John Gannon of GoingVC // helping people break into venture capital [CC077]

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Jay Clouse 0:01
You know, Eric, on the show time and time again, founders talk about the importance of hiring great employees.

Eric Hornung 0:07
And they always say it’s so hard and so important early on to hire the right person.

Jay Clouse 0:12
That makes a lot of sense as difficult because most founders don’t have experience doing high level searches or hiring top level talent.

Eric Hornung 0:20
And they’re also limited to their local talent pool a lot of the times.

Jay Clouse 0:23
That’s why a lot of founders choose to work with SPMB be one of the fastest growing executive search firms in the country. For over 40 years. SPMB has specialized in recruiting upper management and board members to early stage VC funded startups and larger growth stage companies do.

Eric Hornung 0:38
They bring the knowledge of a large global firm and combine it with the personalized service and attention of a boutique.

Jay Clouse 0:45
They have a dedicated team focusing on the Mountain West and Midwest emerging tech markets. So no matter where you are in the country, if you’re trying to hire top level talent, SPMB can help you out.

Eric Hornung 0:56
If that sounds like you, you can go to to learn how they are closing hundreds of C level searches annually.

John Gannon 1:11
Because of the way this market is, and just the level of you know, frankly, capital that’s that’s going into it, there’s a lot more creative ways to kind of get involved in the ecosystem.

Jay Clouse 1:26
The startup investment landscape is changing. and world class companies are being built outside of Silicon Valley. We find them, talk with them, and discuss the upside of investing in them. Welcome to Upside.

Hello, hello, hello, and welcome to the Upside podcast, the first podcast finding upside outside of Silicon Valley. I’m Jay Clouse, and I’m accompanied by my co host, Mr. new face of finance himself, Eric Hornung.

Eric Hornung 2:06
Jay, it is a new day, were risen. We’re here we’re up. It’s early. And we’re excited about finance. I’m excited about finance.

Jay Clouse 2:14
When will you consider yourself one of the new faces of finance.

Eric Hornung 2:17
We’re still a long ways off. I mean, there’s a stark difference between the reach that the group that I have deemed the new faces of finance has and what we have here are an Upside, but we’re progressing.

Jay Clouse 2:31
We’re progressing. you’re progressing.

Eric Hornung 2:33
And here’s the thing about the new faces of finance, it’s always changing. There’s always new faces popping up. When I started this concept. Could you have said that Packy McCormick was a new phase of finance? No, he wasn’t even around. But now he is. Now he’s one of the top dogs. So you never know what’s happening.

Jay Clouse 2:50
New people breaking in all the time. And people need help breaking into places like finance places like VC these are some opaque areas that take a little bit of guidance to figure out how to get into this space.

Eric Hornung 3:05
What’s the curriculum to break into VC, I feel like when I was looking at going into it, it was just read a bunch of books accidentally start a podcast, and then maybe it would work out.

Jay Clouse 3:16
And we still haven’t broken into VC. But maybe if we would have spent a little bit more time reading the blog of today’s guest, we could have gotten there because today we are speaking with John Gannon, the co founder and general partner of Going VC. Going VC was founded in 2016. with the goal of providing individuals with a more concrete pathway into venture capital, it has continued to grow into a vibrant, collaborative and inclusive community of like minded individuals who have the common goal of advancing their careers in the field. Eric through Going VC, John has mentored 1000s of current and aspiring VCs with his career blog, and has subscribers from top firms like Sequoia, KPCB and Bessemer.

Eric Hornung 3:57
Jay, I feel like this is the kind of blog that we have heard about so much, or I have whenever people reach out to me, they’re like, Hey, I’m getting into VC. I’m already doing the John Gannon thing. I’m already subscribed to his blog. That’s like, you know, I said, How do you get in earlier? This is really kind of step one, you subscribe to this newsletter.

Jay Clouse 4:16
I think you actually put John on my radar years ago, at this point, one of our early aspirational guests that we kind of let slip through the cracks. And now we circle back we’ve closed the loop. And I’m excited about it because people who want to break into VC typically are trying to live this one life they have to live the best way that they can.

Eric Hornung 4:34
And if you want to learn how to live the one life you have the best way you can you can visit our friends at Ethos Wealth Management in the to learn more. Here’s the thing about that early those early days, Jay, when we were sending out some cold emails, we had our little reach list. I feel like we’re starting to cross a couple of them off. There’s a couple out there though. There’s a couple out there just hanging for us to you know, have a podcast.

