How To Get A Job In Venture Capital, With John Gannon, Co-Founder of Going VC

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About The Guest

John Gannon is the co-founder of GoingVC and the VC Careers Newsletter. GoingVC is a VC Career accelerator, designed to help you break into venture capital by directly connecting motivated VC job seekers with VC firms.

His newsletter is the largest VC Careers newsletter in the world, and has been running for years, has thousands of subscribers, and includes people who work at top VC firms like Greylock, Bessemer, and CRV.

Talking Points

  • 12:55 — How do you get a job in venture capital?
  • 17:10 — How to pivot careers & get VC’s interested in hiring you.
  • 21:38 — How do VC’s actually make money?
  • 25:13 — The current state of the VC industry.
  • 29:25 — What do investors look got in companies and what should entrepreneurs look for in investors?
  • 31:37 — Breaking into VC.
  • 32:53 — SPACs & VC.
  • 36:33 -Tips to help you land your next job.
  • 45:22 — Advice for young professionals.

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What is the Success Story Podcast?

On this podcast, you’ll find interviews, Q&A, keynote presentations & conversations on sales, marketing, business, startups and entrepreneurship.

The podcast is hosted by entrepreneur, business executive, author, educator & speaker, Scott D. Clary.

Scott will discuss some of the lessons he’s learned over his own career, as well as have candid interviews with execs, celebrities, notable figures and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas and insights.

He sits down with leaders and mentors and unpacks their story to help pass those lessons onto others through both experiences and tactical strategy for business professionals, entrepreneurs and everyone in between.








Read The Transcript (Machine Generated)

John 02:33

So like you mentioned, early in my career, I worked for a company, this was back in 2003, actually, is when I started with them when they were about 300 people. And I was a company called VMware. And that was really my first taste of a true breakout category defining company, and spent approximately four years there. And it was just a complete rocket ship. When a company is growing, basically doubling year over year consistently, it is an amazing career growth experience, because they’re, they’re growing so fast that there’s literally not enough people to do all the work to sort of keep the rocket ship moving upward and to the right. And so I had a great experience there and met a lot of folks who I continue to stay in touch with till this day. The other thing that it really helped me sort of do is when I later decided I wanted to move into the venture capital space after Business School, having been fortunate to be at a category creating category defining company. That was something that was incredibly helpful to me when I was trying to convince venture capital firms that I was someone who could come in and actually add value to what they were doing on day one, and be differentiated in terms of the types of investment opportunities and investment thesis that that I bring, bring to the table.

Scott 04:10

And correct me if I’m wrong, but your path is not a traditional path into venture capital. Because from what I understand, you’re going, you’re an analyst, and then you and you progress from there, right. And you’re just pure finance, and they don’t have careers in tech. So how did that how did you parlay that? Or is that how it sort of progressed for you?

John 04:30

Yeah, I think it’s over the recent years. I think it’s changed a bit. I think what you said was absolutely true. Back when I was sort of getting started in the VC world around 2007 2008, where you definitely saw a lot more people coming up through sort of a finance background, like you said, what we’re seeing now, more so is that people are going out and getting operating experience of venture backed startup, maybe their VP of marketing or they’re up Product Manager or they work in engineering or something like that. And they they take that experience from from the startup and basically, then take those learnings and apply them to trying to break into venture capital. Sometimes it’s because or it’s through the fact that the company they worked for actually was invested by a bunch of venture invested in by a bunch of venture capital firm. And so there’s, there’s certainly a path to sort of connect with, with the investors through those kinds of relationships. But in this market, as well, just given the proliferation of capital, right, there’s a lot of capital out there and just reading TechCrunch every day or really anything in the news, you can, you can see that, but there’s been a proliferation of VC firms of angel investors, and, and sort of hybrids in between. And I think one of the things that I think people maybe don’t know about trying to work their way into the venture capital industry is sure, you can go to my blog, and you can see we post maybe 200 new jobs a month in the VC space. But for all of those jobs, there’s a whole set of opportunities that are actually completely off the radar with firms who just simply choose not to sort of share those opportunities publicly, but end up hiring through their networks and referrals and things like that, which has a variety of challenges as well, especially when you look at VC in an industry where from a diversity inclusion inspector perspective has not done well at all. But but but there are multiple ways to sort of get involved. And one more piece of that, which I think is really important and sort of ties into some of my work with going BC, which is really a platform business where we have a cohort based education program. But tied to that we also have an investment arm. And we’ve gone out, and we’ve invested now in close to 20, early stage companies. And we’ve also built out through our community, a scouting network, where the people who are in the program that they choose to can actually go out source companies do due diligence on those companies. And going VC partners, which is our investment arm will actually invest in in some of these, these companies. And so that’s, you know, for me, at least write a query, I didn’t apply for that job. It’s something we just kind of created as part of, of going VC. And we see similar things now, where you’re seeing angel investors really kind of professionalize their work in a way, where instead of writing 10, or 25k, checks, on a per deal basis, they’re actually rounding up maybe hundreds of 1000s of dollars from people in their network. And then as a single face to the entrepreneur, writing a single check into their company, by basically bringing all along all this capital that they’ve in essence raised for on behalf of that entrepreneur. So there’s a lot of interesting things going on.

