Jacques Benkoski, General Partner at US Venture Partners, shares lessons from decades of experience as an operator, CEO, and VC. He challenges common startup myths and offers a framework for market entry that emphasizes strategy over luck. Jacques explains why focus—not speed—is the key to building category leadership, and why the venture ecosystem has become noisier, faster, and harder to navigate. He also opens up about the psychological toll of startup leadership and why founders need thought partners, not just capital.
Jacques Benkoski, General Partner at US Venture Partners, shares lessons from decades of experience as an operator, CEO, and VC. He challenges common startup myths and offers a framework for market entry that emphasizes strategy over luck. Jacques explains why focus—not speed—is the key to building category leadership, and why the venture ecosystem has become noisier, faster, and harder to navigate. He also opens up about the psychological toll of startup leadership and why founders need thought partners, not just capital.
In this episode, you’ll learn:
[01:00] From Belgium to Israel to Silicon Valley: Jacques’ global path into tech and AI
[05:20] “This time it’s different” is rarely true—how founders should think about hype cycles
[11:00] Why more capital doesn’t mean an easier path for founders
[13:30] The venture industry is now a volume business—but founders need depth, not scale
[15:00] What founders get wrong about market entry—and why randomness is the enemy
[17:30] Focused beats first: how Medigate won in cybersecurity by narrowing in on medical devices
[30:00] The importance of reflection, walking without your phone, and finding a mentor
[37:00] Jacques' nonprofit passion: creating dialogue between communities in conflict
The nonprofit organization Jacques is passionate about: Technion
About Jacques Benkoski
Jacques Benkoski is a General Partner at US Venture Partners (USVP), where he invests in enterprise software, AI, and cybersecurity startups. He has over 20 years of experience as a VC, following a successful career as a startup CEO and tech executive. Jacques is also the author of Market Entry Strategy, a hands-on guide for founders navigating early customer acquisition. A passionate advocate for founder wellbeing and long-term thinking, Jacques mentors entrepreneurs around the world.
About U.S. Venture Partners
U.S. Venture Partners (USVP) is a leading Silicon Valley venture capital firm with a strong focus on early-stage companies in enterprise software, cybersecurity, and healthcare. With more than $4 billion raised since its founding in 1981, USVP has backed over 500 companies including Box, Guidewire, Trusteer, and Medigate. The firm brings decades of operational expertise and deep sector insight to help founders scale with clarity and discipline.
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"The saying that I've used recently and that I think resonates with a lot of entrepreneurs is: your biggest danger is an inbound .
Because nobody can say, "oh, I got an inbound and I'm just gonna tell them no." And yet the likelihood that an inbound matches your focus area is very low. And so you ought to say no. But will you?" - Jacques Benkoski
[00:00:22] Gopi Rangan: You are listening to The Sure Shot Entrepreneur - a podcast for founders with ambitious ideas. Venture capital investors, and other early believers tell you relatable, insightful, and authentic stories to help you realize your vision. Welcome to The Sure Shot Entrepreneur. I'm your host, Gopi Rangan. I'm here with Jacques Benkoski. Jacques is a general partner at US Venture Partners (USVP). He's a very seasoned, experienced venture capital investor with more than 20 years of experience as a VC.
We're gonna talk to him about a few things. We'll definitely talk about his book Market Entry Strategy that helps founders on building their business when they go into new markets. We're also going to talk to Jacques about his perspectives and some advice on how to build successful startups, but first let's talk to him to find out who he is. Jacques, welcome to The Sure Shot Entrepreneur.
[00:01:29] Jacques Benkoski: Thank you. My pleasure to be here.
[00:01:32] Gopi Rangan: So you are from Belgium and you studied in Israel and then you also studied in the US and then you made Silicon Valley your home. Walk us through that journey.
Yeah, I think it's sort of a classical Silicon Valley immigrant story. So I was born in Belgium. The advantage of being born in Belgium is that Belgium is small and you speak a lot of languages before you graduate high school. And so you immediately think about a broader horizon and where else you could have an impact. I did study my undergrad degree in computer engineering in Israel at The Technion, usually called the MIT of Israel, w hich gave me an amazing education, and then from there I came to the US, studied a master's and a PhD at Carnegie Mellon.