Jay Clouse 4:58
That’s right one day at a time. I will make them all guests of the pod, get them in the pod folio. But first today we’re going to speak with John, let us know what you think about this episode. You can tweet at us @upsideFM or email us And we’ll get that interview with John right after this.

Eric Hornung 5:16
I hate that we’ve demonized scheduling links, Jay.

Jay Clouse 5:19
Scheduling links are actually one of my favorite things. I love the ease of someone saying, here’s where you can book a time with me. And then I can choose when it’s best for me too.

Eric Hornung 5:27
Whenever I get an outreach, and someone says what time looks good for you. I asked them hey, do you have a scheduling tool? And you know what scheduling tool I wish they had? Which one is that? It’s a new scheduling tool called SavvyCal. SavvyCal makes it easy for both parties to find the best time to meet.

Jay Clouse 5:43
SavvyCal makes the scheduling process even more savvy than any other scheduling tool that I’ve seen. And I mean that it makes it so easy to personalize your link, you can say, Hey, this is a meeting time for Jay and Eric. And it just looks so professional, so sophisticated.

Eric Hornung 6:00
So much so that we’re going to be using it for Upside going forward. And maybe even rolling it out to the Upside network.

Jay Clouse 6:06
You can use SavvyCal as well, you can sign up for a free account at That’s And when you’re ready to upgrade to a paid plan, you can use the promo code upside for a free month.

Eric Hornung 6:28
On Upside, we like to start with a background of the guest. So can you tell us about the history of John?

John Gannon 6:34
Sure, I’ll try to go through it as quickly as possible. So we can hit some of the highnotes.

Jay Clouse 6:38
Yeah, hit the high notes.

John Gannon 6:39
Yeah. I grew up in Massachusetts, go Sox, really, you know, had a very kind of typical middle class upbringing there. And my introduction to the working world was actually in retail, I worked at a place called Filene’s Basement, where I was basically putting clothes on racks and helping people in the store. I also had other jobs worked at a fish market that was down the street from my house, which was definitely a formative experience. But I sort of meander my way into tech during high school. And this was back in the day of dial up Internet service providers to to sort of put a put a date or a kind of a date range on it. And I was was immediately hooked. I just really enjoyed technology, I really enjoyed seeing how it affected people’s lives. And and that was really the start of my tech career in high school, and then went off to college, studied computer science, and then did a bunch of things from there, really, mostly in the software industry. A lot of focus on internet infrastructure worked at companies like VMware, Amazon Web Services. And then as we kind of got more mid career, I got more mid career, I took a turn into the startup and venture world. So I ended up going to Columbia Business School, and really focusing my time they’re trying to get into the venture capital industry. And this is back in 2008, which 2007, 2008, which, as you know, there were a lot of those firms a lot less capital, very different kind of market for startups and venture and venture investment. So that was really when I kind of got on the path to starting the blog, and the newsletter and sort of all the things that came after that was really based out of my own scratching my own itch, when I was trying to break into venture capital and just sort of how hard it was and how there really wasn’t a lot of information out there and trying to open that up to to other folks so that they could take advantage of that and use it in their own job search process.

Jay Clouse 8:51
Yeah, talk a little bit about the beginning of the blog. Was that a medium for you to try to display your skills as someone that could get into venture? Was it to to document your process, trying to get into venture? What did you think the blog would be?

John Gannon 9:03
Yeah, so the blog was actually really just me saying, Hey, I found a lot of interesting stuff that really helped me when I was in my VC job search. And so I wanted to take those same resources and simply just curate them and put them out there for other people to be able to use there was no grand plan in terms of I want this thing to to grow into a business or anything like that. It was it was purely from the fact that frankly, I just got excited about helping people with jobs. And I’ve always been that kind of person who’s helped people with their job searches. I got a taste of blogging and Business School Actually, I blog throughout my business school experience was not as widely read as my current blog and and newsletter that I have now. But it was a great experience. It really kind of hooked me on the whole idea of blogging and being able to reach even if it’s just a small audience and really connect with them, and really help with I’m like, I would be maybe at a business school happy hour while I was in school and someone say, oh, like, you’re the guy who writes that business school blog about Columbia Business School, right. And so those kinds of interactions really kind of hooked me on blogging. And then when I got out of school, I had the venture job, I saw there was another kind of opportunity really, to help people. And that’s when I started, what’s known as the John Gannon blog, or the VC Careers blog.

Eric Hornung 10:26
And why did you. Why did you stick with it? After all of that, like, what was the impetus to? I mean, you have a venture job, you working in tech, you went to business school, you did the whole thing. Why keep that running? And keep essentially a full time job on the side?

