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Ep 289 Investing Beyond the Pitch & Building Great Companies with Alex Chompff

The Silicon Valley Podcast · 2026-06-28 · 39 min

0:00--:--

Key moments - from our scoring

Substance score

41 / 100

Five dimensions, 20 points each

Insight Density9 / 20
Originality8 / 20
Guest Caliber9 / 20
Specificity & Evidence8 / 20
Conversational Craft7 / 20

Alex Chompff shares insights from three decades of entrepreneurial and investment experience, starting with his family business background and progressing through angel investing in Sacramento to fund management operations. He emphasizes the critical importance of entrepreneurial DNA - the early exposure to business that makes startup thinking second nature - and explains how this foundation shaped his career trajectory. For founders seeking angel investment, Chompff stresses alignment over thesis: most angel investors don't operate from formal investment theses but rather seek community impact and alignment with founder vision. He introduces Ernesto Ceroli's enterprise facilitation framework as a model for understanding how entrepreneurship is learned and transmitted. The conversation pivots to fund operations and the structural challenges emerging managers face, revealing that a $10 million fund generating 2% management fees yields insufficient capital to cover team, due diligence, and portfolio support in years one through four. Evolution Ventures Fund Management helps emerging general partners navigate this gap, though Chompff notes that successful venture returns often materialize only in years 9-14 - well into a typical 10-year fund lifecycle. B2B operators, startup founders, and aspiring fund managers benefit most from understanding how to cultivate investor relationships through information sharing and expectations management.

Key takeaways

  • →Angel investors use personal capital and invest based on alignment and community impact rather than formal theses, unlike VCs who must deploy limited partner capital on schedule.
  • →Early-stage investment success depends on portfolio diversification - aim for 20-50 companies rather than attempting to pick individual winners, as most early investments trend to zero.
  • →Fund management requires significant upfront operational costs (legal, regulatory, staffing, deal sourcing) that management fees alone don't cover for emerging managers in years 1-4, creating structural pressure.
  • →The power imbalance between entrepreneurs and VCs is often misunderstood; GPs face their own constraints around limited partner management, carry realization timelines, and survival pressure.
  • →Entrepreneurial DNA - early exposure to business through family or mentors - makes startup thinking native, though it's beneficial rather than essential for success.

Guests

Alex Chompff

Topics in this episode

Angel investingPortfolio diversificationDeal sourcingSacramento AngelsVenture capital fund operationsManagement fees and fund structureEnterprise facilitation (Ernesto Ceroli)Emerging general partnersLimited partnersArtificial intelligence for due diligence

Questions this episode answers

How should a founder approach finding and aligning with angel investors in their community?

Understand that most angel investors lack formal theses and are motivated by alignment, community impact, and supporting smart entrepreneurs. Research their North Star (through blogs, prior work, or connections), orient your pitch accordingly, and prioritize finding investors whose values align with your mission rather than chasing generic venture-style investors.

What's the most common mistake first-time angel investors make?

Failing to diversify their portfolio. Most early-stage investments trend toward zero, so angels need to spread capital across 20-50 companies rather than trying to pick individual winners; the math requires this diversification for returns to work out.

Why don't management fees cover operating costs for emerging venture funds?

A $10 million fund at 2% management fees generates only $200,000 annually, but typically the capital is drawn in chunks over several years - meaning $50,000 in year one - while teams must be hired, deals sourced, and portfolio companies supported from day one, forcing emerging managers to subsidize operations from other sources.

When do venture capital funds typically see their best returns?

Returns typically begin in year 5-6 but the largest wins materialize in years 9-14, which creates tension since most VC funds have 10-year lifespans and fund managers must decide whether to liquidate or hold for the best opportunities.

What's the key to maintaining a good relationship with your investors?

Information sharing and clear expectation setting. Whether fundraising as a founder or managing a fund as a GP, regular communication about progress, challenges, and outlook is more important than the initial pitch.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

9 / 20

There are legitimate frameworks here - diversification math for angels, VC fund cashflow timing, and the mismatch between 10-year fund life and years-9-14 return window - but they're buried in extended personal rambling, repeated analogies, and generic encouragement. The ideas-per-minute ratio is low relative to the episode length.

if you've got a hundred thousand dollars to invest, try to get 10 at 10. 10 companies at 10,000 each. Better yet, get 20 at 5,000 each.
your big returns are going to be in like years 9 through 14 mathematically. And most VC funds are only 10 years long.

