Top Five Lessons Learned From The Startup Podcast

The idea of startups may evoke images of open office plans, endless healthy snacks, and ping pong tables, but the reality is that starting a business is hard – extremely hard. Alex Blumberg, the former Producer of This American Life and Planet Money created an uber-meta podcast about the gritty details of running a startup. His podcast, aptly titled The Startup Podcast, just wrapped up two seasons and is a highly addictive listen for anyone who has an interest in starting his or her own venture. In Season 1, Blumberg documents the journey of his own startup Gimlet Media. Season 2 follows the journey of two female entrepreneurs Lauren and Emma, of the online dating company Dating Ring. Readers beware of spoilers ahead.

1. Try to start a business that combines a field in which you are highly skilled in and a problem in which you are deeply aware of. In the case of Gimlet Media, Blumburg is an award winning radio producer who have worked for decades in the industry and has already amassed devote followers from his This American Life and Planet Monday days. The popularity of The Startup Podcast and the access that he had to raising capital are direct benefits from his previous experiences.

2. Co-Founder relationships can make or break your business. Finding a co-founder is in some ways harder than finding a life partner. As with any long term relationship, co-founders must share a common vision for the company. Additionally, a compatible work and communications style is important for co-founders to be able to continue to work together through difficult times. In Season 2, the relationship between Lauren and Emma first showed signs of strain when they were put under constant pressure at Y Combinator and later escalated when the company was on the verge of completely running out of money. What makes a co-founder relationship more complicated than a romantic one is the issue of equity, which came up as major plot points during both seasons.

3. Connections will only get you so far; investors will always drill down to the hard questions. Season 1 of The Startup Podcast opens with Alex Blumberg pitching to Silicon Valley Legend, Chris Sacca, who he had reconnected with from his Planet Money days. This is not an episode for people who suffer from second hand embarrassment.  After Blumberg delivers what might be the most cringe-worthy pitch ever recorded, Sacca immediately picks apart Blumberg’s idea by asking crucial questions about things that had been completely overlooked. In Season 2, Dating Ring was one of the lucky companies to have gone through Y Combinator. At first, Lauren and Emma rode the wave of investment from their Y Combinator Demo Day, but soon ran into difficulties raising more money as investors asked harder questions and were less affected by the Fear of Missing Out (FOMO). 

4. A startup can rise from being mostly dead. At Y Combinator, Lauren and Emma learn that when a company is in a really terrible position, they can run on Cockroach Mode. During this period, Lauren had to ask herself some really soul searching questions about the reasons behind running this business. The priority for Dating Ring transitioned from hyper growth to client satisfaction and the startup itself also morphed into a lifestyle business.

5. A startup may seem like it’s all consuming, but life still goes on. The best part about this podcast is hearing about the personal stories behind each business. People fell in love, people became parents. New colleagues were brought into the team and old colleagues left.  The beauty of startups is that running one is just as unpredictable as living life.  Whether, in the end, a startup is a triumph or a failure in a person’s life is not as important as having had the courage to give it a go, learn along the way, and maybe try, try, again.