upside

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Summary

On upside, failure hasn’t really been the default. Most initiatives have come naturally and been met with, at worst, mildly positive reception. For the last few months, Jay and I have been struggling to find to an appropriate way to commemorate one year.

We planned a multi-week festival of podcasts. Too much.
We reached out to Steve Case. Nothing.
We interviewed each other. That felt wrong.

Today, we’re going to try something different. I’m going to speak to you host to listener, one to one, on my takeaways from one year of upside and what I see in the future.

Monique Villa changed my perspective of the podcast when she said that, to her, “founders are like books.” This podcast - therefore - is a growing, curated library.

Growing up, I was fascinated by libraries. Being surrounded by books is one of the two environments in which I feel a sense of complete belonging. The ability to disappear into a rack of books or simply peruse the aisles puts me in a state of awe. The output of thousands of human brains sitting on racks of dead trees waiting for your undivided attention. But when you choose a book and you read a book, that’s where the magic happens.

Mrs. Wilder, our grade school librarian, used to let me sneak into the library on bathroom breaks to read a few extra pages of the books I burrowed about the shelves, out of the sights of the Dewey decimal system and curious classmates. We had a book limit of 5 books per week, causing those with prominent shelving to incite a stampede during library time. When i could, I read those. When I couldn’t I read rest of the library - the undervalued titles that didn’t get the shelf space they deserved, the books with ugly covers, or boring titles on something like insect species.

Great books make you feel by teaching you something you already know in a way that’s different from what you know. When you read a great book, you aren’t being lectured, you’re having a dialogue. They say to never judge a book by its cover, and it’s my belief that you can’t truly judge a book until you’ve finished it. I’ve found parallels between traits of great books and traits of great founders.

First, they weave a thread through every chapter, through every answer. Sometimes unintelligible at first but always present. The history of the word “mantra” stems from Hindi and the act that ceremonializes and ratifies a ritual. To great founders, this ritual is their life’s work. They can’t answer a question about their business without hinting at the bigger vision. Nick Potts, the CEO of Scriptdrop, can hardly go 20 minutes without talking about his goal of helping one billion patients.

Second, they embrace their abnormality. Every great founder we’ve met is odd. They’re different. They don’t fit in. They don’t fit a mold. They turn down lucrative job offers to live on couches because of a beautiful excel template. They start sports media companies in Nebraska. They fly to China to buy factories because the contractors aren’t getting Spot’s eyes right. These people aren’t typical. They use that difference it in three steps: they identify it, they call it out, and they extort it.

Ashlee Ammon from Mixtroz literally made shirts to wear to a conference that said “Black Female Founder Fund Me” because she recognized she didn’t fit the model. Then she became the 37th black female founder to raise $1M in VC. Great founders don’t conform, they make their nonconformities shine and build a competitive advantage around it.

Third, they come highly recommended. Early on, Jay and I learned to use scarcity in our asks. We rarely ask for intros to more than 2-3 companies in an ecosystem and give very specific guidelines for what we are looking for. Usually, the same founder or two will emerge. In the Ross Baird / Village Capital model, founders know real founders. The local tech darling isn’t usually the best company.

Ezra Galston is a fantastic example of this. We asked for the best early stage venture capitalist in Chicago and three separate people recommended Ezra. In a world where your reputation matters, and matters a lot, those kind of people are who we aspire to talk to and who we aspire to be.

My favorite song by The Head and the Heart is called Library Magic. It’s a song about being inspired by those who live the lyrics they create. It’s a song about living your lyrics.

In this last year, Jay and I have created a library of over 60 episodes of founders, venture capitalists, and community builders who eat, sleep, and breathe their mission. It’s inspiring. It’s eye-opening, And, it’s humbling that they spend time away from their mission with us. We constantly feel the warm embrace of Library Magic whispering through the dusty aisles.

On a note looking towards the future, Nassim Nicholas Taleb says that the unread books in a library are more valuable than the read books. Those unread books present opportunity, potential growth, and new learning. I cannot wait to find new books and pull them into our ever growing upside library.

Thank you to everyone who has listened thus far, our fortitude would be immensely challenged without you. Thank you to our first sponsor, Taft, who took a gamble on us and a crazy non-traditional idea for sponsorship. Thank you to Nathan, without whom we would be still be podcast tadpoles. And, finally but most importantly, thank you to everyone who has been on the show - featured guests, insight guests, guest hosts - you have helped us in ways untold.

Looking forward to another year of Library Magic.

Follow upside on Twitter: https://twitter.com/upsidefm

Show Notes

On upside, failure hasn’t really been the default. Most initiatives have come naturally and been met with, at worst, mildly positive reception. For the last few months, Jay and I have been struggling to find to an appropriate way to commemorate one year. 