John Gannon 10:39
Yeah, I, that’s a good question as to why I continue to, to sort of do what I do in terms of the blog, in the newsletter, I just, and you guys probably can empathize with this, because you have a podcast here and you’re producing things regular, you’re making things regularly, I do definitely enjoy the creation of content and trying to think of like different angles that other people haven’t thought of, and trying to, to sort of educate them and help them in in say things maybe a little bit differently are giving a different spin to it. But frankly, a lot of it and this is I think the trick to some of this stuff. And I think you guys might be able to, to sort of see this in your own work as well, is that just forming that habit of creating something on a schedule? on a weekly basis? Once you get in that groove? It’s It feels really weird to get out of it. And it’s funny, I’d love to talk to my wife about this. I’m like, Well, you know, today I like I have to write the newsletter. She’s like, What do you mean, you have to write the newsletter? I’m like, No, I actually have to write the newsletter today. So I think once you do it enough in your brain, then it gets trained in that way, you really can kind of lock in and like I don’t, I can’t see myself not doing this right. I can see myself doing this for another 10 years, 15 years, simply because it’s, it’s become a habit, then the challenge becomes how do you keep it fresh and creative. And I’m always looking for ways to kind of mix it up and try some new things. In sort of the medium that I that I work in.

Jay Clouse 12:12
I’ve been writing for a few years now. And every, at least every year, if not every like six months, I asked myself like, what, what am I doing here? How do I continue to make this more narrow and more specific and more referable? Even? Have there been any notable changes or differences in the way that you’ve thought about the blog over the years?

John Gannon 12:32
Yeah, I think one thing that I am much more proactive about or and started doing, I would say a few years ago, is being more deliberate in terms of seeking out different and diverse voices that I would highlight in the content that I was creating. So say five years ago, I would just look for things that I found just just interesting. But I wouldn’t really seek out voices that weren’t necessarily in my Twitter stream by default, right. And I started to do that, and put some of those things that I that I find into my newsletter. And that all the things that I put in are things that I genuinely like, it’s just that now I’m putting more of a deliberate effort into just looking in, you know, sites, blogs, Twitter, streams, etc, that maybe I wasn’t looking at before. And so I think that really helps my readers get different perspectives, and also helps me right, I get different perspectives as well. And I think that’s a good and healthy thing and helps us all learn.

Eric Hornung 13:34
Talk to me about turning it from the blog itself into, like, how did Going VC launch out of the VC Careers Blog.

John Gannon 13:43
So Going VC, like, I think any good startup was a initially a side project. So I had been running the newsletter in the blog for many years. And I had started to create some products to help folks who were trying to break into the business. And I would say 99% of the folks who are on my email list, they’ve leveraged all the free content and things that I create, and they’re able to get results with that, which is awesome. But there’s that that one person who wants a little bit more, right, they want to go a bit deeper. Maybe they want a more interactive experience. So I ended up rolling out some online courses and and some coaching as well one on one coaching. But what I found is that there was there was still a gap and the gap rows really, when I thought back to my experience trying to break in VC when I was in Business School, there was really no community to plug into. So when I was at Columbia Business School, there were maybe three or four other people besides me who were like really wanted to get into venture capital. And so we were like kind of a tight knit group, but it was three or four people. Right. And so I saw that there was an opportunity where I had built An audience around folks who are looking to break into venture capital. And also, because I’ve been at it for a long time, there were venture capitalists in my audience as well. Right? So maybe they had read my newsletter, and then three years later they they in venture and then two years later, they’re a principal or something like that, right? So that dynamic, I said, What if we could get on a weekly basis, VC job seekers, and VCs, basically, to just hop on a, like a zoom call, and just have that VC share some of the specifics of their background, their sector focus, maybe some specific aspects of how they do they their job, right, and just make it like an interactive experience. And let’s spin up a Slack group too. And we’ll put all the folks in there, and let’s kind of see what what happens. And so what ended up happening was, was ultimately going VC Cohort 1, we are actually right now is are recording in the middle of the admissions period for going VC Cohort 9, and we’ve had 300. Plus, folks go through that program, and over 40% of them end up working in a venture type of role. So it could be a VC could be a venture studio, and accelerator, things like that. And yeah, it just sort of again, was just just a side project, in a sense, saw a gap in the market, and really been able to scale it over the last couple of years by partnering up with my co founder who came in and basically runs the business as as the CEO. And we work together to scale going BC, but his focus is really that day to day operational aspect. And then for me, I really chip in with the pieces that are sort of specialized to me in terms of my network, and some of the things like that, that I’ve just built that brand over the last, I guess 12 plus years now, in the VC space.

