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I wasn’t a lemonade stand kind of kid.

Instead, when I was 8 or 9 years old I told my mom that when I grew up, I was going to own an entire fleet of ice cream trucks. Back then ice cream was the most valuable currency I dealt in. So, naturally, my dream job involved having unlimited access to it.

I would sit in an office above an ice cream distribution center—where the ice cream men went to fill up their trucks on in the summer—and do whatever one does in an office when one owns an entire fleet of ice cream trucks. (This was before the internet and even before computers were ubiquitous, so I imagined some sort of hopper for my papers and maybe even a paperweight.) And the best part, I told my mom, was that she could come visit me at work whenever she wanted and I’d give her free ice cream.

More than two decades later, shockingly, I do not own a fleet of ice cream trucks. I do not have an office above an ice cream distribution center. Hell, I barely even eat ice cream anymore. As best laid plans of third graders often go, this one sort of fell apart after I got really into Teenage Mutant Ninja Turtles.

For Alex Blumberg, the host, producer and subject of the new podcast StartUp, there’s a little more at stake than free ice cream.

Blumberg is best known for his work with public radio, including the program This American Life (producer) and podcast Planet Money (founder, co-host). But he recently quit both those gigs to start his own project: he’s starting his own media company which will focus on producing and distributing high-quality audio content via podcasts. Oh, and the best part–for us, anyway–is that he’s letting listeners in on the process. Here’s how Blumberg describes it on his website:

This show follows what happens next – my difficult journey from man to businessman. It’s a classic start-up story, but one that’s recorded in real time. I’ve documented disastrous pitches to investors, difficult conversations with my wife, and tense negotiations with my co-founder. The result is an honest, transparent account of something that happens all the time, but that we can rarely listen in on: starting a business.

StartUp is not a prescriptive how-to guide to starting a business from the ground up (this, despite several episode titles beginning with “How To”). It’s quite the opposite. It’s a show about a guy who knows very little about starting a business, and what happens along the way as he starts to figure it out.

The weekly series, which premiered on September 5, is just seven episodes in. So far Blumberg has taken us through a failed investor pitch, the process of taking on a business partner (after realizing he couldn’t do it alone), figuring out how to share equity with that business partner (a very cool insider’s look at emotional side of the process), assigning a value to a company that doesn’t make any money yet, and even picking a name for the company.

As I’ve written about previously on this blog, I’m big fan of ABC’s Shark Tank. On that hit reality show, entrepreneurs come to the sharks (i.e. potential investors) with a fully (or partially) formed companies asking for investments in exchange for shares of their businesses. Some entrepreneurs get deals, others are sent packing. On the show it all seems so simple.

StartUp is, in many ways, a prequel to Shark Tank.* As of episode #7 Blumberg’s company, Gimlet Media (for the origin of that name, check out episode #5), is still “pre-revenue.” On Shark Tank most pre-revenue business don’t get a deal unless the idea is very, very novel.

 *If StartUp is the prequel to Shark Tank, then shows like Hotel Impossible, Restaurant Impossible, and The Profit–all of which deal with businesses gone bad–are the sequels.

For those of us who have dreamed about owning their own business—for the record the ice cream thing is still on the table, though I haven’t figured out what I’d do all winter yet—and those who haven’t, StartUp gives listeners a fresh look into those steps between concept and actually taking those steps towards turning that concept into a living, breathing, (and hopefully) profitable thing.

The most interesting stuff for the listener tends to be that which is most gut-wrenching to Blumberg–from figuring out how much equity to give his partner (episode #3), to the constant self-doubt that comes with starting a business in your forties when you have a wife and two young children to consider every time you make a decision about anything.

In episode #2 Blumberg debriefs with his wife on the phone after an investor, Matt Mazzeo, in Los Angeles. Blumberg has been out to L.A. before, in episode #1, to meet with Mazzeo’s business partner, Chris Sacca. Mazzeo and Sacca are venture investors and business partners at Lowercase Capital. They have successfully invested in the technology space. After talking with Mazzeo, Blumberg is left with a pit in his stomach:

I’m feeling the same shitty way I’m feeling the last way I was out here. … It just makes me feel like I don’t know what I’m doing. … This is the thing: I’m sitting there talking to this guy and I’m describing something that feels like the biggest thing I’ve ever done, a scale beyond my wildest imaginings, something that I can’t even tell if I can pull off, and it’s totally not big enough. Like it seems small to him.

This is a really important insight, and one that I suspect a lot of startup business owners face when pitching investors. Especially in the tech space.

Can you or I invest in companies like Gimlet Media?
Episode #7 was about crowdfunding Gimlet Media. According to the episode, the 2012 Jumpstart Our Business Startups (JOBS) Act allowed for Americans to invest in private companies like Gimlet Media, which they were formerly not allowed to do. This means that through companies like Alphaworks, would-be investors could go online, find a company they wanted to give money to, and in exchange they’d receive equity in that company. (This is different than sites like Kickstarter, where you “donate” money but don’t receive any equity.) A Shark Tank for the Average Joe, right? Wrong.

Due to current Securities and Exchange Commission regulations, only “accredited investors,” i.e. those who make $200,000 a year and/or have a network worth of $1 million, may do so. (Alphaworks covers this in their FAQ.) If you’re an Above Average Joe, invest to your heart’s content. Otherwise you’re out of luck until the SEC loosens those regulations. Fortunately for Gimlet Media, they had enough friends in high places–in part thanks to attention the StartUp podcast has been getting–to get to their investment goal.

New episodes of StartUp are available about every two weeks. Whether you’re a future ice cream magnate or not, I recommend you give it a listen.

You find the StartUp podcast here: http://hearstartup.com/ – or you can use a podcasting app on your phone or tablet and search for StartUp. Happy listening.

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