Originality

8 / 20

The 'technology decomposes monolithic industries' investment thesis and the reversal of the fundraising panning-for-gold metaphor are genuinely interesting framings, but the bulk of the episode recycles standard angel-vs-VC 101, the wedding analogy, and blockchain commentary that is neither contrarian nor fresh.

Technology decomposes monolithic industries.
the entire ecosystem of the fundraising world, the whole milieu, is actually panning for you. You're the goal in the ecosystem, not us.

Guest Caliber

9 / 20

Alex is a genuine practitioner - angel investor, fund manager, Sacramento Angels member - with real operational history, but he is a regional-tier operator with no disclosed track record, exits, or scale that would mark him as an exceptional voice. He speaks with credibility but not rare authority.

I started a network services firm with the help of my family's business that, uh, later transmogrified my life into a technology director for a large VC firm.
we invest alongside of the Sacramento Angels, we invest alongside of Y Combinator or we invest alongside of techstar.

Specificity & Evidence

8 / 20

The cross-border Mexico-US blockchain investment with the concrete 'two weeks to one-to-two hours' clearing time improvement is the episode's best specific data point, and the $10M fund fee arithmetic is useful illustration, but there are no fund returns, portfolio company names, or hard performance numbers anywhere in the episode.

a company last quarter that specializes particularly in cross border transactions between Mexico and the United States... small businesses and medium sized businesses operating in that space can wait as long as two weeks to have their transactions cleared
take that two week transaction clearing period and turn it into a one to two hour transaction

Conversational Craft

7 / 20

The host asks broad, generic questions ('what's the most misunderstood aspect,' 'what's one piece of advice') and never pushes back on any claim, follows up on any specific number, or creates productive friction. The conversation is friendly and meandering rather than probing.

Can you talk a little bit more about that? I mean thinking right now, I'm not sure if we really on in the 280plus episodes of the show really talked about the operations in the back of a fund
Should a founder really just think about, okay, if I do a friends and family round, how do I make this company break even a profitable from this money? Or should they be thinking about what's beyond that round?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A87%
  • Speaker B13%

Most-used words

money36invest22angel20first19angels18investors17capital16fund15venture14important14entrepreneurs11back11help11typically11community11understand11

Episode notes

Investing Beyond the Pitch & Building Great Companies with Alex Chompff What separates legendary venture capital firms from everyone else? How do experienced angel investors identify startups with the greatest potential before everyone else sees it? In this episode, we sit down with Alex Chompff, an accomplished entrepreneur, angel investor, and venture capital executive whose career has included working alongside some of Silicon Valley's most influential investment firms, including Kleiner Perkins, Mayfield, Sequoia Capital, and the Barksdale Group. Alex has also played an active role in California's innovation ecosystem through startup mentoring, angel investing with Sacramento Angels, and advising emerging technology companies. Drawing from decades of experience evaluating entrepreneurs, funding innovation, and navigating rapidly changing markets - including the evolution of cryptocurrency and emerging technologies - Alex shares practical insights for founders, investors, and anyone interested in building successful businesses.

Full transcript

39 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: You're listening to the Silicon Valley Podcast.

Speaker B: Welcome to the Silicon Valley Podcast with your host, Sean Flynn, who interviews famous entrepreneurs, venture capitalists and leaders in tech. Learn their secrets and see tomorrow's world today. Alex, uh, I'm super excited for this week's episode of the Silicon Valley Podcast. Now, before we dive into the challenging questions that I'm sure are going to be a breeze for you, you give our audience a little bit of background

Speaker A: of your career up to this point. Sure. Let me start by saying thank you for inviting me to be here. It's an honor and I appreciate the opportunity to share lifetime to date learnings. Don't ask me again in 10 years, I'll know more. I got here in a very normal way. I'm a native Californian. I the child of immigrants. I'm lucky enough to have grown up in the Bay Area, lucky enough to have grown up in an entrepreneurial family with a father patented product in the mid-80s as an engineer. And so I got the opportunity to pack widgets at the kitchen table along with my sister, and that's that business is still alive. It was a really good foundation. My real entrepreneurial life begins with my clipper routes. I, I had a morning paper route and an afternoon paper route. Sometimes I had both. It's very, uh. The funny thing is I was a much better paper delivery kid than paper money collector. But I did learn a really super good trick, which is to collect on, um, super bowl, because everybody's home on super bowl, and back then kids had to go door to collect their money for their paper route. And the tips are excellent on Super Bowl Sunday. Let's see. Yeah, that was, that would be the start. From there I learned how to play with computers. I was a CompuServe kid. And that turned into a job as a data analyst for a Japanese firm in San Francisco in 1990. And then from there I went into the military. And when I came home, it was 95 and I was in the Bay Area. I knew how to work with a computer and I had just met my wife and I needed the U.S. uh, and pay, pay rent. We had things I had to do. I started a network services firm with the help of my family's business that, uh, later transmogrified my life into a technology director for a large VC firm. And my wife and I decided to go and have kids after that. So we have five kids. And then after the kids were old enough, she said I could go play again. So here I find myself. That's my story.