For the people that don't know, AI was actually invented at Carnegie Mellon in the eighties. I had the privilege of having my first AI class with Professor Herbert A. Simon, who went on to get the Nobel Prize. So early days, but it turns out that most of the concepts that we know today existed back then, or were invented back then. We just have a heck a lot more compute power to do things that could not have been imagined then. But we were playing with natural language processing. We did chess playing algorithms. Those kind of things existed by then. And it's very fun to see how far along we've come.
And then from there, I decided to work in industry. I actually recommend to a lot of entrepreneurs to start by actually working in industry. It is extremely hard to acquire the knowledge of how a large company functions and if you ever want to sell to large enterprises, having that knowledge of how a company makes decision, how it decides what to buy, what the process of buying something is an incredibly invaluable foundational experience. And so I often get pinged by bright young people that come out of school and like, oh, I want to get into venture. And my answer to them is, go work. Go first get that experience, get that knowledge.
Even if you wanna be an entrepreneur, there's the myth of the drop off that made it, and for sure that happened a few times and makes for great headlines. I believe that the tried and true way to succeed is to actually build that foundation, start by understanding an industry, start by understanding how corporations function, and then my path was from there to join a friend that had started a startup; an incredibly successful company in the nineties. We went public. We were a public company for three years, and then we got acquired.
Another friend called me and he said, "yeah, by now you've become a business guy and I wanna start this company, and I need a CEO. Would you like to join and help me run the company?" I did. Went through the incredible end of the nineties with the.com and the crazy fundraising, which looks a heck a lot like what we're going through right now. The same, buildup, the same expectations that this market will be gigantic and then had to manage the crisis that happened in 2000, 2001.
At the end, the web happened. It just didn't happen in 1997/98. It happened in 2003, 2004. And so a word of caution as people go crazy about artificial intelligence, it will happen. It may just have to go through a longer and more painful process than the rosy picture that we all have in mind right now.
USVP was an investor in both the companies I was involved with, and so when I sold the second one, they asked me what I wanted to do. I never intended to be a venture capitalist. I'm still not sure I'm really a venture capitalist. I like to build companies, I like to help people to build companies. And USVP was an incredible platform from which I could do that with people that had decades of experience way beyond what I had as a CEO And before that, as an executive in a company. And so I, to the best of my ability, have tried last 15 years to combine everything I learned as an entrepreneur, as an executive with the knowledge that USVP carries as part of our institutional memory and tried to make something out of it.
I've co-invested with USVP on at least one transaction. There's a company called Task Human. We have for sure portfolio in both of our firms. But it's incredible to see your extensive journey over the years. You've seen a lot. You started as a global citizen quite early in your career, and you ventured into AI well before the world saw what it was all about. You have been a very successful entrepreneur, but the past 20 years you've been helping many founders build businesses.
You came into Silicon Valley during that.com boom, and now we're going through so many waves.
You've seen many cycles of innovation come through the venture capital ecosystem. I'm curious to hear your perspective on how things are different now. You've already hinted that there are some eerily similar trends and examples that you see today that are similar to what happened 15, 20 years ago.
I'm curious to understand your perspective. How are things different today in Silicon Valley and in venture capital compared to when it was the.com boom time?
[00:07:07] Jacques Benkoski: I think whenever you hear "this time it's different" is when you should be careful. In the late nineties when people had the notion that companies KPIs should be eyeballs was like, oh, but this time it's different, right? It's never different. The foundation of how societies function, how business functions have evolved in a very Darwinian way over centuries. And we are where we are not by coincidence.
I mean, I'm sure it could have evolved slightly differently, but it's the logical evolution of how our societies and our businesses have grown. And so whenever people say, this time it's all different I always put a word of caution, which I'm doing right now.
That's not to say that I'm not enthusiastic about the potential and the opportunities, but one should think about them the same way that the web was transformative to our societies. Can you imagine functioning without the web, right? The same way that cloud became transformative. And we forget that about a hundred years ago, most houses didn't have electricity. And so when people say, oh, there's an incredible acceleration of change, look around you, and everything that's electric basically didn't exist a hundred years ago. So, yes, it's incredible pace of innovation, but in a perspective of a longer term evolution.
