The Twenty Minute VCMo Koyfman: The Secret to Winning in Venture; Why Small Funds Outperform Large Funds | 20VC #915
EVERY SPOKEN WORD
110 min read · 21,523 words- 0:00 – 0:39
Intro
- MKMo Koyfman
(instrumental music plays) Three, two, one, zero. You have now arrived at your destination.
- HSHarry Stebbings
Mo, this is such a joy to do. I've been looking forward to this for a long time. I've wanted to have you on the show for a long time, so thank you so much for joining me today.
- MKMo Koyfman
It's absolutely my pleasure, and as I was just saying to you, I haven't really done much press, um, not that this is press per se, um, since I started Shine, and, uh, when you reached out, I thought this would be a great opportunity to share some of my current thinking. So thank you again for doing it.
- HSHarry Stebbings
Not at all, but it is a fantastic opportunity. And I want to start with a little bit of context.
- 0:39 – 7:45
How did you get into venture?
- HSHarry Stebbings
And so talk to me, how did you make your way into the world of venture that I clearly love so much, having done 3,000 episodes? And then how did you come to found Shine most recently?
- MKMo Koyfman
Yeah. You know, honestly, it was an accident. Uh, if, if you would have asked me about venture capital when I was in college, I, I literally wouldn't have known what it was or barely knew what it was, and I'm dating myself here, but that is the truth. Um, as my old boss, Barry Diller, liked to say, I just put one dumb foot in front of the other.
- HSHarry Stebbings
(laughs)
- MKMo Koyfman
Um, to be honest, my family background has a lot to do, uh, with where I am today. Uh, my father is an immigrant from the former Soviet Union who came to America when he was 35. He didn't speak a word of English and he didn't have a penny in his pocket. All he had was his intelligence, his education, he was an electrical and mechanical engineer by trade, and his determination. He was helped by a Jewish refugee organization called HIAS and spent his first few months in the US learning English, after which he started as a draftsman at an engineering firm in Manhattan where he met his eventual business partner. Six years later, they started their own engineering firm and they grew it over the next 30 years to be one of the preeminent MEP shops in the city. MEP stood for mechanical, electrical, plumbing, but since they've added telecommunications because obviously that is a core part of infrastructure for commercial real estate today. My mother on the other hand, was the child of immigrants and grew up in Brooklyn. Uh, they didn't have much, but she got a good education and she was embraced by a warm, loving family and community. She moved to Israel after college where most of our family now lives, and met my dad on a trip back to New York where, in her words, she got stuck. My mom, interestingly enough, is an OG software engineer.
- HSHarry Stebbings
(laughs)
- MKMo Koyfman
She learned to code before she moved to Israel, figuring it would be more useful than her Hebrew teaching degree.
- HSHarry Stebbings
(laughs)
- MKMo Koyfman
Um, ultimately, she too started her own consulting business, writing and troubleshooting code for companies like ABC Networks, uh, Blue Cross Blue Shield, ADP, et cetera. And so my entrepreneurial inclinations definitely come from my folks. I was cr- quite inspired, uh, by their respective abilities to forge their own paths, especially given the hardships they had to endure to, to get there. I went to Penn, uh, as an undergrad where I studied finance at Wharton and English literature in the college. I've always been a left-brain/right-brain thinker, and I believe that's how I ended up in venture capital. Think we'll touch on that more later. And aft- after Penn though, uh, like many of my peers at the time, I sought to join an investment bank. Um, that's what we were all doing. Venture capital and entrepreneurship was not the thing to do in the late '90s. Um, in fact, it was quickly falling out of vogue. Um, I ended up at Bear Stearns because it was the most entrepreneurial bank I could find, and Bear had a culture like no other which allowed young folks like myself to really punch above their weight. This penchant for risk ultimately undid Bear, but for a young, aggressive entrepreneurial banking analyst like myself, it was a dream version of the genre. I was lucky enough to be recruited to IAC in 2001, or as it was known then, USA Networks, from Bear. Um, I joined the strategic planning team who interestingly enough, we were just talking about this, was then being run by Dara Khosrowshahi, who's now the current CEO of Uber, who hired me into IAC, as well as a guy named Jeremy Liew, who you may also know who led consumer investing at Lightspeed for a while.
- HSHarry Stebbings
(laughs) Absolutely.
- MKMo Koyfman
And ... Yeah. So there were basically six of us that were responsible for strategy and M&A at the company a- at that time, including Dara and Jeremy.
- HSHarry Stebbings
Oh, really?
- MKMo Koyfman
Yeah. I had an incredible six years at IAC where I learned more than I could ever have imagined. Uh, it was a remarkable time for the company. We were flush with cash after the Vivendi Universal Entertainment transaction, and Barry decided to scoop up internet assets that had fallen out of favor. It was an incredibly prescient decision and we ended up consolidating massive Web 1.0 categories that we later spun out to public shareholders including travel, dating, ticketing, lending, and many others. As the market started to heat up ahead of the '08 crisis, we could no longer find attractively priced assets to buy, so Barry pushed us to go earlier and flex our entrepreneurial muscles. It was in this capacity where I was ultimately involved with, uh, where I was intimately involved, excuse me, with incubating and acquiring a handful of early stage businesses. Most notably, I led the acquisition of Connected Ventures which was an incubator itself of sorts, and, and Connected Ventures included assets like CollegeHumor, an early content site, Busted Tees, and Vimeo, an early video sharing business. I ended up joining the founders, Ricky and Josh, as COO, and among other things, helped Vimeo recruit its early team and operationalize a business around the beautiful application its founders had designed. In fact, I now sit on the board of Vimeo and chair the comp committee and the nominating committee, uh, coming full circle almost 15 years later.Through this experience, I really fell in love with the early stage of business building and decided that is where I wanted to spend my time moving forward. So I ultimately decided to leave IAC, and I joined an upstart venture capital firm out of Boston called Spark Capital. As I was joining Spark, Bijan Sabet at Spark led Twitter Series B, and that investment catapulted us into the upper echelon of VC firms. Over the next eight years, I helped Spark cement that position and led a number of successful investments for the firm, including companies like Warby Parker, Sift, Skillshare, Hive Mapper, and most notably, Plaid. I led the seed round in Plaid and joined the founders, William and Zach, as their first outside board member. Ultimately though, the entrepreneurial bug, first instilled in me by my parents and further strengthened through working with the incredible founders that I've had the opportunity to work with over the past 15 to 20 years at this point, um, that bug bit me and I decided to start something on my own. I didn't know what form this would take, by the way, when I started at first, and I gave myself some time to figure it out and roll off my obligations to Spark. But after spending some time investing as an angel and advising startups, I ultimately decided that an early stage firm based in New York City is really what I wanted to do.