Jay Clouse 16:51
40% placement success rate seems really high for this industry. What types of on ramps does the program provide? Or how much of that comes from student outreach after the program versus the program has now surrounded you with people who can help get you into this industry?

John Gannon 17:07
Yeah, so in terms of the success rate, in terms of people getting jobs, there’s a few different pieces of the program that really contribute to that. I think just number one, the types of folks who apply for the program, you don’t apply for a program like this, unless you were very, very certain that you would like to work in venture capital, right. So there’s sort of a self selecting aspect there. We’re just getting these like super motivated people from all walks of life, right? It’s not just folks who went to Stanford, or are going to be getting an MBA at Harvard, right? We’ve got folks coming from all different backgrounds all over the country, and even internationally now, which has been kind of a surprise, frankly, that we’ve got folks now who are applying from different geographies and enrolling from different geographies. But in terms of like the the pieces of the program, and the alumni network that really helped I think drive success rate. So there’s certainly an educational component. So we have a 16 week educational program, where we’re basically bringing in VCs, as well as folks from the venture ecosystem with relevant experience to really teach the different aspects of venture, be it sourcing, due diligence, cap tables, right, all these different pieces that you need to know as an investor. We’re covering them in that 16 week program. And we bring in folks from a variety of different venture firms and organizations, some are folks that that maybe are just getting started and not as well known. And then we’ve got other folks. Just last week, we had Elizabeth Yin from Hustle Fund, who came in and gave a session and talked about fundraising. We’ve had Tomasz from Redpoint, come in and talk about SAS and metrics, right, so, so bringing not only that educational experience, but also allowing folks to really expand their network by helping them get in touch with these these folks in the industry, you have had some success is a big piece of this. The community aspect, right is another pillar, which is super, super important in that in a cohort, maybe we have, say 70, 80 people, right, who are all focused on that same goal. And so there’s a tremendous amount of leverage that they get, because we’re there in essence, in this community, and everyone is really pulling each other pulling for each other, to succeed in that community. And so it could be anything from, hey, I’m interviewing next week with a venture fund in the valley. And I need to work on a investment memo. Does anyone have any tips or samples, or it could be Hey, I’m looking at Ico’s in blockchain space and could really use someone to potentially give me some feedback on some of these things that I’m evaluating. Right. So all of that kind of comes through the community. And then one more big piece of this is we actually going to see it myself. It’s my partner but we actually have a team right? part of that team is our Career Services team. And so they are focused on figuring out based on someone in the program and sort of their interest goals, where they’re trying to go, is really helping them to make sure that they’ve got their resume in a good place to identify that when there are firms that are hiring, to be able to potentially give them a route directly through another member in the program to connect with that firm or through a could be members of the staff or the team as well or myself. Right. So kind of opening up the network and really tapping into that in a major way for folks on the program. That’s, I would say, the third piece of really what drives that success rate.

Eric Hornung 20:46
How’s that network changing on Upside, we’ve seen, at least in the last two years with at least become more on our radar that there’s a lot more innovation happening in like early stage investing, there’s crowdfunding, there’s syndicates, there’s micro LPs, there’s rolling funds, there’s maybe more professionalized angels. How’s all that playing into what you’re seeing in terms of a network? And in terms of optionality for people within your audience? And is it affecting best practices at all?

John Gannon 21:18
Yeah, so it’s a good good call out. And I probably should have mentioned that it’s the fourth piece of what we do and how people see success in the program. But we started Going VC partners, which is our investment arm. And we’ve invested in now close to 20, early stage companies, and the Going VC partners, really is driven by our community. So the company sourcing, diligence, etc, is actually done by the community, the members of the program. So they’re actually able to pick up experience in all of the aspects of venture all the way down to check writing. They don’t they don’t have to write a check, right. But but you know, we write a check. And we’ve built in, in essence, an LP network that writes checks into these companies. And so today, we’re using sort of an SPV model, which you’re I’m sure pretty familiar with. And you know, in the future, we’d like to go down more of an institutional road and be able to deploy capital in that fashion as well. But in terms of the creativity, like you were saying, Yeah, there’s, there’s a, we even see it, folks within our community are spinning up their own spvs. And they’re investing through that mechanism and forming their own LP basis, we see that actually quite frequently now. So yeah, I think there’s a lot of innovation there, just in terms of like, I think there’s just a lot more folks that are kind of getting in business, even if it’s for a deal or two a year to be be running some kinds of syndicates. Also, I think what we’re seeing on the syndicate side is they’re actually opportunity to really team up with other syndicates. And that was something that was, frankly, a surprise to me, I had always just sort of outside looking and thought, like, oh, like, there’s a syndicate and they sourced deals, they invest in things. And that’s kind of it. But there’s actually collaboration that goes on. And we’ve seen that firsthand. And in Going VC, actually, in some of our investments as well, which has been been really interesting. And something I didn’t expect

Eric Hornung 23:15
A lot of Going VC and VC Career bout getting a job in venture, do you see anyone, or how often are people coming out and like launching a fund instead of getting a job.