With respect to Silicon Valley, I think what has changed pretty dramatically is the magnitude of the venture ecosystem, the incredible amounts of money that have become part of this. One statistics which I talk about in the book is when Crossing the Chasm was written (the foundational book to Go-To-Market for Startups), the total amount of venture capital invest in the year was about $1.5 billion. We're currently hovering above $600 billion, like literally 400 times more.
That creates a very different dynamic in terms of how one should think about go to market, how one builds and grows a company. The availability of capital creates acceleration but at the same time this incredible amount of capital creates a logical piling up of money that is essentially money fighting other people's money. And so, you could say, well, how come there's actually not more than that if we 400 times bigger? But it's because every time there is a company, maybe in the nineties there would have been one company. Now there are six companies and they each have huge budgets and they're spending a big part of those huge budgets just defeating each other.
In terms of the amount of capital that actually is applied to innovation, it has grown of course, but it hasn't grown 400 times. And so, the ecosystem as it is today is probably less efficient than it used to be. But it offers a higher potential to people that know how to build something and have an understanding of an opportunity and know how to execute on building a plan to capture that opportunity.
[00:10:29] Gopi Rangan: I see. In my own career, over the past like 15, 20 years, there's enormous amount of capital entering the venture capital ecosystem. Initially I felt good about it, but I'm also worried that there's probably too much capital now.
That means for founders, it's a good thing. It's capital available easily. And there are many other infrastructure resources available to founders. So it's a great time to be a founder today, much easier than it was 20 years ago. Would you say that it's harder to be an investor today than it was 20 years ago?
[00:11:00] Jacques Benkoski: I'll challenge what you said. It's certainly easier for entrepreneurs that are showing good progress to get incredible amount of capital. I don't think that makes the entrepreneur's job any easier. Like if everybody had less, we would be just as well; we are where we are. But one shouldn't think of this as there's so much capital that my life as an entrepreneur has gotten a lot easier than it was. If anything, it probably is harder because you are thrust in the spotlight much earlier in the expectation of your acceleration as such that the cost of failure or just, not great execution immediately takes you off the fastest growing company. And then for those, there's actually less capital than there ever was 'cause everybody powers in into the ones that seem to have traction.
To your question of is it easier to be a venture capitalist? No, for sure not. But I think also the venture capital, as people call it industry, has grown in such a way that very often the craft of venture capital, the ability to help build a company, the depth of experience and knowledge that one should have has been replaced with just volume. And so a lot of funds especially the larger ones, it is a volume business. Entrepreneurs should be aware of that. That when you are in the volume business, then you as an entrepreneur, you're just a small, small piece of the overall chessboard.
And whereas you are pouring all your life and all your energy and spending nights and weekends, sacrificing family doing all those things, you wanna have some sense that there's alignment between that and how important you are to the people that invest in you. Because otherwise you, may find that that asymmetry, if you want, would make you a very bitter person.
And there's no company in the world ever to have had a straight shoot to success. It always goes at some point through difficulties. Then you wanna know that you matter to the people that have backed you and that you will have both the financial support but also the operational and of course psychological support that you would want to have in those situations.
[00:13:39] Gopi Rangan: This is very interesting. You have a very nuanced perspective on where we are today. I agree with you that the market is expanded to include many different types of VCs but only a few of them are actually in the business of supporting founders to build businesses. The art of how to find these founders and how to support these founders is actually what venture capital is about.
I want to talk about market entry strategy. What you've just described is: there's more capital and sometimes capital has become a moat also for some companies and they just fight against each other. That is not success. There are more resources available, like access to cloud is a lot easier.
They don't have to build a whole server system, things like that, like 15, 20 years ago. So many other resources including tools like AI that are available today. There are more people interested in entrepreneurship, working at startups much, much more than it was 15, 20 years ago. But at the same time, there are a lot of new pressures on founders. The expectations on growth is tremendous, and all of that kind of comes down to this one thing, how to enter a new market, how to bring a new product into a market, and how to cross that chasm. Can we talk about that because that's what you specialize on. I see that the way it started was when you gave a lecture on this topic to a few founders.
You got a lot of emails, and then it turned into a seminar, which you have now provided many times over. And I've attended one of your seminars. It's incredibly insightful. Why is market entry strategy important?
[00:15:10] Jacques Benkoski: So let's go back to what we're talking about, the size of the venture capital available and the resource available in the fact that so many of those dollars are spent fighting one another.