Speaker B: I'm, um, curious to find out about that large VC firm. But even before that, how important do you think it is to be involved as an entrepreneur very early on in one's life? I mean, putting together widgets at the kitchen table with your father. How did that set you up later for the startup ecosystem?

Speaker A: That's a really good question. Have you ever heard of Ernesto Ceroli?

Speaker B: No. Please share.

Speaker A: Ernesto is a wonderful gentleman who lives in Sacramento, and he and his wife have dedicated their lives to creating what's, uh, called an enterprise facilitation process, or creating startups, which is credited with working with NGOs and governments around the world. Created many thousands and thousands of small businesses. And these are not like venture capital type businesses. These are rural, urban, agriculture, fit the world kind of businesses. And one of the questions that Ernesto asks when you get to know him is, what's your entrepreneurial DNA? What's your entrepreneurial DNA? And it's interesting when you're sitting with a class of entrepreneurs, I've taken this master class. It's very good. When you're sitting with a class of entrepreneurs. We all can remember how we got here. There's somebody in our lives typically who inspired us because it's not like capitalism was given to us from on high. It's something we invented.

Speaker B: Right.

Speaker A: It's a tool. And so it helps to be introduced to that tool at a very young age. I think then just like any other tool, its use becomes native. And if you're a digital native, life on the Internet is easier. Right? If you're an entrepreneurial native, life in startups makes a little more sense. Uh, I think it helps. I don't think it's essential, but I think it helps. Lots of people cross over into that world without much experience. But I bet if you ask them, there's probably someone in their background that they can remember who inspired.

Speaker B: And then through that journey, you'd mentioned that your wife said you could go out and play again. What, uh, does that mean exactly, this life?

Speaker A: Because I am an entrepreneur. First good fortune to be an investor as I get to the later part of my career. But I'm still an entrepreneur. I'm always trying to create things. I'm always trying to figure things out and build things. It's just that instead of watching my own businesses these days, typically I push them away. People have more time and more focus. Haven't made as many commitments in life as I have made. Can get busy on, uh, whatever they think is interesting. So my wife and I Have been married for about 30 years now and we just celebrated our 29th anniversary. It gets a lot. For any of your entrepreneurs who may happen to have a significant other in their lives, I recommend being appreciative and saying thank you and making breakfast and dinner dishes. Those are all things I recommend.

Speaker B: I think you just won over half the audience.

Speaker A: Those of you that are not yet, that's fine. We'll see.

Speaker B: But Alex, you went on to start or tell us about your involvement with the angel community in Sacramento.

Speaker A: Again, a good piece of luck. A good piece of luck. So angel investing, this kind of phenomenon, um, around the dot com boom, um, and, and subsequently after. Because there were a lot of people who in a concentrated area found themselves having created wealth and in many cases wanted to give back, wanted to contribute, wanted to sure grow their wealth. But I think in the early days it was at least as much about helping the community. And most of the angels that I know today, if they're going to get a return, they're going to get a return in the 8, 10, 12, 15 year time frame. So you got to find a way to get paid back in the meantime. And that has to be by knowing that you're doing good in the community and, uh, understanding that you're helping other people to be successful. And of course not everything's going to work out, but you can do a lot to help. In my experience, that's what the angel community in Sacramento is like. It's filled with people who are very giving. There are some standout examples. Martin in his group, stand out as an example. If you know that community. Jack Crawford, Impact Venture Capital A big giver. Moneta, all big givers in the community. And all those guys, I'm sure, started off as angels. And the Sacramento Angels, of which I'm very pleased to be a member, many years now filled with men and women that typically have enjoyed entrepreneurial success. That's usually how, uh, they come to be there. Some of them are highly compensated professional executives from past lives. But what joins everybody together is this desire to be active in the community and to support smart people and to create industry and to build new things. And so people are taking their personal capital and putting it to work. And that's by the way for your audience. Depending on their level of experience, Sometimes people get confused. They think angels write small checks and VCs write big checks. And really that can be true, but it's not always true. Angels use their own money. VCs use other people's money to make investments. Right and that's my experience with the angel.