Scott 08:02

So let’s so I want to go into some of those nuances of the current state of venture capital. The first I want to just understand because you’ve built out something very impressive, forget the fact that you have tons of learnings about venture capital investment. I guess, why did you even start this venture? Why did you start building this newsletter, this cohort in this community, because you had a successful career? And just walk me through? I guess the timeline a little bit? He said it started back in 2008. Were you still actively part of L capital or another firm at the time? Or were you back into tech?

John 08:37

Yeah, happy to walk through the origin story. For me. It really started in 2006, when I got that phone call from the Director of Admissions at Columbia Business School, saying that I was accepted and that I was going to be enrolling in early 2007. And the reason that was important in the overall journey is because I don’t remember sort of why I decided to do this, but I decided to start blogging. I think it was even that day, about my business school experience. And so during business school, I was blogging frequently about specifically what it was like to go to Columbia, about my specific program. And as I did that, I sort of enjoyed doing it. But I also enjoyed getting feedback, outreach from folks who would come to me either in person or email me and say, Hey, I read your blog. It’s great. learning a lot about Colombia. It’s got great tips. And that really is energizing to get that kind of feedback. And so I knew what that felt like even though what I was writing was really for a very sort of specific and frankly, quite small audience at the end of the day, but I carry that with me when I graduated. Because I went through what everyone who’s gone through a venture capital job search knows is an extremely long job search process. So if capital is not the type of industry where it’s a three to six month third. It’s usually at least a year and maybe even even multi year. And so I spent all my time in Business School, really trying to really trying to break into the industry. And through that process, there wasn’t actually a lot of information out there, like there is today. So, again, rewind like 1213 years, there were folks like Fred Wilson, Brad Feld, who who were blogging, then there were a few other folks. But it wasn’t to the degree today that we have where there’s literally hundreds, if not 1000s, of VC blogs, and a lot more transparency around this information. So during that, that journey, and during that path, and it was pretty lonely one in the sense that I could maybe count three or four other people in our school who actually wanted to go down that same path, is when I got the job, I actually said, Hey, why don’t I create a resource or free resource where I’ll just take the stuff that helped me, and I’ll put it up there. And I’ll make it available for everyone to, in essence, see, and look at and, and learn from? And that’s really where the blog started. And then, over the years, I added job postings, I added the email newsletter, which in retrospect was a mistake to not add that on day one. Definitely, I think I missed out on maybe an opportunity there. But I’m definitely happy with with how things have certainly turned out over the years and, and sort of how it’s grown. And there’s kind of a community around it as well.

Scott 11:39

I think it’s a great resource. And I and I, when I first started did a little bit of research into the into what you do, it was a little bit it was new to me, I’ve never seen anything really like this. And I’m not actively looking for a job in venture capital. So probably if I did a little bit more research I could probably find but you are still the first one that I’ve ever seen who has proactively been putting out newsletters and whatnot in the VC world. And I guess it just never thought I never thought about it as something that had a huge community around it. Like, you know, I, the first thing I mentioned was is people coming from finance going into this career field. So I’m obviously mistaken. And I appreciate that you do this, because I think that a lot of people can pass it operators can possibly make jumps into venture capital and be a valuable asset for some of these firms trying to understand, you know, who’s going to be successful, who isn’t going to be successful, and so on and so forth. So there’s a lot of value. I think that this brings to the table for people that are working in early stage startup and trying to figure out what’s another option or an alternative option for my career. So I guess the question is, you teach these things probably in the cohort in the newsletter, but what are what are some tips for people that do want to get a job in venture capital? What do they need to do? Because you mentioned it’s not an easy process?

