Teacher’s guide: ‘Startup,’ the podcast

The "StartUp" podcast from Gimlet Media uses expert storytelling to sneak a wealth of entrepreneurial knowledge into students' minds.

The “StartUp” podcast from Gimlet Media uses expert storytelling to sneak a wealth of entrepreneurial knowledge into students’ minds. (Logo from Gimlet Media)

Two things I learned as a business journalist: One, business news can be deathly boring. Two, the best fix is to tell good stories. That’s why anyone teaching a class on entrepreneurialism would be smart to use the first season of “StartUp,” the podcast from Gimlet Media.

Gimlet is the brainchild of Alex Blumberg, a founder of the excellent storytelling financial podcast “Planet Money” from NPR. Blumberg left that show to start his own business producing crystalline podcasts. “Startup” was the first. In its first season, it chronicled a business getting off the ground. That business? Blumberg’s podcasting idea itself.

The shows were a perfect fit when I taught a class on the Business of Publishing, but the lessons would apply in more general approaches to startups as well. This is how I used selected episodes from the first season to introduce concepts and generate discussion.

Week 1, Episode 1

Blumberg records the abysmal failure of his first attempt to pitch an idea to a potential investor, Chris Sacca. The story quickly hooks students because Blumberg is open about his stumbles.

Prompts: Of all the things investors look for, which is the hardest to explain, and why? What could Blumberg have done before his meeting with Sacca to improve his pitch?

Exercise: Distribute or link to a few Kickstarter pitches. Ask each student to select a favorite and study it for a few minutes. Then challenge them to deliver a 30-second oral pitch for that idea, on the spot.

Exercise: Show one or more videos of successful elevator pitches. (Search “elevator pitch competition” online, looking especially for college students like this one.) Have students compare and contrast those with Blumberg’s.

Week 2, Episode 2

Blumberg tries out a revised pitch on Sacca’s partner, Matt Mazzeo. Mazzeo tells Blumberg he’s dreaming too small. Not only does the investor think Blumberg should expect huge audiences, he thinks the new company should be only incidentally about content. Instead, he proposes focusing on technology by reinventing the podcast listening experience.

Prompts: What factors will influence Blumberg’s decision about whether to change his focus to technology? What are the different risks of his choices?

Week 3, Episode 3

Blumberg realizes he needs help from someone with financial expertise. He finds Matt Lieber. It’s a great partnership … except it’s not a partnership yet. Eventually Blumberg is willing to give Lieber a stake in the idea, but that’s only the start of the angst. How big a piece of the pie can he “give away”?

Prompts: What would be the fairest split between the two, and why? How do you measure the value of the product, which draws customers, vs. the value of business wisdom that makes the enterprise profitable? How much is “It was my idea” worth?

Exercise: Divide the class into small teams. Assign roles such as inventor, sales expert, manufacturing manager. Have them negotiate the equity split.

Week 4, Episode 4

Blumberg and Lieber are challenged to provide more detailed numbers and show how their plan could quickly grow into an extremely valuable venture. Blumberg envisioned gradual development into a business that could pay his bills. The venture capitalists want much faster growth into a much bigger operation.

Discussion prompt: Building a business that you can run until retirement, vs. failing or succeeding big and fast and then moving on: Which sounds best to you, and why?


Week 5, Episode 6

(Episode 5, about naming the new company, is a fun listen.) Blumberg and Lieber figure out how to assign a dollar figure to the total value of their company. They do that so they can figure out how big a share investors will get for their money. Sacca explains the different levels of investment and focuses on what the company will fetch when it’s eventually sold, as he assumes it will be.

Discussion prompts: What pressures may Blumberg and Lieber eventually encounter because of who they’re getting money from? Is it fair for investors, who have no other role in the company, to have a say in its plans and operation?

Week 6, Episode 7

“StartUp” listeners get a chance to invest in the company. To explain how, Blumberg explores laws that have restricted crowdfunded investing.

Discussion prompts: Consider yourself a potential investor. What questions are you asking about this investment? At what point in your life would you be ready to consider investing?

Exercise: Direct students to a site such as Crowdfunder. Have them compare and contrast those pitches with the ones they saw earlier from Kickstarter.

Week 7, Episode 8

The company expands to a second podcast series by hiring two anchors. Blumberg has to persuade them to accept a salary cut from their previous job in return for a piece of the action. They buy in, but have to adjust to bare-bones facilities.

Discussion prompts: If you were P.J. Vogt and Alex Goldman, would you take the job? Why or why not? These two are getting a salary and a share in the profits, but some startups offer even less in return for the supposed benefits of experience, freedom and the entrepreneurial atmosphere. What’s fair?

Exercise: Have students find unpaid internship offers (online or through school resources). Ask them to list the advantages and disadvantages of specific jobs. They should take into account living expenses. (I’ve found students disturbingly willing to propose paying their potential employees nothing or next to it. This exercise may make the reality of what that involves clearer to them.)

Week 8, Episode 9

Gimlet Media’s gimmick for advertisers is that commercials are mini-stories: interviews conducted by podcasters. Crossing the streams creates a problem when, through miscommunication, a mom thinks her child’s going to be featured on “This American Life” (which Blumberg used to work for). Instead, the kid’s in a commercial. Gimlet’s staff discusses the fallout.

Discussion prompts: How well did Blumberg respond once he heard about the complaint? What do you think of the advertising strategy in general? In a crisis, what steps should a business take? What are the most important principles then?

Week 9, Episode 10

Blumberg and his wife, Nazanin Rafsanjani, confront personal difficulties with money and time. Meanwhile, the company’s early success creates questions about their original timetable and how Gimlet’s atmosphere is changing.

Discussion prompts: What say should your significant other have in your professional choices? What sacrifices are you willing to make to pursue your dream, whether it’s a business of your own or a dream job?

Week 10, Episode 12

(Episode 11 focuses on measuring and building audience.) Gimlet’s employees hit a wall. Long hours, exacting standards and frayed nerves lead to a blow-up, followed by an intense staff meeting.

Prompts: What were the most significant qualities of the person you think is the best boss (club president, whatever) you’ve had? What about the worst boss?

Week 11, Episode 14

(Episode 13 looks at the technology side. The description of a “design sprint” is interesting.) The first season wraps up.

Prompt: What are the biggest lessons you took away from “StartUp”?

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