Good Ideas Won’t Get You There: How Dave Gerhardt Went From Podcast Side Hustler to VP of Marketing at Drift


The Bench Team


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March 7, 2019

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The following is Dave Gerhardt’s story as told to Jared Lindzon, exclusively for Bench.

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Good ideas are a dime a dozen: the real value comes through execution.

In 2014 I was just starting to navigate my way through the Boston tech scene thanks to my new job at a local start-up called Privy. As my interest in the industry grew I listened to podcasts like This Week in Startups, which I really enjoyed, but there was one thing that kind of bugged me: everything was so focused on San Francisco.

There was a lot going on in the Boston technology scene at the time, but nobody seemed to be talking about it. As my appreciation and understanding of both the local startup and podcast landscape grew, I wanted to further both interests by launching my own project. I had this strong itch to go out and do something, there was just one problem; I didn’t know the first thing about making a podcast.

I didn’t let that stop me though. This was the first time I had tried to make something from nothing, and I found a lot of motivation in the idea of creating value for people I had no prior relationship with. The idea of opening up a dialogue with them and creating this sort of feedback loop and building a community around it inspired me to keep going.

After doing some research I found a few online articles and some very helpful Reddit users who gave me the information I needed to get started. So, I bought a microphone and just kind of winged it.

I produced the first five or six episodes of my new podcast, Tech in Boston, between April and July of 2014. I felt they were okay considering my lack of experience, but after a few episodes I got bored and decided to stop. I just wasn’t seeing the traction I had pictured when I first started out, and those single and low double-digit download numbers weren’t really motivating me to continue.

Then something unexpected happened: after about two or three weeks of inactivity I started to get emails from strangers asking me why I stopped. It was the first indication that anyone other than my mom and my wife were listening. I wasn’t going viral, but it gave me just enough juice to give it another try.

I returned to the podcast that September after a two-month hiatus with weekly episodes every Friday, and for the first time it felt like I was building some momentum. It was still a pretty amateur operation, but because I was the only one putting together content about the start-up scene in Boston I had a really dedicated audience, which made me want to keep going.

It eventually got to a point where I couldn’t afford to keep putting my own money into it. After all, I was still just a broke 25-year-old kid and I needed someone to underwrite the cost of gear and equipment, music licensing, web hosting and other expenses that come with launching a podcast. I really wanted to keep growing and building this thing but in order to do that I needed to start earning revenue from it.

I knew the first few sponsors I’d approach were going to say “no,” and I was almost too afraid to even ask, but once I started getting rejections I can honestly say that I loved them. Each rejection came with a better understanding of what I needed to do to make the offer sound more appealing. They would tell me things like “if you doubled your audience size we would be interested,” and all of a sudden I went from having no idea what it takes to get sponsorship to having real benchmarks.

When I started making podcasts I had absolutely no idea what I was doing, and that’s okay; the only way to learn is to just start doing.

I knew I only needed two or three positive responses to make the whole thing work, so I kept having those conversations, knowing that each “no” brought me closer to a “yes.”

Not only did the sponsors I signed on help me cover my expenses, but I was even able to collect a small side income. The sponsorships helped improve the quality of the podcast, which in turn helped me attract more guests and increase my reach. And since they were also part of the same community the sponsors were able to help me get more distribution as well.

All of these efforts caught the attention of Mike Volpe, the CMO of HubSpot at the time, who hired me to launch the company’s small business podcast. The project I developed for HubSpot in 2015 got over a half million downloads in its first year, and even reached the number one business podcast spot on iTunes for a brief period of time.

Meanwhile I continued to produce weekly instalments of Tech in Boston until about two years ago, when personal and professional commitments got in the way and my priorities shifted. In the end I made about 60 or 70 episodes which have been downloaded approximately 100,000 times in total, and built a loyal following of about 5,000 subscribers.

Today I’m the vice president of marketing at Drift, a conversational marketing platform based in Boston, a job I received after interviewing my current boss David Cancel for Tech in Boston in 2015.

To this day I still get emails from people telling me that they’re digging into the archives and getting value out of the podcast. It’s still a great primer for learning about the local tech scene in Boston, especially because the content is still so relevant.

When I started making podcasts I had absolutely no idea what I was doing, and that’s okay; the only way to learn is to just start doing. If I hadn’t, I wouldn’t be where I am today. The podcast was a good idea, but good ideas are a dime a dozen. Seeing them through is a grind; it takes effort, it takes consistency and it takes commitment. Having an idea won’t really do anything for you; seeing it through could change your life.

Illustration by John Larigakis.

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This post is to be used for informational purposes only and does not constitute legal, business, or tax advice. Each person should consult his or her own attorney, business advisor, or tax advisor with respect to matters referenced in this post. Bench assumes no liability for actions taken in reliance upon the information contained herein.
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