Speaker B: It's crazy some of the times that

Speaker A: as an investment banker I'll pitch some

Speaker B: companies to family offices or high net worth individuals and just the size of checks that some people write dwarf some of the VCs. It's pretty interesting.

Speaker A: Just the wealth that some people have

Speaker B: been able to, uh, accrue over the years. Going back to the angel network, just in general on an individual level, how does an angel first decide what their investment thesis is? How does an angel, and I'm thinking of it from the perspective of, uh, you have a founder who just arrived in Sacramento and is looking to connect with investors but isn't sure the questions to ask. How do they go about asking angels the right questions to find out where that investor is interested in putting their money?

Speaker A: Okay, in this case we're talking about probably a really early stage entrepreneur without a lot of experience. Yes. Okay. So the first thing I'm going to say is you're so glad that you're getting started in 2026 because it used to be that you had to pound the pavement to find an investor and ask a thousand questions. And about the thousand and one question, they had to go do something else. Now you can go to artificial intelligence and get 90, 95% of your questions answered and your critiques given. You can really get almost all the way to the goal line. And then when you're talking to an angel investor, the most important thing to understand is that an angel investor is investing their own money. And their consequence of failure to invest is typically zero. So for a venture, a venture capitalist has to invest money. They don't invest money on a certain schedule. Then they're going to fall behind their plan and they can't, they don't really want to fall behind their plan. They have a structure. There's a lot of work and a lot of math involved in figuring out how, uh, to build a successful portfolio. And some variation is fine. But one of the most important rules is invest in companies. If you don't invest, you're never going to win. Where an angel can fail to invest and have no consequence because that money goes to a vacation, for example, that money buys a car. That money is, uh, uh, a down payment on an investment property. There are many choices for angels. There are uh, many selections. So recognizing that, recognize that angels invest because they're aligned, angels invest because they're aligned. So when you get into your angel community, you have your angel conversation, take a moment to find out where your angel's North Star is, if you can figure it out in advance, because you're lucky enough that they have a blog or that you talk about their work or you know them, whatever, think for a moment about where their North Star is. And when you understand where their North Star is, orient your boat accordingly and then go have a conversation with and in my experience, advanced angels. Let me save angels with a lot of experience and a lot of exposure, like the Sacramento Angels that we referenced earlier. And there are many angel groups around the country. They may have a thesis, they may have a structure, they may have a pattern of plan that they're working to. But the majority of angel investors that I've dealt with in my career are, uh, don't, don't really have a plan, don't really have a thesis, may or may not have an area of interest based on their prior profession or expertise, but are often more motivated by the desire to, like I said, give back to the kingdom, create something worthwhile, support local entrepreneurs. And also, I think it's important to understand just by the way, when we talk about angel investors, there's an implication that later on you're going to go deal with professional investors like venture capital investors and vast mhm. Majority of businesses that come online and are successful over the long term will never receive venture capital. They're not venture capital eligible. They're not the kinds of companies that venture capital firms look for. They may still have friends and family invest in them and they may still provide a very handsome return to those friends and family. They're just not a venture capital business. So when we're talking about angels in this context, it's often assumed that we're also talking about that rare slice of companies that's going to go on to further subsequent professional investment. More generally, I'd like to say find alignment with your friends and family investors, your angel investors. Those are the people that are coming into your company in the beginning. The other thing is that I often compare fundraising to a wedding in the sense that your wedding occupies all of your thoughts. As you're getting ready to get married, the wedding date approaches and what are you going to do and who's going to be there? There's so many things to think about, and it's not until you've been married for a little while that you realize how quickly the wedding is in the rearview mirror. Now you're married. Married is an entirely different proposition. And if you accept somebody's money, you are married. So it's very important to recognize and honor that relationship right Even if it's married in business. And um, honoring that relationship will go a long way toward cultivating you, um, will, which you'll probably need because your business is statistically unlikely to succeed. And it's always a good idea to maintain good relations and probably the best way to do that is through information sharing, be in communication with your investors.

Speaker B: Speaking of information sharing, what do you think is the most misunderstood aspect of startup invest in that first time angels or first time fund managers get wrong?

