YouSaid · the spoken record

Jon Callaghan

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23
first
2017-09-06
most recent
2017-09-06
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1
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podcast

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  1. “Yeah, sure. So most recent public is a company called Brava that got a little bit oppressed this week. The simple thing about our business is if done right, you're investing behind great people in great markets, and that's very simplistic, but it is actually true. So John Pleasance is the CEO of Brava and someone that's just had a remarkable career and someone I've known extremely well. And so he's pursuing what is a stealth market, call it something in the home with incredible team and technology. And you just have to be in business with John Pleasants. And his team, by the way, this is their second time together fully. Some parts of them have worked together many times in the past. And great entrepreneurs recombine with their teams, great talent sticks together. They want to continue to have a career together and Brava is a great example of that. It took about, well, you know when you see it, one of the things you say it true is you know when you see it and nothing's easy in this business but investing behind John and his team is incredibly easy.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “Well, I'm glad for what I learned along the way, but I would say take more risk. If I were telling my earlier career self something, I would say, again, to the wild ocean, be out there, be further out. The truth of the matter is that our business is about being comfortable with massive amounts of ambiguity and risk. And yeah, I would say more conviction for everyone and more daring be more bold.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “Enterprise, but I would say industrial is a better way to say it. I think Brad calls it the rise of the machines or there's just incredible automation that's happening and it's backed up by software-based technologies, machine learning. And yeah, a little bit of AI and decision making, that kind of thing, but in computer vision, but we're seeing a lot of very, very large industrial robotic opportunities. And it's real. I mean, real revenues, real scale. So I think that that's the thing people aren't paying a lot of attention to. Again, in industrial settings.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “To pursue that quest. And it is not, it's really out in the ocean. I mean, you've got to be so far ahead in this industry. And we just constantly think about that at True, is how can we be out in those very, very uncomfortable not-for-giving places”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “If you're good at what we do, you're out chasing the whale in the middle of the ocean and there's nobody else around and the elements are against you and there are sharks in the ocean and there are crazy captains on the ship and there are strange other things just all around you. If you're really, really good at early stage venture, that's where you want to be. You don't want to be at the rosewood schmoozing with other VCs trying to figure out what they did and what you can do to be a little copy of that. You've got to be out in the frontier, be way out there. And Moby Dick is just the classic, like in search of the white well. We are all searching for the white whale. It might be called Google or Facebook or Peloton or Fit or whatever it is, but that's what we're after. And so that book to me, and there's kind of a newer version, a really phenomenal, newer version called The North Sea. But that book to me just epitomizes the really grandness of our quest and also where we should be when we're trying to”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “Such a good one. So I'm a just voracious avid reader. I was lucky enough to work with Otis on Goodreads and a bunch of other book lovers. And it's just one of my passions. But for sure, for what we do, you just can't beat Moby Dick.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “How can I help you with that? Is there anyone on your team that needs me to take them out for a cup of coffee and just say, hey, great job on this, great job? You know, we can do a lot of really interesting things. Is there anyone at big company ABC that you want to talk to about AWS or Google Cloud, that kind of thing, right? There are lots of ways we can help, but we have to be aligned behind the founders goals and objectives.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “I think that's the easy in the early stage. Of course, in the later stage, boards can do worse things, but I think it's distraction in the early stage. It's, you know, the board's job, again, in my view, in the early stage is to really support and empower that founder. And oftentimes I see boards distracting teams. By the way, there's a fine line. So there's a fine line because the boards fly at, you call it 40,000 feet, right? And the entrepreneur is day-to-day at the ground level working through the business. And so that 40,000 foot perspective can be super useful, but it can also sometimes not be useful. The founder can go back and say, like, that's the last thing I want to think about is how AI impacts my business right now. Like what I'm really figuring out is why my product's not working as well. So, you know, I think we have to be careful as well to make sweeping generalization. But what I do see a lot of is a lot of this distraction versus saying, okay, we're all on the same page. I might want to talk about AI a lot, but you just told me for the next four weeks you're in a sprint. It's all about product.