- HSHarry Stebbings
Can I ask you, you know, you spent a lot of your early more formative years investing at Spark. We mentioned going off schedule, it's a skill I have. When you think about, like, the biggest takeaways and how they impacted your mindset in the founding
- 7:45 – 10:59
Biggest takeaways from time with Spark Ventures
- HSHarry Stebbings
of Shine, what are some of your biggest takeaways from your time with Spark, and how do you think that impacted your mindset founding Shine?
- MKMo Koyfman
Yeah, I mean, honestly, what I learned at Spark most importantly is that I love early stage investing. Um, and I also realized that I had learned a tremendous amount, both at Spark and at IAC. And after having a little bit of time and separation and distance to sort of, um, t- you know, I, I think it's really important to have perspective in life. I, I needed some time to separate myself. Both when I left IAC, I took six months, and when I left Sh- uh, Spark, I took 18. I had non-competes and non-solicits to roll off and all that stuff, but most importantly, I wanted perspective. And what I realized is that I love early stage investing, I'd learned a tremendous amount, and I was very eager to apply that to new businesses, new entrepreneurs, and new challenges. And I also realized there was no better time to start a firm in New York City. That's ultimately how Shine was born. One of the core things I learned beyond that, to your question, is really around the difference in structures of venture capital firms. Um, you know, when I came up in venture, many firms were built as partnerships, and this was often a function of previously successful entrepreneurs and investors banding to- together to create a structure that provided for maximal individual freedom while leveraging their collective expertise to build venture capital portfolios. And while the partnership structure has many adva- advantages from an investment point of view, in terms of getting a group of extremely talented people to work together and produce a diversified basket of investments, there are a lot of trade-offs around investment and personnel decisions when governance becomes more broadly divided. Whereas investment firms, on the other hand, tend to have more clear leadership structures, even if there are a number of senior investors, all of whom share ratably in the proceeds of their work. And while both can certainly work, and there are ce- and there are notable exceptions here, like Union Square Ventures for instance, which works very well as a partnership structure, the more durable firms, in my experience, often have very clear leadership and governance structures. And something that I learned, um, at Spark is that I would do better in a structure like that, and I, what I really wanted to do with Shine was build a company that modeled the, the company structures that I saw in the best startups we built, um, but did it in a way that was completely meritocratic, um, fundamentally first principles-based, but ultimately had clarity of role responsibility and structure so that we could really empower everyone to make the best decisions possible and we can make the best decisions as a group.
- HSHarry Stebbings
I need your help, Mo. I use these sessions as learning sessions. I have the same structure as you. There is very clear hierarchy (laughs) in my firm too, um, which is why no one probably would ever employ me. Um, but-
- MKMo Koyfman
(laughs) By the way, I don't think anybody would employ me either at this point.
- HSHarry Stebbings
(laughs)
- MKMo Koyfman
So this is both out of desire and out of
- 10:59 – 15:11
Strong opinions, weakly held
- MKMo Koyfman
necessity.
- HSHarry Stebbings
But my question to you is, you know, oh, I spoke to your team before. I spoke to Olivia, Ethan, Amanda, and they all said to me many great things, but they also (laughs) said, "You have strong opinions on a lot of things. You're quick to build them, and you're not shy in asserting them." The worry that I have is that, bluntly, I can shoot people down too soon and I don't give people the oxygen to share their thoughts, because they say, "That doesn't work. That doesn't work. No, I don't like that. No, I don't like that." And actually, I need to create an environment where they can say, "Yes, I want to do this," or, "No, I don't think we should do that." How do you think about giving them the oxygen and freedom to, with both the hierarchy and clear delineation, and also your opinionated self?
- MKMo Koyfman
Yeah. Um, you know, I live my life by, uh, a very simple moniker, uh, in this regard, which is strong opinions weakly held. And, um, I feel this way to my core. And, um, I know you'll ask me about this, this later, but as a, a presage to that, you know, having strong opinions is both a blessing and a curse, right? It is, it can be one's greatest strength and their greatest weakness. Um-... but I think it's really, really important to have strong opinions. I think, um, people who don't take strong points of view tend to be quite boring and uninteresting, um, and I have no interest in being boring. Um, I, and I don't look for people that are boring. I'm drawn to people that are interesting. And almost definitionally, to be interesting, you have to have a point of view on anything that you're talking about at any given time. You have to take a stance. You have to have a point of view. So my approach to the world is to have strong points of view, not being shared, uh, not being scared to share them and to articulate them, and to present a compelling case for them. But I am deeply compelled by data, and I am very open to be proving, proven wrong. In fact, I, I like it, and a lot of this comes from my education. You know, I, I grew up, as I've alluded to, in a, in a very traditional Jewish household, um, and so much of the Jewish tradition is around, um, this kind of study and learning and exegesis. Um, in fact, a little-known fact about me, I went to a sort of Jewish day school, uh, fairly modern, but, but again, uh, a parochial school, and I won the Talmud award in high school. And for anybody that's ever t- studied Talmud, they will know that it is literally about debate. And when I was at IAC, Barry used to call our Monday meetings, our Office of the Chairman Meetings, The Dynamic Debate. And we would sometimes sit in there for eight hours yelling at each other and screaming at each other to get to the right answer, and I am much more fundamentally interested in getting to the right answer than I am in being right. And so, that is how I balance these things. I put out opinions that I feel strongly about, but I actually encourage people to challenge me. I ask them to challenge me, and I push them to find data that challenges my assumptions, and if I think I'm right and I don't have the data to back it up or to refute it, I actually... We, we, we together as a team will go out to do just that work, because ultimately, um, that, the, the, i- the, the moniker of strong opinions weakly held is crucial to me. And I think if you're not willing to test your assumptions, you end up, um, as an absolutist or you end up, uh, very susceptible to groupthink, and I think both of those things are poison for decision-making. And as venture capitalists, um, or investors in general, or even in life in general, the most important thing we do day in, day o- day out is making decisions, and we do that on a macro basis and on a ton of little micro bases. And so everything I do is all about trying to make better decisions, and believing your own bullshit is not a way to do that.
