Don't Follow My Lead

PLUS: Chris and I fought over the special guest at our next event

January 28 event update (including the speical guest Chris and I fought over):

I’ve shared this with many of you reading, but our next NYC-based event will be held on January 28th.

This event promises to be DIFFERENT than all previous events because we have invited a special guest. Namely, we have hired a professional magician 🪄 to come walk around the room doing card tricks as people mingle. Apparently he is fantastic (according to my friend who hired him for a recent party), so it should be a phenomenal time.

If you’d like to come to the event reply to this email or text me or DM me on LinkedIn and we’ll get you the link (we have 8 spots left as of writing).

A shot from our October 2025 event

Why jumping around early in a career might be a good thing: 

I recently learned about the Dark Horse Project, a research initiative out of the Harvard Graduate School of Education. The focus of the project was to understand how people find fulfilling work while also developing superior expertise in their given field. As part of the study, researchers interviewed 50 people considered to be at the top of their respective professions. Notably, of the 50 people interviewed, 45 expressed a sentiment of “don’t tell people to follow me. I jumped around a lot. I didn’t follow the traditional path to get here.” However, as journalist David Epstein said during his interview on the Diary of a CEO podcast, it turns out that this “hopping around” model may actually be the perfect path to follow for someone looking find fulfillment in their work while also being a top performer. As Epstein put it during his discussion of the Dark Horse Project,

People who found fulfillment would travel this kind of zigzagging path where they would learn maybe I’m good at something or bad at something that I didn’t expect. Maybe I’m interested in something I didn’t expect. And they would keep pivoting and they’d say here are my skills and interests. Here are the opportunities in front of me. I’m going to try this one. And maybe I’ll change a year from now because I will have learned something about myself. And they keep doing these pivots until they achieve what economists call better match quality between someone’s interests and abilities.”

David Epstein, Diary of a CEO Podcast

As someone who quit three jobs in the span of four years, this idea really resonated with me. While working at a bank, being an SDR, and running a sales team are all vastly different roles, there is no shot that TopSDRs would exist today had I not spent time in all three. Every experience was an opportunity to collect more datapoints on myself. To learn what I liked, and disliked, what I was naturally good at/bad at. It’s very similar to sports. I rowed for 4 years at Harvard, most of those years in the top boat, but I didn’t start rowing until spring of my Junior year of high school. I spent a lot of my childhood messing around in different sports, doubling down on swimming for a while, and then ultimately deciding to make a pivot to rowing. Had I stuck with the first sport I played or the first job I had, my guess is I’d be a pretty average bank employee with no real athletic achievements to speak of.

In the podcast, Epstein ties all of these ideas together with a concept that he labels exploration and exploitation. Essentially, people who are really successful are constantly moving through cycles of trying new things, asking questions, accumulating, knowledge (exploration), and then applying everything they learn (exploitation). As Epstein says, “people tend to have hot streaks in their careers. And reliably, what precedes a hot streak is a period of exploration where they are trying different things.”

So does this mean you should quit your job tomorrow if you don’t feel totally and completely fulfilled? Definitely not. First off, nobody feels totally fulfilled every day no matter who you are or what you’re doing. Second, I think a big takeaway from the project is that there is a lot of value in sitting in something that doesn’t fulfill you as long as you are intentional about it. Spend time marinating in the dissatisfaction. Write down what’s bothering you. Write down what you want more or less of in the next role. Of course don’t let yourself get complacent, but also don’t be rash. Explore then exploit.

A quick congratulations

Finally, since we last sent one of these out we have placed dozens of candidates across the founding teams at businesses like Avoca, Profound, Warp, Outtake, Basic Capital, Clarion Health and many others. Congrats to all of you!

As always, we have plenty of SDR roles open across the best startups in NYC. Reach out if you or someone you know is interested.

-Andrew