Speaker A: Pretty big difference between first time angels and first time fund managers. Typically first time fund managers are long time angels. So let's separate them. Probably the biggest mistake that you see for as a first time or early angel investor is um, not understanding that the math requires diversification. It's very difficult for most normal people to have access to high quality deal flow on a regular basis. And high quality deal flow is essential in order to diversify your investments because statistically most of your investments are going to trend to zero. And that means that the remaining investments that succeed need to be so tall that they can overcome all of their cousins going to zero. And so in order to get there you really need to diversify because the math is very clear, the data is very clear. It's very difficult to choose winners. Very difficult to choose winners. And that's because the things that will kill an early stage company are legion. And so many of them have nothing to do with the technology or the fingers, quality or any anything else that you can conceivably observe. There's an interesting idea which is that the earlier you invest, the more perfect the information can be. And that's because of information scarcity, right? The number of unknowns is always infinite, but the number of knowable things is finite. And the earlier you are in company, in truth, you can sit down with a startup founder in a couple of hours, know everything there is to know about the company. If you're at an early enough stage to go sit down with IBM and see if you can figure it out in a couple of hours, right? It's still a finite number of things. There's just too many for any human to go through. AI, uh, again being very helpful here for a lot of this. So that's the biggest mistake I would say for the first stage angel investors not understanding that you had better diversify. So if you've got a hundred thousand dollars to invest, try to get 10 at 10. 10 companies at 10,000 each. Better yet, get 20 at 5,000 each. Okay. There's kind of a magic number you hit 20 and then you've probably got a winner. All things being equal, you hit 50 and you might have a real total 10. So think about how much you have to invest and recognize that the return on your investment is probably a decade or more away and plan accordingly. That'll help. First time at Evolution, we have a program called Evolution Ventures Fund Management where we help emerging manage to emerge, we help them to get started, we help them to launch. And typically what we find over there

Speaker B: is that managers of uh, angel groups, managers of funds, managers of

Speaker A: professional fund managers. Evolution Ventures Fund Management is our firm that runs our funds. And those funds are run for groups of individuals typically called limited partners and so forth. Right. Limited partners very often align around a common idea or a common theme. Could be geographic, could be topical, could be regional, could be demographic. A lot of things to align around. And then there's typically someone in there who's what's called an emerging general or an emerging manager. And emerging managers need a lot of things to be successful. One of them is uh, knowledge, as you point out. And probably the most common in a missing bit of knowledge is the amount of actual work that's involved in running a firm profession. There, there's quite a bit going on. And fundraising is counterparts. The counterparty, right entrepreneurs fundraise. But we invest. It's the same thing for us. We're getting to a wedding and a marriage as well. We are going to be writing, working, riding along and working with you as advisors and possibly board members for years and years and doing that at a professional level in a way that's useful and meaningful and actually genuinely helpful as opposed to impeding. It takes a lot of work, takes a lot of effort. And that conversation is very often not something that emerging general partners have thought about. The other thing emerging general partners haven't necessarily thought about is the work that's involved in cultivating and maintaining your limited partner base. Because now you don't just have. Remember I told you earlier, the key to a good relationship is good information sharing. Right? Expectation setting VCs are investing other people's money, unlike um, angels who are investing their own money. When you're investing other people's money, we're just like you guys. We have our own investors and we have to keep them, keep them satisfied. And doing so is as much art as science. It's important to um, have team around you and have many different kinds of skills, from the analytical to the social to succeed in this work. And that's often overlooked by people who are let's say good at raising money or good at finding deals or particularly skilled from a technical perspective.

Speaker B: Can you talk a little bit more about that? I mean thinking right now, I'm not sure if we really on in the 280plus episodes of the show really talked about the operations in the back of a fund and just how time allotment for management, the back office, K1, all that stuff. I think we've really, I'm really trying to think if we've ever dive deep into that in any episode. So if there's any information you could share, I think that'd be pretty interesting.