- HSHarry Stebbings
I totally
- 15:11 – 16:52
Do you have mentors who challenge you?
- HSHarry Stebbings
agree with you. Do you have mentors who challenge you on your bullshit? I found that very helpful.
- MKMo Koyfman
I do. In fact, um, I have a, I have a handful of mentors who challenge me on it, and, and interestingly enough, um, they can be extremely different. Like, some of them will tell me one thing, and another will tell me the exact opposite, and in many ways, that's interesting. Uh, you know, the other day, um, I was talking to one of my foremost mentors, Fred Wilson from Union Square Ventures, and he literally was screaming at me on the phone, and I loved it. Like, I, I honestly loved it, and it's totally Fred, and he knows with me, he can just kinda let it loose and say what he feels. And I was sort of recounting to, to him something, um, that another one of my mentors had shared, and he was like, "No, that is total bullshit." Like, "Absolutely not. Don't listen to that. You have to take risks. That's what venture is all about." Like, et cetera, et cetera, et cetera. And I, I value that tremendously. So, so to the point, um, I always want people to call bullshit on me, and, um if they're right, I will take it in stride.
- HSHarry Stebbings
I, I'm fascinated. You've mentioned Fred Wilson there. You've mentioned USV. When we spoke about kind of the venture partnerships, I also thought of immediately Benchmark, and then with others, you know, investment firms, traditionally, they actually scale much bigger. USV and Benchmark obviously both very limited in terms of their fund sizes compared to what they could raise. Investment firms tend to scale a lot more when we look at the biggest incumbents
- 16:52 – 19:33
Getting bigger is inversely correlated with getting better
- HSHarry Stebbings
today. Um, you said to me before, getting bigger is inversely correlated with getting better, uh, as a manager (laughs) looking to scale, I was interested to hear your thoughts. What did you mean by this?
- MKMo Koyfman
Yeah. Well, to be clear, investment firms can grow and continue to perform quite well against their stated re- return objectives, um, and increase their assets under management. So, like, I'm not making a damning comment on the entirety of the investment management business, and I think, um, we could talk about that at another date. But, but what I'm really referring to, or what I was really referring to, uh, with that comment is specifically the business of early-stage investing, which you and I both practice.
- HSHarry Stebbings
Mm-hmm.
- MKMo Koyfman
And, um, not to harp on Fred, but it's a great example of, um, mentorship and, um, getting good guidance and advice from your mentors. When I started Shine, Fred and, and Joanne Wilson were my first investors. And when Fred told me they were going to invest in the fund, he gave me a sliding scale of how much capital he wanted to put into the fund. The larger the fund, the less money he was willing to invest. Simple as that. And his lesson to me was very straightforward.... larger early-stage funds always lead to lesser returns over time. And it's not simply because it is harder to return larger pools of capital. What he was teaching me in that moment, and it was a lesson that I had learned before but needed to learn again, um, is that the reason, um, um, larger pool of capitals, uh, end up performing, uh, poorly or less well than smaller pools of capital in early-stage investing is because the la- of the lack of constraints. And it's, it's actually the same thing we warn our companies against, and why the last few years of irrational exuberance are going to be so devastating for many, many previously high-flying companies and a number of venture funds. Keeping early-stage funds relatively small imposes constraints, and those constraints force you as an early-stage investor to make considered choices about how many deals you're going to do, which deals you're going to do, how much you're gonna be putting into those deals. You, you simply don't have the luxury of YOLOing it-
- HSHarry Stebbings
(laughs)
- MKMo Koyfman
... and that alone often makes the difference between a good fund and a great fund.
- HSHarry Stebbings
I absolutely agree with you. Okay, you're getting on to one of my biggest passion points, which is why I'm single. Um,
- 19:33 – 24:39
How big is Shine Ventures today?
- HSHarry Stebbings
uh, let's talk about the por- portfolio construction. How big is Shine today?
- MKMo Koyfman
Um, in terms of number of portfolio companies?
- HSHarry Stebbings
In terms of fund size.
- MKMo Koyfman
Oh, so fund size, uh, we manage about $435 million or so. Um, our first fund was $125 million early-stage fund. Our second fund is a $200 million early-stage fund, and we have $100 million opportunities vehicle that we can invest cross-fund to lean into, uh, the companies in our broader portfolio that perform.
- HSHarry Stebbings
Okay, so let's take the $125 million fund here. What does that look like from a number of lines per fund and a capital per company basis?
- MKMo Koyfman
So we did about 25 deals in Fund 1.
- HSHarry Stebbings
Yeah.
- MKMo Koyfman
That is generally the right number for us, given that we do both seed and Series A investing, and we tend to be a, um, uh, lead, lean-in, active, engaged investor. Um, granted in Fund 1, um, we did do some experimentation with some smaller checks, um, especially around crypto as we were legging into some Web3 investing. But for the most part, we like to lead or co-lead rounds, um, and we're typically writing for a seed, call it, one and a half to $3 million to lead a round and for an A, six to $8 million to lead a round. And if we really push it, we could probably go up to 10.
- HSHarry Stebbings
Tell me, is 125 enough then? 'Cause when we think about reserves, people forget, you know, 125, you take away the fees, which is 20% or whatever that is, and then you take away reserves, and suddenly a 125 fund size is actually 62 and a half.
- MKMo Koyfman
Yeah, I mean-
- HSHarry Stebbings
Up there.
- MKMo Koyfman
... honestly, um, no is the answer. Not for our strategy. Um, it could be enough for other strategies, more seed-oriented strategies. It could be enough for a more concentrated portfolio if people want to run a much more concentrated book. I like our concentration where it is, having been doing this now for 16 years. I believe in having enough ways to win in the fund. Um, and ultimately 125 was a bit small for our first fund. I'll tell you a story about that, which is that, um, the reason ... (laughs) Again, not to harp on USV, but the reason we capped our first fund at 125 is, um, that was the size of USB's first fund, and we shared one LP who was like, "Why don't we just cap it at 125? It's, it's, uh, it worked for Fred. Why, why, why wouldn't it work for you?"