If you look at the premise of Crossing the Chasm it was written in a world where large companies were afraid to work with startups, right? You had to find what was correctly termed an early adopter. Early adopters would be risk takers that would be willing to work with startups. And then having those initial customers and references, you could cross the chasm into the wider market at 400 times the size. And in an environment where every corporation has understood that unless they embrace innovation, one day or another, they will go the way of Blockbusters and Nokia and Kodak, right? Everybody in the corporate world knows those stories and they're trying, not always very successfully, but at least trying to embrace working with innovation.
And very often, this is something I learned in my very first job, one of the reasons large corporations work with startups is the impact that the startup has on their own organization, the change that they are struggling to bring about in the way they operate is accelerated by borrowing and partnering with a startup that has energy and new concepts.
Now because of the fact that there's so many more startups, so much more capital, and that corporations have been educated into the need to work with startups.
The question is no longer how do you find an early adopter, but why you? Why would you be the one that they would work with when there's probably 7, 8, 10, 20 different startups that at least on the cover would be going after the same market that you're going?
And so your ability to succeed as an entrepreneur, as a young startup is this initial entry market. It's the notion that you want to get to that first set of customers in a very disciplined way because if you're just shooting in every direction and you are, all of the competitors are shooting in every direction it's sort of a random game. And I guess being an engineer, I don't like randomness. I'd like to design it and get it right.
So the notion of the market entry strategy is really to mimic if you want the D-Day invasion of Normandy and to say if you are trying to penetrate a market, or if in that case you're trying to conquer Europe, you don't start by attacking every shore at the same time or some random shores based on whatever parameters. You're actually doing a thorough analysis of where you wanna land, and then you put all your forces on that single landing point. And once you have established that beachhead, once you're able to bring more resources to bear on that single entry point, you're more likely to succeed and you'll more likely to have a basis from which you can then expand and attack the rest of the market; which you will do when you grow up, but you should not try and do early, otherwise you'd be dispersing your forces in a way that, again, with that detail analogy is obvious. It would have made absolutely no sense to have multiple entry point because none of them would've succeeded.
The difficulty in market entry is to have the discipline to thoroughly analyze who your ideal customer profile might be. Why are you unique to them? And refine both what you do and who you pick such that you are unique to them, such that none of the other 17 companies that you compete with could claim the same benefits for those specific customers, and then you effectively, from day one, a leader in that tiny market you've decided to focus on.
The difficulty is obvious for an entrepreneur is you have to say no to so many things. And a lot of successful market entry is based on that focus. And once you found the initial entry market to just focus on it maniacally until you have enough heft that you can take on other opportunities.
The saying that I've used recently and that I think resonates with a lot of entrepreneurs is: your biggest danger is an inbound .
Because nobody can say, "oh, I got an inbound and I'm just gonna tell them no." And yet the likelihood that an inbound matches your focus area is very low. And so you ought to say no. But will you?
I was talking to an entrepreneur who has a great product great in-roads into a segment of the US market. And as we were talking about what they would do with the Series A that we might give them they were talking to me about opportunities in Europe. I'm like, "why would you do that?" They said, " Well, we have leads. We have people that want the product." I'm like, "okay, would you write a hire person in Europe or have one more person in the US? What would be the gains that you would get from having both?" That's the analysis that you want to make and not just say, Hey, I have an inbound. I can't say no. Yes you can. It's just hard to say No, I recognize that. But it's the key. And so, to summarize maybe the last few minutes is market entry matters much more than it used to because of the competitive nature brought about by 400 times more venture capital and willingness from all corporations to work with startups. Therefore, you need to really execute it better than ever in a way that is really thoughtful. And if you do it randomly you might hit the magic product market fit. Again, I'm not a big fan of randomness, so let's think about it. Let's architect it, let's do it and let's focus on it.
[00:21:27] Gopi Rangan: This is very wise. It's incredible. Thank you for sharing this, and thank you for synthesizing so pain that founders go through is because they don't understand the nuances of this. And thank you for synthesizing all of your years of experience into just a few minutes.
It is hard to find a target market. It's hard to research the target market. It's hard to identify the ideal customer profile in that space, it's hard to say no to inbound, and it's hard to focus on that one thing, that niche sector where you can dominate who has done this well and what did they do to get it right. Can you give some examples?