John 12:55

Yeah. So if you want to dig into a bit around how just want to actually get a venture capital job, one thing I like to talk about is what I call the five legged stool, and the five legged stool is really a way to think about like, what are the what are the most important things to a VC, because if you put yourself in their shoes, you’re going to be in a much better position to understand what they need, what they want, and how to add value to them. And so in terms of what are those five legs, what are those things that VCs care about? So one of the most important things is deal flow. So finding companies that are investable, and And ideally, finding those companies before other people before it gets competitive. So that’s one aspect. There’s also for their existing portfolio companies, another leg of the stool is, in essence helping those existing companies go out and raise more money, right. So if I’m Kleiner Perkins, and I do a series a and a company, that company is probably going to need a Series B, right? And there’s going to be an investor that that’s going to write that Series B check. And so being able to assist in terms of helping other companies that have already raised venture money kind of go to that next round, is another important piece of the job of being a VC and if you can help a VC with that through your network, that’s another big value add. The third is around the investors in the venture capital funds themselves. So they’re called limited partners. And so limited partners are gonna be high net worth individuals, but if you look at like really big venture funds like the Sequoia is and the Kleiner Perkins is they’re getting their money from large endowment, university endowment. You know, folks like the Rockefeller Foundation, right like a lot of these really large one Expanding institutions are ones that are investing in venture capital. And so if you as a job seeker through your network have access to people in those worlds, for high net worth individuals who are interested in investing in venture funds or in startups, that can definitely be a value add, particularly for newer funds, which are earlier on in their journey, where they’ve not necessarily locked up the Princeton endowment to write them $20 million check, but maybe they’re raising a $5 million fund. And so someone who can write 100k check is actually quite meaningful to them. Right. So that’s another area in terms of adding value. Hiring is another piece. So if I’m a VC and I’ve got, maybe I’m on the board of 678 companies, one of the most important things that I’m trying to do is make sure that company is staffed properly has the best talent. And although I’m not directly responsible for it, my CEOs that those companies that I work with, are going to kind of expect that, I’m going to be sending them really high quality folks who could potentially become employees or executives at those companies. And so if you can help with that, through your personal network, that’s another way you can add value to a to a VC straight away. And then there’s a kind of a fifth bucket, which is around business development, sales, and m&a, which is if you can help a VCs portfolio get in front of people who can buy their products, by their company, or otherwise partner, that’s a big value add as well. So as a job seeker, it’s kind of up to you to like inventory, your network and your skills and your interests and figure out out of those five legs, you’re not going to knock all of them out of the park, but there’s probably a couple that you would kind of gravitate to or have a strengthen. And those are the things that you’d want to lean on in terms of how you want to conduct your search and sort of which firms you might want to approach with what kind of pitch? And then how would you deliver value to them? to really show them before you even have a job that you’re someone who could actually do the job? do you have?

Scott 17:10

Do you have examples of how somebody would would show value? Because it seems like for some jobs, it seems like a simple project or or something could show some sort of value to a hiring manager. But for a venture capital firm, would it be an introduction to somebody? I guess it depends on what what value you bring to the table. But it seems like it’s a big ask before you even sit down with somebody to show value. So you have an idea of how you could do that. To make sure I understand the question, you’re asking how specifically can a candidate show value and one of those area?

John 17:45

Yeah, sure. So deal flows is is a great one to talk about. Because it’s one that critical, right to a VC, they have to make new investments. And so they need deal flow, they need to be ideally getting to these companies before other folks do. And so an example would be, maybe you went to school with a bunch of folks who are out of that group, there’s a few who, maybe they started their own businesses while they were in school. Or maybe they were just like insanely smart. And they were the kind of people where you looked at and said, you know, that person is they’re gonna really do great things in their career. So if you are in touch with those kinds of people from maybe your childhood, and to be from your college experience, gonna be people you’ve worked with previously, kind of keeping tabs on what they’re working on. And if you see them working on a new thing, that looks like something that could fit into the venture backed startup space, ie a software company, an internet company, right, those those types of things, then, if you’re trying to build relationships with VCs, those are the kinds of folks where you want to try to be that connection, basically, between the people from your network, and, and the VC kids is very compelling. If you’re starting to develop a relationship with a VC, to be able to come down and say, Hi, you know, this is, I’d like to introduce you to my friend, Jen, she started this amazing software company, she was at the top of our class at Penn State. And, you know, I really would highly recommend that you take a look at this company. And oh, by the way, they’ve already got some paying customers or, you know, whatever the case may be in terms of their status, like, that is a great way to both deepen a relationship with a VC but also can can give you a reason to get in touch with VCs, as well. One of the things that I talk a lot about and we focused on an ongoing VC program is developing what we call an investment thesis. And an investment thesis is really your sort of unique view on a certain sector or market. And by sort of a well defined view, what I mean by that is having the ability to deep dive on that entire sector, the companies that are in that sector, both the big ones that are maybe public, and also the smaller ones that are just getting funded, and everyone in between, and then having a really specific angle in terms of which types of companies in that sector you would invest in and why. So as someone who’s trying to get in touch with VCs, or get them interested, it’s, it’s also quite compelling to actually create a, almost in a written form. pretty commonly, you might see a 1520 slide deck that really articulates that thesis, and I’ve seen folks in our program, create these investment thesis, sort of document them and then share them out on LinkedIn. And I just emailed my list about this actually, a couple of days ago, there was a team of folks who were in my going VC program two people, they created an investment thesis around ag tech, they posted it. And the the post got over 30, I checked the other day got over 30 comments and over 100 reaction, and even got an inbound at least one inbound and feeling when I know about there could be more from a VC, you said, Hey, I saw this investment thesis, I’d love to talk to you, right, which is what you want. But like that is going the other way where they’re coming to you, which is obviously superior to you going in and sort of asking someone, if they have any kind of opportunity.

