Becoming A Full-Time Coach with Steve Schlafman

Steve Schlafman (0:02)

Then he said something that I'll never forget in my life. And he said, you know, for a long time, I didn't think I was ambitious, until I realized that my ambition is to have a good life.

And in that moment, it just clicked.

David Nebinski (0:19)

Hey friend, it's David Nebinski here in Brooklyn. Here at the Portfolio Career Podcast, we help you take ownership of your portfolio career and design the life that you want to live. Today's conversation is with Steve Schlafman. You may remember Steve from an episode that we did in the fall of 2018, episode 22

Steve is a legend in the New York tech ecosystem and is someone I look up to immensely. This was a really special episode for me, and I hope you really enjoy it as well. This episode happened in front of a live audience in an apartment in Brooklyn with about 20 people there total. You'll hear people asking questions during the episode when I will hand them the mic and they will ask a question. Steve is a writer, podcaster, a coach, a dad, and he used to be an investor. In this episode, you'll learn about Steve leaving a 10 plus year career as an investor to go full time coaching in addition to writing and being a dad. His specific recent transitions and how you might want to think about transitions, holistic ambition and tips for growing a coaching business. So if you're going through a transition, you're interested in coaching and starting a coaching business, this episode is definitely for you.

As always, this episode with time-sip notes is available on my website at portfoliocareerpodcast.com. There you can subscribe to my new newsletter on Substack called Portfolio Career, and you can also take my free podcasting course. So excited for you to build and grow your portfolio career. Here we go, Steve.

So, fall 2021, Madison Square Park, conversation, Jonathan Basker. Tell us about that conversation.

Steve Schlafman (2:09)

Yeah, just for a little bit of context, I had spent the previous almost two years really living a dual existence. I spent about three quarters of my time coaching and growing and building my practice. And I spent 25% of my time investing as an angel investor. As I, when I left venture investing, I raised a small fund from family and friends. It was kind of a side hustle. A lot of people are doing it at the time.

And I had basically north of seven and a half million in commitments for a new fund. And I was actually gonna merge coaching and investing together. And I was talking with Basker, and he said, you know, he goes, I don't know if this is the right, and I was like torn. I'm like, am I investor? Am I a coach? Like, I've definitely leaned into the coaching thing, but this investor part of me, this identity doesn't want to die. And he's like, every time I talk to you, you don't sound like you want to be an investor. It's like you're the girlfriend in a bad relationship, and you keep on going back to investing.

And then he said something that I'll never forget in my life. And he said, you know, for a long time, I didn't think I was ambitious until I realized that my ambition is to have a good life.

And in that moment, it just clicked. And that was like, oh, I get it. And that in some ways was like the permission for that investor part to finally just melt away, because I was like, yeah, my ambition isn't to be the world's best venture capitalist. It's like, that's like so foreign.

And so basically a few days later, I sent an email to my investors and said, rather than asking them for money for the first capital call, I said, I'm not gonna move forward with the fund. And that was, I mean, almost a year and a half ago. And I feel like I'm now coming kind of on the, I'm sort of on the other end of this long transition that really has been like six or seven years in the making, which is crazy to think.

David Nebinski (4:40)

So when you think about that six or seven years, are you suggesting there that transitions take time, or do you think that's more related to your own journey?

Steve Schlafman (4:52)

I think both.

I think transitions when, I hate using this word done properly, but when transitions are gonna take the amount of time that they take, and especially if we don't try to rush them. And for me, in a lot of ways, with the benefit of hindsight, it was a large transition, but a series of kind of small transitions interspersed.