- HSHarry Stebbings
(laughs)
- MKMo Koyfman
And in general, in life, that's a, that's a pretty good, um, that's, that's, that's a pretty good, uh, uh, tact to take. Um, but, um, what happened was, we capped it at 125 during COVID. So I had the unfortunate reality of raising Fund 1. Literally, we started in the late fall of, um, um, 2019, and, like, got hit by COVID, like, four months into our first fundraise, um, and really just wanted to constrain the problem, create scarcity value around the fund, and use that as a way to attract capital. In hindsight, it's funny, when we did our final close on the fund, um, I actually went to our LPAC and asked them about making the fund a little bit larger and going to 150, and they gave me permission. Um, all the LPAC members actually gave me permission to take the fund up. And something didn't sit right with me about it. I had given them my word, um, that I was raising 125, and that was the cap, and I just didn't like the idea of my first, um, decision, my first move as a G- GP, to be going back to my LPAC and to ask to blow through my cap. So I basically just said, "You know what? Forget it. I'm gonna keep it at 125, and if it ends up being too little, um, we'll figure it out." And so part of the reason I raised an opportunities fund pretty early in the life of our fund is to make sure that we had enough dry powder, um, for Fund 1 companies that performed, and that gave me the comfort to slightly overinvest Fund 1. So our reserve ratio in Fund 1 is a little less than I would have liked it. We're probably trending...... 65/35 on, um, first money in, uh, maybe a little bit more. Um, we've taken that down a little bit in fund one, but I think our structure of, of using opportunity funds for the companies that do best allows us to overinvest a little bit upfront, um, reserve a little bit less in the core fund, and then use the opportunities fund, um, when we have companies that are really
- 24:39 – 27:35
Reserves and allocation in the face of unknowns
- MKMo Koyfman
knocking it out of the park.
- HSHarry Stebbings
You know what I find challenging about reserves, Mo, is the fact that often, you know, the companies that need reserves most, uh, either the massive winners who come back fast or strugglers who come back fast. And you have to kind of proactively forecast in an unknown world what could happen with reserves well ahead of time, not knowing. How do you think about embracing that cha- mental challenge of allocations on unknowns as a fund manager?
- MKMo Koyfman
Yeah, it's a really interesting point, and it hearkens back to your question around, uh, the lessons I learned from Spark. Um, one of the... You know, reserves is, is extremely tricky. It's a very, very tricky business. It's especially tricky in a partnership model, because, you know, what happens in venture partnerships is you have investors at different stages in their careers, optimizing for different things, and their own personal, um, desires and positioning within the firm and biases, what they're trying to signal, will enter into the discussion. And that, you often see that leading to suboptimal reserve decisions and sub- suboptimal follow-on investment decisions.
- HSHarry Stebbings
Mm-hmm.
- MKMo Koyfman
So I took a totally different tack to doing reserves at Shine, which is, we don't actually reserve per company when we do a deal at all. Um, I actually reserve a bucket for the entire fund, and then, you know, my old, uh, partner, f- one of the founders of Shine, Todd Degress, used to refer to it as, uh, they're not reserves, they're deserves. Um, and that always stuck in my head, but the reality was, in practice, um, they always became reserves. And so I tried to structure it at Shine where they actually were deserves. So when we make an initial investment, especially early on in a company, we actually don't attach formal reserves to the company. We do some math in the background, and I work on that with my CFO to make sure that we're not doing anything stupid, but we actually... we have a bucket of reserves that we apply to companies as they perform, and that allows us to be a little more rigorous about who gets reserves, because it very much is, um, a haves and have-nots game, like meaning it forces us to only put capital in companies that really deserve it and not to throw good money after bad. And so I, I really have structured our firm and our decision-making and our processes to avoid throwing good money after bad. And, and you're gonna ask me now, "How do you navigate that with entrepreneurs? Like, it's so difficult, right? When they come to you for capital, and you don't have the money to support them?" And what I will tell you is... Mm-hmm. Yeah, go ahead.
- 27:35 – 32:38
Thoughts on Pro Rata and VC competition
- MKMo Koyfman
- HSHarry Stebbings
I wa- I was gonna ask two questions. One is, like, how do you... Bluntly, do you worry about competition when we have a VC landscape who often say, "We will blindly give you pro rata regardless," which I see very often, and I'm worried communicating to founders who do say, "What's your take on pro rata?" And when you say, "Hey, it's a meritocracy, and it goes to the person who deserves it," I worry that I'm losing a competitive edge to the free-flowing cash that comes from a big firm who says, "Yeah, pro rata always."