We planned a multi-week festival of podcasts. Too much. 
We reached out to Steve Case. Nothing. 
We interviewed each other. That felt wrong. 

Today, we’re going to try something different. I’m going to speak to you host to listener, one to one, on my takeaways from one year of upside and what I see in the future.

Monique Villa changed my perspective of the podcast when she said that, to her, “founders are like books.” This podcast - therefore - is a growing, curated library.

Growing up, I was fascinated by libraries. Being surrounded by books is one of the two environments in which I feel a sense of complete belonging. The ability to disappear into a rack of books or simply peruse the aisles puts me in a state of awe. The output of thousands of human brains sitting on racks of dead trees waiting for your undivided attention. But when you choose a book and you read a book, that’s where the magic happens. 

Mrs. Wilder, our grade school librarian, used to let me sneak into the library on bathroom breaks to read a few extra pages of the books I burrowed about the shelves, out of the sights of the Dewey decimal system and curious classmates. We had a book limit of 5 books per week, causing those with prominent shelving to incite a stampede during library time. When i could, I read those. When I couldn’t I read rest of the library - the undervalued titles that didn’t get the shelf space they deserved, the books with ugly covers, or boring titles on something like insect species.

Great books make you feel by teaching you something you already know in a way that’s different from what you know. When you read a great book, you aren’t being lectured, you’re having a dialogue. They say to never judge a book by its cover, and it’s my belief that you can’t truly judge a book until you’ve finished it.  I’ve found parallels between traits of great books and traits of great founders. 

First, they weave a thread through every chapter, through every answer. Sometimes unintelligible at first but always present. The history of the word “mantra” stems from Hindi and the act that ceremonializes and ratifies a ritual. To great founders, this ritual is their life’s work. They can’t answer a question about their business without hinting at the bigger vision. Nick Potts, the CEO of Scriptdrop, can hardly go 20 minutes without talking about his goal of helping one billion patients. 

Second, they embrace their abnormality. Every great founder we’ve met is odd. They’re different. They don’t fit in. They don’t fit a mold. They turn down lucrative job offers to live on couches because of a beautiful excel template. They start sports media companies in Nebraska. They fly to China to buy factories because the contractors aren’t getting Spot’s eyes right. These people aren’t typical. They use that difference it in three steps: they identify it, they call it out, and they extort it. 

Ashlee Ammon from Mixtroz literally made shirts to wear to a conference that said “Black Female Founder Fund Me” because she recognized she didn’t fit the model. Then she became the 37th black female founder to raise $1M in VC. Great founders don’t conform, they make their nonconformities shine and build a competitive advantage around it. 

Third, they come highly recommended. Early on, Jay and I learned to use scarcity in our asks. We rarely ask for intros to more than 2-3 companies in an ecosystem and give very specific guidelines for what we are looking for. Usually, the same founder or two will emerge. In the Ross Baird / Village Capital model, founders know real founders. The local tech darling isn’t usually the best company.

Ezra Galston is a fantastic example of this. We asked for the best early stage venture capitalist in Chicago and three separate people recommended Ezra. In a world where your reputation matters, and matters a lot, those kind of people are who we aspire to talk to and who we aspire to be. 

My favorite song by The Head and the Heart is called Library Magic. It’s a song about being inspired by those who live the lyrics they create. It’s a song about living your lyrics. 

In this last year, Jay and I have created a library of over 60 episodes of founders, venture capitalists, and community builders who eat, sleep, and breathe their mission. It’s inspiring. It’s eye-opening, And, it’s humbling that they spend time away from their mission with us. We constantly feel the warm embrace of Library Magic whispering through the dusty aisles.

On a note looking towards the future, Nassim Nicholas Taleb says that the unread books in a library are more valuable than the read books. Those unread books present opportunity, potential growth, and new learning. I cannot wait to find new books and pull them into our ever growing upside library. 

Thank you to everyone who has listened thus far, our fortitude would be immensely challenged without you. Thank you to our first sponsor, Taft, who took a gamble on us and a crazy non-traditional idea for sponsorship. Thank you to Nathan, without whom we would be still be podcast tadpoles. And, finally but most importantly, thank you to everyone who has been on the show - featured guests, insight guests, guest hosts - you have helped us in ways untold. 

Looking forward to another year of Library Magic.

Follow upside on Twitter: https://twitter.com/upsidefm

What is upside?

Named a top 27 business podcast by Fortune, upside examines startup investing outside of Silicon Valley.

Every Wednesday, we speak with an early stage founder. We interview them as if we are angel investors considering the company as an investment opportunity.

Each show has three segments:

1.) Intro: independent research of the company
2.) Interview: interview with the founder
3.) Debrief: breaking down the opportunity

On Mondays, we share Coffee Chats interviewing venture capitalists, community builders, and later-stage founders.