Scott 21:38

Very interesting. Thank you for breaking that down. So the one other thing that I really wanted to unpack, because again, if somebody isn’t in this space, they may not know how to VCs make money. And I got this, I got this point, I was reading your blog, and I was learning about Carrie and I don’t know much about Carrie. So I’m curious about where the money comes from? What are the expectations going into a career in venture capital? Are you expecting to make as much money as I’m assuming somebody would presume they would in venture capital? Which outside looking in? It seems like they they’ll do quite well? Or are the expectations a little bit out of touch with reality?

John 22:20

Yeah, for for a junior investment professional, there’s probably better ways you can make money. So it definitely wouldn’t say you might do better as an investment banker in your early career than you what is the VC for the funds that are successful? They are generating carried or carried interest, like you said, and sort of the way it works with a high level is these these VCs, right, they have investors in their own funds. Right? So let’s say they go out and raise just to keep the numbers simple, a $10 million fund? Well, the way carried interest works is if they invest that 10 million, and then they get back that 10 million, plus another 10 million, right. So they’ve basically doubled the double the money, and I’m simplifying it. But there’s a little more nuance in here. But that’s basically how it works. So, so that 10 million in gains, what the carried interest is, is it’s a piece of the game. And typically, with most venture firms, the that percentage is 20%. So we talked about 10 million in gains 20% would be 2 million. And if you’re looking at early stage venture capital, it could be 678 10 years if a company actually sells right and generates returns, right, while we flame out. Yeah. So in terms of a way to get rich quick, it’s definitely not that because you need to have a fun that generating positive returns. And like I said, it takes a long time for that to happen. Now, for funds that are larger. They it can be more financially lucrative, even without the carry from the perspective that if you look at a firm, like a very large firm, like Sequoia their lifetime as a fund by 2 billion, right. And the other piece of VC comp is it comes out of the they call it a management fee, which is like typically around 2% of the total amount of capital. And it’s it’s taken out each year. And it kind of trends down over time because the investment cycle sort of slows down as you deploy more of a capital. But if you think about a firm that maybe has two or three funds running in parallel, which you often see because a firm may raise a fund and then raise another one in two or three years. Those management fees kind of stack up and so salary wise at the larger firms. You can definitely expect to have a base salary. That’s a, you know, that’s a bit higher than at a firm that say maybe only has $50 million in assets under management, there’s just not as much of that that 2% is just a lot, a lot smaller

Scott 25:13

is because you said there’s a surplus of capital, because we see we see so many companies being invested in is this. Do you feel like the the, the industry is reaching a point where many of the investments will no longer see positive returns or fizzle out or flare out or die out? And there’s poor investments being made? Like one notable is we work and obviously, that’s a sort of like a Hollywood style investment that didn’t didn’t go so well. So do you see more of these events happening? Or do you think it’s a healthy market and the companies that are being invested in are going to yield the returns that are expected? I just want to take a second and thank the sponsor of today’s episode, HubSpot. HubSpot. CRM is the easiest tool you can ever find. To align your team. There are two features that you need in a CRM that optimize every activity your team does. It’s the ability to communicate meaning chat, email, etc. messaging, as well as a unified system of record. Your company’s gonna use a CRM to manage conversations with prospects and customers throughout all stages of the buyer journey. And as your company grows, these conversations get a little bit more difficult information may get lost communication may be disjointed, and HubSpot solves all that using HubSpot, as your CRM makes sure that all of your communication and your records are unified across your entire organization. Meaning that from when you first have that initial touch point with the customer, and they enter your funnel all the way through to when they actually sign that contract. And after with customer success. Every piece of information every bit of communication is aligned and congruent across your company. You can install live chat on your website and allow sales or support to talk to prospects directly. You can send marketing emails on behalf of a sales rep to complement their outbound campaign. You can allow prospects to book meetings directly from marketing emails write into a sales reps, calendar and all the interaction all the communication is seamlessly documented into your HubSpot CRM so that if somebody else has to look into an account or to help out, they know exactly where the last person left off, best of all, with HubSpot, various price points and flexible pricing, any company at any stage can take advantage of the various features that HubSpot has to offer, starting with free and allowing for more scalability and complexity as your organization grows, learn how to scale your company without scaling Alright, let’s get back to the show.