[00:22:02] Jacques Benkoski: Yes. there's one, example of one of my previous companies been sold, so, there's no more attempt at putting the spotlight on them. It's just a good example. It was a company that did cybersecurity for medical devices and it was born at the time that many companies used similar technologies to scan networks and find devices on those networks and be able to provide security for those devices.
At USVP, we decided not to participate in that market because the vast majority of those devices are worth single digit dollars. And so your ability to get paid significantly for protecting them is limited by the value that people assign to the device. Then came this company that said, we're gonna do that, but we can do that only for medical devices. First it captured our attention because medical devices are a lot more expensive than generic devices. And so when you have devices that costs hundreds, thousands, sometimes millions of dollars (think of an MRI machine), then the willingness to spend money to protect them is proportionate to the value of the device.
So that was the first aha moment. But the key element that's related to the question you asked was: because they decided to focus exclusively on medical devices. Even though at the beginning the technology was perhaps differentiated, but maybe not enough to create a successful inroad, they by construction, he most immediately became the leader of security for medical devices.
And in no time, and I really mean like one of the fastest ever I've been involved with, they gathered an understanding of the customer problem and therefore positioned themselves as a trusted vendor to that community and in single digit million dollars in revenue, started to do reference selling because within that smaller community, within that focus area, it was easy to get that word of mouth to function.
And so one hospital chief Information Security Officer would meet another hospital chief information security officer, and they were the undisputable leader. And so they would just say, "Hey, we're using this. You should use it too."
What that does is it completely changes the dynamic of your cost of sales. Instead of you chasing in every possible direction and staying up at night, wondering if somewhere there is an RSP for which you can answer across all sectors and across all geographies. Now you're saying in my target market. It is almost impossible that somebody would consider an RSP and not call me, because in that market I am known.
And so I go from chasing leads to the good kind of inbounds, the ones that match the focus market want. And literally, the efficiency of the company increases many times over in that customer acquisition because of that leadership that it acquires early. So this is perhaps a textbook example of how it worked, but I would challenge anybody that listens to this and says what would it be for me?
What sub-sector it would be for me? And just by the fact that you would focus on a sector even if you're not that different from your immediate competitor in that sector that you focus on, you're likely to win. And if you're likely to win and establish that beachhead, then you're that much stronger as a company to do more.
The power of focusing on specific target market, whichever way you define that narrow ring, creates that market leadership effect that then enables you to claim leadership and a better market entry.
[00:26:13] Gopi Rangan: Yeah. When they're razor focused, all the potential customers in that sector are now aware of the company without the company having done any significant marketing. And that word of mouth and the industry is now ready for a new solution. Instead of spreading themselves too thin into multiple areas and they're nice to have for a few people, but it's never a core important solution for anyone.
[00:26:39] Jacques Benkoski: I think the difficulty in doing so is human, right? I mean, as a CEO I did not do a good job at this, which is one of the reasons I wanna pass on that knowledge to others. I vividly remember an all hands meeting with somebody ask and say, "so what's our focus market?"
And my answer was, "no, we do it all." And I thought that was the right answer. It wasn't. Often it's easier to just say, I'll try a bunch of things and I'll find the one that works. And when you think of the amount of effort that you're gonna put, the years of sleepless nights and weekends and single out focus on your startup to leave that to chance, to leave that to randomness is ludicrous. So spend the time, do the effort really thinking this through. If you don't have the knowledge, then design what experiment you need to do to get the knowledge that will allow you to make that decision. And then ruthlessly, focused, but it's hard.
I, I have experienced people that have come to my seminar and have said. You are a hundred percent right. You're just asking a level of discipline that most people struggle to have.
[00:27:46] Gopi Rangan: It is difficult indeed. But sometimes founders don't know the market well enough, especially when they don't have domain experience or they haven't worked in that space. For example in the Medigate story, Jonathan Langer, Pini Pinhasov, and Itay Kirshenbaum didn't come from the medical devices market. They didn't have many years of selling into that space, especially in the us. How can founders learn the art of understanding the market, understanding the ICP and figuring out how to focus, raise, or focus on something specific.
How can they do that?
