TBC: The Power of Helping When You Can (HBS Story)
In this episode, we explore how one small act of generosity can shape long-term relationships in venture capital. Jason shares a story from a recent trip back to Harvard Business School, where a simple coffee chat from a decade ago turned into a meaningful connection with a now-prominent VC. He reflects on what true network-building looks like—why helping others when it's easy can lead to unexpected returns years later.
In this episode, we explore how one small act of generosity can shape long-term relationships in venture capital. Jason shares a story from a recent trip back to Harvard Business School, where a simple coffee chat from a decade ago turned into a meaningful connection with a now-prominent VC. He reflects on what true network-building looks like—why helping others when it's easy can lead to unexpected returns years later.
Episode Transcript
[00:00:00]
Hey there. Welcome to another episode of the Back Channel. I wanted to record another episode sharing a story from my time at Harvard Business School. Again, I was able to go back to Harvard Business School, the graduate school, the business school that I graduated from back in 2012. And I. Uh, participate in a class that I actually took all those years back with the exact same professor that class was launching Tech Ventures, taught by Jeff Busking, also a general partner at Flybridge Capital.
And as I said my other episode, just an amazing experience, such a good time helping support, uh, that class, running office hours, individual coaching sessions, and being part of the lecture slash la one of the last classes of that semester. Now, this episode is much more about a side experience that I had while visiting Harvard Business School, and it is related to the idea of [00:01:00] network and network building, which obviously is a big part of fundraising.
So very relevant for the back channel, and it's not gonna go maybe in the same direction that you thought it would. Maybe you thought I would talk about network and networking. Being at Harvard Business School and all the people that went on to do amazing things. Not in this episode, I want to talk about.
Somebody that I met after HBS, who actually was somebody who was graduating from business school a year after me. Now, there's something funny about business school. Business school is not aligned age-wise in the same way that undergrad is. You'll often have people that are older than you go to school before you, and so it's just a weird dynamic.
But either way, what I found is that people that graduate earlier are. Um, I respected as elders, almost like you went a year before me, but I, I actually don't know how old these people are anyways. There was a student that was graduating [00:02:00] in 2013 who reached out to me, uh, and asked me for a coffee chat while I was an investor at Greycroft.
He wanted to break into venture capital and just hear my thoughts on it, see if I could help him in any way. Now, that's how I met this guy, and when I was coming back to Boston and looked through my network just to see if there's anyone that I wanted to catch up with, I caught his name and just sent him a note, just saying, you know, Hey man, I'm gonna be at HBS.
I'll be teaching LTV. I'll be spending time on campus if it's convenient to you, I'd love to see. You'd love to hear what? What's been up. And this guy really went out of his way to spend time with me, find a gap in our schedules that would work, actually come to me and just chop it up and, and shoot the shit and hear how our last 10 years have gone.
Uh, nothing more than enough. Nothing more than that. No ulterior just catching up with something that I thought might be interesting, and in fact, it was extremely interesting. This guy had [00:03:00] broken into venture capital and did what he needed to do to rise to the ranks of partner and actually become a GP at a up and coming very cool venture capital firm RI raising something like fund three or fund four, successful in its own right.
And he obviously had tons of his of his own success. And as we finished up our conversation. He goes, Hey man, I, you know, again, I, I just want to say thank you so much for what you did for me all those years back. I really appreciate it. So if there's anything I can do ever to help you and, and I'm just so glad I was able to find time to come over and, and see you before you left.
But yeah, if there's any way that I can help you, I, uh, I, I really want to do that. I will never forget the way you treated me. Which was such a nice thing to say to me because to be honest, I don't even remember the conversation. I don't, I, I don't remember what I did or [00:04:00] if I pulled huge strings or not, but this guy was really nice about the time I'd spent with him.
[00:05:00] And this is the takeaway for network building for the impact of network. This guy is a major GP at a firm that people deeply respect. And my business is in, is in venture capital. It is in startups. It's, it is good to know this guy. And it all came from a random outreach where [00:06:00] somebody asked for a little bit of my time, and I imagine based on how I had formed my thoughts around network building and helping people, that all I did was.
Try to be as helpful as I could where it was easy. I'm not gonna try to paint myself as a saint in helping everyone, but the advice I always give is if you can help, especially if it's easy, help. Help all the way. Help as much as you can. I'll tell you, I really learned this from the partner that I worked for at Greycroft.
One of the founding partners at Greycroft is a woman named Dana Settle. And I often tell this story where early on in my career. Actually, it must have been week one or week two on the job. Post HBS at Greycroft. I'm working with Dana Settle and we take a pitch for a founder who is working in sports technology and I had been the head of new media products@mlb.com, major League Baseball's digital media company.[00:07:00]
And as this founder was pitching, I was like, oh my God, all these like synapses were firing and all the connections in my mind were going off. I was like. Man, I know how to help this company. So afterwards, I told Dana, I was like, Hey, um, there's a lot that I could do to help this company. I know everybody in sports tech.
I know everyone@mlb.com. I could make a few phone calls, send a few emails, and really kind of pave the way for him to be successful in this space. What do you want me to do? Do you want me to like wait until we do a little bit more diligence, whether or not we actually wanna do the deal, use it as a bargaining ship.
And to her credit, she was like, no, that's not the way we do things. You should help. You should help as much as you can help. And if it comes back to us, it comes back to us. But her strategy and the thing she taught me was essentially like, it's too much effort to play all these games and hold back things.
It's much. [00:08:00] Better, much easier to just give, give, give help, help, help wherever you can and assume that it'll come back to you. I know other people play the game in a different way. That's not like my style and that's not easy for my brain to manage. And so if you are anything like me, take this story of the, of the venture capitalist that I met or met back up with a couple weeks ago and how grateful he was, uh, for the small thing that I probably did 10 years ago.
That now leads to a great relationship where if there is a way for him to help me, I do believe he will. So go forward, build your network, help when you can, especially when it's easy. And catch me on the next episode of the back channel. All right, thanks so much guys.

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