David & Ben’s ‘Acquired’ Podcast Dissects What Went Right – New Episode Available

In 2023, Ben and David joined Managing Director Matt McIlwain to reflect back on the greater Seattle innovation ecosystem and the role of Amazon, the late Tom Alberg’s enduring impact and vision for flywheels, and the growth of the Acquired podcast founders from their days at Madrona. Listen here.


David Rosenthal of Madrona and Ben Gilbert of Pioneer Square Labs team up every two weeks or so to eat some food and talk about acquisitions. These can so easily go wrong. This podcast is about the ones that mainly went right – the “The 1+1=3 deals” as the authors say on their site. Why did these go right? What were the elements of success? And they are only 30 minutes! Perfect. The newest episode looks at YouTube (and includes a link to the original internal investment memo from funders, Sequoia)

Get the podcast from iTunes or from Acquired.

We sat down and asked a couple questions about the podcast and the response so far. Read on for fun insight and a good restaurant recommendation.

How did you get the idea for Acquired?
The idea was Ben’s— he had wanted to do a podcast for a while, and thought a theme around analyzing tech acquisitions would be a good mix of unique, focused and atomized-enough content that we could keep it going with fresh and interesting material. So far we’ve been very happy with how it’s working, and we have a few fun ideas in the works riffing on the theme— acquisitions that DIDN’T happen, “real-time” analysis when a big one gets announced, more special guests, etc.

What has the feedback been?
Our favorite feedback so far has been that David’s podcast voice makes people “want to wrap [themselves] in a silk kimono and roll around in rose pedals.” (direct quote 🙂 In all seriousness, the feedback has been great. We were surprised last week when we showed up on the Techstars blog rating Every Damn Imaginable Startup Podcast and fared pretty well! We were the highest rated podcast with 5 or fewer episodes at the time. In terms of constructive criticism, people have pointed out we agree too much (very Seattle of us), and that we take too long reviewing the facts before jumping into discussion/debate/analysis. We’re definitely working on getting better— please keep the feedback coming!

How will you know you are successful?
Maybe someday our podcast itself gets acquired (we hear Amazon is looking :). In truth though success for us really is about is learning and enjoying the process— and having an excuse to hang out every ~2 weeks. Every episode we do we’re learning a ton: about technology themes, what makes for successful longterm businesses, and how these few very special startups were able to generate a massive impact— not only financial but as products/platforms— often within a very short period of time. No question doing this show makes us better at our day jobs finding and building the next generation of great companies and founders.

If you had to call out one of the worst acquisitions ever (TIME/AOL off limits!) what would it be?
One of the themes we’ve seen again and again on Acquired is the power of leaving a great team and product alone to do its thing. Pixar, Instagram, Bungie— these companies all thrived when their acquirers gave them resources and not prescriptions. Some of the less-than-successful acquisitions have taken an opposite approach… it’s hard for instance not to feel disappointed looking at something like Yahoo’s acquisition of Flickr and thinking what could have been if Flickr had been allowed to blossom to its full potential. (but then we wouldn’t have Slack 🙂

What is the best meal you have had while taping?
Nijo’s, FTW.

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Related Insights

    Founded and Funded – Madrona’s Podcast about Startup Life
    How to Choose Your Early Customers with an Eye to the Future, with DocuSign Founder, Tom Gonser – Founded and Funded Episode 4
    How Do You Start a Venture Firm? Here’s Our Story