- MKMo Koyfman
I- I- I don't... Um, first of all, I'm not even sure I buy that. Like, anybody that says they do pro rata always, I think is lying. I- I- I- I just, I don't believe that to be the case, and I've seen enough. I've been in venture long enough to know that that's total bullshit. And by the way, um, to be clear on pro rata, um, we always do pro rata if the company deserves it or if the situation warrants it. So to be clear, there are times when a round is getting done, and in a vacuum, if you asked me, "Does this company deserve pro rata on a standalone basis for what they've achieved today vis-a-vis what you underwrote at the beginning?" I might say, "No, I don't think they do." But if there's a round coming together and somebody in the market is willing to pay forward and give the entrepreneur credit that they will actually achieve what we all from the beginning set out to achieve together, and us doing our pro rata is essential to getting that round done, to the right signaling, et cetera, et cetera, I'm never gonna hurt a company by not doing pro rata, ever. I will never do that. The only time I won't do pro rata is if I don't need to or I know it's the best thing for the company. So in hot markets, for instance, it turns out that over the last few years, you don't have to do your pro rata. You never had to do pro rata because every new investor under the sun will gladly take your pro rata if you give it to them so they could put more capital to work and own more of the company. And by the way, even into the downturn that we're facing right now, these, most of the big funds have so much capital that they don't give a shit if you do pro rata or not. They'll take it regardless. So you don't have to. If a company is able to go raise money from the outside, you can do your pro rata. You don't need to do your pro rata. That signal around doing pro rata is, is just simply not what it used to be, uh, number one. And number two is, if there's a round, like if there's a company that's not doing well, and they want you to do pro rata...... the reality is, especially in the current environment, like if they're actually able to get a VC step up to do the round, and we need to put a f- a little bit of money in to- to- to signal properly and to make that happen, of course we're gonna do that. But the reality is that most companies that are having trouble on a, "Of course we'll do pro rata no- no matter what," you know, uh, uh, basis, convincing their existing investors that, "No matter what, you know, we'll write a check. It doesn't matter." Like, the reality is that those companies are gonna have a hard time getting funded if folks like us don't feel excited to do our pro rata based on, um, uh, the- the- what they've been able to deliver thus far. A- and- and this is, this is a conversation I'm having with a couple of companies right now, and it's one of the hardest thing for new VCs to do, but I- I, mark my words, it is an, it is such a valuable thing, um, that- that- that you are doing for entrepreneurs, and it's something that we're gonna have to do over the next couple years time and time again. The best thing you could do for an entrepreneur who is working on a project, who is working on a business that you know and believe is not gonna work is to tell them in the nicest, kindest, most genuine and sensitive way that for the following reasons, you don't believe this is going to be successful. If there's someone else out there who's willing to fund it, godspeed, and if we need to do some amount of pro rata to make that happen, we're not gonna kill your company, but you should take a really hard look in the mirror, you should take a really hard look at what you're doing, you should think about it for a while, and then we should have an honest and open discussion around whether this business can work, especially in this environment. And if it can't, either you need to hard pivot into something that's gonna work and get your investors behind you in doing that, or you should shut down the business and return the capital. And by the way, the investors are- that- that are in your cap table today are infinitely more likely to back you agr- again watching you make that kind of mis- mature decision as an entrepreneur rather than watching you piss that money down dr- the drain over the next two years, and actually, in many ways, waste two years of your life with a very high opportunity cost that you could put against something way
- 32:38 – 35:40
Communicating with founders about Pro Rata
- MKMo Koyfman
more valuable.
- HSHarry Stebbings
The hardest thing for me is the, uh, and often is the case, is the gray in between, where you have a company that's doing okay. It's doing fine. But in the capital constrained world that you and I both live in and both quite enjoy and like, um, there's an opportunity cost of that capital, and every dollar you allocate to an okay company is a dollar that goes away from a significantly high performing company. And so, how do you communicate in that case, where it's not, "We don't believe in you"? It's just, "You're not as good as others." Right?
- MKMo Koyfman
Look, u- u- unless what they're asking us is to step up and lead a round, which I do not feel compelled to do under any circumstance other than when I feel compelled to do it, i- it's kind of a null set, um, 'cause if you think about it, when we're in, um, go-go markets and capital's cheap and everything's getting funded, we could choose to do our pro rata, we don't have to do our pro rata, kinda doesn't matter. We've talked about that already, and you've seen it. In the last couple years, whether we did our pro rata or not made no difference to the incoming investor. We're now about to enter a period whereby it'll be a function of whether they can get anybody to write a check. Like, if a company is able to get a quality VC to write a check, then in some ways, that in and of itself makes that company better than it was before, because not that capital is a moat or a barrier or anything else, but having more capital to give you more time to achieve your objectives means that we're getting leverage on our capital and the likelihood of success is going up. So, if we have to write a pro rata check, if today new investors are actually looking for us to write more pro rata checks as a signal, which by the way, to be clear, I'm still not so sure they're gonna care about given fund sizes and how many investors they are. But if there are and that signal really matters, and round sizes are coming down and valuations are coming down, and in a sense, having more capital de-risks the company, then it actually is kind of an easier pro rata decision, because putting another half a million dollars or a million dollars into something that's getting funded by a good firm at a rational price and gives them more opportunity to win, all of a sudden it's not a bad pro rata decision. So like, that- that situation where a company is getting funded and you really don't want to do your pro rata, it doesn't really happen very often. It did happen recently with us. Um, but our pro rata was so small anyways that it didn't even matter. It was like our pro rata was gonna end up being a few hundred thousand dollars, and I said to the entrepreneur, like, "O- obviously, that's not gonna move the needle for the round. If it did, like obviously we would do it. It- it's not gonna matter, but all else being equal, we're fine with our $4 million position in the company or whatever it is, and- and- and we're here to help however we can. But like, you know, our pro rata doesn't change- move the needle for anybody, so let's not bother with it."
- HSHarry Stebbings
I spoke to two mentors this morning,
- 35:40 – 42:16
What do you think about ownership percentage?
- HSHarry Stebbings
and one said to me, "Harry, the lesson for me from 20 years investing, the only thing that matters, my friend, is high ownership levels." And I spoke to another billionaire investor this morning who said, "Harry, I've done a thousand investments, literally a thousand, and the outperformance of the five that I've done, from your Stripes to Notions to Miras to OpenSeas, is so big that actually you should just be in everything with low ownerships." It doesn't... Because it's such high outcomes in the ones that work. How do you feel about the centrality of ownership, and how should I think about those two opposing thoughts? (laughs)
- MKMo Koyfman
I mean, look, I- th- there's lot... There's different ways to play the venture capital business, and we've certainly seen that evolve over the last bunch of years. And, you know, you have folks like Ron Conway that have been playing that model, uh, and getting into the best startups is- is the only thing that matters. Um, you know, I- I sit somewhere in between, to be honest, um...... namely, I mean, I think both things are true. The only thing that matters in venture capital is getting into enough of the biggest winners, and the other thing that matters in venture capital is making sure that you own enough of those winners when they're really big. That's my strategy because I run a classic venture capital fund, where we're not investing in 100 companies, we're investing in, you know, 25 per fund. And so for us, like, the only way to play the, "It doesn't matter, you just need to get into all of the businesses, doesn't matter how much you own, and the winners will take care of everything else," that only works if you invest in a ton of companies and you are convinced that you can get into the winners. So you have to be, like, you have to be elite, so to speak. You have to be one of those seed firms that sees every deal, that is, doesn't want board seats, doesn't care about ownership, isn't going deep, like is playing more of an index role, is comfortable with that role, and believes and knows that they can see everything and get every, into everything because their check size relative to their brand value, reputation, et cetera, um, it works for them. Now, there are a few people that can make that work. There are a few people I've met have made that work. Like, there isn't one way to do venture. That is not how I do venture. Not because it's not a good way to do venture, I'm just not interested in it, to be perfectly candid. Like, I, I don't, I don't get energy from, um, being an index fund. I am a stock picker. I've always been a stock picker. I like picking stocks. I like betting on individual companies. I like taking risk. I like having conviction. And I like being right when I'm right. And so it's almost hard, if you're an index fund, like, you may get right on a few things, but like, the, there's no, you know, how much luck versus how much skill at that. Like, the skill is making sure you see every great deal and you have a chance to get in it. It's not the skill of picking winners. It's a different skill. I like the challenge of picking winners, and so I've structured a venture capital firm where we make many fewer investors, like, many fewer investments, excuse me. We do 10 to 12 deals a year, okay? A deal a month, call it, at, you know, on average. Some years are slower. Right now will be slower. Um, some times are a bit quicker. Last year was too quick. (laughs) Um, but ultimately, we do a deal a month, let's say. So we're focused on picking. So in a venture capital fund structured like mine, where we focus on picking, um, two things matter. You have to pick the right companies, but you can't just index your way into all the good companies. And if you pick the right companies, given, you know, that you do few deals, et cetera, and you really want to drive out-performance, you have to own enough of those companies for it to matter for the fund. Um, now, to be clear, when I started in the business, everybody was trying to own 20 or 25% of a company. Um, the only firm that was incredibly successful, and I hate to go back to them, but they are in many ways the North Star for me, um, the only firm that was incredibly successful at being in the top quintile of venture capital performers, um, without needing 20% ownership was USV. And Fred regularly, and the team at USV regularly, and they did it with us and they did it with others, would split deals. Like Fred split Coinbase with Miki Malka. Um, he split, um, uh, Mark Pincus's company, um-
- HSHarry Stebbings
Zynga.