Speaker A: I, I, they do call me Captain Spreadsheet. I think they mean it in a nice way. Yeah, it was a friend of mine my years ago Captain Spreadsheet. There, there is when you think about how to run this business. I'll uh, I'll talk about the business m model for a minute. The business model of a venture capital firm is a money losing proposition for a number of years before it might become a money g a winning proposition, a money gaining proposition. And that's because any other business, it's worth less than nothing when it starts, goes to the valley of dinner, takes in investors, it has back, it has back end costs, it has all kinds of things that have to be put into place initially from the legal to the regulatory to staffing, presence, brand, all these things that we put in place before you can do anything. And you uh, have to pay for very smart people who work for extended periods of time, working with other really smart people to try to find the good deals that are out there. So you have to create, you have to have access to deal flow and then within the access to deal flow you have to identify the deals that are worthwhile and on thesis and all the rest of it. And paying for that help, that expertise costs uh, a significant amount over many years. You think to yourself, okay, maybe I'm an emerging manager with a $10 million fund. $10 million fund, uh, 2%, that's what's that? $200,000 a year to manage. That's not bad. $200,000 a year maybe pays for me and somebody else or pays for a couple people and I pay for myself or whatever it is. You can probably work that out. But what you might be missing is that over a traditional fund you're not going to be managing all that money up front. You're going to be managing that money in chunks. You might only manage a quarter of it in your first year, half of it by your Second year and so forth and so on. So now you're talking about a $50,000 fees to start your first year's work with. And you're already in the hole and you got all these people you got to take care of and you need to go out and be a good member of your community, good steward of the resources that have been entrusted to you. Right? You're an organ of society. You need to behave like one. So doing all of those things takes a certain amount of money and management fees, particularly for emerging managers, don't cover. So that comes out of the manager's pocket or management companies, uh, pocket. So you have to set up another firm and have a different set of investors. And then if you are going to be successful, typically you're going to find that your returns start in year five, maybe year six. Your big returns are going to be in like years 9 through 14 mathematically. And most VC funds are only 10 years long. Okay, so now you're going to think about how do I carry over that value in year 9? I could cash everybody out, but. But if we hold on to year 13, we got a winner. Because the number one indicator for success is survival. You don't survive, you can't succeed. The longer they survive, the more likely they are to succeed. The more likely they are to succeed over a longer period, the better. Your opportunity is for a really tall tent pole. So how do you manage these costs that are upfront and can go for half a decade while being a good steward and taking care of your work and doing what you're supposed to be doing and cultivating the companies that you're hiring into or buying into. And then when those companies do start to come home, of course you need to take care of them. People take care of you all these years and you may be surprised to find that your returns on your tall poles are, uh, something that helps out in the family but may not be as life changing for you as it is for the entrepreneur that you invested in. That's because general partners are typically working. They're working folk, right? Granted, it's a certain kind of work. It's financial services. And it's often considered to be at one end of a spectrum of financial services. But it's still work. General partners are still working. A general partner is hoping to become a limited partner and somebody else's. So these things are often missed. And particularly in the power imbalance that occurs between entrepreneurs and VCs, entrepreneurs often times feel like they're supplicants coming to A vc, right? Like you're coming to someone on a mountain and saying, oh please rain money on me. Right. And you may miss that. The fellow sitting on the mountain, his perch may not be as comfortable as it looks. He has a lot of things that he's trying to do too. And so to the degree that you can align to him, and I should say her as well, there's a lot of evidence that shows that women are very good investors, produce very good returns relative to their male counterparts. In any case, whoever it is that you're talking to, they have their own set of concerns. And so to the degree that you can be cognizant of those, I, uh, think you can really help yourself in terms of arriving at the right time. So is this VC active? Are they dispensing funds? They have a 10 year fund, but they're probably only active in years like but say 2 through 4 or 2 through 5, then any capital they have is being reserved. The companies that win in their first port, so what, you may have a portfolio, but then you have to partway through your first portfolio, you have to create your second portfolio. That means you have to raise a new round of capital. It also has all the problems that I just described. You might be raising your second round while you're still losing money in your first round. So these are all things to think about. VCs are just like anybody else in capitalism at this level. They're trying to put resources, whether it's time or expertise or networks or money, to work in ways that are productive and outrun inflation. I guess, uh, we're also trying to outrun everything else. The S&P 500 produces a very good return right now where we provide an illiquid asset.

Speaker B: We'll ignore that little S and P comment, but keep it organic or evergreen content. Alex, question on the VC fund itself. Are uh, there certain metrics that a new fund manager emerged? Fund manager should be tracking whether it a number of deal flow or number of LP meetings. Or is there any metrics that they should think about for themselves or the fund to help with the probability of success?

