What Can “StartUp” Podcast Really Teach Us About Starting a Business?

If a picture is worth a thousand words — an experience, shared, is priceless.

Udi
Udi
May 25, 2020 · 8 min read

It is wonderfully miraculous, to me, that for near zero costs we have the opportunity to listen in on conversations between the greatest minds of our generation. Imagine listening to the Wright Brothers, spitballing about flight. Or the Dodge Brothers; debating automotive’s. Today’s innovators, scientists, entrepreneurs & creatives are infinitely more accessible — an audible universe of ideas & experience awaits anyone with the gumption to tap into it.

How? The mighty podcast.

Given this mystically enchanting reality we now live in. I’ve taken it upon myself to review my favourite material gleaned from hours of listening. Selfishly, my aim personally is to mitigate the sheer volume that seems to go in one ear and out the other. Magnanimously, my aim for you — dear reader — is to serve as the divine spark of inspiration that drives you to download one and experience the magic for yourself.

Podcast: a kid shares his startup story through a microphone
Podcast: a kid shares his startup story through a microphone
Photo by Jason Rosewell on Unsplash

Fond of the Pod

So what can the StartUp podcast teach us about starting a business?

Well fortuitously the premise is to document, with a shocking amount of radical transparency, the genesis of Gimlet Media — a podcasting network behemoth which was sold to Spotify for $200 million.

I first heard about co-founder Alex Blumberg before he dreamt up the business, in his years as co-host of a public radio podcast called “Planet Money”. They were (and still are) masterful at taking complex economic issues, and turning them into bitesize globules of infotainment.

Point of Interest: his co-host Adam Davidson had major involvement in the creation of the award winning movie “The Big Short”, primarily in a consultative role to director Adam Mckay.

As Planet Money grew, and tested the boundaries of the nascent podcasting format, they experienced success which would inspire Alex with the notion that he might bring his own company to fruition. As an example, Planet Money are inspired by a book, called “The Travels of a T-Shirt in the Global Economy”, to track the entire supply chain of a simple cotton T-Shirt.

You can actually see the whole process here i.e.
Cotton Growth → Purchase → Transport → Spinning into yarn/thread, etc.

Image for post
Image for post
Photo by Matthew Lancaster on Unsplash

The audience is so enthralled by the series that over 25,000 T-Shirts are sold at series end. This potential, of the podcasting medium, is so overwhelming that Alex goes on to start Gimlet. Then, in a clairvoyant moment of foresight, he elects to record every moment from that juncture onwards. This is the source material for the first in his media empire: StartUp Podcast.

Lessons

Key takeaways are plentiful in each episode of the longstanding series. I’ve taken the liberty of sharing glimpses of the tastiest stories this absolute podcasting banquet has to offer. These are split into three sections:

  • Fantastic Feasts are where the StartUp team do a multi-episode dissection from every viewpoint possible, widely sourced, intricately examined.
  • Tasty Morsels are typically two episodes of exposition that delve right into the heart of the action with raw clarity and profound emotional weight.
  • Lite Bites are single episode snacks that take individual facets of entrepreneurial characters, scenarios, or situations & unpack them.

Fantastic Feasts

The Dove Charney Series — a story of the rise and fall of an infamous clothing brand, American Apparel. Reporter Lisa Chow spends almost a year with its founder, Dove, and unravels a deeply complex and surprising cautionary tale, told from his perspective. Dove is a classic anti-villain who, on the one hand, displays a number of admirable entrepreneurial qualities that drive his business to a peak of 250 global stores, valued at nearly $1 billion. But, on the other hand, struggles so viscerally with ethics, self control, values and behaviour that ultimately these prove his (and his company’s) undoing. Talk about Sex, Drugs and Rock n Roll — This one is a doozy.

Key Takeaway: The Culture of an organisation is inevitably, inexorably, shaped by its leadership. The more intentional an organisation is (about this) at the outset, the easier this will be to manage on an ongoing basis. Moreover, sometimes a business outgrows its founder and/or requires a modicum of management experience once it grows to a certain level. Alex Blumberg talks about this in early episodes where we learn how Gimlet Media’s culture was shaped initially with these lessons in mind. Great episode.

Leaders shape culture. A team follows behind and picks up lessons taught both overtly and inadvertently.
Leaders shape culture. A team follows behind and picks up lessons taught both overtly and inadvertently.
Photo by Jehyun Sung on Unsplash

The Eva Muscowitz Series — a story of the rise and rise of Success Academy, a network of charter schools that originated in Harlem New York. This a tour de force of gripping storytelling I literally couldn’t get enough of. Faced with a public schooling system that, to many, fails to deliver on the lowest of expectations — Eva Muskowitz vacate’s her role in a government, she no longer has faith in, to do something about it. This is a classic entrepreneurs tale: see a problem, solve the problem. From nothing, she raises a minimum level of capital and bootstraps an entire schooling ecosystem. The vision, mission and execution are a marvel to witness as she convinces parents to enrol their children even before the first school structure is built. She goes on to build something really rather remarkable that changes the lives of hundreds of thousands of families, facing heavy criticism from all angles but delivering astounding results. A stunning story.