- MKMo Koyfman
... Zynga with, um, uh, Brad at Foundry. Um, I've seen him do it time and time again. Fred and I just split a deal that we're incubating in the Web3 space, um, where Fred kept taking his amount of capital and ownership down, and like, you know, we were debating it, and like we were going back and forth, and Fred was like, "We can own less. It's okay." Like Fred ultimately was targeting closer to 10% than 20, and his view was somewhere in the middle, which is, you, you don't have to be super, super greedy. Like if, if, if your fund size is constrained, again, back to constraints, right? If you're not raising more than a couple hundred million bucks or even 250 at the max, right? And you own 10% of a company, especially given the level of outcomes that we've seen, um, it's okay to own 10 or 12% of a business. You don't need to own 20. And it turns out by bringing in other extremely talented investors and doing real syndicate building, um, it can really matter during the tough times. And I know over the past few years, it didn't matter, but mark my words, syndicate building, who's around your cap table, how they work together, all those things are gonna matter now more than ever. And so our approach has been, um, it's all about who you pick, but ownership does matter. But again, pigs get fat and hogs get slaughtered. So we're always looking to be pigs. Like we are trying to get double digit ownership where we can, and we, we will do a little bit less here and there, like where we, we will sometimes build our way into positions, we'll buy 5 or 6% then buy a little more in the next round from the C to the A, but we've gotten comfortable targeting
- 42:16 – 47:44
Collaboration in venture - lowest it’s ever been?
- MKMo Koyfman
10 and we think it works for our model.
- HSHarry Stebbings
I'm in a position now where a large fund will not move on 0.6% to let me in to get to my much smaller, much more amenable, and it's the ultimate sign ... They're also LPs with me. (laughs) Uh, but it's the ultimate sign of, like, fucking greed beyond belief, given they're at 20%. (laughs) Like, they're not at 10, they're at 20 and they won't move 0.6 for me, like a friend, an LP. I'm like... But it's the ultimate sign that it's never been less collaborative in venture right now, in my eyes. Do you agree?
- MKMo Koyfman
Um, yes, um, and no. Like everything else, there are exceptions. Like, um, some of the best in the business continue to be collaborative. Um, but yes, we, I've had that issue where, you know, they wouldn't even budge a little bit, um, to make room, and... Even though we're so helpful and additive to the company, both before the investment, after the investment, et cetera. And I, I do agree, I do agree that there has been, um, a lot of, um, just a lot of shortsightedness in the business, and I think these are the kinds of cycles where those sorts of behaviors end up being laid bare, and it comes back to bite people in the ass. I believe in karma. Um, and-
- HSHarry Stebbings
Wha- what- what worries me actually, though, is that it doesn't, because the reduction in capital supply means that the investors actually tend to bully founders more because they can do. So they can say, "No, I'm not letting in Harry for an extra .6 percent, and actually, I'm your lead. You're lucky to have me as your lead. I'm X firm. Thank you." Whereas before, in capital rich times, it was like, "Hey, no, no, no, take our term sheet over the seven others. Oh, you want us to cut down by .6? Yeah, yeah, yeah." Do you see my concern there?
- MKMo Koyfman
I do, and I think that'll happen in some instances, but I also think in markets like this, building strong, durable syndicates matters, and so if some VCs want to play that game and take on all the risk and shoulder all the burden, then God bless them. You know, I will fight against that and I will position against that. I'm in a slightly different bucket than you, in that I'm not trying to tuck into that VC's deal; I'm trying to beat them to the punch. I'm trying to convince the entrepreneur that I'm the better investor for them, that I'm gonna care more about their company, that I'm actually gonna roll up my sleeves and be there for them and I'm not just one of, I don't know how many investments that, um, they don't care about as much. And by the way, the interesting thing about that is, the firms that tend to be that greedy and that aggressive are also the ones that'll drop you like a bad habit, that pay less attention to you, that are much, much bigger, and where you are much less relevant to them. And so, uh, you know, to me, I like when firms sort of take that approach because it's such a stark contrast to what we do. It's kind of an intelligence test for the entrepreneur, or even... And if it's not an intelligence test, it's a test of, like, "What are you looking for?" One of the things I realized over the m- many Years I've been doing this now is, not every deal is right for me, um, and I'm not right for every deal. And you learn it during these decision-making, uh, moments. I, I had an entrepreneur that we had a small check-in, and we were, um, we wanted to r- We, we actually were the first person to offer them a check when they did the round, when they were doing the round. And it was like going into this mess and, you know, they thought, they thought they were gonna get the thing done in seven days, and turned out, like, you know, um, uh, it was gonna get harder, et cetera. And I was on the phone with them and trying to help them and all this other stuff. And in the end, they were able to get a deal done, and, and we were, you know... I, I don't know how helpful we were, but I know we were helpful in sort of calming them down and, and helping them stay the p- stay the course and get the deal done. And, um, and when it came to giving us an allocation in the deal, they basically made no room for us or any of the existing investors. They gave all of the, all of the money to new investors coming in, thinking that, like, you know, that the, the right strategy was showing the people that were keen around the deal some love so that, you know... As opposed to the people that were already in the, the cap table in some way. And so for me, you know, that was quite clarifying, because, you know what? I'd prefer not to write a check into the deal at that point. Like, I saw something in that process and in some of the decision-making leading up to it that just isn't a fit for me. Um, and so, these processes are very self-selecting. When an entrepreneur decides they want to take a venture firm, a, um, you know, a mega-firm that's gonna box everybody out, that's gonna be super greedy, um, but by the same token, you know, you are .005 percent of their capital base... Look, it tells you what that entrepreneur is prioritizing, and they're probably not a good fit for Shine, and I'm probably not a great fit for them. So, onwards. You know why? There's always another deal to do, Harry, and I spend most of my time looking forward. I only look back to learn lessons, but I, I'm not the kind of person that dwells in the past.