Speaker A: Yeah, I'm glad you put that last bit on there because there's only one thing that matters. There's only one metric that matters which is how did you do for your investors? But along the way to that answer, there are a lot of interim measurements. The most important interim measurement is called the internal rate of return irr. The IRR is it's the gold standard. It's not the gold standard that's the word. The IRR is the most common standard of success. Ah. However, IRR can be a little bit misleading because of the effects of time. And I'm, um, not going to try to go into the math of the IRR here. I'll just say Excel can do it for you if you look it up. Quad will do it for you in Excel if you don't want to do it yourself. So the internal rate of return, very important metric. And the internal rate of return kind of measures the internal efficiency of money. How well are you doing at, uh, increasing the growth or the value of the money that you have under your management? It's currently deployed. It's an indicator of what will probably be your DPI or distributed returns. Okay. And that's your really your most important. But that metric is many years away. That's your. How much money did I give back? There are certain things you can consider. How many deals have you looked at? Certainly you say no to more deals than you say yes to. Depending on where you're doing your fishing. Are you doing your fishing at a university? Okay. Then you're probably going to have a certain kind of ratio. Are you doing your phishing at, uh, a local. At local networking events, you're going to have a kind of ratio. Are you doing your fishing where we do a lot of our fishing, which is at the end of other people's due diligence streams. Right. So we invest alongside of the Sacramento Angels, we invest alongside of Y Combinator or we invest alongside of techstar. So we invest alongside of Berkeley Sky Day. These are all companies that we have access to and we're very pleased to be part of. We have a kind of different metric that we use because we're using. We're dipping our toes in where people have already done a lot of filtering, a lot of work, a lot of training. So it's very important to understand where you are in cycle. And I actually have a screen that probably shows that pretty well, if you don't mind. John, you had a minute? Yeah.

Speaker B: But uh, just remember, for the people listening in audio, you're gonna have to describe it quite a bit.

Speaker A: Oh yeah, forget it. Go look up the startup financing lifecycle and understand what's known as the value of debt. And you can Google it anywhere, you'll find it, it's on Wikipedia. And understand that the earlier you invest in a company, the higher the multiples are that you can conceivably return from that company. However, the greater the risk is as well. So the earlier you invest, the more your investment's going to tend to zero and the higher your returns are going to be on the ones that do win. And the later you invest, the less likely it is to go to zero. But you're also probably not going to be collecting the 1000 to 1 or 100 to 100 returns that you might get early.

Speaker B: Early stage companies, early on raising a friends and family round. And many of those companies never get in the attention of, uh, venture capital or institutional investors. Should a founder really just think about, okay, if I do a friends and family round, how do I make this company break even a profitable from this money? Or should they be thinking about what's beyond that round? Maybe a second marriage or a divorce? I don't know what the, uh, analogy would be.

Speaker A: You'd marry many people.

Speaker B: There you go.

Speaker A: Polygamy.

Speaker B: Should they think about polygamy or should they think about just that one friends and family, marriage and what they can do with that?

Speaker A: Yeah, I'm going to stay away from the loaded term. That's question. Let the metaphor serve to its end use. Uh, the answer is it depends on what kind of business you have. Right. Kind of business do you have. And it's important to understand that there's a large range of businesses because there's been many forms of capitalism over hundreds of years. Right. Or many forms of commerce for hundreds of years. Capitalism is a relatively novel introduction, but people have been making everything from buggy whips to parts for computers. People have been providing cleaning services since time immemorial, I'm sure. And since the advent of the semiconductor compound, um, semiconductor in particular, people have been building in what's, what was called the information age. Now I think we should call it the intelligence agent. That's not my insight, that's the community's insight. Right. There was the era of information and all that information begat large data. Um, large data, uh, begat machine learning, begat machine learning, begat artificial intelligence. Now most people understand LLMs is the most common form of artificial intelligence. But that's a topic we can go back to. The answer is it depends on what kind of business you are. Are you the kind of business that just needs a slug of capital to get. Do you just need to create a factory? And if you don't have a factory, you can't produce a product. And if you don't produce a product, you'll never make a dollar. That's one kind of model. Uh, are you a, are you a software company that needs to write an early Prototype in order to demonstrate an important concept that's probably your money and your time, are you now ready to take that out to market and test it? And you need a few dollars for advertising. You need to find out if it works. That's probably the first step in what will be a journey of uh, fundraising. And depending on what kind of startup and what kind of software company you are, you might reach break even relatively quickly. Which is why startup companies are so attractive for venture capital. It's because they, they're not typically bound by the laws of physics. Venture capital is usually looking for businesses that are not subject to physics. Understand? Okay, right. And physics is tough, man. Physics M is tough. Gravity applies to everybody. Distance applies to everybody. Roads eat cars. So it's just, it's better if you can find a business to invest in. It's not subject to the laws of physics. But I do both and our team does both because sometimes great products are too exciting to pass it. Alex, when we were having a call

Speaker B: before the interview, we talked a little bit about digital currency and the intersection with government regulation. What do you think of some, the challenges or opportunities out there for entrepreneurs around this?