John Gannon 23:28
So in terms of folks who want to work in VC versus start their own fund, we definitely slant towards folks who either want to break in and also in the recent, I’d say, a couple of years, we actually see early career VCs, we’re looking to just kind of grow in their career during the program as well, which was only we didn’t necessarily expect, but it’s been really great to have folks like that involved. But in terms of the split between folks who want to join a fund versus launch a fund in our program, it definitely skews more towards the joint fund crowd. And that’s, I think, just by virtue of my audience, and a lot of folks who follow me, follow Going VC right are in that in that boat. But we do have folks who are actively looking to certainly start their own funds or their own syndicates. So we we see some of that too. And I think that that actually is it’s sort of like a way to kind of hack your way into venture and because of the way this market is, and just the level of you know, frankly, capital that’s that’s going into it. There’s a lot more creative ways to kind of get involved in the ecosystem, be it creating your own SPV is you also see accelerators, right who they’ve got their accelerator but that makes they create a fund that’s that’s kind of related to it. Right? There’s there’s all these different sorts of dynamics that are that are going on, and I think folks in Going VC really viewed as a way to expand their network, expand their educational base, expand their deal flow, right? If they are in our we call it the investor program, then they’re definitely seeing additional deal flow as well. And I think all those things kind of can help someone whether or not they want to join a venture firm, or if they want to start their own fund and kind of everything in between.

Jay Clouse 25:23
You mentioned, there’s a lot more capital the market right now, you know, there are new firms getting stood up all the time. So, in my mind, it seems like since you started this blog, in 2007, 2008, the supply of VC jobs probably increased, but I imagine the demand for them has continued to increase as well. So I just love to hear from your standpoint, some of the trends you’re seeing in available VC Careers, for people who are trying to break in.

John Gannon 25:47
The supply of VC jobs is definitely much higher than back in, say, 2008 2009. When folks didn’t even really post jobs, right, it was just literally you just talk to every firm, you can, hopefully, hopefully someone was hiring. One thing that is, I think, awesome in terms of people are looking to get venture experience or venture type experiences, there’s, there’s so many different ways now, in the sense that you could volunteer for an accelerator, if there’s a VC who runs some kind of a meetup, trying to find a way to perhaps volunteer for that and help out there. A variety of firms are doing fellowship programs, which are sort of internship, like, but they’ll wrap some programming around it as well, right? That’s kind of a new thing. And there’s a lot of opportunity there as well. And it’s just more ways for people to get that sort of like get on that first rung of the ladder, right? Because that that sort of first piece, that first thing that you can kind of get in your resume or talk about, right, that’s the thing that you that you build on. And I think the great thing about venture in 2021 is that there are actually a lot of those opportunities. Now, there’s more visibility as well in terms of venture as a career. So I think on the demand side, that definitely increases. But I think that the new opportunities through some of the means that I mentioned, they sort of outweigh that. And I think overall, it makes it for a more kind of robust ecosystem of VC and VC type opportunities. The other thing I would say is, there’s kind of hybrid models where you’ve got folks who are their operators, but they also do a little angel investing, right? Like there’s a lot of different ways to to kind of work your way in the ecosystem. And I think, kind of being open to some of these possibilities, and not just getting locked in on the idea of like, like, I must get a venture job, that actually might not be the right, the right next step, the right next up might be you maybe writing some of your own checks in startups. So there’s there’s a lot of different ways to go out. And I think being open to the fact that there’s a lot of different paths to go down is pretty important for someone who wants to make a career in the venture ecosystem.

Jay Clouse 27:58
Have you developed any theories or themes around what makes somebody particularly adept to go into VC.