[00:28:20] Jacques Benkoski: I think you're right. Certainly we respect to Medigate team but you can have just a thought experiment and say, which markets would value this more than others? And there, medical device was not that hard of an answer to come up with. And you could say, well, I have three theories, right?
And this is one, two, and three. And then you go, okay, what do I need to know to rank one, two, and three? And then you really think it through and you say, okay, I need to know this and that and this. And let me actually go in a very systematic way, get the information that I need. And it may be by talking to customer, it may be by hiring somebody. It comes in many ways, but you're doing that in a very directed way as opposed to a random way. If instead of doing that Medigate had said, "well, let's try selling to anybody." And maybe one of those would've been a hospital. They probably would not have recognized the product market fit that they did. And so, I don't expect founders to always know, though it's very preferable that you have that intimacy with a specific market. And if you don't that you hire people that do but at least be thoughtful about it. Organize your experimenting in such a way that it is the most productive to answer the questions that you need and then go get the knowledge that you need to get.
[00:29:48] Gopi Rangan: Random is tempting. It's easy.
[00:29:51] Jacques Benkoski: And I think, in a number of markets, those that are way more consumer, right? Like, like what I'm talking about is B two E only. You don't have much more than random, right? And so, you might wanna do that.
A lot of the very fast accelerators, like a Y Combinator and the like, which have very short cycle of development. You can go random because you know the investment isn't that high and you can touch a lot of data points and maybe get an answer. But if you're developing a product that's gonna take you a year and a half to develop, man, I wish you think about who you're gonna develop it for before you develop it and not the other way around.
[00:30:30] Gopi Rangan: This is gold. I'm delighted to bring these stories out and share it with the founders in the future. I want to pause to ask you more about the psychological side, the ups and downs of the journey of the founder. That is also important, and you mentioned that earlier in the conversation.
What can founders do to manage themselves so that they can become the leaders and unleash potential both in the company and in themselves?
[00:30:56] Jacques Benkoski: I think the number one element that would bring is you need to have a person that is a partner, mentor that you can work through things that you can as often, not necessarily ask a question and hope for an answer, but in asking the question and forcing yourself to verbalize your concerns and your fear, find the answer in yourself, but you need to have that person to do that with.
When you go to a psychologist, the psychologist doesn't tell you what the answer is. The psychologists make you talk through until you come up with what the answer is, right? Somebody that was a VC for a bunch of years and decided to stop wrote a goodbye post. And he said, "if I had known back then what I know today, I would have gotten a degree in psychology and not an MBA". Because at the end, business building is all about people. And so the element of helping people is key. And that's where I think, I go back to experience and the kind of VC that we practice, where you have by construction, USVP is a GP only firm. Whoever you're gonna talk to is gonna be somebody that has that depth of experience and knowledge and has themselves been in your seat and, sort of asked themselves those questions. And one of my very big reasons for doing all this and writing the book is because some people have helped me so much that I have a moral duty to pass on some of knowledge they gave me. Some of the things I'm telling you came from them, right? I didn't come up with all this by myself. Some of it is inherited from those interactions.
Often we see teams of multiple founders. That works somewhat. It does create a bit of an echo chamber. 'cause you think you talking to somebody else but you're actually talking to somebody that is basically a mirror of yourself. And it does create a difficult dynamic because at the end there's only one CEO and you, the CEO talks to the founders and the founders are executives in the company.
It creates a difficult dynamic, right? I mean, those are people you don't necessarily always want to confide in two, including on things like, should you fire one of them, which is a question that will come up at times, right? And so find somebody like that. If it's one of your investors, I often play that role on the companies I'm investing in.
If it turns out that you don't have any affinity, which by the way is a problem, but if you don't have any affinity with any of your investors, then go find somebody. And it has to be somebody that has that depth of knowledge and has that availability to really hear you out, listen to you, and very often just hold a mirror and say, just like, like a psychologist would. "I just heard you say this. What do you mean by that?" That kind of simple thing and rephrasing.
I've had two mentors in my life and my last mentor that was on my board in my last company. I would go meet with him and I had gotten really good at this. I had come up with topics I wanna talk to him with about, and topics I didn't wanna talk to him about. And five minutes into every session I was talking about the things I didn't want to talk about, which is an incredible skill he had. And then I would leave his office thinking about how smart I was to have come up with all those solutions just by talking to him. That's the skill that you're looking for, the person that will play that role for you.