- 47:44 – 51:43
Biggest lessons from successes and failures
- MKMo Koyfman
- HSHarry Stebbings
Well, we're gonna speak about lessons before we move into a quick fire. One of my biggest lessons was, I, I had a very similar moment to you there, where the founder literally cut me from, like, 500K with, when I had an $8 million first fund, 500K to 150K, and I was so egregiously pissed off, I was so ready to phone and say, "Not happening. I'm very upset." And then I had an ego check. I realized that I still love the company, and even if they didn't value me, my job is to make as much money for my investors as possible, period. And actually, I think it's gonna make me money, so I called him and said, "Thank you very much." That 150 has now done a 2X on the fund. Um, and I could have let my ego get in the way there, and that would have been a $16 million mistake. Wha- (laughs) So, I guess, like, what would you say your biggest lessons are from your successes and from your failures?
- MKMo Koyfman
Um, you know, it's interesting. I try not to learn, uh, lessons from...... my successes. I've actually found, um, that learning lessons from successes is extremely dangerous because of the risk of confirmation bias. We will convince ourselves of whatever we wanna convince ourselves is the proximal cause of the success, you know, because it was successful. So, I, I, I honestly believe that, um, you can only really learn from your failures. Um, I, I don't believe you can learn from your successes. And what I've learned from my failures time and time again, both in terms of my misses, my mistakes, is that it, it always tends to be very entrepreneur-driven, like, where I misjudged the entrepreneur in some way. Um, and that has been a consistent lesson for me in investing and it's why Shine is such an entrepreneur, such a founder, such a people-focused firm, uh, and why I don't sweat it when, you know, an entrepreneur makes a decision that, like, to your point, it either doesn't allow us in or, or they, they pick a different firm with a different ethos. It just means it's meant to be. Um, this is a people business. These are long relationships, especially when you're writing lead or co-lead checks and taking a meaningful role around the table, whether you're on the board or not. Um, so, so I, uh, that, my biggest lesson is really to, to, to lean into and learn and understand people and figure out if you are, if you have the right chemistry to be partners over time. You know, in terms of, of, you know... My biggest venture win to date has obviously been Plaid. Um, and as I said, I honestly try not to take too many lessons from that investment. But what I appreciate most about Plaid as an investment, um, is that it, it, it required kind of two things. One, a, a belief in a new category f- called FinTech. When I was... When I did Plaid in 2012, FinTech was not really a thing yet. And so having that courage of conviction around a new category, um, was one of the things required to, to make that investment. Um, and many people did not believe in FinTech at that point. And the other was a bet on two great young entrepreneurs. And what it continually... I don't know if it's a lesson, but it, but it continually reminds me to go with my gut and my instincts and not follow the crowd, um, and to always bet on people.
- HSHarry Stebbings
The final one I have to ask you before quickfire is, you know, me and you both are stage-specific in, in many ways in terms of working at seed and Series A. I do a little bit more into growth, um, now, (laughs) whether that's a good decision or not, we shall see in the coming years. (laughs) But my question to you is, you know, we've seen multi-stage firms move earlier and earlier and promised the world, and
- 51:43 – 55:01
How do you advise early stage founders on taking VC money?
- HSHarry Stebbings
we're fighting against it in many ways, if we're transparent. How do you advise founders contemplating taking multi-stage money at pre-seed or seed when they're promised the world from the, you know, multi-stage firms that we compete against?
- MKMo Koyfman
Okay. At, at the end of the day, the more an investment matters to an investor, the better investor they will be for you, so long as, so long as, and this is the key caveat, they are not in a structure that they can't control.
- HSHarry Stebbings
Mm-hmm.
- MKMo Koyfman
What I mean by that is, you know, firms are great but partners matter. And at bigger firms especially, it, it's not just... You're not just taking money from a firm, you're taking money from an individual. Is that individual gonna even be at the firm for a decade? Are they doing their own positioning at the firm? Like, w- w- y- you don't necessarily even know what you're getting when you take it from somebody at one of these very large institutions. These are, these are w- people. These are businesses with hundreds of people working there. The odds that all those same people are gonna be there in five years are zero. Okay? So, so, you know, at the end of the day, when you take, like, w- w- what... So that's why when I s-... What I mean by that is you wanna take money from people where it really means something to them, where they are deeply invested in your success. When you take money from a very big firm, definitionally, at the early stage, definitionally, they can only be so invested in your success because it is a tiny amount of overall capital for the firm, and moreso you have that added complexity that you don't n-... You're not actually getting the firm's money. You're getting money from someone who's advocating for you on behalf of that firm who may or may not be there in the future, so you're taking two risks. You're taking the risk that you're a pimple on the ass of that firm and you're taking the risk that the guy that really cares about you, or the gal that really cares about you, ain't even gonna be there when the shit hits the fan. So if you wanna take that risk, godspeed. But early stage is a very boutique and bespoke business. And while I believe entrepreneurs drive all of the real value creation, um, great early-stage investors can be an unbelievable strategic sounding board. They can guide you in certain ways. When they have years or even decades of experience, they can help you avoid pitfalls or mistakes. They have unbelievable connections. They can open any door. They help you close recruits. They help you open business development doors. Like, there's things that they will do that really matter. And when it matters to them, you will matter to them. And so to me, these things kinda sell themselves. Um, you know, I want people that want me around the pa- the table. I want to work with people that want the Shine team around the p- the, the table. I want p-... I wanna work with people that, that I am aligned with and that we are aligned with. And if that alignment isn't there, then onwards. There's always another deal to do.