John Gannon 28:05
So one, one thing that I tried to do when I’m talking about how to get a VC job, or kind of how to position yourself in a way that will make you a compelling candidate, I try to where possible, put in the sort of a framework, so people can kind of use that as a way to map their experience to that framework, and then fill in any gaps if necessary. So one of the frameworks that I like to use is, I call it the five legged stool. So there’s five things that I think that VCs care about. And those five things are deal flow, right? They care about their own investors, like getting investors for their funds, maybe if you’re like Sequoia or something like you don’t care because you got people banging down your door, but most VCs, right, they need, they need capital, helping portfolio companies with hiring is another aspect. That’s something that a lot of VCs, either claim it’s a value add or they they really want to try to add value in that way. So that’s another leg of the stool. And then if you think about portfolio company, m&a, or partnerships is another aspect that’s like quite important for VC. And then the last one is following financings. So I have a company I’m a VC, I do Series A as well, like that company’s gonna do a Series B, right? And I need to be as helpful as possible to help them to get to that next milestone, because also, that just means that my investment will get marked up, right. And it’s sort of it’s just part of the job as a as a VC. And so what I like to have people take a step back and think about is, hey, out of those five legs of the stool, like what are the legs that I have the most ability to contribute to right and it totally does. depends on your background. Like, if you’ve worked in the family office space, well, you might have a real strength around the LP side of things. Whereas if you have a really strong network in a certain vertical or certain functional area, maybe a portfolio hiring piece is really where you stand out or that leg of the stool. And so as someone who’s looking for a VC job, you state, take a step back, look at those five legs, and kind of figure out where your strengths are, that can be a good place to really lean in and sort of leverage in your search.

Jay Clouse 30:35
What about any psychological predispositions? Are there any patterns that you see in that way for people who can approach any of these legs of the stool?

John Gannon 30:44
One thing that I remember very clearly was, when I was in Business School, there was someone who was a few years ahead of me, who graduated, he went on to work in venture at a couple of really good firms. And he said to me, John, if you, if you like the process of searching for a VC job, then then you will like being a VC. And consequently, if you do not like that job search browser, you will not like being a VC. And it’s very, it was very true in terms of what I saw in practice. Because if you are looking for a VC job, you need to do many of the things that a VC is already doing. Today, you need to be out there, finding interesting companies that you think are investable, you need to be helping them connect with capital, connect with people who might want to go work for them with potential partners and customers, right? If you don’t like doing that, you are just not going to like working in venture. And so I think folks who take to the search with that mindset, and also realize that this could be a, this is not a six month job search, right? This could be something that that takes you a few years, and there’s a few different stops along the way. And folks who kind of go into it with that attitude that, hey, that’s okay. And you know, I’m going to sort of enjoy the journey. I think of the folks who who end up being successful.

Jay Clouse 32:12
Looking at your LinkedIn, it seems like you’ve always had a collection of things going on at any one given time, along with the blog. And along with Going VC, I have to think at some point, you’ve thought about what if I just only did Going VC and only did the VC Careers blog, and seemingly decided not to do that? And I’d love to hear your thought process as to why or why not?

John Gannon 32:33
Yeah, it’s, it’s a good question. And one that I particularly of late have really thought a lot about. So I don’t have a direct answer on this one. But I can tell you what I like about having multiple sort of balls in the air, which is that I think it’s really exciting when those different balls kind of complement each other. So the fact that I’m a product manager, and there’s a company, maybe in the dev tool space, who we come across through going VC Partners, and being able to kind of look at that company in a unique way with a specific set of experience and be able to have a strong opinion on that and also be in a position where I can be really helpful to the founders of that company. That sort of interdependency, if you will, is really exciting to me, on the flip side is that you don’t always get that interdependency. It’s not like every day that that kind of thing is happening. Right? And so there’s kind of a push and pull just when you’re working on a few different things. I think, obviously with going VC in my blog VC Careers, technically, they’re, they’re separate. But but obviously, a lot of the things that I do for one or the other, they they they very much are interdependent, and and and sort of one drives the other in a way. So yeah, like I said, that’s something I’m kind of thinking through myself. But yeah, I don’t have a solution to the puzzle just yet.

Eric Hornung 34:01
As we look into the end of 2021, getting into 2022 returning back to normal times, what are what are you excited about with VC Careers, Going VC, anything we should be looking out for?

John Gannon 34:14
Yes, now that the world seems to be or I should say, you know, parts of the world seem to be getting back to more more normal normalcy. I’m looking forward to being able to get out there and really connect with people eating sort of in person and getting that that muscle going again, because it’s definitely atrophied over the last several years, or not several years, but several, several months that we’ve been in this pandemic, so.

Eric Hornung 34:43
It felt like several years.