[00:34:41] Gopi Rangan: Often we have the answers within ourselves. But we need to go through that journey and hopefully someone holds the space for us to brainstorm and get the answers out.
[00:34:52] Jacques Benkoski: Yeah, and I think, having a plan, having the discipline, I go back to the market entry strategy, having a reference to compare against. Having constantly a 18 months horizon that you hold yourself to, which you might need to change, right? I'm not saying that plan is casting concrete, but creating that structure that I explained in the seminars and in the book, that lets you say, is this good or is this bad? Well, good or bad, versus what? And if you don't have a reference to say, is it good or bad, then it's sort of a moving thing. And the human brain isn't very good at maintaining perspective over time. Like you might find yourself saying, that something is absolutely a must have. And then three months later having forgotten that you said that to yourself and finding that you compromise and not have it right. And so having a reference plan to compare against is really important.
Often, certainly at the seed and series A, entrepreneurs fall into the trap of being busy, getting involved in all kinds of things that actually don't matter all that much, but creates busy work and don't take the time to take a distance from the day to day of the business, which again, those meetings with your mentor should do.
You need to take that time. And one of the recommendation I make and I didn't invent those recommendations is if you can or really try to. Every couple of weeks go walk in nature, go in the woods, go on the beach, no cell phone, no book, just by yourself, and just walk. And an incredible amount of clarity will come out of that from that distance. Let your brain sort of relax into its decision making.
A few months ago I was in a situation where I gave a term sheet to an entrepreneur and they got an acquisition offer and the entrepreneur was really struggling as to whether he should take my term sheet or let himself be acquired.
And I said, "I don't have any answer for you. Whatever I think is irrelevant, go on the beach, spend two hours just walking. You'll come back, you'll know when the answer is."
[00:37:06] Gopi Rangan: We're coming towards the end of our conversation, and I want to ask you about your community involvement. Is there a nonprofit organization you are passionate about?
Which one?
[00:37:15] Jacques Benkoski: There's a number of them. I certainly have been active for decades in my schools. The schools I went to. I am on the board of Technion and the other organizations are organizations that are around dialogue between communities, especially in the Middle East that are at war. Those are organization that attempt to say at the end we're humans and humans that know other humans can stop thinking of them as the enemy. At the end, for a better world and more peace in this world, people need to know each other. And whether it's some programs which allow kids of different backgrounds to study together, or entrepreneurs of different backgrounds to work together, or other ways to get communities to just get to know each other.
Pre-COVID at USVP, we used to organize a conference in Israel and I took on the challenge to bring one of my CEOs that was Syrian and remind you Syria is still actively at war with Israel. It was incredible to just see a human being talking to other human being and forgetting all the conflict and see what could be done.
[00:38:31] Gopi Rangan: Jacques, it was such a pleasure talking to you.
Thank you for sharing your personal journey, your specific examples and advice for founders. The wisdom that you have accumulated over the years from your mentors, from your direct experience with founders and from your investments. I really appreciate all the wisdom you've shared, and I look forward to sharing your nuggets of wisdom with the world.
[00:38:55] Jacques Benkoski: And if I may I'll put a plug for the book. It's called the Market Entry Strategy. You can find it on Amazon. There's a Kindle version too. It's all in there. And the reason I took the incredible pain, I didn't know how hard it would be to write a book, is because I wanna make it easier for people to have this as a reference.
For a while it was called a handbook or a guidebook. It's really a step by step that I would hope people keep on their desk and use as a guiding mechanism for their company. To be clear, I'm not making any money at this. So far I've actually lost a significant amount of money on it.
I'm not doing this for that. I really wanna see if we can create better companies and to the point you were making earlier avoid that many entrepreneurs and companies that are just a number in somebody's Chess board. We all humans we spend time and effort on this and let's try and make this a little bit better for everybody.
[00:39:53] Gopi Rangan: Thank you very much Jacques.
[00:39:56] Gopi Rangan: Thank you for listening to The Sure Shot Entrepreneur. I hope you enjoyed listening to real-life stories about early believers supporting ambitious entrepreneurs. Please subscribe to the podcast and post a review. Your comments will help other entrepreneurs find this podcast.
I look forward to catching you at the next episode.