- HSHarry Stebbings
There is always another deal to do. And I, uh... (laughs) l- love that, pimple on the ass. (laughs) That's brilliant, Mo. Uh, listen, I wanna move into my favorite, which is a quickfire round. This has been so much fun. So I say a short
- 55:01 – 55:23
Favorite book and why?
- HSHarry Stebbings
statement, you give me your immediate thoughts. Does that sound okay?
- MKMo Koyfman
Sure.
- HSHarry Stebbings
So your favorite book and why, Mo?
- MKMo Koyfman
Uh, my favorite book has to be Portnoy's Complaint by Philip Roth, because it is the most notorious, talked about novel in the American Jewish tradition, but it also happens to be... probably its funniest and smartest.
- 55:23 – 56:35
Keys to a phenomenal burger
- MKMo Koyfman
- HSHarry Stebbings
I hear you make phenomenal burgers. What makes a great burger? Like what are the tips?
- MKMo Koyfman
Interestingly enough, it is about simplicity, focus, and integrity. Believe it or not, it's similar to building a company. The thing people get wrong when they make burgers, and this is especially true in your home country of the UK, where I tried one of those Gordon Ramsay burgers the other day, and it was dreadful, is they try to do too much. They're throwing in the truffles and the this and the that. And the best things in life are the simplest, the most focused, and all of the pieces coming together in a beautiful whole, the integrity. So my burger is a classic American cheeseburger, like modeled after what you would get at an In-N-Out Burger or something like that, just a little more elevated. Um, but really, I mean, simple, simple, simple. And the key to making a great burger is to be... like to get all those little ingredients and all those things exactly right, but do not overcomplicate
- 56:35 – 57:35
What do you know now that you wish you knew then?
- MKMo Koyfman
it. Keep it completely simple. Focus.
- HSHarry Stebbings
What do you know now that you wish you'd known when you started Shine?
- MKMo Koyfman
Honestly, uh, I just- just that I could do it, you know? Like I don't... I took, uh, a longer path to becoming an entrepreneur. I didn't start Shine till I was 42. I, I was on a- an extremely traditional path. Um, you know, um, I was at Bear for a couple years almost. I worked for Barry for six years. I spent eight years, um, um, at Spark, and then I started Shine. Um, and I took some time, uh, in between Spark and, uh, in between, uh- uh, Spark and Shine. I guess if I had to do it all over again, I- I, um, I would have done it a bit sooner. And my advice to anybody with the entrepreneurial inclination out there is that if you, if you have it, go for it. But, you know, as they say, uh, the best time to plant a tree was 20 years ago,
- 57:35 – 1:00:08
What do you wish you could change about venture?
- MKMo Koyfman
and the next best time is today, so, so here we are.
- HSHarry Stebbings
What would you most like to change about the world of startups?
- MKMo Koyfman
Uh, fewer investors.
- HSHarry Stebbings
(laughs) No, really, we're- we're in-
- MKMo Koyfman
No, really. I think, I think we should have... I think we should have fewer investors and some less capital in the system. Uh, I think we've, uh, pumped too much capital into the system, and it's created a lot of bad habits. Um, and I think it's gonna dampen returns, frankly. So...
- HSHarry Stebbings
What are the worst habits it's created? I w-
- MKMo Koyfman
Over-funding of businesses that are too early, lack of constraints on those businesses, founders getting over their skis, being undisciplined, doing too many things, not keeping their eyes on the prize. The best companies are built with focus and discipline, and when there's too much capital in the system, you lose those things. And, um, I think we need to return to a more rational funding market for early stage companies.
- HSHarry Stebbings
Will we? The big funds and so many funds have so much money. Will we?
- MKMo Koyfman
Um... I don't know. Uh, it's un-
- HSHarry Stebbings
(laughs)
- MKMo Koyfman
Uh, honestly, uh, here's what I'd say. I think, um, I think there will be, uh, a lot of folks that go away in this cycle. I watched it in the last go-round. Um, you know, Spark and USV and all these firms didn't exist, um, before the last cycle, and they really made their names coming out of the '08 crisis and, and on the other end of that cycle. I think we'll have a similar reckoning in the venture world over the next few years. Um, I don't think it means that, um... An- and by the way, and I think some of the late stage and the crossover guys are kind of pulling back from that business. So yeah, I- I do think the amount of capital that has been poured into startups will shrink. Um, I don't think it's going back, you know, uh, to levels we used to see. You know, things, when they grow and they reach a new plateau and they come down a bit and they grow up. So, so I- I think, you know, capital will continue to come into the technology business because obviously a- a great place to deploy and a great place to create value. But I do, I do think we will have some rationalizing of capital, and I think we'll have a lot of tourists leave the system, and I think we will separate winners from losers through this cycle, and I think that'll be healthy for the ecosystem.
- HSHarry Stebbings
Penultimate one. What three traits would you most like your children to adopt?
- MKMo Koyfman
Relentlessness, integrity,
- 1:00:08 – 1:00:52
The next 5 years for you and for Shine Ventures.
- MKMo Koyfman
and generosity.
- HSHarry Stebbings
And then final one, what are the next five years for you and for Shine? If we chat in 2027, where will we be?
- MKMo Koyfman
If it's up to me, I- I hope to build a top 10 early stage venture capital firm, and I wanna be on that list for every seed or Series A company that's in our wheelhouse. Uh, I- I- I want them to be thinking of us and coming to us and at least give us a shot.
- HSHarry Stebbings
Mo, this has been such a joy for me to do. As you can tell from having the schedule beforehand and then chatting, we didn't really stick to it, but I loved the discussion. You were fantastic. So thank you so much.
- MKMo Koyfman
It's absolutely my pleasure. Um, and really, really appreciated spending the time.
Episode duration: 1:00:52
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