John Gannon 34:44
Yeah, yeah, for sure. And so, I’m looking forward to kind of getting back out there a bit more. I also am really curious about how the world will take the lessons that were learned around remote work, and how They will be applied or not applied. So, like I alluded to, I’m a product manager at DigitalOcean, which is a company that has been, I would say 50% ish remote for, almost since the beginning. And so when the pandemic hit the remote work, culture structure, everything was already in place. So execution wise, we just kind of kept chugging along. But I have friends who work at larger, huge publicly traded companies where their idea of remote work was, you know, basically, you’re on the same number of meetings every day, you’re just staring at a screen to do it versus in a conference room. Right. And that is not remote work. That is just like punishment, right? And so I’m excited to see do do, do bigger companies figure out is there a way that they can actually take the best parts of remote work and just really make a better workplace better environment for for the people that are in those companies. And also give people options? I think people, there’s some people were like, Oh, I gotta get to the office gotta get back. And like, that’s cool, like the those folks should have. There should be companies and cultures that that are really, they want that, right. And I think folks who want that will gravitate towards those companies. But there’s going to be other companies, right, which have more of this remote, first kind of operating model. And those are going to attract different kinds of people. So it’ll be interesting to see where all that shakes out, I think it’s gonna take a couple of years. I also think there’s a lot of opportunity. And I think teaching people how to work remotely, I actually haven’t released like, it’s sort of like, yeah, we use Slack. And we use Zoom. But that’s not that’s not actually a remote work operating system or way of working. It’s just like, here’s some tools and, and figure it out. So I think there’s gonna be some opportunities around remote work, maybe it’s training, maybe it’s sort of mentoring and kind of networking in a world where you maybe you’re not necessarily going into an office as much. So I think there’s some exciting opportunities there potentially venture investable, as well.

Jay Clouse 37:13
We started this interview, and you were talking about the newsletter, and you liked having the practice of publishing on a on a weekly basis. A lot of the reason I was excited about this interview and enjoyed this conversation so far as I relate to you, and that you are a creator, you’re an educator, but you’re playing in the VC space. And a lot of times, VC and creator economy seem like not contrasting, but very separate camps with a few people and firms that overlap. So I just love to hear your relationship to the creator economy and how it relates to the work you do in VC, if at all.

John Gannon 37:46
Yeah, and I love that question. Because it’s something that I’ve thought about a lot. And I think the when you read the blogs, and TechCrunch, etc, nothing against them when they talk about the creative economy, but they really do focus on it’s almost like creator equals like someone on YouTube, right? And I don’t, I don’t agree with that at all. Like I do consider myself a creator and coming up with different ways to to educate different ways to sort of help the ecosystem. You know, for example, yes, I do a newsletter. But four years ago, I said, Hey, you know what, I think we need to have some more transparency around salaries and venture capital. So I launched or created the Venture Capital Salary survey, right. And I think that that that is a it’s an act of creation, right? made a thing, put it out there in the world. And so I think there’s creators in, in sort of every, every space, right? You could be a creator in the music space, you can be a creator, doing stuff on YouTube, you could be, you could be a creator that creates on Instagram, you look at Thingtesting, for example, as a company that now has raised venture money from Forerunner, one of the top sort of ecommerce focus firms out there, but that was really a creator who started on Instagram and was just sort of highlighting the brands and things that she found interesting and put that out there in the world. Right. And I consider her a creator as well. So yeah, I think we need to broaden sort of the the aperture in terms of thinking about creators and I think for VCs who look at the creator economy, I think they really need to take like a wider look, right? It’s not about just tools that can help a YouTuber make more money, right? There’s actually an enormous market out there just even beyond the folks that are RSA may be doing stuff on YouTube, or podcasts or things that are like more commonly associated with the word creator.

Eric Hornung 39:43
John, this has been awesome. If people want to learn more about you or VC Careers are Going VC, where should they go?

John Gannon 39:50
So if people want to learn more, they can go to or and there’s like a said a ton of free reef resources about VC job search about venture investing, and sort of everything that wraps around those two things are out there and available. And please go visit, take a look, download, read, learn, and then, you know, share, teach, get it out there and make sure that we can kind of lift up the whole ecosystem in the process.

Jay Clouse 40:23
Eric, do you know what my favorite part about podcast advertisements is?

Eric Hornung 40:27
That people actually listen to them?

Jay Clouse 40:28
While you read my mind. It’s almost like we’ve done this twice now. Yes, that people actually listen to them. Look, you’re listening right now, dear listener.

Eric Hornung 40:36
And me I’m listening to I’m listening to you, Jay here on the Upside podcast.

Jay Clouse 40:40
And if you have a message that you want to share with the Upside audience, people who care about startups, investing the middle of the country, this is a really great place to put that message.

Eric Hornung 40:49
Because people will listen to it. And if you have an event, or you just want to get something out about your brand, your hiring. This is the perfect place for the That’s our classified ad that can run on one to five podcast episodes.

