The Exchanges

Q You have now arrived at your destination. Mark, thank you so much for coming on the show today. It's a great pleasure to have you on. And first a little bit about your background. What was the real reason for you entering into the venture capital world?

A Well, I've been a lifelong entrepreneur. Uh, it was never something I really chose as a career. It's always been a hobby and a passion. Uh, it started as early as elementary school where I was selling candy, uh, or baseball cards, candy in junior high and computers in high school to graduating seniors. Um, I tried to start five companies in college. The list goes on and on. And eventually through the course of my career, I fell into the venture game, uh, in an attempt to become a better entrepreneur. Uh, Learn a different side of the business, start to pattern match across companies, see what works, what doesn't, uh, and learn a lot of the pitfalls so I could avoid them myself. Uh, and then through that process, I just enjoyed it and have continued on with it.

AI assessment note: “I fell into the venture game, uh, in an attempt to become a better entrepreneur.”

Q And what did you learn? You said you started five companies. What did you learn from, I mean, how did they go? Firstly, how did they go?

A You know, when I first started out, this is back in college, quite a long time ago, uh, mixed, mixed, um, ideas. Some ideas were good, some were bad, but consistently terrible execution. And I think one of my biggest takeaways from that era was that there's a tremendous amount of knowledge required to be a successful entrepreneur. It is truly a mentorship sport. Uh, and if you don't have the right advisors around you, the right people to support you, you can, you can, you can fail for things that are very avoidable. Uh, the way I think about it is people like to say starting a company is like a marathon, uh, but it's a little different. In my perspective, it's not a marathon. It's And each step represents one simple, small, usually easy decision. The key is being able to make a pretty high, have a pretty high hit rate of making a good set of decisions against those small decisions. And if you do that consistently pretty well, if you're 80 or 90 or better percent of the time making the right choices, you will stay on the true course and build a great company. But it's, it's, it's an accumulation of very small trivial decisions that can take you off course Which if you have the right people around you, you can avoid.

AI assessment note: “Some ideas were good, some were bad, but consistently terrible execution.”

Q And finally, last question. Do you think there are any cases where, where startups shouldn't raise VC funds?

A Absolutely. So as I mentioned a minute ago, I wrote a book called The Fundraising Rules, which is a handbook for entrepreneurs to help them navigate the fundraising process. It's literally built in a chronological order of step by step, preparing for the meeting, what to do in the meeting, what to do after the meeting, and so on. The beginning of the book centers around Whether or not you should raise capital, uh, from venture guys or angels or otherwise. And I think it's one of the biggest mistakes people make, uh, in terms of destroying their return as an entrepreneur is if you ask an entrepreneur, you know, what's going to drive your value? They'll say, well, we've got to get the right team together, product market, all the generic stuff. Very few people talk about how they capitalize the company, not how much money they raise, but who they take it from. In my view, uh, The goal is to achieve alignment. You want to find investors that are interested in the economic opportunities, so looking at the cross-section of your market size, uh, and your barriers to understand kind of what the opportunity really is there for them, uh, and, or, and how much capital you require. But there are a lot of companies out there, founders who could build very small, successful businesses, uh, but take venture capital, uh, Uh, because thinking it's the only option, and basically destroy their re…

AI assessment note: “founders who could build very small, successful businesses, uh, but take venture capital”

Q And is that, is that literally cold calling them or cold emailing them if you?

A No, I think you can tweet at people, you meet people at events. I think it is okay to email them, but it's hard to get, uh, the meeting if you're just sending a cold email. But if you send, if you send in, hey, I came across this deal, I thought you'd want to look at it. You know, and the person says, you know, it's not for me, and you write back, right, you know, would you mind if I picked your brain a little bit on, on the career? You're not going to get a hundred percent conversion on that, but they might forward you to one of their colleagues. Um, that's a great way to play.

AI assessment note: “No, I think you can tweet at people, you meet people at events.”

Q And, and how did you get the right people around you? I'm assuming you did because you're very successful and done very well. So how did you, um, get the right network of connections around you to help mentor you?