John 27:37

With with so much capital going into the industry as of late you, there’s, and I think this would be true even rewind four or five years ago, like there’s always going to be companies that that maybe shouldn’t be funded, but but someone’s willing to fund them. So they they raise money, and many of those companies will will flame out. But I think what’s maybe more interesting is that valuation is sort of the price at which the companies are being invested in are universally off across the board. So later stage companies pre IPO companies, growth, equity sort of stage companies, those valuations sort of started to go up, I would say first in the last few years, but now we’re seeing a trickle down where even companies have the feed and pre seed stage pre seed stage are seeing those valuations up, I couldn’t quote you an exact percentage, but they’re definitely higher directionally than, say three or four years ago. And so what that means for the VCs is, in some cases, because they’re not able to buy as much ownership in these companies for the same amount of capital, the return profile is potentially going to be lower. Now. vc is his business. So if they get if they invest in the next Uber, if they made a billion versus 900 million, like, you know, it sort of comes out in the wash. And, you know, I don’t think anyone’s gonna complain if they returned, you know, 5060 times the amount of capital in a fund to their investors, which that would be a smash hit, by the way, that doesn’t happen all the time.

Scott 29:25

Now, what about what about for the investor though, like flip flip the script so for the investor, if companies are being they have higher valuations? Is there more pressure on the on the entrepreneur? Excuse me, is there more? Is there more pressure on the entrepreneur to perform to reach milestones quicker to raise their next series quicker? Is it is it almost detrimental on the on the health of a company to

John 29:49

you know, venture investors, right? They, they they want companies to move as quickly as possible. They there they can’t necessarily wait 20 years for for them to be able to get returns, right? They want to get returns as soon as possible. And so there’s, there’s that dynamic. Another dynamic is VCs, you know, they want to see, they want to see their companies, frankly, get get marked up by other firms and subsequent rounds. And those can come into play at first, especially with newer firms, where maybe they’re trying to establish a track record. And so they’re not going to have a company exit, necessarily within two or three years. But if they can show that there’s been some markups of existing companies where they went on raising another round of the higher valuation, that’s a that’s a positive for that firm. And I think, specifically in this market, what we’re definitely seeing is more pre emptive financings where you’ll see a company maybe raise a seed round. And then six months later, they’ll raise a series, a opportunistically whereas Normally, you wouldn’t go out and raise in a six months after you raise your seed, you probably take that to eat a year or so and then go out and raise it. So I think that’s a good example of sort of the level of froth I guess, in the market.

Scott 31:12

And would you recommend, again, for entrepreneurs, you we mentioned before, how operators are moving into venture capital roles? Do you recommend that entrepreneurs find roles that prioritize operators on their team versus firms that don’t? I don’t know if that’s a fair question. Are firms exist that don’t have operators? I’m sure some do smaller ones. What’s your opinion on that observe

John 31:37

how to position yourself as an entrepreneur, if you’re looking to break into VC, there’s a couple of angles you can take. And you would have to sort that out based on the firm. So there’s some VC firms that very clearly, you look at the staff, it’s all former operators, right? So those are definitely firms that that would probably look at your background as an entrepreneur. And that would resonate to a certain degree with them, not a guarantee you would get a job or anything, but but that would be almost like table stakes, to even sort of get in the room with them. But I think there’s also an angle where, you know, I’ve seen firms where they actually, they they’re sort of lifetime investors, and we’re not operators, but they saw value to bring an entrepreneur in to basically round them out. Because you do. I don’t think there’s any world where that background is not valuable when it comes to investing like operating experience, I think it’s always, it always helped, it probably sometimes can create some challenges as well. But overall, it’s a net positive. So I think in those cases, with firms who maybe don’t have a strong operator to sort of position yourself as, as that you can sort of, maybe fill that gap. I don’t know if I’d say it as bluntly, but I think that might be more the angle that you’d want to take.