Key Takeaway: A vision is essentially the idea, hope and aspiration for what it is possible to achieve/build/create. A mission is why you go to the trouble of executing that vision, specially when it gets hard. At the confluence of the two, when they are meaninful to an entrepreneur & team, amazing things happen.

Three other superstar series I’d recommend. First that of Arlan Hamilton (Backstage Capital). She is an utter phenom who goes from being homeless to investing over $5 million into startups founded by minority groups. Emma Tessler & Lauren Kay (Dating Ring) whose journey is well captured. Also that of Alex Blumberg & Matthew Lieber (Gimlet Media) who give us access to all aspects of the business building process: from idea → exit (and beyond).

Tasty Morsels

These delights are plentiful and exquisitely exorbitant. I was particularly moved by the Coss Marte (Conbody) redemption story. A young man grows up, in tough surroundings, with a narrow range of productive life paths and positive role models available to him. Institutionally, socially & economically his choices are mitigated, given a lack of opportunity. This young man procures a product in high demand from society, and is able to sell it at supernormal profits. His clients include bankers, lawyers and holidaying tourists. Given this insatiable demand, young Coss builds a multimillion dollar business with his childhood friend. So far this story is the American Dream writ large!

Only problem —the product is drugs, and not the pharmaceutical kind.

It’s at this stage, I feel, that Coss goes from being avidly entrepreneurial, to being uniquely remarkable. The statistics on recidivism (the tendency of a convicted criminal to reoffend) globally are not pretty, Once you are incarcerated, the likelihood is that you are now locked into a cycle of release & re-offend. Having been caught & imprisoned, Coss breaks the pattern, does his time, starts a fantastic business, earns investment & is changing the world.

Key Takeaway: Honestly, before listening to this episode I would have balked at the idea of working with, or ever hiring, a former inmate. Yet for those rehabilitated enough to re-enter society, it is incumbent upon our communities to avail every opportunity possible for such individuals to prosper and contribute to that society. It makes the world better for all of us.

A Bird in Prison, caged. Metaphor: people do find redemption, peace and inner beauty. Society is well served trusting that.
A Bird in Prison, caged. Metaphor: people do find redemption, peace and inner beauty. Society is well served trusting that.
Photo by Jehyun Sung on Unsplash

There are three other absolute blockbusters: Jonathan Abrams (Friendster), Justin Kan / Emmett Shear (Twitch) and Rick Schwartz (the Dotcom King) who starts off buying 1–800 numbers (e.g. 1–800-MAKEOUT) before people realise how easy they are to memorize. He then makes a killing selling them to businesses when they catch on! He does the same thing with websites e.g. buying www.porno.com for $42,000 and earning $30,000 a week for five years before selling it for $9 million (about $30 million profit total!). Insane.

Lite Bites

Finally you have these little snackables that finish all too quickly for my liking. One episode stunners, the most striking of which is the tale of Edgar Diaz (Three Happy Cows). His family is forced to escape a great middle class life in Colombia due to Cartels sucking the life blood out of his yoghurt business for “protection”. They obtain asylum in America and start a yoghurt business there which eventually gets sold for millions. Amazing, except, the only issue is he does not see a dime of that. Oh, and he goes to prison! My heart weeps.

Key Takeaway: I don’t want to ruin the premise/story here but the main lesson I draw from this one is to be really clear about ownership at the beginning. Alex & Matt (Gimlet) do a fantastic episode on how they approached this. The Dating Ring ladies have this question really terrorise them for a while and there are a plethora of examples where it proves the undoing of otherwise great businesses. Seth Godin offers great advice on equity with the proviso that at any stage one partner is able to buy the others out; upon making their offer the other partners have the choice to take it OR buy the initiating partner out at that price.

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Image for post
Photo by Alejo 99 on Unsplash

Another great episode is prompted by the boss Alex Blumberg who is from Cincinnati and notes a singular retail outlet in town that almost seems to be cursed: 2680 Madison Road. Year after Year, whilst other businesses have boomed around it for decades, it seems to cycle through entrepreneurs that try to take it on and fail or move on for some reason. The StartUp team goes to work investigating the stories behind each business that has taken up residence there. We learn alot about the love, passion & imagination that goes into a growing a business at any location. The episode reminds us of the transient nature of life, and the inevitability of our impermanence.

Do let me know if this encouraged you to listen to one. Do share your thoughts in the comments below and/or connect with me on Linkedin here.

ILLUMINATION

We curate outstanding articles from diverse domains and…

Udi

Written by

Udi

Lead Lagomorph at www.sportwarren.co.uk (launching 2020). Songsmith at www.soundcloud.com/papajams. Director of Studies at www.minervatutors.co.uk.

ILLUMINATION

We curate and disseminate outstanding articles from diverse domains and disciplines to create fusion and synergy.

Udi

Written by

Udi

Lead Lagomorph at www.sportwarren.co.uk (launching 2020). Songsmith at www.soundcloud.com/papajams. Director of Studies at www.minervatutors.co.uk.

ILLUMINATION

We curate and disseminate outstanding articles from diverse domains and disciplines to create fusion and synergy.

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