me thinks it was his voice that drew us in, a deep surfer-bro drawl that preached self-deprecation and confidence within the same monotone, but it was more than that.

As the Bagel Boy told us about waking up at 2 a.m. every day to cook and deliver his bagels, or how he figured out how to ship them across the country, or his philosophies on accepting mistakes as a small business owner, you could physically see our team perk up. This was it, our proof of local entrepreneurship on a scale you rarely find in San Francisco, a thing we so easily lose sight of when working in a Silicon Valley office every day. 

Ten days on the road is a long time. It can feel even longer on a train, the repetitive noise of the tracks and the consistency of the scenery scheming together to slow the minutes and hours down. 

The legs of our trip always felt quicker, though, after we met someone like the Bagel Boy -- a person devoting incredible hours to creating a company from scratch, a person who reminded the 12 of us, again and again, why we started Wefunder in the first place.


There are some people who look exactly like their chosen profession. Wefunder’s CTO, Greg, binges high-level video games and once wore a T-shirt with a kitten surfing on a pizza underneath a T-Rex Christmas sweater to a restaurant with a strict “business casual” dress code. It’s hard to imagine Greg as anything other than an engineer.

I found myself thinking about this while listening to Sean Morris talk, mostly because Sean Morris could be nothing but a CEO. He looks like he’s been successfully wearing a suit since middle school and has never once had a bad hair day.

But most importantly, Sean can explain the science behind Pulse Therapeutics, the medical device company he runs that’s developing blood clot dissolving technology, as easily as I can explain the science behind a grilled cheese.

Essentially, Pulse takes special iron beads and injects them into the bloodstream, where they attach to blood clots. A thick spinning magnet then quickly picks apart those clots, allowing blood to resume movement where it was previously blocked. The impact this technology could have on healthcare is enormous -- 800,000 Americans suffer a stroke every year and reducing the time it takes a clot to dissipate could save thousands of lives.

I’m not explaining this as well as Sean does, but I’ve also never felt comfortable in a suit. We all have our strengths.

Inside the Pulse Therapeutics lab.


If you ever find yourself at the Amtrak station in Lamy, New Mexico, please don’t ask for Cindy Lou. She won’t like that.

She didn’t even want to share her name. When I finally got her first and asked for her last, she looked at me like I was asking for fingerprints. Not entirely unexpected from someone who says her official title is, “Apolitical Atheist Angel.”

We just happened to get to Lamy the same day a snack and libations shop inside an old railroad car, run by Cindy Lou and a man named Butch, opened to the public. They're in charge of not only the snack shop, but also revitalizing what used to be a bustling train stop.

The Amtrak station in Lamy, New Mexico.

Lamy has lost a lot of industry in the last 50 years, including a historic restaurant and saloon. Giving people who are waiting for the train a place to eat and drink is the first step toward restoring some of that commerce.

Just don’t give Cindy Lou any credit. She’s the type of person who won’t brag about the country concerts near the train tracks she hosts in the summer that sometimes draw as many as 400 people, but will talk all about the cool things her friends are doing around Lamy. Local entrepreneurship, and more importantly, love for a town, doesn’t leave much room for self-promotion.


In 1927, Sears spent 180 days constructing what was then the largest building in Memphis. At 14 stories and 650,000 square feet, the mail-order processing warehouse and retail store was both one of the largest Sears in the country and a sign that Memphis's economy was on the rise. It was such a big deal that one of four Memphis residents toured the Sears Crosstown Building on its opening day.

But as retail brick and mortars started to shutter, so did Crosstown. The evacuation was slow but powerful. By the mid-90’s, the entire building was abandoned.

There it stood, the empty Art-Deco monstrosity reminding every Memphis resident for miles in every direction of a more prosperous time, until a combination of the city and private developers decided to step in. In August 2017, the newly-dubbed Crosstown Concourse re-opened as a mixed-use retail and apartment space after getting a whopping $200 million facelift. There are high-end coffee shops and nail salons and hip clothing stores and enormous, mesmerizing glass ceilings. It’s a lovely place to spend an afternoon.