Scott 32:53

No, it’s fair. It’s it. Yeah, no, I that that was my I guess it was just wondering, like wondering where you should end up as an entrepreneur, what, where can you provide the most value, but also at the same time, where where’s the best environment for you? that’s also important. If you’re looking for career I was actually I was actually referring to as an entrepreneur trying to raise money, but also in the in the sense of looking for a career often that also makes sense to me. One thing, and I guess just I guess, to pick your brain on the on the current state of of investment. Explain to me something, and I’m trying to understand is I’m trying to wrap my head around it. So spax. So why are those more relevant? Now? I know they’ve been around for a while. What place do they have in venture capital? I know that chamath took, I guess it was social capital. He does Sofia holdings and they bought a 49% stake in Virgin Galactic. Bill Ackman raised a $4 billion back. These are all obviously, topical. Now. What place? Do they have? it? Are they going to be relevant long term? Are they just a fad? Are these things that people should care and learn about? Just curious

John 34:16

facts. I’ll admit I’m not an expert, but I’ll give you my quick take on it. And folks can can can run with it or not. With fact, that seems like it’s a really another vehicle for a company, its shareholders to experience an exit, right? So there’s, there’s back there’s obviously traditional IPOs direct listings, right? secondary sales, where you have companies just selling or people within companies selling shares on private market. So it’s another I guess, tool in the toolkit in terms of getting liquidity for employees or existing investors.

Scott 35:01

So they’re just another they’re not they’re another vehicle. It’s, it’s something that can be used. But in terms of, you know, your expertise, like if somebody is looking for a career these, these have no bear, these are just something else that you should understand as you start to venture into this world is something that could be an option that you may have to, you know, I guess, facilitate with an organization or a company you’re trying to take public. And because that’s obviously the end goal, I’m assuming through the various rounds, and then you have the end goal of actually IPO in or doing some sort of public listing.

John 35:30

Yeah, for VC, job seeker, if you will, you definitely want to understand facts. You want to understand what what sort of the major news around them in terms of our additions, factories only that are tied to certain high profile companies, but it’s probably not the thing you’re going to run into day to day as a VC is, if you were going to put like on the priority list of like, having great deal flow versus understanding the fact like, I understand this fact wouldn’t even be on the list, frankly.

Scott 36:04

Gotcha. Okay, gotcha. Fair enough. Okay, so that was pretty, I appreciate that. So we went, we went pretty deep on some advice for people looking to get into VC and venture capital careers. Is there any other points that you wanted to bring up? Because I wanted to, I want to just pull out some career lessons from you over your career, that will be good for our audience. But is there any other pointers tips for people that want to go into venture capital careers that we didn’t touch on? I didn’t, I wasn’t smart enough to ask you.

John 36:33

Let me know. happy to share one other thing that I think is super important when I actually think it really applies to all careers. But it’s particularly important in well networked industry like Vcn, and startup, which is going to your interviews, whether they’re formal or informal, over, eventually a cup of coffee, because we can actually spend time with people in person, again, now is really coming with a prepared mind about how you can help that person and like having a couple specific ideas in mind, and using the five legged stool framework to pop them out. There’s no reason that before you have that next interview, or that next coffee meeting, you couldn’t take 15 or 20 minutes to think about that person, that firm. And then look into your, your LinkedIn, your Rolodex, whatever you like to use to sort of track who you’re connected to, and come up with a couple of ideas for them. And I do this myself, I was meeting with the CEO of a company backed by NEA and benchmark, enterprise software company, and I was meeting with the CEO. And before I met with them, I went to their job page, and I saw who they were hiring. And then I went to him and say, Oh, I saw you’re hiring for this position. There’s someone I know who could be great, do you want to talk to them, right, and you’re not going to hit it every time in terms of having an idea or a good idea. But if you practice that, over the course of the hundreds or 1000s of meetings you’re going to have over your career, you’ll start to kind of build a muscle around it. And it’s just an opportunity to really add value immediately to someone and really make a great first impression, right VCs need a ton of people. And it’s hard to be someone who they remember and doing things like that can help them remember and be if you get back in touch with them, they’re more likely to remember whatever the thing is that you suggested or that you helped them with, or that connection you made. Very good,

Scott 38:51

good advice. And I think that is that that’s incredible, just general career advice. You made a good point that in in an industry that is as high network where they do see as many people as as they do, because that’s literally every single day is meetings with brand new people trying to pitch them on themselves and their product and their company, you have to show a little bit more, you have to bring a little bit more to the table to stand out. So that’s very, very good advice. Okay, so some lessons from your career. I want to understand just a few items because you’ve had success in building your community, your newsletter, your cohort. So as you built this out, what was the biggest challenge that you faced in building this out? And how did you overcome