Jay Clouse 41:05
That’s right. Typically, we lock in sponsors for longer sponsorships, but we wanted to make this accessible to you and your message. If you have a message to share with our audience, go to, and get your ad on the airwaves.

Eric Hornung 41:25
Alright, Jay, we just spoke with John Gannon of Going VC and VC Careers blog, holy hustle.

Jay Clouse 41:32
He’s got a lot of stuff going on. Not only is he a full time Product Manager at DigitalOcean. And doing all this on the side, all of this quote unquote, that is Going VC is broken into the blog, the email list, the going VC Cohort program. He has a lot going on, he has a lot of opportunity. But I love seeing somebody combining two of my loves Eric, which is the startup world, the technology world plus being a creator and figuring out how to build an audience in a space and serve them well.

Eric Hornung 42:03
Are you a Seinfeld fan?

Jay Clouse 42:05
Oh, yeah.

Eric Hornung 42:06
Heavy. You know, George, when he goes worlds colliding? Yes. That was like this episode for you.

Jay Clouse 42:13
That is that is definitely how I felt.

Eric Hornung 42:16
That might be our cover image. So I think that we kick this episode off with the whole new faces of finance concept. And really what that is, is people applying the principles of the Creator economy, which are enabled by this new wave of technology, into finance. I mean, it’s what I’m particularly interested in as well. I’m not as creator focused as you are. But the movements and the momentum there, I think is huge. And I think we can see that in finance, I think there’s probably people applying those same two lenses of technology and media slash creator slash content into other areas.

Jay Clouse 42:54
And it’s having an impact. John told us that I think 43% of going VC members have either worked are currently working in VC accelerator programs, or venture studios coming out of that program. Little plug here, going VC Cohort 9 applications are open right now until July 11. At midnight. So if you enjoyed this conversation with john, and you’re interested in Going VC, aha, wink, wink, nudge nudge, then you might want to go to that Cohort application is open right now for the fall. And I’m terrible at time zones. But I believe it’s 11:59 Pacific Standard Time. So if you are a procrastinator, like I am sometimes, and you’re on the East Coast, you get yourself a couple extra hours. It’s really kind of July 12.

July 12 3am, extra a couple hours, bonus hours. Well, we’re giving you a month of advance notice here, so hopefully you don’t procrastinate that much. Eric, this gave me some vibes of our conversation with Peter Livingston as well. I enjoy hearing these people who are writers kind of first and foremost, but writers who are serving this audience in the tech world a little bit different, you know, John’s not talking about companies directly. He’s moreso talking about ways to get into the investing side, which is good, because there’s space for all of that.

Eric Hornung 44:14
I love this structure, I think that we’re gonna see it applied to a lot of content as we continue this Upside journey, Jay. And I think it’s more of a kind of 10 year trend as well, I think we’re gonna see it hit other industries, we just saw A16z launch future, which is their media arm. I think all of this is going to the same idea, which is that companies see the need for media. Now, to you and I’s point. If you start as a media company, if you start as a content company, is it easier to launch something else or vice versa? That is the age old debate.

Jay Clouse 44:48
And I think we’re building our own repertoire of the five legged stool to use John’s terminology, which I want to just call out here in the outro because I think this is a really good framework five legged stool the components are one deal flow. Two, investors for the fund. Three, helping portfolio companies with hiring. Four, portfolio company m&a, or partnerships. And five follow on financing those five legs can help you go VC dear listener. So, if you are listening to this and you’re interested in getting to that field, remember those five legs think about how you can help a company with them. Read John’s blog, and let us know what you think about this episode. You can tweet at us @upsideFM or email us Hello@upside.FM. We’ll talk to you next week. That’s all for this week. Thanks for listening. We’d love to hear what you think about this episode. So tweet at us @upsideFM or email us Hello@upside.FM and let us know. You can learn more about us and browse our entire back catalogue of And if you love our show, please leave a review on Apple podcast that goes a long way in helping us bring high quality guests to the show.

Interview begins: 6:28
Debrief: 41:25

John Gannon is the co-founder and general partner of GoingVC.

John has mentored thousands of current and aspiring VCs through his VC Careers blog and email list, which counts VCs from top firms like Sequoia, KPCB, and Bessemer as subscribers.

GoingVC was founded in 2016 with the goal of providing individuals with a more concrete pathway into venture capital. It has continued to grow into a vibrant, collaborative, and inclusive community of like-minded individuals who have the common goal of advancing their careers in the field.

GoingVC was founded in 2016 and based in New York City.

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