The newly renovated Crosstown Concourse.

You don’t need to know any of this in order to understand Will Goodwin and Clark Ortkiese, but it might help clear up why Crosstown Brewing, the duo’s brewery, is so important to the community.

Opening in an auxiliary building right next to the high-rise, Crosstown Brewing is currently constructing one of the largest breweries in the city. The bar sits in front of a massive window overlooking the half-dozen brewing tanks in the back, and the brewery has received so much interest that the two expect their taproom to be full most nights. 

The huge brewing tanks inside Crosstown Brewing.

Like most craft brew founders, Goodwin and Ortkiese started with homebrew. They gave beer to friends, then friends of friends, and then bam, they had themselves a full-fledged beer company.

The difference is that craft beer isn’t huge in Memphis yet. There are a handful of local breweries, but the scene hasn’t blown up. It needs a spark, maybe even from an old building getting accustomed to revitalization. 


It felt like a prank, honestly. Santa Fe was the first city on our trip, on the itinerary partially to go visit Meow Wolf, an immersive art experience that raised $1 million on Wefunder in under 48 hours last year, the fastest raise in the history of equity crowdfunding. 

I expected it to be a topic of conversation in town, but I kid you not, every single local I talked to brought up Meow Wolf. Every single one. It felt like someone knew we were coming and planned the propaganda accordingly.

Here’s the thing, though: Meow Wolf doesn’t need any propaganda. It didn’t crush a fundraising round because it knew how to manipulate potential investors. It crushed because of the slide inside a fridge and the harp made of lasers and the driving simulator set in space. It crushed because it’s an incredible place, one that makes Santa Fe proud to be its home.

Just a sampling of the inside of Meow Wolf.

It’s easy for me to forget about Wefunder’s role in this. Meow Wolf is opening up a new Denver installation in 2020 that’s going to be three times bigger than Santa Fe and cost $50 million. It now employs more than 200 people. It’s becoming a huge company.

But after we hosted an event with Meow Wolf, employee and all around helpful human Layne Duesterhaus came up to me to say thanks. I assumed he meant about the event, so I said something about the pleasure of working together and began to turn away. But he grabbed me and said, “No. Thanks for helping us make all this possible.”

It’s one thing to sit in the office and conceptualize what raising more than $55 million for small businesses from 45,000 people means. It’s quite another to be inside one of these small businesses and see the smiles and the laughs inside that place -- to see the impact, to really and truly feel it.


Inside the Big Easy Bucha warehouse, huge metal tanks sit next to whirring bottling lines and cloth covered vats of brewing kombucha. Cases of the stuff are everywhere, even inside an old VW van behind the front desk that looks better than it drives.

This is Louisiana's first commercial kombucha company, and it’s doing well, as it's sold in hundreds of stores across the Southeast and just signed a deal to enter 1,200 Publix locations over the next year.  

Naturally, we all wanted to know about national expansion. We pestered Co-founder and CEO Austin Sherman with questions about getting into more West Coast stores, buying his own shipping trucks, and launching an online store. He humored us, but we eventually got the point -- pushing Big Easy Bucha to grow as quickly as possible could hurt the product. Creating a company named after an obvious reference to New Orleans means that cheapening the product would defeat the whole point of running the business. He’s focused on the Southeast, on Louisiana, on his home.   

From tank to bottle, the facility at Big Easy Bucha.

Two nights later, a handful of inebriated Wefunders walk into a converted garage and are greeted by a couple hundred locals shaking and vibrating and swaying together. On stage is Big Freedia, a local star who was one of the first artists to popularize New Orleans bounce music to mainstream America. Big Freedia is, well, big, and she’s loud, and she commanded a room like nothing I’ve ever seen before. She stood at the altar and we almost instantly joined the cult, rocking and dipping for the Queen of Bounce.

You get on the train to see your coworkers bask in a musician they didn’t know existed. You get on the train to break the Silicon Valley mindset of expansion without consequence.

You get on the train to remind yourself of what matters. 

Wefunder does Secret Santa, NOLA style.

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