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “Lonely, really, really scary. And you may have co founders, you may have mentors and friends, but you can't often share what's really on your mind with people that are close to the company, employees and people you've recruited and stuff like that. So the board's a really interesting place to do that. And of course, boards typically have various agendas, and investors have probably other agendas and other directors, but it's a pretty safe close place to really share what's going on in the early stages. As the board grows, of course, the responsibilities change. And so things like duration, 90 minutes for a board meeting, frequency, six weeks, agenda, you're allowed sure you can send me what and the other directors, whatever you want in advance.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “And remove obstacles. And of course, every board has some of that. I would just say the percentage of time devoted to strategy leadership versus reporting in an early stage company is kind of like 90% on the first two and 10% reporting. If you're doing your job as an early stage investor just with a founding team, you should really know what's going on at the company, not so much day-to-day, but you should be very, very close to what the objectives are. So the reporting role is much smaller. And oftentimes I see startups that say, great, we're going to have our first board meeting, my lawyer or so-and-so or my mentor says to do it like this, and they come in with a usually a really long series of slides, or even, you know, worse, a Word doc, and they just sort of start reading through all the things they've done. And I honestly usually tear that up. Literally tear the pages up and say, that's not what we're here for. We're here to pick the one thing that's important to you and that you're worried about and talk it through. Because the truth matter is being a founder is really, really”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “Word meanings in later companies are designed to report the progress of the management team to effectively the shareholders. That is the legally the official construct, right? Shareholders elect the board, the board, an official in corporate law, the board hires and monitors the management team. So in later stage companies, even B and C stage companies, that construct tends to be more appropriate. There's a lot of things happening at a company. There are lots of different shareholders, there are lots of different constituents that the board needs to represent. And so it's a very appropriate construct. The problem is in early stage companies, and by the way, so again, I just said the word reporting a lot. So the job of the board is essentially to be reported to. We don't think that that's really appropriate. It's at one small role for a board in a seed or series A stage company. And really, the board needs to, again, embolden, empower, protect, you know, focus, right?”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “Your research is great. I'm wildly passionate about board meetings, about startup board meetings, constructing startup board meetings to better serve the CEO, founder CEO, but also better serve the management team and better serve the strategy of the company. And so I've written a little bit about this. I'm writing more. I think board meetings in startups as a rule do not serve the founders of the startup companies at this point in time. And I think that's, by the way, a wildly blanket statement, but I just think in general, the construct of the traditional sort of BC stage company board meeting or beyond or public company board meeting doesn't really fit to a seed series A startup. And so what do I mean?”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “Exactly right. How are you helping? So, you know, so literally we design our team, you've seen our team, we design the way we operate to basically never be that kind of partner to our founders. A few hundred investments later so far so good.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “How we've done everything it true, and it's easy to say, but the truth of the matter is, most venture capitalists are the incentives are such in the industry to hold your cards close to the vest in terms of indicating your interest in further investment. And we don't do that at true. Our cards are all on the table. We're partners with our founders and hopefully perfectly aligned. And so we're very”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “In the early days, terribly constrained on what the product needs to look like, because in our experience it's a bit of a wandering road in terms of finding the actual product and the actual product marker fit. But we do need data to make subsequent investments. So product and launch is one team. You have to be able to hire and recruit, and it's very competitive. It's hard to do. And it's a great testament to leadership. It's a great testament to the concept. It's great testament to the potential for the market. But hiring's only step one. You got to build a culture. You've got to build a culture that's durable and that can sustain growth and can empower growth and actually can properly manage the next 10, 20, 30 million dollars of capital. So it's really all aspects of the opportunity that we're trying to evaluate after that initial investment. So clear expectations up front. And then an open conversation in between investment decisions about those expectations and how they're being met. And so authentic communication is absolutely critical.