John 39:37

it? Do you think in terms of in the venture capital space over the course of my career, these different programs, courses, the newsletter, etc, it’s really time. And how do you maximize your time so that you’re able to work on those things. You’re able to get a reasonable amount of rest, you’re able to spend time with your family. I’m married three kids. So that’s critically important to me. If you’re working full time somewhere, and you’re doing these other things, right, how do you balance at all. And so one of, I would say one of the best sort of career decisions I made, and this was going on, I want to say maybe seven years ago now is I hired a virtual assistant. And I had them helped me with everything from making appointments for me with the doctor to putting up content on my blog. And it really taught me that you can get an incredible amount of leverage if you’re willing to delegate even things that you might by default, say, Oh, I can just go do that myself. Like, oh, I can call the doctor myself, or Oh, I can, I can find a store that sells that thing myself, right? But actually delegating it, and being able to do that delegation in a way that is not dependent on time. And what I mean by that is, if on a Saturday, I remember that next week, I need to go and find a gluten free birthday cake, which is like a real thing that, like I’ve had to do, is being able to email someone say, hey, I need to find a gluten free birthday cake. And I need to be able to pick it up next week. And for them to go and do that legwork. And that’s kind of a personal example. And then on the side of the blog, for example, started within the last several years posting actual jobs, because the blog, originally just career advice, and then I started posting jobs, and I would not personally be able to post the 150 plus jobs that I posted on a blog every month without help, right? It just wouldn’t happen. And so being able to really scale that by first working with a virtual assistant, and now I work with a bunch of folks who are sort of part time work with me on that, versus a virtual assistant who just kind of doing all manner of of personal assisting and professional things. So that is one thing I would say is you know anyone who just to keep it simple, you know, if you’re making, say 100k or more a year, I would argue that you should have an assistant.

Scott 42:16

Yeah, very good advice. Very good advice. And actually, you know, that’s the number one thing that I think that people who are just starting to do their own thing that haven’t acclimated to, and really, really gotten used to hiring somebody to do these small little things that you think you can do, why can’t I do them myself, that’s silly, I’m not gonna pay somebody. But the second you do that, you realize the momentum of the thing you’re building, or the thing you’re doing just seems to take off. Like, it’s just, it’s incredible, because then you realize, like you said, You said it perfectly the leverage that you have very, very, very smart advice. And I do think that, you know, if you are making over 100k, there’s better things that you can do with your time. Regardless of whether or not you have a side hustle. But at the end of the day, I’m a big fan of building out your own personal brand, obviously. So I think that everybody should be focusing and trying to do that regardless, but I’m very, very smart.

John 43:12

And, okay, I wanted to throw one more thing, because I’m really passionate about this, this topic. And I don’t actually write or talk a lot about it just by virtue of I focus a lot on on VP stuff. But in terms of building, like, it may seem daunting to like, Oh, I got to go and like find this person and hire them. And then I have to figure out what to give them right, there’s like 567 steps, and you’re not even going to get the step two before you’re like, this seems like too much, I’m not going to do it, right. But you can really start to build that muscle by using task based virtual assistant services, or marketplaces. So Fiverr is one where you can hire someone to do a very simple task for you could be proofreading a document, and it could be some basic internet research. There’s one, I use Fiverr, there’s one I use called fancy hand, which is like kind of a funny name. But basically, it’s a task based virtual assistant service. I am going to be doing some travel soon. And so literally last night, I was pinging them with a bunch of requests, kind of researching the place we’re going and things we should do and where we speed and, and, and things like that. And it’s those are very low risk ways to like learn how to work with an assistant or someone who would have the same profile as an assistant. And just like standing there and like kind of building that muscle and you’ll have an aha moment when you do that. Like when you send someone a document to proofread and they find six things that you wouldn’t have found it and made your work better and made your blog post better. Maybe it made the thing you’re going to give your boss tomorrow better, right like I just there’s a lot of opportunity and I think venture bankable type opportunities in and around that space, not necessarily virtual assistant companies, but I think there’s a world where, again, there will be a lot of people who will have either dedicated or they’ll be leveraging some of these per task type of services to, to kind of give them superpowers, basically, to allow them to be more productive in their day job, or 10 times more productive in terms of whatever business they might be building. Yeah,

Scott 45:22

no, that’s good. I’ve never heard of fancy hands before I use Upwork. Myself, Fiverr. I’ve used a lot. I’m fancy. And I’m gonna have to check that out. That’s a new one. But the good, good advice. Okay, what would be one lesson that you could tell your younger self.

John 45:38

One lesson that I could tell my younger self, would be that there is no such thing as a once in a lifetime opportunity. So when I was younger, I would often see some kind of a job. And I say, Oh, that’s, that’s a once in a lifetime opportunity. And I think, if you are focused on your career, and kind of moving forward in it, you’ll you’ll kind of, I think, learn this lesson on your own. In that deal, you’ll start to realize that there’s no such thing, there’s just a lot of great opportunities, if you are able to sort of be in the right place at the right time, frankly, but also, in terms of just, you know, really trying to do sort of the best job that you can it sounds kind of trite, but it’s true. And, you know, I think those things, if you’re doing those things and catch a few lucky breaks, or meet sort of the right people along the way, that you’re going to see lots of things that seem like once in a lifetime opportunities, so kind of nullifying the whole once in a lifetime opportunity. Yeah. Very good.