A I think it's tenacity. People who are truly passionate about entrepreneurship, um, who love the process of creating, uh, tend to gravitate towards each other. Uh, and the, the entrepreneurial game, while it can be a role, emotional rollercoaster for a lot of folks is a very inspiring one. And so if it's something that's, that runs in your blood and, uh, and you really enjoy it, once you find yourself in one of these communities and talking to folks, uh, there's a lot of people who want to help. I think uniquely, uh, the startup community, unlike most of the other, uh, business worlds I have experienced, people benefit, are actually motivated and incentivized to help each other. Uh, in the startup world, we're not fighting over zero-sum games, like, you know, three companies chasing one client. We're creating new products, new businesses, so that competitive nature, while it's there, is less robust than more established industries where players are going head-to-head. It's much more dynamic of building something new, expanding the markets, expanding the opportunities, and so the culture and the nature of it is a lot more supportive and helpful.

AI assessment note: “People who are truly passionate about entrepreneurship... tend to gravitate towards each other.”

Q And for potential startup founders, how would you recommend that they could increase their network or, or gain a mentor that they've been wanting to gain? Would you recommend reaching out to them, um, out of the blue or would you recommend kind of building connections from your inner network?

A There's a couple answers to this. First is I think getting out there and going to networking events. If you're, if your community is a robust, uh, startup ecosystem, you get out, you go to events, you'll meet people. Um, I think obviously attracting interesting investors can help you. Uh, not all, but a lot of investors have a lot of operational experience, and the folks who have started and managed companies can provide tremendous insight. I think, uh, the way to hack all of it, if you don't have either of those available to you, is to surround yourself by Tier A service providers. There are a tremendous number of service providers in the market, Uh, and I'll talk to you about something I've actually done to this end to enable this. Uh, but a lot of them actually, you know, they don't really understand startups. You might, you might need insurance, and you can get insurance from the guy who sells insurance, but he's never been around a startup. He usually works with law firms or different types of businesses, and he doesn't have the wisdom or knowledge to really be a useful advisor. Uh, but there are, there's traditionally been a dearth of folks out there who go into the services space, uh, With the goal of not just providing a great service and the, you know, delivering the underlying ask, but also becoming advisors. There hasn't been much of that. So one of the things we've …

AI assessment note: “First is I think getting out there and going to networking events.”

Q And for potential startup founders, how would you recommend that they could increase their network or, or gain a mentor that they've been wanting to gain? Would you recommend reaching out to them, um, out of the blue or would you recommend kind of building connections from your inner network?

A There's a couple answers to this. First is I think getting out there and going to networking events. If you're, if your community is a robust, uh, startup ecosystem, you get out, you go to events, you'll meet people. Um, I think obviously attracting interesting investors can help you. Uh, not all, but a lot of investors have a lot of operational experience, and the folks who have started and managed companies can provide tremendous insight. I think, uh, the way to hack all of it, if you don't have either of those available to you, is to surround yourself by Tier A service providers. There are a tremendous number of service providers in the market, Uh, and I'll talk to you about something I've actually done to this end to enable this. Uh, but a lot of them actually, you know, they don't really understand startups. You might, you might need insurance, and you can get insurance from the guy who sells insurance, but he's never been around a startup. He usually works with law firms or different types of businesses, and he doesn't have the wisdom or knowledge to really be a useful advisor. Uh, but there are, there's traditionally been a dearth of folks out there who go into the services space, uh, With the goal of not just providing a great service and the, you know, delivering the underlying ask, but also becoming advisors. There hasn't been much of that. So one of the things we've …

AI assessment note: “First is I think getting out there and going to networking events.”

Q And, and how did you get the right people around you? I'm assuming you did because you're very successful and done very well. So how did you, um, get the right network of connections around you to help mentor you?

A I think it's tenacity. People who are truly passionate about entrepreneurship, um, who love the process of creating, uh, tend to gravitate towards each other. Uh, and the, the entrepreneurial game, while it can be a role, emotional rollercoaster for a lot of folks is a very inspiring one. And so if it's something that's, that runs in your blood and, uh, and you really enjoy it, once you find yourself in one of these communities and talking to folks, uh, there's a lot of people who want to help. I think uniquely, uh, the startup community, unlike most of the other, uh, business worlds I have experienced, people benefit, are actually motivated and incentivized to help each other. Uh, in the startup world, we're not fighting over zero-sum games, like, you know, three companies chasing one client. We're creating new products, new businesses, so that competitive nature, while it's there, is less robust than more established industries where players are going head-to-head. It's much more dynamic of building something new, expanding the markets, expanding the opportunities, and so the culture and the nature of it is a lot more supportive and helpful.

AI assessment note: “People who are truly passionate about entrepreneurship, um, who love the process of creating, uh, tend to gravitate towards each other.”