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “To see the best markets, there's no one operating in them today, right? So if we're doing our job right, we're out in the wild with very few data points to look at. But we have a methodology for being out in the wild and we have a methodology for thinking about markets. And so allowed to dream on the first check. But the second, third, and fourth check, that's challenging, right? That's more there is data. And so you actually do need to switch into much more of, I would call it, instead of a dreamy hat, sort of a more judgy, which is a very uncomfortable place to be. But it's not necessarily judging necessarily only the product or only you have to judge is this opportunity worth, again, coming back to this, the founder's time. And that tends to put things into very close alignment force. And so how do we do it? Our expectations when we write the initial investment check are super clear. So we're almost always there day one. So there is no product and therefore one of the objectives of our initial investment is build a product. Can we launch? We're not necessarily...”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “Yeah, absolutely. And it's a critical part. You know, the dirty little secret of venture capital is half the time we lose, more than half the time, but half the time straight off the bat as an industry, we lose. I always say to friends starting in this business, the number one thing you have to do is get good at losing because it's going to happen way more number of times if you're doing this right than winning. Winning's, by the way, pretty easy. It's not easy to do, but it's easy to do enjoy and everything goes right. But losing is really hard. And so instrumenting both the firm and again, coming back to the psychology of your team, right, and structuring your team and your decision making process so that you actually support risk in the early check, what we say is in the first check, you must dream, right? The first check is art. The first check is really understanding whether or not the initial decision. I keep saying the first check, that's probably bad, but it's probably a bad phrase, but like the initial decision, when you decide to support an entrepreneur's vision, you need to dream because the best things are not easy.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “Early in big markets, whether it's in MakerBot or Fitbit or WordPress or Peloton or all these names and things. But what really what true is all about is being consistently early in very large markets with the best entrepreneurs.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “I think it's not meant to be provocative, but sometimes it does provoke reaction. And the short answer is people say, tell me more, how. And then we describe a lot of elements to our strategy at true, which is not just about, again, the asset allocation was structurally aligns us to take big risk, the size of the funds, the size of our team. We have by far the largest and most talented entrepreneur team in our segment. There's nobody even close in terms of in the seed segment that has, you know, Tony Conrad, Tony Schneider, Ohm, Kevin. I could just go on and on. And we have just an enormously talented and deep team, all of whom have started companies in their career. So anyway, so the answer to that is not, you can't just say it. You have to then describe your strategy of how you do it. And we have a very cohesive strategy for doing so. And we're very public about it. We talk about all the time. And the good news is now we're 11 years old and it works. The strategy consistently puts us.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “The way we think about it, again, if you think that the creative founder is our society's most precious resource, which I do and we as a firm believe that, then their time, the founder's time, is worth way more than all of the capital we have at true. So we manage now seven funds, a billion, four or so, something like that in capital, but just one founder's time and opportunity cost is so much more than that, so much more valuable than that. And so with that in mind, we want to try big things. We want to be out in the frontier and we want to empower those founders to Things and not worry about failing. And when I say not worry about failing, of course nobody likes to fail or not have things work out. That's not it. But to be not just structurally aligned to be bold and take a big swing at a market and be far ahead, but also psychological.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “Means alignment, and that's literally one of our core founding principles is to frankly align ourselves fully with the founder and their teams. And so as we think through, we've designed literally every aspect of the firm, including our investment allocation process, how much we invest and when and how. Follow on things. We designed it to be fully embracing and supportive of the founder from day one. So it's powerful.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “Is essential to your role as an early stage investor, certainly here at True. Because People in our economy today are the startup founders. And the most daring and bold and also frankly the least supported are those startup founders. And so it's not just about raising your first initial seed rent of capital. It's about all of the other things you as a founder need to succeed. Recruiting a team, building a culture, access to the industry, downstream capital, which we'll talk about in a bit. So we think it's essential to be fully aligned. From day one, and so the name of the firm is true.”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “Absolutely. We started true and we actually named the firm true because we thought that entrepreneurs A better, more aligned partner in their Partner on their board For the life of the business. And frankly, we really thought the needs of the startup, the what we call the And their teams, we thought they were underserved, and we think that the role It is to fully support and fully embolden. Major risk and be bold and daring. And so the answer to that question is yes, we think the entrepreneur. Mindset and also”

    2017-09-06 · The Twenty Minute VC · 20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan · IDENTIFIED FROM THE TRANSCRIPT · source