Scott 46:47

What, who is one person that had a major impact on your life? And what was that impact? What did you learn from that person?

John 46:53

So the person that influenced me the most in terms of my career, and sort of how I approach work is my dad. So I remember growing up, my dad, my parents were divorced, my dad had a day job, but also, he did a lot of work. On the side, we did work on both, he actually did work at the daycare center, where I used to go to sort of defray the cost of the daycare as well. And I remember going with him, like to the daycare center on weekends for him to do that work. And I don’t know for sure, but I think that made a big impression on me, in terms of, you know, really, you know, kind of working hard. Providing, and, you know, I think that’s that really rub rubbed off on me for sure that that work ethic that he had, and still has, you know, he’s retired, but he’s still still working on boats and doing things like that. So yeah, I forgot. I have to say my dad. Good. All right. No, I

Scott 48:01

appreciate that. I appreciate the answer. And it is usually it always does default to a parent, or somebody close in the family. But it’s always interesting. Some of the some of the lessons and some of like the, you know, this, the things that parents taught us or grandparents taught us that they really had no idea they were teaching us at the time, it was just through like day to day actions that he sounds like an incredible person offsetting the cost of daycare by working there. That’s, that’s, that’s hard. That’s that’s the hard working man. Good, good. recommendation for the audience. For a book, a podcast, something that they should go check out. They can learn from the you obviously have enjoyed.

John 48:45

Yeah, in terms of book recommendation, marriage, there’s two books that I think are excellent. And one of them, I actually gift pretty frequently to folks and going vSphere just other people who work with me. So the first book is called million dollar consulting. And it’s by Alan Weiss. And he is a lifelong sort of solo practitioner management consultant. And he’s built a million dollar at this point is probably a lot more practice as a solo practitioner of consulting, which is pretty impressive. And the book is just, it’s a great tutorial and how to be a professional, how to sell and consultatively. It’s got some great stories in it. It’s an excellent book, highly recommend it. Good. And then there’s a marketing author, sort of Guru type and I mean, grew in a complimentary way. Not used that complimentary way. But but in this case it is, is there’s a J. Abraham, who has written a few books, and the book that I felt was, it’s been really it’s the book I actually go back to Constantly I gift it. And it has really unique perspective, like a lot of business books are kind of saying the same thing, in my opinion, for better or for worse. This is a book with a lot of unique ideas I’ve not seen anywhere else. And it’s called getting everything that you can with all that you got, I think that’s the title and have to go back on Amazon, it’s a bit of a mouthful of a title. But if you look up Jay Abraham on Amazon, you can find his book, it’s got a white cover black writing on it. And it’s, it’s great. And one of the things he really pushes in that book, he calls it the strategy of preeminence. And that is really a strategy where similar what I was talking about before, where you’re really trying to figure out, how do I add value to this person that I’m trying to work for, or this person that I want to partner with, or this person that I want to sell to? And really coming at it from a perspective of helping them in, in sort of thinking of them, as you know, as a as almost like a trusted friend, what would a friend do to really help this person move forward with whatever they’re trying to do? He’s got a lot of other interesting things around different revenue models, business models, and things like that, that are pretty creative and interesting. So yeah, that’s what I really like as well.

Scott 51:14

Those are two books that have never been brought up on the show. And I do I do know, the book million dollar consulting. I don’t, I don’t know the second one, I’m gonna have to look it up. I have to listen back and get that title and go pull it off Amazon. But no, this is a great recommendations. Thank you very much. I appreciate that. Because a lot of a lot of the books end up, you know, they end up being the same, but those are two brand new ones. I appreciate that a lot. Okay, last question. Before I get some socials and web from you. This is this is I guess, the most important question, in my opinion, what does success look like and mean to you?

John 51:55

To me, success means having as much control over your time, and how you spend it as possible. It’s it’s not about the money, per se, it’s really about on a given day, am I working on the things that I want to work on? And am I not working on the things that I don’t want to work on? Am I able to spend time with the people I want to spend time with I’m able to have a schedule where I can prioritize family over work, and things like that? I think, to me, that is what what success is? And I don’t think I’m I’m there yet, but I do certainly think that as someone who now is sort of early 40s. You know, I think I’m a lot further along than I was in my early 20s. So I guess I’m making progress.

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