Speaker A: He's one of the greats who said software will eat the world. And he was not wrong. He was not wrong. One of the investment theses that uh, is central to our core here at Evolution is that technology decomposes monolithic industries. That's our first, our first leading thesis, Technology decomposes monolithic industries. That ah, means that I'm looking for certain kinds of businesses. Blockchain is a great example of technology decomposing monolithic industries. The most common monolithic industry that we think about decomposing, we think about blockchain decomposing is banking money. Right? Because most people think about blockchain in the context of money because that's one of its more useful, it's one of its more successful use cases. I don't know if it's a useful use case, but it's a successful use case. Guess if it's successful it must be intrinsically useful. It has some challenges. Blockchain is an imperfect medium for money, but it is an alternative to government FIA and the decomposition of the banking industry. This is a, this is a matter of some concern to the state. And that points to the second thing that blockchain tends to decompose, which is the state itself. Right. Because there are very few things that the state maintains as tight a, uh, hold on as it does the issuance of its own currency. These are things the state cares deeply about. Ask the Secret Service, who have spent the last century chasing counterfeiters. This is very important. And so in that context, do I think it matters? Oh, yeah, absolutely. We invested in a company last quarter that specializes particularly in cross border transactions between Mexico and the United States. And this is a very important economic space. And small businesses and medium sized businesses operating in that space can wait as long as two weeks to have their transactions cleared and access to their money. And it's problematic, it's fraught with paperwork and many things happening here. The company that we invested in uses blockchain. I'll just say the Stellar Network. You can find them on our website if you're interested. But I don't want to show for them. Okay. They're just a very smart group of people that have figured out how, uh, to take that two week transaction clearing period and turn it into a one to two hour transaction. Clear? Okay. What's the time value of money? What's the value of that entrepreneur's, uh, attention? It's very high, extremely high. And the state and banking, which are the current monolithic industries that capture the cross border transaction function, are being decomposed by blockchain. And yeah, I mean, it's worth looking into is what I'll say. Find people that are solving real problems. So this is not an endorsement for Meme Coins.

Speaker B: Alex, before wrapping up, what's one piece of advice to aspiring entrepreneurs or investors that you'd want to pass on from this interview?

Speaker A: It's a thought that I've shared many times, and I probably shared it too many times, but I still think it's a useful and valuable thought, which is that, uh, as an entrepreneur who's seeking funding. Right. So here I'm speaking to those in your audience who are out looking for money, it can very much feel like you're panning for gold. And panning for gold, if you've, if you remember that that class from high school can be very cold, very freezing, very miserable. Or you can stand in your waist, stand up to your waist in freezing cold water sifting dirt. That's the plan. Okay. And it can be very frustrating. And what I would like for you to understand as an entrepreneur is that the entire ecosystem of the fundraising world, the whole milieu, is actually panning for you. You're the goal in the ecosystem, not us. We are the ones that are sifting through all of the detritus and miscellaneous things that come our way looking for the gold. And so if you understand that as an entrepreneur, you are the gold that we're all looking for. You are the thing that's actually valuable. You can hold that in your mind. I think you'll find the journey more rewarding and the experience to be more fulfilling.

Speaker B: And Alex, if anyone wants to find out more information about yourself, what you're working on, the organizations you're a part of, what's the best way to go about doing that?

Speaker A: Oh, we have several online communities, very easy to find. Just search for Evolution Accelerator, and that's us. EVFM is our domain for investors, and Evolutionacceleration.com is our domain for entrepreneurs. And we would invite you to join our community. And we do our very best to make information as broadly available as possible because our goal is to see ethical capitalism in full flower and form. So we are here to help garden, and we hope that we have the opportunity to help you.

Speaker B: And then before wrapping up, the views expressed in this podcast are for informational purposes only. They do not constitute financial legal advice, nor do they necessarily reflect the views of, um, finalis Incorporate Securities, LLC member, finra, sipc. And for our audience out there, if you want to go to the bestsiliconvaluedpodcast.com to check out our archives and what we're working on. And when I'm not the host of the Silicon Valley Podcast, my name Becker, focused on mergers, acquisitions, growth capital and secondaries. Feel free to connect with me on LinkedIn. And with that, Alex, I want to thank you for being a guest on this week's episode of the Silicon Valley Podcast.

Speaker A: Thank you, Sean. It's been an honor to be here.

Speaker B: Thank you for listening to the Silicon Valley Podcast.

Speaker A: To access our, uh, resources, Visit us at TheSiliconValleyPodcast.com and follow our host on

Speaker B: Twitter, Facebook and LinkedIn.

Speaker A: Ah, Sean Flynn, SV this show is

Speaker B: for entertainment purposes only. Before making any decisions, consult a professional.

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